You would think that Bonnie getting pregnant on purpose thanks to me would have dissuaded me from my goal to bareback Alison. But you would be wrong.

The way I looked at it, Bonnie was some totally fucked up bitch who thought that just because I did her one time and she just happened to get pregnant, keeping in mind that she completely ignored her responsibility to use birth control, that I should somehow be responsible for her and her new baby. I mean seriously, what woman in her right mind would actually expect such a thing?

Alison on the other hand was virgin territory for me. Not that she was actually a virgin, because from what she had told me she'd had sex before, although I'm sure whatever sex she'd had would be nothing compared to me. No, what I mean is that Alison was a 'bareback virgin', in other words a woman who had never had a bare cock inside of her pussy, unencumbered by a condom. The conversation she and I had a couple of months ago still echoes through my mind:

 

"But don't you ever feel like giving into the heat of the moment? Feeling the friction of his bare skin against yours? Just saying to yourself, 'Fuck it, I don't care what happens, I just want to have sex with this guy?'" I asked Alison, looking at her with just a little bit of twinkle in my eye and the corner of my mouth upturned just the right amount so that she would think that I was kind-of sort-of kidding, but not really.

"Jason, are you serious!? Whenever I have sex I wear a diaphragm and make sure the guy has two condoms on, plus I'm always on the Pill," Alison smiled back at me, wrinkling her forehead and looking at me with her big blue eyes wide open in mock shock. She wanted me to know that she knew I was sort-of joking with her, though I'm pretty sure at least some of what she said - about the diaphragm and condoms and Pill - was absolutely true.

Immediately after she said those few words I knew right then and there that I was going to make it my personal mission to bareback her. My instinct and intuition told me that I would have to take things nice and slow with Alison if I had any hope at all of getting into her pants, and I was also pretty sure that I'd have one chance and one chance only. From the way her pale face flushed a nice crimson pink when I made my comment about 'friction and bare skin' I knew I'd planted the seed - no pun intended - and was off to a pretty good start with her."

 

Alison was my mixed doubles tennis partner at the racquet club that we both belonged to and was as WASPy as they come. Her family had lived in the City for generations and over the years had become involved in banking and finance. She had once mentioned to me in passing that she held a junior position at a bank in the suburbs that her father owned and had let me know in no uncertain terms that she was being groomed for bigger and better things. She was mid-thirties in age, just like myself, mid-height, nice athletic body with just the right amount of curves, and had the blond hair to match her alabaster skin and blue eyes. She had gone to the right schools, was involved with the right charities, and also lacked the street smarts that one would expect a woman who had been raised in a protective White Anglo-Saxon Protestant environment to not have. Instinctively I sensed that this naivety was going to be the way I'd work myself into her mind, her heart and eventually that hot little place between her legs.

A couple of hours ago Alison had been absolutely ecstatic when we had won the mixed doubles championship with a third set tie breaker. After the awards ceremony we had retired with the rest of the club tennis players to the lounge for celebratory drinks. Now it was just Alison and I sitting alone out on the patio that overlooked the main center tennis court. The fire pit next to us burned warm, taking the chill out of the nippy spring air and adding to the warmth that we were both feeling from the first bottle of red wine.

I uncorked the second bottle that our waitress had brought and poured another glass for Alison when she asked, "You're not trying to get me drunk, are you Jason?"

"What, me? Why, do I have to?" I smiled back at her tease. "Seriously, I'm enjoying your company way too much, there's no way I want you to fall asleep on me."

A look that I couldn't quite place flashed across Alison's eyes. Her pale face glowed with a flush from the wine we'd been drinking, and I remembered that your body absorbs alcohol quicker than usual after a workout. In truth I did not want Alison to get too drunk tonight so I decided to help her pace herself. We sat together for a moment without saying a word, enjoying the presence of each other's company until Alison broke the silence.

"So what ever happened with you and Bonnie? I haven't seen her around the club, except for the one night that I ran into the two of you in the parking lot."

I almost choked on my wine when Alison asked that question, and a feeling of dread and horror swept through my body. That would be the night that she caught Bonnie and I kissing, caught me fondling Bonnie's erect nipple through her silk blouse, squeezing her nipple so hard that she gasped in pain and pleasure as we kissed. Could she possibly know about Bonnie getting pregnant on purpose? Had the two women been talking about me behind my back? Were my months of scheming to finally get to where I'd be able to bareback Alison going to be totally wasted? These thoughts and more raced through my mind as I avoided Alison's stare as long as humanly possible.