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Crossdressing

9

Making friends with my housemates

People always react in different ways when they find out about my cross dressing. Girls are usually more accepting than guys but everyone is different. I was twenty-two when I went to university and decided I would be completely open about it with everyone I met there. I found that most people were pretty cool with it, although some took some time to get used to it. I spent the first...Read On

9

becoming marie part 4

the following week at the air raid shelter

During the following week, I had been getting hornier and hornier, thinking of the weekend visit to the air raid shelter. I popped into town during the week to get some make up and clothes to wear for the following Sunday. This was going to be a bit awkward, but egged on by my urges I set off shopping. I decided to try the charity shops first. In the first shop, I found a nice short, black...Read On

25

Jack's Dirty Secret

Jack walked into his bedroom, seeing his wife laying on the bed with a dildo in hand.

Jack and Mary had been married for ten years or so. Mary never thought that Jack would keep such a large secret from her. She sat at the house all day and did laundry, Jack's and hers. She never usually did his since he's picky, but she was bored and it needed to be done. As she was putting away some of Jack's clothing in his dresser, she saw something. It was a shiny pair of silk gray...Read On

18

One of my first times

My first time with a guy

They say you never forget your first time. For me that's kind of true but in my attempts to seduce over the years I've claimed to have so many first times and I definitely don't remember all of them. Being bisexual and, of course, with my dual gender identities I have probably had more first times than most though. I was still cross-dressing in secret in my late teens and I'd never had...Read On

12

My girlfriend caught me wearing a dress

A guy that likes to wear a dress, gets caught

My name is Billy, and I'm twenty-six. I have black hair, and brown eyes. I have a girlfriend that I've been seeing for a few years now. I should mention, that I occasionally like to dress up. I'm not talking wearing a tux, I'm talking about wearing a dress. That's right, I'm a cross dresser. Very few people know about it, and my girlfriend, Phebe, wasn't one of them. My mom knew, and a...Read On

11

Becoming Marie, Part 3

Group fucked in air raid shelter

On one of my bike rides and visits to the Transporter Bridge cottage, I met a guy who told me of a cruising spot not far from there. He said that the place was much safer than the toilets. He gave me directions to it and added that the place was always busy. On the Sunday of the following weekend, I set off on my bike wearing a loose tracksuit as underneath I had a set of lingerie on. I...Read On

10

My Oddesy 1 - Glen (here and gone)

A (mostly) true story of my first time dressing for another

"But mum. I'm too sick to go to school." I give my best fake cough. It was late senior year and I had been busting my balls for months. I just want a day at home alone. She finally replies after a minute of withering glares. "Fine. I'll call the school. But you're seeing a doctor Monday if this persists. I'll be back around five." "Sure. Whatever." I lay perfectly still until the sound of...Read On

6

Ever tried dogging?

The trilogy concludes with a hot threesome in a Steam Room and a late-night bukkake

Nick steered his sleek silver turbo-charged coupe across the deserted Cambridgeshire by-roads towards Ely. The town was justly known as 'the ship of the Fens', as the tower of its majestic 16th century cathedral was like a navigational lode star. Ely's train station was only a few hundred yards from the cathedral and Cathy stood waiting in the shade of the station building's canopy. She wore...Read On

27

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

18

While the Cats are Away

Kelly's best friend catches him dressed up

Thursday night, mom is going to visit relatives out of town; dad is away on a business trip and not supposed to be back until Saturday. It took a lot of convincing that being sixteen is old enough to be able to stay home by myself and not have to go with mom to visit relatives. Dad was going to be home in two days and I would be going with him to the family ranch. Finally my mom relented and...Read On

18

My wife finally indulges in my fantasy

This story is a work of fiction I wrote for my wife.

I come home from work to find you dressed in your sexy jeans, a tighttee shirt, and a pair of heels. I can tell you are horny by the way you tell me to get into the shower and that my clothes are laid out for me after I finish cleaning up. My cock throbs as I shower and lather my body up with some scented soap. I know you want me squeaky clean so I insert a soapy finger into my ass,...Read On

9

Call Me Julie Part 4

Julie is not the only one in for a surprise.

Scott coaxed me out of the car and we walked the ten feet to the front door, he was practically dragging me while reassuring me that everything would be alright. "Kelly is expecting us, don't you worry about a thing." "She is expecting me? Dressed up like this? Somehow I don't think you are telling me everything Scott, if this ends badly I will be kicking your sweet ass," I told him. ...Read On

15

becoming marie part 2

the second part of my true adventures

After my encounter with Kevin at his office, I knew that I wanted more.I had my own place and had started to build up a nice collection of lingerie, which I would often wear while wanking to my slowly built up collection of porn. This was before the age of internet so it was sometimes hard to get porn, mainly from friends, nearly always straight. I would always imagine I was the female...Read On

4

Paris: Sex Extreme

From decadence to debauchery in 48 hours

Seated in the famous Champagne Bar of the Euorstar Terminal at London's St Pancras Station, Nick toyed with his champagne flute. With one eye on the giant overhead clock, he was getting anxious about the departure of the Paris train. Then he saw Cathy approaching. She looked stunning, turning several heads as she alighted from the escalator. She was wearing a long-sleeved double-breasted...Read On

14

Stuffing my hard cock into skimpy panties and going to the gloryhole

Wearing slutty panties and sucking dick!

I had just gotten home from Victoria's Secret and was about to start trying on all of my new panties. I was putting on my first new sexy thong (it was a hot cotton pink one) and just as soon as the string slid up my ass, my cock got rock hard, making for a very formidable tent. I knew then and there that I would have to suck a dick and swallow some cum. I had always had a fantasy about...Read On

15

Becoming marie part 1

How i became a cock hungry slut

From the age of sixteen I had discovered my liking for dressing in women’s undies. It was usually my older sister's panties and skirts whenever possible. When I finally left home at eighteen and moved into an apartment in the town center, it really took off. I had had a few encounters with a few guys, mainly glory hole fun in the local cottages. On a few occasions I found the odd pair...Read On

8

Call Me Julie part 3

The night gets more interesting

I stretched and reached out like a cat waking from a nap. Scott was resting on his side with his elbow down and his head resting on his hand looking down at me. "Enjoy your nap?" he asked as he stroked my shoulder. "How long was I out, how long have you been watching me?" I replied. "Not too long on either of your questions," he replied. I glanced at the clock and it read 8:00,...Read On

16

Carl, Carla and Hannah - Epilogue

The conclusion.

It's now been nearly a year since Hannah and I got married, and my goodness, what a year it's been! As soon as we reached the Bahamas on our honeymoon, Hannah and I (as Carla, naturally) had an absolute wonderful time. The days were full of warm sunshine, and the nights were full of... well, I think you can guess! When we got back, my plan to live full-time as Carla started well. After a...Read On

3

Night at the Video Store, Part 2

a sissy, very blonde, bimbo slut goes to a video store in a rough, black part of a big city.....

There were some strong, black street toughs in the SUV, but they got quiet when they saw me step off the curb into the parking lot. My nipples began to get hard under my little black micro mini dress and I could tell they were looking at them. I must admit, my platinum blonde wig, a huge Vegas style wig that went down my back to my butt, swung right and left as I moved my head back and...Read On

6

Carl, Carla and Hannah - Part 25

The Honeymoon Party - the final chapter.

A knock at the door broke our reverie. Hannah turned to me quite pointedly and said that I should answer it. I looked at her questioningly, but she just gave me her mischievious grin. "Call it my wedding present to you, Carla," she said, enigmatically. "Now, go see who's there." Bewildered, I walked to the door of the suite, loving the sound of my wedding train rustling behind me. As far as...Read On

10

Carl, Carla and Hannah - Part 24

Carl and Hannah's big day, and after...

At last, the big day was just a few hours away. At ten o'clock the following morning, Hannah and I were to be man and wife. Or at least, that's what the outside world would see. The reality was that, after our honeymoon, I would live almost totally as a woman. Now that Hannah was settled into her new job, she became even more bossy and dominant at home, although I never let her get it all her...Read On

9

Call Me Julie part 2

some secrets are meant to be shared

After regaining some of my composure, I got to my feet and pulled Scott up to his. I kissed him and pushed him up against the wall locker and pulled his shirt up and over his head. I kissed my way down his body and stopped at his gym shorts. I hooked both fingers at the waist band and yanked them down. The most perfect cock I have have ever seen was straining against the pretty pair of panties. ...Read On

23

Aunty's New Girl

Falling into the strange world of Aunty Trixie...

This is the continuation of Tickets Please! Shakily, I keyed in the URL from Trixie's card, my mind in turmoil, heart racing as her sweet gift seeped from my aching pussy and soaked into the lacy panties I was wearing. I was wedged behind one of the 'tables' thoughtfully supplied for the busy passenger. You know the ones, if you move a fraction either way you end up concussing your...Read On

7

Carl, Carla and Hannah - Part 23

The stag night, and the morning after...

There was two weeks to go before Hannah and I would become man and wife. And then, although nobody else knew, we planned to live as wife and wife. In the meantime, the final touches were being made to prepare for the big day. I decided to have my stag night a couple of weeks before the wedding, and I included Tom and one of his friends in the party. Graham, like Tom, was bisexual, but it...Read On

11

My first boy experience

First time cross dresser ends up with well hung guy..

It was my friend, Karly's birthday. Her choice for going out to celebrate was a drag night at a club. It wasn't so much fixed on drag as it was on gender parodies and cross-dressing for fun. I had been a closet cross-dresser for a long time, although I had told a couple of girls I knew. Everyone was going to cross-dress and have fun, but I was going to revel in it. I had never been with a...Read On

8

Carl, Carla and Hannah - Part 22

Hannah gets a promotion, and Claire pays a visit.

A couple of weeks later, Hannah came home and told me that the rumours had been true, and Claire had been promoted. As Hannah had been at the company the longest in her department, everyone expected her to apply for Claire's old job, and the general consensus was that she'd get it. Hannah was determined to get it as well, telling me that the extra money would come in handy for the wedding....Read On

10

Free Clothes

Not what I expected, but definitely what I wanted.

I guess it is something that goes through the mind of every new or closeted crossdresser. Shopping for new clothes as a guy is awkward because it is difficult to do without making it obvious it is for you. Yeah you can go online, but it’s tough if you’re not used to the sizing and the clothes never seem to look the same as the picture. Thus, when searching for playmates on Craigslist, if you...Read On

14

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

16

My Sexual Odyssey Part III: Becoming a Slut (Continued)

A continuation of the journey described in part 2

We got to Tom’s car, and he opened the door for me, then walked around and got in himself. The drive was short and uneventful, and we parked behind the club. There were some people arriving at the same time we were, and I noticed several who looked like they could be CD’s. We approached the club’s entrance, and I began to feel more relaxed. It is always uncertainty that is anxiety-producing,...Read On

7

Carl, Carla and Hannah - Part 21

Carla spends Thursday night with Tom, while Hannah hears of a possible opening...

A few days later, I rang Tom, this time leaving my number visible. We talked for a while, and we both agreed that we'd had a good time, and would like to see each other again. Before I hung up, we'd arranged for me to go over the following Thursday, as that was Hannah's night with Claire. Hannah and I spent the next few days thinking about the wedding, looking at suitable venues for...Read On