Gay Cuckold Stories

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How I Met My Husband

by jessymichelle on Sep 18, 2017
Transsexuals & Crossdressers

Tim was a cute boy in a nerdy kind of way. Beautiful smile, though. He was about 5'9, dirty blond, skinny, kind of dorky, kind of messy, but a good guy and a better friend. I was only a bit shorter than him, but even skinnier, leaner, and tan from every morning I spent swimming for an hour. Being both college freshmen when we first met, we helped each other...

A Cheating Wife's Disclosures Ch. 03

by Krystal0690 on Sep 12, 2017
Loving Wives

It was 9 PM on a cold Tuesday night and I was sitting at a bar on the other side of town. I had a date set up with a married man I'd first met online. It wasn't really so much a date, as it was a quick get together for sex. We've had sex twice before and most likely this will be our last encounter. I was no longer looking for a relationship or an emotional c...

A Job in the Theatre Ch. 05

by BothWorld on Sep 13, 2017
Transsexuals & Crossdressers

Chapter 5 - Day two with the cast... The next morning Paula awoke very aroused. Sleeping in the satin gown all night had kept him hard and throbbing for the entire night. This was now the third night in a row. He quickly removed his throbbing cock and stroked furiously. He came less than a minute later. He wiped himself clean with a tissue and let out a dee...

Anal Sex with Stranger on a Train 01

by SusanJillParker on Sep 19, 2017
Anal

Anal Sex with Stranger on a Train 1 On the way home from work, a man anally molests a stranger on a crowded commuter train. Having been riding this train for years, Peter rode this commuter train every day, twice a day to and from work home. In all the years, never has he ever seen the train as crowded. With nowhere to put them, the train was so crowded...

14 Inch James - Undercover Cop Ch. 01

by heavenlyKK on Sep 25, 2017
Exhibitionist & Voyeur

At this point in his life James had come to accept that he had an enormously large cock; fourteen inches, when fully erect. Even when flaccid it hung down about ten inches, with a massive, thick shaft and bulging cock head. It had been both a blessing and a curse. As a teenager James was embarrassed by it, especially since he was on his college swim team. It...

Making a Whore

by dna27fog on Sep 12, 2017
Group Sex

Heather was a slut when we met. I didn't know it when we met, but it didn't take long to figure it out and once I did it didn't take long until we were fucking. There were two obstacles for our relationship; my wife and her boyfriend. I was 44 and she was 20. I was an average looking guy, but at 44 looked more in my early thirties. She was 20 and looked 20,...

Becoming Elizabeth Ch. 05

by bottomsatx on Sep 19, 2017
Transsexuals & Crossdressers

Author's note: Some of the sexual behavior chronicled here is patently unsafe. I really hope that the story makes your dick hard (or pussy wet, for my gentle female readers), but use some sanity when you're out in real life. As usual, there's truth mixed with fiction, but mostly fiction. And much thanks to Leopold for editing! Chapter 5: Back Home The nex...

The Blackmailed Sissy

by jmanrules on Sep 13, 2017
Transsexuals & Crossdressers

Jon walked into his roommates bedroom looking for the phone charger he loaned Eric the night before. As Jon was looking around he saw several pairs of panties, bras, and pantyhose. Not thinking anything of it Jon just grabbed his charger and left with it in hand. After he sat down it dawned on him that Eric has never brought a girl over and even if he did th...

A Journey of Discovery Ch. 03

by Ivonificood on Sep 15, 2017
Group Sex

Reading over the events I have written down, I developed a raging hard on and had to make slow love to my own cock. I must apologize at this point because in the beginning, I failed to admonish you to practice safe sex. At the time of the telling of this story, aids had not become the catastrophe it is today and std's were curable by a shot of penicillin....

Anything for Chocolate - A Prequel

by AlinaX on Jun 18, 2019
Transgender & Crossdressers

For the third day in a row, there was a gift left on the door mat, waiting to ruin my day in an increasingly fantastical manner. I stared down at the little wooden box, tempted to smash it under my foot, squashing the contents and rendering the inevitable note within unreadable. The moment passed, however, and with a sense of weary resignation I picked it u...