Journey of a Middle-Aged Man

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.

Don kept up his pace, and the pleasure continued. I was wanting him to cum too, adding his load to spreading mess on my belly, or cumming inside me if he wanted to. But, unexpectedly, he stopped, and asked if I had enough. When I asked if he was going to cum too, he replied that it took him a long time, if he was able at all, and he did not think he was going to cum this time. So he pulled out and stood up. Laying there, I watched him wipe the lube from his cock, then grabbed a towel and wiped up the sticky semen from myself. He said very little while he dressed, or as we walked to the door. I thanked him for a great time, and said I hoped we could meet again, but got no response, just a goodbye and have a good one.

In the days that followed, I replayed the encounter over in my mind, stroking my cock, remembering how it felt, and wanting to be with him again. But, I received no answer my emails, and there it ended. Some time passed, and I met up with other guys, but that same feeling was never there. One guy I met, Pete, was around my age, slender, with a shaved body. We had met twice, and it was fun, but it never went beyond mutual jacking and blowjobs. He did have a big cock, but for some reason he seemed hesitant about anal sex, so after those two times I moved on. Eventually, I gave up trying to meet other men, and satisfied myself watching porn and jacking off.

A couple of years passed, and the old urges started to come back, a little at a time. I started visiting the websites again, and posted an ad on Craigslist. Among the responses was one that said he was a few minutes away, he was a top, and he would take it as slow as I wanted. His stats were what I was looking for, middle-aged, slender, and a bit taller than myself, so I answered back. We had a good online conversation, our wants and needs seemed compatible, so I agreed to travel to his place. The address seemed familiar for some reason, but I forgot about that as I got ready.

From the picture he sent of his cock, it appeared he had a nice cock, but pictures can be deceiving of course. We had discussed our preferences, him a top, me a bottom, so I was anticipating having it inside me. I took a shower, made sure I was clean inside and out, grabbed lube (just in case), and made my way to his place. As I drove up to the address, I realized I had been here before. Pete, one of my previous partners, lived here. Hmm, do I want to do this? My memory was that he was a nice guy, and liked making out as much as I did. And he did say he was interested in topping. So, I pulled in the driveway, thinking what the hell, I had nothing better going for me. As it turned out, I was glad I went in.

Pete was still the friendly and chatty guy that I remembered, saying he wondered when we were online if it was me, and how glad he was to see me again. I felt at ease as we went to his bedroom and undressed. Watching his clothes come off, I saw he was no longer shaved, and still had a nice trim body. We lay down on our sides, facing each other, and leaned in and kissed. Pete was vocal, as he had been before, moaning while we kissed, and giving a drawn out oooooh when I took hold of his semi hard cock. As soon as I touched it, it swelled and stood erect, nicely up curved, and much larger than I remembered. As I said, I had recalled he had a nice one, but this was at least 9 inches long, and thick, and the same thickness from the base to just below the pink bullet-shaped head. For some reason it had not made an impression on me before, but looking at the thick pole in my hand, I saw I was finally going to experience a truly big cock.

Our tongues slid out, swirled around, and probed. Then Pete moved down, and started sucking on my nipple, and at the same time reached under me between my legs, and started rubbing my hole with his middle finger. It was all done in a soft manner, without aggression, and it was wonderful. Popping the cap on the lube with my free hand, I released his cock, squeezed some lube into my hand, and moving his hand aside, applied the lube to my hole. He replaced his finger when I was done, and gently slid it inside me. With a generous amount of lube still on my hand, I took hold of his cock again and smeared lube on it, up and down, with a circular motion. He groaned, and his cock seemed to swell even more. Can I fuck you, he whispered in a hoarse voice. Yes, take me on my back I answered.

Sitting up on his knees, Pete smeared even more lube on his cock, then moved between my legs. I spread my legs, and raised them high, giving him free access to my ass. Leaning forward against my legs, I watched as he took his swollen cock and pushed the head against the rim, and started to ease in. It was painful, so I had him stop, and I made an effort to relax. Then he tried again, and it was better, he pushed, and he popped past the ring and was in me. I had thought Don had stretched me, but nothing like this, and he was only in a couple of inches! Pete started a slow and gentle motion, each time pushing in a little deeper. It was uncomfortable, it had been a long time since I had a cock inside me, and every stroke felt like it was hitting bottom. But, he was gentle, and gave it to me a little at a time, and the discomfort passed, and I began to feel the pleasant buzz inside me. Then, he was in, all the way, his pubic bush against my balls, and he groaned again, and leaned forward. I reached up to him, and spreading my legs wider, pulled him to me. Oh yeah, I like this he moaned, and lay full on me, with his arms around my neck. I wrapped my arms around him, and crossed my ankles behind his lower back, then kissed him, hard. Our lips together, and tongues dancing, Pete started a gentle fucking, first in and out a couple of inches each stroke. Then, gradually pumping almost the full length of him in and out, and all I felt was this huge cock filling me up and putting constant pressure on my prostate. My cock began leaking a steady stream as the pleasure built.

He broke the kiss, and moved to my neck, groaning in my ear You are so fucking tight, I love your ass. I was lost in the pleasure of the moment, it was everything I had hoped it would be. A good looking man with a nice body, and a huge cock, was laying on me, and giving me the fucking I had only dreamed of. I pulled him tighter against me, and moaned in his ear you fuck me so good. Pete was going faster now, and I could feel an orgasm building. He groaned he was getting close. Cum inside me I answered, and felt him give it to me even faster. Then, he made a growling sound, and drove all the way in me to the base, and held it there. I felt him stiffen in my arms, then he growled again, and exhaled. The stories you read of feeling the ejaculation are not true, but I knew he had cum inside me. I lay under him, still entwined, with his cock still buried to the base, and realized I had finally experienced what I had always wanted. But Pete was not finished with me. He rolled off me, then bent down and took my still-hard cock in his mouth, sucking it in and rolling his tongue around the head. In less than a minute, I arched my back and blew into his waiting mouth. One more long kiss, and we were done.

No second meeting yet, but plan to do so soon. I want to let him take me from behind, or perhaps straddle him, and take him up inside me from that angle. There are a lot of new fantasies that I want to pursue!