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This is a True Story
Although I'm normally a bottom I have topped a couple of times. They were both boys, young boys. College age. The most memorable one was George.
We exchanged a few emails, and pics, and I invited George over. He showed up on time. I met him at the door in the nude. I already had an erection.
This was back in the day when the only ED drug I ever found that didn't give me migraines was still on the market. It gave me an erection, on demand, for three days. It enabled me to perform on a livestream sex channel. I would start out "dressed"--in wig and makeup, a bra, panties and thigh-highs (or sometimes pantyhose)--and as the requests from chat room viewers rolled in, I would undress until I was naked. My lips were painted red, bright-red, and viewers would praise my "Cupid's mouth." They would tell me I had a "nice clit." And when I bent over and spread my cheeks, they would tell me I had a sweet "manpussy." I would fuck myself with a jelly dildo.
Viewers would ask me to fuck myself with a cucumber, or zucchini, but I quickly found out this wasn't allowed. You could only use a dildo. My hole was open in those days and my thick vibrator went in easily. I had a youthful-looking body and the wig and makeup took twenty years off my face. When viewers looked up my personal information they couldn't believe my actual age. Most thought I was in my thirties. One young guy even suggested I was only twenty-something. It was flattering. And I enjoyed showing off in front of the men, and pleasing them. I stroked myself, of course, but despite constant calls for me to, I never came. Never ejaculated. Not on camera, anyway.
I received offers from multiple men to come visit them. Or, even, to "marry" them. Curiously, most of these offers came from people who lived in the south. Alabama, Tennessee, North Carolina. One man, in London, offered to fly me over and take me around to shows. Plays in the East End. An older man in California offered to fix me up with the best plastic surgeon in his state. In order to get a boob job. A pair of tits, even B-cups, plus a cock and balls? Believe me, I was tempted.
But I've gotten off track. Back to George.
Although he'd seen a pic of my hard cock already he now looked at it, and swallowed, and said, in his soft, overtly effeminate voice, "You have a nice one." I thanked him. Without me having to ask him, George began to undress. He draped his shirt and pants over the back of a kitchen stool. Now he was down to a panty.
This warmed my heart. Another crossdresser! I approached him and put my hand beneath his balls. I fondled them gently in the silky microfiber. They weren't large, about the size of mine, a four, say, on a scale of ten. I pulled my hand away and George removed the panty. Now we were both naked.
He looked around my livingroom, nervously. He looked back. "Do you want me to suck you?" There was uncertainty and apprehension in his voice. I've always enjoyed sucking cock, and I've sucked perhaps a hundred of them. I always swallow. But not everybody shares my appetence. My delight. Just ask my second wife.
"Sure," I told him. "But just for a few minutes."
The ED drug improved my stamina but I've always been a quick cummer. A premature ejaculator. Just ask my first and second wives.
George sank to his knees on the hard tile and sucked me rather haphazardly. He never seemed to get a rhythm down. And he never fondled my balls, let alone reached around and caressed my ass. I held, loosely, the sides of his head as he sucked me. George had thick, dark hair and wore it in a kind of Prince Valiant cut. Its just-washed brilliance shimmered in the overhead light.
Eventually I pushed him away and George leaned back and wiped his mouth. He wore an embarrassed look--as if he understood he was not very good at giving head. He got to his feet. He looked around again.
"Where do you want to do it?" he asked.
"On the couch?"
"You have lube?"
"Yes." I went and opened the outermost kitchen drawer and removed a tube of K-Y jelly. George stared; he blinked. He must have thought that I fucked a lot of guys in my livingroom if I kept a tube of lubricant in a kitchen drawer! I started to tell him that I was usually the one bottoming, but I remained silent.
Again, without me asking, George bent over the near arm--rolled vinyl--of my livingroom sofa. My second wife was Italian and she'd bought it. It was light grey in color--kind of a tan-grey--and made to look like leather. Though it would have fooled no one. I always called it "the Soprano couch" because it was identical to the one in the livingroom of Tony Soprano's house, in the HBO gangster series.
George's upper body, his turned head and shoulders anyway, rested on the first seat cushion. George was not fat but he was plump. He had a soft, plump body and his ass, displayed beneath me, was plump and round and unblemished. I parted his cheeks, exposing his crack and his anus. It was pink. Pink-grey.
I bent my cock to it and pushed my head in. I pushed deeper. His hole was open and smooth and clean. He obviously was no virgin. When I entered him all the way, my pubic hair flush with his crack, he let out a moan.
"You OK?" I asked.
He nodded--against vinyl cushion's surface. I pulled back and pushed in again. I began fucking him. Fucking George. He hadn't asked me to wear a condom--there were foil packets in the drawer--and I hadn't volunteered. I was barebacking him. I wanted to bareback him. I wanted to shoot my load in him. It had been at least three days since I'd masturbated. Ejaculated, that is.
After about five minutes of this, pumping George, he said, cried out more like it, protested, "This isn't very comfortable."
I pulled back, and out of him, as he rose up. I could see his point. The right side of his face was rubbed red.
"Let's go upstairs," I offered. "To my bed."
George followed me up the stairs, and I pulled the bedclothes back, and George got on his hands and knees, and I got behind him and entered him again, and we resumed fucking. I'd bottomed for so many guys that I'd forgotten how good it felt to be on the other end of things. The feel of your cock sliding in and out of a smooth, deep, tight but too tight, hole. It was a marvelous sensation. Better any day than fucking a vagina. My first wife had let me butt-fuck her at times; but my second wife, never. My first wife began cheating on me, openly, while we were still together. My second wife left me, moved away and quickly remarried. I began having sex with other men, resumed having sex with them, I should say, almost as soon as my second wife was out the door. That was nearly fifteen years ago.
My first wife knew about my gay fantasies (and realities), as well as my cuckold fantasies. Whispering about them was part of our foreplay. I suspect, towards the end, she knew I was gay. Bi at any rate. My second wife wasn't into kinky stuff. Therefore she knew--suspected--nothing. At least that's my assumption.
After about five minutes of hard pounding I came in George. After I pulled out, and backed away a bit, George looked over his right shoulder and said, smiling, "I could feel you ejaculating in me."
You could, I wondered? I'd been fucked many times and never experienced that sensation. Though it sounded delightful.
I went in the master bathroom and wet a hand towel and wiped my drooping cock clean of lube and did the same to George's crack. Otherwise he--we--were pristinely clean. I was thankful for this. Thankful to him for this.
Downstairs, as George quickly dressed, I offered him a drink. He declined. Said he had to go. It was George who was acting like he'd just ejaculated, and abruptly lost all interest. I felt, for once, rather buoyant. Triumphant. I'd just fucked a boy! My cum was inside him!
"If you want to come back," I told him, "you're welcome. We can do it again," I added, hopefully.
"We'll see," he replied, in his soft, but firm, effeminate voice. It didn't sound promising. I opened the front door for George and he left. No hug goodbye. Nothing.
I never saw or heard from George again. The email I sent him that night, thanking him for coming over, and letting me fuck him, went unanswered.
I decided, afterward, that George thought I was too old for him. Without my wig and makeup on, from the neck up I looked my age. I was old enough to be George's father, and then some, after all. It pained me a little but I got over it, and went back to sucking cock and occasionally bottoming. Often--usually--for blue-collar guys.
I also began offering my services as a nude housecleaner. Three hours' work for $45. Plus a $5 surcharge if I had to travel more than ten miles (I usually did--to the next county). Elderly guys mostly. Sometimes snowbirds. If they wanted to fuck me it would cost them an extra $40. Few took me up on this. Men are cheap. And rather limp, in many cases.
My "services" included a complimentary blowjob. I made this clear in the rates I sent prospective clients in an email. Some wanted their blowjob right off the bat; others toward the end of my stay. I worked hard, however, and generally walked away with $60 (tip included). I scrubbed their toilets, as well, and, for some reason, always got an erection while I did so. I guess, because, kneeling their on the tile floor, to the side of their "throne," it's the ultimate in submission. At any rate, I would usually treat myself to a nice meal, with wine, later that night.
Make no mistake. I enjoyed fucking George, and that other boy (my memory of him is dim) as well. I imagine George paired up with another college kid. Or, if he truly wanted a surrogate dad, a top in his thirties, or early forties.
Whatever, I wished him well in his adventures.