Author: myfavoritemistake

[MT] Pegged by a transman firefighter – part 3

Sensing I had done something wrong, I apologized for overstepping, but he just shook his head and replied, “Come with me,” and began walking toward his bedroom.

When we reached his bed, he became tender once again, first kissing my lips deeply, maintaining eye contact with me all the while in a way that no partner since has matched. He began kissing down my torso, eventually sliding his rough hands under my tshirt and sliding it off over my head. Next were my pants, which he unbuttoned with dexterity and tossed to the floor, yanking my boxers down soon after.

My cock was throbbing by this point, and he could see that it needed attention, so he fell to his knees and took its entire length into his mouth. This was the first time I had ever looked down to see someone with a beard sucking me, and I felt a jolt of electricity flow through me. The attention was short-lived, though, as he soon stood up and began removing the rest of his clothes. He unbuttoned his long sleeve flannel shirt to reveal a chest that was undoubtedly hairier than mine, but which had two ugly scars running across the nipple area. He caught me looking for a moment, and I thought that perhaps something needed to be said, but he simply continued, dropping his shirt to the floor and then reaching around me to grab one ass cheek. “Lie down on the bed, babe..Face-down,” he said with a squeeze.
I complied, albeit with some anxiety, and heard him rummaging in some drawers. “I only bottom with women,” he mused. “I only top with men. You good with that?” Read more »

[MT] Pegged by a transman firefighter – part 2

We did not, upon that revelation, start fucking immediately. We hung out a few more times, getting to know one another more intimately, and he got me to open up about some of the hetero-flexible fumbling I had attempted, and he was patient enough to educate me about his life and identity.

We had sort of abandoned the part of the conversation about our feelings for one another until it came roaring back after a few stiff, late night drinks at his place one night.

We were on martini number 4(?)5(?), when he slurred, “You are totally queer for me, aren’t you? You totally want to see what’s between my legs, don’t you.” He always had a pretty bawdy sense of humor, so I just let it slide and sort of giggled, “Whatever, man – you’re wasted.”

Then, the mask fell, and he got serious and intense. “Why can’t you just admit it? You’ll still be you, even if you’re a fag.” He had hit something there – I was so sure that being intimate with him was going to destroy some piece of my identity. But I knew then that he was right. I did want him, and, more importantly, I was falling for him. Read more »

[MT] Pegged by a transman firefighter – part 1

Don’t know why, but this morning I’ve been mentally playing back a bunch of sexual experiences I haven’t thought about in years, and one that keeps popping up is the time I spent with a gorgeous transman FWB. As a warning, this happened about 20 years ago, when I was in college, at a time when I wasn’t super secure in my sexuality and when I was pretty ignorant when it came to transpeople. This story has some mis-gendering in it, because I was young and stupid.

As with the other stuff I’ve been posting today, part 1 is the set-up. If you want to skip to smut, read part 2.

Basically, I had known that I was some brand of bi since I was a kid, but it wasn’t really until I was in college that I in any way explored my sexuality. I held on to some latent self-loathing homophobia, though, and my first few years of same sex play were pretty awkward. Read more »

[MF] My visit to the massage parlor, part 2

I was more terrified at this point than I had any reason to be, and some part of me was sure that the police were going to burst through the door at any moment. As she squirted lotion onto her hands and began stroking my shaft, I could hardly let myself relax and enjoy.

She could tell I was nervous, and rubbed my chest with her other hand, ever so often leaning in to drag her hair across my belly or whisper in my ear, “It’s ok, baby, it’s ok.” It hadn’t even occurred to me to touch her, but as I grew in her hand, I became bolder, and I let my hand drift under the edge of her shirt and up toward her chest.

She smiled, knowingly, as I took one of her nipples between my fingers, rolling it around. Her eyes closed for a second, and she purred, “You like me, baby? You want fuck?” never letting go of my cock as she asked. Read more »

[MF] My visit to the massage parlor

This story took place about 10 years ago, right before I got married, but I’ll never forget it. I had never paid for sex before and had lived a fairly cloistered existence, but I had always fantasized about getting a happy ending at a massage parlor.

I don’t know if I was more paranoid about disease or law enforcement, so I went on this website that provides reviews of massage places and tried to pick one that, all things being equal, seemed like a fairly safe bet.

When I arrived at the nondescript store front, I was greeted by an older, Chinese woman who barely spoke English. She knew enough to tell me where to leave the tip, but that was about it. After leading me to a small, dimly lit room, she left me to get undressed. I could feel myself shaking nervously as I disrobed and lay down naked on the table.

A few minutes later, the door opened and a different woman came in. She was petite, flat-chested, but full in the hips and was probably in her late 20s. She had long, black hair that hung halfway down her back. Read more »