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Crossdressing

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16

Erica Loves It (Part 1)

Erica discovers sex

For my entire life, I've always thought it was so unfair that girls gotto wear all the really cool clothes. They were softer material, better color choices, and looked so much better. In fact, when I was very young I wore dresses whenever I got to play with the girl next door, but that was always for the tea parties and such we liked to have. But by the time I discovered sex and masturbation...Read On

16

First Love

Crossdressers first love

This is the story of the first time my first boyfriend and I fucked. Before I get started I should give you some background information about myself. I had always considered myself straight and had been happily married for fifteen years before my wife and I drifted apart and divorced. While we were married I had wondered what wearing some of her heels would be like. Unfortunately my feet were...Read On

16

Seducer or Seducee?

Male attends a costume party as Tessa and is seduced by a beautiful woman.

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...Read On

16

My first time in a bar

The first time I met a guy in a public bar for a drink

For a while now I had been chatting with a sweet guy named Allen, who was bisexual and was eager to meet a crossdresser. He was very muscular and handsome, a hard body but with friendly eyes. He seemed to really like my pictures and said he had cum, stroking himself, while looking at them several times, and was eager to meet me in person. He wanted to meet in a bar which is something I had...Read On

58

The Change Up

Sexy outfit gets Deedra some lucky action

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...Read On

49

Neighbor fun

Slutty fun with neighbors

It was a typical Friday night. I would hurry home from work to complete my ritual. Take all of the necessary steps for a lot of anal sex, shave all over and transition from a male to a female. I put on a typical “uniform” for the trip to his house. A lacy black top with a lacy black bra under (looked more like a teddy than a top), a short pleated black skirt, black stocking, garter, and...Read On

46

A Taste of my Girlfriend's Dildo

I'm caught - and made to love it.

I can’t think of anything I’d rather be doing than sneaking into my girlfriend’s wardrobe while she’s out and trying on her lingerie. The moment she leaves the house, I head for her garter belts, bras and knickers. I don’t have anything to put into her 36C bra cups, and my cock barely fits her panties but all that silk, satin and lace is irresistibly sissy and feminine. On the day...Read On

15

The Feminisation of Michael. - Chapter 4

The Feminisation of Michael. Chapter 4 Sue had replenished my wardrobe again with new work clothes and had taken the secretary theme to heart! The skirt suits had been replaced with pencil skirts and pencil dresses. The blouses had been supplemented further with lace and ruffle fronted blouses. There were also several ribbed tight fitting cardigans in black, red and various...Read On

15

Bookstore Bunny Gang Bang

Dressing as a Playboy bunny at the bookstore lands Courtney four big cocks.

Dressing as a sexy girl is my favorite way to meet men and have fun. There are so many different sexy outfits a girl can wear to attract men and turn them on, they ensure it never gets boring for a man. Every girl wants to be her sexiest when wearing lingerie and I am no different. Recently, I was on a business trip which included spending the night in a motel located across the street from...Read On

14

Christina and Cheryl

Girlfriend makes me cross dress and fulfill her fantasies.

Christina and I had been dating for nearly two years. Within six months into our relationship, I confessed that I enjoyed dressing in women's clothing. She'd been more than accepting and encouraged me to indulge in this. She'd bought me bras, made me wear panties, painted my nails, and given me make overs. Seeing how horny it would make me turned her on even more so. I knew Christina was bi...Read On

14

From Anton to Antonia

Anton discovers a feminine side to his sexuality

The first sex I had with a couple was my boss and some woman we just met in a hotel bar. I liked it, so the boss told me to put out an ad. An advert in Craigslist for my area was all it took. Posted in the casual section under M4WM and a photo of me from the shoulder down, I had a flood of answers. I chose Julian and Rosemary, they were mid- thirties, still twice my age and arranged to...Read On

14

Sissy Slut Gets All His Holes Filled

Desperate sissy slut boy gets what he wants.

He was waiting for me as instructed, dressed in the bag of clothes I had left for him earlier in the week. I entered the motel room to find him sitting on the bed in the mini skirt, sheer blouse, lace topped thigh high stockings and stiletto heels from his goodie bag. With his legs crossed, he appeared to be quite demure but I knew the desperate, horny slut that was raging beneath the...Read On

14

576 Shadow Oak Drive - Part 2

Sarah and Molly arrive at the party and Sarah has another first experience.

As Molly drove down the highway, I sat in the passenger seat. Although I had always had a feminine side, I was experiencing all kinds of new emotions and feelings that I hadn't felt before when dressed. I don't know exactly what brought it out. Maybe it was the love and support of Molly. Maybe it was seeing myself truly dolled-up for the first time, seeing my own cleavage, having my manhood...Read On

14

And It Begins

I make my first real steps into the real world.

There seems to be a common belief, if you want to call it that, that there are basically three “levels” of Crossdressers or Crossdressing. The first of these is what is referred to as fetish dressing. These people have no intention of doing anything other than wearing items of feminine attire. They have no desire to even attempt to emulate the female persona. This is purely a very temporary...Read On

14

Unexpected Turn of Events

Jessica meets a neighbour at a bar

I sat in my favourite bar sipping at my glass of Chardonnay; I had been coming to ‘The R Lounge’ for a couple of years. I watched the guy talking to his friends across the room. They were all dressed with a bit if style but he had caught my attention. He was wearing trousers with a casual blue and black stripped shirt. He was probably five feet nine inches tall. He had an average build; not...Read On

28

My first halloween night as a teen CD!

My first time i dressed up like a chick and how lucky i got that whole night

This is halloween!! A day that everyone goes out and dresses up in costumes and other things, and go to parties and drink and show off their wild side until the wee hours of the next day. And I thought to myself, since everyone goes out and wears costumes, why not dress up myself into something wild and willy?? Or in fact, why not dress up in a manner of expressing who I am and what I...Read On

28

Tickets please!

My life changed forever on the 07:28 from Bristol

Standing by the window, I watched as the countryside flashed by. My train had been delayed due to a dodgy signal just outside the station, but judging by the speed the driver was maintaining there shouldn't be much of a delay, thank goodness. Even though I hated my job and boss I needed the money desperately. With a sigh, I turned away from the dreary grey outside and tried to make...Read On

28

A surprise helping hand

Getting caught paid off, in more ways than one

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...Read On

27

Dan a.k.a. Becca

Dan discovers his feminine side

Dan had been fascinated with women’s panties since he had found a pair belonging to his sister accidentally mixed in with his clothing. He had rubbed them against his face feeling the silky smoothness. He kept them for a few days until he heard his sister asking about them, then made a pretense of finding them stuck in between the washer and dryer. After that, whenever he had the chance, he...Read On

26

The Feminization of Michael - Chapter 1

The Feminization of Michael. Chapter 1 How I had found myself in this predicament Ill never fully understand. Ok I guess it was my own fault but why I didn’t kick against it when I could Ill never know. I had been involved in a sordid night of drink drugs and sex with a young transsexual hooker! Including her/him putting a bra and panties on me! I didn’t know any of this until my...Read On

26

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...Read On

26

Seduction of Piper

Stephanie give's Piper intimate assistance trying on lingerie.

I want to thank Farmgal who's sexiness inspired this erotic and steamy tale. Thank you Farmgal, I enjoyed writing my sexy fantasy of seducing you. Stephanie was attending the check out register at Victoria’s Secrete when an extremely sexy woman strolled into the store. Stephanie’s heart beat faster and her eyes locked on this sexy woman as she sauntered towards the display of the new line...Read On

13

Night on the Town

The girls and I go out to a lesbian bar.

Night on the Town Barbara Marsh “Well, come on, chicken!” I responded, “Cluck, cluck.” Okay, so I know it’s not original, but it was the best I could do. Despite my misgivings, I got out of the minivan, smoothed my skirt across my hips, and waited for Alexis. Her name’s really Alice, but she was Alexis for the night. The same way Jeanna was Gina and I was Betinna. I don’t...Read On

13

Erica Meets Sarah: Part 1

Slutty CD Erica meets Sarah to fulfill her ultimate fantasy for the first time.

I woke up alone on Saturday morning in my nylon blue g-string and nothing more. I wanted to feel it the instant I woke up, my sexually charged femininity, I wanted to feel it all day. Today I'm not a man, today I'm the girl every man wants. Today I'm a slut, your slut. I showered and shaved myself smooth. Ridding myself of body hair was always the first step. Nothing could make me feel...Read On

13

Taking That First Step. A new chapter begins

Cassandra introduces a new pleasure.

The Summer was drawing to a close, and Lance would soon return to school for his senior year. As excited as he was about his final year, he was saddened that meant no more early morning rendezvous with the stunning Cassandra. It had been a great Summer. Thanks to her assistance Lance had taken his desire to crossdress to a whole new level and he became Lana. In order to complete his...Read On

12

The Secretary - Part 1

I receive an interesting job offer

A lot of my stories are based upon the more formative years of my sexuality. Things are much less complicated these days. There's less sneaking around as I am not quite so in the closet any more, as well as the fact I live alone in my own apartment. I divide my time quite evenly between my identities although work is somewhere I still don't bring my cross dressing. Sometimes I feel like a...Read On

12

Jessie and the Office Girls

Jessie gets seduced by her office fantasy.

I spent the weekend trying to recover from the pounding that I received from Dan, Aaron, and Zach. I was their slave, and I had enjoyed it immensely. What I didn’t plan on was having all of my moans, groans, and enjoyment being filmed from twelve different angles, along with Dan telling me that he was going to share this video with our office mates. I was worried, yet anticipating what...Read On

12

Discovery

Kyle is discovered indulging in his secret passion.

Discovery, one of the greatest fears he has. All others take a backseat to his fear of being discovered indulging in his passion. You see Kyle is a cross dresser. Like so may others he doesn't know where this desire to dress up came from, but soon it was too strong to ignore. He started out with pilfering a few items from his sister's room and wearing them behind closed doors when the house...Read On

12

Exploring Even Further

Shauna meets Jerry's wife and things get heated.

For the rest of the week I was a total wreck, dreading, craving, anticipating, and fearing, the arrival of Jerry’s wife and Rocketman69, whose real name I'd discovered was Jim. Just thinking about all of the possibilities had me literally trembling with lust and, at times, fear. Jerry, too, was in a constant state of arousal. Neither of us could believe what a slut I was becoming. After work...Read On

37

Carlos and The Garter Belt

Carlos finally takes the plunge

Carlos sat in the car for a moment looking up at the sign of the sex shop. He had been in the shop on more than one occasion. A lubricant here and a toy there, to spice up the bedroom with the wife. This trip was not for that purpose. Every time he was in the shop, he was drawn to the lingerie section. In the past, when the sales girl would approach, he would say he was just looking...Read On