In the 1990s, following the regrettable end of a long-time but challenging relationship with a great lady, I was in no hurry to get into another serious relationship. But I needed a means of addressing my sexual appetite, and was open to alternatives to one-night-stands with women.
I had experimented on several occasions in my life with sex with another man and found it erotic and satisfying. In all the cases I was a bottom; it seemed to fit a need of mine, and I liked how being submissive in bed contrasted with my assertive behavior when having sex with a woman. I appreciated that my ass - honestly, I tended to think of it as my man-pussy - was highly erogenous and having a cock in it was a serious turn-on. At least on one occasion I orgasmed hands-free from just being fucked - a mind-blowing experience - and several other times it had only taken a few strokes, with a hard cock inside me, to cum. I definitely wanted to do that again.
At the time, one of the most dependable ways to get a hook-up was to cruise the M4M chat rooms on AOL. They often were geography specific, making it possible to limit the time and miles to a quick fuck. It was that approach I was using when I crossed paths with a dude in San Bernardino - just a short drive for me - who was looking for someone to suck his dick and then take it in the ass.
As we IM'd after meeting in the chat room, Mike and I exchanged stats and preferences. He was a little younger than my early 40s, about my same body size, and had a thick, cut 7" cock. He was a nurse at a local hospital and had a roommate with an out-of-synch schedule that allowed Mike to be home alone in the evening up to midnight. So long as a "guest" was gone before the roommate returned, he was fine with hosting at his apartment.
We chatted twice on AOL before setting up our first meet. I showed up in what would become my usual outfit - sweat pants and shirt, no underwear and a pair of slip-on shoes. He greeted me at the door in his standard attire - a t-shirt and boxer shorts. We spent a little time on pleasantries; not a wasted effort, since it was important to determine that neither of us were serial killers. But basically, he was the guy he represented himself to be online, and when he suggested moving to the bedroom, I didn't hesitate.
The first two times we met and had sex, it was... well... perfunctory. That isn't to say it was bad, but it basically consisted of getting naked, a short blow job (me doing him), rolling a condom on his cock, and my bending over and taking it from behind. The odd part was that he didn't cum while fucking me; he would pull out and suggest that we jerk off together on his bed. We would do that, clean up, get dressed and I would leave.
I almost didn't respond to his invitation to come over a third time, but I thought "what the heck" and said yes. As it turned out, the third time was charmed and was very different from the previous visits.
When I arrived, I sensed that Mike wanted this encounter to go differently, and he confirmed that suspicion by not waiving me over to the couch to sit. Instead, after closing and locking the front door, he turned to me, grabbed the hem of my sweatshirt and pulled it off over my head. I was sorta excited by this new approach, and was thrilled as he stepped closer, cupped my tits in his hands, and began pinching my quickly erect nipples with his fingers
Two things about my nipples: First, they are large - much bigger than pencil erasers - and get engorged quickly. Second, they are incredibly sensitive and playing with them is an instant turn-on. I may have previously mentioned this in passing to Mike, but until now he really hadn't acted on it. Well, that was clearly about to change.
As he began pinching my nipples really hard, and tugged at them a bit, I let out a soft moan of pleasure, encouraging him to continue. Mike escalated his attention by bending forward and sucking one of my nipples into his mouth, and then nibbling it with his teeth. Oh, god, it was so good, and it got better as he began to actually bite my nipple. This triggered an electric pulse from my chest to my groin, a connection that he reinforced when switching to the other nipple by reaching down and palming my crotch.
I don't know if Mike was calculating this reaction, but the combination of stimuli had an immediately feminizing effect. His lower hand was caressing my genitals through the sweatpants like you might do to arouse a female; he wasn't jacking me - he was petting me. And while my dick hardened, the sexual ache I had was deep in my man-pussy. It was incredibly hot to be handled this way.
After several minutes of this erotic intimacy, Mike backed away and led me to his bedroom, where we both undressed. Once again he surprised me by saying, "I need you to suck my cock" and proceeded to stretch out on the bed, his erection standing tall. I had sucked him before, but only as a short warm-up to getting fucked; I had the impression he wanted more this time. So I lay at a cross-angle to his naked body and positioned my head near his cock.
As I reached for his hard-on, and brought it close to my mouth, I could tell that he had recently showered - even his crotch had a clean scent. This was confirmed as I licked the shaft and then sucked the tip - he tasted fresh. This immediately motivated me to take most of his cock into my mouth, swirling my tongue around it. As it hardened and lengthened a bit more, I really got into the blow job - wet, noisy with a lot of sucking action. I was rewarded with deep groans from Mike, and that became an immediate feedback loop: I really wanted to pleasure him with my mouth.
Mike gently rested one hand on the back of my head, encouraging me to keep his cock deep in my mouth and at the entry to my throat. The other hand reached down my back and fondled my ass. It felt nice - a combination of caring and erotic. It disappeared for a moment and when it returned his middle finger was wet and rubbing the entry to my man-cunt. He wet the finger again, and this time used the saliva as lubricant to penetrate me. Mike repeated this once or twice as he set about finger fucking me as I sucked his cock. I'm not sure who was more excited by this foreplay, but I knew he was making me more horny by the minute.
It didn't take long for Mike's cock to begin leaking pre-cum, and this only served to heighten my arousal and desire to please. The taste of his testicle juices, combined with the clean skin, was a huge turn-on. I sucked him even harder, hoping to draw more fluids out of his body and into mine. The thought of taking him all the way to orgasm was pretty appealing.