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How a Formerly Straight Guy Began Having Sex with His Best Friend

By chgosub777

submitted June 18, 2010

Categories: Best Friends, Bisexual, First Time

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Ray and I had been best friends through most of high school and kept in touch after we turned 18 and went off to different colleges. When we came home the summer after freshman year we immediately began spending a lot of time together. We both worked construction that summer and got off work at 3:00 pm. Since my parents both worked, Ray would come by my place where we’d have a couple of beers and jerk off to my porn collection. We both liked to get completely naked to jerk off since it made us feel sexier and I even got turned on looking at Ray’s lean, tanned and muscular body and his big, thick richly veined penis. I often felt his eyes on me and he later admitted to feeling the same way I did. Even though we both loved fucking our girlfriends we gradually started getting sexually turned on by each other. Maybe jerking off with a good looking young guy will do that to any guy. We started timing our orgasms to come at the same time and we got pretty good at edging, getting right up to the point of coming and backing off just enough to hold off. As we both got right to the point of orgasm and we’d finally agree to let go, we would roll onto our sides to face each other and shoot our semen on each other’s body. After a few weeks of this, an afternoon came which changed our routine. Ray had told me when he arrived that he was feeling particularly horny and needed to jerk off right away. We went upstairs to my room, undressed and got in bed side by side. We didn’t even bother with porn this time. I figured we’d both jerk off fast and then get some beer and hang out before doing it again. Ray had a different plan. After a few minutes during which the only sound was our deep breathing and that distinctive sound your hand and cock make when you’re whacking it hard and fast, Ray reached over and put my hand on his cock and immediately took hold of mine. He broke the silence. “I’ve wanted to feel your cock for a long time. Is it okay if we jerk each other off?” “Uh yeah, I guess so….” I stammered. “Do you like the feel of my hard cock in your hand?” “Yes, it kinda turns me on,” I said without hesitation. “It’s cool that you’re left handed too. We can lie beside each other and both use our good hand. Otherwise one of us would have to lie in the other direction.” It occurred to me that Ray had either been thinking about this or had experience at it. It didn’t matter, I just knew that this felt hot to me and we both started working on each other’s dick. When I felt Ray’s warm semen flow onto my hand after the first strong spurts had shot, I loved it. Just before I came, Ray sensed it and slowed his hand. “I want to finish you off a special way,” he said grinning. I was stunned when he then leaned over me and took the tip of my cock between his lips, stunned but thrilled. Ray was soon on his knees beside me working my throbbing penis with his mouth and hand while his other hand started playing with my balls and asshole. I started arching myself off the bed, thrusting my hard cock into his hot wet mouth. I was out of my mind with pleasure and desire. Ray moved one hand softly across my belly and chest, stopping at one of my big erect nipples and started playing with it. The sensation shot straight to my crotch and I suddenly felt my ejaculation spasms shooting huge amounts of semen into Ray’s mouth. I heard gurgling noises coming from his throat as he swallowed it all. After sucking the last bits of juice out of my deflating cock, Ray surprised me again by stretching out on top of me. I felt his hard cock between my legs and pressing up into my scrotum. Even though I had just experienced the strongest orgasm of my life, I felt turned on by the pressure of his body and the feel of his penis against me. “How did you like that?”he asked, his face inches from mine. “I think you could tell by how much you had to swallow.” “Yeah, that was a HUGE load,” he said as he gave me a sexy dirty smile. “I liked it too. It’s fun sucking other guy’s cocks. But I have another big load I need to shoot. Do you want to try sucking my cock or would you rather let my fuck your ass?” Now THERE was a question I never expected to hear from a buddy! “Uh…I’ve never done either but I guess I’ll leave it up to you…” “Well then I’m gonna fuck your ass. I’ve wanted it since I first saw your cute ass in the shower room in high school. Don’t worry, I’ll take it slow. I want you to enjoy it. I plan on fucking you all summer long.” After I found a jar of Vaseline in my parents’ bathroom, Ray gently lubed my virgin anus with first one finger, soon followed by another and finally a third. As I got used to the sensation, he started finger fucking me and then twisted his hand as he thrust his fingers deeper and deeper into my ass. He watched my face closely while he was doing this and could see that I was really getting into it. Before mounting me, he slid up and presented me with his cock to take into my mouth. “I assume this is your first taste of cock. I think you’ll like it. Make it nice and wet before I stick it in your ass.” He was right. It felt thrilling to take a penis in my mouth, but he didn’t let me suck it long. He was impatient to get laid. “I’m going to do you missionary so I can see the look on your face as I slide my cock deeper and deeper inside you. Does the idea of having a hard cock in your ass turn you on?” “I’ve had fantasies about it and sometimes when I jerk off, I lick a finger and stick it up there as far as I can get it. It really feels good!” He put my ankles on his shoulders as he knelt over me so I was jackknifed, presenting my glistening rosebud anus to him. He took his cock in one hand and placed it right in the center. As he had promised he went very slowly and had done such a good job with his fingers that I could see the big knob entering smoothly and easily. I could feel my sphincter resisting but yielding to the penetration and I could hear myself moaning and sighing with pleasure. I sounded like a cunt, but I didn’t care. Once the big red knob of his penis had popped past the resistance of my sphincter and he had penetrated a little further, Ray started very gently and slowly to pump his hips back and forth just a bit. Each thrust forward took his cock a tiny bit farther into my rectum. This made penetration much easier and more comfortable and the friction of his pumping was starting to get me even more turned on. I reached for his ass and started pushing him deeper and deeper into me until suddenly he stopped, buried to his balls in my ass. We were both breathing hard at this point. Ray looked at me and again gave me a wonderfully dirty smile. “Now your good friend Ray is going to give you your first ass fucking.” Again he started with short strokes, withdrawing only a couple of inches before thrusting up against my ass cheeks. Gradually he lengthened the strokes until finally he was withdrawing all but the head of his penis before smoothly sliding the entire length back through my anus. On each stroke I involuntarily let out a little gasp or moan, the kind I liked hearing from women when I was in stride fucking them. I really was turning into a cunt. I guess getting fucked will do that to you. After fucking me like this for a good long while, Ray started playing around, changing his tempo, shortening his stroke and slamming his cock into me really hard. He seemed to really get off on hearing my gasps get louder as he started to jackrabbit fuck my ass. Then he slowed down a bit. “I want you to start squeezing your sphincter muscle on my cock really hard every now and then. The pressure feels really good.” I started doing that and was rewarded by sounds of pleasure from Ray. Again I thought of how I enjoyed fucking a cunt that could give my dick a really good squeeze. Finally, after my ass was totally opened up from having been fucked so long, Ray started withdrawing completely and then penetrating me all over again. The stimulation the big knob of his penis on my anus drove me crazy. I looked down and loved seeing how large his cock was and thrilled at the sight of disappearing into me again and again. By now Ray was covered in sweat and I was bathed in it. Our wet bodies were slipping and sliding against each other and when Ray rammed me now we were making liquid noises. I figured I’d see what a little nipple play would do to the stud between my legs, so I reached for his hard little buds and started gently pinching and tweaking them the way I like it done to me. Sure enough, he went crazy, slamming into my ass harder and faster than ever. “I’m not gonna be able to hold it”, he gasped. “Is it OK if I come?” I nodded slightly and soon he was overcome by his orgasm. As the first waves hit him he managed a couple more thrusts before collapsing on top of me as spurt after spurt of semen shot from his cock into my rectum. I was thrilled that I could feel his cock jerking inside me on each spasm. I put my arms around him and squeezed him at the same time I started strong squeezes of his cock with my ass. Eventually his breathing slowed but neither of us said a word. With a penis still deep inside me, my mind was racing, thinking about what had just happened and wondering about the future. Certainly Ray and I would have sex at every opportunity for the rest of the summer. I was already thinking about learning to suck cock really, really well, and wanting Ray to come in my mouth. As to the future, I had to figure out how to find the right guy to fuck me when I went back to college in the fall. I knew now that sex with hot men was going to be a big part of my life.


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