Steven Takes a Chance

The blindfold was taken off. There seemed to be a lot of people around, but I could not make them out. I squinted into the glare even as I felt my cock grow harder...What was that...traffic. It was the sun streaming through my window boring down into my eyes. I stretched amazed at how hard I still got thinking of the time that Kate told me that she wanted to use a strap-on on me, to fuck me with her cock.

I pretended to be taken aback at the time and said nothing. I shrugged it off, but could not shake the thought of her taking complete charge, using me that way. She could be a little bitchy so maybe I should have seen it coming, but after she said it out loud the mental picture of a hard plastic cock strapped around her little waist, sticking straight out from under her sizable chest would repeat itself over and over.

By the time that I got up the courage to drop subtle hints of interest, to offer to let her fuck me if she would do something else for me, she had changed her mind. She told me that she was not really sure about it after all and that she would not be able to be with guy who would let her fuck him with a strap-on, because she would not respect them enough. Oddly, that did not keep the idea from coming back into my head. I started imagining what kind of dildo she would pick out. How she would look with it strapped onto her petite frame, nestled tight against the short, perfectly groomed dark hair between her legs. She knew what control she had over me, that I loved to taste her and lick her. Often she would have me satisfy her and then idly rub my crazy hard cock as she dozed off leaving me almost desperate. Somehow that just drove to want to taste her more. That she could play the demanding mistress who thrived on building desire and teasing while pretending not to notice could never be in doubt. Somehow this coupled with her interest but condescending attitude towards taking a guy actually heightened my fantasies. Ultimately, it did not work out and I chickened out, in part because of all the people we knew in common and, in part, because I did not believe she had the maturity to possess me that way without abusing that power. In all honesty, however, that potential for abuse and humiliation that would result from my total subjugation to her whim and caprice still aroused me.

I recently revealed this desire to someone with results even I could not have dreamed or foreseen. I had started talking on the net with a woman who was very self-possessed, but seemed very down to earth and drew me in immediately. I could not believe what I was willing to reveal to her, but it seemed very natural. I did leave out that I had masturbated to the thought of Kate putting on a strap on and stroking it while making him tell her that I would do anything to get her off, even let her fuck me with her cock and then feeling her get off while fucking him with her strap-on.

Jennifer was so easy to talk to, whether joking or exploring various fantasies, role-playing or anything else. I did not hide the fact that I loved to please and even suggested that I would not mind relinquishing control if that would arousing her. She seemed to like that idea and often would push to see where my limits were each time we spoke pushing me a little further beyond my original comfort zone.

It started out simply. Jennifer agreed that she would like to have me please her and beg to taste her, caress her slowly, move my lips over every part of her body and then pull away flaunting his desire and her control (which was far more intoxicating for her knowing that she was also about to give into the my desire to feel my tongue glide across her breasts, my warm breath over her stomach as my weight shifted lower, feeling her legs move apart almost on their own allowing my lips to caress hers. My tongue slowly moving between her legs almost desperate in its intensity yet gentle. I knew that she would be able to feel the excitement, the tension in my tongue, as it glided across her lips knowing that I was incredibly aroused simply by the taste and smell of her and knowing that I would continue to tease her until the feeling spread up her lower back through her entire body, arching her back, pushing her head hard against the pillows at the head of the bed, wrapping her hands into my hair even as she felt my hands all over her body amazed by the sensation feeling as if it were my hands everywhere at once covering her. Their warmth matching the tension that was building in her body - and then all at once pulling away - seeing my look of desire and her own wonder of her restraint knowing that when she let herself go it would be that much more intense - she almost touched herself and then allowed herself even as she pushed me onto my back and moved to straddle my chest....

She bent over and asked me what I wanted even as I felt her fingers between her legs, feeling her index finger glide along my chest and then between her lips, into her, pushing into the soft warm skin, sliding so easily with the wetness already there. I would whisper back that I wanted nothing, but needed to taste her, to feel her explode against my face. She leaned back sliding a second finger into herself, gasping quickly as a look of quiet contentment spread over her face. "What would you do get what you claim you need?" she teased.

I opened my mouth, but before I could say anything she pulled her hand from herself and rested her fingers on my lips allowed her scent and taste to silence me. Even as I felt my mouth move to close over her glazed fingers, her tone changed, "I don't want to hear that you would do anything I wanted. Be more creative than that. I want you to think - to impress me - tell me what I want, and I will give you what you need." I was ready to play this game as we had before, but imagining the scene actually unfold, I still hesitated to say the words; feeling myself grow red and grow even harder as I punched in the words, "I would get you a strap-on and suck your cock if you wanted!"

"What? Say that again," she murmured. He could her feigned shock, playing innocent to exacerbate his embarrassment.

"I would suck your cock, mistress." "LOL." The sole reply leaving to think of her standing over him stroking her hard cock, watching him watch her hand.

"You want me to have a cock, do you?" she said sweetly.

"Yes", was the inevitable reply, "I do."

"And what would YOU have me do with my cock," she queried.

"I," my chest tightened as I felt myself giving into Jennifer and the game, "I would love to see you stroke it; that would turn me on." She never let me off so easily.

"What else would You like," she persisted.

"I would let you fuck me with it."

"With what?"

"Your cock."

"My cock? I like that. Where my pet?" I know what she wants, and I know it will happen now.

"In my ass. I would let me fuck you in my ass with your hard cock!"

"LOL" and silence. I feel the discomfort of a blank screen after such an admission. "Better - but not good enough. What else do you want. I know what turns me on. I want you to do what I asked and tell me what you want."

I cannot respond.

"Do you expect me to believe that you would do all this just for me."

"Yes. mistress, I would."

"Really," the sarcasm in her tone is apparent even then, "and the thought does not turn you on?"

I feel myself stammering "Yes" as my fingers type the word.

"Yes what? You better tell the truth this time. I want to hear what you have been thinking about you little slut." I bow my head and only see how hard I have gotten her persistence.

"I...I would like...It would turn me on to suck your cock. I have thought about you fucking me with your hard cock. It gets me very hard thinking about you using me like that."

"LOL", the inescapable tingle down my back and legs makes me shiver as I actually hear her giggle and little peal of laughter, enjoyment mixed with the power of condescension. "Really? You want to be my little cocksucker, my little bitch."

Another shudder, an involuntary gasp as I felt the blood rush down making me harder that I thought possible. On the other end, Jennifer lets her fingers move. The thought of Steven giving himself to her, kneeling in front of her, admitting to wanting to suck and be fucked by her cock. She moved her fingers faster and harder against herself bringing on little waves and finally pushing her over the edge as she realized that this could be real that perhaps he really did want to be used for her.

We continued to write to each and continued to get more risque and obscene. Jennifer told me how the thought of me sucking another guy, a real cock, for her really excited her. I told her that I think about it, knowing that she was pushing into an area only my deepest thoughts had entered. No sooner than I was willing to admit that, she went further.

She wanted me fucked. Then dressed up first alone and then in front of her friends. I played along, not fully realizing that as the stories became more extreme the initially bizarre, crazy scenarios were becoming realistic in my acceptance level. She pushed me to be more creative with the fantasies until I had been shaved and dressed before her friends only to be presented with a real cock and forced to beg to suck it as his friends were brought into the room; been made to beg for that cock on threat of being stripped of my wig in front of my ex-girlfriend; and then after begging being informed that instead of sucking the cock I was to let that guy fuck me in front of the group; and then being taken out with just Jennifer and my ex - and being forced to admit that the idea of sucking cock turned me on so much that I would suck more than one off if they let me suck one. Having me start to suck but have it pulled away as my lips barely grazed the hard head only to make me take one from behind and suck another off as Jennifer and my ex watched until the two men had cum on my face when Jennifer pulled the wig off anyway simply because she could, even if only to make my humiliation complete.

The fantasies became more intricate. I was a professor that had been compromised by a woman who then claimed to be transfer student from another college only after having numerous conversations in which I admitted to submissive fantasies. She then forced me to pleasure her in her dorm where I could be caught or be exposed. Having me blindfolded begging to lick her while she videotaped me in her dorm allowed her to take absolute control of my life. Including dressing up and bringing me to a fraternity for a hazing ritual in which I become the centerpiece for a circle jerk.

Despite the extremity of some of our scenarios, I always felt that there was a connection and the desire to please had moved beyond the mere fantasy. I really wanted to talk to her for real, to hear her real voice and interests. I started dropping hints - even clues to my phone number. I tried to actually buy into the role play and even bought a dildo, my first ever, and agreed to masturbate and cum on my face; all to please her to give her, if nothing else, some amusement.

I did not really believe that this would turn her on, but did hope to at least amuse her and continue the exploration.

Jennifer was pushing her envelope too. I did not know it at the time, but she was actually getting turned on by thinking of me, not just licking her, but also the situation we discussed and contemplations of the bitchier more extreme aspects were starting to grow on her. I never thought, and still do not, that she wanted to hurt me and often wondered if she actually might prefer if the tables were turned and I was the one in control. I think that she would enjoy, or could enjoy, that equally. Jennifer was not even sure at the time that she really wanted to have such control, but even so, every once in a while a wilder thought crept into her mind as to what would happen if she really had such control to let all of her strictures done even while stripping mine away.

She originally was not sure that the roles they played were really her, but over time she began to except this position of power and the thought of exercising it in actuality, not just over the net, began to distract her, to excite her.

One day Jennifer did it. She took my clues and dialed the number I had given her over a period of a few discussions. It was early evening, and I was in my bedroom reading when the telephone rang. I answered and said, "Hello," but all I heard was a click.

Normally, I just shrug such a thing off as a wrong number and ignore it. I felt some sort of a tingle that time though, so I dialed *69. A metallic voice listed off a number with a zip code I did not know. Even as I wrote it down, I wondered if it might really be Jennifer. My heart began pounding. Flight or fight. Or maybe something else, but assuredly the adrenal came on. I tried being rational and called the operator at least trying to find out what State the call had come in from, Washington.

I cradled the phone and paced back and forth across the room. I started to dial at least three times before I stopped unsure what would make sense. Ultimately, I decided this was an opportunity that I had thought about for months and there was at least friendship to be had. Nevertheless, I felt incredibly awkward as I dialed the number. My life had been pretty bland, and I did not think that the risk would be that great. Still it was a huge exposure, maybe, I called back - inevitably.