Gay Sissy Panties Stories

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Infinite Scroll

Rest Stop Management Pt. 04

by rimaday on Jun 3, 2019
Gay Male

Author's note: This story contains scenes of non-consensual or reluctant sex. I awoke to Big Daddy easing out the door and looked at the clock. It was just past midnight. I lay awake for a couple hours reliving the past few days, trying to figure out what it all meant. My marriage would never survive if my secrets got out. So much to lose and my mind kept...

Owned by a Ghetto Bitch Pt. 09

by FantasizeAndRealize on Aug 28, 2017
Gay Male

Tyrone moved into my apartment the next day. With his move in, drastic changes occurred to my life. These changes turned my financial, social and sexual world upside down. I go to work everyday and pay all of the bills on my apartment. Sholanda spends my paychecks to the last cent. I see all of the new things that she buys Tyrone. I barely have enough money...

Fun and Games Ch. 06

by jm02201960 on Sep 15, 2017
Gay Male

The next morning my ass, understandably, felt like it was on fire and I knew I had to give it at least a few days to calm down, which I did. The nearly nonstop sex I had recently enjoyed provided me with excellent visual images and the masturbation sessions were amazing. But taking on a cock anally at this point was unthinkable; my body was not used to it an...

Panties, Panties, Panties

by bjmichaels on Apr 3, 2019
Gay Male

Don't Call Me Pantyboy I couldn't believe my ears. I shouted at my roommate: "What are you saying? Are you accusing me of wearing women's panties? Are you saying I LIKE wearing women's panties? I wear MEN'S briefs -- and they're COTTON!!" He smirks and says, "You know, John, teenage girls wear red cotton panties too!" I am apoplectic. My face as red as...

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...

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...

Nephew's Readjustment Pt. 16

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** That evening Nicholas took a very long shower. He was finally unlocked again, and the soreness of his anus made it difficult to clean. Despite being free,...

The Birth of a Sissy

by sissymedic1426 on Sep 14, 2017
Gay Male

After some careful planning and serious consideration I had made the decision that I would use my parent's birthday present to me to travel to Orlando, FL. They have a University there and tons of other things to see. For a kid from a little town in NC it felt like the biggest city that I could visit and still be safe (they have the house of mouse what's the...

College Fund Ch. 07

by bjmichaels on Sep 14, 2017
Gay Male

"I want to be naked with you," I whined to Marty, "is there any night we can be together? Maybe spend the night in a motel?" I already knew the answer. His wife, Miriam, told me she will intentionally be out of town Friday night so I could lure her husband to the motel. It was simply a matter of Marty working up enough nerve to meet me in public instead of...

Bitch Dick Twitch

by cockmachine on Aug 18, 2017
Gay Male

First duty of the day. I slide my shaved-smooth body nimbly from the sheets and tip toe into the bathroom. I quickly take care of any errant stubble and look myself up and down in the mirror. I am 19, skinny, about 5'10" with short brown hair and blue eyes. Aside from the slightly-too small lace thong I am wearing, I am nude. That is, if you don't include a...