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Sweetness Chapter 1 (1) It started with an accident. I mean that; I did not want one of my many secrets getting out, but you can't plan everything. In my case, I didn't plan on rolling my SUV. It was a Thursday and it was early, too early. I had just left the golden arches and with a fresh cup of piping-hot coffee, I was ready to start my work day. The sun wouldn?t make an appearance for a while yet; when you own your own company, you start early and stay late, and I almost always started early. I took a sip of my coffee, enjoying the smell of it more than the taste. There is something about the smell of coffee that wakes me up. I took a sniff, smiled, took a sip, and just as I was putting the steaming cup of black coffee into its cupholder, that?s when it happened. And it was bad. I entered the intersection, the light in front of me glowing a bright green in the predawn hours of that Thursday morning. Too late I saw the car coming my way. I swerved from the right lane into the left, trying to avoid what I knew was coming, but it didn?t help. The car, some older model I couldn?t quite place in the dark, hit my Explorer on the right-hand side, plowing into the passenger?s side door with the powering force of an angry bull. My SUV lurched, wobbled and then went onto its side. My coffee toppled, spilling onto my legs. I could feel the heat of the liquid through my pants and winced in pain, sucking in an angry, wet breath. The car that hit me kept moving, pushing my SUV forward and finally onto my side. The car kept going, finally swerving, but it was far too late. I was upside down now, staring in some weird way at the back of my head. It was an eerily odd out-of-body experience. For the life of me I would swear that I was watching the action from the back seat. I could see out the windshield at the ground now inches from my cracked windshield. I could see the hair on my head hanging straight down and I could see that coffee cup sitting on the roof of my car that was now sliding noisily against the cracked, gray hardtop. My SUV toppled again, leaving me lying sideways in my seat. I returned to my body as my vehicle righted itself. I stopped moving, taking stock of where I was. I was sitting upright, which was a plus, but my vision was blurred and had taken on an odd pink hue. Blood. There was blood in my eyes. My legs throbbed from where my McDonald?s coffee had burned me. My left arm hung limply, resting in my coffee stained lap. I reached down, searching for something, anything and found a t-shirt that read ?Bazinga!? It would do. Keeping my head perfectly straight and pressed against the backrest of my seat, I brought the t-shirt up to my forehead, using it to stop the flow of blood. My head hurt, my left arm throbbed, my legs felt like they were on fire. Through the broken windshield I could see a few stopped cars. I heard a voice, low and muffled, like it was coming to me from under water. ?Mister? Are you okay? I saw everything. I?ve called for an ambulance.? Ambulance? Did I need an ambulance? I think I nodded, but I can?t really be sure. The headlights from about a half dozen stopped cars, stuck now because of the accident, becoming blurry. I used the t- shirt, now stained with blood, to wipe my eyes but those headlights still retained that hazy, out-of-focus look. I heard a siren. That wasn?t good. Someone needed help. I hoped they were okay. The siren grew closer. The windshield was cracked, and it bothered me that I was going to have to get it fixed. Why couldn?t anything be easy? I had so much work to do that I really didn?t have time to get my windshield fixed. How did it get broken in the first place? ?Sir? Sir?? Was someone talking to me? That?s odd. I?m sitting in my car by myself. Why would anyone be talking to me. ?Sir?? The windshield bothered me. Why was it broken? ?Sir, do you know where you are?? Accident. I was in an accident. It came back to me; the car sideswiping me, pushing me as I was changing lanes to avoid the collision that I could not avoid. I remembered seeing the back of my head as I seemingly sat in the back seat taking in a violent movie that was all too real. I recalled the smell of coffee and how the pleasant smell and acrid taste had started to wake up my groggy brain. I could still smell the coffee, most of it on my pants and dripping onto my head as I sat, unmoving, in front of the steering wheel. Anger flared in me. I couldn?t help it. ?Who hit me!? I hissed, holding my head still. I knew that much. Don?t move. Don?t do any more damage. ?We?ll get you out of there in no time. Do you know what day it is?? I did. ?Thursday,? I replied, still not turning to face whoever was speaking. ?What would you say if I told you it was Sunday?? ?That it took you guys a long time to get here.? I could hear him smile, even if I couldn?t see it fully from the corner of my eye, ?You?re going to be okay.? That was a relief. Was that ever in question? His final sentence seemed to hit me in some deep part of my mind. How bad was the accident? I had rolled my car, sure, but I was awake and even though I was hurting, my left arm throbbing with each beat of my heart, I didn?t feel like I was in grave danger, but was I? ?You?re going to be okay.? Kind words but words that scared me more than they should. ?Thanks,? I said. The anger was still there, I could hear it as I hissed out that lone word. ?You?re going to be okay.? Was that for me or for the paramedic that was now reaching in through the broken window to put a brace on my neck. ?Try not to move.? I didn?t move. ?You?re doing great,? he told me. ?The door is jammed. We?ll have to get the Jaws-of-Life to cut it free. Don?t worry. You?re going to be fine.? Was fine better than okay? I thought to ask him but then it dawned on me that my windshield was broken, and I was going to have to get it fixed. How did my windshield get broken? It wasn?t just cracked, it was shattered. What happened? Did I get behind one of those horrible trucks carrying a load of rocks? Did the rocks bubble out of the truck like popcorn spilling from a pot of oil? God, I hated those trucks. ?Stupid truck.? I was angry at that truck and at how inconsiderate the driver of that truck had to be. Why did the driver not put on that shredded tarp to prevent at least some of the rocks from pounding my windshield? To my left the door was pulled open. ?Keep still, sir,? someone said as I reached over to try and shut the door that was no longer there. You can?t drive with the door open. Oh, I spilled my coffee. I must have. I could smell it everywhere. Hands grabbed me and eased me from the car. The world looked so much clearer when you weren?t seeing it through a broken windshield. I shut my eyes. That was better. My head didn?t hurt as much. I felt my t- shirt being pulled out of my hand. ?That?s mine,? I said, opening my eyes briefly before shutting them again. My head hurt so much less with them shut. ?It sure is, sir,? someone said. Next to that voice a different voice said, ?We?ll give it back.? ?Good.? And it was good. I felt a pinch in my arm and a few moments later everything felt better. (2) ?We?re going to send you up for a CT scan,? some young intern said. ?Once we get the results back we should be able to remove that neck brace. We?ll keep in on for now. Any questions?? ?No, doc, I got it. Thanks.? I gave him a smile. ?Good.? I watched him leave the curtained off section of the ER where they?d brought me following a brief ride in an ambulance, pulling the curtain shut as he left. The accident had to be bad if they brought me there in that portable doctors office. No waiting. That was good. Your own personal doc-in-a-box, and a mobile box at that. Nice to have, but if you needed one then it really was bad. My memory stopped doing its weird topsy-turvy thing, coming in and out like an old AM radio station just out of reach. I recalled the accident and everything leading up to it. I no longer questioned why my windshield was broken. Rolling your car tends to do that. Still, the mild concussion I had seemed to be fading somewhat as my mind was fully lucid and the only thing left was anger at the other driver, and the thought of how busy work was going to be when I returned to it. Work was busy. Hell, work was always busy and running your own company, with nineteen people working under you, made that work somehow harder. All those people relying on you to lead them down the proper path was at times daunting. I was good at it, even if I sometimes wanted a break. Rolling your car and spending a day in the hospital was not the kind of break I wanted. An orderly came in. A big, black guy with one golden tooth. ?Good morning, Mister Sweet. How are you today?? ?Fine,? I said, unable to nod thanks to the brace around my throat, but trying anyway. ?I?m gonna wheel you up for your CT scan, okay?? Consent was a big thing in the hospital. After wheeling me into this little curtained oasis, a woman had come in and had me sign about half a dozen documents, insurance information and consent forms and that was before a doctor ever came in. ?That?s fine. Thanks.? The orderly helped me into the wheelchair and chatted about the Utah Jazz and how silly they were for trading away some player that I?d never heard of. I knew about Shaquille O?Neil and Michael Jordan and Scottie Pippen, but I had no idea who the orderly was talking about. I nodded as best as I could with the brace holding my head in place, but truthfully, my head didn?t move that much. He wheeled me to the room with a large medical device. I?d seen them on television shows, but this was the first time I?d ever seen one up close. It was big and bulky with a long table sitting in front of some deep bore. A woman helped the orderly lead me from the wheelchair and onto the platform that sat in front of the scanner itself. The orderly left, ?Be back soon, Mister Sweet.? The tech that ran the machine was older than I was, with gray hair that perfectly matched her gray scrubs. ?This won?t hurt,? she said. ?Have you had a CT before?? ?No, ma?am.? She swatted my shoulder, ?no need to call me ma?am. It?s Cathy.? Another nod that wasn?t a nod. ?Okay.? She explained what was going to happen and it pretty much happened exactly that way. I went into the bore, feeling a bit confined, and watched as something big spun around my head. Cathy told me to hold still and I held still, not realizing I had been fidgeting until she scolded me. The table I was lying on moved at a slow, almost glacial pace as that big contraption spun around my head. And it lasted about thirty seconds. Zip, zip, zip. The table moved out and mister gold tooth was back to help Cathy put me back in the wheelchair. ?All done,? she said. ?I hope you feel better, Mister Sweet.? All-in-all, Cathy was very nice. ?Thanks.? I was brought back to the Emergency Room and put in a room without curtains. A room all to myself. A little block was affixed to my finger to record my pulse and another was wrapped around my arm to record my blood pressure. Some news show was playing on the television set mounted in the corner, showing the weekend weather. Outside my room, people walked by, some in scrubs, some in jeans. Visitors and nurses, patients and doctors. I just lay there, noting that warmer weather would be moving in over the weekend and how it would be close to a record high. They seemed to say that a lot. It was twenty minutes later when I met her. Peyton. ?Hello, Sweetness,? she said, smiling at me. It was a warm smile and it lit her pretty face. She had dark skin, not exactly tan, but darker than my own. Her black hair was pulled up into a ponytail. She was wearing green scrubs that hid her figure, but that seemed to somehow make her even more appealing. Or maybe it was that smile. That smile that both kept and told secrets at the exact same time. ?How are you today?? Her voice held a little mirth in it, like she was playing a game that only she knew the rules to. A game that she was winning. ?Fine, thanks.? ?I?m Peyton and I?ll be taking care of you until we let you go home. If we let you,? she added, smiling, her face somehow lighting up with the size of her grin. ?If?? I didn?t like the sound of that. ?Am I okay?? She laughed, a light, happy sound that was both musical and full of mirth, ?I?m just toying with you,? she smiled, saying something more with her eyes that I couldn?t read. ?You?ll be fine.? She crossed the room to take the readings off the machines hooked to my body. She bent low and whispered, ?We?re going to have such fun together.? I wasn?t sure I heard her correctly. What did that mean? Maybe my concussion hadn?t quite cleared up. ?I?m sorry?? She stood and said, ?The doctor will be in soon.? She walked towards the door and stopped. She looked at me and smiled, ?Yellow. Nice.? I wondered what that meant - until I didn?t. Then my face turned red, damned near scarlet. You see it, don?t you? Why I was embarrassed. We?ve all heard the saying to wear clean underwear in case you get into and accident, and I was in an accident and I had been wearing clean underwear. Yellow ones. Panties to be exact. You see, I like panties. It?s sexual, sure, but it?s more than that. They calm me; they make me feel more like me. They?re softer and, well, prettier than men?s underwear. I?ve been wearing them for years. It was one of the reasons my ex-wife and I separated. She had said so many times, ?I hate that you wear panties.? Then her voice would grow colder, ?And I hate that they?re more feminine than mine.? I could still hear my response, ?Then wear sexier ones!? I never offered not to wear them. Not once. She had groaned or grunted or cussed me. It was an argument we had had more than once. I tried to explain how much I liked them, but she didn?t want to her it. In her mind, men did not wear panties and since I did then I simply wasn?t a man. It was a tired argument in a tired marriage. She couldn?t accept that I liked panties and at the end she couldn?t accept me. So, living alone, I no longer gave it any thought what I wore under my pants. I wore panties. The more feminine the better. Silky lace panties in pastels with little bows. Blues and greens, pinks and purples. And, of course, yellow. And I had been wearing yellow panties with a scalloped lace waistband. I was wearing them now. The back was sheer and full. They felt sexy and I enjoyed them. They were one of my favorite pairs. I had been wearing them when some idiot driver had crashed into my car, sending me along on a horrid E-Ticket ride straight to the hospital. I?d been hazy and drugged, suffering from a concussion, and didn?t think about the nurses cutting my clothes away to dress me in a hospital gown. How many people had seen my panties? Peyton obviously had. ?Yellow. Nice.? I recalled what she had said. ?We?re going to have such fun together.? What did that mean? I lay on my bed, the TV in the corner now playing a rerun of Family Feud. Steve Harvey was asking a homely black woman some question that I couldn?t exactly hear. Not that it mattered. I kept replaying what Peyton had said. ?We?re going to have such fun together.? I was worried, but the more I thought about it, the more I thought maybe it would be okay. I thought about Peyton. She was pretty. Dangerously so. I was still thinking about her when she came strutting back into the room. She had an air of authority about her. Which made sense; at least she was wearing pants. I couldn?t help it, but I wondered what color panties she was wearing. I had that thought about every woman I found attractive. Peyton came in, flashing me a smile that said I know something you don?t know. I could almost hear her singing it. Of course, she knew. Everyone that worked on me following the accident knew, but she was the only one that had the temerity to comment on it. Maybe temerity isn?t the right word. Maybe I should call it what it is. She had the balls to say it. Still smiling she asked, ?Do you always wear panties?? I tried to swallow but couldn?t find the spit. Her voice wasn?t heavy with malice. There was a gentle playfulness in it. And something else. Something I couldn?t place. ?Oh, don?t be shy,? she wasn?t trying to hide what she was saying. Me, I always hid the fact that I not only wore panties but loved them. She spoke with a subtle strength. She was smiling as she continued, ?I asked you a simple question and I expect an answer, Sweetness. Do you always wear panties?? I licked my lips, found my spit so that I could swallow, but I still couldn?t find the words. I thought of denying it but what could I say. I was still wearing them, and Peyton had obviously seen them. Too many people had. Why had I worn panties? But the answer to that was simple. I wore them because I loved them. Finally, with Peyton standing at the end of my bed watching my struggling debate, I nodded. She smiled, her whole lovely face somehow becoming even prettier. ?Lovely. Simply lovely. Do you wear anything else? Anything naughty?? ?I don?t think that?s...? She interrupted me, ?That?s right!? ?Huh?? She smiled, ?You leave the thinking to me. You?ve said enough.? She checked the machines hooked to me and waggled her fingers at me as she left. I watched her go. What was going on? Once again it felt like I was playing a game where I didn?t fully understand the rules. Somehow Peyton had me flustered. Was it because of her knowing my secret or was it because she was so damned pretty? She had black hair that when pulled from her ponytail would surely hang to her shoulders and deep brown eyes, the color of the rich soil, painted with some soft subtle hue. Her figure, hidden by her scrubs, seemed to reveal itself tantalizingly so and when she moved it was fluid and graceful, like a figure-skater sailing over ice. Another episode of Family Feud came on. That homely black woman and her family had joyously won a new car and two new families were battling on the television while I lay there wondering what game Peyton was playing. The one with Steve Harvey would be so much easier. At least I understood the rules of Family Feud. Peyton was toying with me. That much I understood, but I didn?t know why. It didn?t seem like she was being cruel. She seemed accepting of my panty fetish. More than accepting. She seemed to like it. ?Anything naughty?? she had asked, and that last word had been elongated into a sensual sound that gave me chills I hadn?t felt in a long time. Back when my ex-wife and I had been happy. The doctor came in, told me that I was okay and that he?d be sending me home as soon as the paperwork was done. My left arm had a slight sprain that would resolve itself with ice and my concussion had been mild enough not to cause too much problems. I no longer needed to be kept awake and under observation. I had four stitches in my head. They?d have to be removed in ten days. My legs were barely pink from where the hot coffee had soaked my slacks. It could have been much worse. ?Thanks, Doc,? I said. I guess I was okay after all. He left and not thirty seconds later Peyton came strolling back in. ?Well?? I knew what she wanted. I had been thinking about nothing else, but I didn?t want to admit it. I?d grown very good at hiding my fetishes. I kept my mouth shut. She raised her eyebrows, waiting on me to answer her question. I couldn?t do it. She caved first but when she spoke she did not say what I expected. What she said gave me chills. ?I guess you want me to punish you. You won?t like my punishments.? What did that mean? She kept making me ask that question. She waited a moment longer. ?A punishment then. We?ll get that out of the way soon enough.? ?What do you mean?? ?Oh, you can speak. I know all about you, Sweetness,? she said, her eyes wide, her smile lifting her cheeks. ?I read your file. I know where you live. Oh, and that little checkmark on divorced. Lookie here,? she reached inside her scrubs and pulled on a thin piece of elastic, flashing a small swath of red. ?My panties aren?t as pretty as yours.? She watched my eyes, ?Oh, you do like panties, don?t you?? Peyton laughed then, and it was delightful. ?So, I already owe you one punishment and we?ll get to that shortly, but do you want to go for two? I promise you don?t. Now, Sweetness, tell me, do you wear anything else?? She then repeated her sexy question from earlier, ?Anything naughty?? And just like before she dragged the word out. How could I answer that question? That I did own a few other things like one extreme corset that I bought on a whim. And two pairs of heels that I loved almost as much as I loved wearing panties. I couldn?t admit that to anyone, including Peyton, could I? And what did she mean about her wanting to punish me and, more importantly, why was I excited about what that could be? She laughed again. ?Oh, you do! That?s awesome! So much fun.? She left the room and came back two minutes later. ?Now,? she said, ?I owe you a punishment and I think that the punishment should fit the crime. You didn?t want to answer my question. That was naughty.? I loved the way she said that word: both playful and sexy at once. ?Since you didn?t want to speak, well, let?s give you a reason for being quiet.? She reached into the lone back pocket of her scrubs and pulled out a piece of red fabric. ?Open up,? she said. Her panties. Was she going to gag me with her panties? And why did I want her to? ?Sweetness.? I looked at her. She was giving me a gaze full of power. She was a woman used to getting her way. It dawned on me that that air of superiority wasn?t an act. She was superior. I opened my mouth. I couldn?t help myself. I wanted those panties. I wanted to see them. Taste them. Own them. Hell, I wanted to wear them. Smiling, Peyton placed her panties into my mouth. They were wet. I could taste them, a strong taste that was both pleasant and acrid. She pushed them deeper into my mouth, one tantalizing bit at a time until my mouth was full, my cheeks bulging. ?There,? she said. ?Now you have a reason not to say anything. If you?re good, I?ll let you take them out before you leave the hospital.? She smiled. ?But I doubt it.? She left again. I watched her go, looking at her ass as she left. She wasn?t wearing panties and that somehow made her retreat even more tantalizing. I tasted her panties, sucking on them, savoring the taste of her body, her piss, her sweat. It was the most intimate I?d been with a woman since my ex-wife had left. Was that why I let her gag me? Was that why I kept them in my mouth? I lay there, gagged, waiting to be discharged, trying to find answers to far too many questions. An orderly came in and cheerfully told me it was time to go. I couldn?t speak so I just nodded. He gave me a pair of scrubs and waited out in the hall while I got dressed, hiding the sheer yellow panties that Peyton and who knew how many other people had seen. I found the orderly in the hallway where he helped me into a wheelchair and soon enough I was wheeled to the front of the hospital. I was still gagged with Peyton?s panties. I had not spoken a word since she had shoved them into my mouth. The orderly left me alone. I stood, staring at the darkening sky. I had lost most of the day. I couldn?t help but wonder what had taken so long. I glanced from the sky, back into the hospital and back to the encroaching darkness again. I had to get home, but my car was totaled, my cell phone lost, probably in the wreck. I needed to make a phone call which meant I was going to have to take the panties out of my mouth. Was that allowed? Where did that thought come from? Did I need permission to remove Peyton?s panties? More importantly, did I want to ask for permission? I found that I did. Peyton had somehow captivated me with her smile, her playfulness, her dominance, and maybe more importantly, her acceptance. Yes, that was probably the most important thing. ?Follow me,? Peyton said, coming up behind me. ?I?ll take you home.? She started walking, not bothering to check if I was following her or not. I followed. (3) ?Okay,? she said as my seatbelt clicked shut. ?You can take my panties out of your mouth. But,? she smiled at me, ?I expect you to wear them tomorrow.? I whimpered. I didn?t mean to, but I did it just the same. The sound caused Peyton to laugh. ?You like that idea, do you?? I nodded, fishing her tiny panties from my mouth. They were wet but this time for a different reason. I looked at them, a small thong, barely any fabric at all. Peyton was a small woman; the panties were tiny. I doubt they?d fit but I wanted to wear them. I enjoyed holding them in my hand, I knew I?d enjoy wearing them even more. Peyton drove me home, talking the whole way. She told me about her childhood. How she was an only child, that her mother had died while four months pregnant. She told me about her father, a small man with small ideas and a great big heart. She did most of the talking, dominating the conversation. She talked about what she wanted to talk about and only let me speak when she wanted an answer to a question. She learned about my own parents, living in San Diego because they both liked the warm weather and the cool Pacific water. She learned about my two older sisters and laughed when I admitted that I had to wear their more androgynous hand-me-downs. ?God,? I said to one of her questions. ?It was so humiliating wearing my sisters? pants to school and having one of the senior girls call me on it.? ?Did it turn you on?? ?What?? ?The humiliation? Did it turn you on?? ?No. Of course not.? She looked from the road and back to me. ?Uh-huh.? She didn?t believe me. Maybe it was the blush on my face or how I had hesitated before answering. She followed that with something that terrified me, ?I guess we?ll find out soon enough.? I didn?t like the sound of that. Or did I? I didn?t expect to crash my car and I didn?t expect to be so captivated by the lovely young woman that was driving me home in her old Accord. She steered the conversation to my divorce, learning far more about me than I usually revealed. But then again, she knew about my biggest secret, the one that I kept from everyone. The one secret I had even kept from myself for the longest time. Growing up, I had worn both my mothers? and my sisters? panties, never admitting how much I liked them, only knowing that I did. It took a long time to even admit it to myself. Hiding pilfered panties from my family, wearing them when I had the chance. I knew I liked it, even at that young age, I just didn?t know why. I hadn?t even heard the term fetish until I was a junior in high school when I happened upon a discarded Penthouse Variations magazine that someone had thankfully discarded. Peyton pulled into my driveway. ?Invite me inside.? ?Would you like to come in?? She threw hear head back and laughed. ?I?d be delighted, but we haven?t had a real date yet and it wouldn?t be proper. Now, ask me out.? ?Would you like to have dinner with me,? Friday was date night, ?tomorrow?? She repeated her line about being delighted. ?Tomorrow, then. Thank you, Sweetness, for the rather pleasant day. We?re going to have a great time.? I got out of her car and watched her drive away. Only then did it dawn on me that she had never once called me by my name. She had only called me Sweetness. Was that a play on my last name or something else? Something fun? Something sinister? I realized that I couldn?t wait to find out. I walked to my door and realized I didn?t have a key to get in. My keys were with my phone inside my totaled SUV. I made my way to my neighbor and retrieved the spare key they kept for me, thanking them for keeping it safe. I had a key to their place for the exact same reason. You never knew what life was going to throw at you, what you couldn?t plan for, and today I was given Peyton. I couldn?t help but wonder where it would lead. Chapter 2 First Dates (1) ?Are you okay, Mister Sweet?? Gayle, my secretary, asked as I came inching into the office. She stood, taking in the bandage on my head. ?When you didn?t call yesterday and now, with that bandage and the way you?re walking, well, are you okay?? What was wrong with the way I was walking? Damn, Peyton?s panties. I had reverently washed them the night before in my bathroom sink, hanging them to dry and when I?d donned them this morning my thought from the day before turned out to be remarkably accurate. They didn?t fit. Peyton was a tiny woman and the panties were just a wisp of fabric. I?d pulled them up my legs, getting an elicit thrill as I did. The same jolt of pleasure I always got from wearing what was deemed forbidden. I settled them against my waist, adjusting my junk in place. Peyton?s panties were tiny, and they did not quite hold all of me in place. I loved them. Partly because they were panties but mostly because they belonged to Peyton and that she had asked me to wear them. Or maybe she had commanded me. I had stood in front of the mirror, turning around to look at the small amount of fabric snaking between my legs. My ass was practically naked. I turned back to the mirror, my cock falling from the panties to hang next to the flash of silky red. I fished myself back into the thong. I turned again, staring at myself in the mirror and then went about getting dressed. My junk had fallen free before I even had my pants on. ?I?m fine, Gayle. Thank you,? I said, feeling the heat rise on my cheeks. Of course, she?d noticed me walking funny. My tiny panties had once again shifted, leaving my junk hanging outside Peyton?s pretty panties. The accident wasn?t the reason my gait was different. Adjusting to Peyton?s panties slicing into my crotch caused that. ?I?m sorry I didn?t get to call yesterday. I lost my phone in the accident.? Gayle rushed towards me like I was an infirm old man about to take a tumble. She reached for me then caught what she was doing. ?Are you sure you?re okay?? ?Really. I?m fine. Just a little sore. I won?t be in long today,? I admitted. ?I have a bunch of things to take care of.? ?You shouldn?t be here now,? she scolded. I shooed her away and made my way to my office. I took a seat and making sure nobody was looking I snaked my hand into my pants and adjusted my panties back in place. That felt so much better than the way the far-too-small panties dug into my scrotum when I slipped free of the fabric. Sitting at my desk, I looked at my open office door. Gayle was sitting just outside. She was a sweet, older woman, probably close to sixty. She?d taken this job a few years ago to get away from her husband who had just retired. ?He?s just always in my way and I?m constantly having to clean up after him. I need a job just to get away from him.? I?d hired her on the spot. I never once thought about what panties Gayle wore. No, that?s not true. I?ve often thought that my panties were probably prettier and today they definitely were. I picked up the phone and made a few phone calls. Enterprise would pick me up, just as their motto proclaimed and it was a far better solution than taking Lyft everwhere. After getting a rental car I?d have to go see my insurance agent and then get a new cell phone. There were a few more people that would need to know about the accident. My parents for one. A few of my employees poked their head in to check on me and I told them all the same thing I?d told Gayle more than once. ?I?m fine. Really.? I guess some of them needed to see it for themselves. Jack, one of my best salesmen stopped in right before Enterprise showed up with my rental. ?Damn, Mason, you are alive.? I laughed, and Jack laughed with me. ?Sorry to disappoint you.? ?Never stopped you before.? ?Good point,? I agreed. ?I?m fine, Jack.? We segued into the next big sale. ?I expect it?ll add quite a bit of work,? Jack said, beaming. That was both good news and bad. More work meant we?d need more employees and while we were a relatively small advertising firm, we seemed to be growing far faster than I could cope with. I?d only added an HR department, a husband and wife teamed named Amber and Clayton, less than nine months earlier. If this growth kept up, I?d need a bigger break than the one I already longed for. Long hours, long days, and long months have a way of catching up with you. ?Better than no work at all,? I said, mostly believing it. I didn?t have time to take the day off but there were too many things I needed to get done. The team could handle it and maybe that was for the best. I was getting burned out. Nineteen employees under me. And thanks to Jack that number was about to climb. Again. ?Good to see you?re okay,? Jack said. ?Thanks.? I left five minutes after the rental car showed up, promising Gayle I?d take good care of myself. I was chauffeured to the rental car counter and thirty minutes later I was on my way to my insurance agent. I was there for an hour, and an hour after that I had a new cell phone. A newer model than the one I?d had before. But it seemed, based on the ads, that there was always a new phone right around the corner. In my business I paid attention to the ads. Some were good. Some bad. Some stupid. I remember one commercial when I was younger that showed a lone man walking along a deserted highway. A pretty woman stopped and asked if those jeans were of a certain brand. He admitted they were. And then she drove away, leaving him alone on the highway. If you?ve seen it, you know how dumb it is, right? If we had done the ad, that man would have gotten into the car with the attractive young woman. I got the point. The jeans, by that manufacturer, made him noticeable but wouldn?t it have been better if not only was he noticed but rewarded? I called my folks and told the about the accident. Mom was concerned about my health; dad about my SUV. I smiled at the dichotomy. Through the day I kept adjusting my crotch. My junk just wouldn?t stay in place inside Peyton?s petite panties. It was one of the reasons I preferred boy shorts and full briefs. They held me in place much better than a thong. It was just after lunch when I started giving serious though about my date. I had far too many questions and no good way to get them answered. I didn?t have Peyton?s number and I didn?t know where she lived. Did she work today? Was I supposed to pick her up from the hospital? Would she really want to go on a date wearing scrubs? Even I knew the answer to that one. No. It was a date. A formal date and she?d want to get dressed up. I needed to get in touch with her. Should I call the hospital? My new phone dinged. I had a text message. My phone may have changed but my number had stayed the same. How do my panties feel? It was Peyton. I plugged her number into my phone. I smiled. She had my number. Of course she did. She?d told me so the day before. I typed back my response. I keep falling out of them. She sent back a smiley emoji. Aww. I know a way to keep that from happening. Oh? You?ll find out. That was followed by a little yellow face sticking out its tongue. What did that mean? She was a mysterious woman full of so many secrets. My phone beeped again. She gave me her address and told me to pick her up at seven. I was smiling as I typed my response. Looking forward to it. Me too. Gotta go. Later, Sweetness. Well, that answered that question. Now, what were we going to do? (2) Once, a long time ago, I took my ex-wife on our first date. At the time I thought that that would be my last first date ever. Turns out I was wrong. Turns out you can?t predict the future no matter what television psychics would have you believe. Although, truth be told, I bet I could write an ad that would make people believe. I had thought that first date with my ex-wife had been perfect. The perfect last first date. My first date with Peyton was somehow much better. Maybe it was the novelty of it; there had been times I thought I would never date again. Before Peyton I wasn?t exactly looking for a new relationship. I wasn?t opposed to one, I just wasn?t seeking one out. Whatever would happen would happen and I would be okay with that. Only I wasn?t just okay with Peyton. I was ecstatic. She was fun and sweet and mysterious. Definitely mysterious. After my accident, she had driven me home from the hospital telling me how much she wanted to see what other naughty things I had in my panty drawer, laughing when I told her during that drive to my house that I did actually have one. Then, once we pulled into my driveway and I invited her in she was the one that told me no, that we hadn?t had our first date yet. She was interesting and complicated, and it was fun trying to figure her out. When I showed up at her door she had nearly taken my breath away. She was wearing a little black dress and it didn?t just fit her. If sculpted her, molding to her alluring body in a way I had been unprepared for. I had only seen her in scrubs and they hid so much that was now being revealed. The dress was low-cut giving a tantalizing view of cleavage. The dress ended just above her knees. She was wearing simple heels with an open toe. Her toes were painted a deep burgundy color. A gold necklace encircled her throat drawing my eye upward just as that small flash of cleavage drew the eye down. ?Wow.? I said and then could say no more. Her hair was coiffed and hung to her shoulders. She wore a simple flower in her hair. I didn?t know if it was a daisy or an orchid and I didn?t much care. Somehow that flower made her even more lovely than I remembered. Peyton smiled. ?You clean up pretty good yourself,? she said. Even wearing a suit, it was obvious she outclassed me. By a lot. ?Thanks. You look amazing.? She beamed at the compliment. I held out my arm. Peyton draped her arm in mine. I led her to the car, suddenly thanking that idiot driver. Without rolling my SUV I would have never met this stunning lady. Funny how things like that can happen, something bad that leads to something much greater. I drove to the restaurant. It wasn?t exactly a five-star restaurant, but it was clean with good food. The lighting was subdued, giving the place more of an adult feel than say a Chili?s or an Applebee?s. Couples were enjoying their meal at some tables while a family of five sat at a booth, the parents sharing a desert while their three children sat quietly, their eyes glued to their phones. We got a seat right way. A young man came up to the table, ?I?m Brad,? he greeted us with a practiced, professional smile. He was wearing black slacks with a white shirt buttoned to the collar and a thin black tie. The same outfit the whole wait-staff wore. ?What would you like to drink? We have a lovely Pino that I could recommend.? ?A glass of your house merlot please,? Peyton told the waiter. ?Very good. And you, sir?? I was driving. ?Half and half tea, please.? Peyton considered what I ordered, seemed to regard it and what it meant. She nodded and then giggled, ?Oh, live a little Mason. Have a cosmopolitan.? I knew what she was doing, and I felt my cheeks flush. My mysterious playful date was being playful. She wanted me to order a drink. A decidedly feminine drink. She was smiling at me, her head tilted to the side. Was I being tested? Probably. Did I enjoy the course? Absolutely. ?On second thought,? I said, playing along with whatever game Peyton was playing, ?I?ll have a Cosmo.? ?Be right back,? our waiter said. ?Oh, I wonder what Brad is thinking,? Peyton asked. ?A big strong man like you ordering such a sweet, girly drink. But you follow orders very well. I do like that.? I smiled. I liked following her orders. And so far, I liked playing her games. We started talking, revealing little things. It was still too early in our relationship, and I did see a relationship forming, to talk about far deeper things. She told me about Louisiana State University where she went to college and I told her about attending college at UCLA and my degree in advertising. I learned more about her family and she learned equally revealing tidbits about mine. Brad was a diligent waiter, filling our drink orders and keeping my tea full following that one embarrassing drink. Peyton had a second glass of wine and then switched to coffee stating, ?I don?t have to get up early.? She made me smile when she added, ?And the night is still young.? We ordered and ate, the conversation flowing easily. There were no long, awkward pauses as we struggled to find a commonality. We talked, one subject merging seamlessly into the next. I learned about her mom and offered a sincere ?I?m sorry,? when she told me more about the brother she almost had. She told me more about her father and how he never started dating after the accident that took her mother?s life. ?He just doesn?t have it in him,? Peyton said. ?It?s too bad, really. He is a great dad and he was a great husband.? ?Did you ever think of setting him up?? Peyton gasped as if I said something blasphemous but then nodded, ?of course, silly.? She shrugged. ?Maybe someday.? ?Would either of you like desert?? Brad refilled my tea and topped of Peyton?s coffee. ?Ooh,? Payton said, her eyes lighting her face, ?What do you have?? He recited the desert menu. Peyton stopped him half way though. ?The cr?me br?l?e. Definitely.? She smiled at me. ?Two spoons.? Brad acknowledged the order and left the table. ?Now,? she giggled. ?Let?s do something naughty.? ?Oh?? ?Go to the little boy?s room and take off your panties. I?ve been wondering all night which ones you?re wearing. Did you pick them out special for me?? ?No,? I admitted. ?I didn?t quite think we?d get that far on a first date.? Peyton laughed, ?Good boy. I?ll do the thinking, remember? Run off now. Before Brad gets back.? I left the table, passing two couples out on a date and a family of four where the twin girls were talking loudly about having far too much homework. I walked past the bar where single men and single women were chatting and drinking. One older man sat there eating a steak and watching Sports Center on the lone television mounted above the bar. In the empty bathroom I entered the handicap stall. I kicked off the shoes I had polished before my date, undid my belt, and slipped off my slacks. I pulled my panties off. During the day I had worn Peyton?s red ones, but I?d changed prior to our date. My current panties were blue, the color of the deepest ocean, with dozens of little pink hearts serving as polka dots. The waistband was made of lace and a simple pink bow sat in the center. I liked them. They were cute. I got dressed and returned to Peyton, my panties hidden in the pocket of my slacks. Peyton was grinning. ?Hand them here.? I handed her my panties. Peyton put them on the table, spreading them out like setting an insect on a cork board. Sitting on the white tablecloth they were impossible to miss. I glanced from the panties to Peyton and back again. My throat seemed to tighten up; my mouth went dry. I picked up my tea, took a sip, paused and took another. Peyton laughed. ?Relax. Brad will think they?re mine and that you?re going to get lucky. But, please,? she let out a throaty rumble, ?keep acting nervous and maybe he?ll figure it out.? She looked towards the ceiling as if deep in thought. ?Maybe he will think they?re yours. You are the one that ordered the girly drink after all.? I took another pull of my tea. She was right. It was possible that Brad would think the panties on the table belonged to the woman at the table. After all, men didn?t wear panties. Ask my ex-wife about that one. But men didn?t order cosmopolitans, either. I place my glass on the tablecloth. My hand was shaking slightly. Brad may think they belonged to Peyton, but she and I knew those panties belonged to me. I couldn?t shake that thought. Brad returned with the cr?me br?l?e. He placed the desert on the table closed to Peyton. I watched him, his eyes darting from my blue panties with little pink hearts, to Peyton and then back to the panties. He glanced at me and then back to Peyton. Peyton was grinning, her eyes glued to me. I was embarrassed and slightly aroused. I could feel the heat on my face and when I reached for my tea my hand was shaking. ?Enjoy,? Brad said walking away after casting another glance at Peyton. Maybe he thought they were hers. Why would he think otherwise? ?It?s eating you up, isn?t it?? I admitted it was. ?Good. Oh, you are so much fun.? With that she picked up the spoon and cracked the caramelized sugar topping to our shared desert. She took the first bite, letting out a soft sound of pleasure. ?Oh, that?s good.? I picked up the second spoon and joined in. The desert was creamy, the hard top deliciously decadent. It was a very good cr?me br?l?e. Brad returned with the check. I reached for it. ?Allow me,? Peyton said. I shook my head. ?Then it wouldn?t be a proper date,? I said. She was right to offer to pay and I was glad she made the attempt even if we both knew going in that I?d be paying for dinner. She was as polite as she was mysterious. ?Thank you,? she said, her dark eyes locked on mine. ?You?re welcome.? We left the restaurant. I opened the car door for Peyton, exactly as I had when we?d left her house. She buckled herself in as I made my way to the driver?s side. I started the car and pulled out of the restaurant. ?Where are we heading?? ?You?ll see,? I said. I could be mysterious, too. ?Oh, goodie, a surprise.? She exclaimed, clapping her hands together in a rapid staccato. She had a playful tone in her voice, like a child opening the biggest birthday present and not believing the present was for them. Once, long ago, I went on my second to last first date with my ex-wife. We had gone to dinner and afterwards I?d taken her bowling. It was silly and childish and fun. A little competition mixed with a lot of laughter. We pulled out of the restaurant and twenty minutes later I was parking in front of a bowling alley boasting ?thirty lanes of fun.? ?I haven?t been bowling in forever.? ?Me either,? I admitted, omitting the fact that I?d taken my ex-wife here long ago. That wasn?t important anyway. I parked and together Peyton and I climbed from the car. She stood, staring at me, her head cocked. ?What?? I asked. ?You know,? she glanced down, ?I?m not exactly dressed for this.? ?Oh, shit,? I hadn?t thought about that. I was so caught up in repeating a perfect first date from so long ago that it never dawned on me that Peyton was wearing a lovely black dress while my ex-wife, Linda, had been wearing slacks and a simple peasant blouse. Peyton laughed, ?I?m so going to kick your ass.? She spun around and started running towards the bowling alley. I sprinted after her, both of us laughing. I caught her just as she reached the front door. ?I win!? She cheered. She stuck her tongue out and then gave me a quick kiss, startling me. I liked being startled with lovely surprises like that. I opened the door for her and loved that she let me. We went into the building. Most of the overhead fluorescents were out; the building was lit with black lights. Neon paint on the walls showed happy anthropomorphic bowling balls stalking equally humanized bowling pins. Overhead, in the middle of the bowling alley, a disco ball was spinning, sending bright points of light to all corners of the building. Music was playing, some upbeat, rhythmic song that I didn?t know but found it to be quite catching. It was a beat you could dance to. I had reserved the lane and even though we were ten minutes early the lane was clear. We got our shoes and our balls and while Peyton was swapping her delicious heels for the bowling shoes and disposable socks I was getting each of us a beer. ?Ready?? Peyton asked, as I returned, a cold bottle of beer for each of us. I smiled, ?yep.? ?What?s the stakes?? Her playful streak was shining through. ?What did you have in mind?? ?Hmm,? she said, tapping her chin with one long, perfectly painted finger. ?How about winner gives the loser a massage.? ?Sounds like I win either way.? She laughed. She rushed towards me, planted a little kiss on the tip of my nose, ?I go first.? I laughed right along with her. Peyton sat at down and plugged our names into the computerized score card. Her name first. For my name she entered Sweetness. The song changed into one I?d heard, asking what a fox says. It, like the song before was catchy and upbeat. The lights above the disco ball changed colors, now reds and blues and greens were spinning over the lanes and the ceiling and the walls. On either side of us couples and singles and families continued their own games, each of them lost in their own oasis just as Peyton and I were. I took a sip of my beer and watched at Peyton sashayed up to our lane. She picked up the ball, waggled her lovely behind at me, drawing my attention to the shape of her legs, the swell of her hips and the softness of her ass. It was a delightful weapon in her arsenal for sure. Peyton brought the ball up, her arms folded towards her chest. She concentrated, staring down the lane. The disco lights bounced off her arms and back and hair. She took the first step forward, her arm dropping. Another step and the ball continued falling backwards. A third step found the ball moving forward, fast, faster, almost a blur. The fourth step and the ball slipped from her hands. It spun towards the gutter and curved just before dipping into oblivion. It spun towards the pins, striking just to the left of the head pin. The sound was loud as eight pins toppled. She turned towards me, her brown eyes big, those lips that had already given two gentle kisses pulled upward with a joyous smile. I was nodding. ?I?m in trouble.? She shrugged. ?Maybe.? She blew me a kiss while waiting for her ball to return. She picked it up and focused again. She threw the ball and made the spare. ?Definitely in trouble.? We passed each other next to the scoring table. She ran one finger along my hand, giving me chills. I picked up my ball, glanced at the pins, back to Peyton, and to the pins again. Peyton had hooked her ball into the pins, I tended to throw my ball straight. My ball hit to the right of the foremost pin, somehow taking out a total of five. My second throw went exactly where the first one went, only this time the ball hit nothing but air. I have five points; Peyton was sitting on a spare. ?Hmm, now what should I get for winning the frame?? Peyton asked, toying with me. ?So, we?re playing frame by frame, are we?? She shrugged, took a sip of her beer, and took my hand briefly before passing me towards the elevated lane. There were a lot of little touches as we played. We held hands, had two chaste kisses, and one long swaying hug through a John Cougar Mellencamp song that we both loved. We smiled. We laughed. We touched. At the end, I won one game and Peyton won two. Years earlier I?d beaten Linda three games to none. The joyous look of victory on Peyton?s face was a pleasure to behold. She didn?t gloat, but she did let me know how much she was looking forward to her massage. I told her that I was looking forward to it as well. ?I bet you are.? We left the bowling alley, once again Peyton letting me get the door for her. I knew her to be a strong, powerful woman so her allowing me to be chivalrous told me everything I needed to know about the strength of her character. ?That was fun, thank you,? Peyton said as I climbed in the car. ?It was. And you?re welcome.? I put my rental car in gear and started driving. Peyton was quiet, staring out the side window. When she spoke her voice was low, muffled by her hanging head and by the seriousness of her words. ?You?re not going to cheat on me, are you?? There was a sadness in her words. I could hear a long-ago heartbreak rising to the surface like a horrible monster about to wreak havoc on some innocent fishing village. She was looking away, as if she couldn?t face me, too afraid of the answer I might give. I felt my heart ache a little. She sounded small and insecure, hurt and both scared and scarred. Someone, long before me, had hurt her and that pain still stung. I glanced at her as she rested her head on the passenger side window. ?No,? I said. I pulled into a parking space next to a closed furniture store. Peyton?s words and tone let me know that this conversation was important and needed more attention than I could give while driving. I parked the car, turned off the headlights, and turned to face her. I took the hand closest to me. She flinched but didn?t pull away. ?I?m not like that,? I said. ?I?ve never been like that.? Peyton sat up. She faced me. Her eyes were damp. She wasn?t crying but it was close. ?I really had a good time and you?ve been good to me. Good for me. I?ve been...? ?He cheated on you?? She nodded. ?With my best friend. Two for the price of one,? she tried to smile and failed. I knew what she meant. She lost her friend and her boyfriend in on fail swoop. I thought of Linda and how it would have felt if she?d have cheated on me. I couldn?t imagine a worse feeling and by the sadness in Peyton?s words and the tone of her quivering voice I knew she had felt what I could not imagine. I rubbed the top of her hand with my thumb. She was facing me now but still out of reach. ?I would never ever do that,? I said. ?Ever.? ?Promise.? ?I promise.? Her lips lifted in a smile but faded away. ?Sorry. It?s just.? ?I know.? ?No. No you don?t. It wasn?t just that he cheated on me or who it was with it was that he didn?t even try and deny it. I caught them. I was supposed to take a shift for another nurse because her son had been arrested. Drugs,? she shrugged. ?She showed up for work right on time and I was surprised to see her. ?What happened?? I had asked. I still remember her saying how it was probably best that her son spent the night in jail. ?Maybe he?ll learn something.? She?d said that like she didn?t exactly believe it. ?So, I left after my scheduled shift. When I got home they were, well,? she gave a defeated shrug, ?on the same kitchen counter where I?d cooked dinner so many nights. Jason, my ex, looked at me, grinning, while Kathy, looked away embarrassed. Jason reached out and said, ?join us.? He didn?t stop what he was doing. Neither of them did. There wasn?t any shame on his face. He didn?t feel guilty or if he did it didn?t look like it to me.? I stayed quiet. Letting her speak. The sad look on her face was replaced with something primal. It wasn?t exactly anger but that was there, too. It was something stronger than that. Rage maybe. Tinged with shame. ?I turned around and was gone a moment later. Jason never came running out. Kathy tried calling me later, but I didn?t answer. I haven?t talked to her since.? She sighed, finally pulling her hand from mine. ?If you?re going to cheat on me...? The rest hung in the air, weighing on both of us. ?I won?t. I?m a one- woman man. Honest.? I don?t know if she believed me, but I knew she would in time. I?d never cheated on Linda. The thought had never entered my mind. ?Okay.? She considered what I said and then perked up slightly. ?Okay,? she repeated a little bit stronger. A smile returned to her face. ?You owe me a massage and I am dying to see your panty collection and those heels you told me about.? She paused in thought. ?Can you take me home? I have plans tomorrow. How about you show me your collection Monday after work?? I took her home. We talked during the drive about television shows we liked and our favorite singers. The conversation was light and while it wasn?t strained there was the specter of Peyton?s worries clouding what we said. She grew more animated and was giving honest smiles by the time I kissed her goodnight. This kiss wasn?t the coy, playful kisses we?d given each other while bowling. There was true emotion behind this kiss. One that had Peyton saying I?m holding to your promise while mine saying I won?t let you down. It was honest, sweet, and inquisitive, hinting at what could be. It took my breath away. ?Good night,? she said. ?Good night.? She stood at her front door until I backed out of her driveway. I waved, and she waved back. I was smiling into my rear-view mirror as Peyton shut the door. Once long ago I took Linda on our first date and I had thought that that date was perfect. The one with Peyton, my truly last first date, went so much better. Not just because of who she was but because of the vulnerability she?d revealed in telling me about her final heartbreak. She?d intrigued me when she revealed she knew my secret. She enamored me by telling me hers. Monday couldn?t get her soon enough. Chapter 3 Fashion Fun I handed my new iPhone to Peyton. ?When I tell you to, hit play.? Peyton was sitting in my leather recliner, one leg crossed over the other. She had one shoe dangling freely; she could wiggle her toes and the sneaker would fall to the ground. She glanced at the phone. ?What are you up to?? ?You?ll see. Hit play when I tell you.? ?Okay.? I walked through the kitchen, turned left and dashed into my bedroom. I kicked off my shoes, doffed my pants and took off my tie. I had a simple beef roast simmering in the crock pot, but before we ate it was time for some fun. I?d had an idea on how to satisfy Peyton?s request to see my panties and it was time to put that plan into motion. The yellows ones were first because, of course, they had to be. They were the ones that started it all. Peyton was sitting in my favorite recliner, the one I used to sit in every night after my ex-wife had moved out. The one I?d sit in and ponder exactly how I wound up sitting alone, with my marriage not just falling apart but crumbling. The one that would support my weight but couldn?t exactly support the weight of my thoughts. ?Hit play,? I called from the kitchen, just out of view. The music started. Bob Segar started to wail about taking old records off the shelf. I darted into the living room and slid across the floor, miming Tom Cruise from one of his earlier movies, the one where he dated a prostitute. I was wearing a white, button down dress shirt and the same yellow panties Peyton had already seen. The ones that had made her say, ?Yellow. Nice.? The one that had started it all. They were soft and lacy, the back a thin, sheer material almost like an overused coffee filter. Peyton made an amused snort, set her wine glass on the coffee table, and then began to applaud. ?Shake it, mister. Shake it!? And I shook it. I waggled my pantied ass towards her, shaking my hips. It wasn?t exactly twerking, I didn?t have the coordination for that, but it was close. Peyton was laughing and hooting while I sashayed from one side of the living room to the other. ?Here we have Mason wearing a saucy yellow number,? I said, unbuttoning my shirt before tossing it aside, ?straight out of a Lane Bryant catalogue. Notice the wide hips and the full seat. The perfect accent for a warm spring day.? Peyton snorted. In all the years I?ve been on this earth I had never in my life seen a woman having so much fun. Hell, I didn?t know it was possible for anyone to feel as much joy as she seemed to portray and seeing it made me feel the most masculine I?d ever felt. And I was wearing panties. I found that fascinating. Peyton was still laughing as I left the living room. Bob Segar quit wailing about that old-time rock and roll. Once out of view I dashed to the bedroom and quickly pulled off the yellow panties that Peyton had first seen and donned a new pair. They were a pale purple, solid in the front with thin strips of lace across my behind. A darker purple band encircled my waist and three thin strands of purple ribbon made a lattice across my upper butt. I slipped the purple panties on and rushed back into the living room. ?Now Mason is wearing a delicate purple number. Notice how the stands of ribbon in the back seems to accentuate our model?s butt crack. The little bow on the front emphasizes just how feminine these panties are.? Peyton laughed again, leaning forward in the recliner to get a better look. I marched back and forth in front of her. A panty model on an imaginary runway. ?Very nice,? she applauded. That was followed up by a loud cheer. Another song started, and Peyton turned it off. My silly introduction no longer needing a running music track. Smiling, I left the room and returned a moment later in the next pair. They were soft and pink with dozens of little white polka dots. I described them in that same faux announcer voice as I traipsed back and forth in front of Peyton. She was laughing and smiling and hooting and hollering, having more fun that I?d ever imagined anyone ever having. The pink polka-dotted pair was replaced by a light gray pair with black lace trim. Those were followed by a pair of red panties that had purple flowers tatted into the lace. The pastels came next. The aquamarine followed by the teal, the pink followed another light-colored pair that wasn?t quite orange but was close to it. I paraded myself in front of her in every pair of panties I owned. Solid black with lace trim gave way to another black pair of panties that were decorated with light pink hearts sewn in the lace across the back. Green ones trimmed with a florescent orange waistband came next followed by a pair of light blue boy short panties with a neon green bow sewn into the front. I kept going, swapping out one pair after the other. More pinks came, one light pink with a white bow on each hip that led to another pink pair with purple orchids printed on the lace. A neon pink pair with purple bows followed two pairs, both black, one with gray trim and the other with a silver lightning bolt stitched onto the front. ?Mason is now wearing his Super Heroine panties,? I joked in that same announcer voice, standing in front of Peyton with my hands on my hips, my crotch and its silver lightning bolt thrust forward, and my head turned to the side. It was the classic super hero pose made ridiculous by what I was wearing. Peyton had tears in her eyes from laughing so hard. Still I kept going. I went through a few more pairs of panties, finally ending on a pair of simple black panties. They were bikini panties with a full back. They were solid black with a light tatting of lace around the waist. A simple black bow decorated the front. ?Finally, Mason is modeling the first pair of panties he ever bought.? ?Oh,? she said. ?Are those special?? I paced back and forth, finally ending my panty parade by sitting on the arm of the recliner next to her. ?They were the first ones I ever bought myself and I still have them, so I guess they are.? ?Where?d you get them?? ?Walmart. The one by the house has these self-checkout lanes. I was there getting some supplies to change the oil in my car. I?m walking out of the automotive section and I?m drawn to the panty section. I wasn?t there to buy any; I hadn?t planned on it at all. Still, I found myself walking past bras and panties and without really thinking I grab these and put them in the cart. They were in my size; the tag had shown me that. I remember shaking like I was doing something illegal. I moved those plastic jars of oil around to kind of squash the panties. To hide them. I looked around, that same guilty behavior I couldn?t hide if I wanted to. Still, I made it to the check out lines and rang up these panties. I finished with the oil and filter, putting them on top of my panties. ?I was surprised that nobody stopped me as I was leaving the store. I shouldn?t have been, but I just felt so guilty.? Peyton put her hand on my arm. She moved upward and kissed my cheek. I smiled. ?I made it home and left a trail of clothes from the front door to my bathroom. I put the panties on and stood in front of the mirror, turning from side to side. I spun around and stared at my reflection. They were boring, but they were new. I?d kept a few pairs of Linda?s, so that was about the extent of my collection so having some new ones that were exclusively mine made them, I don?t know, more exciting maybe.? She made a cooing sort of noise that was half understanding and half amusement. She had this look on her face that I had not seen in a long time. It was one of longing and need tinged with excitement. Her brown eyes were wide and looking up at me, her head tilted, her mouth slightly parted. I leaned into her and she inched towards me. I paused, my mouth nearly meeting hers, and held there, the time dragging on into forever. I felt her hands sitting on my thigh. I felt my mouth curve up into a smile. I felt her fingers digging into my skin. I moved that last tiny bit. My mouth met hers. We?d had chaste kisses and little nips on the cheek and nose but that kiss, that first real kiss that was far greater than the good night kiss after our first real date, released an eruption of emotion. It made up for the loss of Linda; it made the last two dates with Peyton a promise of what was to come. Our tongues met, darting and dancing, both playful and needy. Her hands rose higher, sliding across my panties. They moved higher still, along my stomach and then higher still. Her fingers slid along my throat, running through my hair. She pulled me towards her, falling backwards, that one shoe finally falling free. I fell forward, shifting my own hands under her scrubs. Her back arched, telling me without words, that it was okay to continue. I felt the heat of her skin in my palms. My fingers reached her bra and the hidden swell of her breasts. She kissed me harder, her hands pulling my hair hard enough to sting. She kissed me, and I kissed her back with that same molten ferocity. My hands slipped under her bra. I felt the hardened nubs of her nipples grow even harder. She moaned into my mouth. Her hands sidled lower, sliding along my naked chest. I felt her hips shake as she pushed her scrubs lower, revealing her own panties. I glanced downward. I couldn?t help myself. She was wearing a simple thong. ?Blue. Nice.? She giggled before working her panties off her hips. Her hands rose then, returning to my hair. She pushed me lower, indication her desires and I went where she directed. In all the many years we?ve been together, Peyton had never once been shy about defining her needs and that first time was no different. She pushed my head lower, past her chin, over her breast. She pushed me lower still, her legs flailing to work her scrubs and panties free. One leg fell to the ground to land next to her shoe. I went where she led, my kisses following where her determined hands commanded my head to go. My tongue trailed where she directed. She gave a little gasp, her fingers digging into my scalp, when I reached her destination. Later, both of us sated, and our breathing finally back to normal, Peyton sat up and said, ?Now, you said something about heels?? I laughed. I looked into her eyes, at her smudged make-up and disheveled hair. I looked at the faint smile toying with the corners of her mouth. There was a playfulness on her face and something more. Something primal. Had the thought of my heels led to what we?d just done or was that just a continuation of the fashion parade I?d started an hour earlier. And what did it matter. I was smitten, as was Peyton, and we both knew it. ?I did.? ?I wanna see.? I stood up, fishing myself back into my small, black panties. That first pair I?d ever bought on my own. Earlier pairs were stolen from my mother and from my best friends? sister when I?d discovered them in a dirty clothes hamper. They?d been forbidden so they?d been exciting but not as exciting as the first pair I?d bought on my own. I made my way into the kitchen, grabbed a glass of water for both Peyton and I, before returning to her side. I gave her a glass. ?Be right back.? ?Yeah!? She took a long pull of water. ?Thanks.? I smiled and left the room. I owned two pairs of heels. One black and one red. Like most of the things I owned I bought them online. Lane Bryant, Victoria?s Secret, Fredricks of Hollywood. Panties were easy. Once I knew my size I could order with ease. My heels were different. I?d never bought them in person and a man?s shoe is sized different than a woman?s. Online research told me to order them about two sizes bigger and that was a good rule-of-thumb. Both pairs I owned with a size twelve; my own shoes a ten. I had owned about six pairs of heels in my life. The first two didn?t fit. Online ordering was a crapshoot at best, but they did help me focus in on a size that does work. The next two did fit but of course guilt and denial and anger and too many other emotions to catalogue caused me to throw them away no matter how much I liked them. I?d been younger and maybe that was partly to blame for purging my desires. Linda didn?t help. The first time she had found my heels she?d been livid. ?Seriously, Mason!? I heard her shout from the garage. ?Are you kidding me?? I recognized the tone in her voice. The anger, rage, hatred and disgust rolled into one vitriolic screech. I went to see what the commotion was, but I knew before reaching her side. In the beginning of our end only one thing brought that acerbic tone. At the end I heard that same tone in every spoken sentence. ?What?? ?Heels. What are you? Some sort of sissy?? She followed that with a burst of disgust. The first heel hit my chest, the second landed just an inch shy of my feet. She had thrown them at me and that fight led me to throw them away. Once Linda left I?d ordered the two pair of heels I still had. The black ones were made of a shiny patent leather with a small two-inch block heel. They were a little plain, but they were comfortable and steady. The red ones were sluttier by far with three thin straps that snaked over my foot to attack to three golden buckles on the side. The red ones had a four-inch heel. I used to wear them a lot. The day they had arrived I?d almost broken my ankle when my foot slid into the groove of my kitchen tiles. I?ve had plenty of practice since. I get an elicit thrill whenever I wear them. More so than the panties. My panties calm me; my heels excite me. I put the red ones on first. They were the sluttiest ones. They?d likely impress Peyton the most and I fond I wanted to impress her. I wanted to make her happy. I wanted to give her joy I?d seen during the panty parade. Somehow, seeing how happy she?d been had put a smile on my face bigger than I could recall ever wearing. Her happiness somehow magnified my own. Had that ever happened with Linda? Maybe at the beginning but I was younger then and the past has a way of being overwritten by the present. Maybe I?d felt happiness making Linda happy. Maybe. But I know for sure that it had been that way with Peyton and I wanted to do it again. And again. And again. Was I already planning on a future? As I strapped the heels to my feet it felt that I was. I came into the living room. Peyton was sitting naked on the couch now, craning her neck towards the clip-clopping sounds of my heels. I walked with ease into the living room, my eyes glued to hers. I was looking for a smile and I wasn?t disappointed. It felt amazing sharing my fetishes with someone who wanted to experience them. With someone who wasn?t revolted by them. Maybe that was why I wanted to make Peyton happy. I?m sure it was more than that. Acceptance trumping fear and loneliness was part of it but there was more. Peyton applauded, leaning forward. ?Oh my God, Sweetness,? she said, ?I can?t believe you can walk in those things. I love them.? And her smile grew bigger and that supportive affirmation caused my own face to brighten in a smile. It felt good to be applauded and accepted and that fueled a confidence that I?d been lacking. With Linda I had had to hide a part of who I was. With Peyton I could truly be me. Maybe that was what made me want to please her most of all. I strutted in front of her with an exaggerated sway to my hips. Another stroll down an imagined runway. Peyton stopped me as I stooled by and pulled me on top of her again. Her hands went to places that for far too long only my hands had been. She guided me where she wanted me to go. We kissed and caressed. Peyton giggled, ?just like a porn star keeping her heels on.? Her giggling escalated to full blown laughter but that didn?t stop either of us from stopping what she had started. Winded and sated, I sat next to her on the couch. She was naked; I was in my heels. ?I love them,? she repeated. ?Now, go show me the other pair.? I wasn?t sure if she meant it as an order. Was she in control of this night, or was I? I had planned the fashion show but since then she had been directing the evening. I found that I wanted her to be. I stood up and she playfully swatted my behind. I made my way to the bedroom, my heels tapping out a rhythm on the tile floor. I?ve always liked that sound. In the bedroom I swapped the red heels for the lower, simpler black ones. They fit well, even better than the red ones. I returned to Peyton?s side. The smile on her face grew impossibly huge as she saw them. ?Oh, they?re perfect.? She was thinking about something. I could almost see the gears turning. ?You like?? She nodded, her eyes glued to my feet. My eyes were glued on hers. ?You have got to wear them to work.? ?Uh, no.? Yet why did the idea excite me? Terrify me, but excite me, too. ?You have to. They?re perfect,? she repeated. ?They?re definitely women?s shoes but the heel isn?t that big, and I bet you can get away with it.? I shook my head. ?I don?t think it?s a good...? She stopped me almost as soon as I started. ?Right. I do the thinking, remember,? she giggled. ?Come on, Mason, it?ll be great. I bet,? she paused, ?yes, let?s make it a bet.? She liked her wagers. I?d already paid off the massage. What would I have to pay this time? Her eyes were wide and bright and full of mischief. I should have said no but I didn?t want to. I wanted to wear them to work. For me or because Peyton wanted me to - I couldn?t say. ?What?s the bet?? I must admit I?ve thought of doing it before. Almost did once or twice but I?ve always chickened out. Maybe I was the sissy Linda thought I was. She considered my question. ?For every day you wear them to work and don?t get caught, I get to decide what you wear to work the next day. Oh, how long until you?re wearing a blouse.? She giggled at the thought. ?Or a skirt.? ?I don?t own any blouses,? I said. I ignored the skirt comment. That thought was far too frightening. And exciting. ?You will.? Just the thought of it gave me chills. ?And when I?m caught.? And why wasn?t I trying to dissuade her? ?We?ll go panty shopping and buy enough pairs for the both of us. We can wear matching panties every single day.? ?We should do that anyway.? Peyton smiled. I should have said no. I wanted to say no. But the smile on her face and the mischievous glean in her eyes convinced me otherwise. ?Oh, hell. Why not. It?s a bet.? She was on top of me a second later. I was far to tired to respond but even when the down below wasn?t working there were other parts that were. Hands and fingers, lips and tongue. Afterwards, lying on the couch with Peyton lying on top of me, her head resting against my shoulder she whispered, ?I?m glad I met you.? I kissed the top of her head in response. ?Can I use your toothbrush?? With that simple question I knew that Peyton was going to spend the night. I kissed the top of her head again. She pushed off me. ?Come on. Let?s go to bed.? I went to bed with Peyton lying naked next to me. It didn?t take her long to fall asleep. I was too wound up worrying about our bet and somehow looking forward to the challenge. Work had become something of an obstacle lately. It was challenging, and I was very well off, but it seemed I was paying for my success by not really living my life. I typically rose early, went to work, and left long after everyone else. I let work consume me during my divorce, distracting me from that failure, and somehow, I hadn?t tried to let work go after Linda was no more. It would be a challenge getting through the day in my simple two- inch heels, but it would be a fun challenge. Maybe it would make work seem a little less intrusive. And I was the boss, would anyone call me out on what I was wearing anyway? I thought of that movie with Tim Robbins and Morgan Freeman. The Shawshank Redemption. Tim Robbins wore the wardens? shoes back to his cell after cooking the books late one night. ?I mean, seriously,? Red, the character played by Morgan Freeman, narrated, ?how often do you really look at another man?s shoes?? That was the final thought I took to bed that night. Chapter 4 ?You?re not going to cheat on me, are you?? Peyton sat in the breakfast nook sipping on a cup of coffee. She was dressed in the same scrubs she had worn the night before. I was dressed in a navy suit, a paisley tie colored with purple and pink swirls over a white dress shirt. I had my blazer on; I looked professional. Save for the simple black heels on my feet. I was wearing the panties that Peyton had worn the day before and the thought that she was naked under her scrubs was a tad distracting and as I paced in front of Peyton, my heels making that lovely sound, I needed the distraction. Was I really going through with it? Was I really going to wear a pair of women?s shoes to work? It seemed I was. Peyton took another sip of her coffee. Her smile was gigantic. ?You?re cute when you?re nervous.? And I was nervous. Probably more than nervous. I?d fallen asleep worrying about going to work wearing my heels and now it seemed I really was going to do it. Was I crazy? Maybe. I?d played a few games with my heels. The day they arrived in their box wrapped with plain brown paper, I had put them on and walked in them, enjoying the clip, clop, clipping sound the heels, my heels, made against the tile floor in my kitchen. I had walked all around my house and wearing them and a pair or shorts I?d foolishly stepped out onto my front porch as if daring anyone to be right outside. That had been frightening. I once wore them an entire weekend, taking them off only long enough to shower. Research and an empty credit card let me find other toys. My shoe locks. Those are fun. The shoe locks are nothing more than a locking ankle cuff with an additional locking strap that runs down, underneath a heel, before returning to lock to the cuff that is affixed to your ankle. The first time I locked the shoes onto my feet I?d spent ten full minutes trying to defeat the lock. Only once had I been able to escape the shoe locks and that was because I hadn?t set the strap that ran under the heel as tight as it could go. The tighter the strap the more secure they became and with the strap pulled taut they were escape proof. That led to a few fun games with the keys to the locks. I?d put them in my mailbox at the end of the driveway and then locked the shoes to my feet. I was stuck without the keys and could only get the keys long after the sun set if I didn?t want to risk exposure. Wearing them because I wanted to was less fun then when I had to. The forced fantasies that played out in my mind always fueled my libido and more than once I?d have to pleasure myself because of my heels. ?What are you thinking?? I looked up at Peyton who was eyeing me, one hand toying with the lip of her coffee cup. Her eyes were wide and interested, her head tilted and her mouth slightly parted. I lifted a foot. ?What do you think?? She giggled. ?It?ll be fine. What?s the worst that can happen?? That led me to think about all the ways I could be discovered, how any of my employees could see and comment on my shoes. ?Are those heels,? or, ?Are those women?s shoes, Mason,? or, even worse, ?what a sissy.? My mind wandered even further. What if nobody said anything? What would Peyton make me wear next as I paid off the silly bet I?d made the night before? She had joked about wearing blouses and skirts but what if those weren?t jokes? I tried to swallow but my mouth was dry. ?Mason?? I admitted my fears. Peyton stood up, leaving her coffee behind, to give me a hug. ?It?ll be fine,? she said in a way that made me almost believe her. There was a confidence in her tone and warm compassion as well. ?I know. But if you are really that scared then it?s okay. You don?t have to. It?s supposed to be fun.? I considered that. To be honest, I?d often considered it. Once, about six months earlier, I?d taken the keys to the locks I used to trap my heels on my feet to the office. I was going to leave the keys in my desk and lock my heels onto my feet the next morning. I?d have to brave the office to unlock my heels. Just the idea had been enough to fuel my fist into furious motion against the most obviously aroused part of me. The simple thought of not only wearing my heels to the office but being forced too had been too much and I?d been unable to control myself. Afterwards, lying spent in my bed, I changed my mind. Still, it was an exciting thought that I?d had more than once and while I didn?t want to wear my heels to work, I wanted to as well and, maybe more importantly, Peyton wanted me to. I hugged her back and when she smiled up at me, I kissed her. ?I?ll be fine,? I said almost repeating her words. ?It?s just scary.? ?I know. I wore,? she paused, pulling away from me to return to her coffee. She took a sip, smacked her lips, took another pull, ?stuff to work, too. It?s scary but exciting.? She had my attention. ?Oh?? She smiled, flashing a coy look that said, ?a girl has her secrets.? Just when I thought she wasn?t going to tell me, she spun to face me, leaning against the small breakfast nook table as I stood at the island in my two-inch heels. ?Toys. Work can get boring, you know.? I nodded. ?Most of the time my job in crazy boring. Most of my patients are nice but they?re not exactly at their best. I?ve been yelled at, cussed at, spit at. Hell, one time an old man threw a full urinal bottle at me just because I pronounced his last name wrong. My job is important, sometimes disastrously so, but mostly it?s a boring routine. Take readings from a machine and write it in a chart; bring a patient a clean pillow case because they spilled something; help a patient go to the bathroom or empty their bedpan if they can?t get out of bed.? She shrugged, and I understood. We all had things we did that weren?t exciting. ?So sometimes I like to liven things up.? She smiled. ?I can?t tell you how many times I?ve worn my ben-wa balls to work. Do you know what those are?? I nodded. ?I thought as much,? she smiled again as if sharing a secret. ?The feelings I get as those little orbs dance around inside my pussy is electric but it?s even more so because I?m doing it at work where the naughty is somehow even more exciting.? The smile faded from her lips, but her eyes remained wide. ?I?ve worn my vibrator to work a gazillion times. Once, just to see what it was like, I turned it on and had it buzzing away while I did my rounds. God,? she let out a sharp burst of air, ?I could only keep it on for about twenty minutes before I had to turn it off. It was intense. That led me to always try to outdo myself. I?ve made it a rule that every time I wear my vibrator to work, I must turn it on for a longer period of time than the time before. I?m almost up to an hour and a half. God, you have no idea how wet that gets me. It?s so hard. The clock doesn?t stop just because I come and let me tell you, when you?re that sensitive and the vibrations keep going, it almost becomes painful.? She shrugged, ?I get it is all.? I believed her. I nodded, my mouth open, ?I...? ?What?? ?My heels. The other pair. I did something similar, no not similar, the exact same thing. When I got them, I couldn?t exactly walk in them. I hobbled at best.? Peyton nodded but didn?t interrupt. ?So, I made a game out of them. Every time I put them on, I?d have to wear them longer than the time before. Fifteen minutes because half an hour, became an hour, became two. I forced myself to get tons and tons of practice because of that silly, self-appointed rule.? ?Exactly.? ?I learned to walk in them because I made that silly, not rule I guess, but contest. Just to see if I could outdo myself.? Peyton was nodding. ?Exactly,? she repeated. Then she kissed me, a quick little peck on the lips. ?Now, I have to get to work.? She spun away and stepped towards her coffee. She took one last sip, put the cup in the kitchen sink, and then gave me another quick peck, this time on the nose. ?I?m having some friends over for dinner tonight. Dinner tomorrow?? ?Okay.? I flashed her a smile. She smiled in return. ?Great.? She left the kitchen, pausing at the front door just long enough to drop her scrubs and flash me a view of her pantiless behind. A quick tug of her scrubs and she was covered once more. With that she was gone. I washed our coffee cups, setting them aside to dry. Ready for work I made my way to the front door. My heels made that enticing clip- clopping sound, reminding me with every step exactly what was on my feet. I looked down, shaking my head, suddenly terrified to open my front door. How was I going to do this? Peyton and I both wanted me to but wanting and succeeding were two totally different things. If I was this afraid to leave my house, how was I going to walk into my office? I reached for the doorknob. My hand paused, too afraid to twist. I scolded myself. I imagined Peyton encouraging me, telling me that it would be fine. I spun the knob and opened the door. Outside I saw two kids waiting for their bus about forty yards away. Were they too far away to notice my shoes? Would they even glance my way or were they too absorbed in their adolescent lives? I took a step, another, and locked the door behind me. ?I can do this,? I whispered, feeling my heart thrumming in my chest. Feeling the arid desert that was my mouth. Feeling my testicles tighten. I heard a dog bark, I felt a cool breeze against my clammy neck. Everything seemed far too alive. Far too vivid. I?d been outside my house in my heels before and that had been fun, so why was I so terrified now? That one was simple. I?d never worn my heels to work. I inched towards my SUV. The sooner I got to work, the better. I was typically the first one there. I could race to work and hide in my office and no one would have to know what delicious secret I was hiding. That thought, turning it into a game, made it a bit easier, a bit less impossible. I made it to the SUV and then without another thought I made it to the office. That was easy. Nobody could see into my car but once I stepped onto the pavement, my heels would be visible to anyone who glanced my way. I sat in my car, staring at my office building. Glancing around, my hands toying with the steering wheel, I looked for anyone. The parking lot was empty. That was a plus. I can do this, I thought. I opened the door and closed it again. I can?t do this, a stronger thought followed. I pulled my foot up and undid the little golden buckle. ?You?re not going to cheat on me,? I heard Peyton?s sad question. The one she?d asked after she?d beat me two games out of three. I stared at my hands. She had meant it in a different way, but wouldn?t I be cheating if I walked into my office wearing only my socks on my feet? And since it was her idea, then wouldn?t I be cheating on her? I had promised her I wouldn?t, that it wasn?t who I was as a man. I?d meant it the way Peyton had meant it but somehow that promise seemed to solidify my resolve. ?I can do this.? I opened the door and stepped onto the rocky pavement. I took a step. Another. I heard my car chirp as I locked the doors and set the alarm. ?I can do this,? I said again. I liked my lips, feeling their dry surface every bit as rough as the concrete under my heels. I clip-clop-clipped towards my office suddenly loving and hating the sound at the exact same time. I could hear it and if I could than anyone nearby could too, and wouldn?t that make them look? I know I would. I shuffle-walked after that, masking the sound of my heels by sliding them against the ground. I moved at a slow, hindered pace toward the front door. As expected, I was the first one there. The empty parking lot had told me that but with the shoes on my feet I was still somehow worried that I would be discovered. Satisfied that I was first, I easily unlocked the door and made it unhindered to my office. My heart was racing. I was scared and excited. The forbidden was delicious. I looked at my heels hiding under my desk, feeling an elevated sense of triumph and an electric current of arousal. This was fun. Scary, yes, but fun too. The easy part was done. What would the rest of the day bring? ?Good morning,? Gayle said as she came in. ?Feeling any better?? ?I didn?t feel bad the last time you asked,? I said, smiling at her motherly tone. I glanced at my heels. Did she see them? Did she know? If she did, she gave no indication. ?Good. I?m glad you?re okay.? ?Me too.? I moved my feet away from Gayle, as if those extra few inches would keep my feet hidden. Would I be doing that all day and why did I find the idea so appealing? Gayle left my office and I got to work. I answered emails and thought of my heels. I took phone calls and felt the heels on my feet. Gayle came and went, and I kept my heels hidden. Suddenly I had to pee. My office did not have an attached bathroom. How was I going to leave the office in my heels knowing the sound they made? I couldn?t do it. I just couldn?t. I sat at my desk, trying to get some work done, feeling the rising need to pee fighting with the terror of wearing my heels out of my office and amongst my employees. Hiding in my office was easy; facing others would be much harder. I answered another email, another, a third. My heels slid across the floor as chills raced along my arms. The need to pee was winning. I brought my right heel to my lap, fear making me reach for the buckle. I undid one strap and pulled the shoe from my foot. I paused at the second one, suddenly feeling like I was betraying Peyton. ?Shit.? I put the shoe back on and buckled it again. I stood and walked across the room. I opened the door and walked past Gayle. With my back to her I couldn?t tell if she could see my heels. She had to see them, right? We worked together five days a week, occasionally six, so I was certain that she?d see something about me was different. My gait, my height, the low noise my heels made as I shuffled as quickly as I could, dragging my feet, trying to hide that enticing sound I loved so much. Would she notice and if she did would she say anything? I made it to the bathroom and did what needed to be done, staring past Peyton?s panties and down to my shoes as I did. My pants hid most of them so maybe Gayle hadn?t noticed. I took some solace in how much the hem of my pants concealed my shoes. I returned to the office happy that Gayle barely gave me a glance. It was a boring day made exciting by my heels. The hours that normally crawled by seemed to have the liquid speed of river rapids. Lunch time came, and I ordered a salad for Gayle and a Philly cheesesteak for me. Gayle left after I placed the order and brought my lunch to me. It was a routine we?ve practiced far too often. Today, hiding my shoes, it was a welcome routine. Gayle left at the end of the day and as the office emptied, I felt a huge wave of terror, relief and amazement. I was both relieved and amazed that I?d made it through the day without anyone commenting on my heels despite wearing them all day, even going to the bathroom a total of three times. I was equally astounded at how quick the day seemed to pass. Normally my day was filled with tedium and a rising sense that it was time to try something new. I made a good living, very good actually, but lately it had seemed that the rewards didn?t even come close to compensate for what I paid in stress and time, but today, with my heels hiding on my feet, the day hadn?t been cloying or oppressive but fun. The terror came from what Peyton would dream up next. Why had I made that bet? As I was leaving the office my phone chirped. How did your day go? I responded to Peyton?s text by sending back a smiley face. Did anyone say anything? No. She sent back a picture of two hands clapping followed by a little yellow face sticking out a big pink tongue. Told you. Back in my car my phone chirped again. Wear them again tomorrow. You knew that was coming, right? I did. I did. The applause emoji came again. Can?t wait to hear all about it. Shit, my friends are here. I laughed at that. I could picture her getting ready for her guests and cussing because they were interrupting our conversation. Good night. Night. I went home, made dinner and relaxed on the couch, bouncing between ESPN and reruns of Family Feud. I still had my heels on and my distracted eyes kept moving to them. I?d done it. I?d worn them to work. It had been scary, fun, interesting, suspenseful, and exhilarating. I?d felt so many emotions, both high and low, that just sitting on the couch I felt spent. I was still amazed at how quickly the day had passed, how it hadn?t felt oppressive like it had been feeling. Was it the distraction of the heels? The terror that I might be discovered? That seemed to fit. The heels had helped my work day become something exciting. No, not the heels. Peyton. I would have never found the courage if it hadn?t been for her leading me to do it. I thought of Peyton entertaining her friends. Was she thinking of me while serving some delicious appetizer or sipping on a glass of dark red merlot? Was she talking about me? Telling her friends about the new guy she just started seeing or was it too soon into our, what, relationship? Was it a relationship yet? No. Not quite, but it was becoming one. Of that I was certain. That thought made me smile. I went to bed thinking of what was coming next. Chapter 5 Escalation ?So, tell me,? Peyton said. ?Tell me, tell me, tell me.? The last came out in a rush, her brown eyes big and her face shining with anticipation. She was wearing jeans that fit her flawlessly and a loose white T-shirt emblazoned with a small fiery phoenix above her left breast. She had one hand in her lap. The other was holding my right hand. Her thumb was casually caressing my own. I told her about my first day wearing my heels to work and how terrified I?d been that someone would see them or even worse comment. I told her about waiting to go to the bathroom until I couldn?t stand it anymore and how each time after that had been a little bit easier. ?I used to work for a large advertising firm in Chicago, did I ever tell you that?? She shook her head. ?Yeah, I met my ex in Chicago and we wed there. When her dad got sick, I?d never seen her so scared. So, we moved down here to be closer to her parents. He died about a year after we arrived but for Linda, I think she needed that year. It was tough. On both of us. Her dad being sick, coupled with,? I glanced around the restaurant, ?my fetishes, led her to pulling away from me. I think she was looking for something she could control or maybe she wanted to feel powerful, so she lashed out and I was the closest. I forgive her. I do. Hindsight makes that easy but at the time, the stress of starting a new business, helping Linda help her dad and dealing with her rising hostility put a lot of obstacles in our way. I can?t say for sure, but the move broke us up.? I have her hand a squeeze. ?Anyway, where was I going?? ?I don?t know.? ?Me either. Shit.? I took a sip of my tea. After work, still wearing my heels, I?d gone home to take a shower. Peyton had suggested meeting for dinner at a local seafood place called The Iron Hook and after getting ready, I?d met her there. I wasn?t wearing my heels and when Peyton had seen me, she had flashed an exaggerated frown and said, ?poo.? Both of us had laughed. ?Something about Chicago?? ?Right. My job. When I started, I was given an assignment to deal with the draft editors in our print ad division. Now, I?m not an artist. I can?t tell Monet from Eddie Money, so trying to point out flaws in print ads was not something I was comfortable doing. At the time I thought that as long as the picture got the point across it was good enough. It?s not. Not at all. Subtle things can change the whole tone of a picture. Beads of condensation on a beer bottle, for instance. Sells more beer than a photo without them, did you know that? It?s true. The condensation shows a cold beer. I was supposed to sign off on these pictures, the ones you see in magazines and I hated it. I dreaded going to work each day thinking that someone would discover I was a fraud. That I didn?t know what I was doing. ?The thing is, it got easier. Once I started doing it, I started to believe I could do it. I had always thought that that was the wrong order of things. I thought you had to believe you could and then you can but that wasn?t the way it was for me. Yesterday was like that. I had thought that there was no way that I could wear my heels to work. That it would always be nothing more than an exciting fantasy. My panties were easy. I?d been wearing them exclusively since Linda moved out. Nobody could see those. Nobody would ever see them.? ?I did.? She stuck out her tongue. I nodded. ?Yes. You did.? The waitress came and took our order. Fried shrimp with asparagus for me and a blackened mahi over yellow rice for Peyton. When she left, I continued, ?The heels though? Like I said, I?d fantasized about it but never had the courage to wear them to work. Just like my old job in Chicago, though, once I started it became easier. It was like learning any skill, I guess. Once you learn how to do it, you know how to do it. I almost took them off that first day. Heck, I did take one off for about five seconds, but I thought about you and about what you had asked me at the bowling alley. I know it?s not the same, but I thought that if I took my heels off, I?d be cheating, not on you, but you. Does that make any sense?? She nodded. ?Today was easier than yesterday. I was still terrified, but it?s the fear of a roller coaster not of a monster hiding under a little kid?s bed. I?d gotten away with it once, so the second time had to be easier. That?s where I was going. Now I remember.? Peyton laughed. ?You?re cute when your flustered.? ?Uh huh. And nervous, right?? ?Right!? Her free hand left her lap long enough to take a sip of her pinot. ?Anyway, working in Chicago, I had a cohort, a man named Jim, and he was good at his job. Damned good. Turns out his wife had been downsized and they were having a hard time making ends meet. He ended up getting fired for running up about twenty thousand dollars of personal expenses on her company credit card.? ?Wow.? ?Yeah. The stories that came out after told about how it was a slow build up. He knew it was wrong, of course. Your comment now, your ?wow,? shows that you knew it was wrong too. Anyway, that first time had to be the hardest. Jim knew he shouldn?t do it, but he had to eat, right. So, he did it. He used his company card to buy groceries. That freed up money to pay some other bill. After that it became easier for him. The first time he leaped a giant hurdle; each time that followed was easier. That?s how yesterday was.? ?Oh, we can?t have thing be easy on you.? She said it with such playfulness that despite the fear her words brought I still smiled. ?Today wasn?t easy,? I said. ?Not at all. I?m just saying it was a tiny bit easier than yesterday. Like Jim, the first hurdle was the hardest.? ?Did anyone say anything today?? She took another sip of her pinot. I shook my head. ?No. Today was another relatively normal day. When I started my company, I never took lunch and after I?d grown the business enough to have a personal assistant, Gayle, she always took lunch, she seemed to pester me about eating. So, I made her a deal,? I shrugged, ?I?d buy if she picked it up. She jumped at the chance. Free lunch.? Our waitress brought our meal and refilled my tea. She asked Peyton if she?d like another glass of wine. ?No, thank you. I?ll stick with water.? ?Enjoy.? The waitress left us alone. I told Peyton how I had stayed tucked away in my office only leaving when I had to use the bathroom. I told her about my walk, how I shuffled my feet to hide the sound all heels made. She laughed at that, ?So you drew attention to yourself?? ?I don?t think so.? But did I? I thought about that as I took a bite of my asparagus. I had tried to hide my shoes by sliding my feet along the floor. Did that attract undue attention to my feet? Gayle hadn?t said anything so maybe she hadn?t noticed. If she did, she didn?t say anything and was that worse? Peyton laughed, ?definitely cute.? I sent her a live-action emoji of a face with its tongue stuck out that caused Peyton to laugh even harder. The conversation flowed. She told me about her get-together and how she had wanted to invite me, had even thought about it, but was having such a good time with me that she didn?t want to share with her friends. ?Not yet, anyway. I did tell Janey about you. She?s my best friend; we share everything.? I thought of the heels I?d worn to work. I thought of Peyton?s panties, the ones that I was still wearing. I thought of the foolish bet I?d made and about what was coming next. ?Everything.? My voice cracked. ?Yup.? She gave me a coy little smile. Peyton put her fork down and reached across the table for my hand. ?You have nothing to worry about. I trust her, and I need you to trust me. I didn?t tell her about everything.? ?That?s good,? I said, finally able to swallow again. Peyton finding out about me, while working out well, hadn?t been planned. I didn?t like the idea of someone else finding out. Of course, wearing my heels to the office meant I?d be discovered, right? Why were things so confusing and why was I enjoying it so much? Why did it feel like I needed it? ?Yet.? I let out a weak squeak. Peyton squeezed my hand tighter. ?Trust me.? I nodded. The thing is, I did trust her. Maybe that was foolish. I?d known her less than a week, but I felt a connection that was undeniable, and I was certain Peyton felt it as well. I?d already raced beyond my comfort zone and while frightened, I was anxiously anticipating where Peyton would next lead me. I liked how she hadn?t invited me to her party. It was far too soon for me to meet her friends. I wanted to be an addition to her life, not a substitution for it and that she was still able to do things without me showed that she was well adjusted and mature enough to stand on her own and not need me. That was important. I needed her to want me in her life, not need me in it. I?d seen it before, a woman trapped in an unhealthy relationship because she couldn?t afford life on her own. She pulled her hand back and took a bite of her fish. She downed the last sip of her pinot and took a sip of water. She was watching me, ?trust me.? I nodded though I wasn?t sure if she had asked a question or not. ?Good.? We finished dinner, the conversation turning to different topics. She told me about her day and I learned how horrible being a nurse could be. She talked about her newest patient, an elderly woman in pain who would cry, ?help me,? in a frail, timid voice for hours at a time no matter how much pain medicine she?d be given. ?It?s heartbreaking,? Peyton said, ?she has no visitors and she just hurts so much and there isn?t anything we can do. I?m not sure if she is really in as much physical pain as she says but she is hurting, and it breaks my heart that I can?t do more for her.? My esteem for Peyton rose even higher as she told the story. She was a compassionate, caring and tender woman and she was sitting with me. I felt lucky to have met her even if our meeting hadn?t been on terms I?d have arranged. ?Yellow, nice,? was not a great way to be introduced to your girlfriend. Was it a meet-cute like you?d see in one of those Hallmark Channel movies? Maybe. I paid for dinner, this time Peyton not reaching for the check like she had the first time we met. The growth in our relationship was evident in that missing gesture. ?Where to?? I asked as we left the restaurant, holding hands. ?Shopping.? The exuberance in her voice was as evident as the sun on a cloudless day. ?Oh,? ?Yep,? she kissed me on the cheek. ?I get to pick what you wear, remember?? I remembered. I had given it far too much thought. I licked my lips and swallowed. Hard. ?I remember.? ?Good.? At Peyton?s direction I drove us to the mall. She was chatting about shoes and skirts, blouses and earrings, stockings and bras. I was listening, feeling a rising trepidation with each article of women?s clothes she mentioned. Some I could easily hide while others seemed impossible. But wasn?t wearing my low heels impossible too? And hadn?t I accomplished the impossible? Isn?t that the definition of progress? Succeeding at the impossible until it was nothing more than the mundane? I?d worn my heels to work. Twice now and tomorrow would be day number three. How long until my heels became like the panties I wore every day. No longer impossible but normal and did I want to go there? I?d never thought of wearing a skirt to work but now that Peyton had put the idea into my head, I wanted to both run away from it and try it just the same. Peyton was smiling and dancing in her seat. She was excited, and I was the one exciting her. Was it me or my fetishes that had made her so happy and did it matter if my fetishes and I were so intricately entwined? I owned panties and heels and a corset, didn?t owning a skirt or dress follow? I parked the car. Peyton jumped out, ran around to my side of my SUV, and pulled me by the hand. ?Come on,? she squealed, ?this is going to be fun.? And it was fun. And scary. And embarrassing. I felt one emotion tumbling over another, each vying for dominance. One moment I?d be laughing and the next my face would be flush and burning crimson. Peyton led me to Victoria?s Secret first. I followed where she led, enjoying her dominance sure, but delighting in her exuberant happiness even more. Peyton was having fun and she was contagious. She stopped at a bin of pastel panties: light blues and yellows; oranges and pinks; lime green and periwinkles. A few she held up to her waist, then, smiling devilishly, she beckoned me to her and held the panties to my hips. ?Oh, they have these in your size, honey,? she said, louder than I?d like. The store wasn?t very busy. I guess not many shoppers went out on a Tuesday night but even the three shoppers and four employees I did see was much too large an audience. I shook my head, trying to signal I wanted her to keep it down. If she knew what I was trying to say she ignored my wishes and kept on smiling and laughing and making a pile of panties grow even larger. ?We?ll get two of each pair,? she proclaimed happily, ?one for you and one for me. We?ll have a matching collection and, oh, this is going to be fun.? The way her voice changed fascinated me. She?d latched onto an idea and suddenly the store was a lot less crowded. I was focused on Peyton and what she was thinking. Whatever it was it had stopped her shopping. She was thinking about something. Something big. ?What?? ?I told you that I had a way to keep you from falling out of my panties, right?? I vaguely recalled her saying that but hadn?t given it any additional thought. I nodded in reply. ?Well, I also have quite a few toys. No, not here. We?re here to shop. When you take me home tonight, I?ll show you and tell you my idea. It?ll be delicious.? Leaving me wondering what she was thinking, Peyton went back to the panties. There were thongs and boy shorts, bikinis and G-strings. True to her words she picked out panties that matched. Only the sizes were different; mine were two sizes larger than Peyton?s. Peyton handed me the panties. There had to be about two dozen pairs, two of each size. I stood there, in the overly bright store holding the overly bright panties with a face that was glowing in embarrassment. Peyton, however, was all smiles. ?Hi. I?m Carla, can I help you,? a woman approached. She was so skinny that I had to wonder if she was sick. She had long black hair and equally dark eyes. Her nose was slightly crooked like it had been broken more than once and hadn?t exactly bent put back into place correctly. Flashing a shark sized smile, Peyton said, ?I?d like a bra fitting please.? I shook my head as surreptitiously as I could, trying to dissuade Peyton from what she had planned. ?Of course. Follow me, please,? Carla said. Peyton followed Carla and I followed Peyton, my hands overflowing with panties. Carla led us to the back of the store, past more bras and panties, past corsets and teddies, past garter belts and stockings. I saw shorts emblazoned with words like Juicy and Pink. At the back of the store, standing next to four large changing rooms, Peyton, somehow smiling even bigger, asked, ?Can my boyfriend join us?? ?Um,? Carla hesitated. ?I don?t think...? ?You can measure him, too.? Please say no, I thought, over and over. Please say no. Please say no. Peyton squealed when Carla relented. ?Okay.? The three of us stepped into one of the changing rooms. There were mirrors on three sides and a padded bench on the back wall. With the three of us in there it felt a little cramped. ?Okay,? Carla said, ?I?ll need you to take your tops off.? Peyton pulled off her t-shirt and quickly undid her bra. Her lovely breasts popped free. If Carla wasn?t in the room with us, I?d reach out to give a touch, a squeeze, a kiss, but with Carla present I could only admire, and I did that with a lecherous grin of my own. Peyton shook her head, ?you can play with them later.? Carla looked surprised but maintained a professional demeanor. She pulled a pink ribbon measuring tape and wrapped it around Peyton?s chest, just below her breasts. She took a second measurement, this time across her boobs, and came up with Peyton?s bra size. A 34C. Then, suddenly, it was my turn. At Peyton?s direction I put the panties on the bench and took off my shirt. My hands were suddenly clammy, and my throat seemed to tighten. Was I really in a lingerie store being measured for a bra? It didn?t seem possible, but I could see myself in three separate mirrors and in all of them I was standing topless while a rail-thin woman was wrapping a pink measuring tape around my chest. It didn?t take long until I knew my bra size. I was a 38A. A small A according to Carla but an A cup all the same. ?Thank you,? Peyton said, dressing again. ?You?re welcome. Is there anything else I could help you with?? Was she being helpful or tying to flee? I couldn?t tell. ?Yes,? Peyton said, pulling her hair from her T-shirt. ?Can you show me where you keep your bras.? Smiling deviously, she added, ?Your 38A?s.? I felt myself tremble in anxious anticipation. The dressing room felt cloying and hot. My throat seemed to tighten even more. I opened my mouth to speak but nothing came out. ?Of course,? Carla said. She turned to face me, ?this way.? I finished pulling on my shirt and after gathering up the handful of panties, I followed Peyton and Carla out of the dressing room. The store, already bright, seemed even brighter. The few shoppers I saw, each lost in the own little world, seemed to be staring at me. One woman, looking at a pair of sweatpants and oblivious to what I was feeling was looking at me even though she wasn?t. To me, she was staring as were the three remaining employees even if I couldn?t see them. I was convinced that the security cameras mounted in the ceiling were somehow broadcasting the crimson hue on my face to the whole damned world. Peyton took my arm. ?Trust me.? I think I nodded. I followed Peyton and Carla to a circular rack filled with bras. Little black placards indicate the size ranging from twenty- four to forty. Carla moved to the black tab etched with golden ink with the number thirty-eight. She flipped through and pulled out a simple white bra with a tiny pink bow between the cups. A bra in my size. The thought was freaking me out; how did I have a bra size? Carla pulled out three more bras of different colors, each in my size. One was black with a black bow nestled in the middle. One was pink with little white polka dots that was practically see-through. The final one was yellow, the same color as the panties that started it all. ?We have a few more,? Carla said, indicating a pair of vertical racks sporting bras hung on thick wooden hangers. ?We?ll take all of these,? Peyton said, putting all four bras in my arms. Carla smiled and gave a little nod. ?Do you have any camis?? They did, and Carla happily led us towards the back wall of the store. Camisoles both simple and sexy were hung on more of those heavy wooden hangers. Some were V-neck others were rounded. Some were lacy while others were plain. Carla helped Peyton pick out about a dozen camisoles, most of them white though there was one light blue one, the color of a summer sky, one black one adorned with tatted lace and one red one with vertical black stipes. All of them had thin, spaghetti straps. They were light and soft and obviously feminine. I couldn?t imagine wearing them and I wanted to wear them at the same time. I?d looked at them online but never placed an order. My panties had mostly been enough. Still, I had looked and now it seemed like I?d not only own some, but I?d have to wear them as well. Why else would Peyton pick them out? Maybe I?d never wear one. Maybe Gayle or someone at the office would say something first and which idea was better? Wearing the camis and the bras to work along with my heels and whatever else Peyton decided or getting caught and suffering through that unimaginable shame? My dry mouth and racing thoughts didn?t have an answer for that. Peyton gathered the camisoles and thanked Carla for her time. ?You?re welcome. Would you like me to carry those to the register for you?? ?Oh, you?re a dear. Thank you.? She gave Carla the camis and turned to me, ?Come on, we?re almost done.? I knew what she was doing and meekly followed, my hands still full, while Carla carried part of my new wardrobe to the register in the back center of the store. We passed two young girls, probably still in high school. One of the two nodded at me and the other, a tall girl with thick glasses, laughed. They were laughing at me. I felt my stomach do a weird flip and my dry mouth because dryer still. Peyton led me past the two teenagers, to the row of garter belts and stocking we had passed on our way to my bra fitting. Had that really happened? The idea of it took my breath away. It seemed it had. Peyton fished through the garter belts, holding them to my waist, the delicate straps hanging down my thighs like tentacles from some octopus. She picked up two of them, one black and one white, and smiling, she opened a drawer next to the garter belts and pulled out six pairs of black stockings. Jet was the color written on the thin package emblazoned with a sexy leg adorned with the silky stocking. Who knew jet was a color? ?Okay,? Peyton said, ?this is enough. I?m dying to get you home.? That piqued my interest. I had sort of detached, hiding away, blending into the background, trying to diminish myself from the shame and excitement I was feeling but hearing Peyton telling me that she wanted to take me home with more than a hint or arousal in her voice brought me fully into focus. ?Sounds good,? I said, my voice a little whimper. Peyton giggled, ?let?s get out of here.? Ten minutes later I was walking through the mall, Peyton by my side. We were both carrying a big pink striped bag in each hand. Somehow walking through the mall carrying the Victoria?s Secret bags was much easier than being in the store. With Peyton by my side I looked like a pack mule; in the store I was a customer. The difference left me feeling somewhat more relaxed as we raced past shoppers going about their day. Outside, the full moon was shining overhead. A few stars peered down and as my eyes adjusted to the dark those few stars became dozens. We loaded our packages in the back seat. ?Take me home,? Peyton said. ?And hurry.? I happily obliged. Peyton pulled me from the car. ?The packages can wait,? she growled a throaty, hungry sound. We raced to the front door. Peyton opened the door and pulled me in after her. She was on me in a flash. She kicked the door shut as she reached for my shirt. She undressed me, not pausing as I reached for the hem of her white t-shirt adorned with the fiery phoenix. Her hands raced to my belt, fumbled briefly, before yanking my pants down, belt and all. My panties came next. She was kissing me as she fell to the floor in the entryway, guiding me down with her. Her fingers reached and found the part of me she was seeking. She gripped me and guided me into a velvety softness that took my breath away. She was wet; the shopping trip had affected her as well as me. Sated, and breathing heavily, Peyton snuggled into me. We were lying half undressed on the hard tile floor, taking the warmth the other offered. She pressed against me, her head lying in the crook of my shoulder. I kissed the top of her head. Peyton got up and kicked off her jeans. She stepped out of her panties, dropping both on the floor. ?Come on,? she said. ?I need a shower.? We showered. I washed her, and she bathed me. She purred contentedly as I scrubbed her hair. I watched, fascinated, as she took a razor to the stubble at the apex of her thighs. She surprised me after that, bringing the razor down to my own neatly tripped thatch of pubic hair. ?That?s got to go,? she said. ?I don?t like hair in my teeth.? That was all the motivation I needed and a few minutes later my crotch was as bare as Peyton?s. ?Much better,? she exclaimed. We got dressed. Peyton in a clean pair of shorts and a new t-shirt. I put on the same thing I?d worn to dinner and shopping. ?Where are my keys?? Peyton asked as we made our way to the kitchen. We searched for a few minutes and found them sitting in the front door deadbolt. Peyton?s need had been so great that she?d simply unlocked the door and left the keys in the lock. With her keys in hand she followed me to my SUV where we carried in my newest lingerie. She separated her new panties from mine and put hers in the wash, telling me that I?d have to wash them tonight after she sent me home. I gave her an exaggerated pout at that which made her laugh. She offered me a drink and set about getting each of us a glass of water. ?Now,? she said, turning serious, ?I?m curious.? ?About.? She led me to her couch and sat next to me. The television stared back at me and I could see our reflection in its dark face. She tilted her head and regarded me for a moment. From the kitchen I could hear the soft clicking of a clock. I heard the refrigerator kick on and outside I heard some kids screaming though I couldn?t make out what they were saying. I could see Peyton considering something as if she was struggling with a decision. ?Toys,? she finally said. I nodded. ?Okay.? ?I told you I have some, right?? I nodded again and then smiled remembering her story of wearing a vibrator to work, stuck into the warm recess I?d been in not thirty minutes before. ?I remember.? ?Wait here,? she said. She got up and came back a few moments later. She held in her hand something I?d recognized. I had the internet and I was an adult and I was kinky. When you have a panty fetish and you like how you look wearing women?s heels, wouldn?t it stand to reason that you knew about other, kinkier things? Well I did, and I knew exactly what Peyton was holding out to me. It was hard and plastic and pink and the shape of a flaccid cock. A small golden key jutted out of a round cylindrical lock built into the device. I wasn?t sure of the brand, but I was certain I?d seen a picture of it before. ?I want you to wear this for me.? I looked at the chastity cage. I?d seen them and thought about them, but I?d never considered owning one. I?d read stories and found them fascinating. Hell, I?ve masturbated to stories of men and women and even couples in chastity, but did I want to wear one? The look Peyton was given me told me that not only did she want me to wear it, but the idea excited her almost as much as our shopping trip had. There was this needy anticipating in her almond eyes. I could see her trembling slightly. ?You?re shaking? Are you okay?? ?I?m scared.? The tone in her voice at those two words stung, ?About what?? ?That I?ll scare you away.? Her voice cracked, and I melted. How could I not? I was already smitten and if she could accept my fetishes how could I not accept hers? I told her as much and she leapt at me, pushing me backwards. The chastity cage tumbled to the carpet. ?Oh, you wonderful man,? she said, kissing me passionately. Her hands slid along my stomach, traced along my stomach and came up to wrap around my neck. She kissed me, and I kissed back. It didn?t lead anywhere, I was spent already, but it was fun and passionate, and I loved every second of it. ?This is going to be fun,? she said. I still wasn?t sure if I wanted to wear it, but I kept quiet. This was now Peyton?s show. I?d been leading the parade during my panty fashion show. It was Peyton?s turn to lead now. She climbed off me and pulled me to my feet. She picked up the chastity cage and unlocked the lock. The cage separated from an oddly formed ring, almost like a Mobius strip I made when I was in fifth grade so long ago. Peyton instructed me how to put on the ring. I fished one testicle through the loop, winced when I worked the second one through and felt my pulse in my cock when I worked it into the same tiny circle. Peyton seemed to be trembling again but this time it was for an obviously different reason. ?Why do you have this?? She paused and gave me a serious look. ?My last boyfriend cheated on me,? she said, and I could hear the hurt in her voice. ?I promised to give him a second chance if he wore this. He agreed but when it arrived, he broke up with me instead. I?d already bought it. I don?t know why I didn?t throw it away.? She shrugged. ?The idea of it though was something I couldn?t shake. I?m glad...? she stopped speaking and stood to kiss me instead. ?Thank you.? I gave her a smile and watched as she continued applying the rigid pink cage to my suddenly attentive dick. She sat on the couch, with me standing in front of her and waited until my interest waned enough for her to continue. She placed the cage onto me, working the tapered end into a matching grove. I could feel how tight the cage was, how the hard plastic was holding me in a snug embrace. With the cage fully seated in place, she stuck the cylindrical post into the ring that encircled my captured balls and turned the key. The key pulled free, but the cylinder stayed in place as did the cage. It was locked on. Peyton, her eyes wide, was absorbed in the look of my locked-up cock. ?This is fucking awesome!? She had the wide-eyed look of a child entering Disney World for the first time and the exuberance of a boy about to lose his virginity. She was enraptured, enthralled and entertained. I dropped one hand to tug on the cage. My balls pulled away from my body, but the cage stayed in place with my spent penis fully trapped inside its pink plastic prison. ?How long will I wear this?? She smiled at me, rose to her feet, and kissed me full on the lips. Hard. I felt my cock twitch, but it couldn?t do anything else. I moaned a bit causing Peyton to laugh. ?That?s up to you?? ?Oh?? ?We?ll make a game out of it.? She giggled. ?Every day you?ll wear one of your new panties to work. Tomorrow,? she added, ?I want you to wear a bra and a cami, too.? I had expected that, so I gave her a nod. ?And your heels. Of course.? Another nod. ?After work we?ll have dinner. I?ll be wearing a new pair of panties, too. If we?re wearing the same ones, we?ll fuck like rabbits.? ?And if we?re not.? ?Then you?ll make me cum with that talented mouth of yours.? I thought of all the panties we?d bought a few hours earlier. What was it? A dozen pairs each? That gave me a one in twelve chance of picking right. My odds would get easier each day as I would know which pair, she was wearing but then it dawned on me that she would know which pair I?d worn as well. Peyton laughed, ?It?s not as easy as you thought is it? I wonder,? she was teasing me now, ?how often should I wash my panties? Maybe every day?? She laughed at that. ?I promise I won?t wear the same pair two days in a row.? ?Doesn?t seem fair,? I said but my voice was playful and light. I wasn?t being harsh or pouting, I was simply absorbing the fix I found myself in and finding that the game, while lopsided, was exciting and I was looking forward to playing. I didn?t know why or maybe I did, and I just didn?t want to admit it. ?And guess what else?? ?What?? Peyton left my side and came back with a new pair of panties. They were light green, the color of antifreeze. Their size told me that they were one of hers. She pulled them up my legs and settled them against my trapped cock. ?See how my panties fit now. You won?t fall out of them. Just like I said.? She laughed at that, a victorious sound, like she?d solved a particularly fiendish brain teaser. The panties seemed to hold the cage snugly against my body. I thought that the panties helped the cage feel more comfortable. ?Much better,? I agreed. She kissed me again. ?Thank you, Mason. I had the best time.? I admitted I had as well. We said our goodnights and I went home, the key to my cock staying with Peyton. It was her game and I was enjoying the rules. I knew why. I was submissive. It was one of the reasons I wore panties and heels, and it was the main reason why I let Peyton lock me up and lead our relationships. I didn?t need to apologize for it; it?s who I was, and Peyton accepted me. How could I not go along when her leading me was exactly what I needed most? At home I put my panties in the washing machine and got ready for bed. As I was brushing my teeth my phone chirped. It was a picture of Peyton?s panty covered crotch. Should I wear these tomorrow? Another picture came in. This one of her ass adorned with a thin red swath of color from her newest thong. Or these? Let me know and I?ll wear the same ones, I texted back. She sent an emoji of a pair of red lips. Not gonna happen, mister. Then, good night. Night. With the day behind me, I put my panties into the dryer and went to bed, worried about what the next day would bring. Chapter 6 Like me I woke up groggy. I woke up about a dozen times throughout the night as my cock tried and failed to become erect. I had read about this nocturnal discomfort, but I?d never thought I would experience it. I must admit that I found the situation arousing which didn?t help. I was living an erotic catch-22. The chastity cage excited me, frustrating me and causing my body to wince as the cage was pulled away from my body as my captured erection succomed to the hard exterior of the cage, which aroused me. It was an interesting, exciting, frustrating, intense, and electrifying experience. That Peyton was in charge of it made it even more so. If I had known how much fun the cage could be, I might have ordered one years ago. I got out of bed and found a picture on my phone. It was from Peyton. There, spread out on her bed, was a cornucopia of pretty panties. Every pair we?d purchased the day before was lying on her bed like soldiers on parade. The caption she?d included read: decisions, decisions. She followed it up with a little yellow face winking one eye. I smiled. I couldn?t help myself. She was toying with me, taunting me, tantalizing me. I could feel the cage become tighter as I imagined Peyton slipping a fresh pair of panties up her long, toned legs. I could see her adjusting them against the clean-shaven flesh between her thighs. I felt my imprisonment becoming tighter as I thought of each pair of panties that picture portrayed and how I owned an identical pair. I took a shower, thinking of Peyton and what panties she was wearing. I shaved my face and brushed my teeth wondering what pair I would wear. It was a fun distraction that kept me from other, scarier thoughts, but it couldn?t banish them completely. Leaving the shower, with a towel wrapped around my waist, I went to the dryer and pulled out my own collection of panties. Hidden in that pile was the same pair that Peyton was wearing and my reward for matching whatever pair Peyton chose was a reward worth winning. I pawed through the panties, imagining each of them on Peyton?s lovely body, how they would cup her ass or caress that smooth, warm cleft between her legs. Which pair was she wearing? Did she send me those two pictures last night, the one with the red thong and the one with in the lovely peach color, as a clue or were the pictures a way to confuse me and hinder my decision. Whatever, my decision wasn?t coming easily. I picked up one pair, looked at them, set them aside and picked them up again. I didn?t have any idea what pair Peyton was wearing so I would have to go on blind luck alone. I picked up the pink pair with little white polka dots. Of all the ones we bought they were my favorite. The color was decidedly feminine and that appealed to me; the polka dots made them fun. Had Peyton picked the same panties? I?d find out later and be either rewarded or frustrated. No, I?d get a reward. Peyton promised me that we?d still have fun only I wouldn?t be allowed to come and why the hell did that thought arouse me even more than the panties I was now wearing? I went to my bras next. My little 38A?s. We?d only bought four and looking at them I couldn?t imagine wearing one to work but that was what I was going to do. I grabbed the simple white one. I figured I would start slow and pick the least conspicuous one. I fastened the trio of latches in the back of the bra at my nipples and then spun the bra around so that the clasp was centered in my back. I worked my arms through the straps and settled my bra into place. There I stood, a submissive man wearing a locked chastity device, a pretty pair of pink polka dot panties and a simple white bra. At that moment there wasn?t anything masculine about me. My trapped cock lurched at the thought. It was like I had been somehow cheating myself by only wearing panties. There was a whole world of feminine clothing that I seemed to enjoy. Why hadn?t I noticed that before? I pondered that last question and came up with an answer. My failed marriage. If Linda had been supportive of who I was, or maybe who I was hiding from myself, then maybe I?d have discovered what I should have known was there. Peyton not only accepted me and my growing fetishes, but she seemed to not only enjoy them but complimented them as well. She liked what I liked, and she was willing to lead me when I wanted to be led. The camisoles came next. Like the bra I chose a simple white one. I pulled it on, liking how it felt on my skin and how it seemed to hang on me. I looked at myself in the mirror. A man clad exclusively in women?s underwear. Somehow, I wanted to keep going. I gathered up a pair of stockings and a garter belt. The garter belt, like the bra and cami, was white though it was more lace than anything else. Four little streamers hung low, waiting to clasp my stockings. I opened the package marked Jet. I typically wore black socks to work so I reasoned that black stockings would blend into my heels and pants and wouldn?t draw the eye like a pair of white stockings would. Sitting on the bed I gathered one stocking into a ball and worked it up my leg. Little hairs stuck through the fine netting, looking out of place, but the electric tingle I got sliding the stockings into place reminded me again of the cage Peyton had locked into place. Everything I put on sent a tug of arousal at that captured part of me. There was no denying how excited I got with each additional piece of women?s clothing. With both stockings in place I affixed the garter tabs to the lacy tops of the stockings. The tabs were simple round pips that slid downward from a wide gap lower into a snug loop. I did the two below my ass and then the two in front. Standing up I felt the taut pull of the garter suspenders. I couldn?t help myself. The feeling was so delightfully enticing that I had to shorten the suspenders to maximize that electrifying taut pull. I paced my bedroom loving how the garter belt felt tugging on the stockings. I felt a little disappointed when I donned my work pants and buttoned on a shirt. I didn?t want to wear a blouse and a skirt, well maybe I did but I couldn?t, but I did feel a pang of sadness when I had to hide my lingerie from the world. I couldn?t face my office in my underwear, my visible heels were bad enough, but covering my bra and panties, garter belt and stockings made me feel just a tinge of sadness. Still, putting my low heels on erased that feeling and replaced it with one of terror again. It was amazing how quickly I went from an amazing high to a different, agonizing low. What was going to happen when someone at my office found out about my heels? I had focused on that question for far too many hours and just slipping them onto my feet, while arousing if my chastity cage was any indication, was also frightening. Those heels, the only part of my feminine outfit that wasn?t hidden, once again raced to the forefront of my thoughts. Who would notice them first and what would I say when I was called out on my choice of footwear? My mouth went dry and I could feel my pulse against the ring that encircled my trapped cock. I walked into the bathroom and looked at myself in the mirror. Besides the blush on my face I didn?t look any different than normal. I couldn?t see my camisole, my bra or panties. My garter belt or stockings were hidden from view. Only my heels looked remotely out of place. Still, a small smile did flash across my face. I was wearing more women?s clothing than men?s. That thought astounded me. I knew that one day soon I?d be clad in women?s clothing exclusively. Peyton had hinted at that and I found the idea both scary and enticing. I wanted it to happen while at the same time I wanted to avoid it altogether. That internal battle was both overwhelming and impossible to ignore. Suddenly I wanted to be wearing a blouse and a skirt. Peyton had somehow ignited what Linda had doused. Just as quickly I wanted to run from the idea, my own fear extinguishing the idea. I combed my hair and left the bedroom. I gathered my keys and wallet and cell phone, putting them in the same pockets I always did. The thought that I?d need a purse flashed across my brain, causing me to shake my head at the idea and smile at the same time. It was a silly idea and one that seemed to fit. I walked out to my SUV, enjoying the clip-clop-clip sound my heels made against the concrete. As usual, I was the first in the office and I was happy about that. No matter how excited what I was wearing made me, the idea of being discovered scared me even more. Not that my captive cock understood that concept. The way my cock pushed against my pink, feminine panties, you would think that I was anxiously anticipating the day I got caught so I could escalate my eventual descent into wearing more outwardly apparent women?s clothing. Like skirts and dresses. I wanted to wear them, not pants - no, skirts and dresses. Blatantly feminine attire. I?d not realized it until now, sitting at my desk, feeling the uncomfortable tightness of my cock cage and savoring the delicious tug of my garter belt. Feeling those things, feeling distracted by those things, made work somehow less daunting, less oppressive. It was like work became something I could endure if I was wearing armor and my armor of choice was bras and stockings, panties and camis, skirts and dresses. Somehow, I?d become more of a man by wearing women?s clothing. Gayle came in, gave me a smile, and asked me about my night. Polite office small talk. ?Great. How was yours?? ?Who is she?? That took me aback. ?I?m sorry.? ?You?re smiling. You never smile. Well, not for a while. So, who is she.? I stammered out something but Gayle just grinned. ?Uh huh. Well, that answers one question.? She looked down as if she could see through my desk. ?And I guess that explains other things, too.? Did she know about my heels? It seemed to me that she did but she didn?t comment on them. She just said, ?Well, I can?t wait to meet her.? I mumbled a response, but I couldn?t focus on what she was saying. They way she had peered at my desk, like she was seeing what the heavy wood hid, had me distracted. Did she know? Would she say something? Anything? I felt my balls twitch inside their rigid prison, trying to protect themselves from what I couldn?t say. I just felt the twinge and felt a knot of pain halfway up my spine. My office suddenly felt cloying and far too hot. Had I been discovered? I thought I had but since Gayle had left, saying something but for the life of me I couldn?t remember what it was, I had no way of knowing. I picked up my phone and sent Peyton a text: I think my secretary knows about my heels. I brought one foot up to my lap and unbuckled my left heel. I stopped myself before I removed my shoe and sent Peyton another short message. Does that mean I can take them off? I waited for an answer but didn?t receive one. Peyton had told me that she kept her phone tucked into her purse during her work shift. Something about hospital policy that those involved in patient care weren?t allowed to carry their phones. It meant I had to wait. Well, I didn?t have to, but I had to just the same. It was still Peyton?s game and even if I thought I was losing I had to play to the end. I got to work, and my work day flew by. Problems that seemed insurmountable before I met Peyton were so much easier now that I had the terrifying distraction of my heels and everything else I was wearing. I liken it to tinnitus, the incessant droning in your ears that you can?t shake or hide from. Or maybe it was like a toothache, a throbbing pain that wouldn?t go away and kept you distracted from so many other, smaller things. My lingerie and heels were exactly like that. A background concern that seemed to mask the problems that had made me loathe coming to work. There was a sexual component to be sure; it was sexy as hell to be a man wearing women?s clothing and I found myself enjoying the thought of wearing even more even if the only thing left was the outer layer, but it was more than that. It was Peyton deciding the rules of the game, it was the delicious naughtiness of wearing not just panties but so much more and wearing them to work made it even scarier and somehow more fun, too. My phone chirped right as I finished eating the club sandwich Gayle had brought back from the deli across the street. Did she say anything? No. Too bad. Guess you?re stuck wearing what you?re wearing. She followed that with: How is it going? I could almost hear the compassion in her query. How could I answer that question? It was going fine. I was getting away with it and that was exhilarating. It was scary for the exact same reason. I wanted to stop, and I wanted to keep going. I wanted to wear a blouse and a skirt, and I wanted to put on a t-shirt instead of my camisole. I wanted what I wanted, and I wanted what Peyton wanted. Work was easier, there was no getting around that fact and that seemed to be the biggest catalyst for why I wasn?t fighting what Peyton had suggested. Work had been a slog and now it was once again easy, like it had been when I?d first started. Business was booming, and we?d have to hire more people. Decisions about how to improve print ads that had so flummoxed me when I?d first started now jumped out at me with the ease of cat catching a wounded mouse. When my employees came in with a small problem, I?d see the answer now instead of a thousand different scenarios playing across my brain. That background hum of excitement caused by Peyton and my escalating cross-dressing had somehow simplified work, resetting it to an easier, more productive time. Good. How?s work? Slow, which is good. Eating lunch. Come over after work? I took a play out of Peyton?s playbook and sent back and emoji of a thumb pointing skyward, the universal symbol for A-OK. Peyton sent back a smiley face. The rest of the day went by just as easily as it had been since I?d started wearing my heels to work. Yes, it had only been a few days but the difference in my attitude and how simple my work days seemed to be, proved that first wearing my heels and now a full set of lingerie distracted me enough, pulled my attention away from what was making work so terrible, that it was once again easy. And Peyton was at the center of that. Every time I saw my heels or felt my cock lurch inside its new cage, I thought of her and her olive skin, her chocolate eyes. I could almost smell the scent of her floral perfume and wondered if I should be wearing it as well. Gayle left, and I found myself surprised that I was ready to leave to. That toothache, that ringing in the ears, the distraction of my heels made it so that I wasn?t behind when the clock hit five. I was ready to leave as Gayle was telling me she?d see me the next day, once again commenting on the warmth in my skin and the glow that I seemed to carry. ?You never did tell me her name.? ?Peyton.? ?I can?t wait to meet her.? I smiled, not yet ready to share but wanting to show her off just the same. ?You will.? ?Good. See you tomorrow Mister Sweet.? ?You too, Gayle.? And just like that work was done. I waited a bit, both making sure I wasn?t forgetting anything and letting my office building empty. I still wanted to hide my heels as much as possible. I wasn?t ready to answer questions that I knew would be coming if my heels where discovered. I still held onto the assertion that they would be. I decided I needed to talk to Peyton. Maybe I should bring up the subject to my staff, let them know what was coming and I had no doubt that Peyton and I were working for a goal that I hadn?t even realized I had. I wanted to wear a skirt to work. Or a dress. Definitely not pants. I?d somehow progressed from panties as a necessity to a full-on crossdresser. How I couldn?t say. Yes, Peyton was the catalyst, but I don?t think she was the source. Once you open a box you can?t unsee what was lying inside. I left the office and drove straight to Peyton?s. She?d been disappointed that I was without my heels when we met the night before and I found that I didn?t want to disappoint her. I wanted to make her happy. Seeing a smile lighting her face made my own mood elevate to something atmospheric. I made it to her house with ease and was delighted to find her car in the driveway. At the door I rang the bell. Peyton opened the door, smiling, and let me in. She looked at my feet with the same intensity that Gayle had given the modesty panel of my desk. ?You wore them for me.? I nodded and told her that that thought had entered my mind. At that she gave me a deep kiss with lots of tongue and roaming hands. Her fingers slipped downward and undid the buckle to my pants. I felt her unfasten the latch at my waist. I felt her unzip the fly and a moment later my pants were at me knees. She took in my polka-dotted panties, she took in the white garter belt and the jet-black stockings. She toyed with the hem of my camisole. ?I knew you were going to wear those.? ?You did?? I wondered what that meant for our evening. Did she wear the same pair hoping to reward me or did she choose a different pair to amplify my frustration? Another question traipsed through my mind: which one did I want? She tugged her scrubs down to reveal that she was wearing the exact same pair as me. I cheered. I hadn?t meant to, but I did. Peyton burst out laughing, bringing one hand up to her mouth as if to stifle her merriment. She stepped backward, nearly tripping on the scrubs at her ankles. She wobbled, bent over and fell to the floor, no longer covering her mouth but now clutching her stomach as huge guffaws escaped her lips. She mocked me, making that same raucous cheering sound I made. Her mirth was contagious, and I found myself laughing right along with her. It took a moment, but she finally stopped laughing long enough to wipe her damp eyes. Peyton giggled, cheered like I had, giggled some more, but it was a lot less explosive. She was laughing and smiling and taking me in. Breathing heavily, Peyton climbed to her feet, ?dinner can wait,? she said, kicking her scrubs to the side. She reached out and pulled me after her. She led me to her bedroom and had me lie on her bed. She helped me take off my pants, working the hem past my heels. She unbuttoned my shirt and helped me throw it aside. With my male clothes on the floor, Peyton pulled off her top, standing above me in her bra and the panties that matched my own. I saw the key to my cage hanging from a gold chain around her neck. My eyes were glued to her fingers as she unfastened her necklace. She climbed into bed with me and unlocked what had been trapped all day. I responded to her touch in a way I couldn?t help to do. Lying next to me, Peyton said, ?do what I do.? Her hands caressed her breasts through her bra. I parroted her movements, caressing the lacy cups of my bra. Peyton nodded and when her hands slid down her body to dip into her panties, I did the same, reaching my hand lower to caress my turgid cock. Peyton let out a little moan as her fingers reached that sensitive part of her. I grabbed my cock, feeling the hard heat of it. Peyton pulled her hands from her panties and slapped my errant hand. ?No. Like I do.? Her hands slipped back into her panties and I followed suit. She rubbed herself in fat, slow circles. I tried to do the same, but my anatomy was different. I rubbed my hand against the base of my cock, trying to copy Peyton?s movements. Peyton?s hand moved faster against her pussy and my hand came up to once again grab my cock. I had not planned on it, but I simply did what came naturally. Peyton stopped me in a flash, her hand once again slapping mine. ?No, like a woman. Only like a woman from now on.? And that?s what happened. I masturbated like Peyton, my hand making rapid circles on the hard flesh where the underside of my cock met my balls. Peyton kept an eye on me and I kept my eye on her, savoring the languid, steady build up. ?Yes,? Peyton moaned, her back arched, as her fingers pleasured her body and my overly excited mind. I rubbed my cock like a woman rubbing her own wetness. My fingers made strong, quick circles. My cock twitched and throbbed and begged for more but every time my hand came close to encircling my shaft Peyton was there to correct me. ?Like this,? she moaned, rubbing herself again. ?Like me.? Her breathing was coming faster now as her fingers became a blur. She flailed about, kicking the comforter off the bed. My hand matched hers, rubbing with a furious intensity. I could feel my pleasure mounting in a way that was both erotic and unfamiliar. My cock twitched and lurched and my fingers moving in a rapid-fire circle against the base of my erection. My panties seemed to stick to the back of my hand. Next to me Peyton was gasping for air. She lurched and gasped and screamed my name. I kept going, rubbing as fast as my tired fingers would allow. I wanted to grab my cock; I wanted to stroke myself like I?d done so many times, but I didn?t. Peyton wouldn?t allow it, that much I knew but it was more than that. ?Like me,? she?d said. ?Like a woman.? That was such an erotic thought that I wanted to keeping going as Peyton had commanded. I wanted to know how it felt. Peyton, panting and trembling next to me, watched as I continued to rotate my fingers against my erection. I felt the pleasure climbing at a glacial pace, rising and rising. I thought I was going to come but instead my body jerked and the pleasure waned a pace, forcing me to keep going. Slowly, oh so slowly, I felt the pressure build until finally, with Peyton watching in rapt attention, I came, a thick, mess shooting from my cock to splash my belly and a bit higher to stain my new bra. I reached up to stroke my cock, but Peyton was there to slap my hand away. Tingling with need my hand went into my panties and down to the base of my shaft again to keep rubbing, my hand sliding up and down now instead of making rapid, needy circles. A bit more leaked from me until I was lying sated next to Peyton, my eyes closed, my chest rising and falling as my rapid breathing slowly returned to normal. Peyton snuggled into me, not caring about the mess I?d made. She kissed my naked shoulder. ?Always like that,? she said authoritatively, ?like a woman. You?re my girl now.? I liked the way that sounded or maybe I liked the way Peyton said it and maybe those two things were the same. I nodded in agreement. ?Good.? We took a shower. Drying off, Peyton locked my cock away again, putting the key back on her necklace. I liked the way it looked resting between her lovely breasts. Dressed again, me in everything I?d wore to work but my bra that was hanging in Peyton?s shower to dry, and Peyton wearing panties and a sweatshirt from her alma mater, LSU, we finally had dinner. I told Peyton about my day, regurgitating how I was certain that Gayle had seen my heels. ?Well, did she say anything?? ?No.? Peyton giggled, ?Poor Sweetness. I guess you?re stuck wearing your heels.? ?I guess so.? I admitted my fears, not afraid to be honest with her. Maybe I?d grown since Linda and I divorced or maybe it was my growing affection for Peyton, but I wanted to be honest with her. I wanted her to know exactly what I was thinking and feeling and how one affected the other. She listened and smiled, touched me both appropriately and inappropriately and when we finally said good night, we?d made plans to kick things up again. Tomorrow after work we were going shopping. Chapter 7 Head to Toe (1) Once again, I didn?t get much in the way of sleep. The cage locked on my body had an odd way of making itself known at the most inappropriate times and I?d been woken up by the cage letting me know it was still there about half a dozen times during those long, lazy hours I should have been sleeping. I had had a hard time falling asleep remembering Peyton?s assertion that after work we?d be going shopping and this time for more outer wear. I sat up, leaning against my headboard and pondered the implications of where Peyton was leading me. She was clearly interested in my crossdressing, maybe as much as I was. She seemed to take great delight in what I wore, and it was obvious she enjoyed choosing my wardrobe. I had to admit that I enjoyed it too. Maybe it released me from the responsibility of my actions. If I didn?t pick what I wore than I couldn?t be responsible for getting caught wearing my lingerie or my heels. Maybe that was childish, of course the overarching responsibility was my own, but if Peyton choosing my outfits allowed me to justify doing what I had long ago wanted to do, then what was wrong with that? That led to longer, deeper thoughts. I had loved panties for as long as I could remember. I?d stolen my mothers?, my sisters?, and once when I was about twelve or thirteen, I?d even jumped a fence to steal a sexy pair of lime green panties from some stranger?s clothes line. The way I felt wearing panties, how it both calmed me and aroused me at once, had led to me trying on other things. When I was sixteen my family went on vacation and I was left alone for the whole week they were gone. Our house had a sump pump that had yet to be replaced even though it was badly in need of repair, and so when it rained someone had to go outside, life up a plastic garden gnome to reveal a single rusty valve that needed to be turned. My father hadn?t wanted to leave the house unattended and I was old enough to stay home alone. It turned out to be the best vacation of my young life. The day after my family had left, I?d gone into my parent?s bedroom and tried on every dress my mother owned. Nothing I wore calmed me as much as panties did, but the elicit thrill I got told me that I enjoyed wearing women?s clothes much more than I enjoyed my own. I hid that side of me as best I could, settling for panties alone, but over time what I owned and what I wore had escalated. I bought panties, of course, and my heels. Once I bought a dress but had to get rid of it the same day it arrived for fear that Linda would find it. I bought skirts and stockings, bras that didn?t fit around the chest and one with empty cups so big that only cantaloupes would fill the void. Over time I?d purged it all. Everything but my panties. And for the longest time that was enough. My panties relaxed me and calmed me and just hiding them from the world, spotting attractive women and smiling at the thought that my underwear was prettier than theirs, kept my spirits high enough that I didn?t really need to purchase anything more. So why was the idea so enticing that I wore even more to work? Wasn?t a properly fitted bra, stocking attached to the delicious straps of a garter belt, a simple silky camisole and heels enough? Normally, during the Linda years, it would be far too much. Linda barely tolerated my panties, everything else would send her into apocalyptic rage. So why wasn?t it enough now? Why did I want more? Was it Peyton? She was enjoying having me be her crossdressing Ken doll, but was it more than that? She helped, there was no denying that. It?s what I wanted as well. Maybe the two mixed together become something far stronger than either of us separately. We were like a two-part epoxy that needed to be intermixed to become something powerful. It was fun, scary, exciting, arousing, kinky and so many other things rolled into one and we both wanted it. It was like some fruity concoction, a Cosmopolitan ordered at a restaurant perhaps. Mix well and enjoy. ?Fuck it,? I said. I got out of bed, took a shower and stood in front of my panty drawer. It was full of the panties Peyton and I had purchased. I pondered the blob of colors. Which ones would Peyton choose? Did she go through this same consternation, this hemming and hawing, trying to decide which ones were best or did she just grab a pair and move one. Panties for me were a delicious novelty. For Peyton they were the norm. Adding in our game made my choice even more impossibly fun. I?d be rewarded if I chose the same pair she did. Yesterday she had picked the most feminine pair, thinking I would. Or maybe she knew I would; she was learning all about me. Which pair would she pick today? I grabbed the peach colored pair. I liked them. They were soft and silky with a sheer backside. The little bow in the front and the lace around the waist added to their appeal. Peyton had sent two pictures the day before, the peach pair and the red thong, so I thought maybe those would be on top. With nothing else to go on I could only use what little information I had. I pulled the panties up my legs, smiling as I did. Was Peyton wearing the same ones? I?d find out after work and was looking forward to the discovery. I donned the same simple white bra from the day before. After washing it yesterday I knew it was okay to wear again. I chose a different camisole, a simple black one with thin spaghetti straps and a ribbon of satin decorating the bottom hem. The camisole was shorter than my t-shirts, ending about three inches above my panties. A black garter belt and jet stockings completed my underwear. I got dressed in a dark suit with a black buttoned shirt. A white shirt wouldn?t conceal the dark camisole underneath. My pants and jacket followed and then it was time for my heels. The chastity cage seemed to shrink as I donned my heels as my mind took in the implications of what I was wearing and how arousing I found it to be. If I got such a thrill over Peyton choosing my lingerie, wouldn?t it follow that I?d like her choosing my outwear as well? I wasn?t sure, but I wanted to find out. I was playing a treacherous game. It was only a matter of time until I was discovered and then what? I was the boss so nothing could be done to me but what would happen to my business? My excited mind latched onto that thought and refused to let go. Business was booming, rising farther than I?d ever imagined, so was I taking a risk by playing these games with Peyton? I doubted I would lose any customers; my staff dealt with them more than I did now. I was the CEO, I had salesmen and women that handled garnering new customers and I had advertising executives that did the bulk of the true writing. But, would my employees leave because they didn?t want to work for a sissy or a faggot or whatever other derogatory name filled with misunderstanding or derision was thrown about these days? Most crossdressers weren?t homosexuals and who cares if they were? Still, somehow there was this stigma, and would that cause my employees to leave? I didn?t want to think so, but I couldn?t be sure. Right now, it was a game and only my heels were noticeable. I could easily play it off as a lark, a playful game between two new lovers. But if this escalated could that excuse fly? Heels were one thing. A skirt or a dress was something else entirely. I scolded myself for sabotaging a game Peyton and I hadn?t yet played but I couldn?t shake my racing thoughts. I knew the company policy concerning discrimination. When I?d hired Amber and Clayton it was one of the first things they did. ?You don?t want to get sued, Mason. Discrimination is big,? Amber had started. ?Probably the biggest issue that an HR department deals with,? Clayton finished her thought. When we?d written the policy, using the federal regulations as the guidelines, I hadn?t imagined that I?d been writing them to protect me. The irony of it made me chuckle but there was no merriment in it. It was a nervous laugh and nothing more. Fully dressed, I left the house, my thoughts tossing and tripping through my mind as fast as a rocket leaving the earth. I had a problem that needed to be addressed. Funny, every solution I came up with avoided the simplest. Stop playing the game Peyton and I were playing and return to normal, with only my panties hidden from view. The thing is, I didn?t want to stop. I wanted to see where things were leading. Maybe rolling the car had done more damage to my brain than I thought. No, I knew that wasn?t true. Peyton was enjoying the game and I was enjoying her. It was more than that. Maybe I was tired of hiding my true self. Whatever it was, I had a problem that needed to be addressed. I got to work before everyone else. I made the coffee, surprising myself by how simple an earlier nightmare had become. I no longer worried about shuffling my feet to the bathroom. The first few days of wearing my heels I?d hardly drank anything. Now my heels were second nature and after such a short amount of time. It amazes me what a person can get used to. Did wheelchair bound people feel the same way after enough time had passed. Did a wheelchair become as much a part of them that they don?t think anything of it? I kinda hope so. Peyton texted me, taunting me with a very dark picture of her crotch with her scrubs pulled away from her body. I couldn?t see what panties she was wearing but I could imagine the view that wasn?t quite revealed. Which ones did I wear? You tell me. A smiley face sticking out a tongue came back. We sent a few more texts. Peyton ended it with a pair of big, red lips and a note telling me she?d see me after work. Looking forward to it. And I was. Despite my fears and my consternation, I wanted to continue. I wanted to be led where Peyton wanted to lead. After all, she was doing the thinking for both of us. That thought made my trapped cock pulse. I sent an email and a minute later I took the bull by the horns as the old saying goes. Clayton came into my office, ?You wanted to see me boss?? ?Where?s Amber?? ?Dealing with Blue Cross. I think our insurance rates will go down next year,? he shrugged but flashed a warm smile, ?I don?t know how she does it but she?s amazing.? I tilted my head. Clayton got it. ?A good woman props you up, doesn?t she?? Clayton?s grin got bigger. Whatever he was thinking it sure made him smile. ?Yes.? He considered me for a moment. ?You met someone?? My business isn?t so big that I didn?t know everyone and heading the HR department with his wife Clayton was just as informed. ?You could say that.? ?Is that why I?m here? Are you getting married?? ?Not yet,? I said but that made me pause long enough to think that maybe I would one day. Probably to Peyton. After Linda I?d been content to not date, to just live my life alone. It was a good life and I?d been happy, but now, with Peyton I was happier. The great thing about life is it can always get worse, but it can always get better, too. Clayton waited until I caught up with my thoughts. ?It?s just,? could I do this? Should I? ?What is it?? I had been worried that Gayle knew about my heels but if things progressed, and I thought they would, then my heels were the least of my concerns. Was I doing more harm than good by attacking a problem before there even was an issue? I wasn?t sure but now, with Clayton standing in front of me, I was committed. And that was fine. A sickness treated was better than a disease left to fester. I brought my feet up and put them on the desk. My pants rode up, revealing the jet-black stockings underneath. I?d been worried about Gayle seeing my heels and now I was showing them to Clayton. What would he think when I didn?t exactly know what I was thinking? He looked at my face, my heels, the stockings and my face again. ?Nothing to worry about,? he said. ?Really?? He laughed, ?you should see your face. I take it this is a big deal to you?? Duh. ?Duh.? Clayton laughed again. We chatted, Clayton pulling up a chair. When he left my office, I felt better about a lot of things. Maybe society wasn?t ready for a full-on crossdressing epidemic, but it seems my office was. ?I would recommend you, shall we say, come out to the staff. Maybe send an email. Facts are way better than gossip.? I thanked him and then called Gayle into my office. I?d been afraid of her seeing what I was about to show her. Was I crazy? Maybe. Was it the right thing to do? I didn?t have an answer for that. Clayton convinced me that it was so I took that as a sign that I was on the right course. ?Oh, I saw them on Wednesday,? Gayle said. ?And again yesterday. I figured I?d see them again today. You shuffling around like a zombie in The Walking Dead was suspicious and with a quick glance at your feet I knew what you were doing. That and you couldn?t really hide being suddenly taller.? She giggled, ?they?re lovely,? she added. I explained my heels and what was probably coming. She seemed to take it all in the way a doctor takes in everything their patient is saying. She tried to be stoic, but she was smiling larger and larger as I went on. Finally, she said, ?I can?t wait.? By the time the day had ended I wondered if I?d done the right thing. That old saying that you can?t unring a bell raced through my brain time and again. I was committed even if I didn?t want to be. What would Peyton think and why hadn?t I included her in my decision? I scolded myself for that. This concerned her, and she deserved to be involved. I berated myself as I drove to her place and I mentally spanked my own ass as I parked in her driveway. Of all the things I had done that day, coming out first to Clayton, then to Gayle and finally sending an email to my entire staff both reminding them of our discrimination policy and what changes they were likely to see in me, the fact that I?d omitted Peyton from any of it stung that most. ?I?m sorry,? I said the moment Peyton answered the door. She saw something on my face, ?What?s wrong? Sweetness, what?s wrong?? I felt a wave of sadness wash over me, like a heavy morning fog obscuring a tall skyscraper. I suddenly felt horrible, like I?d done something terribly wrong. At the time I had merely been solving a problem now it felt like I had somehow hurt the woman I was growing attached to. She led me into the dining room, took a seat next to me and then clasped my hands in hers. ?Mason, what?s wrong?? I felt tears in my eyes. Had I hurt her? Had I hurt us? It took about ten minutes for me to get it all out. At the beginning of my story her eyes showed concern, by the end she was smiling. ?Oh, you gorgeous, silly man.? She stood up and threw her arms around me. She kissed my forehead, my nose and both my damp eyes. ?You,? a kiss on one eye, ?silly,? the other eye, ?silly,? the first eye again, ?man,? and back to the other. ?You had me so worried.? ?I?m sorry,? I said. I followed that with a sniffle. ?Don?t be. You had no idea how much this means to me?? I didn?t understand, and I told her that. ?You?re crying because you thought you hurt me. That...? Peyton kissed me again, ?that means everything. You have no idea.? I thought I understood what she meant, and I felt the two of us growing even closer. If I hurt that much just imagining how much I hurt her, then the two of us were connected in a far deeper way than I had realized. Maybe Peyton didn?t quite feel about me the way I felt about her, but the sadness on my face and the way my lips quavered, told Peyton how far we?d come in just over a week. She kissed me again and then pulled me to my feet. ?Go wash your face. We?re going shopping,? she said. ?I?m going to change.? ?Need any help?? She flashed a radiant smile. ?Nope. I?m not ready for you to see my panties.? She mouthed the last in a breathy whisper that made my captured cock take notice. I smiled back, wiping my eyes with my jacket sleeve. The time for unexpected tears had passed. It was time for fun. (2) It was Friday night and the mall was packed. Countless people milled through the concourse, passing stores filled with toys and clothes, jewelry and vapes, electronics and books. Peyton was wearing a simple white skirt that ended just below her knees. She was wearing a tan blouse with a single, large button at the base of her skull. Her hair was pulled into a pony tail that bounced from side to side as she walked. She was wearing a simple pair of tan flats. I was wearing the same suit I?d worn to work and of course the heels were still on my feet. They weren?t locked on, but they might as well had been. Peyton hadn?t let me change, smiling devilishly as I protested. ?Don?t worry about it Mason. I?ll keep you safe.? We walked into the mall. Peyton had a goal and after my work day it seemed I now shared it. I still couldn?t understand what had prompted me to take the steps I?d taken. Had it simply been a problem that needed to be solved or was there something else, some underlying need to dress more outwardly as a woman. Was I a full-on crossdresser? If so, why had I been content to wear panties almost exclusively for as long as I could remember? We walked through the concourse, Peyton?s arm draped in mine. We were two lovers out for a bit of fun. My heels were making that lovely clicking sound but in the din of the mall it was barely noticeable. I was hidden amongst the throng of people going about their evening, oblivious to anything that didn?t concern them. It was at that moment that I truly understood the adage of hiding in plain sight. My shoes were visible as was the color on my cheeks, but nobody paid me any attention. I might as well of been invisible. Would that change when I wore something else, like a skirt or a dress, I couldn?t say but somehow, I was certain that I wouldn?t be invisible after that. Peyton led us into an Anne Taylor Loft. Skirts and dresses and blouses and slacks hung from circular racks. The clothing was stylish and professional. It was a store where professional women bought professional clothes to fit in at the board room or amongst high- powered CEO?s. Nothing trashy jumped out at me. A young woman approached Peyton, mostly ignoring the invisible me. ?Hi. I?m Mona. Can I help you find anything, miss?? Peyton, eyes wide and sporting a huge grin on her lovely face, said, ?We?re looking to expand Sweetness?s wardrobe.? She nodded at me. Mona?s smile faltered but came right back. I guess she worked on commission. ?Of course. What are you ladies looking for?? I didn?t know it was possible, but my blush grew even darker. I swallowed, afraid to speak. But, down below, it was obvious I enjoyed the shame I was feeling. Peyton did the talking, explaining how I owned my company and I needed to wear a certain style. Mona was nodding, her eyes scanning me from head to toe. ?That won?t be a problem. Do you know your size, miss?? First ?ladies? and now ?miss.? Did it help her to serve a man by using those words? Maybe it did and what did it matter? I would be dressing as a lady or a miss, so I guess the words Mona used worked just fine. I shook my head. My mouth was far too dry to speak. ?That?s okay,? she was smiling, and it appeared genuine. I guess she was over the initial shock and a sale is a sale. I?d learned that simple lesson when I started my business, taking on every job I could get. Now that I?m more established I can afford to be a little pickier in the jobs we accepted but at the onset I would try to sell shoes to a double amputee if it put food on my plate. ?We?ll get you set up in a dressing room.? She led us through the brightly lit store. A few women were shopping but they paid no attention to me and the lovely woman at my side. Why would they? A woman was shopping with her spouse in tow. Mona escorted me into a dressing room. Peyton, all smiles, told me to get comfortable. ?We?ll be back soon. Why don?t you get that suit off?? It was an order and the downstairs tightening let me know I enjoyed her bossing me around. But I knew that already. I didn?t really need the reminder. Mona and Peyton left me alone. I stripped out of my suit and stood there, bouncing from foot to foot, wearing nothing buy my lingerie. I was a man, I could feel the proof of that struggling to grow inside the confines of its cage but at that moment I was also a lady shopping for a nice, new wardrobe. Well, Peyton was shopping, I was just waiting around to be her living mannequin. And it was exciting. I winced as the reality washed over me, my knees coming together as that tiny cage grew tighter as I swelled against its unforgiving embrace. Peyton returned with Mona in tow. Both women had their hands full. They were carrying dark suit skirts and crisp white blouses. They hung the clothes on a pair of hooks. Mona left, after giving me a knowing smile at what I was still wearing, leaving Peyton behind to help me get dressed. I can?t explain the excitement I felt. Peyton and I played dress-up and I felt an electric current racing down my spine as I stepped into my first skirt. Goosepimples broke out on my arms and the little hairs at the base of my skull stood up straight. The chastity cage grew so tight that I was certain it was leaving permanent marks in the skin. Peyton, still smiling, took it all in. Grinning evilly, she pulled up her skirt, showing me her panties. We didn?t match, but just seeing them and realizing their implication made that chastity cage distract me even more. I was horny, fueling some long-dismissed fantasies, and now, at that moment, Peyton let me know that I was in for a long, frustrating night. I moaned causing Peyton to laugh. I tried on the skirts and the blouses. They were stylish and neat and fully appropriate for the boardroom. I looked like an executive secretary and that thought had me doubling over in unquenched arousal. Gayle never dressed as I was at that moment and it was arousing as hell. My face needed work, as did my hair, but from the neck down I was all business and pretty damned sexy. Peyton couldn?t keep her hands off me. Did she know what she was doing? That she was fueling my desire and increasing the pain in my cock? By the look on her face and the smile toying with the corners of her mouth I thought that maybe she did. But she was doing it for her and not for me. There was a longing need in her eyes and she wasn?t about to be denied. I watched as she slid her fingers under her skirt. I watched, my own eyes glued to the performance before me, as Peyton slipped her thin, blue panties down her legs. She stepped out of them, ran then up my skirt, trailed them over my blouse, before dropping them onto my shoulder. Her hands moved higher, grabbing my hair. She pushed me to my knees, stepping forward and flipping her skirt over my head. I did what she desired, enjoying the scent of her, the taste of her and wincing in discomfort as my entrapped cock struggled against its cage. I savored the illicitness of what we were doing and where we were doing it. The thought that only a simple curtain was keeping our naughtiness from being discovered made it somehow even hotter. We finished what Peyton started and the blissful look on her face was quite the opposite of the burning frustration etched on mine. I felt the cage pulling away from my body. I felt the rising pressure of need sending shivers along my heated skin. The dressing room felt hot and cold, loud and silent. It was everything and nothing and I was loving every second of it. Normally, in those post-Linda years, I?d take care of myself and it would be done. Now, with Peyton and her locking toy, my sex life, while different thanks to the chastity device, was somehow even greater. The stories I read had told me about this, but feeling it made it so much more powerful. I was nuclear with need and grateful that Peyton was in charge. Peyton cleaned my face with her panties and then stuck her panties in the pocket of my pants sitting on a little bench next to us. ?That was wonderful, Sweetness,? she purred, rubbing her hand along my spine. ?Thank you.? ?You?re welcome.? We went back to shopping and by the time we were done I had a full two weeks? worth of office wear, all skirts and blouses. Peyton knew, or maybe I had let it slip, that I didn?t want slacks. The more feminine the better was the motto that we seemed to follow. Mona was satisfied with our purchase; we?d spent over fifteen hundred dollars. She gave us her card and Peyton put it in her purse. Leaving the mall, me once again wearing my suit, Peyton led me back to Victoria?s secret. Another three hundred dollars and I had a few more bras, a few more camisoles, a dozen new pairs of stockings, and three more garter belts. The panties we had covered, and our game was fully in effect. We left Victoria?s secret and returned to my SUV to unload our bags. Sitting in the car, Peyton gave me a lingering look. ?Are you ready for what?s next?? ?What is next?? She waited until I caught up. Finally, ?I don?t know.? ?That means no.? She did not seem to be disappointed, and I loved how she took my feelings into consideration. ?We?ll go slow, then. When you do this, I mean really do this, and I can?t wait,? she was giddy as she said that last part, ?you?ll have to have your hair and makeup done. We won?t make a mockery out of you, Mason. We won?t.? It had never once crossed my mind that we would. I told her that and she nodded, with a lovely smile on her pretty face. ?Good.? We left the mall and I took her home. She invited me in and led me to her bedroom. I undressed her, and she undressed me and after satisfying her with my mouth and my fingers, Peyton unlocked the cage and took me into her mouth. I trembled beneath her ministrations and groaned in frustration as she stopped short of my own anticipated release. Peyton was all smiles as she reached for the cage again. ?You guessed wrong, Sweetness. You know the game.? I was both speechless and enticed. The game, already frustratingly fun, had grown into something electric. I waited, my hands balled into fists as my erection waned enough for Peyton to put her lock in place anew. I was needy and achy and while my body longed for more my mind was satisfied. It would be enough. We said goodnight and I drove home to put my new clothes away. I meant to, but I couldn?t help myself. I tried on all the skirts and blouses again. My hair and face were what Peyton had meant when she asked if I knew what was next. If I was to go to work fully dressed as a woman then my hair and makeup would have to match. I wouldn?t go as a parody of a woman, I?d go as presentable as I could. Staring at myself in the bathroom mirror, I thought it wouldn?t take much. At just over five foot nine inches, I wasn?t the tallest of men which helped mask my true gender. My eyes were soft and round and with my cheekbones, I thought that a bit of color could enhance them enough to get the job done. My hair was short; we would need a wig. I put my clothes away, brushed my teeth and got into bed. The day had started strong and ended stronger. My hand slipped into my panties to toy with the cage that kept me captured. Only Peyton had the key. I somehow enjoyed that idea. It would be interesting to see where Peyton led me next. I thought of her and how our brief relationship was progressing. I had truly felt sad, so much so that tears had come unbridled, just thinking that I?d hurt her somehow. I was smitten, there was no denying that. Would love come next? Chapter 8 A First Five weeks passed in a rush. Each day I would choose my panties and each night Peyton and I would get together to see if I was to be teased and locked up anew or rewarded for guessing correctly. With the number of panties we had, I lost more than I won, but to be honest I didn?t know which was better. Either way I was rewarded with only the reward being different. Sometimes Peyton would tease me, sometimes she would have me tease myself, only allowing me female masturbation, slapping my hand if I even attempted to grip my heated arousal. Either way, every time I guessed wrong, I would wind up locked again after coming dangerously close to the precipice of release. Even if the rules were against me, I must admit I loved the game. During those delightful weeks Peyton and I grew closer. We spent more and more time together. I introduced her to my friends where she fit right in, being as crass as my male friends and as sophisticated as their significant others. I met her friends, finally crashing one of her biweekly dinner parties. She told me the next day that I was ?perfect?, and I beamed at the praise. It pleased me that I pleased her. ?Charlene told me that you?re a keeper, which is high praise from her. And Janey gave me her blessing.? With that she had given me a little peck on the cheek, then the nose, the lips, and that led to something far more exciting for Peyton. I had not chosen the correct panties that day so our love making, while a tad one-sided, still satisfied us both. Work progressed and was still much easier than it used to be. Gayle commented on my shoes and took an interested delight when Peyton and I would go shopping and I?d buy some different heels. Where once I had two pairs, I was now up to six. The first time I came to work in a new pair of heels Gayle wasn?t shy about letting me know what she thought of them. And that she?d seen them right away. It was true, I never did hide them from her. ?Oh, Mason, those are adorable.? And they were. They were red, with a taller, three-inch heel. A single strap ran over the arch of my foot with another thin strap running from the cross-strap down to the center of the red velvet heel. Shopping for shoes was much more fun when you weren?t worried about hiding them. At the onset I?d only worn my black heels. Now I could wear reds or whites, blacks or my newest golden colored ones. The colors were amazing and far less drab than any pair of men?s shoes that I owned. I had three purses and two wigs and a huge collection of makeup. Peyton and I were working towards a goal and there wasn?t any rush. My office knew what was coming, as did I. The only variable was the when. Since I had come out to both the HR department and my staff as a whole, I was no longer safe from anyone commenting on my heels. Since I had revealed them there wasn?t any fear of them being discovered. ?Tomorrow,? Peyton said. We were lying on my couch, watching Netflix. Peyton was snuggled into me. I could smell the sweet coconut scent of her shampoo. I could feel the heat of her body next to mine. She fit against me like two Lego blocks snapping together. When she spoke, I could hear a bit of playfulness. I knew the answer but I had to ask the question anyway. ?What about tomorrow?? ?Tomorrow you?ll be dressed fully as a woman. Are you ready?? I didn?t have an answer for that. Intellectually I was. It was what we were both working towards. Peyton and I had discussed it at length. We had talked about the risks; we?d spoken on the pure enjoyment she would get out of knowing that I was her woman and I?d be dressed as she wanted. Peyton took great delight in leading our relationship. She usually chose where we ate dinner or what we watched on TV. Even now, watching Netflix, Peyton held the remote control in her hand. And I liked it when she led. Running my own company, having to keep so many people employed, where I had the ultimate authority in everything, sometimes felt taxing. It felt good to let Peyton lead. For her it was the opposite. The doctors had the final say in anything; she enjoyed being the one in charge. I think she needed it. Most of our discussions were serious. Most but not all. The ones that weren?t serious were far more fun and were my favorite. Peyton would taunt me, call me her sissy, her girl, her Barbie. She?d make teasing comments, ?Oh, Sweetness, you?re going to be the prettiest girl at the office.? Or, ?You?ll make all the boys hot. Do you think they?d like to get into your panties?? Or, ?Maybe you should be the secretary.? Sometimes she was vulgar, sometimes she was sweet, but when she teased me, called me her girl or her sissy, my cock would lurch in its tight confines. I loved it when she teased me, and she knew it. ?Maybe,? I finally answered. ?Well, you don?t have any say so you might as well get used to the idea. Just think, tomorrow when you go to work, you?ll be wearing a pretty pair of panties, a sexy little garter belt, stockings, a bra, a blouse and a skirt as well as your heels.? She sat up and climbed from the couch, ?I bought you something. Well, a few things?? ?Oh?? I wasn?t worried and even if I were it wouldn?t matter. Peyton was leading the show. ?Come on, we have some things to do.? She climbed from the couch and pulled me after here. She led me into the bathroom and helped me undress. I quivered in anticipation when she unlocked my cage even though I knew I?d be left wanting as our panties that day hadn?t matched. Smiling and whistling a little song I knew but couldn?t name, Peyton ushered me into the shower. ?Shave everything,? she said. She watched as I turned on the water, laughing when I jumped out of the way of the stream until if got hot. ?Start with your legs,? she said and proceeded to give me instructions. She watched as I set one leg up on the edge of the tub and lathered it with shaving cream. She nodded as I slid the pink razor she?d bought me up from my ankle to my knee. I watched as my leg hair came with it. It was like mowing the grass, taking one long stripe away at a time. After my calves I did my knees and then my thighs. Under Peyton?s guidance I shaved my crotch anew. Thanks to the chastity device I wore I?d been keeping my pubic hair absent so that area was decidedly less difficult. ?Keep going.? I shaved my stomach and my chest. My armpits went next under Peyton?s lead. She had me do my arms and helped me shave my back. My skin felt weird and a bit unpleasant. The water felt hotter and when I shut off the heated stream, the room felt much colder. Drying my body every bit of skin felt different and eerily strange. I wasn?t sure I liked it but I did enjoy the way Peyton ran her hand over my legs and made a soft, cooing sound. ?Very nice,? she said. She grabbed my hand and pulled me into the bedroom. ?Lie down.? I did. The first thing she did was lock me up anew, smiling as she pulled the key free of the lock. I could only watch as she put the slipped the key back onto her necklace. Still grinning, Peyton opened the nightstand on her side of the bed. Two weeks earlier, I?d cleared a dresser drawer for her, opened a stretch of my closet and gave her her own nightstand. I let her know she was welcome and giving her a key solidified the idea that she was welcome in my house anytime she wanted. She pulled out a rather large box and a small bottle that held some thick, viscous fluid. Peyton climbed onto the bed and then straddled my thighs. Smiling, Peyton pulled the box to her side. She opened it and pulled out a tan colored blob that looked like a chicken breast about to be thrown on the grill. I knew what it was the minute I saw it. Peyton had never mentioned getting me breast forms; I guess it was meant to be a secret. Smiling even larger Peyton pressed the breast form against my right nipple. I shifted slightly at the cold. ?Look how big they are, Sweetness. Oh, you?re going to be stacked.? And they were big. They weren?t huge but seeing the artificial breast sitting on my chest I had no doubt that they would be noticeable. She pulled out the twin to the first one and placed it on my opposite nipple. I looked first to Peyton?s smiling face and then down to the breast forms that Peyton was holding against my chest. The thought that they weren?t huge disappeared. Seeing them side by side made them seem outrageous. ?How big?? She giggled, ?you men and size.? Her giggling became a laugh which became a full-on guffaw. Somehow, I had cracked her up. ?They?re a D cup,? she informed me when she got her laughter under control. ?For your shape they?re the best fit. You?re a little taller than most women and a little more stout.? She laughed at the frown on my face, ?You?re not fat and you know it but you?re a man so you?re a bit bigger. This size is proportional.? I doubted her assessment, but I trusted her. ?What?s that other thing?? I knew the answer; I read the internet. ?Glue, silly.? With that she opened the bottle. She coated the back of my left breast form and did the same to my chest. She waited, rubbing her thighs against my freshly shaved ones. My cock in its tight cage responded and I felt the cloying tightness. Peyton purred at that, enjoying the affect she was having on me almost as much as I was enjoying her affecting me. She waited about five minutes, just rubbing against me and running a finger over my balls and tapping on the hard cage. She was toying with me, taunting me, teasing me. Distracting me. With both the back of the breast form and my own chest tacky to the touch, Peyton deliberately placed the form on my chest, taking her time, positioning it just right. She repeated the process with my right hand side, smiling the whole time. ?Don?t move,? she said, climbing off me. ?Let the glue set.? ?How do I remove them,? I asked, cupping my suddenly heavy breasts. ?You? You don?t. Only I can, got it?? I knew it was another game and they way she said that proved it. I felt the fire below pulse in response, ?yes, ma?am.? ?Good.? Peyton left the room and came back about forty-five seconds later. In her hands was a fresh Victoria?s Secret bag. She placed it on the bed next to me. I watched, mesmerized, as she pulled out another ten pairs of delicious panties. They were soft and silky, and I wanted to touch them. ?Five more for each of us,? she said, grinning playfully. ?You were guessing right far too often.? ?About once a week isn?t too often,? I protested, still staring at those new panties. ?My game. My rules.? Next, she pulled out a trio of bras. She handed me one. It was black and decorated with purple and white orchids. ?Put that on. It will help.? I sat up and felt the pull of those breast forms on my skin. They were heavy and awkward. They seemed to move where they wanted and each time they did they tugged uncomfortably on my skin. I brought my hands up to hold them aloft, taking the pressure off my chest. It dawned on me then, cupping my breasts, that I now needed a bra. A bra would help the forms feel more comfortable. Peyton was watching me from the side of the bed. Smiling, taking in the way I held my breasts, seeing the way I moved and how my face twisted as a pang of discomfort raced along my skin. I glanced at the tag ? A 38D. I put on the bra, fastening the clasp below my artificial breasts, spinning the bra around so that the claps were behind me, before working my arms through the straps. I adjusted my breasts into the cups before pulling my hands away. The bra held the breast forms, taking pressure off my skin, while propping them up as if offering them to the world. Peyton was right ? I was stacked. ?Very nice,? Peyton said. ?We?ll have to get you some more bras, but it?ll be much more enjoyable with you there to try them on. Maybe we can have Carla measure you again. Won?t that be fun?? I thought it sounded humiliating and when I told that to Peyton she said, ?Then that?s what we?ll do.? That was followed with another one of her adorable giggles. We spent the rest of the evening getting me ready for work the next day, going over my wardrobe and playing with makeup. Peyton grew more and more aroused and twice before we went to bed, I satisfied her with my fingers and mouth and tongue. As was the normal now, Peyton stayed the night with me. Sometimes I slept at her place and once we spent the weekend together in a hotel just to put our normal routine on hold. Peyton fell asleep with the speed of a cheetah while I lay there, my eyes closed, contemplating the following morning. I was going to go to work dressed as a woman, head to toe. It would be a first. A big first. Maybe the biggest. And I was scared. I felt my pulse in my temples. My mouth was dry. My breasts felt heavy and I was still wearing my new bra because it helped take the weight of my breast forms off my skin. Every physical discomfort paled to the thoughts that were keeping me awake. I would be going to work in a skirt. Sure, it was a well-made skirt, black with thin silver pinstripes. I had a matching woman?s blazer and a white blouse with lace piping at the collar and cuffs. It was a beautiful suit. A beautiful woman?s suit, and I?d be wearing it to work. My staff was ready. They had all seen my heels and the few people that commented where mostly supportive. Maybe society was changing and a man in a skirt wasn?t that far from mainstream or maybe my staff just wanted to eat, and they were happy enough with their jobs to keep their mouths shut. Did it matter? Did they talk about me behind my back? Maybe. Probably. Gayle was looking forward to it. I can?t count how many times she had said that she couldn?t wait to see me in a skirt and then followed that up by asking if I wanted to trade jobs with her. ?Maybe you can be the pretty secretary fetching coffee for me, Ms. Sweet.? She had laughed at that while all I felt was a tightening in my cock cage. The idea was deliciously demeaning and seemed to somehow fuel my submissive fantasies. Just that thought was exciting. I didn?t admit it to Gayle and I kept it from Peyton. I just knew if I mentioned it to Peyton, she would find a way to make it happen. No, some fantasies are best kept secret. When the alarm clock woke me, I was surprised to learn I had slept at all. Peyton stirred, opened her eyes and then leapt from bed. It had dawned on her what was happening and that had pulled her from her slumber with all the zeal of a child racing downstairs to see what Santa brought the night before. She reached for me, touched the breast forms still captured in my lacy, flowery bra and let out a soft little moan of excitement. That lead to her unlocking me and satisfying both of us. After she said, ?I know what panties you?re wearing and in celebration I?m going to wear the exact same pair.? So at least that game was still going, and the rules not violated. Not that it mattered; I enjoyed my reward. Peyton helped me shower, washing me all over. She took out my pink razor and shaved my face. It was very sensual and erotic. She was all smiles as she ran the razor along my skin. She shaved my armpits and touched up a few stray hairs at my knees. My breasts, supported only by my skin, felt heavy, but I was mostly unaware of that feeling. I was too caught up on what Peyton was doing and the giddiness she revealed. She was having a blast. Peyton turned off the water and dried us both. She used to towel to blot my skin, ?like a woman,? she instructed me. I simply nodded. Peyton pulled me to the mirror and used the same towel I?d blotted dry with to dry my hair. She gave me a little frown, shook her head, and then smiled. The master bathroom had twin sinks and between the sinks were four little drawers. I had given two of them to Peyton and she raced to open the bottom most drawer. Smiling even larger now, her face glowing with it, Peyton pulled out a pair of tweezers. ?This might sting,? she said. With that she proceeded to pluck my eyebrows. It did sting both physically and emotionally. Peyton was sitting on the vanity, plucking my eyebrows and I could see them in my reflection getting thinner and thinner. It was something I would not be able to hide even if I were wearing jeans and a t-shirt. How could I revert to Mason mode with my eyebrows so thin? Peyton kept plucking, thinning them more and more. She shaped them as well. Where once they?d been quite full and maybe a bit bushy, they were now thin and slightly arched. I?d never be able to hide them. Peyton must have sensed my trepidation. ?Don?t worry,? she said, still smiling, ?we can use a pencil to fill them in. Nobody will know.? She leaned forward and gave me a quick kiss. ?Well, I?ll know.? I looked at myself in the mirror, unable to take my eyes away. With my eyebrows shaped my face looked much more feminine. It was a tad scary knowing that this new, more delicate face was my own. My cheeks were awash with a crimson hue as the thoughts of my upcoming humiliation seemed to brighten not only my cheeks but my neck and forehead as well. The bathroom felt hot, my skin felt even hotter. Peyton hopped off the vanity and ran from the bathroom. I called after her. She chided me to ?not move.? I felt compelled to obey. I wanted to, of course, but it went deeper than that. The bathroom had only one exit that led to the master bedroom. The master bedroom led to a short hallway that opened into my laundry room and the interconnecting walkway between the kitchen and the formal dining room before spilling out into the large family room. The bathroom was a lot further away from the terror that was work. The nightmare that was outside. No, the bathroom felt safe. That was why I wanted to stay put. Peyton returned with the makeup we had been playing with the night before. She hopped back on the counter and proceeded to add a splash of blue to my eyelids. She blended the eyeshadow with her finger. Smiling and humming a Lady Gaga song we both liked, Peyton pulled out a mascara brush and did my eyelashes. She put lipstick on my face and added a bit of concealer to my neck and cheeks before adding a splash of artificial color about half as bright as my own embarrassment had caused them to glow. She finished by adding some black eyeliner to my eyelids, pulling the black color into a point a tiny bit away from my eyes. My face, already looking effeminate by my plucked eyebrows now screamed something much louder. I looked almost like a woman and while not exactly pretty I wasn?t homely either. I?d rate me a bit above average and being a man, I really couldn?t ask for more than that. Once again Peyton jumped off the vanity. Lady Gaga disappeared as Peyton started singing an Elton John song. I didn?t know the words, but I recognized the song just the same. Peyton darted into the walk-in closet and returned with a wig. ?Your hair is getting longer,? she said, ?but it?s not long enough yet.? It was why we had purchased the wigs. I was growing my hair out; Peyton had forbidden me from getting it cut. ?If you get a haircut, Sweetness,? she had said after a panty check that I?d not won, ?I?m going to buy each of us a hundred pairs of panties. You?ll never match me then.? If it was a threat it was a damned effective one. I had agreed and why wouldn?t I? It was her show after all. Peyton put the wig on my head. In the mirror behind Peyton a comely woman wearing a towel wrapped around her fake breasts stared back at me. The makeup Peyton had done was about as good as it could be. I tasted the lipstick, the artificial thickness of it feeling heavy on my lips. I felt the wig on my head and the hair as it rested on my shoulders. My hair was a light brown tinged with auburn. It was long and straight and parted just a little off center. It reminded me a little bit of the way Jennifer Aniston wore it on that old TV show Friends. My hair curled slightly at the end. ?Wow,? Peyton said. I nodded, staring at my reflection. I dropped the towel. I wasn?t exactly thin, but I wasn?t fat either. My stomach protruded slightly, like a woman just beginning to show that she was pregnant. With my breast forms hanging from my chest I thought I looked like a woman, at least from the waist up. Women didn?t sport what I did down below. Still, it was a damned good illusion. We crossed into the bedroom where I got dressed as Peyton looked on. After donning my bra, I put on the white blouse with the lace piping. I slipped black stockings up my denuded legs getting a soft erotic chill. I stepped into a black garter belt and attached the straps, enjoying the taut pull every bit as much as I had the first time I wore that particularly feminine piece of lingerie. I stepped into my skirt, trembling both in fear and excitement. I slipped on my blazer and slid my feet into a new pair of heels. They were black but with a three-and- a-half-inch heel that was quite a bit narrower than the first pair of heels I wore to work. ?Oh my God, Mason, you look...? ?What?? I asked, suddenly afraid. Did I look ridiculous? Scary? I wanted to see but I was afraid to look. The bathroom was a single door away. I glanced at the open door, at Peyton who was eyeing me with a huge grin on her face. Her mouth was hanging open and her eyes were wide. It was a good sign or at least I took it as one. I had to see. I marched into the bathroom and stared at a lovely, professional woman in the mirror. I turned and the woman in the mirror matched my every motion. I raised my hand and my feminine doppelganger did the same. It was uncanny. I looked like an average woman wearing an expensive suit about to leave for her high-powered executive job. I could have been a fancy lawyer or a high-end account executive for a Fortune 500 company and I looked the part. I looked like a woman. It was uncanny and scary and exciting and so many other things that I had to grab the vanity to keep from falling to the ground. Peyton stood in the doorway, watching me in the mirror. She still wore that playful smile but there was something else on her face. Pride, I think. I could almost see her revealing in what she created, and I was here creation. Never in a billion years would I have the courage to do what I not only wanted to now do but was I was racing towards. I was going to work fully dressed as a woman. Just the thought of it buckled my knees. Peyton got dressed in her simple green scrubs. I felt a petty sense of amused superiority like I was the pretty girl at school that got a car for her birthday while my best friend only received a cell phone or something much smaller. It was petty, and it made me tingle. Peyton was and always would be prettier but at that moment, standing next to her in my expensive suit, I was the important one. Maybe petty is too small a word. Peyton was all smiles as we walked to the door. ?You can do this,? she said, holding my hand and giving me a kiss. ?And I can?t wait to hear all about it.? She handed me my purse and picked up her own. Mine was a simple black clutch while Peyton?s was white with dark brown piping that she hung on her shoulder. ?Thanks,? I said, taking my clutch in my clammy hands. I smiled nervously. It was time and I was ready, but I was terrified too. I?d felt so many emotions since I?d climbed out of bed, both high and low and I knew I?d be feeling even more as the day progressed. Standing at my front door, with Peyton offering her indefatigable support, I knew I?d make it through the day. I wanted to. She wanted me to and as we left my house and locked the door behind me, I could think of nothing else but making sure I earned the wanton look that Peyton was giving me. She was excited and that was because of me. As a man I can?t think of anything more arousing that being given the look that Peyton was giving me. It was a look of wanting, a look of overwhelming need, a predatory look of carnal lust. ?I?ve got to run by my place,? she said. ?Our panties don?t match yet, and we haven?t washed the new ones.? She smiled, looking up at me with that same needy gaze, ?but they will.? She kissed me goodbye and left me standing alone at my SUV. I was ready, and I wasn?t, and it didn?t really matter. I was committed. Or maybe I should be. Was what I was doing crazy? Maybe. Was it exciting? Oh, my God, yes! I opened the door to my SUV and drove to work. It was time. I was ready. Or so I thought. Chapter 9 Downsized I?ve given a lot of thoughts to firsts. Once, long ago, I had my very first kiss. That wasn?t my first first, of course. Once, long ago, I took my very first breath and at some time in the time of far-from-now, I will take my last. I?ve done so many firsts. I caught my first fish; I drove for the very first time; I received a puppy as a gift; I tasted a woman?s kiss and felt her lips upon mine. Life is full of countless firsts and even today, after living for over three decades, I was going to live something new. As always, I was the first to arrive. Another first. The parking lot was deserted, and I was happy for that. I hate to admit how scared I was but that was the truth of it. I was terrified. Yes, I?d braced my staff as best I could but that did not mean that they were truly ready for the reality of seeing me in a skirt. How many of life?s little moments are that way? Haven?t we all studied for a test only to fail the damned thing? Would I fail at what I?d sent into motion? I hoped I wouldn?t. Peyton and I had planned and discussed, sometimes for hours at a time, and my staff had all given me words of either encouragement or apathy and either one was fine as long as there wasn?t a mutiny. I walked across the parking lot feeling the cold air riding underneath my skirt. The sun seemed unusually bright as if God was shining a spotlight on me, making sure that no one would miss the show I was putting on. Even with the sun shining down I could feel a coolness inside my skirt where a few inches of bare thigh was left uncovered. My stockings covered most of my legs but there was a good five inches or so that was left bare and I could feel the cool morning on that naked skin. It was a tantalizing feeling that left me trembling in nervousness. Yes, I was scared and for now the office was empty. How would I feel after my staff arrived? I made it inside and after making a cup of coffee I went to my office and shut myself inside. I wouldn?t be able to hide. In fact, I planned on calling a meeting and introducing myself, my new self, to the staff. Peyton and I had discussed it and, well, you can?t call a woman Mason. I had needed a new name to go with the new me and I had to introduce her to the office. I heard Gayle before I saw her. My first test. She knocked and even though I wasn?t feeling ready to meet her as I was dressed, I did not really have a reason to hold off on it either. ?Come in.? Did Gayle hear my voice crack? I?m sure she did. ?Mister, oh,? one hand came up to cover her mouth. She let out a gasp, her eyes went wide, and then she giggled. I didn?t expect a giggle. I did expect people to laugh although I hoped it was behind my back and not to my face. I thought I looked good. Definitely passable even if I was a little taller than most women and maybe a few pounds heavier. I wasn?t exactly svelte, but I wasn?t fat, either. I was an average man of average height and weight making me just a bit heavy for a woman. Hell, I was wearing a size twelve skirt, so I knew I wasn?t that heavy. My makeup was perfect, Peyton had made sure of that and my wig was combed and styled, and I thought it looked great even if it was hot and a bit itchy. I frowned at Gayle?s giggle. ?What?? I said. She stifled a fresh giggle. She coughed, trying to hide her merriment, ?I can?t call you mister anymore,? she said, following that up with a fresh bit of laughter. I smiled, ?No, I guess you can?t.? ?Well, then, Miss Sweet, I take it today?s the day.? I nodded, shrugged my shoulders and then did both at the same time. I was having second thoughts and third ones and even more after that. So far only Gayle had seen me. It wasn?t too late to race home and change. Put this whole situation behind me. Maybe Gayle would forget about it and even if she didn?t, I didn?t think she?d bring it up all that often. ?Stand up, let me see you.? I stood. I didn?t even think about it. Was I so submissive that when I heard a command, I had to obey with no thought involved? Maybe or maybe I needed to be judged. If Gayle said I passed muster, then maybe I did. Wasn?t Peyton obligated to say I looked good? We were dating; we were a couple. White lies were expected but Gayle didn?t have that connection that Peyton and I shared. The one that made us want to spare the other?s feelings. ?Turn around.? I did a pirouette. ?I?m amazed, Miss Sweet,? she said though I couldn?t tell if she was toying with me or if she was truly impressed by how I turned out. ?You look like a woman.? For this first test, that was the best grade I could have received. ?Thank you,? I said, meaning it. I gave a small, serious smile, ?Do you really think I look okay?? ?Just like a woman,? she laughed, ?fishing for a compliment.? She kept looking at me, her eyes taking in my shoes, my skirt, my pinstriped blazer. The way my faux hair framed my face; the color of my eyeshadow and the bright, glossy pink of my lipstick. She studied me, smiling and shaking her head. ?I swear, if I didn?t know any better.? She ended by bringing her hands up as if in surrender. ?You must really like her to do all this,? she said. I did really like her but that wasn?t why I did it. Or at least it wasn?t the whole reason. ?I didn?t do it for her.? Gayle looked at me skeptically. I didn?t owe her an explanation, did I? Maybe I did. I was taking a big risk but wasn?t I also risking her livelihood? There was a chance that this could blow up and lead to consequences that neither Peyton or I had foreseen. The what ifs and the unknowns led me to believe that maybe I did owe Gayle an explanation. Maybe I owed the whole damned company one. Myself most of all. ?Set up a meeting at ten,? I said. ?All hands. I think I need to introduce myself.? Gayle nodded and turned to leave. Before exiting my office, she said, ?you need to work on your voice. You don?t look like Mason, but you sure do sound like him.? She was right. Peyton and I had worked on my voice a little bit in preparation for this terrifying day, but I guess when you were used to being one person, the person you?d always been, then it was hard to be someone different. For now, I was an actor playing a role. In time, maybe, the new me would be the real me but for now I was Mason pretending to be someone else and maintaining that persona would take real work and some focused concentration. I raised the pitch of my voice and added a soft breathiness, ?like this?? Gayle nodded. ?Better. You sound weird. It needs some work.? In my girlie voice I could only agree. ?It?s a work in progress.? ?Move your hands more. It?ll help.? And it did. Moving my hands seemed to free up something in me that made my new voice come out a little softer and more animated. I sounded more real. I guess that?s the best way to describe it. I did some work until ten and then it was time to introduce myself to the staff. They?d known me for a while, some of them for nearly a decade and while they all knew this transformation was coming, I don?t think they could truly be prepared for it. Still, thinking about it didn?t do me any good. I was committed. The conference room was packed. Gayle had gotten just about everyone in the company to attend the meeting. She was good and for a moment I hated her efficiency. Not that it would matter. Even if half the staff was present before the end of the day everyone would know what I was doing wasn?t just an idea that I?d discussed. It was a reality. I entered the conference room, hearing the clickity-clack of my heels on the tile. I heard gasps and whispers and two different people coughing. I heard papers rustling and what I was sure was the shutter of a camera. I wanted to look, to see who had taken my picture but I kept my attention focused on the front of the room. Looking behind me would show everyone that I was just as terrified as they were even if it was for very different reasons. I paused at the podium that Gayle had set up. Behind me the whiteboard was empty. To my right the blinds were pulled open letting in far too much sunlight. God was still keeping me well lit it seemed. ?Good morning,? I said, moving my hands as Gayle had suggested. My voice cracked, and I hated myself for it. I tried again, ?Good morning, as you can tell I?m a little bit nervous.? The laughter that came back was every bit as strained as my voice. ?As you can see,? I stepped to my right, no longer using the podium for cover. If I was going to do this, I had to do it fully, ?I finally decided to do that which I?ve been discussing for a few weeks now. Gayle asked for an explanation and she was right to do so. I owe her one and I owe it to each of you as well. For as long as I can remember I?ve had this need to wear clothing that didn?t belong to my outward gender. It really isn?t much more than that. No, I don?t want to become a woman. No, I?m not gay,? I thought of Peyton and of all the things we?ve done, ?not even a little bit. I just have this need to wear women?s clothing. I?ve been doing it for as long as I can remember, since my early teens. Every day since I?ve opened this company, I?ve worn one article of female attire or another. It?s escalated, as you can see.? I scanned the faces staring back at me. Some wore bemused smiles, like I was a young child trying to get away with something. Others wore grins and smiles and were nodding. A few were frowning. ?Nope!? I turned as Jack climbed to his feet. He was one of my best salesmen, I think I mentioned that before, and seeing him stand and start to flee the room stung just a bit. He and I had joked about what I was doing, and I had thought he would be okay with it. The tone of his voice and the angry look on his face told me that I had read those earlier conversations wrong. ?Jack?? ?I quit!? He didn?t say anything else. He just left the room. I stood next to the podium, shaking my head, feeling angry and ashamed. I called after Jack and a moment later I called out after four more employees. ?Anyone else?? I asked. ?There won?t be any hard feelings and I promise glowing recommendations.? Three more people took me up on that offer. By the end of the day I?d lost over a third of my staff. I hadn?t expected it and it hurt. These were good people and just the thought of working for me as I now presented myself was more than they could take. Did that reflect poorly on me or them and what did it matter if the results were the same? I finished talking to the staff that I had left, truncating what I?d meant to tell them, and went to my office to pout or mope or cry. I couldn?t say which; maybe all three. I tried calling Jack on his cell phone, but it went straight to voice mail. I left him a message to call me back knowing that he wouldn?t. The angry, disgusted look on his face as he exited the conference room told me all I needed to know. Jack wouldn?t be coming back. By the end of the day I learned he?d taken some of my customers with him. That hurt but not as much as that look he?d flashed as he?d left the room. The look of hate. ?How?s it going?? Gayle was standing in the doorway, holding a fresh cup of coffee in her hand. I shrugged, ?I?ve been better.? She smiled but her heart wasn?t in it. ?I bet. You did the right thing, telling us,? she said. ?Thanks. I didn?t expect that reaction.? ?No?? I could hear the incredulity in her voice. I shook my head, ?It wasn?t a secret. I let everyone know it was coming. I spoke to Jack about it. I remember him laughing when he asked if it was okay if he hit on me.? Gayle took a sip of her coffee. Funny, when I saw her with it, I thought it was for me. ?You can?t predict everything, Mason.? She looked at me, ?weren?t you supposed to tell us your new name?? I hitched a weak little snort. ?So much for that. Jack walking out really surprised me.? ?So what name did you pick?? The excited tone of her voice perked me up just a bit. Someone wasn?t disgusted by what I was doing. Gayle seemed genuinely interested and not put off at all. I respected her for that. ?Peyton kinda picked it for me,? I said. ?We?ve talked about it, a lot. One weekend she called me every girl?s name she could think of as if she was tasting them, seeing how the felt on her lips. She called me everything from Amber to Yolanda. ?Brittney, can you pass the sugar please??? I did my best to sound like Peyton not caring that I failed miserably. ??Where should we go for dinner, Phyllis?? Each name she tried that she liked she used a few more times. I asked her if I got a say. ?Nope!? Then she stuck out her tongue.? I laughed at the memory. ?Why not? I asked her. ?When does anyone pick out their own name??? ?So, what did she settle on?? ?Louise. It?s a play off my middle...? ?Louis, yeah, I know. I?ve worked for you a long time, Louise.? It was the first time I heard the name spoken by someone other than Peyton and I liked the way it sounded and that bothered me a little. I?m not exactly sure why. Or maybe I did. It made it real in a way just wearing my lovely pinstripe suit did not. I put a name on it and as anyone who?s seen Toy Story, names have power. Ask Buzz how he felt when Andy stenciled his name on Buzz Lightyear?s foot. Hearing Gayle say my new name, my feminine name, somehow solidified what I was doing. Changing one?s clothes was one thing; changing one?s name was something else entirely. Something far grander. She said my name a few more times, growing into it. I liked how it sounded. Still, I was bothered by it. The finality of what was happening seemed to clamp down on my thoughts. I wasn?t just wearing women?s clothes to work, satisfying some rising fetish, I was taking a woman?s name and presenting myself as a woman. I didn?t want to become one. I was telling my staff the truth when I explained that to them. I didn?t want to take hormones; I didn?t want to have some disfiguring surgery ? having things added to my chest or taken off below; I just wanted to wear the clothing that both Peyton and I enjoyed, and I wanted to do it in a way that minimized the upheaval my coming out had already wrought. I failed at that. It was enough to make my head hurt. ?Don?t worry about Jack,? Gayle said, taking another sip of not-my coffee. ?How can I not?? ?You had to know that not everyone was going to be on board, right?? I had known, of course. It would be foolish to think otherwise and except for what I was currently doing, I did not think I was a foolish man. Hadn?t Peyton called me foolish? She had but that had been playful and light unlike my current, racing thoughts. Thoughts that were far too dark. I shrugged, ?I know, but Jack? Really? We?d joked about it.? Gayle said nothing. Then she said, ?shit.? I looked up at her and at the woman walking up behind her. Gayle had seen her first and I wish I hadn?t seen her and even more than that I wish she hadn?t seen me. ?Oh, my God, what a sissy,? Linda said. She had her phone out and was snapping pictures. I could hear an imaginary shutter cycling as she took each photo. It was the same sound I had heard walking through the conference room prior to that failed meeting. She had a grin on her face that was part predatory and part amused. Her eyes were wide, looking at me with the same intensity a starving man eyed a steak. ?Linda? What the hell are you doing here?? She looked at me some more, snapping another dozen pictures. ?Put the phone away.? Linda ignored me. It wasn?t like she every listened to me anyway, but this was worse. This was intentional. She was enjoying my embarrassment and the way I tried to hide behind my desk while holding my arms up as if my hands could block the lens of her camera phone. I yelled at her to leave. I ducked even lower, trying to hide myself away from her phone. Linda stepped past Gayle to stand next to my desk, getting even better pictures. ?Oh, this is priceless,? she crooned. She stopped taking pictures and a moment later, when I thought the worst had passed, I recalled a valuable lesson. Things are never so bad that they can?t get worse. I think I read that once in an old Calvin and Hobbes comic strip. I don?t remember exactly, but that was the idea and at that moment, when Linda stopped taking my pictures that bad got so much worse. Linda played with her phone and a moment later I heard a little sound. One I recognized. It was the sound the phone made when a text was sent. Linda hadn?t just taken my pictures. She did much worse than that. She shared it. ?Who did you send that to?? I demanded. My hands were moving, as Gayle had suggested, by they were flailing in impotent agony. My voice was full-on Angry Mason. A tone I had used with Linda far too often during our demise. She laughed, ?Oh, sweetness,? she said, making me wince. When Peyton called me that she was being kind and caring and playful. With Linda it was malicious. She had started calling me that after catching me in panties the first time. Sweetness or sissy or Nancy or faggot. Mostly it was the play on my last name and hearing it again, and the way she said it like a bully taunting a much weaker kid, grated on my nerves, ?I sent it to everybody.? I heard Gayle demand that Linda leave before she ?called the cops,? but Linda ignored Gayle every bit as much as she had discarded my plea to put her phone away. ?What do you mean?? I heard my own cell phone beep. The first of a long line of texts coming in. Then it exploded in a cacophony of incoming texts. For a few long seconds it seemed that my phone would never stop bleating. Flashing a grin full of teeth, she said, ?my parents, your parents, your two sisters, pretty much everyone you know. Well, maybe not everyone, I didn?t have the time for that. Yet.? I fell into my chair. I knew that most people would find out eventually, that was inevitable, but I hadn?t expected it to come at the malicious hands of Linda and in one quick, angry swoop. My phone beeped again. And again. The sound of my phone seemed to echo, not in the room, but in my heart. What were people thinking? What were my parents thinking? My sisters? Who had to know by now that I?d swiped their panties when I was younger. What would they say? My phone announced its presence again, demanding that I look but I was too afraid to even glance at the screen. My head would jerk towards the phone every time it chimed but I couldn?t force myself to reach for it. There were too many problems coming in and maybe too much damage. ?Why are you even here?? ?Jack called me, and I had to see this for myself. I always knew you were a little sissy, you and your damned panties, but this, oh, Sweetness, this is too much.? There it was again, the same word Peyton called me only coming from Linda it didn?t sound appealing. It sounded like something that growled and bit and maimed. And killed. ?You?ve had your fun. Just leave.? Linda gave me that predatory grin again, ?I?m not even close to being done with having fun.? She rolled her eyes like I had said the dumbest thing she?d ever heard. ?But, yeah, I?m leaving.? She brought her phone up and took a few more pictures before I could even think to shout at her to stop. ?I?ve got some more texts to send and a few posts to make on Facebook. You?re still on LinkedIn, right?? ?Please don?t.? ?Why, Sweetness, I think that?s the first time I heard you say ?please? in over two years. Fat chance, sissy.? She spun around, glowered at Gayle, ?how can you work for this pansy?? ?Easier than working for you.? Score one for Gayle. She deserved a raise. She would get one. Linda made some derisive snort and then left the office to do more damage. I had gone over countless scenarios about my dressing like a woman at work. Being outed to the world before lunch had never entered my mind. Linda coming, and wreaking havoc hadn?t entered my thoughts either. My phone beeped again. The tones were coming less frequently but they were still coming in and when Linda followed through on her threat, I knew it would be bleating even more. ?Are you okay, Louise?? I started to say something, paused, closed my mouth, opened it again, shook my head, and closed my mouth again. Finally, ?I will be.? That much was true. No matter what happened I would be okay. I had Peyton and that was enough. I thought about that for a moment. My world was collapsing, and my thoughts went to Peyton and how no matter what she would support me and be there for me. She was solid and strong and on my team. How could I not be okay? I looked up at Gayle, nodding, ?Yeah, I?ll be okay.? She looked skeptical, ?you sure?? I smiled, and it was genuine. ?Yeah. I mean it. Thanks, Gayle. Loved what you said to Linda, by the way.? ?She?s such a bitch!? It was the first time I laughed that day and it felt good, my face rising in a smile. Gayle went back to work as the office phone range. My smile faded when Gayle transferred the call. Most of my staff had been ready for my debut, save for the ones that left. My clients were not. Looking back, I find it funny that I barely gave any thought to what my clients would say, assuming that since I rarely met them in person then they?d not really concern themselves with what I was wearing. I?d been having such a good time with Peyton and my staff, while maybe not supportive, were at least acceptable to the idea, so when Gayle announced that Walter Smythe of Smythe Hardware was on the phone I didn?t think about what I was wearing. Maybe I should have. ?Walter,? I said, not hiding my voice. Gayle was right about that at least. My voice didn?t even come close to matching how I was dressed. The tone of my voice, the timbre, belied how I looked. If I were a print ad I?d be out of focus. The conversation was brief. I?d lost a customer. By the end of the day I?d lost over half. The first wave had been the ones that Jack had stolen; the final crescendo by the ones that were too close-minded or too prejudiced to hire an advertising firm run by ?a damned sissy,? or a ?flaming faggot,? or my least favorite, ?a pussy.? My thoughts of growing the company were shattered before the end of the day. Now I?d have to hustle to make up the ground I lost. I refused to release any of my staff for my actions. I?d take a cut to my own considerable wealth before I let that happen. In time, I was sure, my business would grow again. That led to a thought, which led to another. I made a few notes and finally, with the end of the day approaching, I picked up my cell phone. It was time to see what I didn?t want to see. True to hear word Linda had send the most damning pictures of me to my parents, my sisters, my friends, her friends, pretty much anyone that knew me before I started dressing like a woman. Most of the texts were derogatory and I knew I?d lost a few friends as I read their demeaning comments. The ones from my mom was sweet: What shall we call our new daughter? My sisters were equally supportive: It?s about time, from one, and Where did you get that blazer? from the other. Marie finally confirmed what I suspected all along. After the It?s about time, she followed that with: I guess you have your own panties now? That made me smile even if it was a weak one at best. Leaving the office for the day I had deleted about twenty-five contacts from my phone. I?d never hear from them again. That stung a bit, but the pain was eased by how many people either accepted or supported what I was doing. With them and Peyton it would be more than enough. Epilogue One Last First I mentioned having my last first date. That life was full of firsts and just as many lasts. The day Linda had released nuclear Armageddon on my life was the last day I ever saw her. Following our divorce, the day we?d both stood in front of a judge with our lawyers by our side should have been the last day I had laid eyes upon her, but life has a way of intermingling surprises between its firsts and lasts. She had come marching into my office with vicious animosity and had set my life on fire, before marching out the door just as fast, never to be seen again. Arriving home that night I waited for Peyton, texting her brief snippets of my day. At that point, feeling defeated, ashamed, angry, scared, frustrated and who knows what else had left me longing for something positive, something that I could grasp onto for support and comfort and that something was a someone. Peyton. Since the day I?d met her she had been there for me. She pushed me into going to work dressed as a woman, but I wasn?t just any woman, I was her woman and that possessiveness made it something far grander. She came rushing into my house and raced into my arms. I hugged her, clutching her like a drowning man grasps a life raft. My hands dug into her sides and I felt the tears on my cheek moisten the shoulder of her scrubs. ?It?ll be okay, Sweetness,? she cooed and just hearing her say her pet name in that kind tone she had seemed to overpower the angry way that Linda had said it hours earlier. How could one word, spoken by two different women, have such differing meaning? ?Tell me what happened.? Her voice was soft and sweet and full of warmth, compassion, tenderness and concern all at once. I replayed the day, leaving nothing out. Why should I? At that point I had no secrets from Peyton. None at all. I paused long enough to ponder that. Linda had known about my panties but not that there were times that I thought of wearing more. I had kept secrets from Linda and never once had I thought of hiding anything from Peyton. There was something to that. Something powerful, like I knew before I really knew that Peyton and I were destined for the long term. That I?d grow old with her and she with me. I told her about Jack and the disgusted look on his face as he stormed out shouting, ?I quit!? I told her about Linda coming in and assaulting me with her phone, taking damning picture after damning picture and sending them to my parents, my sisters, my clients. I told her about Linda posting the pictures on her Facebook page and linking the photos to my LinkedIn account. ?Before I left today not a single person who knows me was kept out of Linda?s damned loop.? Peyton held me, cooing into my wig. I let her hold me taking the comfort she was offering. I felt the stress of the day diminish; it would take months before it faded fully, but before we stopped for dinner, I was feeling better and the looks Peyton gave me told me that I had not weakened her at all. That old saying came to mind, something about a problem shared was a problem halved, but seeing how Peyton helped me without showing so much as a nick in her armor told me that maybe the math was a little more lopsided. A problem shared was a problem resolved seemed more accurate. I told her about the customers I lost, first to Jack and then to prejudice. She took it all in, comforting me with a word or a touch or a smile or a kiss. ?It?ll be okay,? she said as we washed the dinner dishes. ?You?ll bounce back from this, easy-peasy.? ?How do you know?? ?Because I know you, Sweetness. I know the man you are no matter what you?re wearing. I know the compassion you share for your staff; I know the resolve you possess. I know you and you?ll get through this and come out even better.? I wanted to doubt her but there was a conviction in her tone that gave me pause. I had built my business from nothing and it had made me wealthy. I enjoyed what I did, and I was good at it. Maybe Peyton was right. So what if I had to build anew. The staff that remained were loyal and good and my reputation was solid. The customers that left were closed-minded and maybe it would be good to branch out in a new, forward-thinking way. It?s not like I had a choice. You can?t change the past, but you could look to the future. Over the next nine weeks my business solidified. The idea I had had after the mass exodus had been simple. I advertised myself. I poured a bit of money back into the company and ran a few print ads coming out as Louise. It seemed to work. I gained two new clients and hired a new salesman. Her name was Meredith and she had just left one of the big companies in New York. You know the kind, the ones who make commercials for the Super Bowl. She had just transferred to the area and needed a job and my outfit was the only one she wanted. She chose me because of the way I dressed. ?My wife is going to love you, Louise,? she said following her interview. I couldn?t want to meet her. After hiring Meredith my business grew again. Six weeks after hiring Meredith I was back to needing to expand my staff again. Meredith helped with that, too, brining in clients from her old big-city business. It turned out Peyton had been right. Rebounding had been easy-peasy. Mostly. At the onset I had lost a bit of sleep but that had now passed, and the future looked bright. I had thought going to work as a woman would be the biggest of firsts. It wasn?t. It was the second biggest. With my business back to a new, better normal and my staff no longer phased by how I dressed, and my personal life damned near perfect, I had a revelation. I was sitting in my office, working on a proposal for a new print ad for deodorant when it hit me. My mind had wandered to where it always did when I was working on autopilot: Peyton. What had started out with a deliciously wicked introduction had blossomed into the best relationship of my life. Peyton, more than anything else, was the most important thing in my life. If my business hadn?t recovered, I know I would have been okay because Peyton was with me. Casting aside thoughts of deodorant I picked up the phone. After work I drove to Peyton?s house. She was still in her scrubs. I was wearing a cream-colored blouse with a dark maroon skirt. Two strands of pearls encircled my neck and matching earrings adorned my lobes. I no longer wore a wig. My own hair had grown out long enough that I now had bimonthly appointments to get it coiffed and styled. Next week I was going to add some auburn highlights because Peyton had seen the color in a magazine and decided it would look good on me. And since she was still in charge, and always would be, my hair would be changed to suit her mood. I was her Barbie doll and I was okay with that. ?Go change,? I said, ?we?re going out.? Peyton went to change. She came out of the bedroom in a simple floral dress that ended just above the knee. She was wearing two-inch heels. It was another one of the rules she had put in place. Not only was my cock still trapped in its prison, but now it was mandated that whenever we went out my heels had to be higher than hers. She got a thrill out of that and to tell the truth, so did I. In fact, my lowest heel was still taller than Peyton?s highest. I drove to the restaurant where I?d called ahead for a reservation. It wasn?t exactly a five-star restaurant, but it was clean with good food. It was same restaurant where Peyton and I had had our first date. She sat opposite me, the little candle on the table sending soft shadows across her lovely face. Brian didn?t wait on us this time; we had a waitress named Kathryn. She was every bit as attentive as Brian had been so many months ago, but I didn?t really notice. Peyton smiled at me, ?what?s on your mind, Sweetness. You?re acting strange.? ?Am I?? She nodded but kept smiling, ?yep!? I licked my lips, tasting my lipstick. I smiled back at her. I reached out and took her hands. ?I was thinking about you today.? She let out a little laugh. I felt her foot slide up my leg. I knew what she was thinking, ?I bet you were. I wonder if our panties match?? Her fingers tickled my wrist I let her foot toy with my leg. ?I was. I think about you a lot to be honest.? She beamed but said nothing. One last first came spilling from my painted lips. ?I love you.? It had finally dawned on me at work, working on a new advertisement for a woman?s deodorant, that my feelings for Peyton weren?t imagined, but real and they surpassed anything I?d ever felt for Linda. I know that wasn?t fair to my ex-wife, but it was honest and sitting in that booth, I was feeling true, honest emotions. I had been for a while. Except for our daughters, it was the last time I told someone I loved them for the first time. Peyton didn?t hesitate. She smiled and said, ?I love you, too.?