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An Introduction To Crossdressing, The Finale

As Jackie, Chandra and I finished up our food, we chatted about the evening yet to come.

Reliving our evening’s events had Jackie and Chandra pretty worked up. “You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?” Simultaneously they both grunted, “Yes we are!” I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy. “You should probably save some of that for back at the...Read On



A secret assignation in a country hotel turns into an unusual menage a trois

Dusk. As he turned off the highway into the country park hotel, Nick was relieved to note that its car park was barely a quarter full. Pulling his overnight bag from the back seat, he headed for the brightly-lit reception lobby. A giggly gang of women were disembarking from a mini-coach. Most were clearly very drunk. In the hotel's spacious lobby he quickly spotted Mark,...Read On


Not Crossing The Line

Crossdressing brings me closer to a woman than I expected

When I was a kid I had a book called, ‘What Do People Do All Day?’ It made a start at teaching me about the variety of jobs that exist in the world. As an adult I feel it would be equally beneficial if there was a book as simple as that one which answered the question, ‘Why do people do the things they do?’ Part of the trouble is that I often do not even understand my own...Read On


Dawn Summer

Oppressed and Underage. Sometimes you just got to take matters into your own hands.

As I climbed aboard the bus, I couldn’t help but feel a sense of relief at my escape. I never realized how free I could feel finally escaping my father for good. Maybe, I should back up a little bit for those of you just catching up to my story. My name is Dawn Summer. I grew up a rich little boy with a father who never quite understood, or cared to understand me. I wanted to become an...Read On


The Change Up - Part 3

Deedra continues to have fun on her first date, and gets what she been hoping for!

Sammy looks at us and says, "You know that Elsie gets pissed when you tie up the ladies room like that. Then Trish came back and saw that you were all gone and wanted to know why you didn't invite her along?" Emily says, "You know Trish is working, and it's too early for Elsie to be at the club." The band started to play swing music. I remember the song, Jumping Jack. I danced to it...Read On


Fun on Business Trip (part 1)

This is a account of real-life events. -------------------- After the first couple of outings at the mall, I lost some of the nervousness around shopping fem clothes and started actually enjoying it. So much so, that over next two-three weeks, I visited many more stores and ended up buying nearly a dozen skirts, bra and sexy panties. I had begun to get a hang of interacting with the...Read On


My First Taste of Cock

Tammy blows and swallows her first cock.

After fantasizing for so long about what it would feel like to dress as a slut and suck a cock, I decided it was time I tried the real thing. I posted an ad on Craigslist with a couple of pictures of me dressed, asking for someone to let me dress for them and swallow their load. I got a lot of responses and most of them just sounded creepy except for Matt. Matt was 36 (I was 25) and a hot...Read On


A Break in Action

Settling into a new life is easier than first imagined.

I took a good long look at my now shoulder length hair. It still looked very straight and masculine in contrast to my wig, but at least I had something to work with now. I decided that it was about time to start wearing my natural hair instead of the very nice, but still uncomfortable wig I’d used for four months now. Since I’d left my old life, my chest had grown between an A and B cup...Read On


Cindy's makeover

This is a account of my makeover and my three days in London, not a lot of explicted sex in the stor

I would like to share my latest cross-dressing experience. Like many cross-dressers, I dress up part-time. I am married and my wife does not know of my fetish of warning woman clothing. My dressing need stems from my enjoyment to the attention I received from admires. I am new at this cross-dressing having only started dressing five years ago. Many cross-dressers started their fetish when...Read On


Christina and Cheryl - part 2

Christina and Cheryl venture in to the public

"Pedicure?!" I was alarmed. This had all been fun and very sexy, but a pedicure? That would mean I would be venturing in to the public, something I had previously barely even considered. Would I pass? Would I be ridiculed? Would I be verbally abused? Would I be physically abused? These were the things that crossed my mind at first. But then I considered a different scenario. Would I be...Read On


Mistress Sarah makes Evie a Sissy 2

The continuing story of Evie and Mistress Sarah

"Look at you Evie. You're so slutty in your teddy and stockings,” said Mistress Sarah. Then she looked down at my hard cock and said, "....and your clitty is so big. Excited are, you?" Mistress Sarah reached out and firmly squeezed my cock a few times. It was a welcome sensation that reverberated though my entire body. Before I could respond, she ordered, "Turn around slut. Let me see...Read On


Leigh and Leila - Fantasy of a First Night

CD Leila gets read for her first encounter with her girlfriend.

“I don’t know when to stop talking, do I?” I asked. You smiled and kissed me again. It took my breath away. I closed my eyes and let myself get lost in the feeling. It was like nothing I’d ever imagined, nothing I’d ever felt before, nothing I could imagine living without. Your fingers moved just the slightest bit. I nearly came, my cock straining hard against the white satin thong. Your...Read On


The Meeting

Some first meetings turn out better than others

I initially met Richard through a TG Community site and we seemed to hit it off from the very start.   He was very open about his likes and dislikes, about him being a TG admirer, about having had a fair number of encounters and dates, but he never pressured to know anything about me.   Drawn by his gentleness and gentleman ways though I found myself sharing my deepest dreams and...Read On


My oddesy 2 - Liam

A friend cheers me up

It had been a few weeks since Glen's puzzling rejection and I was in a slump. I hated my body more than I had in years. Not even sneaking into my sister's old room and playing dress-up could cheer me. And my best friend noticed. Liam was in most of my classes at school and we knew each other since third grade. He had olive skin and a solid German build. Noticing my gloomy disposition he...Read On


The Cabin, Chapter II

I do my best to comfort the two frozen wanderers stumbling through the door.

I do not know how long I sat there gazing into the flames and sipping wine in complete peace. The wind outside was far away in my mind, but suddenly a huge bang broke the silence. The door flew open and slammed into the wall. Rain swept through the small cabin and sprayed me with icy cold droplets. I nearly fainted from shock, and the noise from my pounding heart overshadowed the howling of...Read On


The Frederick's of Hollywood Lingerie Model

Courtney's first job in Hollywood is as a Frederick's lingerie model.

When I first arrived in Los Angeles, I was staying at a motel on Sunset Strip in Hollywood. I had plans on working as a tranny call boy there. In the "L.A. Express" magazine, I saw an ad for a club on Sunset, called the Leather and Lace Lounge, that was popular with trannies and the men who liked them. I decided to go there and learn more about the tranny scene in Hollywood. It was three in...Read On


Skye High

Best friends discover their mutual romantic interest in one another

It was more of a small gathering than a party. Eight friends hanging out in one house for the night, to enjoy a a late night hockey game. In the mean time, the living room stereo system played the local electronica radio station, while the small group enjoyed various activities. One, however, was not having a good time at all. Skye sat in the upstairs bedroom, her back to the door, her...Read On


First Night Nerves - Part 2

Tina agrees to meet Barry without 'the girls'

I sat by myself on the bus, my briefcase on my knees, counting the stops and wishing it would go faster. Since Barry’s text message last night and his surreptitious call to my mobile that morning, I had been so excited, planning what I would wear to please him most. Debbie hadn’t heard the beep on my phone so didn’t know that I would be meeting him without her that afternoon. So far I had...Read On


In Her Shoes Part 3

This is the final part so please read both other parts to this story to understand it fully.

I guided Peter into the main shopping mall in town leading him straight into a shoe shop. The girl in the shop fetched a few pairs for me to try on and I relished asking Peters opinion. He tried not to look too obvious that he was hooked on my shoes and feet. I 'hummed' and 'ahmmed' a short while, telling the girl I was undecided and may well be back later. Grabbing his arm once more we...Read On


The Next Night - Crossdresser: Part 2 of 2

The next night and a second session with Jenny.

I woke up early from the sunlight shining through the windows. We’d forgotten to close the curtains when we collapsed into bed last night. Jenny was already awake and watching me.  ‘I was just about to wake you up with a blow job,’ she smiled. ‘Funny, I was thinking of doing the same to you!’ I laughed. Jenny kissed me then turned around in the bed to lay on her side so our cocks were...Read On


Master's Reminder

I had been seeing Master John for about a year now and thing’s were going well or so I thought!

I had been seeing Master John for about a year now and thing’s were going well, or so I thought. I arrived at his home like any other weekend in the outfit he wanted me to wear for my punishment. He would always choose the week before and I knew that there was no argument whatever he wanted he got. I hoped that I had got everything just right for him. Anything slightly out of place or...Read On


Confessions of a Sex Crazy Cross Dresser Part 8

Sandy's adventures continue in Chapters 15 and 16 of book #1

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...Read On


My Sexual Odyssey Part 2: Becoming a Slut

A continuation of the journey described in part 1

After having had a few experiences, I became slightly more comfortable with my sexuality. I decided to branch out a bit, and see what life had to offer. I wondered whether there were any bars or clubs that I could go to to meet people who were looking for someone like me, so I went online and discovered, that yes, there were quite a few such places. It is so wonderful having the internet...Read On


My First Time Final Chapter

The conclusion of this story

The Friday that Lydia told me about had finally arrived and she would be bringing some of her friends over for drinks after work, and I was to serve them as Melissa. Lydia had also advised me that unlike the dominatrix persona I used during my first outing on Halloween, Melissa the maid, was totally subservient. That morning after my usual visit to the gym I cleaned the house and set up...Read On


Mistress Lucy takes control

Power reversal; the usually sissy crossdresser Lucy has fun with her girlfriend, Belle.

Belle had finished disrobing and stood in her bra and thong, both pink, following Lucy's command. The latter stood in front of her girlfriend and, with a light touch of the shoulder, pushed Belle down on to the bed. Belle looked up at Lucy expectantly, eyes wide. Neither girl wore any makeup; they'd been awake for a couple of hours and, having spent the morning in the kitchen loafing around...Read On


A friend with something extra.Part 2

Ian and Grant test the waters.

Ian headed to the bathroom to clean up. As he did he allowed his mind to recall the most recent events of the evening. He arrived at his best friends house for one of their pizza and movie nights and discovers a sexy girl in his buddy's bedroom. He soon discovered that the sexy girl was, in reality, his friend Grant. He didn't look or talk like the Grant he knew, he talked and looked like...Read On


Call Me Julie part 5

Julie is not the only one with a secret.

Kelly is kissing me passionately, and I am kissing her back. Her hands are all over me as she feels me up. My tucked package is straining against the material of my panties as she grabs and gropes at my feminine attired body. Her hand snakes its way under my dress and into my panties, which she pulls down enough to release my cock, and tugs on it vigorously. She breaks the kiss and snakes down...Read On


Jaime's Way (part 2)

Sherry has transformed Jaime into a sexy slut

I awoke to feel the dried cum on my face, ass and balls, and then remembering how I got that way made me smile. Crawling out of bed I made my way to the bathroom and took a hot shower and then easily shaved my already smooth legs. Out of the shower I brushed my hair and did what I could to make it appear more feminine. After I put on my make up I walked back to the bedroom and slipped into a...Read On


Weekend Discovery 1

Friday had finally arrived. Andrew Lippincott glanced at the Rolex on his wrist and then began to pack his attaché case. It was only 4:00 pm but he was the office manager and one of the perks that came with this title was the ability to leave early. Winter had the city in its grasp and a travelers advisory had been posted.That meant there would be no unannounced guests to prevent him...Read On


Telling Mom I'm A Crossdresser part 13.5: Missy Brings Home A Stud

the continuation to Missy going out and finding a man.

I told Thomas all the details of why I was out this night and he loved the idea. He took one of his Viagra and he led me out of the bar. I felt a little embarrassed at all the cum leaking down but some of the cross dressers were just smiling at me like they were saying “you go gurl!” which made me a little proud. Thomas followed me in his car until we got to my place and I took him by the...Read On