Wednesday , June 16 2021

Tag Archives: crossdress

A story about crossdressing – his is the beginning of a series of episodes about poor Charles who ultimately loses all his male attributes

It all began with a letter Charles received on Friday after being home ill for a week with an undiagnosed lower abdominal disturbance. I had a nice chat with your wife Paula, the other day. We both agreed that you need a new direction in your life to help you stop playing this silly role-swapping game. She tells me that she has once again caught you attempting to wear some …

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A man plays around with cross-dressing because his pretty sister-in-law persuades him

“Well you know why Lisa dropped Paul?” It was my sister-in-law, Susan offering me a tidbit from my wife, Lisa’s past. The three of us were eating dinner one evening and we had had a few beers. “Susan!” Lisa said it almost as a whine. She looked alarmed. Naturally I was intrigued. “Paul wanted to do it with Lisa with himself dressed up as a woman!” I giggled, but stifled …

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The Lost Boy part 21

Three Days Later: Den Mother’s Roadhouse Ian’s hands lay palm down on the Urul’s chest, resting on her large mammaries as he bounced up and down on her pelvis. Her red, veiny, canine cock rapidly pumping into his ass and two plump balls slapping the jiggling flesh with each upward hump. “Ugggh fuck…yeah boy! Ooohh…ride me…ride this doggy cock!” She encouraged from beneath him. He was squatting over her body, …

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A young man tries on his mother’s panties

I awoke midmorning on that summer day. I was instantly shaken from my morning daze when I remembered what I was intending to do. The opportunity had finally presented itself. My hard, dripping cock formed a tent in my pajama pants as I hurried out of bed. I had come home from college over the summer. I was taking summer classes at a local school, but there were no classes …

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A story about transformation, cross-dressing and bondage

There she was. “Come in Brenda!” Glen Simmons absently shouted. Brenda Porter, the freshman girl who had freaked out at her bus stop shyly entered the room. Glen wondered why he didn’t remember her from the junior high school, then remembered this was the transfer student who had just started at Bentson High. He pointed to the seat, which she took, careful to keep the hem of her red spandex …

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A man-pretty husband is controlled by his wife into dressing up as a woman and taking a male lover

I couldn’t believe that Susan, my wife of two and a half years would really do this to me. Yet here I sat in the back seat of our Olds wearing a short blue satin cocktail dress. The slinky skirt kept riding up my smoothly shaven, nylon-clad thighs to display a provocative glimpse of pretty pink lace. Susan had insisted that I dress for the costume party from the skin …

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My wife finally caught on to my panty fetish and won’t have sex with me unless I wear her well worn panties on my head

I’ve been married about a year now and I just love my wife Amanda. I married her because she wore the sexiest panties I have ever seen a women wear. But I tried not to tell my young bride just why I married her. Sure she has a killer body but her sheer panties just drove me nuts! I just couldn’t keep myself out of her panty drawer or the …

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My story is about the start of my transition to a woman, and finding the perfect guy

This story started a couple of years ago, or should I say it all started 40 years ago when I was young. It seems I have always enjoyed dressing in women’s clothes. I have been a closet cross dresser for most of my life, starting with dressing in my mother’s, sister’s, aunts, friends, etc. underwear then my wife’s and at any opportunity pinching other women’s underwear when the opportunity arose, …

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Long sex story – I Was A Reluctant Shemale

Marilee’s fists tightened in despair as she sat at her secretarial desk and listened to the muffled moans emanating from the office of her boss, JC Wyatt. JC was one of the youngest and most famous casting agents in Hollywood and was the most blatant offender of the “casting couch” which degraded women. The young actress, a stunning blonde who couldn’t have been more than sixteen years old, had looked …

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How I Became A Cross Dressed Dominatrix

Trying to find some action in a little bible-belt town in the South turned out to be a bite. In the end though, it was well worth the wait. I had been here for almost a year as I cruised just about everywhere a hot cock looking for a blowjob would hang waiting for a cocksucker. Then my journey came to an end at a park I never found before. …

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Forced to Cross Dress on Halloween

I could tell he was anxious. Informing him about the Halloween party raised a lot of questions on his end which I skillfully either ignored or diverted. I had not been mean right from the start, but I clearly told him he had 3 chances to come up with a suitable Halloween outfit idea. If he failed, I would choose for him. That was our deal. My partner, thinking he …

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Straight guy gets talked into

I was introduced to cross dressing when I was about 18. I was picked up by a local divorcee who was sex mad. After I finished shagging her on her bed and was having a break before having another go, she opened a drawer in her room and pulled out a dark pink camisole top. I thought she was going to change into it but instead pulled me up to …

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One of our male authors tries out cross-dressing and water-sports for the first time

Today something happened that I have always wanted for twenty years. A good friend from the Internet had provided me with a true gift of friendship. She had spent some time looking for the exact thing I wanted, then bought it, tried it, used it herself, and finally mailed it over the ocean to me. What was it precisely! She had bought me a true, original, real-world “normal” short skirt. …

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