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This story follows a character introduced in "Elise Plans a Wedding", but it stands by itself. Prologue: Confused Looking back at things, I'd have to say that I've spent most of my life in a continual state of confusion. In fact. I am confused at this very moment. I seem to be in a college classroom, sitting in a circle, with about a dozen or so women. I think. Actually I'm a bit confused about that. I'm quietly staring at my feet, happy now that winter is over and that I can enjoy wearing sandals again. As I admire my pedicure, a very attractive woman walks to the middle of the room, welcoming us. She is saying that before she begins her presentation, she would like each of us to stand and introduce ourselves. I'm still staring down at my feet when I feel a jab in my left arm. Startled, I sheepishly stand up and say, "My name is Penny, I am a lawyer, and this is my first time here." When I sit back down, the woman on my left, the one who jabbed me, grabs my left hand and squeezes it. I looked down at her feet, then back to mine. I lean over and whisper in her ear, "Sorry, I did a really crappy job on your toe nails. You did so much better on mine." She gave my hand another squeeze and told me, "We'll practice some more." The ensuing lecture and discussion on hormone therapy is confusing. My roommate, Krista, had asked if I would come with her to this. I wasn't sure if I wanted to. You see, this is my problem. I have trouble making a decision. Internally, I argue with myself, evaluating all my options until I've totally confused myself, unsure of what to do. It's also probably why I'm shy around people. So, I usually end up letting someone else decide for me. Krista is concrete sequential. She gathers information, evaluates it, makes a decision, and moves on to the next step. I guess that's why she's an engineer. She decided we'd be roommates after evaluating our "situation". To me our "situation" was confusing. Until I met Kyle, I was pretty sure I was a straight guy named Peter. Kyle decided that the data showed that he was likely a transgender woman named Krista who liked men. So she concluded that it was therefore logical that we should date. After a while, apparently the data indicated that we were a couple. You can't argue with facts, she would tell me. Not that I'd try. I'm not very good at arguing. In truth, it was a lot more complicated than that. But that's how Krista likes to tell it. Oh, in case you are wondering how a lawyer is bad at arguing, I only became a lawyer because I lost an argument with my parents (both attorneys themselves) over what I was going to be when I grew up. Note that I lost that argument at the age of eight. Also, I work for a publishing and public relations company, handling contracts. I just sit in my little office by myself. No legal colleagues forcing me to debate fine points of the law. No arguing case law before a judge. I've never even set foot in a courtroom. Anyway, after hearing all about HRT and listening to a prolonged discussion on drug options and dosages, I am totally lost. I suppose I had a somewhat sheltered upbringing. You could probably call it a privileged upper middle class upbringing. We were a progressive family in a large town. But it was hard to understand diversity in a place that seemed totally devoid of it. By the time I graduated from law school, I only had tenuous a grasp of gender diversity. It was a wedding that brought Krista and me together. It was also where I first knowingly encountered a transgender woman. Make that several transgender women. In my naivety, I assumed that their outer appearance was the result of expertly applied makeup and well designed clothing. The two trans women in my life are like that, almost always wearing a dress, almost always wearing makeup. It was when Samantha, the lecturer, showed "before and after" photos of herself and a few of her friends, that I began to understand what really was involved in being transgender. And what Krista was contemplating. I now realize I have no idea who in this room is transgender and who isn't. My naive visual stereotype is wrong. My concept of being trans is incomplete. I am now fearful of saying something offensive or embarrassing. What if I ask someone how their transition is going, only to find out I am talking to a cis woman, here to support her transitioning spouse. So now I'm just walking around, following Krista as she socializes, trying not to say anything at all. "Penny, honey, come here and say 'hi' to my oldest and dearest friend, Sophie," Krista gushed. We shake hands. We give each other a subtle smile. She is the reason I'm standing here in a dress holding my girlfriend's hand. Chapter 1: How I Met My Future Roommate I started working a little over a year ago, right after law school. I was not at the top of my class. I could barely see the top of the class from where I was sitting during graduation. But on the plus side, I only had one job offer, so I didn't have to make a decision where to work. The people at my company were very friendly and inclusive. I felt fortunate to have gotten a job there. Although it was actually a little overwhelming at first. One of the company perks was the ability to take a few hours a week to do volunteer work. If you supported a particular charity, community project, or social issue, you were encouraged to do so. As a new employee, it seemed like I was constantly being approached and asked if I was interested in their particular cause. Because of my inability to respond decisively, I started to worry that I would eventually just say yes to get people to stop asking. But that wouldn't be fair to them, their cause, or to me. But I did like the idea of volunteering for something. My job can get lonely and my social life was nonexistent. So instead, I started scanning the company bulletin board looking at the "volunteers needed" postings, trying to find my own cause. Finally I saw a posting for a fundraiser to support homeless LGBTQ kids. Perfect, I worthy cause that I honestly could support. The notice said to come to a meeting at four o'clock in the conference room next to the CEO's office. I was one of the last people to arrive. Entering the room, I saw eight or nine people. Among them was a strikingly sophisticated woman who approached me saying, "Hi, I'm Rebecca, and you are..." "Peter," I replied nervously because I now recognized her from a photo hanging in the company lobby. It was the CEO." "Peter, thanks for coming. It's good to have a new face here," she told me. I found out that this group has been a part of an annual community wide event. Everybody else had volunteered in the past, using some skill like preparing food, soliciting donations for a silent auction, running an auction, that kind of thing. "So Peter, what kind of hidden talents do you have?" I was asked by the CEO. As I thought silently, she prompted me, "I don't suppose you've done any theatre or any kind of performing, have you?" "I did some fraternity skits in college, sang in a choir, but nothing serious," I said. The expression of her face changed to a broad smile, "Excellent!" she said. "I want you to call this number," she brought up a name and phone number on her phone, "and tell Kyle that you are a volunteer for the LGBTQ fundraiser. Kyle is in charge of the entertainment and he really needs help." That evening, back in my tiny loft apartment, fiddling with my phone, I went over the pros and cons of calling this guy. If I don't call, the CEO of my company will be disappointed. Not that I could be fired, this was voluntary after all, but still, not a good career move. Also, I would be disappointed. Disappointed in myself because I was afraid that I would be asked what kind of skits my fraternity put on. Then I would have to admit they were pretty sexist and that because I was the smallest fraternity member, I was always cast as the girl. Sometimes it was imitating some girl on campus that they hated, other times, a famous woman they despised. I almost felt abused afterwards, like I was the actual girl. As soon as I remembered that this fundraiser was for kids who actually had been abused, I dialed the number. Kyle was effusive on the phone, thanking me for volunteering and asking if I would come to a Saturday morning meeting with the entertainment committee. That morning I arrived at a large warehouse, converted into some kind of club. The club wasn't open, but there was a guy at the door who let me in when I said I was here for the LGBTQ fundraiser. The place was empty except for five guys sitting at a table next to what appeared to be a stage. "Welcome, welcome, welcome!" yelled a slender man, mid twenties, probably about my age. He stood up and ran over to me. "You just have to be Peter," he said. "Look everyone, Peter is here." Kyle, who was obviously gay, gave me a little hug. Oh wait, please understand that I wasn't being judgmental. That's how he introduced himself, "Hi, I'm Kyle and obviously I'm gay. Out and proud! Come meet our gay little band." "So Peter, Rebecca texted me that you have some performing experience, tell us all about it," he said. Rather than being repulsed by my fraternity antics, Kyle said, "Looks like Rebecca sent us a winner girls." I looked around the table and everyone was nodding their approval. Once again, I found myself in a state of confusion. Sensing my discomfort, Kyle asked me, "Rebecca did tell you that we always do a drag show for the fundraiser, didn't she?" When I didn't respond, Kyle said, "Oh dear, she didn't! You're not even gay, are you?" I'm hurriedly going through everything I said to Rebecca. I didn't tell her I had dressed as a girl. I didn't mention anything remotely about my sexuality, that would have been highly inappropriate. I know these things. I'm a licensed attorney. I'm rapidly processing my options. It's not that I minded dressing like a girl, it was that the fraternity skits were demeaning to women. If anything, from what little I thought I knew about drag, it was a celebration of femininity. This could be sort of atonement for my past. "No, she didn't, but I think it might be fun. If you, do I say 'girls', don't mind, I'd like to give it a try." So began my life as a part time amateur straight drag queen. All of the 'girls' were working professionals in real life (except for Kyle who was still in graduate school). Each had developed their own drag persona. A financial advisor in the group suggested that I be called "Penny Stocks". I changed it to "Penny Wise" because I wanted her to be not just risky, but also to be carefree, a kind hearted spendthrift (you know, dollar foolish). I loved my alter ego. I was a completely different person in character. I could make decisions! I could interact with people without worrying about what they thought of me. I was a quick witted, brassy woman with orange hair, big boobs, and attitude. Unfortunately, none of those characteristics carried over to real life. Given my innate shyness and lack of decisiveness, I had trouble getting a date. This was particularly frustrating because eighty percent of the people at work are women. Granted, many are lesbians, but still you would think someone would be attracted to me. Other than Kyle. For sometime, I realized that Kyle might have a crush on me. I was the only guy in our little group that was close to his age. In fact, I was only two years older. The others were all much older, most in long term relationships, even married. Then, late last fall, things took an interesting turn. Friends of Kyle we're getting married and he asked us to help out. It was going to be at the club where we perform. When a blizzard hit, Kyle came to the rescue and performed the ceremony (thanks to an Internet web site). Rather than as his usual drag persona standing in front of the two brides, he was dressed as a normal woman would dress, and to my surprise, an attractive woman. By that time, I'd already visited the open bar more than I should have. As the festivities picked up after the reception diner, I watched Kyle dance with one bride, then the other bride, then with a couple of the bridesmaids. Dressed as "Penny Wise" I was not about to be left out. The minute he was free, I strutted out onto the dance floor, stood in front of Kyle and asked, "May I have the next dance?" "I thought you'd never ask," he replied. I kept staring at his face. With understated makeup on, it was the first time I saw how feminine he looked. We didn't speak. Just moved to the music. When it was over, I just said, "Thank you," and went to get another glass of wine. Half an hour later, Kyle asked me to dance. Same as before, we didn't talk, just moved to the music, only this time we held each other a bit tighter. We danced one more time before the evening ended. Afterwards, I went to the dressing room behind the stage and changed back to Peter. As I packed up my costume and paraphernalia, there was a knock on the door. "Can I talk to you for a minute?" an unfamiliar voice asked. I opened the door. One of the bridesmaids was standing there. "Sure, what can I help you with?" I wondered. "Well first, let me just thank you. You and the other queens pretty much saved the day. The blizzard might have ruined it without your help. But that's not what I want to talk to you about," she sounded serious. "I'm Sophie by the way," she said, shaking my hand. "Kyle and are I are friends. He's my oldest friend and very special to me. He was the only person I could confide in when we're we're kids. He was the only one who knew about my gender dysphoria. I know many of his secrets. I know he is attracted to one of his drag friends. I'm pretty sure it's you." "I'm pretty sure it's me too," I confessed. "Please don't hurt him," she said. "I ahhh, ....... I never ....... I ......." I kept stammering and was about to cry. "Oh my," she interrupted as I tried to collect my thoughts. "You're really confused about what happened, aren't you?" I nodded yes, "I wasn't expecting this. I really only know Kyle the drag queen. Watching him perform the ceremony, dancing, laughing, even crying, I saw someone I didn't know." I felt flushed. "Sophie, I'm scared. I think I'm attracted to Kyle. I think that's what I felt when we danced together. I just don't know which Kyle I'm attracted to. Kyle the man, Kyle the drag queen, or Kyle the woman." Chapter 2: Finding Krista A couple of weeks later, I got a surprise text from Sophie. She had asked for my number, saying something like "Maybe I can help you find out," before giving me a hug and leaving me confused and afraid in an empty dressing room. "Can we talk?" was all the text said. Fifteen minutes later I was seated across from her in a nearby coffee shop. It was a little disconcerting that she knew where I worked. "Thanks, I was nearby picking up some supplies for my shop. I was talking to Kyle last night. He's pretty confused," she said. Before I could reply, she continued talking, "Before you say anything, you need to know that I am not trying to interfere in your life. It's just that my friends are my only family. I assume that, from the wedding, you know that I am trans," I nodded yes, "and that's not easy. But I've been luckier than most to have supportive people around me. I even have a girlfriend." I sat listening to her, slowly sipping a latte.p "Anyway, I know it's been two weeks and I realize that what you said then, might not even be true anymore. But I think you should know that Kyle is having a lot of problems dealing with this." I looked down at the cloudy liquid in my cup, thinking it reflected my feelings. Then looking at the sad expression on Sophie's face, like she was prepared for me to tell her that, yes, my feelings have changed, but instead I told her the truth, "I still think I might be attracted to Kyle, but I still don't know which Kyle." Sophie sighed, leaned back with a small smile on her face, and took a sip of coffee. "Although, I will add, I have figured out that I am definitely not attracted to drag queen Kyle," I laughed. "Thank god! If you were attracted to that weird persona he's created, I'd really question your sanity," she giggled before almost spilling her drink. She then opened her purse and took out two slips of paper and handed them to me. "Remember, I am not interfering. But if you're so inclined, the first slip here has the address of a pizza place near the university. Kyle goes there faithfully every Friday night at six o'clock. If you want to see the real Kyle in his native environment, well that's up to you." "The other slip lists the hours that Kyle works part time tending bar. You already know the address, it's the club, the Cafe 101. Again, it's up to you. If you do go, look for Krista. I think you'll recognize her." With that, Sophie closed her purse, stood up, shook my hand, winked at me, and said, "Thanks for seeing me. Good luck Penny. Got to run now, bye!' Friday evening I drove over to the university and parked across the street from the pizza parlor and waited in my car. It was near the law library and I had eaten there a few times. It wasn't one of the party hot spots around campus. I remembered it as a hangout for nerds, with white boards for walls so students could solve equations while eating pizza and drinking beer. Promptly at six, someone resembling Kyle walked in. Only, this guy didn't have heavily moussed hair and pink framed glasses. I got out of my car and walked across the street. Once inside, I saw the place hadn't changed. Several students were scribbling on the wall. One of them was Kyle. I sat down at a small table and ordered a beer and watched in fascination. I was almost done with my beer when the guys working at the wall began clapping as Kyle wrote something, presumably the answer, on the wall and circled it. As he was high-fiving the others, he looked across the room and saw me. I lifted my beer to him and smiled. "Peter, what are you doing here?" he asked. "I needed to do some research at the law library. I used to stop here when I was a student." I partially lied. "Would you like to join join us? We're about to order a couple of pizzas. They're just a few classmates. We get together once a week and work on a research project together," he said. Then he changed his mind, "You know, never mind, we're not exactly a fun group. We never discuss anything other than this project. Can I join you instead." Kyle apologized to his friends, but they didn't look like they cared one way or the other. We ordered a pizza and another beer. Then we sat and made small talk. I couldn't believe this was the same guy. Where was all the flamboyance? This Kyle is a nice, shy engineering student. But certainly not someone I'd ever be attracted to. There was also another weird thing. I sensed he wasn't attracted to me either. The glint I usually see in his eyes wasn't there. We finished our beers, he went back to his friends, and I went home. As I drove, I had the strangest thought. Except for the first time we met for the LGBTQ fundraiser, he only sees me when I'm in drag. I waited a few days before I texted Sophie. We met the next afternoon at the same coffee shop. She knew about my brief evening with Kyle. "Kyle is confused too," she said. "Yeah, we were two shy, confused guys, we made a perfect pair," I grimaced. I was about to tell Sophie my humorous thought that maybe Kyle was really only attracted to me in drag when Sophie said, "I find it terribly interesting that it might be your drag persona that he's attracted to." "So correct me if you think I'm wrong, but you've eliminated all but the last option. You are attracted to Krista," Sophie theorized. "Ok, I haven't asked this yet, but who is Krista? I mean, I know it's Kyle, but..." I asked. "Just before the wedding I was almost dressing full time as my true self. I had just bought several new outfits and I was showing them to Kyle. I thought I was just being silly when I suggested that Kyle try one of them on. Well, ok, it wasn't totally silly because when we were kids, wanting to wear girl clothes was one of our shared secrets. Which obviously isn't a secret anymore." "Maybe it was me giving him the permission he never gave himself, but he really enjoyed" no that's incorrect, "she really enjoyed herself dressing up and putting on nice makeup. The name Krista popped into my head and she liked it." "It was Krista who you danced with." "Now I'm going out on a limb, I think that it's Penny that she likes. Not the drag Penny, but the Penny that you haven't discovered yet." Chapter 3: Finding Penny "Are you planning on going to the club and seeing her?" Sophie asked. "I was, why?" I asked. "If you are, I want to make a suggestion," she said. "I thought you didn't want to interfere." I answered. "Is a suggestion the same as interference?" she replied. "Do you want a legal opinion?" I asked. "Are you going to charge me? What's your hourly rate?" she asked. "Oh, never mind," I laughed, "you win. I just can't win an argument. What's your suggestion?" "Come over to my place before going to the club." "The reason being?" I asked. "You're a smart girl Penny, I think you already know." Krista was scheduled to work the four-to-ten shift the next day. I was headed to Sophie's place right after work. I wasn't expecting such an expansive apartment. Sophie went to beauty school, I went to law school. She has a luxurious apartment, I have tiny loft. If only I had won that argument with my parents, I might be living like this. Sophie was ready and waiting for me. "Hi, welcome to Sophie's House of Style," she greeted me, holding the door open. "Really?" I said, giving her a bemused smile. "Too much then? Sorry, come on in," she laughed. Maybe I was too quick to judge. Sophie had laid out several dresses in different sizes on the furniture. There were also several pairs of high heels lined up in rows on top of a dining room table. "My girlfriend has a boutique dress shop. She's letting me borrow these." Sophie pointed to the array of dresses. "I made an educated guess on the size range, hopefully one of these will be a perfect fit." I slowly walked around the room. "These are beautiful," I said picking up a navy blue lace dress, catching a glimpse of the price tag, "and expensive! Are you sure this is ok?" "Well, you only get to keep one, my treat," she said. "What about the shoes?" I asked, picking up a black sling-back pump that I liked. "Those are mine. I complemented Kyle once on the shoes he had on after a drag performance. I remembered him saying that he had borrowed them from you because he had broken a heel. So I hope these fit because I know they fit Krista." "Now before you try on anything, you need to shed as much icky male stuff as you can. I am going to draw you a nice scented mineral bath while you are getting undressed, " she ordered, "Follow me!" Sophie led me to her bedroom, handed me a pretty bathrobe and a pair of fluffy slippers with pink bows on them. Sophie went into the adjoining bathroom while I removed my clothes. I was waiting for her, naked underneath the soft fabric of the bathrobe. "She came back into the bedroom. "Don't be shy, let's see what we're working with here," she said as she loosened the sash and pulled the robe open. "Hmmm, nice body, you even have a few nice curves. Probably won't need any shapewear. Now take this," she said, handing me a razor, "get busy missy, it all goes. All of it!" "Even down there?" I pointed, a little embarrassed. "Yes. Don't you tuck? she asked. "I just use a gaffe, and then only for one outfit," I explained. "Well, when you see the adorable panties I have for you, you're going to thank me. Now go before the water gets cold." When I emerged from the tub, I was amazed how silky smooth I felt. It was such a liberating feeling. I wrapped the robe around myself and opened the door back to the bedroom. On the bed, Sophie had laid out a set of matching bra and panties. I caught myself gasping and shaking with excitement. "What is happening to me, Sophie?" I asked. "I hope you're simply finding yourself. Have you noticed you're not questioning yourself as much? You don't feel coerced do you?" she asked, "If you do, if you have any doubt, we stop right now." "No!" I immediately shouted without any hesitation. "I want this. And this doesn't have anything to do with Krista, or Kyle, or whatever. It only has to do me," I stated as affirmatively as anything I have ever said in my life. "Ok. Good. I totally understand," she said after giving me a hug. "Now sit here and we are going to see if we can make these pretty panties fit like they're intended, is that ok?. I smiled and nodded my approval. Let's just say it took us a few tries to master the tucking kit. But the results were definitely worth it. The panties slid on so smoothly. One more icky male thing removed, temporarily. I wished I could have done the bra a little more justice. Sophie offered to let me try a pair of her breast forms, but I was afraid of damaging them, so we just went with some inserts. Sophie didn't want to risk getting any lotion, makeup, or perfume on the dresses so the next task was picking one to wear. It wasn't easy. Sophie had chosen six that fit me like a glove. I insisted that she take a picture of me in each one, just in case I ever wanted to visit her girlfriend's shop later. After much deliberation, we both agreed a "little black dress" made the most sense. That narrowed the choice down to two dresses. A cute shift with lace sleeves won out. Besides, the sling-back pumps were supper comfy and went perfectly with it. After I pouted perfectly, Sophie said I could even keep them. With the outfit chosen, we returned to the bedroom where Sophie started on my toes and finger nails. Once I saw how cute she had painted my toes, I was wishing it was sandal season. While my nails dried, Sophie fit a wig cap on me and began working on my makeup. I'm used to seeing my self in drag makeup. It usually looks like I put it on with a trowel. Before she let me see the results of her efforts, she fitted a lace front, shoulder length, dark auburn colored wig on me. The results took my breath away. I never imagined that I could look like this. "Don't you dare cry," Sophie admonished me, "If you ruin that mascara I'll....." "Ok, ok!" I screamed. With the nails dried, Sophie handed me a package of nude thigh high stockings. These were way sheerer than anything I'd ever worn, so I took special care putting them on. They way they felt on my smooth legs was almost erotic (I was momentarily concerned about my tuck). With my lingerie complete, I stepped into my dress, slipped on my heels, turned to Sophie and asked, "Well, what do you think?" Sophie took my hand and pulled me toward a full length mirror on the door. "You tell me first," she said, "tell me what you see?" "Oh my god, is that really me? Is that really Penny?" I wondered. "I think it is babe. I think it is." Chapter 4: Finding an Answer "My gosh, look at the time! It's already almost nine!" I screamed. "Shit! Here take this purse. I put your lipstick and compact in already. Grab your ID and money. We've got to get going," Sophie exclaimed. "You're coming with?" I asked. "Have you driven in heels before?" she replied. "No," I said. "Then I'm coming with. I'll drive. I won't let Krista see me," she said. "You're going to watch?" I asked puzzled. "You bet I am. After all this work, I'm not missing the final scene!" she stated as a matter of fact, "I hope you don't have a problem with that." "Absolutely not girlfriend! Absolutely not," I laughed, grabbed my purse, took Sophie's hand and told her, "lead the way!" As Sophie drove me to the club, I was trying to assess what I was feeling. I certainly felt different. I felt liberated, I felt excited, I felt comfortable, I even felt attractive. I also felt vulnerable. Not unlike the way I felt when I was a girl in the fraternity skits. But I didn't feel any of the confidence and decisiveness that I have when I'm Penny the drag queen. At least not yet. It was just past nine thirty by the time we parked her car and walked to the front entrance. Sophie went in a took a quick peek, then flashed me a thumbs up indicating Krista was tending the front bar. I waited at the front door until Sophie was safely seated. When I showed my I showed my ID to Jason the doorman, it hardly phased him. Seems he's pretty used too seeing gender fluidity in action. "Ok, miss," he said shrugging his shoulders, what do I call you now?" "Penny. Just Penny," remarkably I said this with confidence. "I can remember that. Have a nice time Penny." I started a slow walk towards the bar, eying an empty stool at the end. I hadn't seen Krista since the wedding. If anything, she looked even cuter in her barmaid attire. I watched her smiling and laughing with her customers. I felt a definite stirring tucked away. There was no doubt which version of Kyle I liked, silently hoping that this was the true version. "What can I get you hun? she asked me when it was my turn to order. "I think a red wine. What would you recommend?" I asked, trying to sound somewhat feminine. Krista hadn't looked at me directly yet, but my voiced caused her to twitch a little. "Dry or sweet?" she asked, now staring directly at my face. "Dry," I answered. "Ok, I have something I think you'll like, be right back." I watched Krista, in her cute dress and red Mary Jane flats, stride over to the wine rack, occasionally glancing back at me. I saw her pull a dusty bottle from the rack, she poured a glass while still taking quick glances back at me. When she set the glass down in front of me, I could swear that I saw that glint in her eyes. "This is a very nice French Rh?ne. I think this might be what you're looking for," she smiled. Was that a double entendre? "Mmmm, this is very nice, excellent recommendation. What do I owe you?" I purred (at least that's what I was going for). "It's on the house," she said with a wink. "Excuse me, I have a few tabs to close out before my replacement comes. I continued to sit there nursing my drink. When I had the chance, I gave Sophie a subtle wave. I was also enjoying the sensuous feeling of crossing my nylon clad legs and letting my pump dangle from my toes. Apparently I wasn't the only one enjoying me doing this because I had two different guys ask if they could buy me a drink. Shortly before ten o'clock, Krista returned and took my empty glass and pushed it aside. "So tell me," she began asking, "what's your name." "Penny," I said demurely. "Penny, hmmmm, I know a girl named Penny. Don't tell her, but you're much prettier," Krista whispered. "Funny thing about Penny, I seem to keep running into her where I don't expect to. I wonder how that happens." "I wouldn't know. Maybe you shouldn't worry about things like that," I said. "You're probably right. I'm off now, perhaps you and I might share a drink somewhere quiet." "I would like that." I gently placed my hand on top of Krista's. "My place is very quiet, small and intimate." "Sounds perfect. I could meet you there. Just have to take care a some bookkeeping and check out." "Want the address? I asked. Krista thought for a second, pulled out her phone, and opened her contact list. "Ok, go ahead," she said. After I recited the address, Krista said, "Now this is strange. You're address is already in here. Do you have a roommate?" "I do. But he is terribly shy and boring, you wouldn't like him. I'm in the process of getting rid of him." "For good?" she asked. "I hope so." As soon as Krista left to check out, I ran over to Sophie. "We have to leave now! I'm meeting Krista at my apartment. We have to drive back to your place and get my car. Unless you want her to know for sure that your involved in this." "I rather she not know for now, because technically I violated her trust." The minute we arrived back at Sophie's apartment building I remembered that I left my car keys in the apartment. "Where in the apartment?" Sophie screamed. "The bedroom, I think I put them on the nightstand." "Stay here, I can run faster," she yelled. Only a few minutes later, she returned with the keys and a suitcase. "Here, I had put together a care package for you. This is filled with lingerie, outfits, shoes, stuff I don't wear any more. Also lots of makeup samples. Good luck sweetie! And drive safely in those shoes!" I beat Krista to my place by a good ten minutes or so. I stashed the suitcase in my closet (eager to explore its contents sometime soon), straightened the apartment up a bit, found my last unopened bottle of wine and my last two clean glasses, and set them out on the table by my couch. Next I grabbed my purse, dug out my lipstick and put on a fresh coat. I wanted them to look kissable because I was was planning on planting them on Krista the second the door opened. I positioned myself in front of the door and tried to strike what I hoped was a sexy come hither pose. Seconds later there was a knock on the door. I took a deep breath and opened it. Krista was standing there, holding the bottle of wine she had opened for me. "No sense wasting it," she said, holding up the bottle. I grabbed the bottle from her, dashed over to the table, set it down, turned and ran towards Krista, jumping into her arms, and pressing my lips tightly against hers. I can't begin to guess how long we stood there kissing, the door still open. At one point, out other corner of my eye, I saw my neighbor walk by (I'm probably going to have an interesting conversation with him sometime soon). Eventually we broke our embrace and moved to the couch. While I think we both craved more intimacy, taking it slow and starting to find answers to the several nagging questions we both had, seemed equally important. Krista broke proverbial ice, "You are beautiful and it's obvious I approve of this sudden transformation, but I guess my question is, 'why?'" My long and a bit rambling answer was essentially that I was trying to understand what was driving my attraction to her. However, in doing so, I had discovered things about myself that were going to take time to understand, but clearly I was on a path to becoming a different person. When I asked her the same question, her answer closely mirrored mine. Although I did have a follow up question, "Why the flamboyantly gay caricature when that doesn't seem to have anything to do with the real you?" "Defense mechanism," she answered. "I was teased and bullied in school for being smart, shy, and I guess effeminate. By high school, the jocks were calling me the 'f-word'. My one jock friend suggested I stop reacting and just go with it. I discovered the more flamboyant I acted the less interested they were in harassing me. I'd taken the fun out of it for them. I only fall back into it around old friends who are in on the joke or around the drag group." "Wait, are you even gay?" I asked. "Probably more bi-sexual. I've only dated two guys. I had a girlfriend in college for awhile." "So we can agree that neither of us is interested in a gay relationship between two shy guys. Right?" I said. "Right," Krista affirmed. "What about a lesbian relationship?" she asked. "Possibly. Maybe we should explore our relationship before labeling it," I said. "And when would you like to start this exploration?" she asked. "Definitely in the near future," I answered. "How far in the future?" she asked. "Oh, certainly no more than five seconds," I said while gently pressing my lips to hers. Chapter 5: Becoming Roommates Our first exploration was ....... Sorry, neither of us have been able to come up with the right adjective. We both agreed it was intensely erotic and that it left us wanting more. However, there was a lot of bumbling along the way. Since we both had experience making love to women, fore play was familiar territory for both of us. The kissing and slow removal of clothing had made both of us extremely aroused. When we got down to our panties, I found myself in unfamiliar territory. Krista lovingly told me not to be nervous, she would help me. I had been endlessly going over this moment in my head. I wasn't nervous. I had envisioned Krista slowly slipping her hand into my panties, smiling up at me, touching me for the first time. It was all going as I had imagined, until Krista slipped her hand in and found.... Nothing. I forgot about the tuck. Krista had to pull my panties off and start removing Sophie's handiwork. By the time my cock was free, it was not exactly in a state of arousal. Fortunately Krista knew how handle the situation. Soon I was having the most intimate moment in my life, watching her bring me close to orgasm. She rolled over on her back and tried to guide me so that I could penetrate her. Unfortunately, while I was attempting to enter her, I came. I was so embarrassed. Krista was so kind, assuring me it was ok. I now desperately wanted to make her come. For my first time, I was really enjoying the sensations of her cock in my mouth. But Krista wasn't enjoying it as much as me. I would get overly aggressive and almost byte her. Finally she took matters into her own hand, giving me my first taste of her. Over the next couple of months, our relationship reached the point where we wanted to see each other everyday. My lease on my tiny apartment was expiring soon. I began dropping subtle hints. I could tell Krista was playfully ignoring them. "You do know I'm going to show up at your door next week, hat in hand, lugging all my personal belongs, don't you?" I told her one evening, as we laid in my bed after making love (by the way, I was getting really adept at penetrative sex, giving and taking). "If you do, you'll be at the wrong apartment," she teased. "What?" I screamed. "I've been trying to negotiate a swap. A tenant on the first floor wants to move to a smaller unit. We take over his larger one at the end of the month." "We're going to have a whole extra room?" I asked excitedly. "Yep, I was thinking maybe a sex dungeon," she said. "You know Krista, sometimes I just don't get your sense of humor." "Ok, but kind of a dungeon. I was thinking a home office. That company I interviewed at, made me a job offer, starting right after I graduate. I'll be able to work from home a lot. And you could use it too on days when you don't have to be in your office." "Oh sweetie! Congratulations!" I yelled. "There is another advantage to this that I want to talk with you about," she said with some hesitation. "Ok, what is it?" "I'll be able to start working towards presenting as a woman full time. I can be myself working at home," she explained. "What happens on days when you have to be there in person?" I asked. "It'll be ok. Accepting the job was contingent on them accepting me. The HR person told me the company had an employee transition two years ago." Krista took my hands in hers. "What I need to know, Penny," she paused, "is this ok with you?" I didn't need to think about it, of course the answer is yes. But I took a long time saying it. I was thinking about my own situation. I could walk into my company's HR department tomorrow and tell them I was transitioning and they wouldn't bat an eyelash. For heaven's sake, the CEO is transgender. I thought I was getting better at making decisions. Apparently not. "Yes, absolutely! I'm so proud you," I finally said. At the end of the month, I moved in with Krista. I love my new home. A couple of months more and Krista had finished her masters degree and was putting our home office to good use. Shortly after that I started to feel depressed. I would come home after work in my "Peter costume" as Krista called it. I felt like I was trapped in a 1950's black and white sitcom, playing the clueless husband coming home after work, his wife greeting him wearing a dress and high heels. I usually head immediately for the bedroom and rid myself of my "Peter costume" and put on my "Penny costume". One night I was really tired when I got home and didn't change clothes. Krista made an innocent observation that I hadn't changed clothes yet and I snapped at her. I hated that I could ever think Penny was only a costume. It was right after that incident that Krista contacted a transgender support group. After a lot of cajoling, I agreed to go with her to a meeting. Chapter 6: After the Meeting During the ride home from the meeting we hardly said a word to each other. I already knew what Krista was going to tell me, that she wanted to start HRT. The longer we sat there silently, the angrier I began to feel. Mostly I was angry with myself. But I also was harboring resentment towards Krista. Krista, the analytical engineer, had probably been researching transitioning for months, had probably worked through all of her equations and now was ready to circle the answer. I could see myself getting jealous watching her grow and change, and myself getting more and more depressed because I wasn't. I loved my current life with Krista and was afraid of losing it. Sitting at our kitchen table, over some takeout food we picked up, Krista started the conversation I had feared, "So Penny, what did you think of the presentation?" And that was that. I broke down. In retrospect it was probably cathartic. Krista listened patiently. I think she knew this wasn't about her. It was all about me. I wore myself out crying and fell asleep on the couch. The next morning, as I got ready for work, I noticed that I still had nail polish on. I kept staring at my hands, unable to move. I looked at myself in the mirror and slowly started to smile. I felt an actual concrete decision forming in my brain. I finished getting ready, leaving the nail polish on. I gave Krista a quick kiss and left for work. I'm pretty sure she noticed my nails because I made a point of waving bye to her. Rather than going to my office, I headed straight to the HR department. It was still early, Caroline, the HR director, was the only one in, sitting in her office. I wasn't sure if she saw me, so I poked my head in, "Knock knock, are you busy?" I asked. "Oh, good morning Peter, come on in and have a seat. Sorry, I didn't see you standing there." "I need some advice Caroline," I started saying. I saw her take a glance at my colored nails. "Sure, what do you need?" she replied and started opening a desk drawer, looking for, then picking up a pamphlet of some sort. "Thanks. I know I haven't been here that long and I love working here, but I need ..." As I was about to answer her question, she was pushing the pamphlet across her desk. I looked down and saw the title on the cover, "Corporate Guide to Transitioning at Work". "Some career advice," I finished saying. "Oops," she said, trying to pull back the pamphlet, hoping I hadn't seen the title. "No, that's ok," I said, reaching for the pamphlet, "I might need that too, but that's not why I'm here today. So I explained that I had seen the company job posting for a "community liaison officer". I told her how I became a lawyer and that legal work was not really something I had a passion for. But I explained how having a law degree would be a real asset for this liaison position and how I envisioned the job, adding responsibilities beyond those listed in the description." "So the advice I need is whether or not this is something I should apply for." Caroline leaned back and smiled. "As far as I'm concerned, you just did. I'll run this by Rebecca and set up an interview. By the way, she was really impressed by your volunteer work for the LGBTQ event." I felt a wave of confidence wash over me. I wondered if the nail polish was some sort of trigger. Maybe I should say something about that before I leave. "About the nail polish," I started to explain to Caroline. "Read page three in the guide. You're fine. Nice shade of red by the way." Over the next several weeks, I started to chip away at the "Peter costume". I found a therapist (page 12 in the pamphlet) and began meeting regularly with her. Which worked out great because Krista's therapist was in the same medical arts building. We're usually able to schedule our sessions at the same time. I did get the liaison officer job, and I'm really good at it. Because I give presentations to groups ranging from small charities to corporate boards, the company gave me a clothing allowance. I've become a valued customer at the boutique where my first dress came from. I'm discovering how a well tailored dress and killer heels can intimidate a boardroom full of men. Krista and I are well on our way to becoming who we were always meant be. It's going to be a life long adventure. We're excited to begin the journey. Authors Note: I want to thank all of you who have read my collection of stories. Your support means a lot. In school, I did not like nor excel in either writing or art. My strengths were in math and science, later getting degrees in physics and mathematics and working in machine learning research. Yet, writing and art (I paint oil portraits of women), have become my passions. So, don't give up learning. You never know what you'll discover you really enjoy and are good at.