SPH First Date: His First Time Getting Laughed At

I met him at trivia night, which is not my usual hunting ground, but he was on the other team, and he kept getting the answers right, and smart is my weakness. We got to talking after, and he was sweet and funny and clearly nervous around me, which I found adorable. We exchanged numbers, we texted for a week, and somewhere around day five, deep in a conversation that had started about movies and wandered somewhere much more interesting, he confessed something. He had never done it. The thing. He had thought about it for years, fantasized about it, but he had never actually asked anyone, never tried it, never been laughed at, not once.

I stared at my phone for a full minute, grinning like an idiot, because I had just been handed something precious. A grown man, handing me his unopened curiosity, trusting me with it. I am a brat, but I know a gift when I see one, and I told him we were absolutely going to fix that, and that he had picked exactly the right girl for his education.

I had had plenty of first dates, but never an sph first date, and I wanted this one to be perfect for him. So I planned it. I told him to come over on Saturday, to dress warm, to trust me. When he arrived, I led him up to my rooftop, where I had spread out a blanket and hung string lights, the whole city glowing around us. He looked around, stunned, and I told him a first time like his deserved a setting, not a couch. He laughed, nervous, and I could see his hands shaking a little, and I took one of them and told him to breathe, that I was going to take very good care of him.

We sat on the blanket, close, and I started slow, because a first-timer needs a guide, not a hurricane. I asked him what he had imagined, all those years, and he told me, halting and blushing in the string lights, describing these fantasies he had clearly replayed a thousand times. I listened, and I smiled, and then I told him reality was going to be better, because I was better at this than his imagination. He groaned, and I had not even touched him yet, and I knew this was going to be wonderful.

I told him to lie back, and he did, stretching out on the blanket under the open sky, and I knelt beside him, and I unbuttoned his jeans, slow, giving him every chance to stop me. He did not stop me. He watched me with wide eyes, breathing fast, and when I finally got a look at him, I started laughing, soft and delighted, because he was tiny, perfectly, hilariously tiny, and his face, the look on his face when he heard me laugh for the first time, was pure revelation. His eyes went wide, his mouth fell open, and then this shudder ran through his whole body, like every fantasy he had ever had had just come true at once.

I was gentle with him, at first. I teased him softly, laughing like it was a secret between us, telling him how cute he was, how I could not believe no one had ever laughed at this before, what a waste of years. I ran one finger down his chest and told him he was doing perfectly, that his only job was to lie there and feel it. He was trembling, overwhelmed, and I could see him fighting it, fighting how good it felt to finally get the thing he had wanted for so long.

Then I turned up the heat, because I am a brat and I cannot help myself. I got bolder, louder, laughing right in his face, describing exactly what I saw, telling him the string lights were bigger than he was, telling him the city below us had no idea what was happening on this rooftop. He was gasping, clutching at the blanket, begging me not to stop, begging in this raw unpracticed way that told me he had never begged for anything in his life, and it was the hottest thing I had ever heard.

I took him in my hand, and he was so hard, this tiny straining thing, and I laughed, and he bucked, and I kept laughing, and he came with a cry that echoed off the rooftop walls, all over his own stomach, shaking under the string lights like he had been struck by lightning. We lay there after, side by side on the blanket, looking up at the sky, and he was quiet for a long time, and then he started laughing too, this dazed happy laugh, and he told me that was the single best experience of his life. I told him I knew, because I had planned it that way.

He asked if every first date with me ends with someone getting laughed at on a rooftop. I said only the ones that earn a second date. He asked if he had earned one. I smiled at the city lights, and I did not answer, because some questions deserve to hang in the air a little. He is still waiting for my text. I am still deciding how long to make him wait. And honestly, watching him squirm might be my favorite part of the whole night.