Gay Heels Stories

2,228 results
Orientation
Length
Source
Infinite Scroll

True Love Found

by scrotus on Sep 25, 2017
Gay Male

Jeff and I had been hanging out for about six months. We didn't live together but we might as well have. We spent a lot of time together when we were able. I am a photographer and I frequently am on the road doing shoots. Jeff is an engineer and has to travel once or twice a month. When we found ourselves at home, we usually were together. We never planned...

Nylon Suck Again

by nylondad on Sep 16, 2017
Gay Male

My cousin Jimmy and I burned up the telephone lines after our first meeting. In that meeting I had "borrowed" a pair of my sister's stockings and gave them to my cousin as a gift. He and I had a thing about women in stockings and he would focus on my sister. I tried the stockings on at his home one weekend and I ended up sucking him off twice that weekend. T...

Dirty Dream

by Jamie_in_dresses on Aug 18, 2017
Gay Male

It wasn't like me at all, I am naturally very shy, but something inside me burned to explore this ongoing fantasy. The need was tangible, I dreamed day and night of being dressed as a girl, giving myself willingly to a man, thrilling to the feel of him touching me, possessing me, filling me. I awoke at night to the clear feeling of my imaginary lover's cock...

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...

Pest Control Heaven

by showitall2u on Apr 13, 2020
Gay Male

Today was pest control day. I knew there would be a strong young man stopping by about 4 o'clock. I slipped on a sleeveless top and a pair of hi cut slimming panties. I pulled on some skin tight yoga pants that definitely showed my bulge between my legs. Ding dong went the door bell. I hustled to the door and opened it wide. I invited Taylor in and we talke...

Bringing Out the Sissy in Fred

by 0ra1Master on Aug 18, 2017
Gay Male

"Yessss.., ooh yesss, aahhh! yesss! That's it! Thaat's iit! God it feels good, so good! Ohh Sammy! Fuuck mmee! Yessss, yessss, fuuck, fuuck, yesss!" Mary Pats nails were digging into my shoulders; her ankles were hooked on my ass cheeks. I wasn't sure who was riding who but it was what it always was, a great fuck. "Give it to me Sammy! Harder...., h.a.r.d.e...

Bear Seduction, the Buddy

by wildrideagain on Oct 15, 2017
Gay Male

I don't know if I'm going over board and have become a full blow cock whore, or if it's just something new that I need to explore so it's always on my mind. Kevin's cock and satisfying him are the only think that's on my mind it seems. I'm giving myself blue balls during my work day thinking about him. Just thinking about sliding the silky smooth thigh hig...

On the Docks

by sr71plt on Aug 18, 2017
Gay Male

I was moving among the containers on the dock, looking for the one that had the goods I'd had shipped from Portugal in it, when I reached a pocket of isolated dock space between the stacks of truck containers and the waterfront. I was about to turn and move back along the row of containers to examine the numbers on the other side of the tight aisle, when I h...

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...

Powerhouse Conversions

by AmberFemXD on Aug 18, 2017
Gay Male

Falling flat on my face was not the greatest way to start off the evening but there you have it. I was unpacking taped cardboard boxes in my newly rented apartment. Such a hassle. "How's it going?" Someone had stepped inside. I forgot I had left the front door open. He was a very big man, somewhere around 6'2 wearing all leather. Quite intimidating actuall...