Gay Straight To Sissy Stories

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Infinite Scroll

Little Sex Toy Ch. 07

by keptsissy on Sep 26, 2017
Gay Male

The cum all over my face mixes with the tear smeared eye makeup. It's running down my cheeks. It's in my hair, on my neck, I'm covered with cum. The first man that came in my face came huge. He choked me too, deep throat fucked me and made me cry. I've been crying and tearing up ever since. That was three hours ago. He had very large spurts that soaked me,...

Drunk Friend to Sissy Slut

by olybiguy27 on Sep 14, 2017
Gay Male

What follows is the completely true story of the weekend that changed my life. This really happened to me and took place in the summer of 2008 just after graduating from high school. My name is Andrew and I was a major stoner in school. I had a lot of friends, mostly due to the fact I always had really great weed that I would get from my rich old neighbor...

Andre Finds Love Pt. 03

by eviltwin52 on Aug 18, 2017
Gay Male

See chapter 2 where my father-in-law fucks me while my wife is away on our honeymoon with her black lover. For those of you who wanted to know what happened to joanie in the final chapter of "It Could Be Worse", the mystery is solved. ***** Part 3: Tomorrow, I thought to myself happily. Lee Anne will be back tomorrow. And her black lover, Leshaun. I...

Special Inducements

by bjmichaels on May 1, 2018
Gay Male

I was reluctant, but my ex-boyfriend Brian talked me into going to his younger brothers graduation pool party. We were sitting in my car in the parking lot of the liquor store. He had bought two kegs of beer and I helped load them in the car. "Why should I torture myself staring at all those eighteen year-old hard bodies?" I jokingly asked him. "Because yo...

A Very Dirty Little Sissy 'Girl'

by keptsissy on Aug 31, 2017
Gay Male

I love to please my boyfriend. I masturbate thinking about that. A lot. To hear him when he's in me, on top of me, lost to my tight little hole or my mouth, I love the sound of him, the 'man' noises he makes! But as much as I like to please him, I just like to please men. Do I ever. I've been at it since just after high school. And there is nothing hotter th...

Guys' Retreat Pt. 05

by Cyanlot on Apr 21, 2020
Gay Male

Part 5: Brianna's Training "Vince had a terrific idea, Brianna," Kent said. "It's really going to make this easier for you." "Yeah," I said, noncommittally, knowing full well that whatever Vince had come up with wasn't going to be to my benefit, though I was sure it would benefit them. "Yeah. We've been downloading some videos for you to watch. You're goi...

"You Go First" (Ch. 10)

by donaldelliott11 on Mar 2, 2020
Gay Male

This is the 10th in a series. "Samantha" was the 3rd chapter and "Donnie" was the 4th. I regret that my inconsistent use of titles prevents Lit from properly displaying the series. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help authors improve their writing; star rating...

PIXIE Sissy Stripper Ch. 01

by EROTICbearscribe on Dec 24, 2019
Gay Male

The imposing shadow loomed over Benji blocking out the lights from the stage. "I asked you a question," a deep voice said. There were no other sounds in the club. The loud dance music had been turned off a while ago. There was only the clinking of dishes coming from the kitchen. 20 year old college student Benji knew someone was speaking to him, but the...

Beauty and the Beast Pt. 03

by Suzzique on Jun 3, 2019
Gay Male

"Well, well!" said Daddy in a tone of mock surprise, "Your Uncle Ted has made it here after all. And for once he's timed it just right." "You promised," I cried out, on the edge of tears again. "I lied, you dumb sissy. I lied." He laughed. "Cut the jokes, Jack. Give me the bitch. I've come a long way to get my cock up the little slut. I want her now." "...

How Did This Happen to Me?

by bjmichaels on Dec 12, 2018
Gay Male

I live in a very expensive condo in one of the most exclusive and prestigious buildings in town. Most of my neighbors are very wealthy retirees. They generally purchase their condo's with cash. I have a five-year plan where my condo will not only be paid off in full, but I will also have a net worth in seven-figures -- yes, you heard me right -- I am thirty...