“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.