The following is a true story - chats are open

If I can be frank, sex with Chava on the roof that first night wasn't great. It's the anticipation that was memorable. The long and short of it is that I lifted up her skirt and she pulled her black lace panties to the side. Her labia lips were glistening in the summer heat, and as I lined my bare cock up to slide in, her hands carefully parted her lips, letting me slide in with ease. We had sex missionary, right there on the roof, her legs wrapped around me, forcing me deeper. Like new lovers, I was hardly comfortable enough to really display my kinks. It was a passionate affair, but nothing that pushed me over. When I was ready to cum, I pulled out of her now creamy vagina and finished on her pussy in the final seconds. Almost immediately, I could sense the tone of our relationship souring - we got dressed, and as I led her out the door, she left with only the softest kiss on my cheek.

We didn't end it per se, in our own way we told the shadchan that we could take things from there, but over the next few days leading into shabbos we hardly texted, perhaps it was the hangover, but more likely it was her regret. Fortunately, the shock of the moment passed by motzi shabbos, and I received an inquiring text late at night inviting me to "talk" the next night.

That next night, I borrowed a friend's car and offered that we take a drive to Riverside Park for a walk. The drive was a mixture of playful banter and awkward energy. As we parked on 82nd street and got out I was keenly aware of her distance. We had touched only days before, but now her arms hugged her chest protectively. We entered the park and found a secluded bench - a good sign, I figured as she took off her purse and crossed her legs. I noticed that she was wearing a white button-down, which when seated, from the right angle, one could spot the contours of her breast which were protected by what I would come to learn was a beige lace bra (if I had stared harder, I would have been able to see her light areolas and quickly hardening nipples).

"Talk" I said playfully as we sat staring out at the river.

"So..." Chava said. I've been thinking about the other night. Don't get me wrong; I really liked it, but I don't think we should do it again."

"No problem!" I said. We can be friends. We have a shared background. I hope you didn't beat yourself up about the other night."

"No no, I didn't" Chava said. "I just don't think we're compatible in terms of marriage, and I didn't want you to get the wrong idea."

"Listen," I said. I don't think we'd work together either. You're cute, obviously, but I am hardly at your level, and I think I'd bring you down."

"I agree," she said. "I appreciate you understanding..."

A silence ensued.

"But..." I said. "the other night was great...I am certainly not against doing something like that again."

She laughed and I felt the warmth of her arm against mine.

"Me either" she said, as she turned to face me.

In that moment our eyes locked - the primacy of the moment flared as I saw her lips quiver. I felt the heat building between us as we inched closer. My lips met hers and her hand went eagerly to the back of my head, pushing me deeper as I tasted her soft tongue.

In the darkness of the park, the heat between us was undeniable as we continued to kiss, our bodies pressed tightly together. Her hands began to roam freely over my body, tracing the contours of my muscles and sending shivers down my spine. I could feel her hard nipples pressing against me, and I knew that she was just as eager for more, as I was.

As we broke apart from our passionate embrace, Chava's eyes locked onto mine, filled with a mixture of desire and fear. "We shouldn't do this," she whispered, her voice trembling with lust. But I could see the temptation in her eyes, the struggle between her reservations and her deepest desires.

I took advantage of that momentary weakness to claim her lips again, my tongue probing deep into her mouth as our bodies strained against each other. Her moans grew louder, more urgent, as she clutched at my back, urging me closer.

Finally, I pulled away from her, gasping for air as I looked down at her flushed face. "You want this," I whispered, my voice low and husky with desire. "Admit it."

Chava's eyes flashed with defiance, but the fire in them betrayed her true feelings. "Maybe I do," she whispered back, her voice barely audible over the pounding of our hearts.

With that, I knew that we were both lost. There was no going back now. Our desires had taken over, and we would follow them wherever they led us.

As we continued to make out on the bench, my hand slid down Chava's stomach, tracing the curve of her waist before dipping lower, into the softness of her skirt. I could feel the heat emanating from her sex, and I knew that she was more than ready for me.

With a quick flick of my fingers, I popped open the button on her jean skirt and sliding them down her legs, exposing the glistening folds of her pussy to the cool night air. Chava's eyes widened in shock, but she didn't pull away as I leaned in closer, my breath hot against her sensitive flesh.

"Is this what you want?" I whispered, my lips brushing against her clit as I spoke.

Chava's eyes rolled back in pleasure as I began to lick and suck at her pussy, my tongue darting in and out of her folds like a snake. Her moans grew louder, more urgent, as she clutched at my hair, urging me on.

My tongue on her clit, I reached up to play with her barely contained nipples, first stroking, then pinching it. Her moans encouraged me further I began to pinch harder and pull. She pushed against me, encouraging me to pull harder. I twisted, eliciting an audible moan that reverberated around us.

"You like rough?" I whispered in her ear.

"Yes, please" She responded.

"Yes please daddy" I clarified.

"Yes, daddy" she moaned.

With that, I knew that I had something special...

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To be continued.