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.
