Gay Crossdresser Stories

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Orientation
Length
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Infinite Scroll

June Meets Dale

by june613 on Sep 14, 2017
Transsexuals & Crossdressers

I've been wearing Pantyhose for almost 30 years now, and I still have as strong a Fetish for them now, as I did back then. About 17 years ago I started meeting other Pantyhose Crossdressers or Pantyhose Lovers for Kinky sex. About 4 years ago I replied to a posting on Craig's List from someone looking for a Pantyhose Crossdressing partner. We met in stree...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

The Johnson Complex

by Januse on Sep 20, 2018
Erotic Couplings

At Samuel Ezra Xander University, a small, private, liberal arts college on the east coast there are several options for freshman living. One of these options is the Johnson Complex, and it’s considered the best place a freshman could live. Twelve buildings, Forty-Eight students per building, a lounge, every room has AC, and it’s in a great location on campu...

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The Basement Ch. 02

by FiveDots on Dec 24, 2019
Transgender & Crossdressers

I received a text the next evening. 'Hey dude, come down here and check this out.' Not yet ready to confront him with a revenge plan but not willing to ignore him either, I traveled down the stairs to the basement. My roommate had used the threat of exposing my questionable internet history to coerce me into letting him shrink me temporarily to pleasure him...

Finally a Princess Pt. 02

by fireandlace0533 on Sep 14, 2020
Transgender & Crossdressers

Part two of a crossdresser who loves Disney who has come out to his wife while on a Disney Cruise. New experiences and adventures are ahead. Finally a Princess (Part Two) I woke the next morning around six thirty which was a little late for me. I laid in bed and thought about what had happened yesterday. I had actually spent time in front of my wife Sarah...

Crossdressing Dad Takes on San Fran

by vikkihawe000 on Dec 24, 2019
Transgender & Crossdressers

*A bit different than my other stories, but shares some similarities. Let me know what you think. xx Vi ***** Kelly sat in a parked car in the San Fransisco Airport parking lot waiting for her father, Rod, to emerge from the terminal. Kelly loved her father and was glad he was visiting all the way from England, but she was not looking forward to him spendi...

Pantyhose and Cum Fetish Pt. 01

by OnTheKinkySide on Apr 3, 2019
Fetish

It was the summer and I had just finished my third year at College and I had turned 21 a few months earlier. I didn't want to get a job at the mall, well except maybe selling women's shoes or working at Victoria's Secret. You see I have a huge Pantyhose Fetish and not just seeing women in them but wearing them myself as well. I am not bi or gay nor do I co...

Sarah Visited an Adult Book Store

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

Since I've been reading the stories here, I've learnt a new acronym, ABS, Adult Book Store. Reading these stories has made me very curious to experience a glory hole myself. At a gay beach I had sucked off a complete stranger but an ABS sounded even more fun. I picked out the sleaziest, run down store I could find around here. I've bought books there befor...

Crossdresser Gets Found Out Ch. 02

by leathertanya on Sep 16, 2017
Transsexuals & Crossdressers

This story is fiction and is written for my pleasure and any comments or suggestions that anyone would like to make. Any suggestions email through the link below. I adore the feel of leather, rubber, pvc and anything silky so it was no surprise to me that at an early age I liked the feel of certain female clothing. I am a perfectly straight male but my fant...

Alex Struggles to Accept who He Is

by Shy_n_bi on Jul 29, 2019
Transgender & Crossdressers

Alex never thought he'd be living in this moment, a desire that he kept buried ‎deep within for his entire life and now a near reality! His eyes locked on her every move as his heart raced like he had never felt it race before and the battle between pleasure and guilt had all but began leading from his mind to the pit of his stomach! There he was, nervousl...