Gay Crossdressing In Pantyhose Stories

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Sunday Morning Deja Vu

by thebikinilover on Aug 18, 2017
Gay Male

I woke Sunday morning with a nice hard cock which I felt obliged to stroke to orgasm. I love the feel of nylon on my cock and walked over to my underwear drawer to rummage through my pantyhose collection. I decided on a natural shade and sat on the bed to pull them on. I balled up the left leg and placed my foot in the toe. Gently pulling the pantyhose up t...

Pantyhose Seduction

by nylondad on Sep 17, 2017
Gay Male

I was single and aged 26. I had been engaged for two years to a beautiful woman but the relationship had gone stale for each of us. We had lived together in a garden apartment for two years and she chose to move out and was staying with her parents until she could find a new place. I was sad as I missed her but felt relieved with the knowledge that the word...

A Fitting Surprise

by thebikinilover on Aug 18, 2017
Gay Male

I had a wedding of a friend to attend and needed a new suit for the occasion. This was Thursday afternoon and the wedding was tomorrow! Although leaving it late, I was sure I would get a suit off the rack as my size is fairly average. Traffic in the city was heavy and time was tight getting to the shop before closing, but I arrived at 5.20 with ten minutes t...

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...

Solitude Leads to Curiosity

by Creativekink on Aug 18, 2017
Gay Male

Iowa is just about the middle of nowhere. And I was just about stuck there. A few years ago, I was working for an issues group right outside of Omaha in Council Bluffs. To a lot of people, it would seem a great gig. I barely had any accountability, didn't have to report to someone except by phone or email, worked from my office, and set my own hours. There...

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...

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...

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...

Tethered and Feathered Saga Ch. 01

by doctrtic on Oct 15, 2017
Gay Male

I was thirty-one years old and was addicted to pantyhose and nylons. Various girlfriends over the years have indulged my fetish, with pantyhose sex, nylon foot jobs, and some would let me smell and kiss their pantyhose covered feet. Something happened during this time that was mind blowing. I was over at my friend Nick's house. Nick is am openly bisexual ma...