English Woman in New York

I graduated from college and moved into a tiny apartment in New York City right around the time that speed dating was becoming extremely popular. There wasn't a night that there weren't several different versions happening in various locations around Manhattan. I wasn't new to the city but I'd left a college campus full of women my age and had quickly realized that meeting women outside of college wasn't as easy as it used to be. I didn't want to go back to the college bars since that felt a little desperate and, by comparison, speed dating definitely reeked much less of desperation so I gave it a try. My results were mixed, but got better after trying it a few times and refining my approach. I did end up going on a few dates but hadn't made a real connection until I met Amy.

I'd discovered that the best way to get someone interested in going on a date with me was to talk about them. I'd come up with questions to simultaneously learn as much as I could about them while also letting them talk about themselves. If they only wanted to talk about themselves and never asked about me then that was usually the most important thing that I learned. With Amy, I'd already noticed her because she was super cute but, when I got my opportunity to sit across from her, I was not anticipating a British accent and almost dropped an extremely generic question that she'd likely heard multiple times already. Fortunately, I recovered quickly and instead asked how long she'd lived in New York, what she liked best about it and whether anyone had given her a proper insider's tour. She answered my questions and did ask several of her own, including whether I was angling for the opportunity to give her an insider's tour, which I admitted that I was.

When our time was up, I felt pretty good about our conversation and hoped that she felt likewise. Every other interaction paled in comparison so I put all of my eggs in that one basket and returned her name as someone I'd want to go out on a real date with. Fortunately, she did feel the same way and it wasn't long after that night before we'd planned out a day of exploring the city together. We'd only talked in generalities about where each of us lived but figured out a place to meet on a Saturday morning. I hadn't seen her since the speed dating event and I'm sure I was thinking that my memory was exaggerating how cute she was but, when I saw her waiting for me, she was absolutely as cute as I remembered. She was wearing a sundress and sneakers with socks so she was ready for a lot of walking.

After four years in college plus the time I'd lived in the city since graduating, I'd discovered a lot of hidden gems that the tourists and other visitors usually don't know about. I'd quizzed her a little bit to determine which she'd be more interested in and had come up with a basic itinerary, which fortunately ended up being a big hit. We walked, we visited shops and urban parks, stopped for coffee at a cool cafe, stopped for a unique lunch at a tiny restaurant off the beaten path and eventually stopped for a cocktail as well. We weren't quite back to the area where we'd met up when she said we were near her place and asked if I'd be interested in swinging by there. It seemed like she was comfortable enough with me to even ask so I was happy that things were going that well.

Her apartment turned out to be probably as tiny as mine but it was definitely nicer and in a little bit better area. We kicked off our shoes to let our feet breathe after so much walking then she got us both some water and we sat on the couch. We hadn't even held hands yet much less kissed but that all changed pretty quickly and we were soon making out sitting on her couch. As things began to get pretty passionate, she ended up straddling me and I was pretty sure subtly humping me. When she finally broke off from kissing me, it apparently was to tell me something not to catch her breath.

"I don't want you to think I'm a slag," she said, "because I haven't actually been with anyone at all in a long while which is probably why I feel like I'm about to explode."

"I know how to take care of that," I replied, swinging her over to the side and laying her on her back, "and I am more than happy to do it."

With her head on a pillow propped against the arm of the couch, I backed up and lowered my head as I pushed the hem of her sundress up toward her waist. I almost exploded myself when I saw the colorful bikini panties she was wearing but I only paused briefly to admire them before running my fingers over the front, which caused her to moan. I knew she had to be extremely fired up so I slid her panties down, revealing a well-groomed brown bush. I set the panties aside and started to run my tongue along her slit, tasting the abundant juices she was producing and causing her to moan even louder. I loved to eat pussy so I was psyched by this opportunity and figured that, if I did this well, it'd not only lead to more activity that afternoon but likely a return invitation. My goal was not only to make her cum but also to make her feel a high level of pleasure while not drawing it out too long and making her feel like I was denying her the orgasm she obviously desperately needed.

After lapping at her juicy pussy, I slipped a finger into her and began to slowly slide it in and out while licking and sucking her clit. This got her moaning louder and longer while subtly rocking her hips toward my face. Her pussy was not only juicy but pretty snug as well so the thought of potentially slipping my cock into her had it practically bursting out of my jeans. Despite that, I was not rushing to get her to cum so that I could fuck her; I wanted to savor this opportunity for myself while also providing a pleasurable build-up to what would hopefully be a monumental orgasm. The longer I was eating her, the louder she was moaning and the more pronounced the rocking of her hips was becoming. I did glance up a few times to see the look on her face that suggested she was experiencing a great deal of pleasure, just as I was hoping. Between that and the moaning, I was feeling good about how things were going.

As she was getting close to cumming, her body was tensing up and she was arching her back. I didn't change anything with my technique because it seemed to be doing the trick and it wasn't much longer before she briefly went silent before letting out a cry. All of the tension seemed to leave her body then she started shaking while I continued to devour her pussy as she was cumming. There was a flood of additional juices around my finger so I was really hoping that she'd want to fuck after this orgasm had run its course. It was probably a lot to expect with this being our first date but I most certainly had not expected to have my face between her thighs, eating her pussy that day.

When she went still and let out a sigh, I raised my head and slipped my finger out of her pussy and into my mouth to suck off her juices. I straightened up a bit more, first just gazing at her pussy then looking up at her face. She looked content but her eyes were still closed so I took a moment to appreciate just how cute she was. I was smiling when she opened her eyes so she smiled back at me then started to sit up. She reached for my belt and started to unfasten it then worked on getting my shorts open, too. When she pushed my shorts and underwear down together, my rigid cock sprung out so she immediately gripped it and gently pumped it.

"Sit," she said, so I maneuvered around until I was sitting then she immediately straddled me. Her dress was covering her pussy but she just reached under it and guided my stiff cock to her hot, wet pussy and lowered herself down on it. We both moaned as my cock slipped all the way into her and she just sat there briefly, feeling it inside her. She brought her lips to mine and we went back to making out as she slowly began to move up and down on my stiff cock. Her snug, slippery pussy felt amazing so I was pleasantly surprised that I didn't immediately blow a load. I slipped my hands up under her dress and caressed her soft, smooth ass while pushing up into her each time she dropped down.

Although she started out slow and we were able to make out, she gradually picked up the pace the longer she was riding me. I think a combination of her being on top and the slow build-up helped my staying power so I was able to enjoy the pleasure I was feeling rather than trying to distract myself. Realizing that I had only briefly caressed her boobs through her dress and bra as we'd been making out, I moved my hands up from her ass but still under her sundress, first fondling her boobs through her bra and feeling her hard nipples pushing out against the thin material, then around behind her to unfasten her bra. Bringing my hands back around, I slipped them up under the cups and caressed the soft, smooth flesh while brushing my palms over her hard nipples. Her boobs felt pretty big, though it may just have been relative to her small frame. I'd definitely checked them out, both at the speed dating event and earlier that day, but it had been difficult to really get a sense of how big they were because of what she was wearing. Now I was feeling like there was the potential of laying my cock between them if things continued to go as well as they currently were.

I don't know if it was due to my hands on her boobs or if my cock got harder as I was fondling them or if she was just reaching that point from riding my cock but she eventually pulled her mouth away from mine and was moaning louder and longer. She had continued to pick up the pace at which she was riding me so it was becoming more difficult to continue making out anyway. Her boobs were also bouncing as a result but, since I could not watch them, I just continued to fondle them instead. It wasn't too much longer before she dropped down onto my cock and just remained there, going briefly silent as though holding her breath, then crying out as her entire body was shaking. There wasn't much else I could do at that moment so I just continued to fondle her boobs.

Her orgasm was long and appeared to be highly pleasurable so I was happy to have helped her to achieve that. My own orgasm, though it hadn't really been building up in earnest quite yet, still backed off with her just sitting there so I was hoping we might be switching things up a bit. I wasn't disappointed when she had recovered enough and opened her eyes, smiling then kissing me some more before moving off of my cock. She positioned herself on all-fours beside me so I got up onto my knees with my stiff cock sticking straight out in front of me. I raised the hem of her sundress, revealing her sweet ass, which I then ran my hands over before guiding my cock back into her. She moaned and pushed back until I was fully embedded, with my hips pressing against her sweet ass. Holding her hips, I started to slowly slide in and out, relishing the pleasure of fucking her snug, slippery pussy.

I'd pushed the hem of her sundress up past her waist so that my hands were on her bare hips and I could look down at her ass, which was jiggling slightly each time my hips tapped against it. Once we had a good, steady rhythm going, I slipped my hands further up under her sundress until they found her swinging boobs. I cupped them, hefting their weight in my hands and feeling her hard nipples against my palms while still sliding my stiff cock in and out of her. She reached down under herself, I assumed to caress her clit as I was fucking her, so I thought it was great that she was being proactive about her own pleasure. I didn't assume that it was because my cock wasn't pleasuring her enough, just that it was probably heightening the pleasure she was feeling. Anything that made her enjoy this sex even more was fine with me because I figured it would further encourage a return invitation.

Her moaning was getting louder the longer we were fucking and somehow her pussy was feeling even hotter and wetter than it already had been. I could feel the stirrings of my orgasm but I was hoping that she would cum again before I did then I could let go and experience what I was expecting to be a monumental orgasm of my own. When she started pushing back against my thrusting, I straightened up and held her hips again, pulling back as I was pushing in to make sure she got the full length of my stiff cock. I was looking down at her sweet ass, watching the jiggle, when she pushed back and held there. I pushed my cock into her as deeply as I could and kept it there, pulling back on her hips. She went briefly silent then let out a cry as her body started shaking. Once she'd started cumming, I slid my cock and out of her a few times, relishing the increased lubrication and feeling my own orgasm continuing to build.

After another long and apparently highly pleasurable orgasm, she moved forward until my cock slipped out of her then turned to face me, both of us on our knees. She brought her lips to mine so we made out briefly as she reached down to stroke my stiff cock. It was just a moment later when she had me sit then knelt on the floor before me. She lowered her head and engulfed my cock in her mouth which made me moan. I leaned back and watched as my cock disappeared repeatedly into her mouth, still surprised that we'd reached this point already but perfectly happy about it. She left nothing to be desired when it came to sucking cock so my orgasm was soon building again. Somehow she managed to hold it off and draw out the pleasure I was feeling, which I certainly appreciated because I wanted to enjoy her skillful cocksucking for as long as possible.

There came a point where, no matter how skilled she was at holding off my orgasm, she was just too good at providing oral pleasure so my orgasm was becoming imminent. My cock was swelling even more the closer I was getting to cumming but she was not fazed at all and just continued to suck me off, though I believe she was aware that I was getting close and was no longer trying to hold off my orgasm. She switched gears from drawing it out to getting me the rest of the way there and I was eager to blow my load down her throat. When I did make some sort of noise and started spurting into her mouth, she continued skillfully sucking me off as she swallowed my load. Only once I was completely spent did she release my softening cock from her mouth and look up at me with a smile on her face. She got off her knees and sat beside me on the couch.

"I'm very happy that I ended up liking you so much and that you're so good at making me cum," she said, "I don't usually move so quickly but it has all just felt so right."

"I agree and I'm still really looking forward to getting you completely naked," I replied, which inspired her to look down and confirm that her sundress was still hiding her body.

"Why don't we go to my bedroom and continue things there?" she suggested so we got up and I followed her, leaving my shorts and underwear behind and shedding my shirt along the way. Her bed nearly filled the small bedroom but there was enough space for me to raise her sundress up as she raised her arms. I looked around for where to hang it but she just took it from me and dropped it on the floor, followed by her bra. Finally seeing her completely naked, I just stared. Her boobs were as big as they'd felt, topped with large areolas and hard nipples. She was thin, though she did have some nice curves, and was fair-skinned. We made out, standing there naked, for a minute and, feeling her soft, smooth skin against mine, I could feel the blood already returning to my spent cock. We crawled onto her bed and resumed making out while running our hands over each other and getting each other even further worked up. She was soon stroking my nearly rigid cock, getting it ready for more fucking.

Once I was stiff enough, she lay on her back and beckoned me over her so I obliged and, supporting myself on a forearm, guided my tool back into her hot, wet pussy, which made both of us moan. I wouldn't say that I had an aversion to the missionary position necessarily, and it was nice feeling her skin against mine, but I didn't have as much luck with my partner cumming in this position. I was hoping that my having cum once, as well as her being so pent up, would work in my favor and I'd be able to satisfy her again before cumming myself. Little did I know just how sexually in sync we were and that there was going to be more cumming and more than the missionary position happening in that little bedroom.

We were making out as I was slowly sliding my cock in and out of her snug, slippery pussy while she was raising her hips to accept my thrusts. Despite my orgasm not yet beginning to build, I was taking it slow just in case, though I was sliding the entire length of my cock in and out of her. Her bed remained quiet, not alerting her neighbors to what was going on with any rhythmic squeaking, but the same couldn't be said of Amy. Once I started to gradually pick up my pace and was fucking her just a bit harder and faster, she ended up pulling her mouth away from mine and started to moan loudly. I wasn't worried about any of her neighbors hearing because I was thinking that this was a good sign that she was actually building toward an orgasm of her own. I didn't change anything with how I was fucking her at that point but I think I was able to relax a little and enjoy it even more than I already had been.

She pulled her knees up toward her boobs which I think was allowing me to provide her with maximum penetration though I was fucking her only slightly harder and faster by this point. Her pussy seemed like it was becoming even hotter and wetter and, since she was also moaning louder and longer, I was starting to feel more confident that she was going to cum before I did. I could actually feel some stirrings of an orgasm but it would have been difficult not to with how incredible it felt to be fucking her. I wouldn't have minded cumming right after she did but I was focused on trying to make sure she did cum first, though that certainly didn't mean I wasn't savoring the intense pleasure I was feeling.

In this position, other than the moaning and her pussy feeling hotter and wetter, there wasn't really a sign that she was right on the verge of cumming. When she did cry out and start shaking, it seemed pretty sudden and was definitely a pleasant surprise. I continued to fuck her as she was cumming, hoping to provide even more pleasure to her but also, since her pussy seemed to be flooded with even more lubrication, to enjoy a higher level of pleasure myself. Her orgasm appeared once again to be long and intensely pleasurable so I was pleased that she continued to clearly be getting a great deal of pleasure from being with me.

When I was certain that she was finished cumming, I was about done with the missionary position so I slipped out of her and moved around until I could lie on my back beside her, only my feet were toward her head and my head toward her feet. She rolled toward me and moved laterally until her pussy was over my face and her face was over my stiff cock. As I gazed up at her trim, brown bush, she gently grasped my cock and engulfed it in her mouth. I moaned and just enjoyed the feel of her lips sliding up and down my cock a few times before raising my head and running my tongue along her slit. She paused briefly to moan as I slurped up her juices then we both focused on pleasuring each other while being pleasured.

I figured since I'd been feeling the stirrings of my orgasm when we'd been fucking, I'd be building more quickly toward mine but I was getting the sense that, not only was she cumming a lot due to being pent up, but once she had an orgasm, subsequent ones were easier to achieve. I was okay with her cumming more than me, not thinking at that point that it'd be more likely to result in a return invitation which now seemed inevitable, but more because it was rewarding her for going against how she might typically take things a bit slower. I was also thinking that, if she came again before I was too close, we could try something else and I already knew what that was going to be.