Gay Caught Wearing Lingerie Stories

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The Birth of a Sissy Pt. 02

by sissymedic1426 on Sep 14, 2017
Gay Male

Upon my return from Orlando I was tasked with making a decision of where I would go to school in the fall. At first I was intrigued by the possibility that I could go the University of Central Florida, but quickly remembered that I had never stepped foot on the campus while in Florida. So it was a decision between the schools in little old North Carolina, at...

Zius

by Scotsdude on Aug 18, 2017
Gay Male

Year: 2084 "There is still much talk over who will win the next General Election on the planet Zius." The EBC reporter announced. "The current Zius government feels they could lose to the Global League, who already control the planet Reid and IO. Should this be the case, then they could end up imposing a Feudal status on the planet as has happened on others...

Naughty Boy Ch. 02

by fantaseeboy on Sep 1, 2017
Gay Male

I'd always been embarrassed and ashamed of my body. I suppose I had an image of what a guy is supposed to look like in my head, and that isn't me at all. I had to look up at nearly everyone I'd ever known. The first time Sam picked me up in his arms he laughed and said I couldn't weigh more than a buck soaking wet! Well, that's not quite true, but it's close...

My Boss and Master Ch. 03

by MitchCapslock on Sep 14, 2017
Gay Male

All comments and criticism welcome. My Boss, My Master: Losing it I kept up my office routine, even though I knew Mr. Compton was out of town and might not be back for the rest of the week. Each morning, I would stop in the lobby restroom, change into a pair of panties and then head to my office. I quickly found that I liked the feel of women's underw...

Zara's Closet

by Jamie_in_dresses on Jul 4, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** Our family took a vacation in Paris a few years ago, well my Dad had to work, but My mom, older brother and I went along for the ride. I was 18, just out of school, My big brother, Gavin, had graduated a couple of years ahead of me. We stayed in an apartment owned by Zara, a femal...

420'd Accidental Bi Sex

by married_but_curious on Dec 10, 2018
Gay Male

The personal ad I wrote while stoned and horny: I'm looking for someone with a bit of a kinky streak. I'm tall, smart, funny -- you be that too. Here's what I like: (attached picture from the waist down of what I like -- a woman with a booty wearing black lacy panties) *** I posted the ad, not expecting much -- this site was a sausagefest, perhaps ten me...

Pauletta Celebrates Nude Day

by Boxlicker101 on Aug 18, 2017
Gay Male

This tale of Pauletta the beautiful drag queen, and his friends and sex partners is an entry in the Literotica Nude Day Writing Contest. After reading this story, please vote whatever you think it deserves. Comments are also appreciated. * On July 8, Pauletta approached the entrance to The Purple Knight, his favorite bar in the Castro District of San Fran...

Hot Wet Cabin Orgy Ch. 03

by Abaddon89 on Sep 15, 2017
Gay Male

After some thought, Stacy had figured out how to get back at Alex. She had known all the girls in college who had found out too late their boyfriends were gay, and she had always wondered how they didn't know. Now, she couldn't believe she was one of those girls. Of course, Alex had done everything he could to get back with Stacy. He had sent her embarrassi...

Rick Needed a Beer, Gets Much More Pt. 10

by Iwanttwo on Jul 31, 2019
Gay Male

"Sue, I like having a hairy body, I admit Tim looks really hot smooth, but I don't think that's for me." "You didn't want to put on the pink panties I got you last night, and ended up loving how you look in them, like a sexy cocksucker, didn't you? We are going to shave you, and then I have some really sexy things for you to wear." After arguing for a whil...

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...