Quick intro note: I’m a handsome, vaguely articulate, well-educated, married and generally successful 39 year-old, pervert. I have a long history of dirtiness, and there’s something about the year and a half of basic confinement that has had me reminiscing about my past and some of my hottest experiences. I’ve decided I’m going to start chronicling them here, to keep them from disappearing altogether. Let me know if they’re enjoyable and feel free to say hello. I like penpals.
———————————————————————————————————————————————-
Caroline and I met, very briefly, smoking a cigarette outside of a bar on Bleecker Street. She was on her way out, I was on my way in, and she asked for a cigarette. She was tall, blonde, and truly beautiful, in a way that was immediately intimidating. I’d imagine that she could count on a single hand the number of times she hadn’t been the prettiest person in any given room. You might expect a person like that to be entitled, bitchy, and cold. And in this case, you’d be right.
I stood with her smoking and tried to make small talk, which she showed as little interest in as a person can reasonably express without just walking away. She gave answers that were only a word or two, and fucked around on her phone while we spoke. At some point in all of that, I asked her what she does. Without looking up, and in a tone that somebody might disinterestedly comment on the weather — she told me she’s a sex worker who humiliates men for money.
I responded with something like “oh cool, i get paid to let people humiliate me. But that’s just because I work for miserable people who treat people poorly and then get a paycheck.” I wasn’t wild about my job back then.Caroline looked up at me, and honestly, I think, noticed me for the first time. She rooted around in her purse for a second and handed me a card. “You can call me if you want.” I played it cool and waited 30 minutes to call her.She asked me to meet her in a weird little park that runs alongside the East River, way past Stuy Town. I was 95% certain she was just a very mean person who was sending me to Manhattan’s most inconvenient spot to stand me up, but she was sexy enough that a 5% chance was more than enough. Along the way I grabbed a couple of cheap bottles of red wine, plastic cups, and more cigarettes.
The park was basically empty aside from Caroline. I don’t remember the time of year, but I remember it was pretty chilly, but warm enough that Caroline was wearing a short skirt and I wasn’t wearing a jacket. She was sitting on a bench and didn’t so much as look up when I sat next to her. Her silence was disorienting, and my unreciprocated “hi” just sort of hung there, feeling a bit more pathetic with every second of silence. I sat down next to her and decided to play along. We sat in silence for what must have been 15 minutes. We watched a few joggers run by, boats out on the river pass. We probably looked like a couple who was breaking up, at that point when everything’s been said, but neither can actually walk away.
When she finally spoke, she launched into a spiel that — to be fully honest — she’d clearly been rehearsing in her head during our silent spell. I don’t remember it all. The gist was that she had no interest in being charmed, and no real interest in me. That her life was full of men whose needs came first, that being a domme meant, often, play-acting a man’s fantasy of what a dominant woman might want, but almost never getting what she actually wanted. I asked her what she wanted. She told me she wanted to be fucked well. I told her I could do that. She told me she wasn’t convinced.
There was more silence, then a lot of questions. She asked how big my cock was, if I could come multiple times without a break, how long I typically lasted. She asked if I made women come and how I knew they were actually coming. And then she asked me to stand up in front of her. I did as asked.”I want to see your dick. Take it out.” Glancing around, nervous, it seemed like we were alone. I was fully hard and realized I had been basically since the moment she started paying attention to me. I unzipped my pants and my cock sprung free. All she said was “Not bad.” Then she got up and started walking south, and motioned with her head slightly and said “You can come with me.”
I put my cock away, zipping up as I followed. She walked with purpose, quickly, and every time I caught up, she’d quicken her pace to stay a step or two ahead of me. I caught on and stayed behind her, following. We ended up in front of a nondescript building between 2nd and 3rd somewhere in the 20s. She unlocked the door and held it open for me, and I followed her up a tightly winding set of concrete steps to the roof. It was only a 2 or 3 story building, and the roof top sat well below buildings on all sides. There were lights on in dozens of windows.
Caroline pulled me to her, standing in the middle of the roof. It felt like we were on display for half of Manhattan. She leaned in and kissed me, our tongues finding each other, her perfect body pressing against me. I remember feeling the power dynamic acutely, the way she’d upended my night, asked me to follow her across Manhattan, and how I had, without the slightest hesitation. I remember knowing without it being stated that she came first, that I was there for her pleasure and nothing more, and that the pleasure I might get out of this encounter would be solely incidental. But most of all, I remember the first few moments of physical tough evolving immediately into an obsession. It was her taste, her smell, that she needed something so badly that I could give her.
She pushed me onto my knees and told me to take off her panties and hand them to her. I reached up her skirt, and slid them down. They were black, lace. I held them up for her and she took them and balled them in her fist. She hiked up her skirt, pulling it above her waste, exposing herself to me — and anybody who happened to be looking out their window. She was tall, and on my knees I had to crane my neck slightly to reach her pussy. I cupped her ass in my hands to give myself more leverage, and began licking her perfect pussy. If I’m being honest, there’s usually at least a tinge of insecurity when go down on a woman for the first time. In the first few minutes I’m trying to learn her body, how she reacts to different things, to feel the motion of her hips, listen closely to her breathing. But with Caroline I was frantic, desperate. When I felt how wet she was, I buried my tongue deep inside of her, then found my way to her clit, and teased and pulled at it with my lips, gently, then a bit harder, then gently again. I needed her to come. I wanted her to come harder than she ever had before. I wanted her to think of my mouth whenever she came. The first orgasm came relatively quickly. I could feel her wetness dripping down my chin.It took more effort to make her come a second time. It was dark, but I could see how perfect her little pussy was, see it glistening in her juices and my saliva. At some point, she lifted up a leg and draped it over my shoulder, and using my head for leverage, pressed herself against my mouth, grinding. I was licking her, dying to make her cum, but by that point I could tell that she was controlling her pleasure with her grinding, so I relaxed and let her use my mouth and tongue. She spasmed a little with her second orgasms and then all at once stepped back and fixed her skirt.
She offered me a hand, and helped me up. My knees were sore from the tar roof, and my mouth and tongue were exhausted. I could still feel her wetness all over my face. She kissed me, gently, and began to unbutton my shirt, and when there were just two buttons remaining, she started to slide the shirt off me, pulling it down my arms behind me, but stopping just above my elbows. She held it tightly behind me, effectively leaving me unable to use my arms without fighting to free them. Before I knew what was happening, her balled up panties were in my mouth, and she was leading me down the stairs of her building. It wasn’t late, and it wasn’t at all unlikely we’d run into a neighbor of hers. I was completely hard, which was obvious through my pants, and being pushed slightly from behind, a pair of panties in my mouth. We walked a flight of stairs, then down a long hallway. She took her time with the keys to her door, before finally opening it and pushing me inside. I stood like that, helpless, my erection obvious, and waited for what was next. I would have done anything to cum.
She undressed me slowly until I was standing naked in front of her, panties still in my mouth. She walked around me, taking me in, and then pressed herself against me from behind, kissing my neck, my ear, reaching around my body to begin very gently stroking my now throbbing cock. “You’re not going to cum until I tell you to, you understand?” I nodded and murmured a muffled positive response. “You’re no good to me after you cum.” She led me over to a large bed in the corner of the studio apartment, and pushed me down onto my back. I was laying beneath her, looking up. She reached down and removed the panties from my mouth, and then started to undress, revealing her incredibly body, and big, full tits. I’m not sure I’ve been more in awe of somebody before.
Caroline didn’t waste any time and straddled me, sitting must below my cock. She reached into the drawer and took out a condom, and slid it onto my cock, which jolted at her touch. She then adjusted herself and slid me inside of her, and started riding me and playing with her clit. I laid still at first, but picked up on her rhythm and started thrusting myself deeper inside of her. I could feel her getting wetter, and watching her looking down at me, both literally and figuratively, made me feel insanely dirty and hot. I loved how used I felt. She came again a couple of times, and then collapsed on the bed, spent. I laid next her, and wrapped my arms around her, kissing her neck, her ears, her lips. I told her how beautiful she is, how insanely sexy. We laid like that, cuddling for another 30 minutes or so. She was starting to doze off, and I realized she had no intention to make me cum.
Eventually, she looked over at me and told me I could jerk off If I wanted to. She told me “that I’d earned it.” She barely even acknowledged me while I stroked my cock, laying pressed against her, groping her beautiful tits with my free hand, kissing her neck, breasts, nipples, trying to do anything to re-earn her attention. All at once, I felt my cum well up, and realized I couldn’t hold off any longer, and felt a huge thick rope of cum splash across my chest, then a second gob hit my neck, followed by a third and fourth that landed on my abs. I was covered, breathing heavily. She looked at me, almost disinterested, and said “Next time you need to ask for permission before doing that. Go clean yourself up.”
We slept that night, cuddled together, completely naked like a couple who was desperately in love. But it wasn’t that at all, and we both knew it. In some ways, it was better.
Source: reddit.com/r/gonewildstories/comments/shjwut/mf_on_display_on_a_manhattan_rooftop
I live in nyc and might try this now during warmer weather