I remember it like it was yesterday, although it’s been many moons ago…. I still on occasion crave it again, the excitement, the rush but most of all, the pleasure…. This was back when Yahoo Dating still existed, I had never even considered being with another man, although I had used toys before that, small vibrators while getting a BJ, or during masturbation… back then, I was working from sun up to practically sun up the next day many days, which, as I’m sure you can imagine, wreaked havoc on my social life. I used Yahoo dating as a way to pass time, as I rarely if ever had a chance to actually go on a date, it was still great to chat with women, trade pictures and fill the void in my heart of not having a relationship…. As usual, I slacked on my profile and never set up any “guidelines”, it was available for all to see, males or females of any orientation and as fate would have it, I recieved a message from, let’s call him “Byron” towards the end of the evening, simply titled “Hi”, I didn’t think about the profile parameters, so wondered why and how I was recieveing messages from another guy, so I opened it, read through the pleasantries to where it said he recognized me from where I worked and wanted to hang out one evening. His profile didn’t say “gay” or “bi” at the time and he didn’t mention a “date” so I thought he recognized me, was bored and just wanted to hang out, I remembered who he was, he had always been nice and we always shared great conversation, so he showed up that same evening as we were about to finally get out of work around 1am…. asked if I wanted to go to a strip bar down the street, I wasn’t doing much else and decided to go… we sat down, he had a few beers (I don’t drink) and we got a few lap dances from the ladies there…. and ended up taking one back to my place and had a 3some with her…. She was adventurous, doing things I’d never done before, split roasting, DP, DVP and more, until we were done and fell asleep in a naked pile on the bed. I felt the bed moving as I looked over and saw her getting up to get dressed and leave, I watched her through cracked eyes, her large tits swaying, her heart shaped ass jiggling as she slid her thongs passed her curves and finally out the door with her shoes in her hand and I went back to sleep… maybe an hour or two later, I feel something wet and warm around my cock, my eyes crack open thinking the stripper came back and I see Byron, sucking on me…. it felt so damn good, much better than what she had done just a few hours before, so, I pretended not to notice and closed my eyes while I imagined her, until he shifted over and straddled my face… his cock brushing my lips. He was much larger and thicker than myself, borderline of what I’d call huge…. I hesitated, at first in protest but eventually gave in and stretched my mouth over the tip of his cock, he hit the bottom of mine as soon as I did, but I didn’t think I could his, it was just too massive, I grabbed his balls and massaged them, rolling them around in my palm as my other hand jerked his shaft while I sucked the head of his swollen cock… his thrusts got more aggressive and eventually my nose was buried in his balls and I was at the base of his shaft while we 69’d…. I eventually came and he swallowed every bit of it…. my guilt and shame finally washed over me and I stopped sucking his cock even though he hadn’t finished yet and rolled over… about 30 minutes had passed and I was slowly falling asleep again until I felt him “spooning” against me… I didn’t say anything I felt guilty about not allowing him to cum, so just layed there on my side. His cock growing against me and in between my cheeks as he started to grind through my crack and against my asshole…. I can’t deny it at all, I was sort of turned on, I’m not sure if it was the pleasure of him grinding against me or the fact that I knew I was what turned him on, but I arched my back a little to allow him easier motion, I could feel his pre-cum between my ass cheeks, sticky, warm and slick, like warm honey, using his fingers to press his shaft and head harder against my tight virgin hole, I offered no resistance, I tried to relax until I felt the initial pressure against my opening… it shocked me… it hurt a little, his girth was monstrous and something I had never experienced before, but I felt the head of his cock finally push inside me,the ridge of his cock just past my needy ring, i felt every detail… still laying on our sides, I stiffened up, grabbed my right cheek and spread it just a little, he pushed in a little further, then pulled it out completely… at this point, I was all in…. I got on all fours, he positioned himself behind me, my face on a pillow, his hands spreading my ass apart, he struggled to go inside me, I reached over to the night stand beside the bed where the KY was from the DP with the stripper and he put a heaping amount around my entrance with just a little on his tip and eased it back inside…. there wasn’t enough lube to make it sloppy as there was still enough resistance to make me whence as he slid it in… inch by inch by inch until I felt his balls against mine…. my eyes bulging at this point, I wasn’t prepared, it felt even larger than it looked, which I’m sure isn’t a normal size to begin with, I felt full, a little pain, but as he slowly slid back out I wanted more, just as I felt the tip of his cock near the end, I pushed back against him, engulfing his length, we kept that rhythm up for about 15 maybe 20 minutes as I relaxed and got more into it, as he pushed my body forward and away from his, I’d force myself back against his pelvis, fast and hard, the pleasure is unlike anything I’ve ever felt up to that point and never again, my arch was deep now, my shoulder now on the bed and my ass at full attention as I reached between my legs to grab his balls and guided him to the perfect pace and ocassionally my balls with his as he would grind against me deep…. I loudly whispered over my shoulder at him “don’t cum yet”….. “don’t cum yet” over and over….. I guess that sent him over the edge… his pace quickened and I begged him not to cum yet, i needed at least another 30 minutes….. I tightened my grip around his balls and thrust him faster and faster into me… the slapping noise of his thighs and pelvis against my ass filled the room…. he groaned and grunted and I felt my inside flush with his hot load…. he stopped moving… stayed there perfectly still, I still had his balls in my hand, I could feel him shrinking inside me…. I pressed back against him and felt him slide a little further inside me… I pulled away about an inch and could feel him almost slide out, I pushed back and could feel his limp cock get swallowed back into my ass…. I did this for a few more minutes until he was able to get a little hard again…. we played around for about another 10 or 15 minutes with him inside me, until the alarm went off for me to get ready for work…. we showered together… sucked each other’s cock in the shower…. he tried to fuck me in the shower again but being taller than him it just didn’t work out. We left, shook hands and went our separate ways…. i felt his cum leaking out of me the entire way to work, he called me two nights later to tell me he was getting stationed on the west coast and was leaving the very next weekend, we haven’t spoken since then… and I ache for another experience like that, but now, married with kids, life had different plans for me….
Wow, that’s great