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Crossdressing

Our crossdressing (cross-dressing) stories feature tales of either gender (usually male) dressing up in the clothes of the opposite sex, for reasons of sexual gratification. Crossdressers are akin to the transvestic fetishism, which is a sexual fetish for the clothing of the opposite gender. The crossdresser can be of any sexual orientation.

2

Stage six of my journey to becoming Joann

A defining year in becoming a complete cross-dresser.

As I awoke on Christmas morning I found three presents on the end of my bed. There were handwritten tags on each with the message: open in private. There was no doubt in my mind as I opened them that they were from Sis. The first was a body shirt that pulled down and snapped in the crotch. It was white with a v-neck trimmed with lace around the neck and sleeves. The second was a set of...Read On

16

My Own Story

A story about how I started crossdressing with a bit of a fantasy encounter

I have been into pantyhose for as long as I remember. I am not sure why I love them so much, but I can't seem to get enough, especially how beautiful women's legs look when they are wearing them. When I was sixteen I remember playing around my mothers nylon covered legs when she came home from work. She would always wear very sheer hose and had wonderful legs. During the summers when she...Read On

7

Stage five of my journey to becoming Joann

Enjoying myself feeling like a women

As I opened my eyes it was quite light. I sensed it was late morning. Bob was still spooning me, but his dick was soft and must have pulled out of my ass sometime through the night. I quietly rolled out of the bed and walked to the bathroom. Before sitting to pee, I reached around and pulled another condom from my ass. I guess when he lets his dick soften inside me it shrinks from the...Read On

11

Girly Obsessions

Based on a real adventure with embellishments of wishes

All of my life from the time I was young to now at twenty-five, I have had an obsession with women. It is not that I like them (which I most certainly do) but more that I want to be like them, act like them, and most importantly dress like them. It started when I was very young and developed an interest in the legs and nylons of women which I found fascinating. The sheer and soft material...Read On

5

Frank

A crossdresser tries to please his lover

Frank didn’t vocalize his orgasms. So I never knew he’d cum until he stopped his motion and pulled out of me. Then I’d look over my shoulder with a smile and ask, “Did you cum?” And Frank, already backing off the bed, his big cock curving downward now, would reply, “Yeah.” Although normally quite chatty, in the immediate aftermath of sex Frank turned into a man of few words, a regular...Read On

8

A Sissy's First Dildo Experience

After ordering his/her very first dildo, this sissy had a very, very special experience.

Buying a dildo online was a bit nerve-wracking, honestly. Not for any huge reason or anything – I live alone, and the packaging is supposed to be discreet anyway, but there’s just something that made me nervous when I first put in the order. Sure enough, it wasn’t like it was a fat box labeled, “Tasty Black Dildos for Sissy Whores,” all around it; just a plain box, inside which was some...Read On

3

For Mistress Sarafina (Part One)

A submissive feminized sissy serves her Mistress

Alice was clad in a tight pair of black lace silken panties that felt so smooth upon her caged genitals. This pair of panties, more so than any other pair Alice owned sent aroused shivers up and down her whole body whenever she was made to wear them by her Mistress.   Mistress Sarafina had left Alice a detailed text message earlier in the day explaining what Mistress Sarafina expected...Read On

7

A boy's femininity awakened, Part two - early girlhood

A sissy boy's experiences, good and bad, as a girl

Sissy boy John was petticoated at Secondary School after falling foul of Jenny Tough, a school bully. During his week of penance, John found that he was more at ease and happier amongst girls than with boys. John decided, therefore, to explore his feminine side by trying to live as a girl. John’s Mum was shocked when he first arrived at home wearing a schoolgirl’s uniform but calmly listened...Read On

9

A boy's femininity awakened, Part one

A sissy boy is petticoat disciplined in school and discovers his feminine side.

In the North East of Scotland, large families were the norm even up into the 1950s.  So, when I attended the local Primary School, there were scores of children of my age there, all shapes, sizes, and temperaments. This meld of kids meant that I didn’t stand out from the crowd despite being a softy. My time at Primary School was therefore quite comfortable and peaceful, but this...Read On

1

Bobbie Breaks

Bobbie submits to Joe's discipline.

Our routine continued for the rest of the time Amy was away on business. I would ask for money, and Joe would usually unbuckle his pants without a word. I’d give him a blowjob, and he’d give me some cash. I enjoyed it because it was the only time I was allowed to take my bra off. I channeled my frustration at having my girls locked away into being the biggest thot I could. He didn’t want to...Read On

11

Under His Thumb

A submissive college student submits to his alpha male roommate.

I was sitting at my desk in a t-shirt and running shorts when my roommate Dave came in. He saw the towel I’d dropped on the floor, and immediately his nostrils flared. “How many times have I told you to hang up your towel?” he said as he bent over to pick it up. He hung it on a hook on my closet door. I looked back at him and rolled my eyes. “You’re so anal,” I said, turning back to...Read On

16

Stage Two Of My Journey To Becoming Joann

Falling further into the journey of cross-dressing

Life was becoming a little confusing. I was out of high school and attending the local community college part-time at night while I worked at the machine shop during the day. I played soccer on the college team in the inter-county conference. Mom helped me buy a nice used car. Still, I wore panties, a bra, and nightshirt to bed every night. Sis was working part-time at a hairdresser while...Read On

21

His First Time In A Dress

Andy visits a very kinky club

The next morning, Andrew woke up to find a text from Emily on his phone. “Come over at 11,” it read.  “Gr8 idea 4 2nite.” That sounded intriguing, he thought. He showered, made himself some breakfast, then ambled over to Cavendish Hall. When he got to Emily’s room, Calum was already there, sitting with his feet on the table and nursing a cup of coffee. “Hey, Andy,” he said with a wave....Read On

18

Bachelor Turns Bachelorette Slut

A young groom's best man feminizes and seduces him.

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...Read On

15

Shall I Tell You About My Wife?

How I met my nymphomaniac wife.

Time has been exceptionally kind to my wife Samantha. As a sixth form teenager, her stunning looks, along with her 36 DD's, attracted the attention of the male students and some teachers at her school. Her chestnut brown hair flowed down to her waist, and her face wouldn't have looked out of place in any beauty pageant. It was no wonder that she had an everlasting stream of suitors...Read On

10

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...Read On

10

When Danny Met Judy

A Mrs Robinson moment!

When Paul and Sue announced they were taking a holiday in the new year, I was as eager as they were for that week to come. We had a reciprocal arrangement, whereby the couple that remained at home would periodically look into the other's house, to water plants, remove the build-up of mail behind the front door and just generally check for anything untoward.   I'd just dropped them off at...Read On

5

The Clothes Make the Sissy

Bobbie and Amy go shopping.

I don’t know what happened to my clothes. It seemed like they just kept disappearing. Amy’s solution was always for me to wear her clothes, and I must admit that they made me feel really sexy. I’d worn women’s clothes before here and there, but it was always for a party or some special function where it was expected or at least accepted. My feminine build always gets lots of attention...Read On

12

Hidden in Plain Sight 2

Marc was too excited to sleep that night as his mind was swimming with anticipation about his meeting with Charlene. His fearful side reminded him that he had her business card and that he should call her and cancel their meeting. His experimental side chimed in that she had discovered his secret and didn't laugh or tell his parents. She instead kissed him and then invited him to meet...Read On

2

The Transformation of Ms. K (Part 1)

Asian boy has a secret life as a fetish dominatrix

By day, I'm an average Korean guy, a bit on the fat side, my whole life I haven't been very attractive to women. I'm very timid and shy as a boy, very much a beta. I never even had sex until after college and my dating life has always been pathetic.  I've always had a bit of a tight rubber and latex fetish. As I became older, I began buying some pieces of latex and dressing like a...Read On

0

Barrack Room Betty - Chapter Fifteen

Navy Transvestite Girls visit Sydney Australia

Chapter Fifteen – Bettys Down Under Michele had an emotional last day with Ying. As well as lovers, they had become good friends. Michele promised to write to Ying and vowed that one day she would return to Thailand and they would reunite. Their last night together was a sex-charged boozy affair and Michele rose early the next morning and left Ying fast asleep in the hotel. She...Read On

17

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...Read On

0

Barrack Room Betty - Chapter Fourteen

Michele meets a Bangkok ladyboy and they strike up more than just a friendship

Chapter Fourteen – Supergirls Bangkok “I’ve fucking had it with Jason!” Michele spat at Rod Latham “That fuckwit tracked me down and found me in a bar in Naples and created an absolute shitfight. And every night I’m here in the club, he carries on like a petulant child whenever I work a punter and in particular Lieutenant Steve Winters who is one of our best customers. When is...Read On

1

Barrack Room Betty - Chapter Thirteen

Transvestite Wrens visit Naples and have fun in the sun.

Chapter Thirteen – Naples – Whores and Princesses The Ark continued her voyage through the Mediterranean Sea, exercising with the Task Group as she went and arrived in Naples a week after she left Gibraltar. Lieutenant Steven Winters, RN, became a regular at Barrack Room Betty’s whenever there was no night flying. He entered into an arrangement with Michele that she would always be...Read On

2

Barrack Room Betty - Chapter Twelve

Crossdressing sailors operate a brothel on a navy ship

Chapter Twelve – Pleasuring an Old Friend Ark Royal sailed for her deployment in a small Task Group of three ships and on the first night Barrack Room Betty’s opened for business and was an instant success. At first, the main earner was gambling and booze but as the ship got further away from her home port the temptation for the punters to ‘tap’ the attractive transvestite hostesses...Read On

1

Barrack Room Betty - Chapter Eleven

The Bettys reunite on board the Navy's flagship where Michele turns adversity to her advantage

Chapter Eleven – An Offer You Can’t Refuse! Michele remained on her knees and waited for Chief Writer Rod Latham to come over to the bunk to see what he wanted of her. It turned out he wanted a quick fellatio session, which she provided. After the three sailors had satisfied their urges with Michele, it was time to talk business. “So as you can see, compartment Six Quebec Delta Alpha...Read On

2

Barrack Room Betty - Chapter Ten

The Betty's go to sea in the Navy but doesn't stop their crossdressing antics

Chapter Ten – Sea Daddies and Sea Mommies Seaman Michael Nyland graduated from Recruit School in March 1974 and was immediately posted to HMS Raleigh to commence training as a Writer; a sailor specialising in pay, personnel matters and administration. He was glad to see the back of HMS Chelmsford; Spike and the three other Leading Recruits had passed out at the end of January and had...Read On

1

Barrack Room Betty - Chapter Nine

The ROP is over at HMS Chelmsford and the 'Bettys' go out for a night on the town for the first time

Chapter Nine – Pink Pussycats All good things come to an end and the six-week Reduced Operations Period at HMS Chelmsford ended on 15th January 1974. The Wrens and Leading Recruits were very busy as that day approached. The Depot needed to be de-winterised and preparations made for the return of the Ship’s Company, the other Recruits, and the Wrens from their leave. Even Petty Officer...Read On

11

A Close Encounter Part 3

The perfect ending to an awesome night!

Homeward Bound   "Well, how was it for you?" My question was directed at my wife's reflection in the rearview mirror. She looked quite fresh considering that she'd just been fucked.   "Yeh, it was good! Pass me a tissue, babe." Sam stretched an arm between the front seats.   "It was certainly different!" Paul's assessment of the last hour's shenanigans raised a chortle.   "Not 'aff!"...Read On

1

Barrack Room Betty - Chapter Eight

Four sailors and four pretty trannies locked up over Christmas, what are they going to do but party?

Chapter Eight – The Christmas Party Lieutenant Steven Winters was an extremely good-looking Navy fighter pilot whose last posting had been aboard the aircraft carrier HMS Ark Royal. There was some unpleasantness when, after a wardroom ladies dine-in night on board the ship, the rather portly Executive Officer had opened the door to a hangar workshop and found his glamorous wife bent over...Read On