Copyright © 2002 by the author
I'm a 40-year-old male, tall and heavyset (okay, fat), moderately attractive with blonde hair and beard, not spectacularly well-endowed, and I've always had a bit of the submissive in me. When I was in college I led a really wild sexual life, the kinds of things that my friends now would be totally shocked by but which I find myself remembering when I jack off (which is frequently). By the time I finished school and got out in the real world, I'd put that stuff behind me, though I still thought about sex. Still being basically oversexed, I began having a fantasy where I would tell a woman I know about my past and the things I liked (and still like) to do. Then I started using phone sex services and setting up this fantasy, and a couple of the women I talked to added some elements that made me really hot. I always partook of my lusty dream with a dildo up my ass (I am bisexual and enjoy cock almost as much as pussy and ass) and stroking my 5 inch dick.
In a nutshell, the fantasy goes like this: the woman calls and we end up in a contest for me to shock her and for her to resist being shocked. Of course the things I tell her get viler and filthier, and eventually she gives up and gasps out that I am indeed a disgusting pervert. The phone sex ladies added the idea that the woman actually likes the things I'm telling her and I end up being her sex toy.
Which brings us to the point of my writing: This summer a really hot, young woman came to work at the company where I'm employed. Her name was Jill, she was 19, and she made me so fucking horny I couldn't see straight!Ê We struck up a friendship, and had a lot of leading talks and some pretty explicit conversations. I hinted at my "dark and dangerous" past, but she just laughed and said she'd been pretty wild up until she was about 16 and anyway I was such a nice guy...
One night about two weeks before she went back to school, I handed off my workstation to Jill at the end of my shift. She was wearing a light summer dress and when she leaned over me to clarify some things that needed to be done, I had a clear view straight down the front of her dress.
Jill is a petite, curvaceous woman, with curly brown hair and the most adorable freckles, and a body honed by aerobics and her years as a high school cheerleader. I now found out that she disdained underwear because I could see her firm, round breasts and large (stiff?) nipples, straight down her sexy belly down to the glorious V between her legs which I was pretty sure was shaved clean as a whistle!
Fool that I am I took this sight in for about 15 seconds then nobly turned away, finished the hand off and high tailed it for home, not even pausing for our usual shift-change conversation. I got home, stripped, and was in bed with a dildo in my ass and my hand on my dick before you could say, "I want her BAD!" I slipped right into my favorite fantasy, imagining Jill hearing from my lips how nasty and perverted I was, hearing her gasps, and then hearing her lust-laden voice telling me what a filthy pig I am.
I was just about to cum when the phone rang. I could have screamed! On the other hand, the idea of building back to climax was kind of nice so I answered.
It was Jill. She'd missed our usual talk and wanted to chat now. Of course, I was all out of breath and she wanted to know why--had I run to the phone? I said no and she giggled and asked if I'd been jacking off. My cock leaped to attention and suddenly I wanted to act out my fantasy for real.
I admitted that I was, and she wanted to know if I was thinking about looking down her dress. I could have died, but even more so when she said I could have enjoyed the view for longer, She was pleased I found her to be sexy and she thought I was pretty sexy too! What could I say? Like I said, I'm not exactly slim, in fact I'm downright fat, even if I do have a nice face and a good personality. Here was this sweet and sexy young woman teasing me, telling me I was sexy to her! I started stroking my cock.
"You need to loosen up a bit," Jill continued. "Enjoy the view, you know? There's nothing wrong with sex, and anyway, you're so damn nice you're kind of hard to put up with sometimes."
Shit! The perfect come on to my fantasy!
"Umm, well," I said, "I told you that I'm no saint, Jill. I had my wild days in college, and I still think about them and..." I cleared my throat, "... and I jack off a lot. I'm not as nice as you think."
"I don't believe it," she replied, and then there was a long pause. Finally she said, a bit huskily, "What do you think about when you stroke your cock?"
"Are you in the office?" I asked. "This isn't exactly the kind of conversation you want other folks to hear!"
"No, I'm at home. Work was slow and they let me leave about an hour after you left." Well, that was all right. I had had horrific visions for a moment of our boss walking in and hearing Jill's end of the conversation.
"I think about the things I like," I said.
I cleared my throat and stroked my cock hard. I needed that jolt of lust to get me to throw caution to the winds. It worked.
"I love asses best, I love to fondle them and kiss them and look at them. I love to jack-off. I'm even bisexual." There was a silence, and then Jill laughed.
"So? That's your deep dark inner secret? You're no different that a million other guys--or girls, for that matter. Shit, you're not any different than ME!" I felt a raunchy thrill deep inside. Was Jill saying she was bisexual? I flashed on Jill with her pussy grinding into her roommate's hungrily sucking mouth.
"Oh, my thoughts and actions go a lot deeper than that. That's the tip of the iceberg," I managed to say with a nasty chuckle.
"Don't you mean the tip of the cock?" Jill parried and my cock throbbed in my hand. I writhed around a bit on my dildo, pushing it back deep into my ass and thought about how sexy Jill's body was. Then I chuckled.
"Yeah, good one! Look Jill, frankly, I'm not the nice guy you think. I'm probably the nastiest pervert you'll ever meet." This was met with loud, skeptical laughter.
"I'll never believe THAT," she replied and I knew we were into my fantasy for real. I told her I could convince her and her response was "No you can't." Of course I played "hard to get" and demurred but she insisted. "If you're going to claim to be a pervert and expect me to believe it, you better be willing to convince me," she demanded.
"Oh, I could," I replied. "Trust me."
"I do trust you, because you're so nice," she said. "That's why nothing you could tell me would shock me or convince me that you're a pervert." Again I insisted and she finally gave an exasperated sigh and demanded, "Then prove it! Put up or shut up, fat boy!" Oh man, she called me a name! Not a particularly filthy, sexy name, but I had to grip the head of my dick firmly to keep from going over the edge.
"Fine," I said with mock anger. "You want to know, I'll tell you." So I told Jill about my worship of asses, and how in college I'd been known for spending hours kissing and feeling and sucking asses of horny women. I also detailed my large collection of magazines and videos, and my at least twice a day habit of jacking off. I even mentioned some of the women I knew that I lusted for, and how I imagined watching them being fucked by big, fat cocks.Ê "Pretty perverted, huh?" Her response was exactly what I hoped.
"Yeah, right," she said with a hard, cynical edge to her voice. "Not a bit perverted. Like I said, you're no different than anyone else. Nice try."
"I'm not finished yet, Jill," I replied. Then I regaled her with my submissiveness to sexy asses, and how I loved having firm asses sitting on my face, cheeks spread wide and my tongue deep in the hot, steamy anus, sucking and licking and fingering the woman's pussy. I also mentioned how much I loved having women finger my ass, and with more than one finger.
.... There is more of this story ...