tagGay MaleAll My First Times

All My First Times

byCronicCruiser©

When it Began

I rang the doorbell. I was on the job delivering pizza to an apartment in a high rise complex. A late 20ish Arab dude opens the door. He's in a one piece white robe looking very Middle Eastern. I hand off the pie. He sets it down and he gives me enough money to cover pizza.

Then he takes out an extra twenty and pushes it into my front pocket. I see it coming but I freeze up not knowing what to do. He lingers resting his fingers in my front pocket against my thigh. I'm still just standing there my mind racing. I know it's a sexual act or at least it was to me. I was young and my cock was rock hard from the moment he pushed those finger along my thigh inside the pocket. He withdrew his hand from my pocket and pulled out another twenty. He fingered the new twenty and slid it into the top of my pants. His digits push down inside my jeans and over my underwear making contact my boner. Now he knows how turned on I am.

I'm still frozen in fear and arousal standing silently in the entryway. I would not speak thru the whole encounter. He pulls his hand out of my pants and I let him unbutton my jeans and open my fly. He pressed his palm over by engorged penis and then pushes my underwear down enough for my erection to pop out to attention. He grabs ahold of my cock and I have a rush of excitement. To this point I'd never really thought about if or how far I'd go with another guy. The only gay fantasies I had involved the gay gloryholes I'd read about and I when I wacked to them always pictured chicks on the other side. Now I had a dude giving me a hand job and I didn't want him to stop.

He only played with my cock for a few short strokes. Holding me by my cock he pulls me to the bathroom. Once in the bathroom he pulls his white robe over his head and revels his naked body and his erect penis. I don't notice much about him because I'm totally focused on his dick. It's bigger but not longer than mine dark skinned and uncut. He'd dragged me to the bathroom but I'm still just flooded with adrenalin, horny as hell and full of fear unable to move and not sure what to do next. Now secluded in the bathroom he proceeded to push down my pants down. For a brief time he held our cocks one in each hand stroking them. When he release his grip on our dicks he guided my hand to his cock.

I grabbed ahold and stroked the first hard cock I'd ever seen. I was fascinated by the way the foreskin uncovered and then concealed the head as I pumped it. He didn't take too much time till he grabbed the back of my head and pushed my face to his penis. I was so happy wanking him and would have gladly wacked him off but putting a cock in my mouth seemed out of the question for me. He pushed but I resisted. He released me and I stood back up and I continued to stroke his cock while he handled mine. He turned to the sink next to us and lost my grip on his cock. He made up some soapy water and gripped his cock with it. I had no idea what he's up. I figured he was cleaning it for me to suck. I was too turned on to stop but still not sure I would blow him. He turned me around and before I understood what was coming he pressed his soapy boner up against my bunghole. The uncut head pressed up to my hole felt wonderful. He had ahold of my cock and I was very close to cuming.

Then he forced himself inside me. I felt the stabbing pain of having a fully erect penis shoved up into my tight virgin asshole and I just jerked away. His shaft slid out of me. I was not ready or willing to get fucked up the ass. Now that I'd realized there was no way I wanted him to fuck me. I immediately decided the blow job was the better option and decided to try to suck his dick which was now covered with soap and ass. My thinking was that had to rinse him off so I could enjoy sucking his penis. I was still so shook up and dry mouthed that I couldn't speak. He didn't get my move to turn on the sink to rinse off his dick and it spooked him. He rushed to put his robe back on and I pulled up my pants and I left in a hurry. Neither of us was willing to say anything and so our encounter ended without a happy ending.

I'll always regret not sucking and not fucking that Arab dude, but I wasn't through yet. I worked the rest of my shift and planned what I would do next. I had been so turned on by my encounter that I had to get more and I knew how and where I had to go to get it. The local adult book store might just have those gloryholes I'd read about.

I had only recently turned 18 and I'd never been in this book store before. I'd seen empty gloryholes in my only previous visit to a different dirty book store a few months before. I walked back into the arcade. I wanted a blow job and I wanted it now. There were a few guys hanging around the outside of the booths and most of the booths had the light on and seemed occupied. I had a little change in my pocket so when I got into an empty booth I popped in a quarter and the movie started. I had no interest in the movie.

I was in luck the booth had gloryholes in both adjoining walls. There was light in the booth to my right and I stared thru the gloryhole and watched in amazement as the dude in the booth stroked his wood. He turned his dick at the gloryhole and I shook in excitement as it approached the hole. I had been focused on getting my cock sucked but when this 6 inch hard-on came thru the hole I knew I was going to put it in my mouth. I grabbed the shaft and held his cock tight. I stroked and explored it with my hands. Soon I kneeled down and faced the one eyed head of his cut cock. The dick bounced up a little on its own as if to say "suck me." I opened wide and took the enlarged head of his dick into my mouth. It was smooth and warm and the taste was so arousing. I explored the tip and hole of his rock hard cock with my tongue. I pulled back to look at how beautiful it was and measure it up for a deeper trip into my mouth. When I did, he pulled back and gave me the finger.

I instantly knew what the finger meant and pushed my cock all the way thru the hole. I was going to get the blow job I so wanted. He made no attempt to handle my manhood. My penis went right thru the gloryhole and he enveloped my cock with his warm wet mouth. I pushed forward till my cock slid all the way thru the hole. I felt his beard against my balls. I was so turned on I came instantly. My knees rattled against the wall and I moaned out of control. I was consumed by the most powerful orgasm I'd ever had. My load sprayed from my dick and he took it all sucking me harder as I dumped by seed. My legs no longer supported me and I fell back into the chair in my booth. My first blowjob was a smashing success and to think I could come back for more anytime I wanted. I sat half naked in the chair very pleased with myself.

My movie had ended and I was just sitting in the dark. I saw the light come on in the booth to my left. I watched thru the gloryhole as the newcomer undid his pants, push down his drawers and unveiled his penis. He took himself in hand and started to jack off. My first two cocks had been hard at first sight. I was disappointed as this one was soft and looked too small. It didn't take long for him to get himself hard. I watched his cock grow to an erection as he stroked himself. He turned his dick to face the hole and pushed his penis thru to me. I could clearly see now that this cock was big, much bigger than the others. It approached 8 inches in length and was thin for its length. When I took his cock into my mouth, it wasn't quite hard which allowed me to get around it and into my mouth for some licking and sucking. He let me play with and suck on his cock for quite some time. I wanted to please him but I wasn't ready to have him or anyone else brick in my mouth. I was a little relieved when he drew his cock back and signaled me to use the hole. I had just cum less than half an hour earlier but I was so horny that I was already hard again. My second blowjob lasted much longer than the first. I was able to last for several minutes before I launched my little lob of sloppy second cum into his hungry mouth. I was hooked though I'd would not have two squirts in one trip again for a long time.

I would be back again and again. Afterwards, I'd visit the holes as often as I could. My first visit established my pattern. I would look for other guys with boners. Only hook up with other guys with hard-ons either thru the holes on in the booths. I always delivered my load as long as my boner buddy would let me suck his cock a little first I'd cum in his mouth or ass weather he liked it or not.

The Next Level

I was heavy into a suck and suck with another young dude my age. Passing my cock to him and sucking his dick thru the hole in return. He pulled back and spoke to me asking if I wanted to come back to his place. I took the offer right away. I'd been having gloryhole and booth sex. No chance for some of the more comfortable and kinky positions and it seemed like a good chance to explore more types of man sex.

We met up at his dorm room a short distance away. Without much talking, we both stripped down and laid down next to each other on his bed. I hadn't been nude during sex before and was enjoying all the extra skin contact as we took turns blowing each other. That led us to a 69 position I'd always wanted to try. He climbed on top and lowered his dick into my mouth as he pulled my cock up into his lips and I gleefully sucked his manhood mirroring his moves on my boner. Our cocks we very similar in size and I had no trouble getting all of his cock into my mouth which worked out as he forced himself completely down to my throat. After enjoying the 69 he rolled off me and onto his back where I continued to suck his cock. He rolled his legs up and got me between them. I was so happy. He wanted to me fuck him up the ass. My boner was hungry for its first hole and totally hardened for rear entry.

With just a little spit he worked my cock into his ass. It was such a tight fit that it was hard to move my cock in very deep and it was not very pleasurable. I remember clearly watching my dick disappearing up his hole wanting so bad to start humping. It took a time for him to get loose. It being my first time I didn't understand the way the sphincter works when penetrated. As his man cunt loosened up I was able to get my groove on pounding his ass. I'm sure in only took a short time for me to cum in his ass after I got to fucking it. I remember holding my cock inside him and felling the cum ooze back around my cock. When I pulled out my cock was covered in cum. If only I'd thought to use it as lube for want came next.

Once I was finished fucking him, we exchanged places. I held my legs up and let him position his boner at my hole. Like the first time I'd tried to fuck, his cock head felt so good all soft and warm pressing my hole. Then came the pain of entry. I watched as his stiff manhood bent back struggling to enter into my hole. He forced the helmet of his cock thru my pink hole which hurt a lot. Once his shaft was inside me, he continued and it hurt real bad. He pushed more of himself inside grinding against the dry hole until he was fully inserted. I wanted to make him cum but it hurt so much. I lasted only a few strokes before I had to have him pull out. He grabbed his cock and stoked it. I really wanted him back inside me to return the favor and cum inside me.

He knelt poised for reentry whacking himself between my legs. Before I could let him know that despite the pain and my softening cock, I wanted him back inside me, He came launching a jet of his seed up for a landing on my chest and splattering spouge onto my face. I had never seen a cum shot in person before and wow. The visible manifestation of orgasm squirting right into my gaze. He sprayed a couple more streams up my belly and to my chest. I was so cool to have his juice all over me I started to play with it enjoying the experience before he cleaned me off with a towel. We rested together nude on his bed for a while after but neither of us was ready for a second round. This remains the only time I had sex with a man in private. All the rest of my gay sex has been in public places.

Top Upside Down

I did many visits to the dirty bookstore as only a top. I'd look for guys with boners tease them a bit with my mouth and let have my load. I'd try to hold out for anal but usually settled for head. I knew there were more bottoms then tops at the gloryholes but most wouldn't or couldn't display my required erection. I never did anything unless his cock was out too. I began to wonder why so many bottoms? Getting head and occasional anal was so awesome. Why would so many guys be more interested in the bottom?

At this point I'd had plenty of cocks in my mouth. Some big some small but only a tease to them. I did it to get me hard and ready to deliver my cum once we switched to my dick. I thought increasing more about letting a cock cum into my mouth but had shied away before it went too far. I decided before I got there, this trip I was determined to suck until completion. I waited alone in my booth. It was not uncommon to strike out at the arcade and it seemed like no one was going to join me. There were other dudes there but none in the glory holes.

I was going to give up very soon when I was joined by a man in the adjoining booth. I watched him unveil his cock. Opening his fly and letting his dick out to play. I watched him stoke himself with my face close to the gloryhole. He showed it off a little as it hardened. I gave him the finger and once again I watched as the cock turned towards me and moved ever closer to the gloryhole. I took him into my mouth right away no hands needed. His cock was only extended only a few inches into my booth andit was easy to get it all into my mouth. My nose hit the wall as I bobbed my head. I had been afraid of what would happen if I went too far. This time I just went too far. I licked his shaft as I moved my head. I let him pump his cock into my face. My altered intentions fill me with anticipation of his orgasm and its salty discharge. I pumped his penis with my head and tongue. I brought my hand up and started pumping trying to hold the tip in my mouth but just wasn't long enough. I had my mouth right in front his dick getting ready to take it back into my mouth. He came as I watched. His semen dripped out of the tip following down over my fingers. It kept flowing making a real mess down my arm. The load was thick and gooey and was all over my hand and wrist. I was disappointed, the plan was for him to cum in my mouth.

He withdrew from the hole zipped up and left. My first thought was to eat the load off my hand and arm. I licked a glob off my arm. It was nasty and the nastiness was so turning me on. I tasted a little more. I had a lot of it on my hand and reached down and stoked my hard cock as I savored the cum I had tasted. The feel of that cum on my shaft was awesome. I discovered warm fresh cum is the best lube ever and I had a good handful to work with. I would have shot my load but I was interrupted by a new visitor in the next booth.

I had another chance to get cum in my mouth. I was in a hurry and I signaled him as soon as I saw his cock. He obliged and I took his cock into my mouth as he pushed it thru the hole. He'd dropped his pants and his large balls were visible thru the hole not quite close enough to taste. His dick was thick for its length. He had just barely enough length to get thru the hole and still have something to suck. This time I kept his cock in my mouth the whole time. I sucked it while stoking the shaft with my tongue. I gave his penis the full business as I beat the cum from my first blowjob. He didn't take long. The tip of his penis was on top of the tip of my tongue as it happened. I could feel the warm goo gush out along my tongue. It filled my mouth and dribbled out around my lips. I had to decide to spit or swallow after the first spasm of cum. I let his man juice drip out of my mouth to the floor. Then I had to swallow anyways so I could suck in the last drops of cum and clean him off. When he pulled his cock back from the hole, I had already cum allover myself. Now I knew why there were so many bottoms.

Bottoms have to do Anal

I went back to the same place I'd given my first blowjobs. Back looking to suck off more some cocks. I'd had a run of visits with cocks to suck and I was real horny and ready for some action. I choose a booth next to one that was occupied. I closed the door and looked thru the hole. In the next booth my new friend looked nude. His hard-on stood out by itself. He waved it around for me showing off his boner and I gave him the signal. His cock came through the gloryhole and it was grand. Large, thick, uncut and straight. He was fully erect and there was plenty to feast on. I took him in my mouth determined to make him cum. I dropped my pants so I could wack off as I blew him. After lengthy slurping he pulled his cock back and signaled for my cock. I was very turned on by the blowjob. His dick was so nice I didn't want him to take it back. But I gladly fed him my cock and gave me some great head. The hole was big enough for him to lick my balls as well. I was going to signal for his cock when he tried to turn me around. He couldn't force me to turn around thru the hole but I turned around for him and pushed my ass to the gloryhole. I waited for a moment thinking I'm so turned on, will I really let him fuck me?

Then his tongue touched my bunghole. Shivers when down my spine and my ass tingled as he pushed his tongue around my hole and then inside. Oh bliss, soft warmth caressing the inside of my hole. I opened my legs and push as much ass up to hole as I could. I'd been partially fucked and I'd been fingered before but this was fantastic. In all that pleasure I didn't really notice it was the tip of his penis pleasuring my hole. He pressed his dick head gently on my man cunt. I realized what he was doing and just let him do it.

His head popped inside me. The intense pleasure was wiped away and it hurt. He held his cock inside me briefly and then withdrew. Once again the soft cock tip massaged my bung before penetrating me again. This time his cock slid right in. The shaft felt better than the tip as he slowly stroked deeper each time till he'd put as much cock in my ass at the wall between us allowed. After he'd opened me up, the pleasure of penetration was washing over me with each thrust. I picked up the pace by rocking back into his thrusts. I was in ecstasy. I wasn't touching my cock but it was still rock hard and I was so close to orgasm. His cock pulled out of my ass. I was empty. "Put it back in" I thought but his hand pushed me back and he fingered me to feed him my cock. I was already close but placing my dick in his waiting mouth sent me over the edge and he took my load and gobbled it down. I don't know how he knew I was ready to cum but it so worked. I don't think he came inside me but I was hooked on anal from that moment on.

The Last Vale

It was a small dark theatre. Lit only by the gay porn showing on the screen in front. One isle down the center with 3 or 4 seats on either side. The back of the room was dark and there were several guys hanging out in the shadows. In the middle of the theatre two guys sat together and one guy was sitting alone in front of them. I walked down the isle to the row where the one dude sat alone. I could see that couple behind him were engaged in some well lubricated fisting sitting side by side with the bottom holding his legs back to his chest to provide anal access to his partner.

The dude alone had his cock out and was pleasuring himself as I shuffled in, dropped my pants and sat down beside him. We watched each other jerk off until he released his prick and gave me a good look at his penis. He was on the large side but the helmet was enormous. It was uncut and the vast outline of the head was visible even though the foreskin covered it completely. I released my cock and moved my hand over to his pole. He had a lot of foreskin but I pulled it all back to see his great purple head. I dropped my head into his lap and swallowed his cock. I pushed the giant head into my throat till I could take no more. I pulled up and the head was once more covered in foreskin. He went down on me and toyed with my cock. I let him suck me but he wasn't in it for the cum. When he pulled his head up from my cock he pushed his hand back along the seat and under my ass. He squeezed my checks and let me know he wanted to fuck.

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byCronicCruiser© 7 comments/ 35388 views/ 18 favorites

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