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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.

6

Toby's Story

Now this doesn't happen every day!

  I had been admiring myself in the full length mirror for the umpteenth time in the last hour, as girls like us do, when I heard a vehicle draw into the driveway. Under normal circumstances, this would not be cause for concern. But circumstances were far from normal. I was miles from my home, in my friend Annabelle's house, and fully dressed in her clothes, and caked in her cosmetics! ...Read On

5

My Mother's Boyfriend, My Slut! (part 2)

Now that he was my slut, I couldn't seem to get enough of him.

The day had been wonderful, seeing my slut skewered on my strap on. His nipples peeking through his netted shirt as he begged to come with me buried deep inside of him. After he came all over his chest and face, I had exited the room, needing my own release. I headed for the shower, happy to leave him to clean up his mess. With the taste of him still on my lips, I turned on the water....Read On

6

Fantasy Meets Reality at the Peep Show

A crossdresser's fantasy comes true

I pushed my way through the purple curtain to the cashier’s booth. He looked up from his newspaper and asked me how many tokens I wanted. I figured a stack of twenty would be enough to complete my mission. I’d been there several times before but this would be my first time taking things further. My heart was beating fast as I scooped up the tokens and made my way to the viewing room. As...Read On

5

Three nights in London, night 2, Irene is going out

Cute Tgirl goes out for the first time

"Irene,wake up sweetie." Slowly the mist from my dream started to lift. Irene, who's that? I slowly became aware that I was holding something soft and cuddly in my arms. A Teddy bear? I moved and felt something tugging at my chest. Breasts? I opened my eyes slowly and saw the broad smile of a pretty redhead just in front of my face. "Wake up, pretty girl." In a flash...Read On

4

A New Beginning (Part 3)

My first experience in public

It’s been a while since I’ve written. For background, I’ve got a wonderful relationship with my wife Joan and an ongoing affair with my step-daughter Ellen. It’s possible since Joan’s job keeps her out of town for extended periods of time. Both of the women in my life have the same sexual tastes and to say things get kinky is an understatement. Ellen was very much in dressing me up from...Read On

8

Jessie's Fantasy Chapter 7: The Tables Got Turned

Now that Jessie decided to turn the tables, how will she handle all of her friends?

Here I was, getting my boy pussy plowed by my good friend Scott, when Mark decides that he needs to call Jesse, the male me. As he was starting to dial my phone number I realized that I never turned the ringer to vibrate after we left the night club. I was panic stricken as they all knew the distinct ringtone that I used. I couldn’t let my phone blow my cover. I had to think fast, but what to...Read On

7

Seducer or Seducee?

Male attends a costume party as Tessa and is seduced by a beautiful woman.

Every year a city about an hour away from where I live hosts a big charity costume party that coincides with Mardi Gras. I had decided to attend the event as my female persona, Tessa. Since I don’t get many chances to go out in public I decided I was gong to go all out for this event. For the last two months I had been on a strict diet, more like starvation but I knew the results were going...Read On

2

My 2 AM Phone Call (Part Three)

I became a much better and more confident motel whore as the night wore on

Everyone seemed to be talking at the same time at my table, and I was surprised by that. I must have zoned out for a while because when I looked around, suddenly I was wide awake. I was now suspicious of what they gave me to drink earlier. As I look back, there was probably some sedative in it that caused me to doze off, but whatever they put in it, when I came around I was more alive and...Read On

7

The Incredible Mrs. Mac

My Mrs. Robinson

During my adolescence there were a few of my mom's friends that featured regularly in my lone periods of self gratification. None more so than Mrs. Mac. She was bottle blonde, attractive, with great legs, and magnificent breasts. She was the mother of three kids, two teenage girls, 15 and 13, and a boy of 7. Her husband Danny was one of my dad's work colleagues, and together they had earned...Read On

4

Three nights in London, night 3, Irene rocks!

Cute Dutch Tgirl goes for it

I woke up looking into the smiling face of a pretty redhead. Sunlight was streaming through the curtains of her bedroom. "Good morning, Irene," she said, and she kissed me on my nose. I smiled back and slowly remembered my adventures of yesterday. When I moved my legs it dawned on me that I was still fully dressed. I even had my high heeled boots on. My skimpy black dress was pulled up...Read On

2

My First Time Wearing Panties And Sucking A Dick!

My title says it all.

My realization about my wish to suck dick came pretty early on, around the time I was in college. I was comfortable with this and fortunately I went to a progressive liberal arts college where many different types of sexuality were welcomed and celebrated. Most importantly, I had a very open minded and kind room mate. Aside from being my room mate he was also a good friend and I had confided...Read On

3

My Good Friend Pete (Part 2)

In order to enjoy this story, I advise the reader to read "My Good Friend Pete."

From where I stood, I could hear the crunching of gravel under Pete's feet, as he made his way to the front door. I took half a dozen deep breaths, waiting for the doorbell to ring. I didn't have to wait long. "For fuck sake, pull yourself together man." I actually caught myself smiling in the wall mirror. "...or is it woman!" One of the most difficult things to achieve...Read On