Gay High Heels Stories

10,724 results
Orientation
Length
Source
Infinite Scroll

Seduced by a Billionaire

by ret123 on Sep 14, 2017
Gay Male

I could not believe it. The woman behind the front desk told me again, "We are sorry sir, but we have no reservation for you and the hotel is completely booked for the whole week because of the meetings and retreat for a major financial institution." "I know!" I said. "I am supposed to attend those meetings and participate in the retreat! Please, help me ou...

Bicurious Fantasy Becomes a Reality Ch. 02

by StraightButCurious on Sep 25, 2017
Gay Male

A few days had passed since I sucked cock and took it into my ass for the first time. Greg, my coworker and good friend, had easily seduced me into worshiping his big cock and plum-sized balls with both my mouth and my ass. I considered myself extremely lucky because my first gay experience was with a well-endowed man in every aspect. Just the thought of his...

One Fine Day

by AnonFineDay on Aug 18, 2017
Gay Male

There have been odd days in every guys life. I mean, from the "average" odd day of some amazing good luck happening or bad luck happening, to the amazingly odd days, like you just suddenly see someone burst into flames, or you manage to actually fool someone so good into making them think you're a woman that they actually fuck you. That was what yesterday w...

Bred for This Ch. 02

by guinan on Nov 18, 2019
Gay Male

Authors note: I am still learning the ins and outs of Literotica. Some of the dialogue here is better emphasized with italics, and may not read well, but I promise to learn and add it for future stories. *** Today has been an unusual day. I was instructed to come outside of my room today and I am supposed to be seeing a client later on, but for an intervie...

Chauffeur The Ch. 03

by skinnysailor on Sep 14, 2020
Gay Male

"See it there? The dock? Look up the path and you can just see the red roof." With that the pilot banked the DHC Beaver float plane, circling the lake, checking for boats and the wind direction. He throttled the big Prat and Whitney radial engine back, lowered the nose and the flaps, and down we went. We'd been up since before dawn, loading Mr Nash's Linco...

Co-worker's Man Ch. 24

by rmdexter on Sep 14, 2017
Gay Male

As Claudia ascended the stairs and crossed a raised area that overlooked the main foyer, my eyes were glued to her long shapely legs encased in her sheer black stockings. As I mentioned after meeting her in the sex shop, she was a tall women about 5'-10". With her high-heeled sling-back shoes on, she rose to over 6' tall and towered over me. Her round perfec...

His Slave Boy 'Good Wife'

by keptsissy on Sep 19, 2017
Gay Male

I called before I got home. He answered on the first ring. He knows better than to not answer immediately. Before he could say anything I cut him off in mid-sentence. "Naked, at the door in just a pair of sexy heels, nothing else, I want you. I'm hard in my pants thinking of your submissive little ass. Your makeup and hair better be perfect, little boy, fuc...

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...

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...

Where Do I Start? Pt. 03

by MarcusVindictus97 on Nov 20, 2018
Gay Male

Saturday I slept most of the day recovering from my night with Bandit. My throat was raw from all the deep throating I had done. I got out of bed and grabbed a beer to cool my throat. It felt really good as the cold beer slid down my throat. I checked my stash and saw the ½ a kilo, the deering, and the spoon as well as my weed and rolling papers. I smiled....