First Time Friday

This is a true story about a first time encounter and the process that led to it.

My first time was on a Friday. I was 23 years old and had been in a sexless relationship with a girl for several years and always sort-of knew that I was interested in guys. Often late at night I would find myself wandering off the straight porn sites onto the links for man on man action. I began to imagine that I was in the photos and wonder what it would be like. I fingered my tight, pink hole and found that I liked it. One day I even got up the nerve to buy a life size rubber dong, a set of training plugs, and a bottle of lube to try and loosen myself up. It wasn't as easy as it looked, but I did enjoy the plugs and my desire for the real thing grew with each explosion of my cock, emptying the contents of my balls onto my stomach and chest.

Eventually I began to look at the ads on craigslist. At first I just wanted to see what the scene was like around where I lived. I also used to masturbate to the photos of local men and the thought of what they proposed doing. Soon enough I began responding to ads, but would never follow through with any plans to meet as I was too afraid. I did have a great time taking photos of myself, specifically of my shaved bare cock and ass. I would stay home and jerk off to the thought of what men wanted to do with me. At one point the tension had built up so much that I actually drove over to some guys house who was going to blow me through a glory-hole he had set up near his front door. When I got to the house there were so many people outside in the neighborhood that it freaked me out and I kept driving. He was pissed, but I had developed such a raging hard-on knowing that some man wanted to gratify me by sucking my rock hard dick that I knew I had to release somehow.

I knew that there was a porn store not far from where I was which had video booths. I never went into one before this but I had an idea that it was a place where guys masturbate and cruise for other guys. I bought some tokens and went into a booth, closing the curtain as well as I could. When I walked into the booth there was a seat and a TV screen which is perpendicular to the hallway. No matter what I did, it wasn't possible to have complete privacy. But I had paid my money and my boner wasn't going away so I tried to relax and get going. I dropped a token in the machine and the screen before me came alive with a video of a teenage girl getting her pussy rammed by what looked to be a ten inch black cock. The cock was impressive, but I wasn't into her fake moaning so I flipped around. I saw some pretty hot lesbian scenes which only caused my bulge to increase with that signature spot of precum beginning to show through my gray gym shorts. I figured I'd better not let that get any worse so I whipped my dick out, without taking my shorts all the way off.

I felt a little weird about having my bare ass on the seat of such a grimy establishment, but my horniness had taken over so that concern was fleeting. I admired how big my dick looked, freshly shaven and hard. I'm not blessed with a huge cock (its only six inches), but sometimes when I'm really aroused it looks huge. I didn't have any lube so I spit on the head of my cock and began to move my hand over it in that old familiar motion. Between the porn getting old and the strangeness of jerking in such a bizarre place, I began to lose my hard-on.

I flipped through the channels until I came across the gay channels. One caught my eye, as it was another young redheaded guy like myself sandwiched between two hot skinny twinks. Immediately my rager returned and I began beating it furiously, imagining that I was the one between these two beautiful cocks, one pounding my ass and one in my mouth. In the ferocity of my masturbation, I didn't notice that the sound of the porn could be heard outside the booth and might attract a crowd of interested observers. In fact, once I turned the gay stuff on, a guy in his mid thirties came over to the crack in the curtain to see who was enjoying that kind of porn and how they were enjoying it. Apparently he liked what he saw because he stayed there eying me and my sex with his hand down his own shorts. I tried to ignore him and focus on the hot scene in front of me. I actually began to like that he was watching me; it made me that much hotter.

I pulled my shorts to my ankles and shifted my hips so that he could get the full view of my hard member and glistening, hairless balls, all the while never letting my eyes leave the screen or my hand leave my cock. The scene on the screen began to intensify as the lucky redhead's moans told me he was close to climax. Suddenly the curtain pulled open and there were now four guys watching me, two of them with their dicks in their hands, watching only me. The fact that I was being watched by these men and that they were stroking their cocks to me was too much to handle. Just as the redhead on the screen exploded all over the pillow he was being fucked over, my cock tensed and shot my white hot cum up onto my t-shirt, with a small drop landing conveniently on my lower lip. I looked at the men who had been watching me and quickly swallowed the droplet of jism that reached my face, enjoying its texture and salty flavor. One of the men reached out and stuck his finger in a wad of my cum that was hanging from my shirt, tasting it like he had just tasted home made gravy. He simply nodded, indicating that he enjoyed the taste of my spunk.

With that the blood finally rushed back to my head and I began to think about the absurdity of this situation. I pulled my shorts up and ran to the bathroom to wash my hands and dick. I quickly left the porn store and drove home, trying not to think about the experience. But it wasn't that easy. All I could think about for the next week was the sexy redhead, his balls exploding because of the stimulation of a long, hard cock ramming his tight, pink asshole. And the men who enjoyed me, enjoying myself and the redhead. I was determined to feel what that redhead felt. I wanted to be that redhead. All week at work I thought about it, delaying standing up so that my erection could go down.

Finally, on Friday, I had to have it. I knew that there was a guy interested in me from craigslist. He saw several of my photos and liked my hairless, boyish physique, and small dick. He fashioned himself a versatile oral top, who was an expert at dealing with newbies. He was twice my age and worked from home in a town that was not too far but just far enough away from where I lived that I wouldn't see anyone I knew on the street. I set up a meeting for that afternoon.

I nervously drove the half hour to his house. I told him that I was only interested in getting a blowjob, knowing that once naked, he would probably push to fuck me, as I had done with so many girls. I pulled up to his house and quickly ran up the walkway. I waited nervously after I rang the doorbell for him to answer. Finally, he came to the door. He let me inside and looked me over. He was a large man; not fat, but much bigger and stronger than me. He was several inches taller than me and clean shaven with his silver hair neatly cut. He pulled me in and groped my ass and could tell that I was really nervous. He led me up to his bedroom, put on some gay porn and dimmed the lights. Again he held and groped me, trying to get me to relax. I wasn't hard because of my nervousness when he grabbed for my dick and eventually took down my pants and boxers.

He then took off his pants and grabbed both our cocks with one hand, massaging them together. He sucked one of my nipples and worked his way down to my dick. He briefly marveled at the job I had done shaving that morning. With a sudden burst of enthusiasm he took my half-hard prick in his mouth, sucking my dick until full erection. He moved his tongue around my balls, rolling them over and over with a simple flick of wetness. He clenched my ass with both hands and slipped a finger down its crack, grazing over my clean, smooth boy hole. He brought me over to the bed and had me lie down on my back. He moved between my legs and began to suck me while I watched what was becoming a hotter and hotter scene on the porno flick he put on. He asked me if anyone had ever played with my ass and I told him honestly that only I had.

He smiled and correctly said that means that I've had dreams of being fucked. I didn't say anything but rolled my eyes back in my head while my back arched, throwing my head deeper into the pillow as he spread my cheeks apart and flicked my soft hole with his talented tongue. With his strong hand gripping my dripping penis, I almost exploded as he delved deeper into my anus with his mouth. He recognized my excitement and backed off a bit, returning his lips to the head of my throbbing cock. I relaxed a bit and suddenly he began to move his fingers around my moist hole, slowly slipping his index finger in an out of its pink, rosy entrance.

He took a break from sucking and fingering to get some lube. I became excited because I now knew for sure where this was going. He carefully and patiently worked my hole, spreading it apart and licking and fingering while I held my legs behind my head. He moved his fingers in and out, and took the index finger of each hand and gently pulled my hole wider. At this point, both he and I knew that I was ready. He knelt and moved up closer so that his beautiful, thick seven inch cock was closer to me. I reached out and held it in my hand, feeling it pulse and move with excitement.

I had never even touched another man's cock up until this point, so I figured I'd go for the gusto since this was my chance. I pulled my head closer to his package and just impaled mouth on his rigid member. It was different than I thought it would be, but not in a bad way. His cock filled my mouth as I took the time to explore its head and work my tongue down the root and eventually around his large, masculine balls. As I did this, he reached for my hole, continuing to work it with his finger to ensure I would be ready to take him. Each time he hit my prostate I quivered and my cock jumped. When I tasted the sweet and salty taste of his precum in my mouth I wondered who was more excited.

As I was no expert in the field of giving head, I thought it was time for both his and my enjoyment to move to the main event. I released him from my mouth and he moved back between my legs, grabbing my ankles and forcing them up behind my ears. He squirted some lube directly onto my puckered hole and began to rub his dick across my tender opening. Slowly, almost without notice, he began to apply some pressure downward on my boyhole. At first it felt alright, until his entire girth was pressing through my opening. The pain was like a burning, but it was bearable. He calmly told me to relax, which I did, and my ass began to suck his cock deeper inside. As I relaxed the pain lessened and he was able to move vigorously in my hole. With each thrust it became more comfortable and he came closer to hitting that heavenly spot. I looked in the mirror and watched as his dark, tanned skin contrasted with my powder-white, slightly freckled completion, his cock entering me over and over, my balls bouncing with each impact.

I thought my cock would burst as I gripped it with my right hand. With my left hand I spread my left cheek so that he could penetrate deeper into my pleasure zone. The momentum of his thrusts meant that I didn't have to move my hand to stimulate my throbbing prick. In no time I was ready to explode.

As the sputum shot through my balls and up to the head of my fountain, my hole began to expand and contract with the intensity of my orgasm. He looked down to see my cum showering the both of us and felt me closing around his massive dick and immediately threw his head back and forced himself as deep into me as he could, unloading his seed while letting out a hellacious yell.

He waited for his dick to soften a bit and withdrew it quickly from by leaking boyhole. He licked my cum off of my chest and worked his way to my cock. He sucked every last drip from my now flaccid penis and followed that by licking his own jizz from my dripping, tender hole. The feeling was euphoric.

After he had cleaned me as best he could he offered me a shower and towel. I declined as he had done such an excellent job cleaning me and quickly dressed as I wanted to be alone to reconsider my new sexual experience. He told me to hold on to his email address and contact him any time I wanted to get off, which I assured him I would. As I walked out the door he said to have a good weekend, and I thought, it's only Friday and this has already been a great weekend.