Crossdresser Get Gangbang And Cum Dump Stories

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Mary Becomes a Whore

by Juggerhead on Jul 30, 2019
Transgender & Crossdressers

Mark was like any other ordinary 25 year old guy with a regular 9-5 job as an office executive in an finance company. He was fair, around 5 feet five inch tall and had a slender frame. Often his friends and colleagues would ridicule him for his height and thing body. He had a boring life and didn't indulge in partying or clubbing. After his divorce he went o...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

After Hours Alicia Ch. 03

by NewAgeErotica on Sep 16, 2017
Group Sex

Alicia arrived at Peter's parents' house. She turned the truck off and cried for a moment. She loved Peter and couldn't imagine being with anyone else. He had always been there for her and was such a nice guy. She felt unnoticed by everyone in high school and college, but Peter made her feel like she was special. He actually noticed her. She knew that she h...

Fat Indian Crossdresser Slut Gangbang

by bottomgay on Sep 16, 2017
Transsexuals & Crossdressers

I am your typical sissy bottom guy who loves mature men. My proportions being large, club me into the BBW category so only the daring types can enslave me. Mature men in the age group 35-60 attract me. Only young guys with very huge dicks are an exception. This is about a naughty adventure of mine which happened in a residential area in New Delhi. The hormo...

It Started As A First Date

by spandexman on Aug 30, 2017
Fetish

As far as first dates were concerned, Roxy Fox, the 23-year-old, 5'11", Barbie doll faced gorgeous, secretary, with a strong dimpled chin, high cheekbones, big almond shaped hazel eyes, thick wavy shoulder length fiery-red hair, and a very firm, but extremely curvaceous 38FF-26-38 hourglass figure that her skintight white spandex pants, tight red spandex top...

Army Gangbang Duties

by slutluva on Jul 4, 2018
Group Sex

The evening started off as just a quiet dinner at a local pub, but it quickly escalated into a huge gangbang. This only occurred about three years ago, maybe a bit less. My wife Jordan and I have been heavily into the swingers/swapping/gangbang/orgy scene for a long time now. I guess you have to expect to run into people that you've either met at one of the...

Eric's Dreams Pt. 04

by Genevieve_Ohara on Sep 16, 2017
Transsexuals & Crossdressers

In the months following the Halloween party, Eric got a tremendous twitch in his dick and his ass simultaneously, whenever he thought about the gang bang. He never imagined such intense sexual pleasure could exist. That night, Genevieve had experienced multiple anal orgasms, as man after man rode her hard, and shot hot cum deep into her ass. And the waves of...

The Exploits of Cockslut Kelly 04

by CSK on Sep 11, 2017
Transsexuals & Crossdressers

Welcome back my glorious sexual angels. Thank you so much for the naughty feedback you've sent me. My, my, there are a lot of you that would love to have me as your personal fuck toy. I love the correspondence, so please keep it up. We left off last time with my roommate kicking me out of our room wearing the clothes of one of the co-eds that watched as he...

The Deviants' Room

by sissyrikki17 on Oct 14, 2017
Transsexuals & Crossdressers

Upstate New York, 2007 - Day 1 They all kept talking—bitching—about "sloppy seconds" but if you're drunk enough, and these guys were drunk most all the time, you don't really care about dipping your wick into a hole filled to overflowing with other guys' junk. You just stick it in, numbly hump for a few minutes, then make your own delirious contribution to...

Beth and Gretchen

by SoftBrie on Sep 19, 2017
Group Sex

For months I kept my adventure in Austin to myself. I thought about it all the time and considered doing it again, but it wasn't so easy to arrange. I would have to carve out time to go; if it wasn't a business trip, then money was also a factor. Although I got paid for my Austin appearance, it wasn't lavish enough to cover all expenses. I didn't share my s...