Chapter 2: First forays.
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Part I.
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A few weeks passed after my initial forays into bisexuality.
The initial couple of attempts had left me somewhat disappointed; I had enjoyed the experiences but had ended up more frustrated than when I'd started. I had found I enjoyed the encounters themselves- the taste and feel of their flesh in my mouth, their sounds of pleasure... and the element of submissiveness that I'd experienced, especially with the brusque and almost rough way the second guy... no, the second man, had taken possession of my mouth and seemed to be punishing me for not giving him all that he'd wanted.
That said, it had also scared me. I needed a bit of time for my curiosity (and growing need for something more than masturbation) to overcome the nervous trembling I experienced every time I logged onto the boards. I would just lurk, not quite bringing myself to send or post messages.
The first time I decided to venture in again, I logged into the chat room of the system and decided to get my bearings again, sit quietly without attracting attention while I listened to the chatting.
It was a mix of good natured joking and ribbing, someone complaining of a hookup and unloading an amazing amount of vitriol about the other guy, and a lot of intense silence. If you've been in a hookup chat you know what I mean- no one is talking but you can just intuit that there are private messages flying everywhere.
One of the flying messages hit me.
He had read my profile and liked it.
I had tried to be honest; since I wanted to meet someone, I did not want them to take one look at me and then turn away. The profile described me as a slightly overweight, white male, curious bottom, average stats and height, et cetera. That particular system had an extensive questionnaire, so everyone knew exactly what they were getting... no pun intended.
He said he was in his mid thirties, a few inches taller and considerably heavier than me at the time. He was a top, looking for a "boy to train". At that moment I had no idea what that meant- as I said, I was fumbling my way around. He gave me his number (this was before ID was so prevalent) and I called him within two minutes after we'd disconnected from the service.
He sounded older and excited- his deep voice almost hoarse as we spoke a bit. After the initial greeting he'd asked if I liked being dominated; I answered I had never tried but was looking for new experiences.
He ordered me to call him sir or master. And then proceeded to tell me he'd leash and harness me, tie my wrists and ride me until I begged. I could feel my erection strain against my jeans as he said that and my hands start trembling again. I could only whisper 'yes sir', or something to that effect. He went on- he'd fuck me against the wall and while gagged, blindfolded... and then he'd piss on me and make me clean him.
That last twist made me wince and lose interest- as attested by the rapid decrease in pressure at my groin- right away. I was looking for something a bit less drastic for my first time. As he proceeded to tell me what else he'd do all over me, unaware of my reaction, I hung up.
I know it was rude and unfair, not having told him I had limits, but I was scared and mildly disturbed by the turn of the conversation.
After that, it took me another couple of weeks to decide I was ready to try again. I had not had time or inclination to find a girlfriend- summer classes meant a hellish load of exams since I tended to overload my schedule- and was still curious, horny and frustrated.
I lucked out the next time I logged in. To make a longer story and three days of tentative messaging short, I agreed to meet someone using "smoke" as their nickname. We agreed to meet the day after our last meeting, during the early evening. He asked me to do a couple of things before we got there.
Some time before our agreed meeting time, I showered thoroughly. I pushed a soaped finger into my tight knot to clean it as best I could; it was hardly erotic, considering it was a smallish shower and I could feel my heart hammering too hard in anticipation to do more than try and clean. When I got out of the shower a thought struck me and I looked around for my shaving razor.
I spent the next thirty or forty minutes standing with a leg up on the sink, laying with my legs splayed and otherwise contorting as I tried to shave between my cheeks. I was thorough but careful- I figured a shaving cut there would hardly help my mood or ability to carry things through.
When I was done, the warm skin around my virgin hole was smooth and slightly pink, sensitive and definitely... odd in sensation. I was still standing around in my underwear trying to decide if I liked the feeling when the doorbell rang. Throwing on a T-shirt and stumbling into some loose shorts, I went to answer it.
Smoke was maybe an inch shorter than me and about the same age. He had a small fanny pack in hand- I remember how incongruous that looked- and was dressed in a polo shirt and white shorts. He had short hair, a mustache, skin dark enough to almost be blue-black and wide brown eyes with a slightly pensive, vaguely melancholy feel to them.
We smiled hesitantly at each other and I asked him in.
We stood around for those first few awkward moments where you don't know what to say. I don't think I even had proper furniture in the living room at the time- just an old futon that had followed me home one day. I think we commented on traffic or something equally inane; he was the one to finally ask if I was ready to go through with things.
My lips were already dry; I had my arms folded to hide the shaking of my hands. So I nodded and mumbled something in assent. He stepped a bit closer and wrapped his arms around my waist, pressing his body against me. I instinctively uncrossed my arms and hesitantly rested my hands on his lower back as I looked down at him.
I noticed three things right about then: how alive his eyes were, just how firm he seemed against me- hard chest, flat muscles under my hands. And I noticed how full his lips were as he asked if I'd ever kissed a guy.
I mumbled no and leaned in as he shifted slightly, pressing closer against me. I felt his mouth against mine. It was warm and soft and so full, tasting slightly sweet. His mustache tickled my upper lip and cheek, and then his tongue pushed against my teeth and lips. He explored my mouth slowly and deliberately, running a hand down my back to caress the round curve of my ass and making me shiver with a combination of utter terror and sudden lust. I am sure he could feel me getting harder against his stomach through the thin material of our shorts and briefs. I know I could feel him against my thigh.
He broke the kiss after a long time, leaving me breathless and looking at his wet lips when he smiled up at me. He tugged at my shirt almost playfully; I pulled it off and cast it aside and yanked my shorts down to be kicked aside in the time it took him to grin and pull off his own shirt.
I stood there with my briefs visibly tented, watching him with arms again folded in some futile gesture of modesty. He laid his shirt aside carefully on my desk, unlaced his shoes and removed his socks. Finally he stood and- watching my face with a smile- pulled down his shorts to lay them with the rest of his clothes. He was wearing white briefs that made his skin look even darker. I don't think I could have found more than a couple of grams of fat on his body- he was lean and compact, all muscles and taut skin. From what I could see through the briefs, he was larger than me in one clear respect... and seemed just as turned on by my pale, soft self as I was by him.
I think, looking back on it, that it was the clear contrast that he liked about me. I was not grossly overweight, mind you, but definitely was... softer and with more curves than him.
He stepped close once more and my arms went around him first this time; he kissed me just as deeply as before, his warm hands running up and down my spine and over the curve of my ass while I followed the lines of the muscles in his back and shoulders.
He stepped back again and took my hand. I led him to the bedroom- as Spartan as the living room, a low bed and desk, lightly decorated but for the stacks of novels and text books that always spawn when I am in one place long enough.
He had me lay face down, while he went to get something from his pack.
I did so, arms again folded under my head and legs slightly parted. My erection was almost painful, I pressed against the mattress and rocked slowly to try and ease the discomfort as I waited.
He returned and kneeled next to me. I could feel every muscle in my back tense up as I felt him lean in... then I breathed a little sigh of relief and relaxed as he started rubbing some lotion or oil onto my shoulders and back.
He was murmuring comforting reassurances as he did so. It did not take more than a couple of minutes for me to relax completely and even close my eyes, thoroughly enjoying the feel of his hands kneading and sliding on my skin. He rubbed down my arms and back, then the back of my thighs.
At that point, I could not have moved even if I had wanted to. And I didn't, when he hooked his thumbs on the waistband of my briefs and pulled them down off my hips. I sensed his hesitation and after a moment's doubt, arched my hips so he could slide them off completely.
He started kneading my ass. He would rub his thumbs against the base of my spine, run his hands down over the curve of my flesh and the back of my thighs. With each long stroke, he slipped his thumbs closer and then deeper between my cheeks. I gasped and shivered the first time I felt the tip of his thumb caress my sensitive knot of nerves.
He poured more oil on his hand and returned his attention to my clenched ring of muscle. He rubbed a fingertip against me, then two, slowly and gently. All the while murmuring for me to relax and rubbing my back with his other hand. And slowly, by degrees, I did: he pressed harder with his thumb and I could feel myself open up to accept him with a groan and a pang of pain that faded quickly.
