Gay Sissy Stories

27,439 results
Orientation
Length
Source
Infinite Scroll

Aficionado Gets in Trouble Ch. 02

by His_fag_wife on Jun 12, 2019
Transgender & Crossdressers

Mark cleared the clothes from the table, he wanted a truly clear picture of Pete being used in the stockade, knowing he'd get some great footage for his website selling the stockade frames, it would help sell some more without giving away Pete's identity from the side view. But he'd also get some head on footage for posting on the internet should Pete fail t...

Sissy Pills Pt. 01

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

Some say it was some sort of experiment gone wrong. But it hit the streets and it changed everything. A pill a drug that you took that made you sexually submissive and made you especially sexually submissive to men. Semen made it worse apparently. And there were addicts that ended up not just being gay or fags but entirely sissies and that was fastly bec...

Trip to LA Pt. 02

by gbr2004 on Mar 3, 2020
Fetish

This story is just a figment of my imagination and shouldn't be read if you aren't into forced fem, sexual service and discipline. Otherwise, I hope you enjoy the story and I love to hear comments about my writing. *** All I can think about is how out of control this all is. Here I am, in LA, god knows where, dressed up in pink and white and looking like...

Alone with a Sissy

by JRussell on Sep 16, 2017
Fetish

Home alone with the wife conveniently out of town for the next four days, Mark wanted badly - badly - to act on his urges to be intimate with a man, to hug, kiss, touch, rub, stroke, suck, the whole progression of lovemaking. He was starting from scratch, as his gay friends also were his wife's friends and he didn't want to take a chance that a careless word...

From Husband to Man's Sissy Wife Ch. 03

by Pantypansy on Jul 15, 2019
Transgender & Crossdressers

'So how was it, sweetie,' Hamish asked me as I opened the door. I was still shivering with desire from licking up my wife's lover's cum off her huge, oiled tits in 'their' bedroom downstairs (actually my marital bed).. I felt a sudden wave of emotion, after being so overcome with desire to watch my wife's lover come all over her. I had helped him by pushing...

What Every Sissy Knows

by BelissimaSissy on Jul 31, 2018
Transsexuals & Crossdressers

Note: the following story is about 99% true with only minor embellishments. For example, there are no condoms in the story. In real life, protection is a must, but stories give us room to fantasize. Enjoy! ***** I was scared but it didn't matter. I pushed through it until my plump little dick poured out its hot seed onto my tummy. After that all I could he...

The Visitor Ch. 06

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

The shower when it came on surprised me, he had the shower head in his hand and played the spray up and down over my body, I blinked, recoiling in my shock and looked up at him, the shower gel squirted at me. "I like a clean sissy" I just hated that alien electronic voice so much, but I knelt there in front of him only too glad to be rid of the smell of hi...

Office Cumslut Ch. 01

by DrLuverotica on Sep 12, 2017
Loving Wives

FRIDAY MORNING "Are you going to work dressed like that Jo?" My wife was dressed in black, sexy high heels, black stockings with a pink 1920s style pencil line up the back of them, pink frilly satin panties (she hates thongs) and matching push up bra. "Yes I am hubby," she purred, as she pulled a navy blue, short pleated skirt over her hips. "Is there s...

Barbie's BBC Beginning

by jacki697 on Jun 9, 2020
Transgender & Crossdressers

I had always been curious about men. I had always wanted to experiment but alas I was way too scared of being "gay" to ever follow through on any of my urges. Chalk that one up to 18 years of living in a conservative Christian community. Instead I left my sexual urges to the alone time I had to indulge in my other fantasy of crossdressing. I loved the thrill...

Finally Found Her Ch. 02

by hyperpress on Aug 18, 2017
Fetish

Switching from "you" to "she" for effect. She moved from the vanity chair to the bed. I've covered the bed with pillows and the room is lit with candles. "You're such a good little girl, now go get us a bottle of wine," she is lovely on the bed. I'm standing at the bedside and your mouth is irresistible and I bend at the waste to kiss you. Softly we kiss a...