Caught Cross Dressing Stories

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High Heels and Stockings Tryout

by neon_noodle on Sep 11, 2017
Transsexuals & Crossdressers

High Heels and Stockings - First Time I blame Literotica, or credit it, as the case may be. I've always been excited by women's sex clothes -- high heels, stockings, panties, and skirts, and have shot lots of loads fantasying about how hot women look all dolled up. Then I came across Literotica, and started reading all the nasty, filthy stories about cross...

Lanceolina and Guinevar

by dantemendoza on Sep 1, 2017
Humor & Satire

6th Century A.D. Legend tells of the great Queen Arthuria who pulled, tugged, and yanked the great wizard Merlin's long sword out of his rocks proclaiming her as the first female monarch of England. Uniting all the neighboring borders into one huge kingdom, which she aptly named Cameltoe, Arthuria created the historical Knights of the Oblong Table. She ori...

Halloween Cross-Dressing Bash Ch. 04

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

"If I knew you a bit better, I'd tell you the other half of the story relating to the name of the shop and what my ex-husband tricked me to do, but it's a bit risqué and I'm embarrassed that I fell for it," she said with a sexy laugh. "I'm too trusting and it's only something that I would do. I should have known better," she said hanging his dress back on th...

Halloween Cross-Dressing Bash Ch. 08

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

She looked down and saw that he had an erection. "All you guys are the same," she said shooting him a cold stare. "Here I am pouring out my heart to you about what my ex-husband did to me and you have an erection." "Sorry." "Do you realize how humiliated I am to find out that I blew every man in my community? Then, to find out that I blew my husband's fo...

Dressing Up For My Wife

by dirtyjoe69 on Sep 13, 2017
Transsexuals & Crossdressers

My wife and I had a bet on the football game that pitted our two rival teams against each other. It was a horrendous day for my team and hers slaughtered mine 31-0. It was the same bet we always have with each other. It is a bet where no one really loses because it ends up with us having wild kinky sex. On earlier bets we have had, she has had to let me fuc...

Halloween Cross-Dressing Bash Ch. 02

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

Now, having given into the urge of wearing women's clothes, safe within the acceptance that he'd surely receive at the Happy Halloween Cross-Dressing Bash, he was excited about attending and getting dressed as a woman without being made to feel foolish or being harshly judged and meanly ridiculed. He just wanted to go somewhere that he could dress as a woman...

Yellow Polka Dot Bikini(s)

by PositiveThinker on Sep 14, 2017
Transsexuals & Crossdressers

"She was afraid to come out of the locker. She was as nervous as she could be. She was afraid to come out of the locker. She was afraid that somebody would see. Two, three, four, tell the people what she wore. It was an itsy, bitsy, teenie, weenie, yellow polka-dot bikini that she wore for the first time today. And itsy, bitsy, teenie, weenie, yellow polka-d...

Halloween Cross-Dressing Bash Ch. 03

by BOSTONFICTIONWRITER on Sep 16, 2017
Exhibitionist & Voyeur

She escorted him to the other side of the store and now that he was relaxed enough to take note of the woman who was helping him, he determined that they were both about the same size. She was pretty, much prettier than his wife. He felt better knowing that she could help him pick out the correct sizes he needed without making her think that the clothes were...

My "Uncle" Caught Me in Pantyhose! Pt. 01

by JHouston on Sep 12, 2017
Transsexuals & Crossdressers

"Rick, why are you wearing your mother's pantyhose?" Uncle Roberto asked me with a shocked expression on his face. I did not know he was in the house, I thought I was alone! It was morning on the second week of my summer vacation after graduating high school. My parents were both at work. My dad was a salesperson and traveled a lot. My mother was a school t...

Sarah Ch. 1

by Steve256 on Sep 16, 2017
Fetish

My sister and I had never had a calm relationship. She was my parents' favorite. Always pretty from an early age, she blossomed into a true beauty. By the time we reached high school (she's a year older than I), she was the most popular among the 'in' crowd. A champion cheerleader, with her classically beautiful face, long flowing brown hair, and perfect bod...