I Like to Bottom

This is a fiction story about a mature man's experiences with gay sex.

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Several months after I became a widower, I took stock of my situation. I was living alone in a small rural community, 30 minutes or so from one of the large metroplexes on the river. The last few years had been filled with doctor appointments, hospital stays, outpatient treatments, etc, so our social life had gone by the wayside, and our friends had moved on. We had no children, and no relatives nearby. So for the first time in 30 plus years, I was truly on my own, and answered to no one but myself. In the area of sex, I had a lot of pent-up demand to get out of my system, and with the help of some dating websites, I embarked on a string of dates which in most cases led to sex. After several of these one night stands, I realized I was leaving myself wide open to catching an STD, and scared myself silly. A full spectrum STD test came back clear, and with great relief, I vowed to be much, much more careful going forward.

I also realized that what I had been doing, while fun, left me feeling empty. Even though it was with some truly entertaining women, it was still the same kind of sex I had done all my life, just variations on the theme. So, I started browsing a lot of porn sites, checking out different things. As we all know, there are a lot of 'things' out there on the internet, and most of them weren't my cup of tea. Up until now, I had never given a thought to any aspect of gay sex, so it was with some hesitation that I clicked on the 'Gay' category button, to see what it was all about. I watched several clips of men having sex with each other in various ways, and surprised myself by becoming aroused. I ended up taking off my clothes, and jacking off while watching a hairy bearded man get fucked in his ass by a very skinny young man with a very large cock.

In the days and nights that followed, I watched more and more gay sex clips, and became increasingly curious about trying it for real. But, I had a lot of inhibitions to overcome, so it was several weeks before I went to one of the websites advertised, created an account, and logged on to see who was near me. No surprise, most were in the city and suburbs, but there were a few closer in. I had given this some thought, and had already decided to confine my inquiries to men closer to my age, and who admitted to being married. I was very nervous about contracting an STD, so I felt this pool of men offered a better chance of being safe. I also intended to ask a lot of questions before agreeing to meet anyone.

I was naïve, but I did get a few responses, and ended up meeting a few. At first, I was extremely nervous, and would only do oral sex with some foreplay. After the first couple of times, I found it very exciting, both for the novelty, and for the 'taboo' aspect. At this point, I should mention that I am 58 years young, 5'7" tall with a trim build. Not much body hair, with the exception of a tangled mass of pubes framing my 6"cock. My partners all commented on how good looking I was. I had never given it much thought before, so hearing it from others did a lot for my confidence. In any event, I was having fun with oral sex, but I was also curious about another form of man-to-man sex.

It was inevitable I'd eventually try anal sex. I watched a lot of it online, and found it fascinating. Unfortunately, the first couple of times were so painful I almost got up and ran away. Afterward I sulked, vowing that was never going to happen again. Then the memory of the pain would subside, and I'd get the urge to try again. I sought out partners will smaller cocks, and eventually my asshole stretched out enough that a cock entering me was no longer a terrible experience. It was then I began to experience the pleasure anal sex could give me. I tried different positions, and also topped a few guys. Topping was fun, but the real thrill came from being penetrated. I also started to seek out partners with bigger cocks. I'd have some pain at the very beginning, but it would subside right away. And through all of this, I was careful to accept offers from guys I knew, or who had been tested, and I was never fucked by a bare cock.

Around this time, I had a new experience. I'd met a nice guy online, married, who was just beginning to get into gay sex, and we agreed to meet. He had a nice 8" cock, topped by a big head with a pronounced rim, and he would be the biggest guy I had ever taken. I was kneeling, and he entered me nice and easy, almost no pain at all. I was able to take his full length, and he began a nice slow fucking. I was having the most incredible sensations, especially when he pushed into me, and I realized the big knob head of his cock was rubbing against my prostate on every stroke. Wow, it felt great! Soon it felt like an orgasm was building inside me, and then I felt cum dribbling out the end of my cock, making a puddle between my knees. It wasn't a full-blown gush like a normal orgasm, just a thin steady stream. Later, he took me again, this time on my back with me legs on his shoulders, and it was even more intense.

After that, I was no longer afraid of big cocks, and that brings me to the present. I had recently put up my profile on a gay meeting site, and had received several inquiries. I was sorting through them, and one caught my eye. The guy's name was Chester, nickname Chet, and he lived alone just outside the city. He was my age and height, slender, and was a good-looking black man from his pictures. He had unlocked his photos, and as I scrolled through, came on a cock pic. It was soft, but obviously very long and thick, with a conical head. I just stared, and felt my own cock stirring, wondering what it looked like hard. I clicked on his profile and read through it. It said 9.5". Hmm, that was a big one all right. Reading on, it said he owned a salon in the city, was conservative in dress and manner, was a top (big surprise there), and under safe sex he had entered 'sometimes'. It also said he was HIV negative.

The entry about safe sex was a concern, but he was interesting, and I decided to follow up with a response. I checked back later, and saw I had a message from him, and that he was online. He was very up front and forthcoming in his answers to my questions. He stated that he would get tested every 6 months, and his results had always been negative. As far as safe sex, he said he always used a condom, unless he was in a relationship, and trusted his partner. He also included another picture, and it was very hot. He was standing sideways in front of a full-length mirror, and this time his cock was at attention, hard and curving up to point at his chin. Looking at the picture, I rubbed my cock through my jeans and clenched my asshole, wondering if I could handle such a massive thing.

I sent a message back, thanking him for addressing my concerns, and telling him I was definitely interested. I told him I had been recently tested also, and that he should know that even though I had been fucked several times, I had never taken a cock as large as his. His response was "Lol, about time you tried one then". He went on to say that he was used to breaking guys in, and that he would be gentle with me and use lots of lube. He also said he thought I was a very good looking man, based on my pictures, and would like to meet me. He was free in a couple of hours, was I interested? I decided to go for it, and told him I wanted to meet him too. He gave me his address, and a description of his house. I used the time to get myself clean, inside and out, and had a drink to calm myself. The time to leave came around very fast, and I was on my way.

His place was in an older subdivision, but the homes including his were neat and well kept. I rang the bell, and the door opened, and there he was, even better looking than his pictures. Chet gave me a big smile, and waved me in. The house was small, but very clean. I took a seat on the couch, he brought in a couple of cans of beer, and we chatted for a few minutes. I had been nervous about going to stranger's place, no matter how nice he seemed online, but everything was quite normal, and I was able to relax. After Chet finished his beer, he set the can down, and turned to me, putting his hand on my leg.

"What do you think?" he asked. "Do you want to stay for a while, have some fun?"

"Oh yeah." I replied. "You seem like a pretty cool guy."

"I like to think I am." he laughed, and he leaned forward to kiss me. I sat up, and met him halfway. Our tongues immediately met, and began to swirl and probe. As we made out, I could feel his hand sliding up my leg. When it reached my cock, he rubbed it through my jeans, making it jump to attention. I moaned, and moved my hand to feel for his cock, feeling the big bulge under his sweat pants. My, it felt big, long and thick, and already very hard. We sat there for a few minutes, making out, and fondling each other, then Chet pulled away, stood up, and removed his shirt, revealing a lean chest with black nipples and a patch of wiry gray hairs. Then he slid his pants down and stepped out of them, and his erect cock was there in front of me. It was dark like the rest of him, with a pronounced ridge on the underside, with a pinkish head, and gray pubes like the chest hair. He moved closer to me, and I took the black shaft in hand, tilting it towards my waiting mouth, and took in the head. He moaned, and put a hand on my head. I licked at the head in my mouth, and ran my hand up and down the length of him, bringing more moans from him in response.

With my free hand, I unbuttoned my jeans, and pushed them down far enough to free my cock. It sprang free, and I grabbed myself and started to stroke it in time with the hand holding Chet. He liked what I was doing, and began fucking my mouth with short strokes. I could feel the head swelling inside my mouth, and all fear aside, I wanted it inside me. Giving it a last sucking kiss, I pulled it out, and looked up at my new lover.

"Do you want to fuck me?" I asked.

"Mmm, yes. Is that what you want?"

"Yes, I do. I want to feel it, deep in my ass."

"Wait here." Chet walked into an adjoining room, and I admired his slender body with the firm round ass cheeks so typical of black men. The view was even more exciting when he returned, his cock swaying from side to side as he walked. He had a condom, and a bottle of lube. "Turn around." He ordered, and I did so, kneeling on the couch with my elbows on the back cushion. I felt his hand on the crack of my ass, then his fingers smearing lube up and down my crack and around the hole. Then a lubed finger pushed inside me, and my cock gave a jerk and I closed my eyes to savor the pleasure. Chet did as he said, putting a liberal amount of lube on and in me. The next thing I felt was his cock head against my hole, rubbing up, down, and around as he spread lube on his cock shaft. It came back to my hole, and began to press inward. I relaxed, and pushed out a bit, spreading my hole, and Chet's bulblous head slipped in. I felt stretched, but no pain, and rocked back to encourage Chet to give me more. He fed me a few more inches, and I felt the head rub against my prostate, sending a jolt of sensation through me. Again, he pushed in, and this time I felt a stab deep inside as he bottomed out.

"Shit!" I hissed through gritted teeth. He immediately stopped and pulled back a bit.

"Sorry man, you okay?" I nodded, and he gave me some short strokes. The shock of the pain gradually wore off, and I began to enjoy the fucking I was receiving, squirming and moaning as he hit my prostate each time. I wanted to take all of him, so I rocked back again, taking more of his length, and I could feel it when he bottomed out. Now I was ready for it, and even though it felt uncomfortable, I knew I would get used to it. Sure enough, after a few more strokes, I felt his body against my ass cheeks. He was all the way inside me, all 9 inches plus.

"Ooo, I love your ass." Chet whispered. He put his hands on my hips, pulled out most of the way, then in one smooth motion pushed back all the way in. And then he repeated it, over and over, giving me a real fucking, like I had never had before. It was amazing! I was almost delirious from the pleasure he was giving me. My cock was pumping out a steady stream onto his couch, and twitching every time his head rubbed over my prostate. I could hear Chet breathing heavy, groaning and swearing softly from the effort he was putting forth, but he never changed his pace, keeping up the long steady strokes. We stayed in that position for several minutes, my on my knees, and Chet pumping away behind me, fucking cum out my hard cock with every stroke.

He must have been getting close, because I felt him change, the strokes becoming shorter and faster. Now his ball sac was slapping against mine, and his hips were making audible smacks when they hit my ass each time, sweat dripping off his head onto my back. I tried to squeeze down, to make more friction, but it barely slowed the black monster as it pounded into me.

"Ungh, ungh, ungh." Chet growled on each stroke, then he pulled my hips back, and thrust into me as hard as he could. All I could do was hang onto the couch as he bucked and jerked with his cock deep inside me, dumping his cum into the condom. I felt him lean forward onto my back, and I bore his weight as he regained his breath, my head swimming from the surge of sensations I'd felt in the last couple of minutes. I looked down, and saw the wet spot my cum had made on his couch, and hoped he wouldn't be upset. Then Chet raised off my back, and I felt his cock slide out, followed by an empty feel inside.

After we cleaned up, we went to his bedroom, and knocked back some more beer. An hour passed, and I asked Chet if he was up to another round.

"Put that thing in your sweet mouth, and we'll find out." he laughed. So I did, and I sucked him back up. When he was good and hard, I lay back, and spread my legs, offering myself to him. "I don't have another condom. I know we're both clean, but it's up to you."

"I trust you, and I want you to fuck me again. I don't want to wait."

He nodded, and lubed me up, and threw my legs up on his shoulders, putting my ass right in front of his cock. Giving it a layer of lube, he found my hole, and pushed it in. No pain, of course, I was well stretched, and he wasted no time giving it to me. He gradually pushed my legs over on to my chest, until he was laying on me, and he could get even deeper inside. I was almost drained from the first time, but still managed to dribble out some cum onto my belly. Chet's ass bounced up and down, driving his cock into me, fucking me for several minutes without letup. The man was an incredible lover, but even he had his limit, and I felt him tense up, and drive deep inside one last time, emptying his balls of cum, and leaving it inside me. Now we lay face to face, our hearts pounding and gasping for air, both totally spent.

After that night of amazing sex, I kept going back for more, and Chet kept giving it to me. We became a couple, and he eventually moved in with me. For me, as a confirmed bottom, I had found the perfect top, and also a lover and friend.