Journey of a Middle-Aged Man

Before my two awesome bottom encounters with Don and Pete, I had met and had sex with other men, which were fun, but didn't meet my expectations in one way or another. Early on, I was just groping around, not sure of what I wanted or how I wanted it. But, looking back, each one set the stage in some way for what was to come later in my life, when I lay on my back, with my arms and legs wrapped around my lover, while he pumped a very large cock into me.

Before I discovered Craigslist, Adam, and other effective ways of meeting men, there was Adult Friend Finder. At the time, it wasn't expensive, so out came the credit card, and I signed up for a month. After a few days, I discovered a profile for a college student in a neighboring town, who could host. Taking the plunge, I sent off a message, and was rewarded a few hours later with a reply. As we chatted, I learned he was 28, Hispanic, lived alone, and was very eager to meet. The fact I was 20 years older made no difference to him, could I come right now? I agreed to drive to his place after work.

Arriving at the address, it was a basement apartment under a dwelling converted into an office. Knocking at the door, it opened, and I was greeted by a very handsome young man, a head taller than I, with nice dark skin and big smile. He sighed, and explained that a friend was coming over unexpectedly, and he would have to break our meeting date. We chatted a minute longer, then I started to leave, and he touched my arm, and asked if he could kiss me. I nodded, stepped into his embrace, and our lips met. Immediately, his tongue pushed into my mouth, and started probing against mine. My cock strained against my jeans in a full, hard erection, and I kissed him back, turned on like I had never been before. It was wrong, against all my upbringing, and I loved it!

As we stood, feverishly making out, I dropped my left hand to his waist band, pushed my hand down the front of his sweat pants, and found his cock. It was just as hard as mine, and I took it in hand, and stroked it. He broke the kiss, and whispered in a hoarse voice that I had better leave before his friend caught us. So, reluctantly, I left and started for home.

A few miles into the drive, my cell phone buzzed, and looking at the number, saw it was Brandon. Thumbing the call button, I said hello, and was greeted by him begging me to turn around. He had managed to put off his friend until another time, and was wanting me to come back, so we could finish what we had started. I was still hard from my first man-kiss, so it took little to get me to turn around.

Back at his tiny apartment, I found him naked on his bed, copper skin with dark brown nipples, and a small but hard cock, so off came my clothes, and I crawled into bed next to him. We then started another hot makeout session, with our hands roaming freely, cupping each others ass, and fondling the others cock. I was so close to unleashing a big load of cum, and wanted his cock in my mouth, but he broke the kiss, and asked if I would fuck him. At that point, I would have agreed to anything, so I said yes, and got out of bed. Brandon produced a condom and lube, handed the condom to me, and proceeded to lube up his ass. Then he turned around, and put his head and shoulders on the bed, with his ass in the air, the small brown pucker shiny and slick with lube. Since he was taller than I, I had to spread his legs wider apart, and get up on my toes to get my cock lined up with his hole. Pushing the head against the brown ring, I felt resistance, and worried that I wasn't going to be able to get in. Then, without warning, it popped through, and I was in. Brandon groaned, probably in pain, but I was caught up in lust, and wasn't hearing. I started pumping my cock in rapid strokes, the condom cutting off the feeling, so I went faster yet.

Even though I have a short cock, it's fairly thick, so I had to be causing him pain, but all my concentration was on my cock. Gradually I could feel the sensation building behind my cock, the tingle of a building orgasm. I was sweating like crazy, as was he, as I slapped against his ass in a rapid cadence. Then I was there, and I pulled his hips against me while cum spurted out of my cock into the condom. We stood there for a minute, locked together like a pair of dogs, then I slipped out of him and collapsed on the bed. I watched as he wiped the lube from his ass, then he came and stood before me, his cock still hard and throbbing. Now I could finally taste a cock in my mouth. Sucking him in greedily, I grabbed his ass cheeks and started bobbing my head up and down, taking his full length into my hungry mouth. I wanted to taste his cum, and swallow his load, but he pulled out and started wanking his cock hard and fast. It was only a few seconds, then the first rope of cum shot out onto my chest, followed by 3 more. Then it was his turn to flop onto the bed, and mine to clean up. As I dressed, we talked, and I asked if he would return the favor, as I was very curious to try it as a bottom. But, he replied that he preferred to bottom, and doubted if he could stay hard if he tried to penetrate me.

I thought about calling him again, but decided our needs weren't compatible. I wanted to suck a hard cock to the end, and swallow the semen, and I wanted to bottom. Some time passed, and I was contacted by a guy who was 48, same as I, who offered to host if I was interested. His name was Jose, another Hispanic, but with lighter skin, and a very furry bush around his cock. The picture he sent was of a fat cock with a pointed head, and a gaping piss slit. I was intrigued, and agreed to meet.

Our meeting was fun, with a lot of kissing, rubbing our cocks together, and fingering each others assholes. He wanted to bottom, and I was game, but the condom prevented me from getting any feeling, and I lost my erection. I wished I had asked him to fuck me. Looking back, I believe he would have, and it would have been fun, but at the time, I just wanted to be done and leave. We ended up jacking each other off. Afterwards, we chatted online from time to time, but never met again.

My next partner was Davis, a short and trim man 4 years older than I, with a neat goatee and short graying hair. He was traveling through my community, and we had a mid-day meeting. His profile said he was a top, but he informed me he wouldn't have time for that, but would enjoy getting naked, and getting off with me. We undressed in my bedroom, then stood and kissed next to the bed. Davis was an excellent kisser, with a nice body, and very small cock that was a bit shorter than mine, and not as thick, with a small round head. I was very aroused, and my cock stood straight up. His did too, and we ground them against each other as we held each other, our tongues twisting and probing. We stopped long enough to get on the bed, and began what was my first 69. Licking and sucking his hard cock, I could feel him doing the same to mine, and my orgasm was coming on fast. I pulled off his cock long enough to gasp that I was cumming, then he pulled away and jacked me while I shot several strings of cum onto the sheets. Davis asked me to suck his nipples while he jacked off, and he finished himself that way. A few weeks later, I received a message that was retiring, and moving to a warmer state. Of course, that meant our first meeting was our last.

That was the beginning of a frustrating couple of years. I had given up on adult friend finder, and was trying other sites, but with no success. I had many conversations, but it seemed like there was always something not right. They were too far away, or they were too tall or too heavy. Many only wanted to bottom, others only wanted to have oral sex. Some wanted to bareback. I was curious about that, but knew the risks involved. I found that there were men who simply didn't care about catching an STD, and I wanted no part of that. I'd get frustrated, and give up for a few months, then would come back and start looking again. All the while, I'd browse porn sites, and stroke myself while watching men engage in hot sex, with long cocks pistoning into eager bottoms, and others with cum spraying onto a guys face. The need was there, but I had no outlet for my frustration.

One day while browsing Adam, I found a profile located in a city not too far away. He was a bit younger than I, a couple of inches taller, slender, and it had a picture of a nice semi-hard 6.5 inch cock. The other pictures looked good too, so I fired off a greeting, and a request to chat if interested. A couple of days later, his response was in the inbox. His name was Kent, he was married, and lived in the same town as I. His free time was very limited, but would be home alone on the weekend, would I like to come over? After more chat, I agreed, and we set a time. The weekend arrived, and I drove to his place, freshly showered, and nervous as I always am for a first meeting. When the door opened, and I saw a nice looking guy, with short cropped silver hair and goatee, a bare chest with a thin cover of gray hair, and a nice bulge under his gym shorts. He let me in, and led me to a bedroom in the back of the house, where we undressed. I was fully erect by now, and saw that his cock was standing out, but not hard as it would get. We embraced, and he nuzzled the side of my neck while grinding his cock against me. I turned my face to kiss him, but he kept his face buried in my neck, so I kissed and licked at his ear. This brought a moan from my new partner, and he let go, and dropped to his knees.

Taking my cock in his mouth, he started to suck on it, and working on it with his tongue at the same time. This brought me to the edge quickly, and I told him I was going to cum, thinking he would pull away. Instead, he picked up the pace, and I shot my load into his waiting mouth, and he swallowed it without hesitation. I pulled him to his feet, and tried to kiss him again, but he turned his head again, so I just hugged him, then told him to lie down on the bed. Getting on the bed next to him, I took the head of his cock in my mouth, and began working up and down on it, while stroking the shaft with my hand. Like me, he didn't last long, and began spurting cum into my mouth, my first time for that. I had tasted my own cum many times, and this was no different, the salty cream hitting my tongue and sliding back into my throat. It was a big load, with at least 5 big spurts, but I took it all, eagerly. I thought he was done, and pulled off his cock, only to have one last shot fly out and land on my cheek.

Kent and I met several times after that first encounter, but it never went beyond sucking each other off. He would never let me kiss him, and the one time I asked him to fuck me, he lost his erection. So while being with him was fun at first, it wore out after a while. I wanted more than he was willing or able to do for me.

It was this point I discovered a profile for a younger guy named Carl. He was in his late 30s, my height, very slender with a nice amount of body hair, and what looked like a real nice 7.5 inch cock with a slightly flaring head. He lived about 12 miles away, alone in an apartment, and was willing to host. We discussed in some detail what our expectations were. He said he liked making out as foreplay, then wanted to get to business. He asked if I was interested in anal sex, and I replied that I was, preferably as a bottom, but had topped one time. His next question was if I had ever experienced bareback sex, and I answered no, I had never had taken a cock with or without a condom. He then said he preferred it, but was careful to only do it with guys like me, who were anal virgins, or with guys who had been tested and could prove it. He had not been with a guy for several months, and had been tested himself recently with negative results, and asked if I would consider it. Even if he had to wear a condom, he wanted to fuck me, he said, and would be slow and gentle. I said I would definitely think about it, and we chatted a bit more, and decided to meet later that day. Driving to his apartment, I was excited at the possibility of losing my anal cherry, especially to a good looking man like Carl.

His apartment was small, and he had no bed, only a mattress on the floor. He shut the door, then walked over to me, put his arms around me, and kissed me with passion. Already aroused, I kissed him back, and our tongues began the dance of two lovers who are into each other. He was wearing a pair of plaid sweat pants, and I wanted to see his cock, so I reluctantly broke the kiss, and loosened the drawstring. Sliding them down, his cock popped out, the head glistening with precum. He chuckled and said we should take it to the bedroom. He stretched out on the mattress while I undressed, and said my pictures did not do me justice, that I was very good looking, and had a great body. I replied he was hot as hell, and lay down next to him, and we kissed again while fondling each others cocks. It was very exciting, I was so turned on I was almost shivering. He was a great kisser, his tongue rolling around mine in lazy circles while his hand slid up and down on my cock.

Just when I was about to go over the edge, he stopped, turned so his head was at my cock, and took it gently in his mouth. His cock was likewise inches from my face, all I had to do was lean forward and suck it in. We started a slow rhythm, sucking and licking, building the sensations all over again. Then, he rolled onto his back, pulling me over and on top of him. My cock was immediately back in his mouth, and I began pumping my hips up and down, fucking his warm wet mouth, and sucking his cock in and out of mine. Again, I was in danger of cumming too soon. Just in time, Carl gently pushed me to the side, and as I lay on my back, he got up, and grabbed a plastic bottle. Kneeling next to me, he squeezed a warm clear liquid on my cock, and spread it around with his hand. My eyes were closed, enjoying the pleasant feel of his hand, when I felt him straddle me. Opening my eyes, Carl was above me, with a hand behind him, reaching for my cock. Once he had it, he lowered himself onto the head, and it felt my cock pressing against his asshole.

Then, it pushed past the ring, and I was in him, bare. I was in a bit of shock, it had happened so fast, but I couldn't get any words out. My whole focus was on my cock, gripped in the warm embrace of Carl's ass. He started a languid up and down motion, riding me, with his cock hard and pointing straight up. Then he picked up the pace, and his cock began waving back and forth. I was already aroused as never before, and the orgasm built rapidly in me, then it was there. I arched my hips, and drove into him as deep as possible, flooding his insides with hot cum. Carl had leaned back, his head thrown back and his eyes closed, as he took my load. It was unlike any orgasm I had experienced to that point.

Carl rolled over and lay beside me while I caught my breath, and my heart stopped hammering. He rolled over and kissed me, and asked if I wanted him to do me. Again, I was too caught up to think, and just nodded. He smiled, and told me to roll onto my side, that it would go easier that way. I did as he said, and soon felt his fingers smearing lube on and around my asshole. It felt good, and I relaxed , even when his middle finger began probing around the opening, and then slid in a short ways. He took his time, gently working the lube into the ass ring and the channel beyond. I was really enjoying it, I'd inserted my own fingers there many times, but it was so much better having another guy do it.

Then Carl pushed two fingers in me, and began a slow fucking motion, gradually opening me up. He applied another layer of lube, then lay down behind me and snuggle up against my back, one arm around me, and the other lifting my leg, exposing my now slick hole even more. He took his cock, and guided the head against my asshole, and began to push. Even with the preparation, I was caught off guard by the sharp burn as the head stretched the ring of muscle, and sucked in my breath. Carl stopped, and let me get used to the intrusion, then resumed working the head in and out very slowly. The pain subsided, and I was able to relax again. Carl pushed in deeper, and this time I felt a sharp stab deeper inside, as his cock hit bottom and stretched my channel.

Again, he backed off, and allowed me to adjust. The whole time, he held me close, and I could feel his lips on the back of my neck. I reached behind me, put my hand on his ass, and pulled him against me, pushing his cock in me to the base. It was still uncomfortable, but I was getting fucked for the first time, and wasn't going to stop. Carl started pumping me with shallow strokes, and I finally began to feel a pleasant sensation as his cock stimulated new places inside me. I was able to close my eyes and enjoy the ride, Carl tight against my back and breathing heavily in my ear. My cock had revived, and was very hard, jerking every time Carl pushed his into me. After a few minutes, Carl grunted that he was going to cum, and pushed his cock in as deep as he could, and held me tight as he began emptying his load into me. It was an amazing experience.

We agreed to stay in contact, but a week later, he sent me a message that he had been evicted from his apartment, and had to move. It was several weeks before we spoke again, and he had taken a different job, was living with friends. As it turned out, we never hooked up again.

I wanted to have that feeling again, of a cock thrusting into me, and all the pleasure that came with it, but I wasn't able to find a potential partner that I was comfortable with. There were many online conversations, and I even met Kent again for a blowjob, but could not find a safe top. I suspect this is a common situation, especially for older men in small towns. Finally, when out of town on business, I came across a profile of an Asian man, in his mid 30s, who lived a few blocks from the motel, and could host. He was adamant about safe sex, and was a top, so after asking more questions, I agreed to come to his place. I made some excuses to my travel companions, and drove to home. It was nice, in a clean middle class neighborhood, so I pulled into the drive. The encounter started off good, with him taking a lot of time with foreplay, and loosening my asshole with small toys. With me on my stomach, he put on a condom, lay down on me, and I felt him place his cock against my ass. It slipped in easily, and I felt this was going to be fun, when without any buildup, he began a fast and almost violent fucking. All the pleasure blew away as he jackhammered me. I was lucky he didn't have a big cock, otherwise it would have hurt worse than it did. I lay there and let him have me, and he finally came, and pulled out. That was my last time with a man, before my sessions with Don and Pete, as described in the previous story.