I confess that I had my first sexual experience with another man last night.
I've fantasized about being with a guy for a long time. I'm not attracted to other men, but the idea of sucking another guy's dick, having a man finger my butt or even having a guy fuck me in the ass has always turned me on. I've bought toys - dildos, buttplugs, prostate massagers, etc - used them on myself and had some amazing orgasms...but I'd always be fantasizing about a real dick sliding up my ass.
After a going through a recent sexual drought, I finally decided to get over my shyness and fulfill my fantasy. I responded to a couple of interesting ads on Craigslist and found a guy who sounded decent and was interested in some of the same things I wanted to try. We corresponded a bit, then agreed to meet up in public and get a hotel room for the night to fool around. He was about 10 years older than me (mid-40s), slightly overweight, average height and a bear; he seemed decent during our brief public conversation and we discreetly got a room.
There was little conversation once we got in the hotel room, as we both quickly stripped and got things started. Neither of us was into kissing or embracing or anything like that, just looking for sex. I'd indicated in our correspondence that I was looking to bottom and be more submissive, while he was interested in being more dominant. He sat down on the bed and I got down on my knees in front of him, with his cock in my face. Prior to this, I'd never had a close look at another guy's dick. His cock was average length (five to six inches) and slightly thicker than mine, while his bush and balls were unshaven. I cupped his balls with one hand and started stroking the base of his shaft with the other, then finally slid the head of his cock into my mouth. I didn't try taking it very deep, as I have a hell of a gag reflex, just sliding it in and out a little and running my tongue around the head and along the underside. I'd pretended to give blowjobs on my dildos before, but this was totally different. The taste of his cock, how it felt in my mouth, his balls in my hand...incredible. From his groans, he was clearly enjoying it. After awhile, I felt his cock throb and the head flare in my mouth - at first, only once every couple of seconds, then more frequently - and I got my first taste of his pre-cum. At that point, he told me to sit on my hands and just use my mouth. I obliged and focused just on sucking him, until he put his hand gently on the back of my head and his cock began to pulse. I've eaten my own cum before, but having a load shot directly into my mouth was entirely different. Usually, by the time I'd get my own jizz in my mouth, it would have cooled and started to become clumpy. His load was a spurt of warm liquid directly onto my tongue and down my throat. Each time his dick would pulse, another burst of sperm would flood my mouth and I think he shot five spurts before he was finished. He told me to keep his dick in my mouth and suck out the remaining cum until he went soft, then had me kiss each of his balls and thank him for the jizz.
He told me we had some time until he was hard again and that he'd use it to prepare my virgin ass. By this point, my dick was throbbing and I desperately wanted to cum, but he told me I wasn't allowed to yet. He instead had me get up and bend over a small table in the room. He then put on a set of latex gloves, spread my ass cheeks and told me to keep my eyes forward. I did and soon felt a cool fluid applied to my asshole and the surrounding area. He began to rub my hole with a well-lubed finger, slowly, in a circular motion and gradually applying more pressure. I tried to relax as much as possible as he slowly pushed the tip of his finger through my outer sphincter and continued his slow massaging of the inner ring of my asshole. During my solo play sessions, I've fingered my own ass, but the sensations of having another man sliding his finger slowly up my butt was entirely different. On my own, I could control the speed, depth and pressure of the movement, but here I had to just accept his movements. Finally, my anus yielded and his index finger was inside me. The slight pressure in my butt felt good and I enjoyed it for a few moments before he began to stroke my insides, the beckoning motion of his finger searching for my g-spot. When he finally found it, the sensation was incredible. My urge to cum shot up as pulses of intense pleasure went through my dick with every motion of his finger. The feeling was so much more intense than any of my attempts at massaging my own prostate. I couldn't decide what I wanted more - to cum or to have him fuck me. I think I begged for both at one point. Buried in the pleasure was a feeling of increased pressure on my asshole as he started to work his middle finger into my ass. With both of his fingers inside me finally, my butthole started to hurt a bit, but I forgot about that as he intensified the prostate massage, using both fingers. I pleaded for him to milk me, to jerk me off and let me cum, but he still refused. It wasn't time for that yet...it was time for him to fuck me.
Keeping his fingers up my ass and me bent over the table, he presented me with a condom and made me unwrap it and slide it over his stiff cock. I kissed his balls again, at his request, then he had me apply lube to his sheathed cock. Finally, he withdrew his fingers from my hole, took off the glove and positioned himself behind me. He pressed the head of his cock against my asshole gently at first, then increasing the pressure until my anus spread for him. As he pushed in, I relaxed and pushed back against him - within a few seconds, he was inside me. I'd put dildos up my ass before, but this was a completely different experience. His cock was warm and moved inside me as he shifted position; it felt like he was so deep up my ass and his girth stretched my anus even further. I could feel his bush against my ass cheeks and his balls against my upper thighs. After giving me a few seconds to adjust, he started to fuck me. He started slow at first, drawing his cock most of the way out, then sliding it all the way back in slowly. His strokes would catch my prostate on occasion and I couldn't help but moan as ecstasy shot through my dick. He changed up his thrusts, pulling out maybe an inch, then pumping back in, keeping his cock deep inside of my rectum. After a few minutes, he pulled his cock out most of the way, staying inside me only an inch and doing shallow thrusts, which felt so good on my prostate. Once I'd relaxed enough, he withdrew his cock completely, allowed my ass to close a little, then thrust back deep inside me. The first time he did this, I moaned especially loud and begged for more - after that, each time he withdrew, he told me to beg before he'd put it back in again. And I did. Over and over. He then thrust deep into me, laid on top of me on the table and began to thrust more rapidly - deep, hard, fast pounding of my asshole. His breath quickened in time with his thrusts and it felt like his cock was swelling inside me. With a final groan, he shoved his dick as deep in me as he could - I could feel him pulse even through the condom and knew he was cumming, finally cumming after almost 15 minutes inside my butt.
He withdrew his dick from my tired asshole, took off the condom and laid down on the bed, then beckoned me over. He had me straddle his thighs and then he began to finally stroke my dick. I came in less than 10 seconds, my throbbing cock finally getting release. I pumped out more jizz than I think I ever have in my life and he made sure it all ended up on his dick and balls. When I was done, he squeezed the contents of the condom out onto his cock, mixing our loads, and had me lick him clean. I was still shaking and weak from the intense orgasm and thorough fucking, but did as he said and cleaned up all the cum from his body. With that completed, we both dressed and left.
My writing may not convey it as well as I might like, but it was an amazing experience. I've never felt such intense pleasure, never thought it would feel so good to be fucked in the ass and never cum so hard. He's already sent me a message suggesting we do it again, though he'd like me to show up with a buttplug in next time, so my ass is already prepared and he can just pull my pants down and pound me. He's also suggested maybe bringing a few other toys or even having a longer meet-up, so he can give me a real prostate massage and spend a few hours with his cock in my ass. I'm already looking forward to it.
