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Within the first ten minutes it was clear that Chava and I were incompatible. We sat across from each other in the bright lobby of the four seasons in Manhattan playing Jewish geography, somewhat bemused by the fact that it seemed like the only reason we’d been set up was because we were both ba'al teshuva’s – although me less than her. She had been married and recently divorced, still sporting a full shaitle that left everything to the imagination. I had recently abandoned a doomed 6-month relationship and was enjoying the newfound freedom of being a single, affluent bachelor in Crown Heights.

As luck would have it, I had noticed her in the gym several months prior – and she seemed to have recognized me from around town, so it wasn’t so much as a lack of attraction, but rather our morals at the time were hardly aligned. Nonetheless, having both lived a secular life before, we got on amicably – amicably enough that the shadchan recommended we take a second date, even though, by that time, I had figured out who her sister was and might have asked a few too many questions on that front.

So that’s how we found ourselves in a dimly lit corner seats on the roof of a Manhattan club, having both likely decided that we weren’t going to get married, she sported a long black skirt and floral blouse, her brown curly shaitle done up in a cute little ponytail that showed off what I learned was a beautiful jawline and neck. I arrived straight from work, with a loose tie, white shirt and slacks. To the outside observer we might have looked like work colleagues, or her my assistant.

We started by ordering drinks – but quickly shifted to tequila, my Thursday night preference, and despite our incompatibility, our curiosity got the better of us, as our shoulders soon began rubbing against eachother to the rhythm of the music. When she got up to pee, I walked with her, holding her hand, to the bar where I waited.

When she returned, she drunkenly wrapped her arms around me, leading me to the dancefloor where we danced in an embrace.

Closer and closer we got, our eyes connecting, oblivious to the world and the days to come. She turned, grinding her bum against my groin as I held her hips. My hands traced her underwear as my lips touched the small of her neck. She pressed into me and whispered “let’s get out of here.”

With few places to go, we hopped in a cab to Brooklyn and made our way to my apartment. The hope was that my roommate would be sleeping once we arrived, but as I turned the lock I could see he was still up in the living room. Quick thinking and we went to the roof where she embraced me again - her fabric seemed to cling to her curves like a second skin, and my eyes were drawn to the tantalizing glimpse of cleavage – she must have undid a button on the way home. Her eyes sparkled with mischief as she moved in time with the music of our heartbeats.

Our bodies pressed together, the heat between us palpable as we kissed fervently beneath the stars. My hands roamed freely over her body, tracing the contours of her waist and hips once again, this time with reckless abandon.

With each passing moment, our inhibitions melted away like ice in the desert sun. Her lips parted, inviting me to deepen our kiss as she ran her fingers through my hair. I responded by caressing her breasts, teasing her nipples until they stood erect beneath the thin fabric of her dress.

Our hands wandered further south, and soon, we found ourselves entwined on the roof, our bodies rocking against each other in perfect harmony as I unzipped her dress with trembling fingers, revealing a landscape of smooth skin and delicate curves. As we continued to explore one another, the sights and sounds of New York faded away, my hands cradled her subtle breasts as her bum pressed deep against my cock. In that moment I pushed deep – past her inhibitions, and lifted up her skirt, her bare bum against my pants she reached for my cock and turned, pushing me aside until my cock was deep in her throat. My hands reached for the back of her head as I began to face fuck her, looking down at her with abandon.

In that moment she looked up at me, her mouth around my cock, her shaitle slightly disheveled, her hands cupping her breasts, and, popping out my cock, she said “please fuck me.”

More about Chava and I to come if there is interest.