Gay High Heels Stories

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Infinite Scroll

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...

Becoming a Gal Friday Pt. 09

by Showoff888 on Sep 14, 2017
Gay Male

Here I am standing naked in red 6 inch plastic high heel platform shoes, all dolled up in makeup with red lipstick and sporting a semi-erect cock being held in a fabric cock ring thong that is also holding a penis shaped butt plug in my ass. I am in my Ex's apartment complex in the morning hours with David in an elevator. I feel so vulnerable and so much l...

Little Sex Toy Ch. 05

by keptsissy on Sep 26, 2017
Gay Male

I'm squatting in the middle of his cold cement basement floor, just over the drain in his laundry room, sitting back on my high heels. The 4" spike heels he insists I wear now around the house, wobble in them and get whipped for it, walking or squatting. He says a 'lady-like' little bitch should know how to wear high heel shoes. Leather, padded restraints...

Co-worker's Man Ch. 25

by rmdexter on Sep 14, 2017
Gay Male

After having me service her through six orgasms, Mistress Claudia asked me if I was ready for more. ME.....?????...I couldn't believe that SHE was ready for more! "Yes Mistress," I replied obediently as my tongue came out and ran around my lips and chin. I wanted to make sure I had gotten every drop of my cum from her luscious tits. I looked down at the imp...

My Memories of David Ch. 04

by msmithyxx on Dec 30, 2017
Gay Male

##### Author's Note ######## It's been about two years since I last posted a story. I found a half done draft of this chapter and remembered how much I loved writing these, so I'm back and finding more interesting ways for Mark and David to get into naughty trouble. I hope you enjoy it. ######################### Several months had passed since the bachelo...

Snow Bunn

by FyodorKaramazov99 on Aug 17, 2017
Gay Male

Peter Hoang stared out at the winter blizzard driving hard at the large picture window. He was momentarily thankful that he had made the trip prior to the snow closing the roads-especially the long unpaved road into the cottage. The fire licking at the logs in the fireplace reflected off the glass. He looked at his faint reflection. From the tip of his dark...

Inventory Night

by bullockhall on Aug 18, 2017
Gay Male

My name is Mike Martin. I'm 21 years old, 5' 8" tall and weigh 127 pounds. I have blue eyes and blonde hair I like to wear long. And I'm gay. I've known I was gay since I was 10 years old. I live in a small town in Missouri with my mother, a single mom. I never met my dad. Mom knows I'm gay, but nobody else does. I've always been too shy to tell any school f...

I Live to Serve Him

by tiedNbound on Aug 18, 2017
Gay Male

I love my master's cock. In fact, I worship it, and him. I am in love with him. I will do anything to please him, including kneeling before him, showering his cock with my love. He loves to have me suck his huge, beautiful uncut cock everyday. He always makes me take his sweet, salty semen on my face, in my asshole, or in my mouth. It is never wasted. In th...

My Hot Uni Roommate Ch. 05

by CreamStuffedTwink on Jun 17, 2019
Gay Male

Previously: "Want to watch a movie or something?" he asked. "Sure." I went and sat down on the couch while Michael stood with the remote and cycled through Netflix until he found something he wanted to watch. I expected him to just sit next to me, but after he sat down he pulled me over to him until he was lying down with me as his little spoon. My skin t...

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...