Gay Sissy Whore Stories

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Roommate Turned Me Out

by ralphcollant on Nov 2, 2020
Gay Male

It was a typical Tuesday afternoon after my last class for the day. I walked into my dorm room and found my roommate, Mike, watching porn on his laptop. This was not unusual for either one of us. Some of this junk could be quite entertaining. He nodded and said "Hey Tim" as I walked in and then waved me over so I could see what he was viewing. It was some pr...

Sissy Dream Come True

by Sjen451 on Oct 6, 2020
Gay Male

It was Friday and I had one job left before I could start my weekend. I didn't have much planned other than watching some of my favorite sissy porn and playing with a few of my larger dildos. Not too exciting, but it's how I spend most of my weekends when I don't have other plans. Today I wore my red lace panties under a pair of black break-away running pa...

Discovering My Slut-Side Pt. 02

by i_like_it_like_that on Dec 10, 2018
Gay Male

With Danielle's fingers and mouth off my ass, I knew what was coming. Not being able to cum made me incredibly horny. I was ready for release and wanted Andrew's cock inside of my warm hole. I stared at his dick with a look of lust and got lost of the moment. I was brought back to reality by Andrew slapping my face with his veiny shaft. "You ready for this...

Brother/Sister/Slave

by brownmonkk on Aug 18, 2017
Gay Male

Brother / "Sister" " TML", November. 1970 A Monk's monk or two virgins in the monastery; "Good loving & Good Scourging "Sissy" does her magic. WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow brother monk in the monastery. It was great. I was a 20-year-old virgin and had fantasized about lots of women. I distinctly remember...

Tim's Life Pt. 02

by Seamen on Aug 18, 2017
Gay Male

Tim stepped into the shower and turned on the shower. He jumped as the cold water hit his body, and then squirmed as the water ran down his hairless chest down to his balls and off his legs. He always kept himself smooth and hairless all over. It made him feel better about himself, and it aroused him, as well as the men he slept with to no end. He put his he...

Awakening

by up4anything0849 on Jul 3, 2019
Gay Male

The building that I work in has a gym that's available to use. So in an effort to get in better shape I had decided rather than sitting down at my desk for lunch I would hit the gym. It's not like I'm in terrible shape, I just needed to lose a few pounds off my 5'10, 175lb body. The great thing about this gym was that it was hardly ever used by anyone. I c...

Becoming a Gay Fuck Toy

by Want2BUsed on Aug 31, 2017
Gay Male

It was towards the end of my shift and after seven hours of staying away from the bathroom, I had to pee. I asked a fellow server to watch my tables and excused myself to go to the bathroom. I hate using the employee bathroom since that's where everyone goes to smoke, and I don't smoke. I decided to use the handicap facility. It's a single room and since I w...

Feminized by My Father

by YANKEE DAN on Aug 30, 2017
Gay Male

I opened my eyes, blinked, yawned, closed them again. I felt confused, disoriented in a way that was... strange. It wasn't like waking up was supposed to be, I wasn't half asleep. I can't remember getting in the bed, in fact I can't remember the last thing I remember. Where did consciousness end last? I was clueless. I tired to move my body and I found it...

The Hanky Code Pt. 15

by His_fag_wife on Sep 14, 2017
Gay Male

Mistress Caprice stood in front of me and looked deep into my glazed eyes, as I rocked up and down on my rubber cock. "I had to pay a pretty penny for you bitch, after so many people had watched some of your more extreme videos. A lot of very depraved people could see just how much use you might be." "But I wanted you before your inevitable trip to the far...

Sissy Bottom Has a Nite Out

by lostsoul1974 on Sep 14, 2017
Gay Male

My wife had gone out of town on a weekend business trip, so I invited my Fuck-buddy Eric over for some fun. I met Eric a couple years ago when he passed me his business card through a Glory Hole after he had fucked my asshole raw. After I eventually called him, we hit it off and have been friends ever since. Of course, hot raunchy sex can really help cement...