Gay Heels Stories

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Becoming a Gal Friday Pt. 01

by Showoff888 on Sep 14, 2017
Gay Male

At eighteen I fell in love head over heels to the hottest babe I ever met. She was ten years older than me and well, the sex was amazing. She took advantage of the fact that I was always horny, had stamina and could just as easily get hard again to go as many rounds as she wanted. But I guess I was just a passing phase with her, I was merely her boy toy....

Becoming a Gal Friday Pt. 04

by Showoff888 on Sep 14, 2017
Gay Male

Here I am wearing stiletto heels, thong panties and a matching bra. I just got hired in this work/live job for two Gay bosses. I must be drunk, cause I can't believe what I just did. I actually sucked his huge black cock! What the fuck is happening to me? I'm stunned. After sucking him, he pulled out and gave me a facial! His goo was all over my face like on...

Becoming a Gal Friday Pt. 10

by Showoff888 on Sep 14, 2017
Gay Male

I'm dressed in my 'Fuck me' backless platform pink six inch high heels, and nothing else, having stripped off the denim Daisy Duke cut offs, the sweatshirt and even the white string thong that was holding in my butt plug. I'm all made up with long lashes, mascara, and pink lipstick, whispering in my white bosses ear to please fuck me. I had previously been...

New Horizons Ch. 02

by 69plus1 on Sep 14, 2017
Gay Male

I try to return the feeling to Jim. As Jim is sitting back on his heels I get up onto my knees and crawl to him. I take his face into my hands and kiss him full on the mouth. We had both discussed this and both were not sure how we would react. At this moment I really didn't care. He had gotten me off so well that all I wanted to do was share the feeling; h...

A Fantasy of Mine Ch. 02

by ima_milkwood on Nov 12, 2019
Gay Male

I say yes, and widen my stance to bend over in these heels. The weight of the tits pull me down and the counterbalance of the ass levels me out, I have never felt so sexy. So desirable. Basically on my toes, with my ass pushed out snorting up the first line of whore fuel. I tilt my head back and take a huge snort to make sure I got every grain as far back in...

Death in the Rockies Ch. 07

by sr71plt on Sep 14, 2017
Gay Male

For the rest of the day I avoided what sexual encounters I could. I enjoyed being fucked as much as the next male satyriac, but this was a bit much, coming on the heels of the vetting process. Besides I had expected to be contacted by someone else on the inside of the ranch—someone who was supposed to maintain communications with the special unit that had be...

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. 06

by rmdexter on Sep 14, 2017
Gay Male

I had just finished taking Frank's first load of the morning and then chased it down by swallowing my own load of cum. I sat back on my heels and looked up at Frank wondering what was coming next. "C'mon with me," he said, getting up from the bed and making his way into the en-suite bathroom. I followed like a little puppy after its master. Frank made his w...

Born to Suck Ch. 04

by rmdexter on Sep 19, 2017
Gay Male

Like a puppy following its master, I was right on Mr. Jarvis' heels as he entered his bedroom. He stepped over to the bed and turned on a light sitting one of the bedside tables. The light cast a warm glow over the room. I looked around and the room was tastefully decorated without being overly ornate. You could see from the types of pictures on the walls an...

Becoming a Gal Friday Pt. 08

by Showoff888 on Sep 14, 2017
Gay Male

Here I am in the front seat of my bosses SUV, naked wearing only a pair of pink platform high heels. My feet are spread wide with those heels sitting on the dashboard. I have this plastic cock butt plug nestled in my ass, and I am sporting my fully aroused erections that my boss, David has oiled for me. We are driving to my Ex's place to get my stuff out of...