Crossdressing HD Porn Videos

3 years ago
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Maid to be Submissive Part One

As I stared up at the ceiling, contemplating my own existence, I couldn't help but retrace the last few weeks in my mind. My girlfriend had just broken up with me, apparently, she had met someone else and had been cheating on me for months.The same week, I found out that my company was laying people off and I was about to lose my job too. This is how I ended up at age twenty-five, living with my mom again.It wasn't all bad, I thought, trying to convince myself. My mom owned a long-stay motel,...

3 years ago
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Crossing A Different Line

In my personal journey from straight, married heterosexual to bi male, I discovered, along the way, that I was aroused by women’s lingerie. It started with trying on a pair of my wife’s nylon panties. The feel of the silky material, and the sight of how it fit, quickly brought on an erection. I used another silky pair in my hand to jack myself off, being careful not to get any cum on the panties. The orgasm was unusually powerful. In the weeks following, I pursued my new found curiosity,...

3 years ago
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Losing my virginity

I'm a 21 year old attractive crossdresser from Mumbai, India. I am sharing a true story of how my roommate turned into a permanent fuck buddy!I've been crossdressing for 10 yrs now and have my own collection of all kinds of stuff you can think of. I moved into the city 2 years back and rented an apartment with a guy called Vishal who I didn't know at the time. The first few days went in unpacking and setting up my room and trying to build a decent rapport with Vishal, have some drinks once a...

3 years ago
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Caught dressed like a sissy slut

My girlfriend was away for the weekend so I had the place to myself. I was feeling incredibly horny so I went through her knicker drawer and decided to dress up (which I've enjoyed many times before). I put on a really tight, pink thong, black fishnet stockings and suspenders, and her black mini skirt. I looked at myself in our full-length mirrored wardrobes. God, I looked so sexy and couldn't control myself. I got on my hands and knees and pushed my ass into the air, letting the skirt ride up...

3 years ago
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Confessions of a Sex Crazy Crossdresser Part 9

Hi all, hope you enjoy Sandy's adventures. Chapter 17: Viva Las Vegas Peggy and I woke up in each others arms around 5 AM and we made love again. Then at 6AM when we both had to get up we showered and made love again under the water in the shower. We were avoiding the subjects of me leaving for Las Vegas today and her having to be at work at 8:00. I drove Peg to her apartment on the Northwest section of Phoenix and we exchanged phone numbers. I told her I would call her from Las Vegas and...

3 years ago
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Noodles Part 3

The morning greeted me with a gentle ray of light escaping from the corner of the blinds on my bedroom window. As the fog between sleep and awake began to dissipate, I remembered why I was waking up wearing a dress. I went to bed as a girl last night. And I had decided that I wanted to wake up as one in the morning. I pulled the covers off of me and smiled at the sight of my beautiful shape. I hadn't even removed my heels. As the rest of my senses caught up to my eyes, I suddenly remembered...

3 years ago
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The Feminisation of Michael Chapter 7

The Feminisation of Michael. Chapter 7 I settled in at Stanmore House quickly and Sam helped a lot and we would spend most days together with her showing me around the estate. I soon persuaded Sam to wear prettier things and we were often seen., me blonde, her brunette, rushing around giggling in little floral dresses. Alternatively we would ride the beautiful horses in our jodhpurs and white lace blouses. I got very fond of a jet black horse called “Star” that moved like a racehorse. ...

3 years ago
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From Sam to Sarah A Genre Bending Story of Personal and Sexual Discovery Chapter 3

Aubrey had just finished building up my confidence to the point where I was ready, as ready as I would ever be, to cross the threshold of that door and make my first public appearance as Sarah, the female persona she had helped create for me to trick her side-guy into letting me watch them fuck. She told everyone that I was her lesbian roommate; that was the cover.Our heels clicked on the pavement. We held hands, our painted fingernails intertwined, as we walked to the door. As we approached, I...

3 years ago
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A Whole New Me Part 2

I had just finished cleaning up in the bathroom. A spontaneous encounter with my best friend whilst wearing my girlfriend’s thong had left me a bit of a mess and as for the thong... well I guess I’d need to find something new. Fully cleaned up, I ran naked into our bedroom and started looking through Lisa’s drawers for a new pair of panties. I wasn’t sure how I’d explain my change to her but I guess I could think of something if I washed the thong too. In the end, I pulled on a pair of sheer...

3 years ago
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serving my master part 1

    My name is Chris I may have a penis but deep down I was born a girl. I have long red hair baby blue eyes a soft shapely hairless body and an overpowering obsession for wearing frilly lingerie. My obsession started at a young age I found a pair of my sisters panties in the bathroom and took them back to my room. I stripped off my clothes and rubbed the dirty panties over my face inhaling her scent. My penis grew as I though of what it must be like to be a girl and get to wear such pretty...

3 years ago
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My First Thong

When I was a little boy in grade school, I developed a curiosity so strong that it could not dare be mentioned to my parents...well, except for my father, since he was quite a perv despite being married to my mother who was more conservative than he was. Typical behaviors in a hispanic couple's life, really. No, it was not about my sexuality, but it involved underwear. Specifically, a particular female underwear that grabs many a man's attention, because the way it looked on a woman, was that...

3 years ago
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Becoming a Sissy

For the longest time I can remember loving the look of pantyhose on a woman. It made their legs look so sexy and especially when they wore heels. I would always jack off while looking at pictures of women in pantyhose in magazines. So one day after turning sixteen I got the nerve to try on a pair of my aunt's hose. OMG they felt amazing and the way they made my legs look so smooth and sexy was a huge turn on. So mush that I had to lay there and masturbate. They also made me feel feminine. I'd...

3 years ago
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Mom made me a Fluffer

For most of my life I never knew exactly what my mom had done for work, neither did I know who my dad was. As such I just continued with life and thought to myself that I would find out what she did in time.My curiosity first peaked when I was 16, I was looking for my moms purse so I could exchange some of the money I got mowing lawns for people around my neighborhood for different bills. My search eventually leads to her underwear drawer where I do find her stash of extra money so I can change...

3 years ago
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Being Christy Part 5

Leading me towards the bed, Nick pulled me into his arms and I willingly let him. I lifted my face to his and parted my lips, inviting him to kiss me. Our tongues probed each other, our lips moist and eager. Nick was moving his hands all over me – to my face, my neck, then travelling firmly down to my sensitive waist and kneading my panty-clad buttocks.I couldn’t help myself from melting into him – I felt as if he was all over me, consuming me, and I loved it. I could feel his prick begin to...

3 years ago
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Crossdresser in Love

I woke up with my hands bound, my mouth gagged, and my ass plugged. The bed I was on was comfortable enough. This was just a reminder that these parts of my body were no longer mine to do with as I pleased. For tonight would be my wedding night. For months we had planned things out. Picking out a dress, a place for the ceremony, all the things that brides do with their future husbands. But for me, it also included a regimen of hormones to complete my becoming as feminine as can be for my man. I...

3 years ago
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A New Friend at the Adult Toy Store

I decided to go to my favorite Adult Toy Store.  Now, this is not one of those dark, dingy places that make you feel uncomfortable.  It is well lit and attractive.  The people who work there are very nice, polite, helpful and make you feel right at home.  So I can go and feel at ease while I browse.  This store carries lingerie, clothing for clubs or stripping, stripper shoes, toys, and videos. Because I was driving straight to this store and then home again I decided to be a little more daring...

3 years ago
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Memories

Just for fun, I though it might be nice to share some of the experiences I went through on my way to becoming the sexy slut I am. Before I had the confidence to fully dress and go out, and to go on the few dates I've been on, I was completely closeted. The only way I could express my girly side was through playing on the phone and all alone. I loved dressing up a few times a week. I collected sexy underwear from ex-girlfriends who left stuff behind, and from a few rare shopping trips where I...

3 years ago
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Caught

I see all these girls with the first time or the first time they got caught dressing and it turns me on looking back and thinking of mine. Well I was young when I started getting into my moms and soon to be step sister’s clothes. My mother divorced my father when I was young but never really knew my dad do to the fact that he was always in the military and my mother was tired of moving place to place. She started dating a man, Rick, which had a daughter, Melissa that was several   years older....

3 years ago
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Hidden in Plain Sight The Conclusion

It was one of the longest weeks of his young life that Marc could recall. When he wasn't attending his regular classes he was at baseball practice where continued to amaze his coaches and team members with his prowess on the ball diamond. When he was alone he thought about Charlene and couldn't wait to see her again.Friday night was game night and the fans filled the bleachers to cheer their home team on. From his place in the outfield, he tried to scan the crowd in hopes of seeing...

3 years ago
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Jessie and Sue s date concludes

I could not believe I was going out with Sue on a date. It was our first date and she appeared to be my match made in heaven. First, we got caught with my face between her thighs while wearing lingerie in a department store dressing room. Next, we made our way to the shoe shop where not only did Sue buy me a killer set of four-inch heels that were strappy, brown open-toed sandals with little jewels on them, but the store clerk named Becky got me all dressed up en femme. Then when Sue took me...

3 years ago
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A surprise helping hand

When I initially started to cross dress I would borrow things from those around me. At first it was my sister, then when I visited my father I would wear my step mother's things and eventually my girlfriend's. Mostly without their knowledge, of course. I was always as careful as I could possibly be, replacing things just as they had been left and making sure I had plenty of time when I indulged my habit. When we first moved to my home town when I was very small there was a family next door who...

3 years ago
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Getting More Daring At The Bookstore

It was late spring, almost summer. It was too hot to wear my usual jeans and tight shirt, covered with a coat, to the adult book store. I was also getting bored with the same outfit every time. Since I was usually accepted, once inside, as a woman of sorts, I thought I’d push the envelope further. Someone had given me a t-shirt years ago that was far too big for me. I kept it in my shed for a possible large rag. I went in and tried it on. The bottom of it was below my ass. I put it in my...

3 years ago
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Car Park

I finally got the nerve to go out in public dressed. I've been dressing in private for years. It started with panties, Some of my wife's, some of in-laws that have stayed with us from time to time.I finally got the nerve to buy some at a store. So exciting, looking at panties wondering how they will look on you. Took a while to find my correct size; I like them tight not no so tight I fall out of them. Some were so big they looked my something my grandma would wear. I now have collected a nice...

3 years ago
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Spying On My Sissy Slut Husband Part Two

After my last story of how my husband and I became lesbian lovers with him dressed as a female, both of us thought a lot about what was next for us.  I did tell him that I wanted to see him with a man.  Then that got me to thinking about a bisexual couple to play with.  A bi woman for me and a bi guy willing to fuck a crossdresser.  That would be perfect but so hard to find.My husband and I set a date for our attempt to find him a one-night stand playmate to fuck him.  The rules were set.  We...

3 years ago
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A New Level

Greg and I had been seeing each other for a little while at this point, and things were going great. We had gone on a few dates and I loved how he always treated me like a lady. He made me feel so sweet, sexy, and vulnerable. Tonight was four months since our first night together and I wanted to surprise him with something a little special. I bought a long coat, and I thought it would be fun to show up at his door wearing nothing but the coat and some sexy lingerie. I slid on a sexy pink and...

3 years ago
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My Secret Revealed

My life was pretty good. I had an excellent job that paid well and afforded a nice mobile home. I played baseball on the company team and had a bevy of office hotties show up to the games to cheer me on, I even dated a few of them briefly. It was the nights that I really looked forward to.Once the day was done and I was safely behind the drawn drapes and locked doors of my trailer that I indulged myself in my new habit. Fresh from a shower I dug out the erotic lingerie that he had...

3 years ago
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A surprise ass fucking in panties

A very curious thing happened to me the other day and I feel I need to share it with you... I have been 'mildly’ crossdressing for over a year now. I say 'mildly' because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it's like having your whole lower half caressed persistently. I have thought of wearing a bra but, although I can almost...

3 years ago
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48 Hours Chapter 4

Chapter 4: An Interesting TailChris stirred, and momentarily wondered why he felt so nice, quickly realising that Lynn was at work on his cock again. He closed his eyes and enjoyed the feeling as he grew in her mouth, the subtle vibration of her moans causing him to twitch and shiver.He looked down, and she looked up, running her tongue from his balls to his glans and then, not stopping, over his chest, kissing gently as she progressed until finally placing her moist warm lips on his."Hello...

3 years ago
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Club Night

I hadn't been at the club very long when he came over to me: a very handsome man, tall with dark hair and blue eyes."You have a perfect ass," he said.I was wearing a sexy, little minidress which barely covered my ass and I knew it would turn men on, but I didn't know it was going to happen this quickly.I smiled up at the tall stranger. "I'm flattered," I said."I'd like to pull up your dress and lick your ass," he said.It was a "clothing optional" club and I knew he would do it if I told him,...

3 years ago
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Luck ran out

Everybody runs out of luck!! There i was again wearing my G/F's bridesmaid dress with the 4 inch wedges, bra, thongs and stockings this time. While wearing this wonderful outfit i yet again decided to tie myself up while everyone was out of the house. but this time i put myself into a tight hogtie using cable ties, with a realise mechanism of sizzors. So there i was enjoying the feel of the satin against my body knowing every one should be out of the house for a good 3 hours, just fighting...

3 years ago
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Noodles Part 6

I was still recovering from the beautiful violence my body had just been through, at the hands...and cock, of my friend, Mark. Both the pain and pleasure of that experience, exceeded my assumption, or even my imagination. I had given my virginity to Mark, and he had given me the most intense orgasm I have ever known. 'Anal orgasms are a real thing,' I discovered.Although I experienced the feeling of ejaculation, I did not have a trace of it in my panties. And I didn't get hard, at any point in...

3 years ago
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Alexia s Tale Chapter 3 Sensual Outgoings

Sunlight beamed through the curtains, warming up the room. Under the sheets, a mildly aroused Alexia laid half asleep, one finger halfway up her ass and her mouth gently sucking on her other hand’s fingers. Her cock was slightly bulging, as it tried to break free from its fabric cage, causing it to pull on the thong. Her hair was messy, but in a way that you’d love to see after a good night’s rest. Her eyes opened, and Alexia realised what she was doing."Oh!“ she squealed, as she pulled her...

3 years ago
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A Night to Remember or to Forget

As a petite, pretty, and now fairly confident young transvestite, I feel fortunate to have discovered so many things about myself. I am proud to have a slim, smooth and well-exercised shape. I have longish streaked blonde hair and my goal is to always develop and improve my feminine elegance.My friends tell me I possess a very strong believability in my appearance as a young woman. I think it is due to the constant experimentation and hours of practice that I joyfully spend in front of my...

3 years ago
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The Cardboard Fort Part 2

That evening I thought about Gene and what had happened in their old fort. I finally had the opportunity to wear something besides the slip I  had shoplifted. I really enjoyed dressing up for his friend and what had happened as a result. I didn't feel weird or strange about it."Maybe I should have been born a girl." I mused before falling asleep.Two days later Gene appeared at my door with another paper bag. Inside was a pair of black silky nylons and a black silk and lace garter belt. Now I...

3 years ago
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The Pool Man

It had been several months since I moved away from the big city. It was hard moving to a city with not a lot of people I could hang out with or be with. I had become really good at dressing up and having anal sex, but was becoming more and more restless of not having a regular, daily thing with someone. I began fantasizing about being with the pool man. He was always friendly when he came over every Friday to clean the pool. He would always stop at my window since my room faced the street. I...

3 years ago
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Glimpses of Consequences

GLIMPSES OF CONSEQUENCESBy DrBill"HOWA we going to start?" The ritual joke having been followed by the ritual groans, the Housewives of Worthington Acres came to order. The group had evolved from informal visits for coffee and complaining to a neighborhood organization of sorts. While the meetings still tended to be primarily boast and bitch sessions, they also traded useful information and occasionally took on neighborhood improvement projects and the like. But they did not try to pretend that...

3 years ago
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Evie Gets Her Reward

I went downstairs to the kitchen, carrying the cold tea. As I walked into the kitchen, I could see up the drive through the window. There was a car parked at the top of the drive, a taxi. I ran back upstairs to Mistress Sarah. “Mistress, are you going out again?” I asked. “No dear,” she replied. “why do you ask?” “There is a taxi parked at the end of your drive. It looks like the same one as yesterday,” I said. Mistress Sarah smiled and said, “Evie dear, I’m not sure, but I’d guess it’s...

3 years ago
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Sissy Blane and The Trove of Vintage Porn

It must have been a week or so after Cindy’s big announcement when I got a phone call from Madam H’s assistant. She would like to see me at my earliest convenience. I thought it must be more pressure to bring up my arrears. I would have thought that Cindy had already taken care of that debt for me, but no matter I would be glad to tell her in person that she no longer had leverage to twist my arm. I brusquely told the woman that I’d be there in an hour and hung up.To go with my insouciant mood...

3 years ago
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First time

I was 17 when I had my first experience with another man. My sister was in her sophomore year at college and I in my senior year at high school. She was going to spring break in Florida and since me and her had always had a great relationship she invited me along with her and her friends. My sister was cute, blond hair and blue eyes. Very tan and athletic. She had that all American preppy girl style. We arrived in Florida on a Wednesday morning and spent the next few nights parting and having...

3 years ago
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OMG Last Night

I suppose I'd better start at the beginning. Well, my femme name is Carly Hughes.I'm a 47-year-old male who has probably been cross-dressing since he was seven. I started dressing in my mum's and sister's clothes. I've built up stashes of clothes many times and binned them through guilt. I've probably wasted so much cash it's unbelievable.Anyway, I've done all the manly things in my life like football, being a jack the lad, getting married, becoming a dad, etc. Through all the years my...

3 years ago
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We All Have Our Stories

I want to present a few short vignettes concerning crossdressing. A most interesting and individual form of sexual gratification and fulfillment. The first story concerns a strong man, happily married and happy with the sex he is getting from his wife, but something seems missing in his life. He often walks the streets and window shops, but seems to be drawn to the windows displaying ladies' wear, from dresses, to frilly underwear, to stylish shoes. He is drawn to it all. And he forms the...

3 years ago
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A Sister s Bet Parts Two and Three

Part Two - TrainingBy the end of the first week, I had almost mastered walking in heels and had gotten more adept at doing my makeup.Jessica continued to tease me. “How about it, bro? Do you want to give up yet? You could end this by admitting that being a girl is better.”“Hell no, I won’t give you that satisfaction.”“OK, but remember, you have another week of this to go.”“That’s difficult to forget.”“You know, I bet you secretly like this.”“Yeah, right.” I already realized that, but I wouldn’t...

3 years ago
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After the Show

I‘d met David through my (now ex) wife. He lived in the Twin Cities with his partner Dennis. His being gay made it very easy for me to talk openly about being Samantha. He hosted a drag show on Saturday nights at a small gay bar so he’d invited me to come along, meet the ‘girls’ and see the show. I could stay the night so I could go dressed and have a fun ‘girl’s night out’ while he MC’d the show. I got dressed at David’s before we left for the show while David waited and changed at the bar. I...

3 years ago
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Jason and Kym Part Two

 Later that same night, I strolled down to my favorite watering hole to tip a few strong drinks in the hopes of either clearing my head or dulling the noises within. After flirting over those drinks with a short blonde haired gal named Kym, we stepped out onto the dance floor to press our bodies against one another to an old Jonny Cash tune. She’d been waiting for some guy to meet her for a drink; for whatever reason, he’d chosen not to show. His mistake was my gain. I felt her hard nipples...

3 years ago
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Candy Land

- Hard Candy -A blue raspberry sucker crunched between my teeth as I descended the deserted parking garage. The click of my heels echoed through each level as I minced my way to the busy street below. A cool summer breeze blew up my mini skirt tickling my ass. The pink thong panties Master picked barely contained my swollen balls and the pink cock cage that imprisoned my clitty.I tried to appear confident and natural but I was terrified someone might clock me for what I am. My makeup was...

3 years ago
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My first time with a man

I had been into dressing in kinky little latex skirts and dresses for years. I loved the way they felt against my skin. Playing on my own had been enough until now, I had toys and vidoes to amuse me but the thrill of being fondled and fucked by a real guy was now too much to resist. I decided to try the online sex sites to find someone and find someone I did. He had looked at the pictures I had placed on the site and was bursting to get his hands on me, a thought that made me tingle with...

3 years ago
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48 Hours Chapter 2

Chapter 2: Let's Make UpLynn walked into the bedroom and threw the bags down on the bed, a white lacy suspender belt falling out from one of them."Wow," smiled Chris, "you weren't kidding about the weekend.""I certainly wasn't. Now lose the dressing gown and turn around. Shut your eyes too, keep them shut until I say otherwise, and remember, no more questions."Chris did as he was told. He really wished he could watch her undress and put on that new lingerie.He heard her pull off her dress and...

3 years ago
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Caught and punished by my manager part 2

I lay there on the floor, my g-string still dangling around my ankles, my vibrator rammed deep inside my ass. My boss Mei had been gone all morning, leaving me vulnerable and exposed in my lace garter chemise set, sheer stockings and high heels. I lay there staring at myself in one of the mirrors. I felt so feminine and slutty as I wriggled my bum against the floor and rubbed my legs together. I wanted so badly to feel like a girl and now I was trapped as one. The hours went by quickly as I...

3 years ago
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Hot Fuzz

If you have read my profile you would know that I am married with three kids, and no privacy. That being said, I try to indulge in my favorite pastime of cross dressing whenever and wherever I can. I was working as a manager for a convenience store where I would have to get up early in the morning to open the store. It was a 24 hour store, so I just had to get there to send the graveyard person home and do paperwork. One morning, I got up a little earlier than usual, and since the wife was...

3 years ago
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Hidden in Plain Sight

It was his own fault. He had spent far too long admiring himself in the mirror and revelling at the sight of the erotic garments he had donned and time had slipped away from him. Just the feeling of these silky garments against his skin made him hard as they always did and a masturbation session would soon follow.The mirror on one side of his sliding closet doors reflected the image of a tall and tanned young man with long dark hair and slightly feminine features. If he had been born a girl,...

3 years ago
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Memoirs of a Crossdresser Chapter 1

My True Story Chapter 1: I was a kid when I first discovered women's underwear. I loved the way it made me feel. I had a friend who I'd play the normal games that kids play with, and I would always be the girl character. We were children, so nothing out of line went on, but even at a very young age, I had felt an attraction to femininity. There was something that made me feel like I should be the damsel in distress, waiting to be rescued. I remember wanting to feel girly. As I got older, my...

3 years ago
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Family Support

from the title u may think more than what it actually is i only have one family person who knows my cousin who is a lesbian she phones me up anytime she is alone for me to come and dress in her things.  Any way to my story my cousin had phoned me up one day and told me to come over it was only a five minute walk and i was so excited.  when  i arrived she told me to go up to her room and once i was finished (dressed) i had to come down because she had a surprise  for me i took my time getting...

3 years ago
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Night Out Ch 2 Good Morning

The chill of the morning brushed against her cheek; Evy began to stir despite the wild night before. Her stomach began to whisper its hunger; the need to use the bathroom tickled at the back of her mind. The warmth and coziness from being in bed made her not want to leave until she found herself searching more for its source.Rolling over, Evy reached until her hands made contact with skin: a body. The flashbacks from the night crashed into focus as the grogginess and sleep began to leave her....

3 years ago
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Vanessa Goes All the Way

A few months after having my first date, I was feeling kind of anxious about not really allowing myself to go further. I had plenty of guys interested, but I wasn't really ready to make that move. I had been talking to this sexy college boy for a few weeks, but we couldn't set up anything solid. We finally nailed down a date, but he had some last minute issue come up, and had to cancel. I had enough. I wanted to experience the full act of being a woman, and I wanted it that night! I went...

3 years ago
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Beginnings at the Adult Book Store

There are two types of cross-dressers. The first are those who dress all the time. They are usually quite passable since they spend a great deal of time and effort. The second are wannabe women who live in a world where there are circumstances that prevent them from being full-time out of the closet cross-dressers. They are usually not passable since they cannot shave their entire bodies, grow and style their hair, purchase and maintain a female wardrobe, and/or learn and understand make-up. I...

3 years ago
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The Change Up

Finally a break comes my way. The children are off to college, the wife has to go out of the country for two months on business. I can’t remember the last time we had sex. She used to dress in all types of lingerie for me. It helped me suppress some of my crossdressing desires. That stopped and my crossdressing started to grow again. What an opportunity for me, I can change up and dress the entire time except for when I have to go to the office. Lucky me, most times I work from home. Sunday, my...

3 years ago
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Teenage CD Awakening Part I

As a child I lived in a town in the North of England. It was a fairly conservative place, where boys were expected to grow up to be men, and girls to become women. Despite this my mother was a fairly liberal person, and by the time I’d reached the age of 17 the topic of sex had already been raised in our house. Sex between men and women of course, with the aim or perhaps the danger of making babies! This was in 1979. Although my skinny body was still hairless my interest in sex and my desire to...

3 years ago
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Vanessa and Ken s Second Date

It had been a couple of weeks since Ellie and had our little trysts with Derek and Ken, and I couldn't stop thinking about it.  As much as I loved being with Ellie, there was something magical about that night with Ken.  We had talked about it, and I downplayed how wonderful it was to make love to Ken.  She told me that she enjoyed her night with Derek too, but she didn't really seem to make a big deal about it.  I wondered if she was downplaying it too, but part of me didn't even care.  Maybe...

3 years ago
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Across The Street The Conclusion

Mike left his telescope at the window even though it wasn't used any longer; his laptop was the new tool of choice. Every night around midnight he would receive a chat request and a second later Leann's beautiful face would fill his screen. There was the usual small talk about their day as Mike stared at her pretty face.They didn't have to talk about sex. Between her looks, dress and voice Mike always got hard. Leann seemed to be able to sense when he was ready and would start her music and...

3 years ago
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Little Black Dress

I pulled in the driveway, and saw that my wife was already home. My thought was that she’s home early. I unlocked the door and went in. A few feet inside the door was my work stool with a box on it with a note taped to the top. I opened it and started to read. Hun, I’ve decided that tonight is the night I want to collect on our bet. You are to follow the instructions that I am going to give you.  I promise that this will be fun for you too. Go up the back...

3 years ago
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The Young Crossdresser Part 2

So after my little adventure at mom and dad's bookstore,the next couple of years were uneventful. I did have sex a couple of times with Phylis,the older lady that was part of mom and dad's swinger group. I knew that I was wanting something more,something was still missing and I kept thinking back to how the guy's cock felt as it spewed cum into my panty covered ass. Now I was 15 and one weekend my parents went away with some friends and I knew that this would be the perfect oppurtunity to...

3 years ago
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Jack Has A Secret

“When is he due back?”“Who?”Audrey gave Jill a look. “Oh, you mean Jack? Not sure actually.”“I call that bullshit. You know exactly when he will be back.”Jill smiled dreamily . “Yeah, tomorrow at 8.15pm.”“And by 9.30pm you will have his cock deep inside you?”“Hopefully.”“How long has he been gone?”“Three months almost, hiking in South America with his other macho friends.”Audrey thought about her friend’s fuck buddy. Jack was such a man’s man. Tall, broad shoulders, square jaw and thick dark...

3 years ago
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Adventures in a Woman s Body Chapter 4 Public Humiliation

I stepped out of the shower and began to dry myself with a towel. On this bright Monday morning, all I could think about was what happened on Friday night. After being gangbanged and cumed on thoroughly, Daddy drove me home that night. On our way there, he explained to me the situation that I am in. Daddy took out his phone and showed me pictures he had taken of me being a dirty little whore. He said that from now on, he will truly be my Daddy and that I must do what he tells me to. Otherwise,...

3 years ago
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Second Encounter Ch5

We enter the bathroom giggling like school girls. Taking out our makeup bags, we commence to do our faces. We remove the light make we applied that morning and scrub our faces clean. Like sisters, we help each other to get just the right look, making suggestions and comparing techniques."I've got something new I'd like to try," you say."What's that?" I ask."False eyelashes," you answer."I want some, too," I exclaim excitedly."This is a three-pack," you say as you pull the package out of your...

3 years ago
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The Ultimate Fantasy

Paul couldn’t walk fast enough. His heart was pounding and he kept checking the time on his iPhone every couple of minutes. It was only a ten minute walk to the hotel but it seemed to Paul that he would never get there. He knew that Marie has something very special planned for him and he couldn’t wait to find out! The day started normally enough. Paul was up before anyone else in the house and had left at his usual time, just after 8am, to catch the bus for work. The day had been busy but not...

3 years ago
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The Wedding Proposal chapter II

The large gown rustled, and the heels clicked loudly as I descended the stairs in my home and walked towards the front door. I would be picked up by my friend’s sister before going to the church. I had never met her before, but he’d assured me that she knew nothing of my secret. It would be nice to have someone to confide in, but I knew being treated as a girl by everyone would probably make this feel more natural in the end. My friend had arranged everything to make this day as painful as...

3 years ago
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Dirty Little Me

Rushing around all day, it seemed like this was starting become a ritual for my Fridays but this particular Friday I would never forget!  Waking up late as usual I flew out the the door as fast as I could, not giving any thought to what I had done the night before. As usual my boss wasn't too pleased but I never really minded his attitude because everything he lacked in personality he made up for in looks. Luckily the dirty thoughts I had of dressing up like a sissy little girl for him kept my...

3 years ago
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Not What You Think I Am

Marriage can be a lonely place, two folks living together and yet being so far apart. It never used to be like that but I guess it comes with the ageing process; a mid-life crisis. To overcome our frustrations, my wife decided we would spend more time together away from our comfortable home, so one weekend every month we hire a log cabin at a campsite that sits between the forest and the lake. It might have been better to spend weekends apart and, realistically, that is exactly what we do!...

3 years ago
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Hitch hiking Baby Doll Part Two

I woke my trucker stud up in the middle of the night by sucking on his cock and making it hard for him. When I had him good and hard, I climbed back up between his legs and let him put it in me again. His cock was nice and big and my ass was good and tight. It felt good to feel like a girl receiving anal from her big Daddy. While we lay on our sides in his bunk and fucked, my trucker stud reached around me and played with my dickie. He was sweet to be thinking about pleasing me while I pleased...

3 years ago
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Karren Gets Sucked and Fucked Part 2

Karren followed Kevin to his home in her own car so if she had to leave she could do so at her leisure. Karren wondered what Kevin's wife looked like, would she like the idea of a man dressed like a woman making love to her? Would she like sharing Kevin's cock with another man dressed as a woman? She hoped everything would turn out for the best.  Her thoughts were arousing her cock; she could feel the panties and slip caressing her cock. As she drove the car and moved her legs to shift the...

3 years ago
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Becky s Video

I suppose I was the one that first mentioned porn to Nikki. We'd been chatting on a girls' night out and laughed abut how I'd never found any porn in the house. She giggled and said I was bound to find some sooner or later – all men had some, somewhere. A few days later, I'd completely forgotten our drunken conversation and so when Nikki showed up at mine after you'd gone out with your friends, I was surprised when she mentioned it. We'd both had a few glasses of wine at that point and when...

3 years ago
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She wears the pants over her cock

I stepped off the plane after three days travelling and was looking forward to going home after a long few weeks of travelling for work. My work regularly has me travelling and I don’t seem to get home as much as I would like anymore.   But it does make it even more enjoyable when I do get home.   Leaving the gate, I walked down the corridor, past the last security checkpoint, and toward the baggage claim area.   I don’t typically check bags, but with the new charges that all the airlines...

3 years ago
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Jamie s Gradual Grooming Part 2

"What would you do if I put some girlie clothes on?" What a stupid question. The moment seemed to last for an hour but it could only have been a few seconds. Mike looked at me, again with an indifferent look. What would he say back? Would he say anything at all? He glanced down at the chopping board and then back at me. "Could you pass me the onions from the fridge please?" he said. Nothing, no response, very cold and Mike became a stranger to me for that brief moment. I wasn't expecting that...

3 years ago
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Getting A Grip On The Situation Part 3

Ken was sent home in plenty of time so Vanessa could become Van again. Van thought about the morning events as he stepped in the shower to remove his makeup and continued thinking when he returned to his room and carefully hid Vanessa's clothing and makeup. This long and laborious process was necessary as discovery by his parents would be disastrous for him.Still wrapped in a towel he then collected all of Vanessa's semen-stained lingerie and hid them in the basement, he would wash them when...

3 years ago
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Sissy at the Bookstore

I had gone to adult bookstores for many years and had done it in drag many times but never dressed as a sissy and never during the day. On this day I was so involved in humiliating myself that I decided that I need to take that extra step and I did.I had checked into an adult motel the night before and booked for two days so I had a lot of time on my hands. The night before I had pranced around in front of other guests, both men and women, dressed in sexy women's clothing and had a wonderful...

3 years ago
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Jessie s Fantasy Chapter 6 Turning the Tables

I was floored by what Tracy had said to me. “Because, the male Jesse is no more for the time being, it is womanly Jessie that needs to go.” It seemed that my love just told me that I had to meet up with my male friends tonight. My mind was going a mile a minute. I already fooled my friends once. But can I do it again? If I do, what is going to happen? What will I let happen? My stomach felt like butterflies. I was getting a little nervous. “Are you saying that you want me to dress up and meet...

3 years ago
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Big Green

Loosely based on true events and it is my first story so please be easy. Being a Marine for most meant traveling, working out and above all alpha males only. For me all of this was of interest but I didn't work out and I was definitely not an "Alpha Male". Slim in stature I stood all of five foot, six inches weighing in at a whopping 145 pounds. I wasn't much to look at in a uniform but out of one was another story, I could dress with the best and I looked good doing it, that was the best part....

3 years ago
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How Andrew became Andrea Part 3

Andrew leaned back on the couch feeling the warm cum had just let loose in his panties beginning to cool and a stain become visible on his slip. "Looks like you will have to clean up and change," Lacy said with a smile. "Looks like," Andy responded. "Shall I pick out something or would you like to?" "I would like you to." Andy headed to the bathroom where he removed his cum soaked, stained lingerie and then cleaned himself. Lacy knocked on the door and handed him one of the most stunning...

3 years ago
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Crossroads Ch 3

A tale of pure fiction and fantasy. I was actually considering going all the way. Going all the way in becoming female. I had been living as a female in all phases of my life for some time. I continued on the hormones and all my desires said I should do this. I had called the plastic surgeon who had done my breasts and explained what I wanted. She suggested going to see a doctor in Vancouver who was an expert in SRS. I called his office and made an appointment. Luckily he could see me on...

3 years ago
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Bachelor Turns Bachelorette Slut

I was ass naked on my knees in a cleaning closet, my tuxedo in a pile on the floor, my long hair pulled high on my head into a girly ponytail, and my fat lips wrapped around my best man’s juicy cock. As I moaned and whimpered and slurped on his throbbing pole, he pulled on my ponytail. That sent electric shocks cascading down my scalp throughout my body, over my sensitive nipples and fluttering abdomen to my rock hard cock.Both of my small hands were slick with my saliva as I stroked his dick...

3 years ago
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My New Life As A TGurl Slut Pt 4 DP d By The Bouncers

Jack was the first person I met on my first night out dressed as a girl... a sexy, slutty girl.He is the head bouncer/ co-owner of the security firm that deals with security for various gay and tranny nightclubs including this particular TS/ TV/ CD club which was my first introduction to 'the scene'.And I must say it's an awesome club. The trans scene is much larger than I realised but this isn't just a venue that hosts transgender nights, it offers much more.It certainly isn't a sex club...

3 years ago
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My Girly Fantasy

I wake up and smile, remembering where I am and who I'm with. I'm warm and comfortable, wrapped in your arms as you sleep. I think back to last night, finally showing you my girly side. We've been best friends for ages but I always had a crush on you. Finally, drunk on wine, I decided to do something about it. I came into the living room we share and straddled you; taking off my robe to reveal my soft, smooth and feminine body. Giving myself to you like a present all wrapped up in lingerie. I'm...

3 years ago
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Felix becomes Felicity Chaopter 3

FELIX  becomes FELICITY Chapter 3 ..He bent forward and thrust his large hands up my skirt on my thighs with his thumbs resting on the root of my penis, and put his face close to mine, “You had better be a good girl for everyone’s sakes sweetness. I know you love your Mum and Sister!” He slowly moved his hands up to my breasts and squeezed them hard looking into my eyes. I was speechless. “Yes I have a soft spot for sexy little girls like you.” With that he pulled away and walked into the...

3 years ago
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Seducer or Seducee

Every year a city about an hour away from where I live hosts a big charity costume party that coincides with Mardi Gras. I had decided to attend the event as my female persona, Tessa. Since I don’t get many chances to go out in public I decided I was gong to go all out for this event. For the last two months I had been on a strict diet, more like starvation but I knew the results were going to help me with my transformation. I lost fifteen pounds and some muscle mass too. I had limited my...

3 years ago
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Georgina s First Steps

Mary and Linda met at primary school, became best friends, and supported each other as they grew to womanhood. Both married at twenty. Mary's daughter Julie was born a year later, and I followed within a few months. For both of us, the first few years were a blissful blur of happy families. Sadly, this idyll changed when Julie’s Dad, soon to be followed by my own, succumbed to the wanderlust, and sought out pastures or at least lady gardens new. Life was now hard for the single mums, but they...

3 years ago
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She Made Me Do It

Something inside me just grabbed hold of my male shackles and snapped them in two; discarding them into the depths of depravity. I had been writing stories about crossdressing and transsexuals all week. I had been looking at girly pictures, not the feminine girl ones, the ones that had dicks. Some of them were absolutely gorgeous, far better looking than some women and I wanted to be one of them. I really did. I particularly loved the ones with the pink underwear and black bows. I have a few of...

3 years ago
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Curious No More

I began dressing in my sister's clothes. I would get so hard and excited when I felt the soft panties against my cock and the bra wrapped tightly around me. But my dress up time was always short. Now that I live on my own I have my own femme wardrobe and plenty of time to dress and perfect my makeup and appearance. The more I dressed and the longer I stayed dressed, the more I wondered what it would be like to be held closely by a man and feel his warm embrace. Soon I began to wonder what it...

3 years ago
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Weekend Discovery 2

Simone's eyes grew wide when she realized that the stunning blond she was sitting next to was, in reality, her boss and the object of her most intimate desires. Now she had seen transvestites and drag queens before, but none of them looked this good. She was sitting just mere inches away from his face and still couldn't see any trace of Andrew Lippincott. Without warning Andrea leaned forward and gently placed her lips on Simone .When their lips touched a bolt of pure desire shot through...

3 years ago
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Confessions of a Sex Crazy Cross Dresser Part 8

Chapter 15: Dangerous Duo I woke up the following morning to an empty bed. I went to the bathroom and when I came out there was a knock on the door. I looked out and saw Peggy with a bag and two cups in her hands. Upon opening the door, Peggy came inside and placed the drinks and bag on the table and gave me a kiss. “I thought you might want some breakfast,” she said. She had on a pair of white shorts, a light blue tank top and her sneakers. “I brought coffee and donuts.” This girl might be a...

3 years ago
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Surrendering to Temptation 3

Grant returned to his room on rubbery legs due to his recent masturbation session. Clad in his sister's nightie, panties, and pantyhose while he masturbated gave him the most intense orgasm that he had ever experienced up to that time. He thought about the nightgown that he had worn, washed, and hidden in the basement and decided not to return it to his sister's room.Since his sister admitted that she no longer wore them, he was sure that it wouldn't be missed. He would recover it and hide it...

3 years ago
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indian crossdresser

hiiiiiiiiii every one here's kiran from india ,punjab first of all its not a fictitous story ,it is  a real part of my life my actual name is rahul and me a guy now of 20 yrs old. so lets start frm my age of 12 yrs............................... me frm starting was very likely to kiddish me always remain at home .not to go any where else than in my street. in mid of june when our holidays were going on my parents were with at home ,i asked them about there relationship .they bit were not happy...

3 years ago
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My Story

 This is my story in a short form of how I became me a 22 year old black gay crossdresser. I've always had gay tendasies from as long as I can remember but at age 17 I met a guy who house I use to walk by after school and we would chat, after a while I told him about me and he said he always thought I would make a cute girl, now he was white and a bit older than me at 30. After a couple weeks he talked me into comming in his place said he had a present for me, well what it was several girl...

3 years ago
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my first date with Ben

I had been chatting with Ben online for a while and we had talked on the phone several times before I decided to meet with him. I had met him through Craigslist so he knew what I was all about from my ad. We arranged to meet at restaurant for an early dinner so there would be plenty of people around. That Saturday, I spent my time getting ready. I showered and shaved smooth and used a nice lotion to make my skin super smooth. I took my time doing my make-up and went with a conservative look...

3 years ago
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Crossroads Ch 02

The second chapter in this crazy little tale. I really loved my little adventure out as a woman. I liked the power I had over men. I was seriously thinking that I would like to live as a woman full time. That would be quite a commitment and one that would change my life forever. As I said before I worked for a really liberal company and one day I got up some courage and went to my boss. I explained to her my desire to live in public as a woman. She smiled and was very understanding and said...

3 years ago
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The Long Walk

Friday. I get home from work around 9:30, and I head straight for the shower. Now most stories like this involve shaving smooth and things like that, but I'm not able to shave because my wife doesn't care for it. After my shower I go into my closet and get my clothing. I get my black bra and thong and slip into those, followed by tan hose and regular clothes. I have the rental company pick me up and then its off to the mall for some window shopping and looking at heels. Being unsuccessful at...

3 years ago
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A Night of Firsts

I have been crossdressing in private since I was young. Now in my late forties and after three failed marriages, I had decided to step outside as Jessica.So after a lot of planning over several months, the day had finally come.I stepped in the bath as JD and shaved any hairs on my body that should not be there. It did not take long as I had been preparing my body for weeks to be smooth. I stepped out of the bath as Jessica and dried myself off. I wrapped the towel around myself just like any...

3 years ago
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Satin lingerie

My sexy pink satin panties felt so good against my skin and looked great with black stockings and garter belt, my matching satin camisole top was so soft and I was gently creasing my pert nipples through the fabric. It was around 10pm and I was feeling a little bit tipsy after my bottle of wine The DVD was playing Cock in Frock and had some sexy clad shemales in compromising positions, god I love my nights in. I have always loved dressing like a slut and have now shaved all my...

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