Ryan was a sexy, slutty, cock-crazy whore and our college buddies loved him for it. During my freshman year at university, he was having sex with Tony, my old High School sweetheart, before he had sex with me. In fact, I have Tony to thank for getting Ryan and me together: he told Ryan that I was gay, had a big dick, and that I loved to fuck guys. Within a day of being told that, Ryan marched straight up to me as I entered our dorm and was very aggressive with me, demanding that I follow him to his room and “fuck his brains out.” I obliged and it was one of the most exciting experiences of my life.
I guess I really should describe Ryan: he was very cute in the face, had a killer smile complete with dimples, moderately thin lips, a small nose, dark brown hair, hazel eyes, and thin eyebrows,. He was super skinny (his ribs always showed, even while standing), was super short (about 5’5”), was super smooth (no hair other than on his head … including his crotch, which he kept saved), and was very lightly muscled. Ryan had a lean torso, long neck, narrow shoulders, narrow hips, and short arms and legs. He was very flexible (he could lean over (with a little help) and suck his own cock and lick his own balls and even rim his own asshole). All throughout college, and for the several years I knew him afterwards, Ryan remained the quintessential and perpetual twink. He weighed about 95 pounds, and even later when he started to tone up his muscles a bit, I don’t think he ever made it over 105 pounds. Even though he could eat enough pizza to feed an army, he had NO fat on his frame at all. Up to that time, I thought he was one of the sexiest guys I’d ever seen.
The first time we had sex I remember Ryan making me sit on an ugly, green, vinyl bean bag chair in the corner of his dorm room as he slowly took his clothes off while dancing to “Loving, Touching, and Squeezing” by Journey. As each piece of his clothing came off, I got more and more excited, and my cock got harder, longer, and thicker, straining my pants. Once Ryan was naked, he dropped to his knees in front of me, zipped open my jeans, and put a hand in to work through my underwear fly and touch my dick. He remarked about how hot it was, and that was about all I could take. I suddenly stood up, dropped my pants, and Ryan yanked down my underwear. He moaned a hungry “yes” and tried to take all 7.5 inches of my thick cock into his mouth. He gagged terribly on it, then backed off and began licking and sucking on its head. His mouth was really too small for my girth (6 inches in circumference), and so after maybe half a minute I leaned over, putting my hands under his armpits, and pulled him to his feet. I kissed him and he cleaved his small, soft, naked body to mine. I then pushed him back and down onto his bed. Ryan landed on his back and his legs went up, inviting me in.
Without hesitation, I went to my knees on the edge of his bed, he wrapped his legs around my waist, and my cock sank part-way into his hole with absolutely no resistance. Nor, at first, any lube, which was amazing. I pre-cum a lot, and that was our “natural lube,” as Ryan would come to call it; nevertheless, he had a bottle of real lube near his bedside and so we paused to apply some to my blood engorged, very swollen dick and his well-traveled bunghole. I remember looking down and watching as my cock slid in again, and this time almost all the way to my base. It was then that I hit “the wall,” as my cockhead touched the back of Ryan’s rectum and I felt my head begin to spin. I pressed hard for a moment, then backed off and began fucking his hole, slow and in rhythm to the music that was still playing, enjoying the feel of his ass, its heat, its tightness, and the fact that every time I stroked deeply in I would “hit bottom” with still more than two inches of my dick to go. Usually, I can get nearly all of myself into a guy before hitting the back of his rectum, but not this time … and the sense of power and dominance that gave me was almost intoxicating.
Ryan passionately remarked at how completely I was filling him up, stretching wide his insides, and how wonderful it was that I was “hitting bottom.” He then he said something vague about wanting me to fuck his “second hole.” At that time I didn’t really know much about human anatomy, but I didn’t care. This was incredible, and so I nestled the head of my cock against an indention I felt in the back of his rectum and began bouncing back and forth; with each bounce I increased pressure I was applying to the back of his rectum, and after just a few seconds that small indention seemed to open up and the head of my dick popped in! I pulled Ryan’s ass cheeks very far apart and shoved my cock in as deeply as I could, then backed off enough to feel my cockhead pop back out of that inner "hole." Ryan yelped and cried out “do it again!” and so I did. And, with me still on my knees on the edge of his bed, I deeply fucked Ryan with small strokes, pushing my cock into that tiny hole deep up inside him again and again. After a little while I began alternating my strokes, first shallow and then deep … all the way out of his ass and then all the way back in through his anus and rectum and on into his colon … and, in this way, I fucked him. This was the most amazing sex I’d ever had, and it went on for a long time until I couldn’t stop myself and I dumped an enormous wad of cum into his ass, finally pushing in hard and deep to make sure that at least some of my seed would be nicely planted inside his second hole. I then pulled out and collapsed on the bed beside him, panting heavily.
During the twenty or so minutes that followed, while I was recovering enough for us to have another go at it, Ryan and I talked about the “second hole” inside him. He explained that he had looked it up in a human anatomy textbook back when he was still in high school and that it was labeled on diagrams as the “rectosigmoid junction,” a muscle constriction at the back of the rectum that closes it off from the sigmoid colon, which usually branches off to the left behind it. In most guys, it can be found about 6.5 inches deep at the far end of the rectum, but for Ryan (he said he measured it with a dildo) it was only about 5 inches inside him, meaning that most guys can easily “hit bottom” while fucking him, and that several like me had managed to fuck through to his sigmoid colon by an inch or more. I asked him if it hurt, and he said no and that it felt wonderful; being fucked that deeply made him feel utterly full, and when it happened it caused his whole body to tingle every time it was penetrated. He also said that, over the last few years, guys fucking him there must have straighten his sigmoid colon out some so that it didn't have as sharp of a turn, and that made the fucking so much more enjoyable for both him and his partners.
All this talk about anatomy and fucking made us both as very horny – actually, Ryan hadn’t cum yet and had stayed horny the whole time – and now he was getting very playful and slutty with highly suggestive remarks and demands for “action.” And, so, we fucked a couple more times that afternoon. While I really enjoyed punching through to his colon – physically, it feels amazing, and psychologically there’s something especially powerful about being large enough to fuck a guy so deeply that you’re penetrating beyond his ass and into his colon – I pretty much forgot about all that and just focused upon him - his ass, his cute face, and his sexy, slender, twinky little body. I made him cum twice while fucking him the second time, and when I slowed down to stop and let him recover from his first orgasm, he demanded that I keep fucking him. So, I did, and sure enough his little dick grew back up with just a few minutes of me pounding on his prostate. The second time I blew a load in him, I pressed my cockhead through to his colon and let my balls empty deeply into him. We rested and I played with his body – and he played with mine – until I was hard and able to fuck him a third time.
Throughout the entire afternoon Ryan never went to the bathroom to shit out my cum … he kept it inside himself, which made fucking him again and again all the more amazing. At one point I had him on his tummy while I knelt straight up and looked down at my cock, gliding in and out of his hole. As I fucked, I watched with growing excitement as the foam that was being generated by my two loads was churned in his ass and came bubbling out around my cock with each thrust. That sight caused a wave of utter lust to surge within me and led to my nutting a third time in his butt, this time with only half of my cock inside his ass so that I could watch my shaft twitch and jerk with each pulse of cum being deposited there. Ryan, for his part, was in heaven. He spoke dirty and slutty to me, demanding that I fuck him, calling himself my cum bucket, and asking me always for more and more. He loved getting fucked and taking as much cum up his chute as he could get. And he loved it that I could cum a bucket full each and every time I nutted in his ass. He told me, once, that of all the guys whom he'd let breed him, without a doubt I won the award for how much cream he would have in him when we were done.
As I said in the beginning, Ryan was a slut. He loved sex, had many different partners, and didn’t mind too much that I saw other guys, too. He didn’t like Shaun, about whom I’ll share in my next story, but that makes sense because they were nearly carbon-copies of each other. Shaun was also a year younger, and Ryan didn’t like “that little queen nosing in on his bulls.” Since I was one of his favorite bulls, I guess I should be flattered.
I had sex with Ryan throughout my college years and, again, for several years after I returned home from graduate school. I wouldn’t say he was a “boyfriend,” because he really wasn’t the boyfriend type. I was fond of him, however, and when I found out (a decade later) that he had contracted HIV, I hurt terribly for him. He died of AIDS in 2007.
