Gay Cry Stories

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Ultimate Losers: Billy

by hasnoalias on Aug 17, 2017
Gay Male

*All characters in this story are above the age of 18 years old* *This story was inspired by and written with the permission of redbeardedsf. The characters and situations involved are from his story "The Ultimate American Boy Contest." He is a writer of excellent slave boy erotic fiction. If you are Nifty enough you can read his stories, and get a better u...

A Kept Sissy Boy

by keptsissy on Sep 19, 2017
Gay Male

"You need your butt paddled, don't you?" When I responded to his 'Dominant Male' ad I knew what I wanted, what I might be in for. I masturbate to nothing other than being used by a real man. But I didn't know this man would exploit that completely at the time, be as good at it, as addictive as he is, make me his full time sissy 'girl'. It started out two...

Little Sex Toy Ch. 05

by keptsissy on Sep 26, 2017
Gay Male

I'm squatting in the middle of his cold cement basement floor, just over the drain in his laundry room, sitting back on my high heels. The 4" spike heels he insists I wear now around the house, wobble in them and get whipped for it, walking or squatting. He says a 'lady-like' little bitch should know how to wear high heel shoes. Leather, padded restraints...

Valentine's Day for Me

by koksocker333 on Mar 18, 2020
Gay Male

This day is not a happy day for everyone, for some it's a reminder of a love long gone, an ex who hurt you. A day that you will not be receiving flowers, or some silly card, for some of us it only causes pain, reminds of of a love that is gone, one that should have been with us forever, but will always be in our hearts. Forever is an amazing word, for so fe...

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,...

Technical Difficulties Episode 05

by LucyH on Sep 14, 2017
Gay Male

Seeing Ryan holding handcuffs made Zach's brain buzz and his heart race. "Thanks, but you can keep them." He glanced back up at the T.V. screen, feigning interest in the warm front that was moving across the country. Ryan hung the toy on the handlebar of Zach's exercise bike and stood beside him. "Are you okay?" "No." He dried his sweaty palms on his pant...

Cobalt Blue Ch. 13

by Pelaam on Sep 26, 2017
Gay Male

Chapter 13: Sex, Lovers and Videotapes Pelaam, September 2007. Stewie's birthday had already passed a few days earlier and he'd been more than pleased with the multitude of gifts from his fiancé. He'd received jewellery, clothing, books, as well as vouchers to spend as he wished. However, Jaze had promised a final gift, in a voice that dripped with dark pa...

I Visit the Roman Baths

by sabb on Aug 18, 2017
Gay Male

My friend had invited me to join him in the baths. I knew this was a custom of his people and that everyone, men and women, went to the public baths to bathe and talk. And I well knew that much of the mens talk was business. As I wished to do business with his people I accepted his invitation. But I accepted it with some nervousness as I had heard stories of...

My Dark Angel Ch. 04

by Prettyrock on Sep 14, 2017
Gay Male

Ethan My life hasn't been easy. I've always been afraid. Of everything. Afraid to take a risk. Afraid of relationships and of failure. And God did I fail. I admit it. I didn't fail to save those people. Yet. I remembered my dad told me "real men don't cry". Maybe I'm not a real man after all. Have you ever felt so empty, so broken that no matter if you wa...

The New Kid Next Door Pt. 07

by koksocker333 on Jul 14, 2020
Gay Male

I made dinner while Ryan set the table, we would have a sit down dinner for a change, he even put out candles, wine glasses, the whole nine yards to bad we were only having burgers, I decided to make a salad to go with the burgers, Ryan helped me chop up veggies to put in the salad, I put on shorts to go cook the burgers, Ryan gave me a funny look. "Ryan I...