Gay Wearing Nylons Stories

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Introductions

by skinnysailor on Feb 12, 2019
Gay Male

Marie is my best girlfriend. She's straight, so it's nothing like THAT. How we became friends is kinda funny. One Thursday night I decided, what the hell, I'd go to a different club than the gay bar I usually frequent. We both work for the same company, but hadn't really spoken. Just 'hi' in passing, that sort of thing. Anyway, I had my long blond hair do...

The Joys Of Crossing Over

by Darla Leslie on Aug 18, 2017
Gay Male

It all began back in my teen years in the mid-west when I was just a young, confused lad of eighteen. I was a relatively good looking boy, long blonde hair about 4 inches below my shoulders, 5 feet 11 inches tall, 170 pounds, green eyes with a VERY well endowed girl friend whose body of 38DD-25-36 I enjoyed, admired and envied ---- envied because I'm a close...

College Days Ch. 06

by jjdtx on Sep 14, 2017
Gay Male

Chapter 6 -- Tim and I get even with Pete My playing boss to Tim was an awesome turn on. He loved being told exactly what to do. He had been coming over to my dorm about three times a week. He'd only come over when Stephen, my roommate, was not going to be around, which I was hoping to change so that Stephen could see his perfect smooth body too. He came o...

Jo and Mike

by skinnysailor on Nov 12, 2019
Gay Male

I've got the perfect job. I'm an interior designer at C###### the nationwide premier designer builder of exclusive homes. I mean, if your dream home will cost less than two million, don't even bother calling. Right? I mean, where else could a five foot tall, third generation Vietnamese Canadian, be allowed, even encourage to wear eye liner and nail polish t...

My Gay Crossdressing Vacation Ch. 01

by Flame666 on Apr 21, 2020
Gay Male

It was mid-January and I was getting tired of the cold and I was horny so I started to think about planning a gay vacation. After a lot of thought I decided on Palm Springs in Mid-February. A bit about me, I am a straight looking and acting man 60 years old slim and fit. However, I love cock and like to dress up in panties and other lingerie. A few years ag...

Jason's Costume

by nylondad on Sep 17, 2017
Gay Male

The following story is true. It occurred fifteen years ago. By virtue of the fact that yesterday was Independence Day jogged my memory. I had married a woman with three sisters. All but one of the sisters had kids. The oldest sister Carolyn (my sister in law) had a son by her first husband named Jason. He was a pleasant kid who grew up in with Carolyn and h...

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...

Made A Man(In And)Out Of Me Ch. 02

by Cicero6 on Aug 18, 2017
Gay Male

Well, it had been three days since the party and I still felt like I’d been ridden hard and put away wet. Monday came and went and thankfully Kelly had not mentioned anything about the party. By Wednesday, however, I received a phone call from her at work. “Sweetie, I am wondering if you’re planning on doing anything this weekend,” she asked. I thought fo...

Fucked

by TerriC on Aug 18, 2017
Gay Male

It hurt. It hurt a LOT!! Every thrust was painful, even with plenty of lube. There was no numbing, no getting used to the feel. It was just painful. Yet, I let him keep going, it had to feel good at some point. An hour ago I was buzzed chatting online, horny as always when I drank. I loved drinking and chatting online, it was harmless fun, playing a role wh...

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...