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Transitions by Desiree Pleasence Introduction It's hard to believe all that has happened in the past several years. I was a relatively happily married closet cross dresser. My wife, Sherri, was blissfully unaware of my "hobby", though I thought of it as more of a passion. It was a passion that had been with me all my life. Ever since I was a young child, I had admired the beauty of femininity. That admiration manifested itself both as a sexual attraction to glamorous women but also as a desire to appear as one or, in my heart, to live as one. I never believed that I was one, nor desired to become one via sexual reassignment surgery. I was actually quite fond of my male bits. The emergence of the Internet in my youth opened my eyes. I obviously wasn't the only one with such feelings. The dark corners of the net were brimming with men that liked to dress as women, even live as women. There weren't really any proper role models for someone like me, though. It seemed that most were either transsexuals, attracted to men only, or living lives of secret desperation, hiding their proclivities as something to be ashamed of. I fell into the last camp, I suppose. I both loved who I was, who I wanted to be, but was also afraid of being rejected by society. Unfortunately, I really didn't encounter anyone online like who I dreamt of being. A woman with a penis proudly living a successful life in mainstream society without fear of discovery, not relegated to the margins of society, having to earn a living in pornography, escorting, cosmetology or such. I certainly didn't look down on those who followed those paths, but it just wasn't me. Starting out, I wasn't sexually attracted to masculinity. I was attracted to other "special" girls but I wasn't gay. But I realized that the type of woman I aspired to be were definitely the type desired by men. And, over time, after watching so much pornography online, my mind opened itself to the concept of having sex with men. I ended up fantasizing about being the ultra-glamorous bimbo type of woman that delighted in sucking cocks, swallowing cum, being fucked anally. The girls in the films and photos certainly seemed to enjoy it! I had never revealed my true self to any friends or family members. I basically led the life society expected of me. I graduated from college with a business degree in real estate. After graduation I became a Realtor, primarily residential but also some commercial. The career served me well, I could work as much or as little as I desired. Being an independent contractor, I was my own boss. Since I set my own schedule and work load, I had plenty of time to indulge my secret passion. After practicing real estate for two years, I obtained my Broker's license, but never opened my own brokerage. It was at the office where I met Sherri, another Realtor. She was definitely in the spectrum of the type of woman I admired and emulated. Always beautifully dressed and made up, though definitely more conservatively than the looks I strived for. More conservative, but in the same ballpark. Eventually, we formed a business team, a quite effective one at that. After working together for a while, I risked destroying our team by confiding that I had feelings for her and asked her out on a proper date. The rest is history: we became the stereotypical husband and wife real estate team. If you happen to be in the Fort Lauderdale area, you surely saw our signs around town. You know the ones. "Terrence & Sherri D'Oliveira: Consider it Sold!" The photo on the sign showed us both leaning back onto either side of a "SOLD!" sign, our arms crossed across our chests, each of us with one leg bent back, propped up against the sign post. Why did I say "relatively happily" married, you ask? If you've read this far, you already know the answer. Sure, I hit the jackpot with Sherri. She's beautiful, always glamorously feminine, a wonderful partner in our thriving real estate practice and quite the lioness in bed. We have plenty of money in our checking, investment & retirement accounts. We have a lovely, if somewhat modest, home. To everyone else, it looked like I had it all. But I also had my secret passion and it was driving me a little crazy. I yearned to indulge and share my passion instead of just exploring it in private. Although I tried to suppress my urges early in the marriage, the urges won out, of course. I started dressing at home whenever Sherri was working with clients independently. That led to online profiles on the typical fetish sites, like FetLife, Tumblr & TrannyDate. I flirted shamelessly with other "girls" and even men. The repressed desires led to some pretty outrageous fantasies that I shared freely online. You know how it is. Talking about going fulltime, becoming a glamorous bimbo sex doll, masturbating, drilling my ass with my lifelike vibrator and eagerly licking up my own cum on an open webcam that anyone could view. But I never took the step of actually meeting with anyone, much less living out the sexual escapades of my fantasies. So how did I end up where I am now? Reclining on the front deck of a huge yacht. Indulgently smoking a 120mm cigarette. A frozen daiquiri in my other hand. My ample breasts and semi-erect cock straining against my two piece bikini. My long blonde tresses and dangly earrings falling behind my shoulders. Open toed slides with 4" heels dangling from the tips of my toes. Looking up, I see several tourists on the promenade deck of a giant cruise ship that was in port taking on passengers. Several were definitely checking me out as we headed out to the Atlantic Ocean. One particularly cheeky fellow even has his binoculars out pointing right at me. What a perv! Fortunately, I like oversexed perverts. Setting the daiquiri down, I untuck my penis and free it from the confines of the bikini bottom. As I take a drag from my cigarette, I stoke my queen-size clit a few time until a drop of nectar emerges. Exhaling a thin stream of smoke, I look right at the binoculars, leaving no doubt that I know I'm being watched as I scoop up the nectar with one of my manicured and polished fingernails, bring it to my mouth and suck it clean. Taking my finger out of my mouth, I blow an air kiss to the cheeky fellow as his jaw drops. He lowers the binoculars but is rubs his crotch with his free hand. Mission accomplished! He's probably going to be frustrated the entire cruise as I doubt there's such a sexy babe with endowments like mine of the ship! Great. Now I'm totally horny. I guess I'll go in to the upper cabin and see who wants to give me some relief. There certainly won't be any shortage of willing volunteers among my coterie of sexy girls that I inspired and helped create. In the meantime, why don't you read about how it all began? Chapter One - Barbie's Birthday "Terry, can you come here a moment? I have a little problem" my wife Sherri called out in a sing-song tone of voice. I had just stepped out of the shower and toweled myself dry. I smiled knowingly hearing Sherri calling me with the diminutive form of my name. She generally only called me Terry when she was feeling frisky or mischievous. I stepped into the bedroom to gaze at Sherri sitting at her vanity. Seeing me there in all my glory, she patted the vanity stool as she scooted over a bit to make room for me. I strolled across the room and sat on her vanity stool. Cosmetics and accessories were neatly placed on the counter immediately below the large, round, illuminated mirror. "What is it, honey? Remember, for every problem, there's a solution!" She giggled a bit, draped her arm over my shoulder and replied "Yes, there is. But the solution to this one requires your trust, honesty and assistance. You do trust me, right? I nodded. "You can be honest with me, too, right?" Again, I nodded. "And, lastly, you're willing to help me, right?" Again, I nodded. As I nodded, I said "Of course, darling, you know I trust you, I'll always be honest with you and I always love helping you, it makes me feel needed. And being needed by you is the best. So, what's the problem?" I asked. Sherri turned to me, pursed her lips momentarily and asked, "What do you think of this new shade of lipstick, Terry?" "I like it a lot, it's very sexy. You know I love you wearing red lipstick. It's very hot." "I'm not so sure. I like it but it's difficult for me to decide by looking at myself in the mirror. I need to see it in different lighting conditions and such. That's where you come in." "How so?" "Like this" she said as she picked up the lipstick, removed the cap, screwed it to bring the tip out and started raising it to my face! "Whoa!" I said. "What are you doing?" "Isn't it obvious, Terry? I want to see what it looks like on you. Be a sport, honey." "But isn't that a little gay, darling? Men don't wear lipstick." "Don't be so uptight, Terry. I've seen you with my lipstick on hundreds of times." My heart practically stopped at that comment but I think I repressed outwardly looking shocked or scared. "I've seen you wearing my lipstick whenever we've make love, baby. I've always found it very sexy, you kissing me when we make love, the color transferring to your lips. It never seemed very gay to me, seeing you with my lipstick on as you thrust your cock into my wet pussy as we make love. We're just cutting out the middleman, or woman, as the case may be." Phew! For a second there, I was afraid that she knew of my secret passion for dressing as a woman. When we first started dating, one of the things that attracted me to her was her beautifully made up face. It seems that most guys like the "au naturel" look. I, on the other hand, was always attracted to the glamor girl type. As a child, watching "Gilligan's Island" reruns, most of my friends favored Mary Ann. I, on the other hand, was firmly entrenched in the Ginger Grant camp. Conversely, one of the things Sherri had initially liked about me was that, unlike others she had dated, I never complained that she wore too much makeup. Sherri was, of course, correct. Many times, no, every time after we made love, my lips ended up that same shade of whatever lipstick she wore. Much to my relief, my secret was safe. She had no idea that I loved her lipstick transferring to me when we made love or that I wore it myself, in private, along with a full array of cosmetics whenever I had the chance. If she only knew that one of my fantasies was for her to make me up fully! I feigned some resistance but eventually said "Uh, okay." Sherri obviously interpreted that to mean to continue, which she did. She cupped my chin with her left hand and brought the lipstick to my lips. I felt her apply it to the center of my upper lip and work outwards to the corners before proceeding to paint my bottom lip. Physically, the creamy texture felt nice on my lips, like a soothing lip balm, and it smelled heavenly. Emotionally, it felt nice for her to pamper me like this, feeling her soft had holding my face up as she applied the lovely color. It was as erotic as I had fantasized it would be. Realizing I was getting turned on by this, I tensed up. "There, all done! See, that wasn't so bad, was it? It looks lovely on you. I think we found your new shade," she laughingly said. "Go ahead, take a look." I turned my face to the mirror, focusing on my lips. They did look sexy. I nervously said, "It's a very lovely shade." Inside, I thought it looked a bit silly since I wasn't wearing any foundation, as I typically put that on first during my dress up sessions. Sherri said, "Hold on, let's add a bit of gloss. I just picked up a tub of Glassy Gloss by Wet N Wild. I usually use a similar higher end product but I was feeling a bit trampy and picked up this drugstore brand." She squeezed a small amount onto a lip brush and delicately applied it to my lips. "Hmm, that looks hot and slutty, baby. Here you go, put some on me, won't you?" So I did. It was like a fantasy come true, my wife and I putting makeup on each other. "You're right, Sherri. It does look hot and slutty. That gloss is so shiny I can practically see my reflection on your lips. "It certainly is and it looks adorable on you. But you seem so tense! Here, have one of my cigarettes" she said, sliding her pack of her extra-long all white Virginia Slims Menthol 120mm cigarettes to me. "A girl really should blot her lipstick and a cigarette does the trick nicely. And it's nice to see the lipstick on the filter." My hands were shaking a bit as I pulled a cigarette from the pack. They were so long, slim and dainty. I loved smoking them and had to purchase my own lest she noticed hers disappearing. I brought the cigarette to my lips and she brought her lighter up, flicked it and gave me a light. I inhaled deeply and exhaled the soothing mentholated smoke. As I drew the cigarette away from my face I held it so I could admire the marks from my painted lips. Geez, I was getting caught up in the moment and getting aroused. What would she think of that? As she lit a cigarette for herself, she laid a hand on my upper thigh and dug her long nails into me a bit. That did it. Now my cock was engorged and standing at attention. "Hmmm, it seems as if something else likes it, too," as she wrapped her hand around my hard cock. As we smoked and gazed at each other in the mirror, she started slowly pumping my turgid penis. A drop of precum emerged from the tip, which Sherri scooped into her mouth while moaning about how delicious it was. The next drop was much larger. Sherri again scooped it onto her finger but this time raised it up to my mouth. She smiled at me and said "Open up, baby", which I did. I clamped my lips around her fingers, savored the taste and texture and moaned, "Oh, you're right, that is tasty," pretending that I hadn't already tasted it hundreds, no thousands, of times. This continued on for several minutes. I was starting to feel a little funny, kind of tingly and said as much. "Don't worry, Terry, that's just the MDMA kicking in. You're right; I'm beginning to feel it, too." "Sherri, what's MDMA? Where did you get it? How and why are we on it?" "Don't worry, Terry, it's just the pharmaceutical version of what club kids call Ecstasy. Although it's widely used recreationally in the club scene, it does have legitimate therapeutic uses. It creates a sense of inner calm, a bit of euphoria and, most importantly, an enhanced sense of empathy, understanding and acceptance of yourself and others. As for where I got it, I got it from our client Paul Rogers, the pharmacologist. As for why I slipped it into your breakfast this morning, I thought it would make the very important discussion we're going to have go a lot easier." Sherri resumed stroking my cock, feeding me the precum whenever it emerged. I took another drag of the slender cigarette and asked, "What's this important discussion we're going to have?" "I know, Terry." "What do you know, Sherri?" "I know it all, Terry." "All what?" "Happy birthday, darling." "It's not my birthday, Sherri," I murmured as I exhaled another plume of smoke. "I know that, silly. Let me amend that. Happy birthday, Barbie D'Oliveira!" What!? Did she just call me "Barbie D'Oliveira," the screen name I use online? I should be freaking out but the drug induced calm permeating my mind and body prevailed. "But, but how?" I stammered. "Don't worry, Barbie, I'll explain it all in a bit. For now, just relax and let me stroke your lovely cock. If you don't happen to know, the Barbie Doll debuted at the American International Toy Show on March 9th, 1959. Since you've taken the name 'Barbie,' I thought it only fitting that you come out to the world, and me, on the same date. 'Barbie D'Oliveira' is a super cute name, too, baby. Whenever I introduce you, I may just say 'Barbie Doll' and throw in the 'iveira" like an afterthought." At that, she grasped my penis firmly and started stroking it rapidly. I took another drag on the cigarette and knew what was about to happen. I threw my head back and moaned, "I'm going to cum!" And I did. Before I realized what was happening, Sherri pointed my penis back at me and I felt jets of cum landing on my face, chest and stomach. The orgasm was so intense I found myself shivering and gasping for air. I lowered my face back down to gaze on the reflection in the mirror. My cum was all over me and it looked like one of the largest ejaculations I had ever had. I felt no sense of post-ejaculation guilt and admired all of the cum on my face and torso. Sherri was grinning at me like the proverbial cat that ate the canary. Spotting cum on my lips, I instinctively licked it off. Seeing me lick up my own cum drove Sherri wild. She exclaimed "Oh Barbie, you're so kinky!" and gave me an open mouthed kiss. She wiped a lot of cum off my stomach and licked it all off her fingers. She scooped up another batch and brought it to my lips. Following her example, I eagerly licked and suckled her fingers. "Look at you, you little hussy, lapping up that delicious cum like a hungry kitten. And you are. You're my own little Barbie Doll, my own little sex kitten." Running with the theme, I let out a little meow and did my best imitation of a purr. She responded by licking up the rest of the cum from my chest and face and fed it to me with her tongue. When it was all gone, she sucked and nibbled on my right nipple before coming up for a kiss that seemed to stretch on for eternity. Which was fine with me! But alas, eventually she pulled her lips off of mine and turned towards the mirror. My gaze followed hers and I had to agree when she said, "Our lips are a mess!" Not "My lips" but "Our lips." She pulled out one of the vanity's draws and pulled out a package labeled "Cosmetic Wipes." She gently wiped the smeared lipstick off of her lips and the areas around them. Then she turned to me and used the other side of the wipe to clean the lipstick off of my face. Thinking we were done, I started to get up. "Whoa, where do you think you're going, girlfriend?" she exclaimed as she gently indicated that I should stay where I was. Without waiting for a response, she turned back to the mirror. She then used a dark red lip pencil to draw an outline of her lips, straying beyond their natural shape at the arches and the center of the bottom lip. She then applied the lipstick and, using a brush, a coat of Glassy Gloss. She picked the lip liner pencil, turned to me and whispered, "Pucker up, baby." Still tingling from my orgasm and savoring the aftertaste of my cum, I didn't feign any protest and did as instructed. 60 seconds later my lips were painted as beautifully as hers. I saw Sherri's reflection smiling at me in the mirror as she raised her hand in front of her, her manicured and painted fingernails curled into her palm, except for her index finger. Clearly she wanted me to wait right here as she placed her other hand on my thigh and started to get up. Instead of walking away, she pivoted so that she was facing me. Cradling my jaw, she leaned in, lips puckered and gave me a peck on the lips. As a started to raise my hands to her hips to pull her in, she wriggled away. In the mirror's reflection, I saw her sashay to her bureau wriggling her hips provocatively. She rummaged in her lingerie drawer for a few moments, humming to herself. I couldn't see what was in her hands as she closed the drawer and strolled into the walk-in closet, still humming. She seemed to be taking her time but when she emerged, my jaw dropped. My glossy red lips sure looked sexy opened in the shape of an "O," looking like they were ready to give a blowjob. I turned around to admire the vision before me. Sherri stood there humming, framed by the closet door in a provocative stance, her outstretched arms reaching up the sides of the door frame. She was still nude from the waist up. Below, she was wearing lacy black panties, a garter belt, sheer black stockings and a pair of black stiletto heels. To top it off, she was wearing the honey blonde Dolly Parton wig she had worn last Halloween. She looked, for all intents and purposes, like an exotic dancer, dressed like that; her pert breasts thrust forward, her ass back. She winked at me and stepped back into the closet. Her humming changed to singing as she strutted out of the closet towards me. In a sexy little girl voice she sang: I wanna be loved by you, just you And nobody else but you I wanna be loved by you, alone! Boop-boop-a-doop! In one outstretched hand, she was twirling a pair of red silky panties. In the other, she had a pair of high heels dangling from her fingers. It was obvious what she had in mind. She stopped in front of me, holding out the panties and heels to me. After I took them, she placed her hands on her hips, lowered her chin, a bit to the side and waited. Knowing what was expected of me, I wriggled into the silky panties. As always, the panties felt amazing; they were so smooth compared to the tighty-whities I always wore. The outline of my penis, which was snug as a bug in a rug, was clearly visible. I traced its outIine with my index and middle fingers spread slightly, just like when I fingered Sherri's clitoris. A drop of clear fluid leaked from the tip of my penis and formed a droplet on the outside of the panties. Clearly, the silky material was not very absorbent. I used the tip of my fingers to rub the fluid against the outlined head of my penis. Oh my God, what a feeling. My cock twitched and an even larger droplet emerged through the material. My panties were going to be drenched, at this rate. This time, I scooped the fluid onto my fingertips, raised them to my lips and licked them clean. Mmm, yummy. I looked up to Sherri's smiling face, which turned down to the heels, one of her thin arched brows raised. I bent over and slipped my right foot into one of the shoes. They were red, open-toed, with four inch heels. I brought the strap around the back and buckled it. After I repeated the process for my left foot, I looked up to Sherri's smiling face. She swung a leg over my lap and sat down facing me, her arms draped over my shoulders. My mind was racing. On one hand, I was super turned on. You would be, too, if you could see my beautiful wife straddling your lap facing you, dressed like an exotic dancer. On the other hand, I was definitely kind of scared. She knew the screen name of my feminine alter ego! How much, what else, did she know? Why wasn't she upset? Was she going to punish me in some manner? What did she have planned for me, for us? She must not be upset. Here I was, wearing lipstick, lip gloss, panties and heels. She had just stroked me off and fed me my own cum. I loved her so much but I never thought this would be her reaction if she ever discovered my secret. She was beautiful, a free spirit, intelligent, the type of woman who turned heads when she entered the room. Despite her beauty, intelligence and wit, she never acted like she felt superior to her admirers, either men or woman. At parties, she expertly deflected advances from other men by shifting the focus of her attention to me or the men's spouses or dates. When anyone seemed to be jealous, envious or resentful of her beauty, she made a special, if discrete, effort to put them at ease, draw them out and win them over. While I was rather diminutive and quiet guy, I suppose I enjoyed a kind of an inherited or second-hand popularity with her admirers. I suppose they all figured I had something going on if I had landed a catch like Sherri. But this morning's kinky activities were definitely troubling me. Returning to the present, I asked, "What are you doing?" She simply grinned and resumed singing in that sexy little girl voice: I wanna kissed by you, just you Nobody else but you I wanna be kissed by you, alone! When she finished singing, she leaned in for just that - a kiss. Definitely more than a peck this time, but still cautious, obviously not wanting to mess up our lipstick. There it was again, "'our' lipstick." The trance she had me in was changing the way I thought, without repulsion or resistance. Still, I wanted to know what was going on and repeated myself. "Seriously, Sherri, what's going on?" To that, she simply smiled, started into my eyes and started rubbing her crotch on my penis, which was, once again, rising to the occasion. It felt heavenly, the silky material of our panties reducing any friction from the motion of her rubbing my shaft with her pussy, her clitoris rubbing the head of my cock. It was like she was masturbating herself on me. No, it wasn't like that, it was that. And I was enjoying it as she continued masturbating and singing: Boop-boop, I couldn't aspire To anything higher Than, filled with desire To make you my own! Boop-boop-a-doop, boop-boop-a-doop! "You've been a bad girl, Barbie. You've been keeping secrets from me. Not anymore. I'm going to make all of your fantasies come true, Barbie. I'm going to make you live out all of those kinky fantasies of yours, darling. When we're done, you'll be my own little sex kitten. My wife. My lover. My girlfriend. All wrapped into one sexy package - you! And I'm going to turn you into a very, very bad girl, baby." "I can't, I can't," I whimpered. "I just can't do all the things I've fantasized about, Sherri. How can I?" "Oh, Barbie, don't worry. You can do it. You will do it. You know why? For two very good reasons. One is that you want to. Two is that if you don't, I WILL leave you. Why would I leave? You think I can stand to watch someone I love not pursue their dreams? How could you ever be truly happy? Do you think that I could ever forgive you if you denied me the pleasures that this path will bring us? I do mean us, darling. I'll be there every step of the way, supporting you and sharing the joys, carnal and otherwise. Sherri resumed rubbing her clitoris against the head of my cock through my panties. "My eyes are closed; I'm imagining I'm riding my sexy Barbie right now." The pace and force of her thrusts increased. I feel your breasts rubbing against mine, our erect nipples brushing against each other again and again. I can feel the flowing locks of your long tresses caressing the backs of my hand as I dig my nails into your back." Her pace increased even more as she dug her nails into my back. "I can see us gazing into each other's eyes, the joy in our faces as we suck another sexy girl's cock and it erupts onto our lips. Your mind may have doubts but your cock is saying, 'yes, yes, YES!'" I could feel her velvety labia wrapped around my pantie encased wand as it ejaculated for the second time this morning. She tilted her head back, starting shaking it back and forth in sync with her thrusts, her hair flying like a delicate fan and yelled "YES. YES. YES" in a drawn out wail at the top of her lungs over and over again. She was shuddering and trembling uncontrollably. Her juices kept secreting and my panties were totally soaked. It seemed that she was yelling for hours but surely it must have just been minutes. As her orgasm subsided, she draped her limp body over mine. "Just put your kinky sexy self in my hands, trust me and we'll live out your fantasies together, darling. You know why else you're going to do it, Barbie?" She started kissing, licking and nibbling my neck and murmured. "Because if you don't, I'm going to fucking KILL you, that's why!" and laughed deliriously. At that, she started sucking on my neck so hard I knew I was going to have the first hickey I've had since I was a teenager. I felt her body shift as she planted her feet on the floor and stood. "Boop-boop-a doop, enough serious talk for now, let's get started, there's no time like the present." At that, she gently grasped my hand and led me towards the bathroom. There was no doubt. My fate was sealed. It was a foregone conclusion. There was no point resisting. All I could do was hang on and enjoy the wild ride my life was about to take. Chapter Two - Barbie's Discovery When we went into the bathroom, Sherri proceeded to the tub, turned the water on and adjusted it until she was satisfied that the temperature was just right. She stood up and matter-of-factly said, "Here you go Barbie. Shave your legs and I'll tell you how I discovered your secret desires." She set down four pink disposable razors, saying "This being your first time, it's going to be a bit messy, so don't close the drain plug. Just lather up the bottom half of one leg and get started. Rinse the blade after every stroke. Those ugly long hairs will still tend to clog the blades so, when they do, just press the blades against your skin and push the razor away from you. That should clear things up. " I stepped out of the heels and removed my cum-soaked panties. Sherri took them from my hands, started sniffing and licking our fluids off them. I sat down in the tub. I cupped some of the warm water over the lower half of my right leg and got started. The deep recesses of my mind knew I should be afraid of where this was all going but, between my excitement and the MDMA, I didn't hesitate. Sherri sat down on the commode, lit another cigarette and proceeded to tell me of her discovery. "Remember about six weeks ago, I held that open house for the Arroz transaction? Well, things were pretty slow and boring, until one particular man came in, that is. He came in and said, 'Your husband is a real cock tease. He said he wanted to suck my cock and let me fuck him in the ass but refused to follow through. He really is a ditzy bimbo, too. What? He didn't think I'd put two and two together. He never should have used his real last name with it being plastered all over town on real estate signs. Here, take a look at these.'" He dumped a stack of papers on the table. I started to tremble as I browsed through printouts of your online profiles on FetLife and TrannyDate, as well as transcripts of your chat session with him. He couldn't miss the look of anger that came over my face. I guess he thought he had accomplished his mission seeing me trembling, short of breath and angry as he left. What the asshole didn't realize is that he totally misinterpreted my reactions." "Yes, I was angry. Not with you but with him. How dare he try to piss me off this way? How dare he try to humiliate and destroy the love of my life this way? Yes, I was trembling and short of breath. Not from shock, but from excitement. He was right, though. You really are a cock tease. I can understand how he would be disappointed, the way you said you wanted to suck his cock till he came in your mouth and keep sucking until he was hard again so he could fuck your ass for a long time until he came in there, too. Of course, the papers included the photographs you posted and screen captures of your web cam sessions. It was so hot, Barbie, seeing you with a vibrator shoved up your ass, cum dripping from your penis as you licked your cum coated fingers. You're actually very pretty, Barbie, despite the limitations you've placed on yourself by trying to keep all of this a secret. When I'm done with you, you'll be a total knockout." "You look kind of surprised by my reaction to his revelations, Barbie. You shouldn't be, not really. Of course you already know that I'm uninhibited and adventurous. We fucked on our first date, as I'm sure you recall. I enjoy it when you fuck my ass. I obviously enjoy sucking you until you cum in my mouth for me to swallow. The point being is that I'm no prude. But women have secrets, too, you know. And that includes me. What you don't know is that in high school and college I definitely had a reputation of being kind of a slut. What can I say? I enjoy sex. And not just with men but also women. You've met my college roommate Bonnie. What I never told you is that we were lovers all through college. Well, except for the times when we were sleeping with all the hunks on campus, that is. I can't even begin to count how many I fucked but rest assured that it was a lot. Once I met you, mister prim and proper, I suppressed my wild side and strived to be the kind of wife I thought you wanted. So, in a way, I too have repressed myself because I didn't think you'd accept or be able to handle the 'real' me." At that point, I was finished with my lower right leg. I cupped water in my palms and rinsed the remnants of the shaving cream and hair off my calf. It felt amazing feeling my hands caress the now smooth and hairless skin. It felt so nice, I grew erect. This didn't escape Sherri's attention, who said, "I see you're enjoying the results Barbie. Now start on the other leg." Using the same razor, I proceeded shaving the lower half of my left leg. Sherri continued. "Despite all my experience, I must confess that I've never been with a woman with a penis before. I was actually kind of ignorant about the scene. Sure, I know there are men who live as women. I even know some such women. But I'm certainly not ignorant anymore, I've done my research, learned the differences between transvestites, cross dressers, transsexuals, transgendered and so forth. Before my research, I just kind of lumped people into broad categories, such as men who felt they were born in the wrong body and wanted surgery to correct that, drag queens and such. But I digress; we'll get back to this later." "But anyway, once I knew about your secret I knew I really had to learn more about your desires. I must confess that some of my methods were quite underhanded, darling. I hope that you'll forgive me. The first thing I did was to create my own accounts on those web sites and send you friend requests. I installed keystroke logging software on your computer so that I could learn your passwords, log into your account and read your correspondence. I installed remote access software on your computer as well so I could watch what you were up to in real time. I've watched a lot of your open web cam sessions, too. By the way, thank you for all the orgasms that those gave me!" "Perhaps you're wondering how I found the time and skills to do all that. You know all those all day and weeklong professional development classes I've supposedly been taking lately? There hasn't been a single real class the whole time. I've been using the time to see what you'd get up to in my absence. Robbie, the I.T. guy down at the office showed me how to install and use the keystroke logging and remote access software. He's quite enamored with you, incidentally, he's a real delightful pervert, too. We've both been so turned on watching you that it took all my willpower not to suck his cock right there in the office! You can't imagine how difficult it is to resist sucking a hard cock when it's right there within reach. But I was a good girl. I'm sure that whenever he got up to go to the bathroom that he was actually jerking off thinking of your kinky shows. "I've been monitoring what erotic stories you've downloaded from those Fictionmania and Nifty web sites. The Second Life. The School Tramp. Lisa Finds Herself. A Boy can Dream. All those stories by Vickie Tern and Michelle Nylons. You've got a nice little collection of very sexy erotica going there, girlfriend. Once I'm done with you, we may have to invite the authors for visits so you can thank them properly for their inspiration. Let them enjoy the fruits of their labor, so to speak. Don't you think that would be nice?" "I've been watching all the shemale porn you've downloaded from sites like ashemaletube, xhamster, pornhub and such. Amazing! I had no idea that such beautiful women with such lovely cocks and big breasts could be so alluring. I can't tell you how many times I've masturbated watching those sexy babes sucking huge cocks and taking them up their asses." "You don't know it, but we've even chatted online, you just didn't know it was me, with my fake profile and all. I was quite touched and flattered, sweetheart. You told me how you dreamt of revealing your secrets to me. How you wished that I would accept and encourage you to become the bimbo slut of your dreams. How you wished that we would do each other's makeup and then go out on dates together, have lots of kinky sex with other partners together. How you'd like to live as a woman fulltime. But how you feared that I would reject and leave you. How you didn't know if you could go on if you lost me. How you hated yourself for not being honest with me from the start. Feeling trapped between your secret desires and your love for me. How you stupidly concluded that you'd rather live a life of quiet desperation than to lose me. That really was stupid, darling. How can anyone truly love you if they don't truly know you? I was literally sobbing during the chat session, learning how much angst and pain you've been going through. I almost revealed that you were actually chatting with me but simply encouraged you to reveal yourself to 'her'. That if she truly loved you, she'd accept and encourage you. And that if she didn't, that you'd be better off if she left you, leaving you free to pursue your self-actualization, to take the world head on, on your own terms. But I do love you. I accept you. You obviously never revealed yourself to me, so I've spent some time planning this special birthday for you. At that point, I was done with the lower half of my left leg. Sherri told me to remain sitting but to push myself back in the tub, straighten my legs out and shave the upper front sections of my knees and legs with the second razor. "But enough maudlin talk, let's move on. Furthermore, I established contact with some of the girls you've been chatting and camming with online. I introduced myself, told them who I was and what I was up to. I got them to encourage you to share your fantasies, to draw them out of you, not that you displayed much resistance. I'm particularly fond of and grateful to Gabrielle from Las Vegas. I can see why you like her so much. She's so beautiful, so bubbly and vivacious. And my god, those tits and that cock! Simply stunning. I've invited her to visit us in a few weeks, by the way. I can't wait to meet her in person, to see her drilling your mouth and ass with that huge clit of hers." At that point, Sherri stopped her monologue and smoked and rubbed her clit between her fingers while I finished up this stage of my shaving. "Now stand up and use the third razor to shave the back and upper portion of your legs, sexy," Sherri instructed before continuing her monologue. "The conclusion being is that I think I've got a pretty good handle on what kind of woman you are, that you want to be. You aspire to be a glamorous, sexy, woman. You dream of having large breasts, large enough and with enough cleavage to be fuckable. You want full soft lips that look like they were made to suck cock. You dream of laying back, smoking a cigarette, seeing a cock sliding between your breasts until it cums all over your face. You want long, blonde feathered hair with pink frosted tips. You definitely have a bit of a smoking fetish and you do look adorable smoking those 120s. You're attracted to similarly sexy women, especially those with cocks. You're also curious about being made love to by men. You love heavy colorful makeup, not that 'natural' look that is so popular these days. You want to be a woman that's proud of having a cock, that wants to use it, not keep it locked up in a cage like all those sissies online. You dream of continuing our real estate team but with both of us as the sexy bimbo types. You want to be open about being a woman with a cock, not trying to hide it and fearing discovery. You fantasize about us starting our own brokerage and naming it 'Transitions.' You yearn for us to engage in all sorts of kinky sexual escapades together." Damn! She really did know everything. But, crap, these were just fantasies, fueled by years of repression. I can't actually follow through on them, can I? "Well, Barbie, I hope you're ready because all of those dreams are going to come true. I see you're done shaving. Now do it all again with the fourth razor to get any strays that you may have missed. But, really, some of those marketing ideas for Transitions Realty are kind of over the top, don't you think? However titillating it would be, I'm not going to post advertisements all over town that say 'Happy endings guaranteed!' I'm not going to let you post advertisements on bus benches with a photograph of your face and breasts captioned with "Sit on my face. Please!' The idea of an advertisement with before and after photos of you captioned 'Ready for a change? So was I. See what I've accomplished? Let's see what I can do for you.' is kind of cute, though. That all being said, I'm sure that with our business acumen we can come up with promotional materials that aren't so graphic but are still sexy. Sex does sell, after all. I'm sure we'll reach happy but effective compromises. I can understand the desire to be a total bimbo but we'll need to tone it down just a little, at least for work. Besides, men go wild for an elegant woman who also knows how to and enjoys being a trampy slut. We have to inspire potential clients to believe that we have the class and elegance to handle their important real estate needs. I see that you're all done. Now, take a shower to rinse off. While you're at it, here's another razor. Shave your arms, underarms and torso while you're at it. We want you nice and smooth before our fist appointment." "Our first appointment?" I asked. "Yes, our first appointment, down at 'A Cut Above.' A total makeover for you and some touchups and enhancements for me. Now that I'm going to have some competition in the household, I'm going to have to step up my game. You don't think I'm going to let you go full bimbo while I stay Miss Prim & Proper, do you? They're expecting us at noon and so looking forward to meeting you in person." "In person?" "Yes, in person, darling. When I told my hairdresser Heather about what I was up to, one thing led to another. Heather and the rest of the girls were so intrigued; we've taken to gathering in the salon office to watch your webcam sessions on a regular basis. And guess what. Heather has a cock! So do some of the other girls that work there. They've been so turned on watching your shows; they've whipped them out and masturbated with me standing right there every time. It took all of my will power to resist sucking each one of them to completion then and there. They really are evil bitches, the way they tormented me. Saying things like 'Here you go, Sherri, suck my she cock, I know you want to,' 'Oh, Barbie's going to look delectable sucking our cocks,' 'I can't wait to see the look on your face when you see my cock fucking Barbie's ass' & 'It's going to be so sweet when we have you and Barbie on your knees, butts up in the air, watching you holding hands and kissing while we take you both from behind.' But I remained faithful, as you've been with me. There will soon be plenty of time for us to explore our carnal desires together. Anyway, transforming men into women is kind of a special business niche of theirs and they can't wait to get their hands on you. You wouldn't believe what they did for some young ladies named Ruby and Kandy recently. I'm sure you'll want to jump their bones but I'm hesitant, they're both underage. But don't worry. Heather has kindly agreed to initiate you into the joys of transgender lesbian, or transbian, lovemaking. She's coming over this evening. I can't wait to see you sucking her cock. She assures me that she'll be able to get it back up to give you a proper fucking, too. I've seen how much you enjoy your vibrators. Just you wait till you get the real thing, baby; you're going to love it! Now hurry up. While you finish up, I'll get ready and we'll get going. After I give you a few birthday presents, that is. Oh, these transitions are going to be so much fun!

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Amber and Jake - An Altered Fates Story By Eric Edits by SteveZ Part 6 Jake awoke the next morning feeling wonderful; she kissed her lover Bob gently as he began to stir. It was great to feel so sexy. She padded over to the mirror and looked admiringly at her - at Amber's body. 'Well, in many ways it was tempting to see if Amber would be willing to trade bodies and lives,' she thought, 'but I love most of my own life too! I'm rich, have a great job, my income from all sources is...

4 years ago
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Love Me til Dawn The Final Chapters

It was not for another four months before Alice had Lorraine alone to herself again and in a position to discuss it with her.Upon their return from San Monique she had begun an intensive management course designed to give her the basic knowledge she needed. She would never need to do any bookkeeping but it was vital that she could interpret the accounts. Alice had some experience in her previous job as a clerk that helped her understand the accounts sufficiently. She was taught the different...

7 months ago
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Spread sex into chapters

A Russian, mature aunt just loves to play pranks with an experienced, hormonally excited, strong male - this is exactly the name you can give to this story, which tells how my neighbor… A Russian, mature aunt just loves to play pranks with an experienced, hormonally excited, strong male - this is exactly the name you can give to this story, which tells how my neighbor friend loves to masturbate experienced guys. She loves to give a blowjob, and we are happy to show everyone who wants to...

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4 years ago
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Transition Machine

Daniel awoke in total confusion, he couldn’t remember falling asleep or where he was or what he was doing before he woke up. His eyes were heavy and he felt so weak that he could barely even lift his eyelids, he couldn’t lift or move anything actually. He felt the cool air around him, he was obviously in an air conditioned room. For a second Daniel thought that he had been in an accident and that he was waking up in a hospital but then he smelled something. The perfume scent that had just made...

4 years ago
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Transition Decisions

Transition Decisions by Vivian Bird I met her at an art gallery. We happened to be looking at the same painting and she sat down on the same bench that I was on. She looked like a goddess, tall, thin, beautiful and sexy. Her tight skirt was black, with a kick pleat in the back. Her long sleeved, white blouse was billowy, with ruffles in the front. She had two buttons undone, showing just the hint of cleavage. Her blond hair cascaded around her shoulders and she used her hands...

3 years ago
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Transition

Keywords The Operation Categories TG Synopsis: John started life male and ended female. His transition has been experienced by many. For John it was not fun -- not all that he expected. Transition By Janet Baker My divorce was finalized yesterday. The registered letter came to my efficiency apartment this morning. My life as I knew it was over. I had to start anew. I am so lonely. I got what I wanted, I am now a woman. My transition is...

3 years ago
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Transitioning To College 4

In this concluding chapter in the story of Taylor's unusual strategy to get into Northwestern University, the pretending becomes so much more. Saturday night as a guest at a wedding becomes a date with fate. TRANSITIONING TO COLLEGE --- By Nina Adams Part 4 Chapter 12: It felt almost foreign to get ready for school Monday morning. I wore baggy jeans and a Nirvana long-sleeve jersey. I made sure there was no leftover makeup on my face and I removed the polish on my...

3 years ago
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Transitioning

Amber Yates is just twenty-four years old and practically fresh out of college. With red hair and a banging body she could be a runway model rather than a therapist working in alien affairs on Sierra OneOne. With a tiny waist, generous by perky breasts and a wonderful petite ass with just the right amount of flair to her hips, she is the talk and the envy of the office. Overall she looks delicious. Ustir has been aching to get to see what other human qualities she has other than helping him...

3 years ago
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Transition in Lessor Plumpton

The private bar of the Cock Inn, Lesser Plumpton was a bit more private than most. The residents of the village used it for orgies to which selected paying guests were invited. Currently it was occupied by a couple of country solicitors a doctor. A lab technician and their business people spouses who were fucking as if it was going out of fashion.Di was the Cocks part time cook and had just finished deserts so she went through to the bar to chat to the barmaid. Lisa was filling in as the...

2 years ago
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TRANSIT STRIKE

My name if Jeff. At the time of this story I worked downtown Toronto in a large office building I was twenty five and single. As soon a rumors started about a possible transit strike the people started organizing car pools. We were told we could park around the building at no charge during the strike. I said I didn't need a ride because I would ride my bike.. Everyone knew I rode a motorcycle. Jessica, one of the ladies asked if I could give her a ride so I agreed to give her a ride. Over...

3 years ago
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Transition to Vikki part eight reworked

Transition to Vikki part eight (reworked)Chapters one through eight of original story, completely rewritten (final draft). Story continues from chapter nine as My transition to Vikki.The story continues. Vikki settles into her new surroundings and with new friends. Plans are made for a visit and the club is seen for the first time.As with the others, this part has been heavily revised since first writing. Typo's, grammar and story plot mistakes have been corrected. Best to read these chapters...

2 years ago
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Transition to Vikki part six reworked

Transition to Vikki, part six (reworked)Chapters one through eight of original story, completely rewritten (final draft). Story continues from chapter nine as My transition to Vikki.Next chapter of Steven's change into becoming Vikki, initial steps are taken and new friends made.This is the next part of the story, like those before it has been taken back to the laptop and reworked. Additions have been made, some other parts were removed. Typo's were corrected, grammar has been brushed up and...

3 years ago
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Transition to Vikki part five reworked

Transition to Vikki, part five (reworked)Chapters one through eight of original story, completely rewritten (final draft). Story continues from chapter nine as My transition to Vikki.Continuing the story of Steve, Gina and Valerie's sexual adventures after his first encounter. This is the next reworked chapter in the story. Altered, edited and amended to remove typos, grammar errors and story cock ups. This follows the previous parts one to four amended editions.As I've seen from other people's...

3 years ago
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Transition to Vikki part four reworked

Transition to Vikki, part four (reworked)Chapters one through eight of original story, completely rewritten (final draft). Story continues from chapter nine as My transition to Vikki.Next part of Steven Jennings' tale how he abandons his old life to become Vikki. Valerie and Gina get closer and more life stories are told. This is updated from the original scripts.All original chapters have been rewritten and updated. Typos corrected, grammar put right and plot errors sorted out. Parts have bee...

2 years ago
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Transition to Vikki part three reworked

Transition to Vikki, part three (reworked)Chapters one through eight of original story, completely rewritten (final draft). Story continues from chapter nine as My transition to Vikki.Next part of how Steven Jennings became Vikki. A new playmate is encountered and life stories of the main characters begin to be told. Following after the two newer rewrites, this one has also been updated. Typos have been corrected, grammar put straight and plot errors sorted out. Some parts have been added,...

3 years ago
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Transition to Vikki part two reworked

Transition to Vikki, part two (reworked)Chapters one through eight of original story, completely rewritten (final draft). Story continues from chapter nine as My transition to Vikki.Continuing the story of Steven Jennings, Gina and his transformation to Vikki. This is part two of the reworked original story. All original scripts have been rewritten to this new format. Changes have been made to streamline the story where I thought it was needed. Typos corrected, grammar put right and story plot...

4 years ago
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Transition to Vikki part one reworked

Transition to Vikki, part one (reworked)Chapters one through eight of original story, completely rewritten (final draft). Story continues from chapter nine as My transition to Vikki.The full story of Steven Jennings and how he left his previous life behind for someone new.This story takes numerous chapters to tell. After most of the original drafts were written well over a year ago, I thought it was high time to take them back to the laptop and look at them again. There they were read through,...

3 years ago
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Transitioning to College 1

Transitioning To College Chapter 1: To some kids college is just a consideration or pipe dream. In my family it was assumed that high school graduation would be just the kicking off point for my real education. My father had been a doctor, my mother graduated with honors from Michigan and my sister was in her first year at Duke. Going to college was a given. The only questions were to which school and what I would major in. With my sister out of the house my mother and I lived alone...

2 years ago
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Transition

Transition Janet L. Stickney [email protected] The announcement was met with both jeers and cheers. Costume parties in a high school were rare, but they billed it as something else. The school called it the "Who Am I" day. Anyone could dress as any person or character, kind of like cosplay. My mom told me her idea which was crazy, but I was intrigued and nodded my head yes. She had given me three choices. Wonder Woman, Cinderella, or Dorothy from the Wizard of Oz. Not one...

4 years ago
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Transition to Vikki part 10

Transition to Vikki, part tenVikki has her first party night, the weekend continues.This has been rewritten from the original script. Typo's and grammar have been corrected. Story gaps and mistakes put right. Some parts have been added to, others either cut and even some removed. Nothing in the main plot has been affected by these changesChapter lengths have been cut to ensure a more even format. Reading this story,it is better if you keep to this new version, it makes things so much simpler,...

2 years ago
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Transition to Vikki part 10

Transition to Vikki, part tenChapters one through eight of original story, completely rewritten (final draft). Vikki has her first party night, the weekend continues.This has been rewritten from the original script. Typo's and grammar have been corrected. Story gaps and mistakes put right. Some parts have been added to, others either cut and even some removed. Nothing in the main plot has been affected by these changesChapter lengths have been cut to ensure a more even format. Reading this...

2 years ago
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Transition to Vikki part nine

Transition to Vikki, part nineChapters one through eight of original story, completely rewritten (final draft). Story continues here in chapter nineStory continues as Vikki shows them their new country house and prepares for the weekend. This chapter has a lot of narrative. Just think of it all as the necessary groundwork for new settings, characters and story plots to come. So please, bear with it.All the original chapters have been rewritten to remove errors. Typo's, grammar and story plot...

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