My decision to act on my sexual attraction to men came in my late 40s, and in erratic fashion. Oh, I had been curious in my teens, avidly reading paperbacks about gay sex, and masturbating to stories filled with sucking cocks and anal sex. That continued on and off over the years, but the choice to actually do something about it did not come about until the internet came on the scene, and I discovered websites with men wanting to have sex with other men. I decided I wanted to experience the things I had read and fantasized about so many times.
This led to an interesting, but mostly unsatisfying series of encounters over several years. I met men, kissed and made out with them, stroked their cocks and sucked them off, and experienced anal sex both as a top and as a bottom. But the experience I was looking for eluded me. I still looked at a lot of gay porn online, and certain things aroused me more than others, such as deep kissing, foreplay, and 69. But what really got me hard was watching two men go at it in full missionary position, with the legs bottom wrapped around the hips of his partner, and the top with his arms around the neck and shoulders of the bottom, stroking into him in a slow and deep rhythm. It looked so hot, and I wanted to try it so bad, but it never worked out. Then I got lucky, twice.
When Craigslist still had a personals section, I browsed frequently, and one day came across an ad that looked promising. His name was Don, a younger guy in his 30s, not far away, and he answered in a few minutes. We exchanged emails, then pictures. One of his was of a very hard cock, with a large head, 8 inches he said. After more chat, he agreed to come over. I took a quick shower, and put on a t-shirt and a pair of loose fitting shorts. Then, right on time, there was a knock at the door. I let him in, and we went to the bedroom.
I looked him over as we undressed, and liked what I was seeing. He was about 3 inches taller than I, slender, with a nice amount of hair on his chest, trailing down to a tangled bush around his cock. His cock was longer than it looked in the picture, and was already sticking straight out. Mine was hard too, and as I stood up, he was staring at it. I stepped over to him, and we embraced, and began to kiss. He was a good kisser, too, and our tongues swirled around while our cocks rubbed against each other. Oh, it was hot! His cock was now standing straight up, the head swelled and leaking precum. We finally broke off the kiss and went to the bed.
Laying down, we started another hot kiss with lots of tongue, and I slid my hand across his chest, fingering his hard nipples , then down his belly until I reached his cock. It was hard, with a big ridge on the underside, and of course the big flaring head. I started stroking it, slow, and sliding my thumb across the head when I reached the top.
He then stopped kissing me, looked at me, and simply said, 69? I just nodded, and released my hold on his cock. Leaving me on my back, Don turned around, and now the big sticky head of his cock was over my face. Lying down on me, he took my straining cock in his mouth, and began a nice slow up and down with his mouth, and swirling his tongue around the head at the same time. I reached up, and pulled his to my open mouth, and took in the head and a couple of inches. It seemed to fill my mouth, but as he began to pump his hips, I tried to relax and take as much as I could. After a few minutes, I was taking almost half of him, while I could feel his lips against the base of my smaller cock. I had never done a 69 in this position, and was ready to let it go until one or both of us blew a load. We had not discussed it, but I was hoping he would want to fuck me. All that was forgotten when he was sucking my cock all the way into his hot and wet mouth, and rolling his tongue around it.
Then, Don stopped and turned so he could look at me, and asked if I wanted to do anything else? Now was my chance, and I blurted Do you want to fuck me? Sure he said, and rolled off of me. Sitting up, I pulled open the nightstand drawer, and grabbed a tube of lube. Shooting some on my fingers, I reached around and smeared it around my asshole, and pushed some inside. While I was preparing for the invasion to come, he was coating his cock with lube. How do you want it, he asked. On my back, i managed to get out. Kneeling, he maneuvered between my legs, and grabbing my left leg, lifted it up onto his shoulder. Holding his oozing cock with the other hand, he guided it to my hole, and began to push.
As my ass ring stretched, the familiar burning sensation flared, and I asked him to pull back and try again. This time, I stretched around the bulbous head, and it popped in. Feeling full and spread like never before, I help up my arms to him, but he leaned down and supported himself on his hands. I put hands on his back, and lifted my legs, placing my heels on his ass. Now in a good position, he began to pump in and out, with short strokes. Immediately, I could feel a new sensation, the head of his cock rubbing against my prostate on every stroke. Already aroused to high state, this new stimulation was quickly pushing me to the edge. I could feel the tingling building behind my cock. Looking down my chest, I could watch his cock stroke into me, and his belly rubbing against my cock. Leaning back and looking up at Don, I could see his eyes were closed, and sweat was beading up on his forehead. All the discomfort from taking his big cock was gone, and I only felt the pleasure of him filling me, and stimulating my insides. A few more strokes, and I came, the first shot of cum flying out and landing well up on my belly, followed by several more. Looking down again, I could see a sizeable puddle of cum on my stomach.
