Gay Pantyhose Crossdressing Stories

156 results
Orientation
Length
Source
Infinite Scroll

Stoner with a Boner

by Tahoestud on Aug 18, 2017
Gay Male

Three days ago, my wife passed away after being hit by a car while jogging. She always enjoyed running to keep in shape. I was in a daze all during the funeral not quite coming to grips with fact that she was actually gone. In the hours following the funeral, I returned home with my two young daughters, who along with their friends, stayed in the living room...

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...

My First Time Ch. 01

by doctrtic on Aug 18, 2017
Gay Male

He was my first, he was in his 40's I was 20. I worked for him and he invited me over for dinner and drinks. I really was not aware of his interest in me. Michael was just a nice guy. I was kind of a pussy hound at the office,if the ladies were in business attire(pantyhose and heels). I would make a bee line to talk to them. Michael finally approached me...

The Book and Video

by TerriC on Sep 14, 2017
Gay Male

By the time I was 18 I had been dressing in my mom's lingerie for a few years. I had always liked to sneak into her room when she was out and try on her panties, bras, and other assorted lingerie. Her pantyhose were always my favorite though, they felt amazing on my slight, nearly hairless legs. As my passion for wearing pantyhose grew, I took to keeping a...

Third Shift

by TerriC on Aug 18, 2017
Gay Male

"I slapped her tits with my cock, rubbed my balls on her nose, and sprayed all over her face." That's the reason no one liked working with Leo. Not that he was a bad guy, he just had no filter when it came to speaking. Lines like that, to Leo, were as normal as "Good morning," or "Extra sugar with my coffee please." The early fall was the busiest time of...

Married and Gay Ch. 02

by paulsenc on Aug 18, 2017
Gay Male

As the days followed after my initial encounter with Larry, my desire to be with him again grew stronger and stronger. I felt this inner need to express a kinky side of myself that I hoped he would like. I often enjoyed wearing pantyhose as a way of getting off during my many jack-off sessions. I called him several times after our first time to see if we co...

Sharing Secrets Pt. 04

by Showoff888 on Sep 14, 2017
Gay Male

NOTE: This story entails piss play. ***** Hoshi slowly returns to consciousness and awareness as the wisps of sexual bliss begin to fade. He can feel the warmth of his naked body lying under the warmth of his friend's naked body. He can feel the mass of cooling river of cum that was deposit between his ass cheeks and is making its way down his ass onto t...

Lonely Cock Sucker

by silkstockingslover on Dec 9, 2019
Gay Male

Summary: Lonely married cock sucker discovers young cock close to home. Note: Thanks to Tex Beethoven for editing this story. Note 2: This is a holiday 2019 Contest Story. Lonely Cock Sucker I love cock. I love everything about it. The variety of shapes. The upward curve that often makes me gag even on a smaller cock. The downward curve that slides int...

Nylon Suck Again Ch. 02

by nylondad on Sep 16, 2017
Gay Male

I slept in one of the single beds that night. After Jimmy and Nils had flooded me with their come I had a beer and went to sleep. It was apparent that both guys wanted a second round but for some reason I was not up for it. My stomach was a little upset after it was flooded with the two massive loads I had swallowed. Before dozing off I could hear them speak...

The Misadventures of Nylogirl

by NylogirlCD on Aug 22, 2019
Gay

Megalopolis is a crime riddled city in dire need of a hero, or in my case, heroine. My name is Julie Hosaree, but my alter ego is Nylogirl. From what I can recall from my broken memories, I'm the result of genetic experimentation, an attempt at a super solider. While I have the super strength and speed there are some... Side effects. My powers only work when...

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