Transgender & Crossdressers
(This story is a follow up to my story 'Pizza Delivery')
***
Dear Internet,
It had been a few weeks since my encounter with, as I like to call him, Pizza Daddy and I was looking for a new adventure. I briefly thought about cruising the local parks at night or finding a glory hole somewhere (giving, not receiving, of course) but Pizza Daddy's warning about...
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by
BlueSkiesRedEyes
on Oct 20, 2020
Transgender & Crossdressers
Katie reached forward to grab the bottle before hesitantly giving it a spin. She had a nervous feeling in the pit of her stomach this time—so far everything had been innocent enough but now people were starting to get drunk and she knew people were ready to start testing the boundaries.
I'll be fine as long as it doesn't land on Mark. She thought to herself...
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by
Angelscuck
on Sep 2, 2017
Exhibitionist & Voyeur
Well the weekend had arrived. My Fiancé, Angel, had given me a complete makeover at the salon. I looked ridiculous in my maid's costume with full makeup, heels, stockings, garter belt and leach with collar.
She looked amazing with her slutty makeup, hair worn up and completely naked under her trench coat. We were on our way to her gangbang. Her black maste...
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by
TheGentleGuy
on Sep 16, 2017
Transsexuals & Crossdressers
It all started when my friend and I went to the bar. His wife and my girlfriend were both out of town so we decided to have a boy's night out. We were having a good time and both of us were pretty drunk. There was this beautiful woman with the nicest ass I ever seen. Tom and I both noticed and had a hard time not staring at her. Tom made a comment about how...
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by
johnjinglez1
on Jun 6, 2018
Transsexuals & Crossdressers
This is a continuation of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real.
***
After my first three encounters with TS and CD's left me feeling unfulfilled I gave it up for a few months and figured it just wasn't for me; I went back to having sex with...
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by
dani_boi
on Sep 12, 2017
Transsexuals & Crossdressers
I was heading to a club and got my 5'7" 140 lbs skinny sexy body all dolled up. I love to dress up and look like a hot woman since I have to spend my week as a boring man. I do compensate by having my ears, nipples, belly and tongue pierced. Ok it's more like I dress like a slut. I had on black thigh high stockings under my black leather thigh high boots wit...
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by
FantasizeAndRealize
on Sep 17, 2017
Mature
This time I only waited two days to make it back to Mrs. Mattenhausen's house.
I rang the doorbell and she called for me to enter. Once inside I was shocked to see that Mrs. Mattenhausen was not alone. There was an older man with her. Not as old as she was. I calculated Mrs. Mattenhausen to be about 64 years old but he was at least in his mid fifties.
"Ric...
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by
SilverDrake
on Sep 16, 2017
Transsexuals & Crossdressers
There are some memories in life that you can never shake. No matter what. And the third time I awoke, bound and unable to move, was one of these times.
This time, I was sitting in a different room. The mechanical whoosh whoosh was gone, replaced by classical music playing softly over invisible speakers. At first I thought the room was the same room, all whi...
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by
Goldeniangel
on Sep 12, 2017
Anal
Over the period of a couple weeks, Alex got a little bored with fingering his ass while he jerked off... although it still felt good, it was often lacking that feeling of a painfully pleasurable stretch. If he left his ass alone for a couple of days then it would tighten up again, but in lieu of having anyone else's ass to plunder he enjoyed being able to pl...
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by
sparktj
on Sep 11, 2017
Mature
I'm a 53yo bi guy in the UK. About 4 yrs ago I arranged my first MMF meet with a couple, Lesley & Adrian from Birmingham. She was lovely, looked like a mum you'd see at the school gate, dark hair, gorgeous brown eyes and nice legs, cuddly figure but not fat. They lived in a small terraced house in the suburbs and I loved turning up there on a Saturday mornin...
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