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.
