This young man reminded me a lot of Shaun from my university days. He was VERY small and VERY twinky and VERY desirous for a big, older, hairy man’s cock in his ass. He was a strawberry blond … almost a redhead, but not quite, with the smoothest, softest, palest skin you can imagine … he was almost an albino, except for his hair. He had very little fuzz on his body … a little around his cock and a tiny bit in his armpits. He didn’t shave but once a week, and even then there was hardly any stubble. His muscles were very thin and soft, he had very prominent hip bones and ribs, and his abs were very flat. I loved everything about his body. He had a moderately-small dick, but on his frame it was proportional, and he would cum 2 or 3 times while I fucked him without me even touching it. He never came much but the fact that he could come multiple times in a session really made up for it.
We met at an Ash Wednesday worship service at a friend’s church, where he sang in the choir. He was immediately interested in me, and I in him. The day after that Ash Wednesday service we went out on a date that ended up back at his apartment where we cuddled on the couch in his living room. We made out, I got his clothing off, and he did a provocative lap-danced for me. At one point he asked me to show him my body, and so I did. As I took off my shirt, he began applauding and whistling. The applause continued as I dropped my pants and stepped out of them, only to quiet down when he caught sight of my cock, tenting my square-cut black briefs. I watched as he sat, staring at me, and my cock got harder, longer, and thicker, as it began to pull the top of my underwear away from my waist; I could see that the boy began to slobber and tremble with excitement ever so slightly.
Chad got up and came to me, his hard dick pointed straight out from his body, and I gathered him into my arms as he laid his head against my hairy chest. I’m 6’1” and he was just 5’8”, and as I held onto him I could feel my cock pressing against his stomach, smearing precum all over it. After holding him for a minute and kissing the top of his head, he pushed me down onto the couch and then tried to give me a blow job, which was a disaster … largely because he had trouble getting his mouth open wide enough to take my dick. My cock is 7.5 inches long and very thick at 6.5 inches in circumference; it's circumcised, with a thick mushroom head and prominent veins along the shaft. He licked at it, constantly lapping up the precum, and while I liked that, every time he tried to take it into his mouth he just couldn’t stretch his mouth and lips wide enough to do more than take part my head into his mouth. I eventually made him stop trying, pulled him up onto my lap, held him, kissed him, explained to him that it wasn’t his fault, and then caressed his naked body and masturbated him until he came. He then got back down on the floor, kneeling between my legs, took my cock in his hands, and began to jack me off with both fists, holding them together to create a tunnel. As it was, his hands were so small that he couldn’t wrap them all the way around my cock. He kept telling me how huge my cock was, and that he couldn’t believe how wonderful it looked and felt and how incredible my manly body was. The experience was very hot, watching him stroke me while he talked about how huge I was was very exciting, and I came VERY quickly all over his face and into his mouth. He really liked it and was impressed with how much I came.
The very next day Chad came over to my house for dinner and, after his “hello kiss,” but before he said anything else, he bluntly asked me to fuck him. He was explicit: he wanted it on his back with his legs over my shoulders and me fucking him missionary style. And, yes, the sex was absolutely wonderful: he was very passionate with his kisses as I fucked him, and he would reach up to put his arms around my neck and lift his lean body up to press against mine while I knelt over him and plowed aggressively into his hole. While fucking him I noticed that I was bottoming out against the back of his rectum, with at least an inch or two of my shaft still outside of his hole … a realization that always excites me with my dominance and, this time, quickly led to me cumming hard inside him. As we rested from my first orgasm, I decided to teach him about his “second hole” and about how good it can feel to have his colon fucked. At first, he didn’t believe me, but as I explained the anatomy, showed him pictures in a textbook, and described the sensations that are generated by being fucked there, he admitted that he had felt me hitting his “wall” deep inside him and that other guys who had fucked him had also bottomed out against it. I explained about how the rectum is closed off from the sigmoid colon by a muscular loop which creates a junction, and that penetrating it can feel wonderful for both the bottom and the top. I told him that, in most guys, it’s usually between 6 to 6.5 inches inside the rectum; but I noted that his felt like it was about 5 inches inside, which meant that I could easily breach way past it. He seemed to really be turned on by that thought (his cock was raging hard again with excitement before I was finished explaining all of this), and so we decided to try. I knelt straight up, put a pillow under his hips, tipped his legs back until his feet were on either side of his head, and his ass popped open right in front of me. With my heart racing in excitement, I sank my cock back into him until the head of my dick was pressed firmly against his rectosigmoid junction. Sure enough, I could see about two inches of my shaft remaining outside his sphincter, and the sight of that was amazing: I was filling up this twink’s entire rectum and there was still more of me to go! Wow! Without a word, I applied steady pressure and waited; often, guys loosen up quickly, but Chad’s wall remained firm. So, I told him to try bearing down with his sphincter around my cock, and when he did that the pucker in the back of his rectum relaxed and POP … I felt the head of my cock and about an inch of my shaft penetrate further up into Chad. He gasped out loud, sucked in a deep breath, and then cut loose with an orgasm that shot way into the air and splattered his tummy and chest with a thin glob of cum.
I waited until his orgasm had subsided, and then I pushed in deeper … all the way in until my cock was entirely buried inside him. There, I held still for a few moments, relishing the feeling and realizing that his inner hole was spasming around my cock about an inch and a half behind the flared ridge of my cock’s head. I could also feel the tissues on the inside of his sigmoid colon beginning to relax and straighten out as my cock adjusted his insides. After allowing us both to become accustomed to the new sensations, I began fucking him, making sure to keep my strokes down to just a couple of inches … I was pulling my cockhead out of his second hole, then punching right back through it with repeated, steady, firm thrusts. The sensation reminded me of Ryan’s ass from many years ago, and I leaned hard into it and really enjoyed the power, position, and knowledge of what I was doing to this cute boy as I built toward my second, soul-stirring orgasm. I guess the pulsing of my cock as I came deep in his colon sent Chad over the top, because as I blew he also came, this time splashing my stomach with his load.
The next time we got together – it was just a day or two later – Chad told me that he wanted to try riding my cock, and after a little bit of adjustment (putting a pillow on either side of my waist so that his short legs could handle my body, he really took to that position with gusto. He would rock up and down, long and slow, and every 10 or so minutes he would stop and settle down hard on my lap as the head of my cock would press through to his colon. In that moment, his body would convulse, he would cry out, his ass would clamp down on my cock as his own dick would jerk and a bit of cum would spurt out onto my stomach. He enjoyed those anal orgasms so much … and, for me, it was better than any applause. I would fuck him as long as I could, relaxed and enjoying the show, the feel of his skin, and the expressions of lust on his face. Those rides went on for a very long time – I timed one from start to finish as being slightly longer than an hour, during which he would come at least 4 times! – but, eventually, I discovered that I couldn’t hold back much longer than that and when he had his next anal orgasm, the convulsion of his body and the spasming of his rectum around my cock sent me over the top and I would blow my load way up inside him. He told me how wonderful that felt, to be flooded by so much cum, and then he would settle down and doze off, resting his head on my chest … sometimes not even bothering to pull himself up off my cock. He would sleep for hours like that, using me as a furry mattress. It was really sweet, and I loved those fuck sessions and their aftermaths.
For several months, things went very well. I was becoming more and more fond of Chad, and I thought he was feeling the same about me, but then he began dropping little hints that perhaps I wasn’t old enough for him. Yes, Chad liked much older men; I knew that, and I had been in hopes that the 12-year difference between us would be enough … but, apparently, it wasn’t. Without any other warning, about a month or so after my 32nd birthday, and without even a polite “thank you,” Chad left me for a man 20 years older than me! Realizing I had been dumped for not being old enough was a weird feeling; to be honest, I was very hurt, but at the same time I also knew that I had several other options when it came to sexual partners, and I was hoping to find someone else via an ad I had placed on AOL, so I didn’t let getting unceremoniously dumped bother me too much. Nevertheless, I’m not going to lie: I loved fucking Chad. That I could easily pierce through to his colon was a huge bonus, and one that I really enjoyed and missed in the subsequent years.
