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My First Boyfriend - Part One

I learn to cross dress and get a boyfriend

Since my family had moved to our new house, Steve and I had become best friends. He lived next door and had moved in about a month before we did. With both of us being the new kids on the block we bonded quickly. He was two years older than me at eighteen and I had just turned sixteen a few months back. He was also taller and had more muscles than I did. He had tan skin and black hair where I...Read On


Uncle Joe

A surprise gift leads to unforseen pleasure

I had just returned from a long solitary afternoon walk in the forest. The house looked really pretty in the snow, with its fairy lights adorning the rafters and windows. In fact, it was quite picture perfect, so I stopped to take a photo. I framed the house against the white valley in the background, making sure that I included the lush green fir tree to the right of the house and avoided...Read On


TV Repair Man

DISCLAIMER: Story is merely fantasy and completely fictional. So please do not believe this happened to me or ask me questions about it, thinking it is true. I am writing from the first person perspective simply because it is a fantasy and it’s just more fun that way;) About a month ago my TV broke and it is kinda big and expensive, so I decided to have it fixed rather than buy a new one....Read On


Carl, Carla and Hannah - Part 1

Carl gets pegged by his girlfriend

It's funny the places life leads you to. Sometimes you think you know where you want to go, be who you want to be, and then from nowhere something or someone comes along and knocks you way off course. For example, if you'd have told me a year ago that on my wedding night I'd be on my knees being spit-roasted by two guys while dressed in my wife's wedding dress, I'd have said you were crazy....Read On


My Unexpected First Time With a Man

How a night of anal play, and crossdressing turned out to be my most intense sexual experience ever!

In the Arizona heat... It was Friday, the first day that I would be alone at home while my wife was on her trip. It was also the day that I timed a delivery of some clothing and accessories for a weekend of crossdessing and anal play. As I sat at work repeatedly checking the status of two shipments, one was a box of dildo's, lube and anal plugs, and the other was filled with lingerie, a wig,...Read On


Jessie's Fantasy: Chapter 1 Losing a Bet

Jesse makes a bet that he couldn't lose. Or could he?

Nearly everyone has a sexual fantasy that they would love to act on sometime in their life. Unfortunately for some, it never becomes reality. There are many different reasons, ranging from having fear or hesitation, to fantasizing about someone they can’t have, or the situation just never presents itself. This is a story of one such fantasy. Hope you enjoy! It was a Friday evening and I was...Read On


Chrissy Gets Bolder Meeting Todd Again

Chrissy gets a good hard fucking by her new friend

I really hadn't expected Todd to call me after that night. I know how guys are when the night is getting short and you need someone to satisfy your needs. I did think about him a few times and wanted to see him again. I had enjoyed my first experience with a man so much it seemed that's all I could think about was my next cock. When I went to class I would catch myself looking at guys as...Read On


A Terrific Threesome: Part One

Wearing my girlfriend's panties leads to a big cock for both of us. .

When my girlfriend and I moved into our new apartment, the tall handsome maintenance man came by to put a hand-held spray-jet nozzle on our shower for us. I was home alone and dressed in a sexy little pair of Sherry's panties when he arrived and I put on her little short black silk robe to answer the door. When I opened the door, the maintenance man's eyes went directly down to my...Read On


My First Boyfriend Part Two

My boyfriend and I get closer

NOTE- this story will make more sense if you read part one,it can be accessed through my profile page. The week leading up to today had been one of the longest of my life. I was very excited that today had finally arrived. My boyfriend Steve’s parents left early that morning and would not be back for three days. My parents had agreed to let me stay over while they were gone. Steve and I...Read On

Mistress Hannah's Pathetic Husband Part 3

I learn how manly my mistress wife can be

The first week of having a useful cock went well. For the first time since we got married, we had sex every night. After strapping my extension on, I would lick Hannah's pussy enough to get her turned on and then she'd choose a position. If I got physically worn out, she would choose another position. Because I was having sex so often and doing some research on the Internet, I was able to...Read On


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


Becoming Chloe - Part 9

Vickie has an 'episode' while out shopping for a bigger cock...

A few weeks later, Chloe was a regular weekend resident in our house. Once I was home on Friday evening, I would shower and shave, and then spend the rest of the weekend as Chloe. This included going out shopping and even the occasional meal out. I'd worked hard on my appearance, and especially on my voice, and now I felt confident that I could pass even close scrutiny by anyone. Of course,...Read On


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


Telling Mom I’m A Crossdresser Part 5: Movie Night and Gangbangs

5th installment of Missy, Plz rate and comment. :)

I had decided to take a few days off from being Missy after Stan and Roger had left and my mom and I were finished with our little girl time. I spent the next few days just continuing with life as normal except for the throbbing pain in my asshole and my cock from the 3 days of constant sex. I couldn’t stop thinking about all the things I had done as Missy and all the kinky fetishes I...Read On


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


Becoming Chloe - Part 12

A meal with a difference...

I walked through the door, and almost immediately all my resolve disappeared at the sight that met my eyes: my wife was sitting on the sofa with her legs spread wide with Tina between them, eating her out like no tomorrow! Vickie's knickers were wrapped around one ankle, and she held up her legs high to give her lover better access to her quim. It glistened in the late afternoon light with...Read On


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


Falling for Zak

A young man let's himself go to another man's desires

I hadn’t noticed the time, and I’d missed the last train home. The student party was fun, but I was in a bit of a panic not knowing what to do. People were leaving, and the crowd was thinning out. If it had gone on for several more hours, I would have stayed there and taken the first train in the morning, but that didn’t look likely. The hostess was already clearing up. I figured she’d...Read On


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


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


Mom's Old Boyfriend: Part Two

Courtney becomes an escort like her mother, after fucking Ron good like she did.

Having adopted my mother's appeal for wearing sexy clothing and turning on men, I had just sucked her rich former boyfriend's cock while she flew to Las Vegas for a long weekend with her new rich boyfriend. Mom had a love for the jet-set lifestyle and I was sure she was enjoying staying in an exclusive hotel and fucking her new boyfriend's brains out when he wasn't at the table gambling....Read On


Returning To Old Habits

After an extended break, I return to an old hobby.

Like many cross dressers, I found my habit has a certain ebb and flow. I would bury myself into my kinky hobby for several weeks, only to hide everything away again. I used to have purges too from time to time, where I'd convince myself it was wrong and throw my clothes away, swearing I'd never do it again. The last time I purged was in my mid twenties. I'd been with my then girlfriend for...Read On


All the Way (Part2)

Kathy and Brenda go out

When Michael stepped inside and closed the door, he gave Kathy the same kind of kiss as his wife had. He was quite an imposing man; short cropped blonde hair, very piercing pale blue eyes, a little over six feet tall and built sturdily, weighing somewhere around two hundred pounds. My heart skipped a beat when I took in the complete picture. Now I wondered how Kathy would convince the woman...Read On


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


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


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


My Sexual Odyssey Part 1 How I Got Started

This is the first in a series of stories that will cover my sexual experiences in chronological orde

I was always extremely sensuous, expressed in the love of the feel of satin and silk, as well as the feel of going barefoot, which was nearly impossible in the city, even indoors, not part of the culture. Where I live now it is, and so I go not only barefoot but also nude when at home. I don’t know if this is significant or not. However, the first time I noticed anything unusual was...Read On


Becoming Chloe - Part 3

Chloe gets her name - and much more...

When we arrived home, I was desperate to change, but Vickie said no, much to my frustration. The rest of the afternoon went like any other Saturday, and after dinner, we sat and watched tv for a while. Around nine o'clock, Vickie got up and suggested that we have an early night. By now my frustration had almost abated, so I followed her upstairs and we both got ready for bed. I was delighted...Read On


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


The Change Up - Part 2

Deedra has her first date out and meets new friends

I watch Emily get into her car and drive away. My mind just can’t believe what just happen. The clock on the wall says 5:00 oh my. I only have four hours to get ready. I am opening the packages that Emily drop off for me, the dress looks utterly gorgeous, lace and beading should be outstanding on me. Next the shoe box, the phone rings, looking at the caller id it's from India . I snap back...Read On