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Crossdressing

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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.

63

His Dirty Little Secret

His wife finds his stash of clothing, leading to some role reversal

Julia was doing some spring cleaning in the house. She had scrubbed everything, cleaned the oven, scrubbed the floors and was in the process of cleaning out the closets. Stuffed in the back of a closet was a bin. She didn’t know what was in it. The sight that greeted her caused a jumble of emotions in her. The bin was full of women’s clothing. It was all silky and sexy; Nightgowns,...Read On

45

Born To Be A Babe: Part Two

Wearing a sexy pair of hot pants, I go looking for men at the adult bookstore.

After discovering that I enjoyed wearing sexy little panties, tasting cum and having a big vibrator in my ass, I began to have these auto-erotic sessions, every day.While wearing panties and playing with my ass with a dildo, I would lay in my bed and fantasize about all the big cocks I wanted to satisfy for men. While I was only 16 years-old, I had decided I was a girl and I wanted to wear...Read On

22

Nights in pink satin

Forbidden desires are allowed to awaken.

It finally had happened. Paul couldn't resist the urge anymore. The urge to wear women's clothing. The urge to be degraded and humiliated. The first thing he had done was to have a shower and remove all his body hair. Gazing at his naked self in the mirror, he was pleased with the results. Forcing down a shudder of anticipation and excitement, he reached for the first garment. The feel of...Read On

22

Anonymous Encounter

An Anonymous Encounter of a Crossdresser with someone from Adult Friend Finder!

Well it was a boring day. It was fairly hot outside,somewhere around 93 degrees. The sun was shining, there were very few puffy clouds in the sky, and I was home alone. As usually happens when I am bored and home alone, I was horny as hell. I wanted to jerk myself off, but I wanted to do it to something different than the normal porn that I usually watch. I figured since no one would be back...Read On

20

A Whole New Me - Part 2

Lisa finds out what I've been up to

I had just finished cleaning up in the bathroom. A spontaneous encounter with my best friend whilst wearing my girlfriend’s thong had left me a bit of a mess and as for the thong... well I guess I’d need to find something new. Fully cleaned up, I ran naked into our bedroom and started looking through Lisa’s drawers for a new pair of panties. I wasn’t sure how I’d explain my change to her...Read On

17

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

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

13

I am Sissy

a fantasy of a taken slave by a pirate captain

The year was 1888. My name was Sebastian but I was now called Sissy since I was taken a slave. My father’s merchant ship was captured and sunk by the pirate crew of the Black Bess. I alone was saved for Captain Booth's pleasure. He was an escaped convict from the prison island of Australia. He was a huge beast of a black man, dark ebony skin stretched tight over enormous muscles that...Read On

12

Hannah, Carl and Carla - Part 4

Hannah explains herself.

When we got home, Hannah told me to take the bags upstairs to the bedroom and strip down to my lingerie. Once there, she started looking through the bags that she'd got while I was trying got undressed. In the first bag, there was a pair of black court shoes with a two-inch heel. She told me to try them on, which I did. Six hours ago I would have felt stupid and embarrassed to even...Read On

11

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

11

My First Encounter

This is about my first sexual encounter with a man

I had been cross dressing for years but only in private. I had also had a thing for bondage for a long time. A couple of years ago, I met two other cross dressers who were into bondage. We had been getting together every couple of months and playing bondage games with each other. We would take turns tying each other up and taking photos and videos. But, it was always clear that the other two...Read On

11

Carl, Carla and Hannah - Part 7

Claire starts work at the office as Carla continues her voyage of discovery into femininity...

I switched the six-thirty alarm off with a groan and turned to cuddle Hannah. After our customary two minute huddle, I kissed her and then wearily got out of bed. Without thinking, I sat down on the toilet and relieved my bladder, and then took off my bra and panties before stepping into the shower. The soothing warmth of the water managed to ease some of the ache in my body from the...Read On

10

A Master For Julie Jizzbucket

A story i have written in regards to my master and myself

I had spent the last couple months indulging in some mild cross dressing. After a few nights wearing clothes that made me feel so sexy and womanly. Until recently I had only worn panties, bras and a few sets of stockings and teddys that I had bought for an old girlfriend before she broke up with me to date a guy that had more money. I have also been going online to a site called Lush...Read On

10

The perfect day...

A t-girl's experience of getting dressed for ACTION!

The perfect day… The time was drawing near. He would have the house to himself! The realisation of a whole 4-month's planning would now come to fruition. It had been a while since he had gone out all dolled up, and now was a fresh opportunity to see his progress as a woman. He had been busy – his make-up collection had swelled considerably, and the addition of several choice pieces...Read On

10

Carl, Carla and Hannah - Part 20

Carla's night with Tom continues, and then Hannah has a surprise for her.

I lay down on top of Tom, and enjoyed the feeling of his arms around as he kissed me, telling me that I was great. I lay in his arms for a while, and we chatted about this and that. He told me a little more about himself, his failed marriage and what happened with a guy he met. All the time he talked in his low, sexy voice, his hands caressed my back, occasionally wandering down to the tops of...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

10

Telling Mom I'm A Crossdresser Part 12: Tow Truck Driver's Big Score

Missy gets her car towed and makes a deal with the tow truck driver

Sorry it has been so long since my last story. I have been busy with alot of things and I thank you for your patience. Lately, I’ve been working part time at a restaurant to make a little extra cash on the side along with my nights as Missy. I was saving up for a cruise I wanted to go on that I heard was for like minded people such as Missy. When people ask me about what I want to do...Read On

10

Capri

My first driving lesson

Friend of the family -Bi Curious story This is my very first story, I hope you enjoy reading it and I hope it inspires you to contribute My name is Jools I grew up in the west country from the late 60’s until the present day My tale based on a true story happen in 1970. At the time I would be at the tender age of 16. When your young the time can't pass...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

37

Caught, Used and Loving it Part 2

My descent continues

It had been two weeks since I had been caught and used by the mystery woman and her boyfriend. They had left as quietly as they came, and I was left kneeling on the floor dressed in all my best female clothing, cum dripping off my face, and my own cock dribbling cum on the floor. Since then, I had had only two emails. One was sent immediately after they had left and contained ten pictures...Read On

27

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

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 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

25

Mariah... My Wank Mistress

How I met Mariah, a crossdresser's dream...

We first made contact about three years ago, on one of those dirty dating sites. I was showing my tranny profile, Velvet, at the time, and was being hit on by a bunch of dirty old men, when this "Mariah" person said, "Hi." I was in a pretty sarcastic mood at the time, and was slightly peed off, as the guys I had been chatting to were only interested in one thing, getting their rocks-off. ...Read On

118

Halloween Trick or Treat Surprise

Dan and Susie go to a Halloween costume party Susie has him dress as a women and changes him forever

Chapter 1 –Susan Charity Event To my surprise Susie my wife of 15 years comes home from one of her many business trips. She is all excited about a Halloween costume party fund raiser, for non profit that supports women studies. The invitation states, the best couple for this evening will receive a free weekend in Bermuda. She wants’ us to go as couple switching genders.  Let me...Read On

47

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

43

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

42

Pamala's first adventure

This happened to me years ago when i was in the Army

I joined the army after I quit school in the 12 th grade. After joining the army it put a crimp in my dressing up as a girl. I did wear panties whenever I got the chance but I really wanted to dress up completely as a girl. I wanted to go out dressed and I have to admit I was attracted to several guys in my unit. My third year in the army I went to Viet Nam in December 1967. I was in the 101...Read On

22

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

19

The Slut Within part 2

part 2 of the slut within and if you like it PLZ comment :) enjoy!!!

As I continued on my knees, I felt my little thong riding up my tight little butt. My skirt got in the way of spreading my legs and my tube top and my skin was all sticky with cum. Thankfully, I wouldn’t be wearing any of this much longer. Their watching eyes so aroused my slutty nature. I took off my tube top and skirt leaving my fishnets and six inch heels. I also wore a black thong and...Read On