Cuckolded Crossdresser Pics Stories

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Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

Forced Gay by Two Women

by fun4all6969 on Sep 11, 2017
Fetish

I told Nikki about an upcoming business trip to the Las Vegas area, and how I'd be interested in meeting with her for a strap-on and simulated forced bi session and that I would be willing to be generous. Nikki started out with one dollar figure, which then increased she said, because Jenny her friend wanted to play too. Then when I asked about rules, she sa...

How I was Forced Out of the Closet

by gtanya on Apr 4, 2018
Transsexuals & Crossdressers

I was again dreaming of the night I would lose my anal virginity. It had been such a constant since last 3 weeks. I had been talking to a beautiful CD named Rachel since last 6 months and with the thought of meeting her in person, I had planned a vacation to China where she was living. The only problem that I had here was I was going to be on the vacation wi...

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

One of My Favorite One-Offs

by slaveheathen on Nov 27, 2017
Fetish

This is a true story about one of my favorite one-off CL hookups. I had posted an ad, this being back when CL was still actually useful instead of the joke it is today. I mean, seriously, what's with all the time wasters these days? Anyway, I posted the ad; "non-passable crossdresser submissive, I suck cock, eat ass, love getting ass fucked, do ATM, swallo...

How It Began

by DarlenesToy on Jan 1, 2019
Loving Wives

Looking back, the seeds were planted early. In high school, I had been popular and always dated really good-looking girls. Marsha worked at a drug store in my neighborhood, she was awkward looking, but with a great personality. She was fun. The first time she asked me to take her home, I had her top off in the car and we made out, it was so hot. By the fou...

Secret Journey Ch. 02

by DrGonzo124 on Feb 11, 2019
Transgender & Crossdressers

AN: with profound thanks to Personal Deviant. 8 9 8 Suki dreamed of another time and place. A place filled with warriors drinking... feasting...fucking. Another body? His, yet not his own, to judge by the nipple clamps pinching him with a painfully arousing agony and the odd sensation along the length of his erect shaft that had to be a lattice of pie...

Teri's Second Man

by tericd on Sep 12, 2017
Transsexuals & Crossdressers

I met Brian when I put an ad on the Squirt network. I put a picture of myself from the neck down in blue lingerie, saying a crossdresser wanted a man. Brian answered my ad, saying he had a fat, cut, 8 inch cock. Obviously this got my attention. After a few emails he told me where I could see some pics of him. After I saw them, I was hooked. He was wearing p...

A Change is Gonna Come Pt. 02

by Deviana on Apr 6, 2020
Transgender & Crossdressers

"Hon, you don't mind that I'm going out, do you?" she asked. There was only one answer to reply. --------- continuation ------------ "Well, no", I said. Not sure if she or I knew if I meant I didn't mind that she was going out, or that I didn't want her to go, that I would rush to my book of spells to cancel what I had started. But she gave me no choice an...