Amazing Sex with [M]y [F]irst Kiss More than a Decade Later

So this just happened about two months ago and was awesome in every way. I was traveling for work to NYC (from the Midwest city where I work in advertising) and decided to contact Tina, a girl I was close friends with in high school but had not really kept in touch with outside of following each on Instagram. We’re now both 27 and living typical young professional lives, pretty committed to our jobs and making decent money. Tina was actually the first girl I kissed when I was 14. It was a peck but at the time, obviously, felt unreal. Two years later we made out at a party, but other than that, we were just friends, fairly close, but nothing remarkable.

Tina had been living and working in New York since college, for one of the big accounting firms. She was always very bright and driven, though with a noted wild side. She’s a petite red head, though she doesn’t have any freckles. She’s got a great, tight body which she keeps pretty toned from a lot of Crossfit and spin classes, and really pretty blue eyes. Her boobs are pretty big for her frame, and are noticeably firm. She loves posting a good bikini picture on Instagram, and if there’s one word to describe her, it’s “tight”.

I didn’t really have set intentions when reaching out to her, although I definitely fantasized that it would be hot if something happened. But I had no idea about her life, who she was dating, or if she was interested, and I was more than happy to just have a drink and catch up.

We met up after work at a bar she recommended, and it was a typical yuppie happy hour spot, with a lot of finance-looking guys in button downs. Working in advertising, I have a bit more of a hipster look, usually bearded and I keep my hair a little longer. So not my typical scene but totally fine. I saw Tina sitting at high top table and she was sporting a cute blue sundress, which was conservative enough for work, with some wedges. This was NYC in August, so it was hot and humid. We hugged and she looked great, not much different than her younger self in my memory, just more confident and mature, which is always sexy.

We had a few drinks a piece and laughed about a variety of memories. It was a great time, though I wouldn’t really say flirty. She did mention a recent boyfriend that was no longer seeing, but stressed it hadn’t been serious. I definitely took this as a little “hint hint” but I certainly didn’t want to overstep my bounds. When we closed out, she suggested going up to her place for a nightcap since she was right up the road. At this point, this felt like an invite.

She lived in an upscale high rise with a cool view of the Empire State building from her 14th floor unit. The place was decorated really nicely and it was clear that she was doing well for herself, affording to live alone at only 27 in an expensive city. Once we got inside, she poured us both some wine and handed me the glass in the kitchen.

“Cheers,” she said, clinking glasses.

“To knowing each other for almost 15 years,” I said.

She smiled politely but gave me a look that said “please make the first move so I don’t have to.” Hoping I read the look correctly, I put my glasses down and leaned in for a kiss, and indeed, I was correct. We began making out like we were in high school again as I pressed her against the kitchen counter. I began kissing her neck and before long she suggested we move to the bedroom.

She had a large king bed which she pulled me on as we fell together. She began to reach down to undo my pants, but I got on top and spread her legs, flipping up her dress and exposing a light pink thong which I tore off. Her pussy was shaved and tight looking, and I immediately went to town eating her out. I love going down on girls and I’ve been told I’m very good at it. Before too long, she was moaning and wet, and she had an obvious orgasm with her legs wrapped around my head.

She stood up as I laid on the bed, and this time I let her take my pants off and suck my cock a little bit. Her technique was fantastic, as she used a lot of hand, which I love. My dick really grows a lot, so it went from about 5″ to 8″ as she sucked me. To my surprise, she began to slowly stroke my wet cock as she moved her mouth down to my balls and then my taint, licking very close to my ass. Not many girls I know venture there, and it was an amazing feeling.

“Condom?” I asked, and she got up, opened her night stand drawer, and tossed one at me. As I wrapped the goods, she positioned herself in doggie on the bed, really propping up her ass to expose herself. I wasted no time and began fucking her doggie style, her dress still on, and it was just perfect. Her pussy was tight and pink as she arched her body into me. I reached around and rubbed her clit as I fucked her, and she came again, drenching the condom in her white juices.

To my surprise, she grabbed my hand and pressed it into her asshole, my thumb really pushing on her hole. I had never done anal or anything in the anal family, so I was taken aback and kind of moved my hand away, always wanting to be respectful.

“Spit on my asshole and put a finger in,” she moaned.

I could not believe the dirty talk, but I was not going to argue. I hocked a pretty big amount of spit which fell into her buttcrack and I spread it around her anus. I then licked my index finger really well and slowly inserted it into her ass. I had no clue what I was doing but she was obviously loving it, and all this was going on as I steadily pounded her pussy, my balls really dangling now from the heat, consistently bouncing up and hitting her clit. Her asshole was so tight and I found myself wondering how anal even works, but I was not going to answer that question tonight.

I felt myself reaching completion and I came hard, filling the condom with my semen as both of us felt this warmness. I gave a few more pumps to make sure I was good and empty, and rolled over next to her, relishing the moment before I needed to remove the full condom. She really onto me and laid on my chest, and gave me a look that was like “wow.”

We both got dressed, she putting on her PJs, and chatted a bit before I said I should leave. It was obvious we both had a great time, and I mentioned that I had one more night in town tomorrow. I asked her if she was busy and she said no, so I invited her to dinner. She said, “Just come here, we’ll order in.” Needless to say, I’ll have to post about our second night together soon, as it certainly memorable as well.

Source: reddit.com/r/gonewildstories/comments/9ne6v1/amazing_sex_with_my_first_kiss_more_than_a_decade