In For A Penny free porn video

It started innocently enough. My wife, Susan, had been out of town for four days of a two-week work-related training session and I was, shall we say, frustrated and missing our sex life. I was trying to masturbate while fantasizing about her but I kept losing my erection. On her side of the bed, hanging on the post, was the blue nightgown she wore the last night she was home. I could still remember how that felt as I rubbed up against her so I reached over and grabbed it. A faint trace of her perfume remained on the nightgown and I inhaled it deeply. I began to rub the nightie on my body and my stirring cock. To this day I don't know why but I slipped it over my head and stood up, letting the silky fabric slowly fall down my body, stopping just above my knees. The softness, the smoothness of the fabric felt wonderful and freeing. In minutes I was back on the bed rubbing my cock through the nightie. Before I knew it I had come hard and was drifting to sleep. When morning came, I went downstairs for my sunrise ritual of coffee and the newspaper. It wasn't until I was on the lawn retrieving the paper when I realized I was still wearing Susan's nightie. The morning breeze flowing under the nightie, around my legs and privates was invigorating. I hurried back inside before anyone saw and went to the kitchen. I was embarassed, aroused, and extremely comfortable in this nightgown. The cut, the feel, everything about it, down to the color, felt good. I made coffee and had a seat in the breakfast nook, crossing my legs as I had seen Susan do so many times. After coffee, I went upstairs, masturbated again and then got ready for work. I spent most of the day mildly aroused over the events of the previous night, enough so that when I got home and took off my suit, I put on the nightgown again. The feeling and the exhileration was the same as the night before. Today, however, I looked in the mirror and saw myself. While I had never been a muscular man, only standing 5' 7" and weighing around 140 lbs, I would never have thought of myself as girly. However, standing there in that nightgown, I began to see something feminine about my reflection. Immediately my cock made itself known, rising up against the silkiness of the nightgown. I went over to my wife's side table and took her vibrator from the drawer. Turned up all the way, I began rubbing the hard plastic against my throbbing cock. The vibrations felt nice but not strong enough. I pulled a back/neck massage wand out of the closet and plugged it in. Gently touching it to my cock was almost enough to make me come without any effort. So I climbed on the bed and began to run the massager over my engorged penis. Before long I had one hand pinching one of my nipples and the other holding the massager directly on my foreskin. My mind was flooded with all sorts of images; from my wife and I having sex to being under a well muscled man and feeling his cock deep inside me. That final fantasy took me over the top and I found myself spurting come up my chest and on my face. I began to come even harder and squirt even farther. Instinctively (?) I stuck my tongue out and caught some of my own semen, swallowing what I could catch. I scooped some off the nightgown and licked my fingers. At that moment, I realized something inside me had changed. After a short rest, I took off my damp nightie and put it in the washer. Passing the mirror I noticed semen in my hair! I climbed in the shower and decided to use my wife's shampoo, conditioner and perfumed shower gel. The smell was intoxicating. "In for a penny, in for a pound," I thought to myself and reached for the Nair. After a smelly fifteen minutes I was hairless, not that I had much to begin with, and smelling wonderful. A very close shave of my face made things even better. With the blue nightgown soiled, I went to Susan's drawers and pulled out a silky pink nightie that almost touched the floor. Feeling it slide over my newly hairless body was arousing, yes, but comforting as well. I stepped in front of the full length mirror to admire myself. I twirled around and watched the nightie flare at the bottom, exposing my rather female-looking legs. I repeated this two or three times and became embarassed with the thoughts now running through my head. How would these legs look in heels? How about a short skirt? After a short debate I opened Susan's closet and chose a short black skirt, ivory blouse, and a pair of 3" heels. From her lingerie drawer I took a lacy bra and matching panties. I laid all the items out on the bed and stepped back. What was I doing? Had I gone insane? I decided I needed to walk away from this for a few moments and clear my head. Without realizing what I was doing, I stepped in Susan's slippers, pulled on her chenille robe and went downstairs. In the kitchen I noticed my hands were visably shaking and that I could hear my heart pounding in my ears. I needed to relax and, most likely eat something. After fixing myself a plate of grapes, apples, kiwi and cheese, I noticed a bottle of chardonnay and poured myself a glass. Soon I was curled up on the couch, watching television and beginning my third glass of wine. Now, I am not one to drink more than a glass of wine and even that would be rare. I prefer dark beer or a good scotch over anything else but tonight the wine seemed appropriate. Apparently three glasses of chardonnay not only calm you down but bolster your confidence. I switched off the television and went upstairs. "In for a penny, in for a pound," I declared as I plugged in the curling iron. I had no experience at any of this but, for some strange reason, decided to give this a go. My hair wasn't exactly long, but it was past my ears in a rather shaggy cut and it took the curl well. Minutes later I had random tight curls all over my head. I sat at Susan's vanity and decided to try my hand at a little makeup. As a graphic designer and struggling painter, I have some freehand art skills and figured the application of cosmetics would be a breeze. I focused on one section at a time in order not to get too freaked out. Humbled, I finally had an acceptable finished product some 45 minutes later. Nervously I began to dress, stuffing the bra with pairs of pantyhose from Susan's drawer. The first few steps were a challenge but I quickly adapted to walking in heels. Returning to the vanity, I lightly brushed out the curls and headed for the mirror. My knees buckled and I came close to passing out when I saw my reflection. Gone was the man I had been for nearly thirty years! In his place was a woman with the potential to be rather attractive. A woman who looked enough like the man I was, to be related, but not enough to be him! With trembling hands I touched my face, tracing the now noticably feminine contours I, and everyone, had apparently overlooked for years. Having had pierced ears since my teens, I removed my silver studs and replaced them with dangling silver and amethyst earrings from Susan's jewelry box. I slipped on a bracelet, a necklace and a couple simple rings. I admired myself again and was pleased with what I saw - a woman. Noticing it was almost eleven, I succumbed to another impulse. The headiness of the wine long gone, I tossed my keys, twenty dollars and identification in one of Susan's spare purses and made for the garage. My neighbors would all be asleep or certainly confined to their homes by now. The risk of being seen was minimal and only crossed my mind for a moment before fleeing for good. Soon I was in my Triumph Spitfire, driving around town. At one stoplight, near the art district, I happened to catch the eye of a young man in a new Jaguar. His smile told me he liked what he saw. I blushed and demurely smiled back. I was flirting with a man! Okay, maybe not all the wine had worn off by now! I gave his expensive auto a once over and nodded my approval. He mouthed the words "Thank you" and "Bye" as the light turned green and he pulled away. I started to do the same when my car lurched forward and stalled in the intersection. Thankfully there was not a lot of traffic and I was not a hazard to oncoming traffic. I tried starting my car but it apparently had a mind of its own. Here I was downtown, miles from home, and totally unprepared for anything like this. Then to top it off, as if I had somehow forgotten, the thought raced through my head that I wasn't a woman despite outward appearances! I began to panic. What was I going to do? What was I going to say if the police came? My panic attack was interrupted by a rapping on my window. There stood the man from the Jaguar! Quickly I turned away from him and practiced a female voice. I had no idea if it was passible or a giveaway but I had no choice. I rolled down the window and blushed. He was direct and to the point. "Stalled?" "Worse, I think," I replied. "These things can do that," he said. "Put it in neutral and I'll push. Park on the street over there." I got out of my car and locked the door. "Can I give you a ride somewhere?" The question scared me more than I can relate. I had no cell phone to call a tow truck and even if I did, I had nothing more than $20 on hand. I had no choice but to accept and at least get a ride closer to home and walk the last bit. "That would be great," I responded. "But I live over in Bayberry Hills. I can get a cab." "Nonsense," he countered. "What kind of gentleman leaves a lovely lady alone at midnight? Come with me." With that, he stuck out his arm and waited for me to take it. I did, hestiantly, and he ushered me to his car. Like a true gentleman, he held the door and helped me in. It turned out he also was rather chatty. "We've never been introduced. I'm Paul and it is my pleasure to see you home." "Thank you Paul, " I blushed. Since the phrase helped get me in this mess, I stole from it and said, "I'm.. Penny and it is my pleasure to have you escort me." "Penny is an uncommon name these days. I, for one, like it." My fear of talking set in. What must he think? What would he think if he found out I wasn't a woman? So I decided to set him talking. "So tell me about Paul. What do you do, what do you like?" "Well, I am a real estate agent by day and a starving artist at night. In fact, I just left a show where I had one piece entered." "Wow! An artist..." I left the door open. If Paul was like most artists I knew, he could go on about himself for the entire drive. "A struggling artist," he countered. "I think I'm half decent but I suppose it is a matter of opinion and perspective. And what is your opinion on art and artists, Penny?" "It varies. I think I prefer the old masters when it comes to paintings. However, I am fond of one sculptor from Chicago who works in limestone and marble primarily." "Walter Arnold? I love his stuff! Have you seen the Telemones in the House of Blues hotel?" "Yes! It's so simple and gorgeous! His gargoyles are impressive as well." Well, so much for trying to keep quiet during the drive home! We talked about various artists from Claude Monet to Sir Anthony Caro. Our chatter continued for close to thirty minutes in my driveway. Paul came around and opened my door. "Thank you for bringing me home Paul. I really enjoyed our chat." "As did I! It is refreshing being able to talk to someone who knows art and artists. In fact, tomorrow night is a small showing at Landstone from 7:00 to 9:00. Would you care to go?" "Landstone? Tomorrow? Do you mean the Braswell collection? That showing is by invitation only!" "I've done a bit of commission work for Charlotte Braswell so I always get in the good shows! So shall I pick you up at say 5:00 and grab dinner first? In fact I will even introduce you to Mrs. Braswell." "Wow. How about 6:30 and we have dinner later?" "It's a date!" Paul leaned in for a hug and I willingly complied. The Braswell collection! In my excitement, I gave Paul a small kiss on the cheek and went inside. I was going to the premiere showing in the state! I was going to see the Braswell collection! I had a date with a man. What had I done? After a moment or two to catch my breath, I ran back outside to stop Paul and this whole nonsensical thing, but he was gone. I was committed to a date as a woman. Part of me was scared and another part of me was exhilerated. I locked the door, went upstairs, washed up, changed back into the pink nightgown and went to bed. It was almost 10:30 when I woke up feeling a bit disoriented. Coming back to reality from my dream was quite the shock and disappointment, especially when I saw the tenting of my top sheet. I had spent a wild dream night dancing and dining with Paul, whose dreamworld kiss was still tingling my lips. I grabbed the massage wand again and placed it against my erection. Within moments, a small fountain of sperm erupted onto my stomach and chest. Another nightgown soiled. I got up, washed my face and threw on a sweatshirt and jeans. The curls in my hair betrayed my masculinity, as did the earrings I apparently slept in. On went my ratty old baseball cap and out came the earrings. Earring, actually, as one apparently had fallen out during the night. I'm not exactly sure why but these, my normal clothes, felt unbelievably foreign to me. Nonetheless, I had a car to rescue and a date for which to prepare! Getting in my daily driver, a well used but still good looking Lexus SC- 400, I went to rescue my Triumph. Luckily it only took a few moments to get it running again. I called my sister, Lisa, to see if she was available to drive it back home for me. Again, as luck would have it, she was free. Arriving back at my house, Lisa questioned me, "I thought Susan doesn't know how to drive a stick?" "She doesn't." "Well, how did she leave this on the driver's seat?" In my hand she placed the missing earring. Immediately I felt my face flush. "Care to tell me what is going on little brother?" "Nothing! Susan apparently lost it the last time we were out." I felt I covered that just fine. "Oh. And I suppose the last time you were out you just happened to curl your hair and get perfume on you? What gives?" I took Lisa inside and spilled my guts, telling her everything from my innocent beginning through the ride home. "And you have a date with him in about what, 6 hours? Are you serious?" I hung my head, ashamedly, and nodded. "Well little -sister-, lets get in gear! What are you going to wear? What are you doing for cleavage? How can I help?" I smiled. "You really want to help me? I mean, this is all so.. " "Fucked up? Yeah it is, but you are in a situation and don't I always come through? Besides, I am DYING to see what you look like as a girl." Lisa began to chuckle, "Apparently good enough based on last night!" "Ok," I said excitedly. "Let's go see what Susan has that we can borrow." Lisa stopped me as I stood up. "Wait a minute, -sis-," she said emphasizing the familial noun. "You're a blonde, Susan is a brunette. You have blue eyes, Susan has brown. Not to mention you aren't exactly the same size. It's all wrong! We need to go shopping. Now don't look at me with that weird face. We'll measure you here and go buy our 'sister' a birthday present or two. Then we can come back here and make sure it fits right." I had to ponder that for a moment before agreeing it would work. Lisa dialed the phone. "Markie? I know! Maybe this week. Anyway, I need a set of forms pronto. No, I haven't sprung a leak, dork. They're for a friend. Fitting? Sure, we'll be right there." I grimaced. "Do I even want to know what that was all about?" "Markie is a friend of mine who manages a medical prosthetics store." "I have all my arms and legs, Lisa." "But you don't have boobs, babe. You will though, you will!" Lisa just laughed and grabbed her purse. "Lets go!" We pulled into the parking lot of one of the many look-alike medical buildings near the hospital and entered the prosthetics shop. The clerk, a a very fashionable, slender man in his late 20s who was all business, was adjusting someone's new arm. We patiently waited for them to leave. The man's demeanor totally changed when we were all alone. "Lisa! Honey! Come here," he flamed. Gone was the stoic concerned businessman of a few moments ago. "And who is this?" "Markie, this is my brother Alan, who tonight has to be my sister Penny." Markie waved me over. "Let me look at you girl!" He walked around me and to the back of the store, snapping his fingers and calling as he went. "Privacy! Back here, ladies!" We followed him past some private fitting rooms and to the store office. "What's the occasion, " Markie asked. "Contest? Trannygirl? Closet dresser?" Markie's eyebrows wiggled in a suggestive way, revealing many other options that were left unspoken. "I got myself into a jam and have a date tonight." I figured short and simple was all that was needed. "Honey, " Markie countered. "People don't get in jams like that unless they want it." I must have turned a thousand shades of red because Lisa slapped me on the shoulder and gasped audibly. "You actually LIKE this guy, don't you?" "No! Well, a bit. I mean, we have a lot in common." I decided to explain the situation for Markie's sake. "He's in the art community and I am a struggling beginner. He's taking me to see the Braswell collection tonight. And then dinner afterwards." I realized how much I was smiling. "Ohh, the Braswell collection!" Markie sounded appropriately impressed. "I have absolutely no idea what that is but it sounds as if you can't wait for it and for him! Anyway, lets start." I blushed again and took off my shirt for the fitting. Thankfully, we left the adhering to when we get home. A few minutes with measuring and various websites told us that I was essentially a size 6. That is, if I wore a padded girdle to tighten my stomach an inch or two and add a few inches to my hips and ass. Markie suggested that the best place to get the girdle was a small lingerie shop across town and the most forgiving dresses, although not sure what he meant by that, would be had at J.C. Penney. So, off we went to the lingerie shop, which turned out to be a breeze. Markie had called Sharon, the owner, ahead of time and spilled all the beans and measurements as well. When we got there, Sharon had the "perfect" girdle picked out as well as a couple different bras for me to try on. Embarassed as hell, I went with her and was fitted properly with two 32C bras, one black and one white. At Penneys we looked around and decided on two drastically different dresses. One, a black satin sleeveless drapeneck and the other, a black bolero jacket dress. I was leaning toward the latter as it covered more back and had a slightly higher neckline. Although at this cut it should be called a slightly higher breast line! The jacket, I felt was more appropriate since the weather was starting to cool more at night. On the way home Lisa asked me about my "Penny voice" and I gladly showed her. She was impressed. It was then I got a quick lecture in the differences in speech patterns. Men 'want', women 'would like'. Men 'get', women 'will have'. By the time I dropped Lisa at her house to get her car and returned home, it was nearly 3pm. Lisa said she would be there by 4 and for me to start showering and shaving whatever stubble arose overnight. My excitement for the evening had been building all day and it was beginning to manifest itself in the form of a growing erection. I lay down on my bed, draped a towel over myself and began using the massage wand once again. This time, however, my fantasies took me down the path of most women; I was making love to my man. In no time at all I was having one of my strongest orgasms to date. I showered and had just gotten in one of Susan's robes when Lisa returned carrying a few bags. It was just after 4:30. "Look at you! The blue robe works on you! Come here." Lisa waved me over to the vanity. "I took the liberty of picking out some makeup for you. You can't use Susan's old stuff for something as nice as tonight. Besides, I have the feeling this is not going to be the last time you do this, right?" I really hadn't given that any thought. Would I keep playing around in Susans clothes? Would I buy more of my own? The answer to that last question was a definite maybe. "Regardless, " she continued. "Sit down and let me decide what we are doing about your hair." Lisa was a hairstylist. She abhorred the terms barber or hairdresser. She started cosmetology school with the intent on eventually moving to Hollywood as a make-up artist. Then, after working with some people who she called "beyond all hope" she decided to focus on hair and not have to use a trowel to try to make some women look human. Before she started with the makeup she shaped my brows and, admittedly, went too far with them. Then, she painstakingly used a creme foundation and white powder on my beard line. While I didn't have much of a beard and it was blonde, she told me that there is a difference in pore size or something. I just nodded and let her continue on. She told me how this was a formal affair that bright colors are definitely out. I believe she used the term Smokey Taupe. But all I know is it was brownish with a bit of a blue/purple undertone that made the blue in my eyes jump out. Or so she said! A similar subdued palette went on the lips and cheeks too. I was not allowed to see her progress. Then she had me get dressed. She started with a pair of pantyhose and then had me add the girdle. Never having worn a girdle, it was a definite surprise. Tight, almost uncomfortable in some ways yet at the same time one could say it was comforting and secure. Having false breasts adhered to one's chest is certainly a different feeling. I couldn't help but bounce up and down and watch. Sadly I found myself wishing I could feel the weight and pull of them. Next was the bra and a then a slip Lisa had picked up on her way. I never really understood how many different layers could go into a woman's outfit! After a quick lesson on proper sitting and standing, entering and exiting a car and the like, Lisa started cleaning my fingernails with something that smelled a lot like alcohol. She explained that it was to remove the excess oils so the false nails would adhere better. At this point I began to freak out a bit. "I can't do that! I have to go to work in two days!" "Relax, " she assured me. "These just glue on and can be taken off at any time." "In for a penny, in for a pound," I muttered. "So that's where you got your name! Makes sense since you always say it!" Calming down, I let her fit and glue nails to my fingers. They weren't exceedingly long, thankfully, lest I poke my eye out! Then she coated them with layer after layer of polish that looked very similar to the lipcolor she used on me. I had to admit that I liked how they looked and how they made my hands look. Soft, dainty, feminine. Then she did my toes. While the nails dried Lisa started on my hair. A few snips here, some mousse or gel or something and a lot of flat iron work later, she was finished and definitely pleased with her work. "This is my present to you, my little sister Penny." Reaching in the bag she pulled out a small jewelry box that contained a single natural pearl on a gold chain and fastened it around my neck. Matching that were simply elegant earrings, a pearl post with two gold chains. Each chain had a pearl at the end. Finally, a gold chain bracelet with a few pearls on it. "Lisa, " I gasped. "You shouldn't have done this. Please take them back. Um.. tomorrow!" I laughed. "No honey, listen. Something has changed here. The brother I grew up with would never have done something like this, even for the prestigious Braswell collection. They show that every couple years and you have never done anything out of the ordinary to get in. So, despite what you think you believe, that is not your reason for this. And besides, that wasn't even in play when you went for a drive last night. No, something definitely has changed and I believe I am beginning to actually gain a sister, at least a part-time sister, anyway." She began to tear up. "Regardless of what happens, know that I will always be here for you and will hold your hand until you can walk alone." We hugged briefly before she noticed it was almost 6:00 and we only had 30 more minutes to go. Lisa pulled out a pair of her own shoes, which happened to be the same size I wear, and had me step in them. The heels were only about 2 1/2 inches tall, lower than the pair of Susan's I lumbered in last night. These were open-toed with a sling back that made my ankles look almost edible. Finally she guided me to the full length mirror. My knees buckled and Lisa had to help steady me. The woman I saw in the mirror last night was nothing compared to how I looked now. I was gorgeous. I turned and twirled and posed like a school girl. "You're beautiful, Penny! Let me take your picture to show Les." Leslie was Lisa's partner of 15 years. "I told her I was helping you with something and I would be home by 7:00." A few snapshots later it was almost 6:15. Lisa filled my clutch purse with what I would need for touch-ups and repairs and were starting downstairs when the doorbell rang. My knees buckled again at the thought of Paul being here. Lisa looked through the peep-hole and then swung the door open. It was Leslie. "Hey babe, I came by to see if I could help with whatever you were doing for Alan." Then Leslie saw me standing there, purse in hand. "And who's the chicky?" "Oh, " Lisa said. "Penny, please meet my partner Leslie." Leslie extended her hand forcefully. It was obvious she felt threatened in some way. "And Les, honey, meet Penny. My sister." She took my hand and gently shook it before things started to register. "Lisa, you don't have a sis..ter..." Leslie's eyes grew extremely wide and her jaw nearly hit the floor. She turned to face Lisa. "No fucking way. It can't be." In my softest, most feminine voice I replied. "What a pleasure it is to meet you Leslie. Lisa had told me so much about you." I added a giggle for effect. Leslie just shook her head and continued to eye me. "Wow, girl, you're quite the hot little femme aren't ya? Is Alan gone for good?" Lisa interrupted by telling Leslie that she had a few more things to coach me on before my date arrived. "Date? Penny has a date? With a man?" Lisa starting pushing Leslie towards the living room. "Okay. Okay. I'll leave you girly girls alone." As Lisa was instructing me on certain mannerisms, how not to give myself away, and basic flirting techniques, the doorbell rang again. When I opened the door, I expected to see Paul in a nice suit but a tuxedo was nowhere in my mind. However what quickly was in my mind was how absolutely handsome he was in that tux. For the first time I noticed his build and especially his eyes. Deep deep blue eyes that looked even more attractive with his sandy brown hair. This was a man I would be proud to be seen with! "Penny! You look amazing, " said Paul. "You'll be the best looking woman at this function by far." With that, he handed me a single red rose. "I was going to bring you a corsage, since this is a formal event but I had no idea what you would be wearing. I hope this is ok." >From behind me I heard Lisa call. "Penny, you almost forgot this!" She handed me a small box with a flower for Paul's lapel. I introduced the two of them and thanked Lisa, who nodded her approval of my date. Closing the door behind her, I turned, pinned the flower to Paul's lapel and kissed him gently on the cheek. As the Jaguar pulled away, I noticed Lisa and Les looking through the living room window with smiles rivaling the Cheshire Cat. On the drive to the Landstone, Paul commented a few times on how pretty I was. I was simply in heaven! Since he wasn't spending time shifting, he held my hand the entire drive. I must say I thoroughly enjoyed it. Paul explained who would be at the showing tonight; it was essentially a local Who's Who. I was extremely nervous about my first contact with the local "in-crowd" of the art world. Paul assured me that no one would be questioning whether I belonged there. The valet at the Landstone opened my door and I remembered to gently swing my legs out before standing. I understood at that moment the power of a woman's body. The valet was staring at my legs. "Problem?" I asked. "No, ma'am. I apologize. I was just admiring your beauty." The young man helped me out and noticably blushed. Paul took my arm and escorted me into the most prestigious gallery in the state and one of the most amazing art collections ever assembled. As the first couple approached us, Paul quickly whispered to me. "Before they get here, what is your last name again?" "Allen," I responded, kicking myself for a lack of imagination. A few times early on I was introduced as his date for the evening and later as his girlfriend. The latter began when an elderly woman asked Paul if I was his new girlfriend and if he was going to manage to hang on to me for a change. Paul's response caught me off-guard. "I do hope so, Grandmother. I've never encountered such a beautiful woman, both on the inside and outside." Talk about your smooth lines! We continued on, looking at paintings from Rembrandt to Piccaso, from Monet to Max. We seemed to like and dislike similar pieces and later found ourselves engaged in quite the debate over Van Gogh's religious beliefs. (Paul believes he remained a devout Christian and I feel he renounced the Church in the late 1800s) I met everyone possible from local critics and artists to the Governor himself. As the showing wore down, I noticed Paul hadn't introduced me to Charlotte Braswell. In fact, it seemed he avoided her. I pulled on his arm and brought him close to me. Whispering, I asked, "Are you going to introduce me to Mrs. Braswell?" Paul was hesitant to respond and looked a bit dejected. "I was saving that for last. Actually, I was hoping you forgot. But lets go." Was Paul ashamed of me? Did he know? Was my makeup ok? I was deep in wondering why Paul didn't want to introduce me to the hostess of this soiree when she approached us. "Paulie, who is this lovely woman I have seen you with all night?" She reached for my hand quickly. "I am Charlotte Braswell and thank you for coming to our little party. You are?" "Penny Allen, Mrs, Braswell. I am honored to be here and in the presence of such amazing art and wonderful people." We gently shook hands. Turning to my obviously uncomfortable date she continued. "Paulie, where have you been hiding Miss Allen? I have been watching you two all night and I must say you make a wonderful couple. But of course I am biased!" Paul seemed to puff up a bit. "Penny and I met last evening, actually. We had so much in common I simply had to invite her here and get to know her better." "Lovely, " Mrs. Braswell replied. "An art lover, are you Penny? Well then... Who is your favorite painter?" I chuckled. I was being tested for some reason. "Well, as I told Paul, I prefer the old masters. Renaissance, Pre-Raphaelites, Impressionism. I even like some Modernism - probably up to Chagall, if I had to define a timeline." "Oh, I see, " she responded. "Did you see our Picassos? You should love them." I grinned. She was trying to trip me up! "I did see them, but as I said my Modernism stops with Chagall. Cubism, while it may have influenced Marc, was not his style. As for Cubists, I simply have never cared for their style or appreciated their work. A surrealist like Dali at least showed you what was in his mind. Picasso and Braque, for example, wanted you to guess. To me, it was as if they were trying to play a game of chess with their audience." Mrs. Braswell grabbed onto my arm and squeezed. "You definitely do know your art, dear. Paulie, don't mess this one up, she's a keeper!" We began to walk away when I turned and asked Paul, "Well, did I pass her test?" "Apparently so, I've never seen her give such approval to any of my dates before! And I must admit she is right, so far." Paul and I were headed for the door when Mrs. Braswell caught up and pulled Paul aside. "Don't forget tomorrow night, Paulie." "I won't, I will at least make an appearance." "It's Grandmama's 80th birthday celebration, you need to make more than an appearance, young man. If you'd like, you may bring Penny." "Ok, I'll be there." The two exchanged hugs and air kisses. Paul returned to me and we headed for the car. As we pulled away Paul broke the silence with a sigh. "I suppose you heard? Care to join me tomorrow night?" Paul seemed genuinely dejected and almost afraid to look me in the eye. "Sure, " I answered, smiling. "I'd love to.." My reponse trailed off a bit as I started to connect all the available dots. Perhaps it was the champagne slowing me down but it wasn't until that moment that I realized that Paul was a Braswell. After a moment of silence, I had to ask. "Why didn't you tell me you were a Braswell?" "I wanted you to like me for who I am and not for who my folks are. And definitely not for the money." "So, is that why you avoided introducing me to your mother? You were afraid I would find out you were a Braswell?" Paul turned red and nodded. "Yeah, kind of stupid wasn't it?" I don't know why but I leaned over and kissed him on the cheek then briefly rested my head on his shoulder. "No, it wasn't stupid. I understand." For some reason it was one of the sweetest things I had seen in a long time. A few quiet moments later he pulled into the fanciest restaurant in town, El Mejor. Yes, it was Mexican food, but trust me, this wasn't anything like Taco Bell! I had a wonderful entree of Chipotle and Lime Grilled Shrimp and one very strong strawberry margarita! Paul had relaxed quite a bit (read 2 frozen margaritas) and proceeded to tell me about the general dysfunction money can bring to a family. After dinner we walked along the lake at Myrranis Park and talked about art, family and friends. I learned quite a bit about the Braswell family, their collection, how they came into their money (19th century railroading) and, of course, the dreaded Sunday birthday party. We finally decided to call it an evening around 10:00. On the way home, Paul never was out of contact, holding my hand almost the entire drive. After assisting me from the car, Paul walked me to the door and we both looked at each other for a while. We fell over one another, verbally, with equally clumsy words of appreciation and smiles for a wonderful time had. Suddenly Paul moved closer. "Oh the hell with it, " he muttered. With that, he kissed me. Not lightly, not gently. The kiss was forceful, yet rushed; almost clumsy. With alarm, he retreated a few steps waiting for my reaction. I was scared, out of my element, and completely infatuated with my suitor. Putting my arms up, around his neck, I kissed him back. Our lips parted and our tongues met. A slippery dance of exploration began, bringing shortness to our breath. Paul came in closer and closer, kissing with more and more force until my back was against the door. Stopping for air, albeit briefly, I knew I wanted this to continue and pulled him to me. I was lost in the throes of passion until I felt him up against me, an unmistakeable hardness on a wall of flesh. I broke off our kiss. "I really did have a wonderful time tonight Paul and look forward to tomorrow." "So did I, " he panted. "About that, how about I pick you up around 6:30 again. The party is at 7:00 and hopefully we can get out by 8:00." Plans made, we kissed one more time before I entered the house and locked the door behind me. I was more turned on than I had ever been in the three years I had been with Susan. I was possibly more turned on than I had ever been in my life! I locked the door, heading upstairs with personal relief on my mind when I spotted a note on my bed from Lisa. It simply instructed me to call her immediately and open my present, which I did. Before I could object, Lisa was on her way over. I washed up and put on my new blue nightgown that Lisa had left for me. The tag said "Satin Chemise" but it looked a lot like what I would have called a baby doll. There was also a matching satin robe in the box and, for propriety, I put that on as well. And went downstairs to put on a pot of decaf. Lisa arrived moments later calling to me from the front door. "Penny! Up or down?" "Down, " I yelled back, "Kitchen!" She was as eager as a teenager to know every detail of the date and hung on every word. She was particularly impressed with the walk along the lake. "Sounds like he might have tried to get romantic there, " she added. I told him he was a total gentleman and continued the story about the drive home and the hand holding. I decided to stop right there and wait for her reactions. "That's it? Did he try to kiss you or anything?" I remained silent. "He did, didn't he? What did you do, run inside? Did you slap him? Were you scared?" So I told her exactly how it played out. The look on her face was one of total shock. "You basically made out with him on the porch? But you're a married woman. I mean, man. Shit! This is confusing, Alan.. or Penny.. or whatever!" "You think it is confusing for YOU, Lis? I'm the one dating a man and pretending to be a woman!" "Well, going out once isn't exactly dating." "Yeah, um.. about that. We're going to his grandmother's birthday party tomorrow too." I hung my head in somewhat mock shame. "ALAN!" There was genuine concern and confusion in Lisa's face. "You realize that this isn't a game for him, don't you? Someone is bound to get hurt." "I do understand. And please, Lisa, don't call me that right now." "But you aren't Penny. You're my brother ALAN no matter how you still sound." Apparently I was still using my Penny voice. "I was having fun with this earlier when I thought it was just getting you out of a jam tonight and having you pretend and dress up and stuff. It was like.. I don't know... having a little sister for a moment." I reached across the table and placed my hand on hers. "Lisa? I think Penny IS me. I can't even begin to describe this to you. I feel, well, liberated! Comfortable! I feel like a totally new person. I actually like how I look and how I feel with Paul. And I actually really like Paul, a lot!" Lisa's other hand joined the mix. "You mean, you think this may be something you continue? What about Susan? Isn't this fast?" All hands were joined now. "I just don't know, sis. I am very confused." I began to cry a little. "Three days ago I had never even given thought to wearing a dress or anything. Now, I can't wait to go shopping tomorrow and I can't wait to see Paul. I don't know what is happening or where this is all going. What I do know is I have to explore this and see whats going on inside and when Susan returns, see how I feel about her, us, me, and everything." We stood and hugged and chatted for a little more. Lisa left but agreed to meet me at noon to find a less formal outfit for Sunday evening. I locked up the house and went to bed, hoping to put this very emotional day behind me and get some rest. Unfortunately my dreams were pretty wild. They ranged from quietly cuddling with Paul to Susan kicking Penny out of the house. I even had a dream where everyone at work kept laughing at me because they could tell I was wearing a bra under my shirt and tie. By 5:00 I was done with attempting to sleep so I decided to go for a run. I hadn't been running in a few days and I needed that solitude, that rush and the time to think about things. I threw on my jogging shorts, gym t- shirt and my running shoes. In the mirror I saw, even without the makeup, a woman in clothes that hung wrong and looked slightly too big for her. My hair was still feminine looking, my legs and arms were smooth and my nails were painted. Nothing balanced! I dug out some of Susan's more casual stuff and tried those on. While they weren't exactly the right size, they just seemed to fit better. So, off I went to a nearby park for a jog. I had been jogging for about 15 minutes when I noticed a man behind me, gradually closing the distance. I decided to stop at the next bench and pretend to tie my shoe while he passed. Luck being what it is, he stopped. He started walking toward me. "It's a little early for you to be jogging alone, wouldn't you say?" Immediately I started to panic. I nervously looked around for anyone else who I could run towards. However, he must have sensed my nervousness as he lifted his shirt to reveal a police badge on his waist. "Don't worry, I just wanted to make sure you realized how dangerous this is!" He stuck out his hand and introduced himself. "Detective Tom Jarvis," he announced with pride. I gently shook his hand. "Penny Allen. And I do understand, officer. I normally have pepper spray with me." I was winging it. "That's good, Penny. How about I run with you for awhile, the sun will be up soon." I agreed and off we went. Detective Jarvis, or Tom as I was instructed to call him, chatted while we ran. Thankfully he wasn't annoying and made for pleasant company. He told me about his divorce, five years ago and asked about me. I explained to him I was considering moving here and was staying with my sister until I had decided. The sun came up and the run finished, we were about to part ways when Tom came back over to me. "Say, Penny. If you are going to be around at all this week, I would love to take you to dinner. Can I call you?" "Sure Tom, " I responded. I'm not sure of my schedule right now but if I can work it out, I'd love to." I gave him Lisa's phone number and headed home. "A cop? Are you insane? You can't go out with a cop!" Lisa was almost screaming at me. She was still angry I had gone jogging as Penny but understood, what with the nails and all. I think it was the fact I was jogging before sunrise, alone. Okay, the whole Tom thing wasn't going over well either. "Calm down. I have no intention on going out with him. I did the nice thing and gave him my number, or in this case yours. I, sadly, " I mock- sighed for emphasis, "won't have time for poor old Tom." Then I began to giggle. As if a light went on above her head, the realization hit her. "You're catching on to how to play the game, aren't you?" "Of course, " I reassured her. "I was on the recieving end of that long enough to get an idea. But it still is very flattering to be asked. Especially as messy as I was!" I had since showered and dressed in some of Susan's casual clothes. I had even made an attempt at a subdued "daytime look" with my makeup. Lisa did my hair and we were off to find something for tonight. Lisa headed directly to the jeans, explaining to me how every woman should have at least 3 pair, "Unless you're a dyke. Then we have at least 3 pair for each day!" She apparently found herself to be very funny because we had to stop so she could catch her breath. At this point, I moved her away from the jeans to a more preppy styled casual. "This probably isn't just going to be some run-of-the-mill party, Lisa. I should look better than just jeans. Even these might be too casual but since nothing was specified, it will work." Lisa looked confused so I somewhat explained. "Charlotte will be there. It will be high-brow." "Charlotte? Braswell? Why on earth would she be at his grandmother's party?" "It's what a good daughter does, Lisa." If this had been a cartoon, I swear I would have heard the gears grinding and calliope music playing. When Lisa's face started to drain of color, I knew she had caught on. "Oh my God! He's loaded, " Lisa exclaimed. "Loaded, cute and he wants YOU!" She started to frown. "You better be very careful. They're a powerful family and I suspect they could cause you a lot of problems." I dismissed it all with a wave of my hand. "It's not like we're getting married or anything! It's a couple dates. That's all." After a basic repeat of yesterday's preparation session, only with me doing the preparation and Lisa instructing, Paul arrived on time as always. A quick check in the mirror of my khaki-colored twill pants and teal v-neck sweater told me I was ready to go. Paul was handsome as ever in a simple pair of Dockers and a button-down oxford. Off we went, hand- in-hand. The party itself was absolutely morbid. Paul's grandmother was surrounded by all her rich cronies; none of which were under 80 and most of which were incoherent at times. The food, however, was grand and we both enjoyed the filet mignon. After about an hour, Paul excused us and we left. Paul wanted me to see some of his work, so we headed to his studio. As we pulled up to this gorgeous house, I noticed the connected studio. It had to be 3000 square feet of just studio! The house, of course, dwarfed this modest building. Paul took me on a tour of both the sculpting side and the painting side, showing me some of his pieces in the process. He was very talented with his hands and for the first time wondered how that talent transferred outside the studio. When we finished the tour of the studio, we proceeded to the house where we were greeted by Marta, his housekeeper. "Good evening Mr. Braswell, the lounge is ready." "Thank you Marta, " he replied, handing her $100. "That will be all for tonight. I appreciate you coming in on Sunday for me. And stop calling me Mr. Braswell!" "Yes, Mr. Braswell. Goodnight sir, " she respectfully nodded her head to him and then to me. "Miss." The lounge was a good sized room, apparently where the movies were watched and books were read. It was less formal than a library and didn't feel like a den. The mood had been set, however. There were candles burning everywhere and wine being chilled. Paul meant this to be a romantic evening. I decided to comply but set limits. We started talking art and ended up on politics, literature and pop culture. The conversation was filled with stories from our past as we learned more and more about one another. By the time we were on our second bottle of wine, it was nearly midnight. Paul leaned over and kissed me. Like the night before the chemistry was obvious and potentially volatile. We continued kissing until Paul found my neck and nearly caused me to melt all over his leather sofa. Then he asked what I feared most. "I was thinking, since it is so late, maybe I could convince you to stay?" We kissed again and then I pulled away. "I can't, " I replied, looking for a good reason. "See, tomorrow I have to go to work and I really, um, wasn't prepar--" Paul interrupted. "Penny? I know." I obviously relaxed. "Good, I'm glad. Then maybe some other time, ok?" I leaned forward to kiss him again. "No, I mean I know. About you." I was scared and there was no place to run. "You mean, you know everything?" Paul leaned forward and kissed me again, with unrestrained passion. Then he looked directly into my eyes. "Everything, " he stressed. "And that doesn't matter. I don't care whats under there." He glanced towards my outfit. "I still want you, regardless." With that I pulled him on top of me and kissed him. I began unbuttoning his shirt and running my hands on his chest. I had never felt a man's chest or chest hair before and it was wonderful. He stopped our fondling and led me upstairs to the master bedroom. He handed me a silk robe and told me to undress while he "set the mood". When I emerged from the adjoining bathroom, I was dressed in my underwear, bra and the robe. Paul, on the other hand, wore nothing but a very passionate gaze. Once in front of him, I let the robe fall from my shoulders and drop to the floor. "You're beautiful, Penny." The lust shone in Paul's eyes. "But you don't need those," he said, referring to my undergarments. "I want you naked beside me." I stood still as Paul unhooked my bra, leaving just my breast forms in place. I then stepped out of my underwear and knelt before him. I'm not sure why but my thought was to pleasure Paul immediately. So I began by gently caressing his penis. It was already at full erection and begging for attention. I had never seen another penis so close, nor smelled its musk. Paul's dwarfed anything I had ever seen in the mirror. Our roles confirmed, I Immediately knew what was needed. I licked up his shaft and took the entire head in my mouth, swirling around it with my tongue. I watched as my hands, painted nails and all, cupped his balls. The moans from overhead told me I was doing things correctly. A loud gasp and shiver, as I took in his whole cock, signaled even more approval. I begain to pump him with my mouth while gently squeezing his balls. Slowly, Paul rocked in rythym, sliding his shaft over my lips. I stopped, stood up and led Paul to the bed, kissing him as we climbed in. I wanted to explore every aspect of this man's body. To me, it was gorgeous, erotic and simply amazing. I traced the contours of his chisled pecs with my fingernails and ran my hands over his perfect abs. I kissed each and every body part I could, thoroughly mesmerized by his beauty. I wanted this Adonis; this wonderful and talented man. I went down on him a few more times, thoroughly lubricating him before I turned around and offered myself. He was my Degas and I, his naked ballerina. The feeling of him entering me was a mixture of pain and pleasure. After the inital spasms, I relaxed and enjoyed the fullness of Paul's cock inside me. I had never entertained anything like this before and now, it was all I wanted. I was on all fours with my boyfriend behind me, making love to me with abandon. Every thrust moved me to a new level of excitement. The swelling of his cock filled me, stretched me, threatened to break me - and I loved it. I began to counter his thrusts, driving him deeper and deeper into me. His balls struck mine like a metronome, keeping our dance in time. As he neared climax, I did too; his movements increasing in speed and power, driving me wild. I was just on the verge of one of the most powerful orgasms ever when Paul came, howling my name into the night like a wolf. Hearing him pushed me over the edge and prompted a similar call. We both collapsed on the bed, spent, and drifted off. I awoke some time later to find I was cuddled up to him, my head on his chest, with his arm securely around me. I reached up and kissed him. He smiled. I went back to sleep knowing that my life would never be the same.