To understand this hook-up it’s important you hear about what came before. It was, as some would say, a “learning experience.” One of those things you *have* to go through—unless you get trapped in it, and never go through it but *stay in it*. Luckily, that didn’t happen.
I was in a relationship for two years after college with a guy who liked me—but only if I was in a certain position, and conforming to his idea of how I should behave. Example: He scolded me when my backpack was placed in the wrong compartment of his apartment and listened to make sure I wasn’t too loud in the kitchen/shower.
He was handsome, charming, successful, and fit every box: I thought if I could only make him happy, I’d never lose him. The urgency was compounded by what became a refrain in our relationship: Him telling me, “No one will ever love you like I do.” Like I was tragically flawed, and he could deal with me.
If your haunches are raising, then good—you’re more attuned to some of the controlling elements of this relationship than I was. For a while I just thought I was lucky to have him. I was 24 when I was strong enough to realize I was worthy of a different, more generous love, and I’d be better off on my own.
Getting to this revelation was far from easy. Looming over my head was what he told me: I was unlovable, unfuckable, etc. But a month after the break-up, when I turned 24, the *primary* thing I felt was free. We went to a bar in Brooklyn.
That’s where we met him. I’ll call him Alwyn, because his real name was similarly unusual, and made me give him a longer stare. He and his friend slid into the booth next to us—the classic bar intrusion. Normally I’d roll my eyes when things like this happened—especially in the middle of a good conversation—but that night, I was feeling open to my suddenly cracked-open world and all its possibilities. It didn’t hurt that they were funny, well-dressed, asked us questions about our lives. I was taken by Alwyn’s story of going on a recent vacation with only his mom. After that, I was definitely primed to like him.
Then came the turning point. He was sitting across from me, and initially had been flirting with my friend. *Whatever*, I thought. I kept doing my thing. I was in the middle of a spirited conversation, when I saw him watching me intently.
Alwyn started mouthing something at me, as I was talking. He didn’t say anything. The rest of the conversation moved, until I could make out the words.
*I like you*.
That’s what he was saying.
Now, for the past two years, my ex rarely said anything like that. He struggled to give compliments. When he asked me to move in with him, I said I would, if he could tell me some more nice things once in a while. He said he worked long hours—I needed to be more understanding.
Rationally, I understood this guy was a stranger in a bar. Him deciding he “liked” as the result of a surface interaction wasn’t, in itself, a miracle. But it was validating—a reminder that the “reality” that I’d been living in for the past two years wasn’t entirely real. I was likable. So likable that all it took was a few minutes for him to mouth that, unprompted. We hadn’t even touched. I’d later learn that he worked in finance, like my ex—actually, was much higher-ranking than my ex.
After that, I was smitten. I’m not sure if I’d “right swipe” on Alwyn if I saw him on a dating app, but I was drawn to him in person. He was smart and impeccably dressed. You could tell he smelled good just by looking at him. He had the spark of life in him, as I like to say, and that made him all the more attractive. Attraction TRULY can shift based on behavior, and I found him attractive.
They asked what the rest of our plans were. “We’re going to House of Yes,” I said. “But we need to get tickets.”
House of Yes is a free-for-all bonanza of good vibes in Brooklyn, down the street from the bar. Unfortunately, my friends and I didn’t have tickets. It was $20 a pop to get in. Alwyn and his friend made eye contact. “We’re in,” they said—and ended up paying for us to get in. I didn’t feel bad. Alwyn was a VP at an investment bank. A few hours later, when I ended up in his apartment, I realized spending $60 probably didn’t make much of a different.
Once we got on the dance floor, he flung me around with abandon and affection. We danced, as my friends went around with his friends. I vaguely remember him introducing me to people as his next girlfriend, hah. I wasn’t ready for that designation, but enjoyed the way his smile and affection seemed to spring freely, without me needing to beg for it. Alwyn was a good kisser. Deliberate. He didn’t overload on tongue, but wasn’t stiff, either. And he was a great *dancer*. We had a blast.
Seeing us together, my friends felt comfortable with me running off to his apartment. I let them track my Uber—you can never be too safe!—and we were off to the West Village (a wonderful neighborhood in Manhattan), to Alwyn’s one-bedroom apartment. On the cab ride home, he told me all about his life, words springing freely.
And I enjoyed the best view of Manhattan from the bridge: Seeing the skyline, knowing your destination would be a good fuck. He parted my legs in the cab as he spoke, and placed his hand on my inner thigh. Sometimes when the car stopped he moved his finger onto my panties, and under them. “I can’t wait to see you,” he said. “All of you.”
I wasn’t attracted to him because he was rich. But when I opened the door to that apartment, I wanted him to fuck me on every single lavish surface that populated his too-big apartment. The elegant couch in the living room, sprawled out before us. The sturdy wooden table that could probably seat 10. The sizable hallway connecting the bedroom and the living room.
And then the *bed itself*. You know how hotel beds have that crinkly comforter that you just want to get immediately dirty? He had one of those. Alwyn was gentle, but I knew what he wanted, because I wanted it too.
“Take your clothes off,” he said, dimming the lights. There was a gigantic mirror in front of his bed. I watched him watch me in the mirror as I shimmied out of my dress. He took off his pants and button-up shirt, full of glitter from House of Yes.
We intertwined, making out, and fell onto the bed completely naked. There is NOTHING like the feeling of a body pressing up against your body—so long as you both want to be there, of course. He was soft, and broader than me. I felt totally surrounded when he put his arms around me. I stopped kissing him to take another look. His skin was much darker than mine, and so I got foundation all over his nose as we made out.
“What?” He asked, laughing.
I shook my head. “This is fun.”
“How fun do you want it to get?” He ran his hands down the side of my torso, following my ample hips. I have small boobs, but he zeroed in on my extremely sensitive nipples, and began twisting. “How fun?”
I leaned over him so that I was kissing his neck, and then reached backwards to touch his cock. “More fun,” I said.
He twisted me over and put me on my back. Alwyn leaned over so that he was pressing against me entirely as he got his cock ready for me. He whispered in my ear. “This might be a lot at first,” he said. “I promise I’ll go slow.”
Oh, right. I forgot to mention. Alwyn had a massive monster cock. VERY thick. VERY long. Sort of like a forearm. I didn’t know how I was going to take it—and so I decided not to dwell until he was inside of me.
He knew how to handle his gift/curse, and was extremely well lubricated before he started pressing into me. I arched my back, and he nipped my ear, rubbed my nipple. “Relax,” he said. So I spread my legs and kissed him, only half paying attention to the pressure that was building around my pussy. Once he was finally in more, I could enjoy how good it felt to be that full. He started thrusting slowly. Alwyn made a funny noise when he fucked me—almost like a grunt. The faster he went, the more he made the noise. I enjoyed the idea that I turned him into some kind of animal.
Meanwhile, I was a total animal myself. My body’s responses were uncontrollable—I was being torn in two with pleasure. He wanted me to put my legs up so he could reach in deeper, plunging against my cervix. It hurt too much, though—sorry, Alwyn!
He regrouped, and grabbed my hips so that I was now kneeling across the length of the bed.
“I want you to look in the mirror,” he said. “Watch what I’m going to do to you.”
I turned my head to the left and saw him position his cock at my entrance. His hands were on my hips. He leaned over and kissed my back a few times, rubbing my pussy to make sure I was ready. “You’re so wet. You know that? You are dripping for this cock.”
I moaned, and arched into his hand as he made contact with my clit. “I can’t wait to see what you do when I put this cock into you.”
“Didn’t you already see it?” I ask.
“Not from this view,” he said, and before I could respond, his cock was plunging into my pussy. I was looking in the mirror, and saw my face fall open with pleasure. Alwyn was not interested in holding back from his angle. He grabbed my hair, and started thrusting. Our bodies looked so good together: My long pale legs, his dark skin. I’ll never forget it. Looking at us like we were a work of art.
He fucked me until he came in a series of…well, more of those groans.
“Are we not going again?”I asked, running my finger along his chest. I was mostly teasing. It was like, three in the morning and he was obviously spent.
“I’m 35,” he said, laughing. “I’m too old for that.”
I think I could’ve convinced him to go again, but I was tired too. He woke me up with a massive boner. I curled my body toward him wordlessly, and waited for him to enter me from behind. We had looong morning sex as the Sunday morning light drifted into the window. I watched him eat me out from the mirror.
Then Alwyn ordered us bagels and coffee, and we read each other the newspaper and talked for hours. He didn’t remember saying all of the things he told me in the cab—deep biographical details. He said he was shocked, a bit, by how much he opened up. But we felt comfortable with each other.
Nothing ever ended up happening ~romantically~ with Alwyn though I could tell he was interested in possibly pursuing something. I just wasn’t ready. He was also 11 years older than I was, which is fine, but I felt very *young*. I didn’t want to be trapped in another “uneven” relationship like the last one, and that might’ve happened. But maybe not!
Still, I’m grateful for the affection and kindness he showed me over the dates we had together. Especially think fondly of the summer day I hid away from the blazing heat in his apartment for hours, and we had a BLAST. Or the time, for post morning-sex treats, we went to an adorable tiny restaurant that’s since closed due to the pandemic.
After Alwyn, I broke the streak of men in finance. I often see my time with him, the first person I slept with after my ex, as a step toward closure.
Source: reddit.com/r/gonewildstories/comments/k33p2i/that_time_i_24f_was_seduced_by_a_rich_investment
This was actually a really beautiful story
this is such a beautiful, sweet, thoughtful story. thank you for writing this. I really know what that feeling in Brooklyn of being younger and going through things and feeling free and healing and growing feels like. Going to shows, house parties, etc. thank you.
This is a terrific story! Very genuine.
That was so wonderful written – thanks! <3