My First Time

Male, 19, Florida

I was 19 and I was a big nerd. It wasn’t that I was very unattractive, or not confident, or not popular, but none of these factors seemed to come together at just the right time. I was more or less a college drop out, even though I was a genius and I was supporting myself living with a roommate in a tiny condo. I was going through a pretty serious bout of depression as well. Then I decided to try online dating, because most of the girls that I had ever really ‘talked’ to I had met online. Although none of them lived anywhere near me. I messaged a lot of girls, but most of them didn’t respond. It really is pretty soul sucking to have to come up with something witty to say to hundreds of girls online knowing that most of them wont even bother to write you back.

So I messaged this one girl who was really kind of pretty. Honestly I was looking for a relationship, but she apparently wanted a ‘casual encounter’, a phrase that the website later did away with because 90% of the women who were looking for that were actually men pretending to be women. I messaged her a witty response to her Hitchhiker’s Guide quote (a favorite of mine) and a thinly veiled attempt to get to the bottom of her ‘not liking vanilla’. I had no idea that I was right and no idea that any woman would actually be that upfront.

We messaged back and forth for two days and then I gave her my phone number and she said she’d text me the next day, which she did while I was at work. We had two phone conversations that spanned several hours each. She was 25, went to the local university as a biochem major. She was a self proclaimed serial monogamist and was exploring her own sexuality and most importantly, she wasn’t turned off by my experience or lack thereof. So we scheduled to meet up the following Saturday night after she was finished a couple drinks with her lab group, which was previously arranged.

I met her at the gas station around the corner from the townhouse she lived in with her aunt at about 9 or 10 at night. She got out of a tiny blue Civic and she was wearing a silvery top and jeans. She hugged me and said hi. I told her that she was gorgeous and she looked away embarrassed. She pointed at the row of townhomes across the street and said that’s where we were going, to put 9799 in the keypad at the gate and follow her.

Her aunt was asleep upstairs, so we still settled into the pullout couch on the first floor. My heart was beating out of my chest. She told me it had been awhile since she’s had any kind of kinky sex and was very excited. Then she sat down and looked at me expectantly. I sat down next to her and kissed her. I kissed her deep. We laid back and continued kissing, but I could tell that she was getting impatient.

I took off her shirt and her pants. I took off all of her underwear and told her to undress me which she seems excited enough about. She told me that socks always came off before pants and soon had everything else off too. She kneeled in front of me and looked up at me, but I couldn’t get hard at all. She went down on me excitedly but to no avail. I laid her down on the bed and kissed her whole body. She had to tell me that her nipples had had enough after a while. She asked me if I wanted a drink and gave me the only thing alcoholic she had in the whole kitchen, a 12 oz bottle of wine.

Still nervous and slightly buzzed, I fingered her, which got a good enough response, and I spanked her, which she really liked. When I was semi-hard, I told her to hurry up with the condom and she rode me as best she could but it just wasn’t happening and I kept apologizing the whole time, but I told her to stop. She came twice, though, grinding on my leg and told me that I was “not bad for a kid”.

We went upstairs and cuddled in her bed and several hours later tried again to the same result. In the morning, we went to breakfast after her aunt had already left.

The next week, we did it again and it was spectacular, thee times in two days. The sex was really fantastic, kinky, and varied. We kept going for about five months, but eventually we stopped because she was spending her last semester abroad in Spain.

The thing is that she never wanted a relationship and we were always just friends with benefits. I knew that she was sleeping with other guys and I asked her just not to tell me about them. She knew how I felt about her, but the first thing she told me was that I wasn’t allowed to get attached and I said I wasn’t going to.

She’s in Spain now and I haven’t heard from her since.

Image via Flickr.

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