Chapter 2: First forays.
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 escort izmit 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 izmit escort 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.
He pushed his thumb in to the first joint, turning and twisting it inside me as he continued to caress and stroke me. I opened my legs a bit further, my face now pressed against my arms and my breathing a bit ragged. He pulled his thumb out and replaced it with another finger, longer, not much slimmer and that reached even deeper inside me. As he stroked me from within, he started pushing another finger against my taut entrance.
Thanks to the oil, he pushed that finger in too, soon enough. My hands were clenched on the sheets, my heart thudding and my nose and mouth full of the nutty, sweet scent of the oil he was using.
He turned his fingers, curled them and slowly pushed them in and slid them out of me.
The pain was there again, I could feel my skin stretching around his intrusion and my ring clenching around his fingers trying to push him out… but I could also feel him inside me, his exploring fingers sometimes sending a hard shiver up my spine with a flash of liquid sensation.
I was painfully hard and wanted more of him.
He finger-fucked me for what seemed a long while. How long, I am not sure; I could only concentrate on his fingers inside me and the contrasting caress of his hand over my back and cheek as he whispered how much he wanted me. At some point he added a third finger to his ministrations- I stretched further to accommodate him and whimpered a bit even as I spread my legs even further to invite him in.
I was rocking against his hand and against the mattress. I could feel sticky warmth growing under me as I gasped in shallow breaths and lifted my hips up to meet his hands, seeking those rare moments where he sent a long shudder up my spine that blocked out the discomfort of my flesh being stretched to its limit. I felt his every movement as he filled me.
When he slipped his fingers out of me, I collapsed on the mattress, panting. I felt empty and strange, my flesh burning and aching from the invasion even as I longed for more. When I felt him move behind and over me, I tensed once more- in anticipation.
I glanced over my shoulder as best I could to watch him step out of his briefs. I could not make out details without turning around, and the last thing in the world I wanted right then was to turn around. He went down to his knees between my legs and I lifted my hips toward him in a clear invitation. I felt his thighs brush mine and I shifted to rest my feet against his calves. I felt his arms on either side of my shoulders and I clenched my hands again into the sheets- I was almost gasping for breath as he shifted his weight forward, still murmuring how much he wanted me and how he loved my body; his scent was all around me, the slight tang of sweat faint in the mix of nut scent from the oil and the richer but more subtle smell of his skin.
He brushed against my ring- still slightly open, muscles tired by his fingers- with the broad, blunt head of his cock. I groaned and pushed back against him even as I involuntarily clenched against his new invasion. He kissed my shoulder and the back of my neck as he laid more of his weight on me.
He shifted his weight to one arm and I felt his hand parting my cheeks and guiding his shaft to push and probe against my tightening flesh. I could feel the very tip of his cock trying to force my slightly parted hole wider, without success.
After a minute or so of trying he rose to his knees and I sighed with disappointment, letting my head drop on the bed. When I felt him rise to his feet I reluctantly pushed myself up on my knees, ready to finish him off as I had my previous would-be lover.
“Get up,” he said. His voice was husky and soft, fitting of his online nickname. I did so, giving him a confused glance- he smiled and placed a hand on my shoulder, turning me away from him once more. “Bend over, baby,” he then said as he placed his other hand on my hip and encouraged me to do as he said…
“Bend over, baby,” he said as he placed his other hand on my hip and encouraged me to do as he said. He had started to take my virginity and wanted to finish what he’d started.
I parted my legs for balance and bent over at the waist, the rush of anticipation returning. I didn’t know then what difference having me stand up would make, but if he was willing to try again, I certainly was. Legs parted, one hand on the wall and the other on my thigh, I tried unsuccessfully to look back at him over my shoulder.
He had poured more oil on his hand. I could see his arm moving and hear the wet, squelching sound as izmit kendi evi olan escort he rubbed the oil on his cock- a wave of the by now familiar smell of it reached my nose as he stepped forward again and grabbed my hip with a warm, wet hand that was still dripping oil.
I could feel a cooling, slowly evaporating drop roll down my leg as he stepped up closer behind me.
“Open your legs a little more…” I did so, lowering my hips slightly. “Good, there…”
I felt his hand parting my cheeks again, guiding himself to push against my clenched knot.
He dug his fingers into my hip and moved forward as he pulled my hips back to meet him. His head slid along my crack, he pushed and rubbed it against the muscle keeping him out. Standing, I could not clench as tight- my tight entrance started to give way.
He felt that and whispered I should relax as he pressed on. I hissed and grunted as I felt him start to enter me.
He pushed his big, bulbous head against my stretching ring and through: it hurt and burned far more than when he’d finger-fucked me, it felt as if my flesh would tear. I had both hands pressed to the wall by then, elbows bent and cheek pressed against the cool surface in contrast to the searing pain in my ass as he pressed on. I whimpered and breathed fast and shallow, my nose full of the smell of plaster. Just before I begged him to stop, his head slipped fully inside me. My ass closed up around his shaft, the blinding pain turning to a more bearable ache and a sharp awareness of him being inside me. He felt me relax and sag against the wall and asked if he should stop…
“No, god no… Don’t stop now,” I mumbled against the wall as I caught my breath.
He placed both hands on my hips then, shifted a bit and grunted as he started to shove his length into me. I groaned and hissed as I felt him push deeper into my insides; I felt his every ridge and vein as he forced his cock past my bruised, stretched ring.
I could feel him fill me, cramming me and claiming me as he whispered breathless reassurances and drove his length into my depths. I could not get away, held by his hands and pressed against the wall.
And then, finally, he was there. I could feel his thighs against the back of mine and the soft caress of his pubic hair against my butt. He eased his hold on my hips, caressing my lower back with one hand as he too caught his breath.
Still whispering reassurances, telling me how good I felt and how the pain would go away, he rotated his hips and ground against me, moving his cock within me and making me groan, clench my eyes… and clench my ass tight around his cock, making him moan.
With his hand on my hip and caressing my back and side, he started to pull out slowly. I felt every inch as he withdrew, the feel of his flesh sliding out sending an odd shiver up my spine and making me gasp in surprise instead of pain.
When he was about halfway out, he pulled me away from the wall and guided me- bent over, staggering and with half his meat still plunged within me- back to the bed.
Every step and every movement had me wincing, ripples of pain and sensation running through my body as he jerked and moved in my sore, sensitive ass. I almost collapsed to my knees on the low mattress; he gently but insistently pushed my head down to rest on the sheets.
I could smell my sweat and the near-sour smell of my own seed from earlier. It drowned the smell of the oil, clung to the back of my throat with every breath as he crouched behind me and then shifted onto one knee.
He pushed back into me, using the leverage of his position to go even deeper. I groaned and he grunted until his hips were pressed hard against mine. The pain was less as my ring was starting to numb from the constant pressure… but I could feel him slide out again, a contrasting caress that sent new shudders up the length of my spine and down into my balls- a tingling shiver that made my cock twitch.
He drove slowly into me a few more times- the painful breach of my bowels as he rocked his hips side to side followed by the stroke of his withdrawal that had me gasping and moaning against the sheets. Then he leaned in, and whispered to me…
“I want to turn you over, baby; I want you on your back…”
I would have agreed to anything at that point.
I babbled something in response and shifted my weight to the side; he leaned back and helped me lift my leg as I rolled onto my back. There was a new jab of sharp pain as my movement yanked his cock out of me, his wide head once more tearing at my ass on its way out.
As I lay on my back, breathing hard and with a damp smudge on my cheek reeking of my own excitement, he kneeled between my legs and looked down on me with that soft smile. He had something in his hand- it had not even occurred to me, but he’d brought a condom. I watched him rip the packet open and reach down to put it on- I managed to lean up enough to watch him do it.
His cock was dark and glistening, thick and pointing at my face. He was noticeably bigger than me, his mushroom head looking huge even at the end of his thick shaft. He rolled the thin rubber down almost to his dense nest of black, tightly curled hair.