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.
