Gay Sissy Stories

27,439 results
Orientation
Length
Source
Infinite Scroll

Adam & Mike: The Story Continues

by mikeman341 on Sep 17, 2017
Loving Wives

(This is the continuing story of Mike and Adam, best friends who had suddenly discovered their new found sexual attraction to one another. They have had a couple of rounds of hot sex together, including a mutual jack job on the golf course. They are now headed home to cyber chat with their families. The first installments in the story are under the gay/bi se...

First Male Massage

by maxfuckedher on Sep 14, 2017
First Time

My back had been giving me problems for some time and it had been a while since my last massage. I did not have a regular massage schedule partly due to the cost but also because I really didn't get any long term benefit. I decided to look for a new masseuse on the internet and found one near home, one that offered a firmer more therapeutic massage. Further...

Dark Angel Ch. 01: The Meeting

by ReiverToo on Sep 12, 2017
Transsexuals & Crossdressers

It was after 10:30 pm when my Japanese business associates had finally had enough sake and karaoke to call it a night. Maybe they were just off to see if they could score some company for the rest of the evening. Who knew? They were all on huge expense accounts, so buying a girl (or boy) for the night was not a financial problem. Some had even offered to inc...

New Mother, New Life Pt. 01

by Cara_Elaine on Sep 13, 2017
Transsexuals & Crossdressers

When I was born I was immediately given up for adoption. I was what was known as a 'Magdalene baby', a product of 20th century catholic Ireland where women who conceived out of wedlock were sent to a convent to give birth and work like a slave in the laundry as penance for their 'sin'. The church made life cruel for these women and to make things worse most...

Creampie Cuckold Humiliation

by cuckcreampielover on Sep 25, 2017
Loving Wives

I have been married to my wife for just over 4 years. She's perfect. I met her just out of high school and she was a suppressed, hot and horny church girl. I was the first boyfriend she ever had so needless to say she was a virgin. We got married after a couple years of dating. The sex was great. After a while, the sex was still great but my wife didn't se...

Life Renewed Ch. 02

by WF06 on Sep 18, 2017
Romance

A NEW LIFE FOR JAMES AND ANA, PART II On the way home from town, something caught the pup's attention and he let out with a sort of "rowlf" sound and James asked him where that came from and named him "Rolf" on the spot. Also on the way back to the ranch, it started to snow lightly, then quickly building in intensity until by the time they reached the ranch...

Lori and Rick and Liz and Me Ch. 04

by ReedRichards on Sep 15, 2017
Anal

This is the fourth chapter of the story, but the story "While the Wives are Away," in the Gay Male section, falls in between Chapters 3 and 4. ***** It'd been almost six weeks since Liz and I had "gotten together" with Rich and Lori, and a couple of weeks since Rich and I had hooked up while Lori and Liz were away in New York. (See "While the Wives are Awa...

The Break Up

by BuckyDuckman on Sep 12, 2017
Fetish

Here's a short and fast one (under 3000 words) about trying to break up with Alicia until she wears a facial in public and changes my mind. I hope you enjoy! At nineteen, Shannon Marie Mitchell ruined me. I didn't know it at the time, but she fucked me up for years. It was the finals week, two days before we left the university for different sides of the st...

Teach Me Ch. 04

by betweenthesheets on Sep 13, 2017
Erotic Couplings

Chapter 4. You might want to read the first 3. This one is short. Longer ones are in waiting. Enjoy and thanks for reading. Sunday was a yell fest with my mom. Finally Monday came around and the school week started. I couldn't remember a time when I actually wanted to return to school after the weekend. I walked into class and sat at my seat. She winked...

The Cost of Silence

by neutrona on Sep 13, 2017
Erotic Couplings

The week had been stressful at work. An employee had been terminated and that had divided employees. Some figured the employee had deserved it and some thought that termination was like using a sledgehammer to kill a mosquito. Tensions were high but work was still happening. Dan saw Justin heading to the washroom and followed him in there. Within minutes, Ju...