Gay Crossdressing Bondage Stories

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Cocksucker: Cum Slut

by silkstockingslover on Sep 14, 2017
Gay Male

You do not need to read the first four chapters of this story to enjoy this story of a straight man that gets submerged into the drag queen world of San Francisco (but obviously it helps). In case you are curious how this straight married man got into this predicament here is a brief summary of the first four chapters of "Cocksucker": Chapter 1: Cocksucker...

Hotel Night

by guy_manuel on Aug 18, 2017
Gay Male

It was my first time crossdressing. I have no gender identity issues or anything, I just wanted to try it. But I also wanted to have a little fun since I was sure this would be the only time I'd do something like this and I hadn't gotten laid in a while. It probably wasn't the smartest idea, but if literotica had taught me anything it was that Craigslist was...

At the Movies

by Michele G on Sep 14, 2017
Gay Male

Everyone knows Bobby and I are friends, but the don't know how close of friends were are. He's known about my crossdressing for sometime because we have been lovers for that long. One weekend my folks were away Bobby called me and asked if I'd like to get dressed up and go to the movies. At first I balked at the idea of going out in public dressed up, even...

My Inner Slut Ch. 03

by SlutAlexR on Oct 15, 2018
Gay Male

Well, no doubt about it: I was a slut. I had sucked my first cock; I had been fucked hard in the pussy; I wore girlie clothes for my Man; and here I was, his load drying on my face, ready to leave the house. Todd had laid out a few things he wanted me to wear during the day. Skinny jeans, a tight white t-shirt. Nothing too drastic there. But I had to wear b...

My Gay Crossdressing Vacation Ch. 02

by Flame666 on Apr 21, 2020
Gay Male

We pulled into the parking lot, Paul kissed me again and told me that they would pick me up at 9:30 the next night for our date and tour of the gay bars. I got out of the car and started to walk into the resort but noticed that the bar was closed and I was hungry. There is a Circle K about 2 blocks way and I decided to walk over and get some cokes and some e...

The New Order Pt. 04

by Iamkrazy4 on Apr 21, 2020
Gay Male

Part 4: On The Road to Love There I was, on my back, a dick in my butt, mouth, and both hands as I laid on table they had brought into the locker room. Around 3/4ths of the football team, and the coach stood around cheering as they celebrated their upset victory over our rivals. My throat and ass were sore as this onslaught had been going on for over an h...

It Was So Exciting

by sindyxdresser on Aug 18, 2017
Gay Male

It was about 230 am Friday night when I walked into the Crypt adult book store on 30th Street in San Diego Calif. The Crypt's usual clientele was mostly gay men, and tonight was no exception. I felt my face burning as I walked back into the peek booth part of the store. These booths had no doors or curtains so offered no privacy of any sort. There were sever...

The Reluctant Bear Hunter

by newpaulman on Jul 3, 2019
Gay Male

First I must apologise to any gay men reading this who like their stories with a romantic element. That is not what I am looking for with a man. I am a part-time bisexual. I can go months without thinking about gay sex, but then the urge comes back. The urge to be fucked, that is. The urge to suck a cock and see spunk fly from it. The urge to get naked with...

Crossdresser's Unexpected First Time

by kprice1984 on Nov 27, 2017
Gay Male

Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I'm just getting around to writing it after several years. ***** I'm a 20 year old guy, very good looking, easy to get girls. Brown hair, green eyes and a sexual appetite that's hardly ever satisfied. I had always had a craving or tendencies towards being a lit...

My First Kiss

by amygurl on Aug 18, 2017
Gay Male

It all started about 2 months ago when a new neighbor moved into the apartment next door to me. His name is Jason, he is very personable and just an all around amazing guy. He is 34, about 6'3" with black hair and blue eyes and we hit it off pretty much as soon as we met. We are both veterans and newly single and we both liked to watch sports on TV, but we d...