Gay Sissy Boi Stories

901 results
Orientation
Length
Source
Infinite Scroll

James Ch. 01: A Tindr Night Gone Wrong

by vanisland1983 on Sep 14, 2017
Gay Male

I would love to hear your input! Contact me through the contact tab on my profile. Story about a young man who is forced by another. I would warn you about it, but then, that's why you came here to read it you naughty boy... ***** This whole thing started when I broke up with my girlfriend. At the time, she had said I wasn't there sexually and emotionally...

How James and I Started Together

by CrossdresserAlison77 on Sep 16, 2017
Gay Male

It was a Friday night in southern California. I had been checking the Craigslist.com M4M section recently and found someone to respond too. After a long back and forth conversation, and a nervous wait, we finally met up. All he wanted to do was give me a blow job, but our night ended up going a little different. My name is Alin, and this was the first time I...

Jungle Fever Ch. 2

by ozeboi69 on Aug 31, 2017
Gay Male

I woke to the feel of sweat trickling run down my chest and my eyes flickered open to reveal the sun greeting a new day, it's warmth already noticeable. Had it all been a dream? I went to rise and found myself halted by invisible bonds. I couldn't move! Snapping to full consciousness, I looked down. Nothing. Just my moist body, sitting upright against a...

The Field Pt. 01

by Tsugaru3000 on Nov 26, 2019
Gay Male

"Be there in 10 minutes." The text said. Damn him. He knows it's a 35 minute walk. And he likes me to be ready and waiting. I took off my pants to remove my underwear and put my pants back on. I made the mistake of wearing them once. He tore them off and made me wear them around my neck all the way home. Thankfully no one saw. Shit, I better go. I fast wal...

Runner's Story Pt. 03

by booshakey on Aug 17, 2017
Gay Male

I woke up the next day and headed on to work. The image of Black Daaa, I mean, Terrence's dick sliding in and out of my mouth still haunted my memory. More disturbing was the fact I was getting an erection from it. I mean, I wasn't gay, not that Terrence cared, but after the past two visits I was definitely questioning it. Worked dragged on mainly because I...

Farm Boi Life Ch. 03

by Sungmehetu on Feb 6, 2018
Gay Male

Sorry for the long absence. As this was the most requested sequel, I made sure Ryan's adventure to be the first now that I have spare time to write again. ALL Characters are over 18. ***** I had to strip the sheets the following morning and found two slaves kneeling outside the bedroom door as I carried the damp, sticky bundle. "Alpha Chef, we will take...

Content Pt. 02

by Tsugaru3000 on Jan 23, 2019
Gay Male

He had left me there. There I was kneeling at attention in the middle of the room, hole plugged, and eyes covered by this hood. He had walked out of the room 10?...20?...30 minutes ago? I don't actually know. The shower water shut off. My mind began to race a bit thinking of the room I saw when I turned around to suck his cock. Just a glimpse. But I saw a s...

The PA's Interview Pt. 02

by 1suitedbi on Sep 14, 2017
Gay Male

PART 2 - INDUCTION You look up at me and clear your throat, "Yes Sir, I would very much like to take up the position as your PA, Sir." "Very good Gary, now I suggest you go through to my washroom and tidy yourself up." You quickly rise from my desk retrieve your suit and head for the washroom. I am on the phone when you return, I gesture you to take a sea...

Should Not Have Stopped

by pampersub on Aug 18, 2017
Gay Male

I had gotten a job in South New Jersey, not bad, right after law school. It took me awhile to clean out my old apartment so I did not get to leave on the road until Saturday morning. I was a little angry at myself for waiting so long, my plan was to get to a hotel on Friday night then check out the bar scene all Saturday and Sunday, pick a new place based...

How I Became a Sissy Pt. 01

by Yngwhiteboi on Jan 14, 2019
Gay Male

As a young man growing up I knew that I liked both men and women, but never had much success with either due to lack of confidence. Being only 5 foot tall and very small I had never been a hit sexually. To top it all off my shoe size was 5 in the UK. I was a rocker as well, which put off most people, shoulder length brown hair always in a pony tail, ripped j...