Y*ou may want to start with* [*part one*](https://www.reddit.com/r/gonewildstories/comments/hztkfd/fm_the_time_i_26f_discovered_the_best_place_to/) *of this story, which began at a bar and finished at a rooftop in Brooklyn. At this point, Hugh has just finished fingering me (very well, I might add) on top of his brownstone building, overlooking a main avenue in Brooklyn. He said that he wanted to fuck me in his one-bedroom apartment, and who was I to say no?*
***
Immediately, I could tell that Hugh and I were well matched. As in, he and I were both *freaky*. After our seamless foray into public sex, I felt like I could be honest with him in ways that I couldn’t be with my most recent ex, who got a bit testy whenever I let on the true boundlessness of my desires. For example, when he discovered that I’d had a few one-night stands before we got together (not that many, y’all), he got so angry at me he couldn’t speak. “I didn’t know you were that kind of girl,” he said, ruining our entire weekend getaway. And every time I joked about having a threesome, he made sure that it remained just that—a joke. Hugh and I, on the other hand, were already planning our first visit to a sex club, and we’d only just met!
Essentially, before Hugh, there wasn’t that much rooftop fingering in my life—only a lot of fantasizing during missionary (nothing wrong with missionary, though). He led me back down the steep ladder and into his apartment, which was a series of beige rooms.
“Sorry about the boxes,” he said, gesturing around at his items, half-unpacked. “I’m going to clean up for a sec. Make yourself at home.”
He’d just moved from across the country, and his life was in a bit of disarray. Still, his apartment wasn’t messy, so much as it wasn’t quite lived-in. There was a bike on the wall. A half-drunk glass of water on the counter. You know that intimacy that comes when you’re walking around someone’s apartment, studying their things, and piecing together an image of him? I was trying to learn who he was. A biker. A tech guy who didn’t own any posters. Really good at fingering. Fine, it wasn’t as thorough as a MBTI exam, maybe, but I was trying.
After a minute or two, he walked out of the room and leaned in the doorway, tucking his hair over his ear. “Come on in. There’s air conditioning in here.”
“Oh, thank God,” I said, getting up from the chair, where I’d been gradually melting. The living room was *hot*. He was, too, but in the way I preferred. The room still lit in a bright, dorm room white. I walked in and immediately felt his hand snake around my waist, pulling me closer.
“I went as fast as I could,” he said, kissing my neck. “I wanted you in here.”
“Can you turn off the lights?” I asked not because I was insecure, but because I was distracted by all of his stuff strewn about on every possible surface. Star Wars figurines two rows deep. Books in piles. If he didn’t turn off the lights, I’d either start rearranging things myself, or studying his bookshelf. Instead of questioning me, he turned them off.
As he found the switch, I walked to the bed and spread my legs. “Oh, so you want me?” He said, turning around and beholding the sight before him. Me, propped up on my arms. Legs wide. Smiling with my head tilted.
“Come back,’” I whined.
“Ask more nicely,” he said, standing with his arms folded, assessing me.
I took my finger and pushed my undies to the side. “Don’t you miss this view?” I asked, knowing my pussy was still visible in the soft glow of the room. He fell onto the bed and pushed me down farther, grinding against my bare legs with his jeans. We kissed as he fumbled with his button.
“Lemme do it,” I said, reaching down. It’s one of my favorite things, taking off a man’s pants. He rolled onto his back and let me unbutton, and roll his jeans down gradually. “Get back up here,” he said, as he kicked the rest off. Then I sat on his boxers, my undies still on, and he raised my dress over my head. He unstrapped my bra in a seamless movement.
“So much better,” he said. “God, we should’ve fucked up there.”
“That would’ve been asking for it,” I said. He was back to sucking on my nipples.
“Let’s see if you still have energy later. Maybe we’ll go up at three in the morning. I’ll lay you down flat on the roof and fuck you. No one will be able to see.” I could feel his cock growing as he described what he wanted to do to me next, after he was done with this.
“If you don’t fuck me now, there’s a good chance I’ll never make it to the next hour,” I said. “I’m one big throb at this point.”
“Lemme check,” he said, reaching down and pushing my panties aside. His fingers plunged back inside me briefly, as if they were taking an assessment. “Oh, baby. You are *wet*. You’re ready for this cock, aren’t you?”
I nodded. I begged. And what did he do? The man *smirked*.
“You *think* you’re ready for it. Take a look at this cock, baby, then tell me,” he said. I got off his lap and let him push his boxers down, exposing what he’d been hiding this entire time. Reader, I couldn’t believe it.
It was a monstrous dick. I mean, a *gorgeous* dick. But more like another limb than a cock. He laughed as I looked at it with barely disguised shock. I was tempted to measure its width against my forearm, but didn’t want to make him feel like a specimen in a lab. Plus, I didn’t want to *see* his cock anymore. I wanted to feel what it would be like inside me, pushing the walls of my pussy farther than they’d ever been challenged.
“You’re huge,” I said.
“So I’ve heard. Want to go on top, so you can go slow? It’ll be easier like that.”
I appreciated that he said that, because sometimes big dicks *hurt*! At least they hurt my pussy—I’m not sure why, but I’m sensitive. He ran his fingers around my slit. “Let’s get you real wet. Keep doing that as I put on a condom.” He pulled out a pack—Magnum, naturally. The image of his big cock being stuffed into the condom was oddly hypnotic. The way it sprung upwards, after it was done.
I grabbed his hand and brought it back to me. “Am I wet enough?” I asked.
“Let’s see.” As he rubbed my clit, I ground on top of him and kissed his lips with a few soft pecks. Then I reached behind and positioned his cock right at my entrance. “I think you’re ready,” he said, and I reached back to hold his cock in place. I started to lower myself onto the thick head. Already, I felt my pussy become quenched on his girthy, veiny cock, like I’d been thirsty and now had so much water that I was overflowing. Immediately, I started to moan, and lifted back up.
“Go slow,” he said. “It’s all right.”
I put more weight on my hands so that I could leave my pelvis with more control. Gradually, I moved p up and down, taking another inch with each thrust. “Oh, yeah. You feel so good, baby,” he said, encouraging me. “I love watching your pussy swallowing my cock. Look at that. Look at how stretched you are.” He started to moan, too.
Once he was all the way in, I could relax. I did it. I could take him. Moving my hips in circles, I stayed like that for a while, completely filled up. Then I leaned forward and said two words: “Fuck me.” Lifting my hips up, I waited for him to start thrusting upward, furiously—my favorite position. He got the signal.
“Are you sure you can take this?” he asked.
“There’s only one way to find out.”
Off he went, his hands clawing into my back for support, his cock ramming upwards. There was no helping my screams, which came furiously. It was a biological response to a massive, nine-inch cock tearing my pussy apart and making me slobber. What was I supposed to do? Just accept it quietly? No way.
I leaned down so I could muffle myself on his neck. “Oh my god oh my god oh my god,” I said. “You’re tearing open.”
He kept going, lost in a trance. Eventually I started moving my hips to meet him, and we were in a rhythm. Finally, I heard his breathing grow more ragged, until he slowed down. “I almost came,” he confessed. “But I want more of you before that happens.”
“How do you want me?” I asked, like I was a dinner that was being prepared. Which, in a way, I guess I was.
“With your legs in the air. Torn in two.”
Jesus. This man. I rolled over and waited for him. Now that I was all stretched out, he didn’t hesitate to plunge into me quickly. Still, it was a shock. My eyes bulged at the feeling, and I wondered how porn stars could handle this for so many hours of a day. It had only been a few minutes and I already felt like I was at my limit.
As promised, he lifted my legs onto his shoulders, and started to push into me. Now, at this position, his cock could reach even farther into my pussy, to the point where it was painful. But knowing that my momentary pain was giving him pleasure was a surprising turn-on. For as long as I could handle it, I left him pound me, biting onto my finger when the feeling became too intense. Eventually, he went too fast and I had to put my hand on his chest.
“I can’t handle it anymore,” I said. He nodded, sweaty and towering above me.
“That’s fine. I want to look at your ass while I come. I haven’t had that view yet.”
He flipped me over. This time, he went in slowly, playing with my nipples. He stopped midday through. “Is that…you’re not completely inside me, are you?”
“No,” he said, pausing. “I want you to beg for more.”
“Oh, come on.”
Then he pulled out completely, and I was left empty. “I’m serious,” he said. “It turns me on.”
He *was* serious. I spread my legs farther, wiggled my ass. Turned around and looked him in the eyes. “If you don’t ram your massive cock inside me right now, I’m going to melt into the bed and there’s going to be nothing left for you to fuck.”
“That’s it,” he said, beaming. “Keep talking to me.” Still, he went in slow, frustratingly slow.
“Please, Hugh, please keep going. Please, I need your whole big cock. All the way in. I want you to go farther than any cock has ever gone before.” As I spoke, I sunk down further, like my knees were giving out. Every time I felt him inside me was a surprise. Once he finally fit again, I moaned.
“Oh my God,” I said.
“Now I’m in,” he said, and was off to the races. He grabbed my hips and started thrusting methodically, telling me he loved the way my ass jiggled, loved the way my hair looked. Sooner than I expected, I heard his breath get raggedy.
“Are you gonna come for me?”
He croaked out a yes. Breathy. Soft. He kept going, kept going, until he pulled out and shuddered, coming into the condom. I turned around in time to catch the last convulsions, his face surprised and relieved.
I sprawled on his bed, exhausted, and waited for him to join me. For a while, we cuddled and let our sweat get cold under his AC. We spoke about our fantasies—and for a recent hookup, we both were devastatingly honest with each other. He even ended up revealing that he had a thing for watching incest porn between stepfathers and daughters (which I know is very popular). It was interesting to hear someone be very honest about this; I know he’s not the only one. I was able to ask him what he found appealing about it. I vaguely remember he may have revealed his *own* thoughts on incest but I’m going to be honest…I don’t remember completely.
Anyway, we didn’t end up meeting again because I moved back home the next week for a few months, as I found a new apartment. The timing didn’t work. I did get a few sexy texts from him, though. Maybe after all this is over, we’ll meet again, and my Brooklyn life will be back!
Source: reddit.com/r/gonewildstories/comments/i1k7cz/fm_i_learned_the_best_place_to_get_fingered_is_on