As a kid, I had always fantasized about what it would be like to have sex with other boys, hell, girls for that matter. I even harbored the hidden desire of being molested by an adult like a coach, priest, scoutmaster, etc... even as far back as my pre-teen years. I would have been an easy mark for any predatory adult or older kid who wanted sex from a young boy. But it never happened...probably a result of my innate shyness, or my fear of rejection or ridicule if I were to suggest such a thing to another kid. I was extremely shy when it came to putting moves on girls that I would date - even thru high school.
When I was 12 or so, I remember having a big crush on my best friend's younger sister, a really cute Natalie Wood look-alike. She was a year younger. I used to get quite aroused when I was lucky enough to catch a peek up her dress or shorts to her underpants when she got careless. One day I got so excited after such a peek, that I grabbed a pair of her discarded panties from her bedroom floor. They were the ones she had actually been wearing earlier. I stuffed them in my pocket, and immediately rushed home with my new forbidden treasure. I had no sisters, so I was totally unfamiliar with girl's underwear. I examined and played with her panties for hours, even wearing them and pretending I was her in front of the mirror looking up my bathrobe. I got so aroused that night that I masturbated for the very 1st time, while sniffing her exciting female scent. Alas....I had my first orgasm and even ejaculated semen. What an exciting discovery for a young kid - a defining moment in my sexual development, for sure.
And after that erotic episode I was hooked....both on masturbation, as well as enjoying doing so with panties I would purloin from girls that I knew in my neighborhood. This went on for years, thru college and even into adult life. I became a compulsive masturbator; an activity I enjoy even to this day. This was to be my sole sexual outlet for many years, in lieu of what many of my friends enjoyed with girls they dated.
Then, at long last, came my first encounter with another male. I was in New York City on a business trip staying at the Algonquin Hotel. I was in my late 20's at the time, living in St. Louis, and travelling quite a bit in my job. During this heavily travelled time in my life, I masturbated almost every night while on the road in my various hotel rooms, and I was now fantasizing more frequently about having sex with other guys. I had taken to bringing my 35mm SLR and Super 8 movie cameras with me to take pictures of me jacking off and cumming. I then had these developed at a mail-order place that had advertised in one of the porn magazines, then sent to a PO Box I had back then. I was married with kids by then, but this masturbation habit stayed with me as a hidden and secretive part of my life - totally separate from my normal and very happy home life. I had also become somewhat addicted to jacking off in adult porn theaters and video booths, and found that I was starting to prefer the gay videos more and more. I guess this must have been telling me something?
It was in one such adult bookstore/video arcade that I would meet the young man who would introduce me to M2M sex. I'd never considered myself gay, rather bi-curious at that point. It was an early spring evening in Manhattan, and 42nd Street was teeming with all the activities and business that catered to horny businessmen (not like it is now after being gentrified). I was prowling around this one bookstore, getting nice and hard reading the xx magazines, and strolled back into the dimly lit corrider that separated a dozen or so coin-op video booths in the back of the store. I had just come out of one of the booths, with my erection pretty obvoius under my pants, when I encountered Michael. He was barely 21, beautiful, about my size, blonde, slim, very boyish looking, and appeared to be pretty sure of himself. We said hello, and casually mentioned that he was out of quarters and asked if I'd like to share a booth (a great line). I hesitated at first, then accepted, and the adrenalin started pumping inside me. This was a real big step for me, and something I'd never done before. We both stepped into a booth, popped in some quarters, and watched a video of two guys sucking each other off. He asked if I liked that, and I nodded; nervously I expect. Then he reached down and started to rub my rock-hard penis. I liked it. Given my state of arousal, it seemed perfectly natural that I do the same to him, and I did. He had a nice stiff erection under his pants too. We fondled each other for awhile, when he asked if I had a place we could go and be more comfortable. I was pretty well worked up at that stage, and I recall looking into his eyes, saying, "How 'bout my hotel room?" He nodded.
We left the store and walked up 42nd St, across Times Square to the Algonquin. I was a little paranoid, so I gave him my room #, asked him to hang back and then follow me up to the room in a few minutes.
I went up and stood in my room, heart racing in anticipation of all my fantasies finally about to come true. Did I really want to go thru with this? I dimmed the lights, cleaned up my papers, brushed my teeth, checked my hair, etc....a lot of nervous energy going on. I felt cock starting to get hard again. Finally there was a knock on the door.
Michael stood there - in his waist-length demin jacket, close-cropped blonde hair, and enticing smile. He entered, and promptly removed his jacket, walked over to me and, wasting no time, grabbed my stiffening penis and started rubbing me up and down, while nuzzling my neck......I was fully erect again in no time. I told him that I'd never done anything like this before, and that he'd have to giude me thru what he wanted me to do. He said, "You're kidding - a virgin?". I said that I'd dreamed about doing it with another guy for years and had masturbated constantly thinking about it since I was 12. As he rubbed me thru my slax, he assured me that all the things I had fantasized about would come very naturally. I had some small airline bottles of scotch, and I nervously suggested that we have a drink to get us in the mood. He said, "Great idea. It'll relax you". We drank scotch and talked for awhile about my sexual inexperience. Finally he stood up and said he was horny, and couldn't stand waiting any longer. I turned the lights down even further, and tuned to some mellow jazz on the radio. He sat on the end of the bed while I stood facing him. He started slowly undressing me as I stood there, and soon I was down to my white "Calvin Klein" briefs with my erection poking straight out under the cotton. Then he stripped naked himself as I watched. He knelt down in front of me, and slowly slid my underpants down to the floor. My hardon sprang out as he slid the waistband down. Before I knew it, he leaned forward and his mouth was wrapped around my penis and he was sliding his tongue up and down on my hard shaft from the head to my balls. My eyes rolled back in my head in pleasure, and my knees almost buckled. Then he moistened his finger, reached under my balls, and slipped it into my asshole as he sucked. God, it was really happening! I looked down and he was fully erect too, and was stroking himself with his other hand as he worked on me. I moaned with pleasure and whispered how much I was loving it. Then he laid me down on the king-sized bed and spread my legs, and continued to lick my penis and then worked his way down to my asshole, lifted my legs in the air, and worked his tongue up my anus as he jacked my cock. It was ecstasy! We did this for a long while. Then he looked up and asked what I wanted to do next. We switched postitions, and I started examining and stroking his cock and balls, masturbating him for awhile. I'd never actually touched another guy's cock before....and it felt nice.
He asked if I'd like to take his cock in my mouth. I was now stroking myself slowly as I knelt between his spread legs. I hesitated, but the sight of of this very attractive young man, stark naked with his erect penis jutting straight up from his balls and pubic bush really turned me on. It seemed only natural that I bend down and take him into my mouth. What an incredible sensation it was to actually have another boy's erect cock in my mouth - for the first time. I kept thinking, "This was no longer fantasy...it's really happening!" I sucked off Michael for a good five minutes, enjoying every minute of it. With my tongue, I explored his cock head, piss slit, the shape of his helmet, his balls, then back up his hard shart, then back down. I thought, "God - is this what I've been missing all those deprived years?"
Then he picked his head up and asked me if I'd ever been fucked. I said, "Only with a dildo when I masturbate. It's in my suitcase". He replied, "Why don't you get it out"? I did. He stood up, pulled some lube out of his jacket, and started running a greased finger in and out of my asshole as he applied lube to the dildo at the same time. He worked in one, then two, and finally four fingers to open me up. Then he propped two pillows under by butt, and very slowly pushed the well-lubed dildo into my waiting asshole as he masturbated my cock with his other hand. This went on for quite some time. Finally, he asked me to turn over and get on all fours. He got behind me, and gradually I felt him slide his erect cock into my anus (no condom - this was much before AIDS and all that). It hurt a little at first, but he was patient and went slowly. Finally he was all the way inside me, and he started pumping in and out. After a few minutes of very pleasurable fucking, I could sense he was getting worked up and close to orgasm. I was in such a state of pleasure that I didn't care at that point where he shot his load. Then he arched, stopped pumping, and I could feel the intense spurts of his ejaculation pulsate inside my asshole, as he spurted his big load of warm cum up my ass. Finally he pulled out and flopped back on the bed, exhausted, next to me. I was still face down, but I could see semen still oozing out of his still-hard penis. We lay there breathing hard for a few minutes. Then I adjourned to the bathroom, sat on the toilet, and could feel his sperm flowing out of my asshole. I loved it when I could hear it as it plopped into the water. I was still in a state of sexual euphoria.
After quickly cleaning up, I came back into the room, and he was still laying there. He beckoned my over to the bed and gestured for me to lay down. He spread my legs wide again, knelt between them, and started to suck me off again. I was completely hard again instantly. He started jacking off the lower part of my cock, with his lips tight around the head, as he sucked and licked me. Pretty soon I could feel feel my orgasm coming on. And so could he. He slipped a few fingers up my well opened anus again and quickened his pace. Then it came! I erupted with a big full load of cum into his mouth as he masturbated me. And boy, did I cum that night.....with an intensity that I had never before experienced. He didn't spill a drop. When I had shot my last spurt, he looked up into my face, smiled, opened his mouth to exhibit the new gift on his tongue and swallowed it all as I watched with rapt attention. God, it was hot!!!!
So there you have it....we were both completely spent after that intense session. Afterwards, I took him out for a killer dinner, and he gave me a tour of some of the gay nightspots in midtown Manhattan. I didn't get back to my room until after 3A. I never saw Michael (if that was his real name?) again, although I tried to phone him on subsequent trips. But what happened that night broke the ice, and was my very first homosexual experience of many more that were to follow. Sure took me long enough. The rest is history.
I sincerely hope that you enjoyed this true, albeit brief, account of my very first homosexual experience. That is exactly the way it happened that night. If anyone reading this story has anything of a similar nature they'd like to share, or if, by chance, you happen to be reading this - Michael, I'd love to hear from you.
Thank you, Will Anderson
big69will42@yahoo.com