I have been involved in many brief or "casual" sexual encounters with both men and women for most of my adult life. I have decided to begin cataloging them here. I am now in my early 40s and living full time as a dedicated submissive of my beautiful, but often demanding, Mistress. This journey began with years of curiosity driven, wanton behavior that slowly flowered into full blown fetish & kink. My first step down this path would begin before my 30th birthday.
As I recall I was on the tail end of lifeless marriage of 7 years and in my late 20s. A few years before I met my (then) wife, I was working a menial job downtown as an usher at the local movie theater. I was around 20 and Eric was a little older than I was, but not by much, he was larger too, but not muscular per say. He was black skinned, with a roundish head, strong hands and apparently, found me very attractive. First, he befriended me and then started dropping hints about how he wasn't into girls, eventually he just flat out asked to give me head. I found it kind of amusing and stayed friends with him even after I declined. Once he literally offered me a few hundred dollars in cash to blow me. I was tempted but chickened out. We eventually lost touch and I didn't hear from him for years.
One day, after my then-wife asked for divorce, I was feeling lost and I reached out to him, probably from some misguided sense of needing to be wanted. He snatched up the opportunity to meet me and within a week I was driving to his apartment late one night. Although no one had said so, we both knew what was going to happen... I remember specifically thinking to myself in the car ride over that another man's cock would be in my mouth for the first time in less than an hour.
He was wearing black gym shorts and a white t-shirt when I arrived at his apartment, with nothing underneath but a noticeably large bulge pushing through his pants. He gave me a soda from his fridge, we chatted for a while, I don't remember about what, I'm sure neither of us cared. After a few minutes we were sitting down in his typical, sparse, bachelor type apartment. Complete with black leather couch, matching loveseat, TV, gaming system of some kind, basic kitchen, etc... it all felt very college dorm type. I don't recall exactly how, but the next memory I have is being on my knees, he was seated on the couch with his legs spread and his hard cock reaching out of the top his shorts.
I was concerned I couldn't get it into my mouth without my teeth scraping it, it was so much thicker than I imagined it would be. I had never seen a black man's cock before, but I instantly fell in love with it. I remember how strange it was to hold a dick that wasn't my own. I remember being inches from his mushroom shaped cock head and noticing the way the slit on the tip kind of wrinkled up and back into itself. My own slit was more of a straight line, like a miniature vagina, I remember thinking that all cocks must be slightly different. I remember the soft scent of Irish Spring soap masking the musk of crotch and feeling the weight of his large round balls. I started licking the sides of his shaft, tasting dick for the first time, working my way back to the tip and then feeling the cockhead slip into my mouth and hearing him sigh in relief as the boy he chased 8 years prior was now looking back up at him with his mouth stuffed wide with his black cock.
The thing no one tells you about giving head for the first time is that it really is actual work. There is a stiff, uncomfortable cock lodged in your mouth, often bumping the back of your throat, you are struggling to breathe while keeping your teeth clear of the rod being shoved in your face hole and the man on the other end is just having a great fucking time. I've been given hundreds of blowjobs, so when I put all that dick past my lips it was a strange to not be experiencing the mind melting sensation of a warm mouth wrapped around my own cock. In place of the instant pleasure Eric was enjoying my jaw was starting to get sore, I choked a bit and gagged as I tried to go down as far as I could. My hand and neck were getting tired from bobbing up and down and stroking his shaft. I couldn't believe I had been sucking his dick for like 5 minutes and he hadn't cum. I would have blown a load in 90 seconds if I had gotten such enthusiastic head, but what I didn't know yet was that Eric never came from oral. I spent 20 minutes giving my first blowjob with a smiling black man watching me desperately choke down his dick. He caressed my head, chuckled a bit and told me he wished it would never end.
I had the growing concern that I must be some sort of oral failure and started to give up hope that I could finish him off. He sensed my rhythm had changed and he told me to slow down and enjoy myself. So that's what I did, I spent more time on his plump head which relieved some pressure on my jaw and gave him long strokes with my hand. After a while he pulled his cock out of my mouth and presented his balls, Eric loved his balls sucked, and I spent longer than I wanted to massaging each one individually in mouth before he pointed his cock back at my lips, a not-so-subtle request to resume pleasuring his prick.
I don't remember exactly how, but it became clear it was time for him to take my virginity. We ended up on his bed where he laid on his back, he had me lube his cock, first with my mouth and then with a small bottle or tube of some kind. He then proceeded to relax and watch as I tried to sit down on his waiting pole. He was rock hard and placed both hands around my hips as I would take just a fraction of him and then retreat, repeating the process and rocking my asshole around head of his cock, dipping it in and out and trying to go a little deeper each time until suddenly, half of his hard, slippery cock ripped right up inside of me.
