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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.

58

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

30

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

20

The Day My Secret Was Discovered

My wife surprises me.

My wife and I have been happily married for four years. She is the dominant one in this marriage. Just recently I have discovered how much I enjoy wearing women's clothes. I love how the panties feel between my ass cheeks. The silkiness of the nylons on my legs as I slide them causes an erection every time.  My wife had no idea until one day when I had Friday off from work. As soon as she...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

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

12

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

Ready to Perform, Part Two – All Crossed Up

I get more than I bargained on!

Much happened in the next twelve months following that first session with my ex and her new partner: Ann began divorce proceedings which I didn’t contest, I financed myself into another home, and Ann, David and I met for two more sessions of torrid sex. These sessions were pretty much replays of the first; I would first screw Ann thoroughly through at least two climaxes, and then she would...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

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

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

Becoming Marie part 6 - At Master's

Going back to masters the first time

After leaving the toilets, we drove straight on to the Transporter bridge. We pulled onto the bridge and after stopping, he immediately got out of the car. I got out of the passenger side, while the rest of the cars loaded onto the bridge. He had already lit a cigarette, and he offered me one as well. I took it, thanking him. “So, what’s your name?” he asked. “Marcus,” I replied. ...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 13

Carla goes shopping and Vivien gets a surprise...

When I awoke the next morning, Hannah was already in the shower. I stripped off and joined her, and we kissed hungrily under the steaming water, our bodies sliding deliciously together. My hand slid between her smooth thighs, finding her aroused and ready. Slipping first one, then two and then three fingers inside her, I fingered her quickly to orgasm. She clung on to me as I continued to...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

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

35

Chrissy's First Black Cock

Chrissy gets fucked by a big black cock for the first time

  After I awoke from a deep slumber of a much needed nap, I laid there recounting memories from the night before with Todd. I got out of bed, walked to the kitchen and grabbed a soda from the fridge before sitting down on the sofa. As I sat down, a pain rippled through my ass, reminding me of the brutal fucking I had received from Todd. I sat there smoking a...Read On

32

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

32

A Little Naughty Fun When My Wife Is Away

A little wicked fun

When I was in high school, I always loved to dress in women’s clothes. The problem is I'm a guy. Whenever my mother was out, I'd always go into her room and try on her intimate apparel. I just loved how it felt on my skin. I'd especially liked how her bras and panties felt. I loved to get dressed in her dresses and even apply make-up. I really never told anybody about this. The lacier...Read On

58

A Night Out with Suzanne

Young man decides to support his new girlfriend's fetish and finds out a lot about who he really is

I hadn’t seen Suzanne in 15 years. She was a member at the country club where my father had worked and, despite living in separate towns, we saw each other every summer. We enjoyed each other’s company and we spent most of our days playing tennis and swimming at the pool. When I graduated from college and went into the Army, the thoughts of Suzanne were just faraway memories. Then,...Read On

28

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 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

26

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

119

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

59

The Change Up

Sexy outfit gets Deedra some lucky action

Finally a break comes my way. The children are off to college, the wife has to go out of the country for two months on business. I can’t remember the last time we had sex. She used to dress in all types of lingerie for me. It helped me suppress some of my crossdressing desires. That stopped and my crossdressing started to grow again. What an opportunity for me, I can change up and dress...Read On

46

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

42

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

24

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

24

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

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

22

The Feminisation of Michael. - Chapter 7

The Feminisation of Michael. Chapter 7 I settled in at Stanmore House quickly and Sam helped a lot and we would spend most days together with her showing me around the estate. I soon persuaded Sam to wear prettier things and we were often seen., me blonde, her brunette, rushing around giggling in little floral dresses. Alternatively we would ride the beautiful horses in...Read On