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The Joys of Penetration - Part 1

You're never too old to learn
The last year that I was living in Florida, I was dating a woman named Phyllis who had an interesting perspective on oral sex. While she had no problem providing it, she wasn’t real keen on having it performed on her. As she told me on numerous occasions, her sexual preference was penetration. Vaginal, oral or anal; it didn’t matter as long as she was being penetrated. Preferably culminating in copious amounts of ejaculate being injected.

“Penetration’s the thing!” she’d declare. “There isn’t anything like being fucked hard and then feeling that dick twitch and pulse as it fills you with hot cum!” It got to the point where foreplay was reduced to me telling her how hard and how fast I was going to fill what hole with my dick until it was pumped full of spunk. Which actually got kind of boring after a while, and so I told her so one afternoon.

“You just don’t understand because you’re a man” she said. “If you had ever felt the joys of being entered and filled with a good, hard cock and then having it slide in and out, over and over again; if you had ever experienced the feeling of a pulsing member shooting jets of hot jizz inside you; then you’d know what I mean.” As I mulled that over, she suddenly got a glint in her eye and said “Hmmm, maybe you can.” “What do you mean?” I asked. “You’ll see,” she said, “you’ll see.”

The next afternoon I stopped by Phyllis’ to drop off a book I had borrowed. When she answered the door, she had one of those big, shit-eating grins on her face. “I’ve got a surprise for you” she said. Taking my hand, she led me to the bedroom and instructed me to take off my clothes, lie down on the bed, and close my eyes. Intrigued, I complied. “Now,” she said, “I’m going to go slip into something more appropriate. You keep those eyes closed.” With that, I heard her leave the room.

After about two minutes, I heard her come back in. By the sound of her breathing, I could tell that she was excited. “Open your eyes," she said. I did, to see Phyllis standing before me, naked, and sporting a strap-on dildo that made my eight-inch hard-on look pre-pubescent by comparison. “What are you going to do with that?” I asked. “I’m going to show you the joys of being penetrated,” she replied, a combined look of lust and joy affixed to her face.

Eyes wide, I said those words that I am sure many reluctant virgins said, or at least thought, at their deflowering; “There’s no way you’re going to stick that huge cock into any hole of mine!” Jumping out of bed, I got into my pants, zipped up, and left. It was the last time I ever saw her.

For the next couple of years, as I drifted in and out of several so-so physical relationships with other women, Phyllis’ fixation on being fucked and filled was always at the back of my mind. I even have to admit that the vision of her standing there in her humongous harnessed fake cock crept into more than one erotic dream. I could just never bring myself to call her up.

Then, one night, I ran into Marty, an old childhood friend of mine, in a bar outside DC. Marty and I were friends from second grade on until we both left town our senior year in high school. Both of our fathers were federal employees, and they were both transferred far enough away that year that we both had to move. Marty was the guy who first told me about sex, and the guy who showed me how to masturbate. In fact, during junior high many of our “campouts” in my tent in the back yard were just cover for mutual masturbation sessions, until Marty wanted to go a bit farther. Back then, it never occurred to me that Marty might be gay; it probably never occurred to him, either. But as we caught up on each other’s lives in the bar that night, it was clear to me that he was indeed gay.

About five scotches in, catching up turned to reminiscing, and it wasn’t long until we recalled our times in the tent. Marty then admitted that he was gay; and that he had always wanted us to have more than a “hands on” relationship. I told him that I didn’t think that I could ever get my head around giving head to another guy, or letting him fuck my ass. Marty sighed and just remarked “You don’t know what you’re missing.”

“Funny,” I said, “my last serious girlfriend told me the same thing.” Half joking, Marty grinned and said, “Maybe she’s right.” After one more drink, we called it a night, but made plans to have dinner at six the next evening at the restaurant in the hotel Marty was staying at.

Needless to say, dinner that next evening was more tall tales of life after high school, mixed with exaggerated recollections of our youthful escapades; all fueled by not one but two bottles of a very fine Merlot and an Irish coffee at desert. We were both feeling rather mellow when Marty invited me to his suite for a nightcap from the mini-bar, which I accepted. When we got there, he handed me his extra key card and the ice bucket, directing me down the hall to the ice machine. “Don’t bother knocking,” he said, “just come on in when you get back.

Well, it took nearly ten minutes to get some ice, as the first machine was out of order and I had to go to another floor. When I finally got back, I opened the door with a flourish and announced, in my best Ricky Ricardo, “Honey, I’m home!”

“Back here,” Marty replied, so I followed the voice to the interior sitting area. To my surprise, while I had been gone Marty had changed out of the business suit and tie he had been wearing, and was now in a tank top and chinos. Pointing to the space on the love seat beside him, he said, “C’mon, ditch the coat and tie, kick off the shoes, and get comfortable.” Still feeling the buzz from dinner, I had no problem with that suggestion, and we were soon side by side sipping a scotch on the rocks, feet up on the coffee table.

We were both just sitting there, just kind of mellowing out, when Marty turned and said, “So, have you thought any more about being penetrated?” “Not really,” I said. “If you had seen what she wanted to fuck me with, you probably would have said no yourself.” With that, I related the story of the surprise that Phyllis had concocted for me. Laughing, Marty had to agree that for a “maiden voyage”, a hard plastic monster dick probably wasn’t the best way to go. But then, laying a hand on my thigh, he reminded me in a husky voice that his own erection was nowhere near as daunting, and would make an ideal first time.

I had to admit that his touch brought back memories of our campouts, and there was no denying the urgent surge that I felt in my penis. Marty must have noticed as well, because his fingers were soon trailing up my leg, coming to rest on my now rigid member. I looked over and saw that he was erect, as well. I reciprocated the touch, so that we were now re-enacting the mutual stroking that had consumed many hours of our boyhood together. In no time I had released his swollen manhood from its confines, and he was right; erect he was slightly smaller than me, and did not seem to pose the threat of physical harm that Phyllis’ fake phallic did.

Ever so slowly, Marty directed my head closer to his crotch until I was face to face with his cock; its prominent purplish head dribbling pre-cum. As if by instinct, I opened my mouth and took it in, licking the ridge just the way I would have wanted it, one hand pumping his shaft while the other massaged his sack. I began to slowly bob my head up and down as I varied my suction; sometimes taking him in almost to the hilt, while other times stopping when just my lips had passed his crown. I was giving my first blow-job!

I hate to admit it, but as I did all the things to Marty that I liked in a good suck myself, his enthusiasm made me go at it just that much harder. His excitement became my excitement, and soon he was pistoning in and out of my mouth in what could only be described as a face-fuck. And here’s the kicker; it was great. He was possessing me in a most personal way, and I was loving it. And then it struck me; I wanted him to come in my mouth! I needed him to come in my mouth! Just as he was about to spew, I held his hips still so that his cockhead was resting in the middle of my tongue. Suddenly, his dick enlarged just a bit more, and then I felt the pulsing of his shaft as glob after glob of hot sperm bathed the back of my throat.

I swallowed what I could; the rest I swirled around Marty’s softening member as I held him captive with my lips until finally releasing him. Even though he got most of the pleasure, I was in control. It was empowering. And I said so.

With a smile, Marty said “You’ve only learned the first half.” “What do you mean?” I asked. “First, let me return the pleasure,” he said as he resumed stroking me through my suit pants, “and then we’ll continue your education into the joys penetration.”

To be continued…

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