Gay Sissy Bet Stories

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Daytime Fun between Tim and Bill

by Hawkeye1981 on Mar 13, 2018
Gay Male

Tim got home from work. He called out to his mom. "Mom!" No answer. He walked into the kitchen and saw a note. "Tim I'm going out after work I will be home later. Hope your day was good... Mom" Tim smiled thinking about lunch with Bill. He still felt the fire in his stomach for him. Tim changed into some shorts and wandered to his moms room. His feet...

Down The Path Ch. 02

by gbr2004 on Sep 14, 2017
Gay Male

Next chapter in my story of my domination by a stranger I met online. * I waited to hear from him again. At first, I didn't know if I really wanted to get together again. The first time we met, at times it was a little more intense than I was looking for. After a few days I couldn't get him out of my mind. I couldn't believe how badly I wanted him to call...

30-Days of House Arrest Ch. 02

by bjmichaels on Dec 4, 2017
Gay Male

It was hard to concentrate on washing the breakfast dishes and cleaning the kitchen. Mister G was in one of his playful moods and couldn't seem to keep his hands off me. He massaged my shoulders and back and occasionally a hand would slip beneath the waistband of my shorts and claim possession of a buttock, squeezing and pinching it. Needless to say, I wou...

The Poker Master

by MixMasterFlex on May 1, 2018
Gay Male

So I had a friend named Reshawn in college who also had a serious obsession with poker. We played obsessively, convincing our friends to join us for a game in our dorm whenever we could. When we couldn't get a game in person, we would play online, share stories over IM, and sometimes trade money on the various sites. One day Reshawn had asked to play on my...

That's My Good Boy

by Submissivegoodboy on Sep 21, 2020
Gay Male

Bethany and I arrived at the hotel early that morning. We spend the day talking, snuggling, kissing, giggling and getting ready. Around midday I go into the bathroom and shave my body, we want me to feel extra sexy and feminine for my first time with another man. Mmmm as I come out naked and smooth Bethany giggles and jumps up and runs over to me. After sl...

Research Pt. 02

by eviltwin52 on Aug 18, 2017
Gay Male

Please read Research part one first. ***** "So in summation I submit that although a certain portion of the male population engages in homosexual acts, they aren't homosexual at all. No, they are under-endowed males who wish they could have heterosexual relationships but whom women shun. Through aggressive parenting, peer pressure, and social activities th...

Old Jack Ch. 03

by exaucer on Sep 14, 2017
Gay Male

I must have dozed off for a while but awoke to the sound of running water. The little, see through, black panties were sticking to my knees. I realized that Jack was in the bathroom and sure enough, he emerged a few seconds later smiling in my direction and carrying a smallish jar of some kind, in his left hand. He set the jar on the bedside table. It had a...

Party with Wife and Her Lover

by colleenslittletoy on Sep 14, 2017
Gay Male

My girlfriend of six months came home all excited. This was a good sign I thought because I was afraid things had been getting a little dull lately. It seemed like she wasn't really into our lovemaking sessions and they were getting fewer and fewer. "I need your help!" she exclaimed when I asked her why she was so excited. "There is an important business di...

House Rules Ch. 07

by EROTICbearscribe on Aug 7, 2019
Gay Male

WALKING THE WALK "We're going to have a visitor today," Daddy announced during breakfast one morning. He was wearing a suit because he had a business meeting. He looked very sharp. My daddy was so handsome. I was such a lucky sissy. When I asked him who was coming, he told me it was Miss Marguerite. "Miss Marguerite from The Beauty Mark?" I asked. L...

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...