The First Date Chronicles: 1

What does it mean to have a successful first date? Every guy probably has a slightly different definition of this. For some guys, it’s meeting a woman that you can see yourself spending the rest of your life with. Maybe the date ends in a kiss, nothing more, but the promise of a long-term relationship is there. Absolutely nothing wrong with that, but I’m sure most guys reading this blog are looking for something different. You’re probably hoping to get laid on the first date or at least get to a place where it’s all but guaranteed on the second date. 

If that’s your goal, I’m here to help. This post is the first in an ongoing series I’m planning to write about first dates. My next post will be an overview of strategies to use to make sure your next first date is successful. And after that I’ll continue to write a series of posts on different first dates I’ve had. So let’s get right to the action. The first installment of The First Date Chronicles.

About a year ago I was swiping through Tinder and came across this profile that made me stop swiping right away to take a closer look. The girl in question was 19 years old and she was so sexy I couldn’t look away. The best way I can describe her look was half teen beauty queen and half aspiring porn star. Beautiful but with a wild side. I hardly ever Super Like because I’m not convinced it does anything but with her I just couldn’t resist. I sent her a Super Like and went about the rest of my day. 

About a day later, I get an exciting notification. The girl, let’s call her Madison, had liked me back. I shoot her a message and she writes back within an hour. I had been on Tinder long enough to know that the speed of her reply plus the amount of emojis she was using mean that there’s a good chance I’ll end up going on a date with this girl and hopefully fucking her if I play my cards right. After a few messages back and forth, I ask her out for a drink, but we can’t find a night when we’re both free for about a week. So to prevent her from losing interest in the meantime, I keep texting her. This wouldn’t be such a problem with girls my age but if you want to date younger girls, you have to play their game sometimes. And this means not letting them get bored. 

Anyways, I can tell from the vibe I’m getting from Madison that I can probably turn the conversation sexual without scaring her away. At some point she mentions something about an ex boyfriend. Perfect opportunity. I ask if she broke up with him because he didn’t fuck her well enough. And oh boy did she take the bait. She says she broke up with him because he was “immature” but that she did get frustrated because she was more sexually adventurous than him. Vibrators, butt plugs, handcuffs – she loved all of it. But it intimidated her ex. By this point I know I’m going to have fun with this girl and I have to see her in person ASAP. 

The thing about girls that age is they don’t always understand adult responsibilities. She texted me a few times during the middle of the work day asking if I wanted to grab coffee with her. I obviously did, but I couldn’t exactly tell my boss that I was leaving after lunch to go on a date with a teenager and hopefully fuck her afterwards. I get another text from her on a Friday around 4:30 pm saying that she’s going to hang out with her girlfriends later but wants someone to have an early dinner with her beforehand. Normally I’d find that kind of ridiculous. But given her age, I knew that she’d get bored if we didn’t hang out soon. So I snuck out of work a little early and went to meet her at a restaurant I suggested. 

I get a booth and within a couple minutes she arrives. And once I see her walk in – holy shit am I glad I left work early. She’s wearing this tight dress that hugs her body perfectly, looking every bit the teen beauty queen turned porn star she did in her pictures. She walks over to me and I stand up to give her a hug. And when we hug, I can feel that the chemistry is electric. I know this is going to end in sex, I just have to figure out how to navigate the logistical challenge of her going to hang out with her friends later. 

At first, she goes to sit on the other side of the booth. But I ask her to come sit next to me instead. This is a little compliance test I like to give at the beginning of a date. If a girl is willing to do that, she’s probably willing to be led to do other things too. She happily comes to sit next to me and I can feel the sexual tension shoot through the roof. But we’re here to have dinner so I don’t want to come across as too eager too quickly. 

We order our food and I order a drink. Since she was only 19 and couldn’t order one for herself, I gave her little sips of mine when the restaurant staff wasn’t looking. The conversation was good, nothing super intellectually stimulating or anything, but I was able to keep the energy going and make her feel comfortable. 

Having her sit next to me was also a strategic move. Had she sat across from me, it would have been much harder to start the physical contact that is critical to get a girl comfortable enough to sleep with you. But since she was right next to me, it allowed me to start doing some playful touching to see what she was comfortable with. If she said something even a little bit funny or interesting, I would touch her leg or her hand, and since she seemed comfortable with it, I kept doing this throughout the time in the restaurant. 

When the food came, there was already lots of touching going on and I could tell she was feeling pretty comfortable with me and maybe even getting a little turned on. The food gave me another opportunity to introduce a little compliance test. I told her she could try my food but only if she let me feed it to her. And she happily agreed. Now, this isn’t something I’d recommend trying with every girl. Some girls might get offended by something like this on the first date, and it could ruin your chances of a second date or of ever sleeping together. But I had enough experience to be able to read the situation and I was almost certain she’d react well. 

By the time the check arrived, I was pretty confident she’d be willing to skip hanging out with her friends to come back to my place. When I asked her, I could tell she wanted to, but she wasn’t sure what to tell her friends. After some playful back and forth, she ended up deciding she couldn’t bail on her friends. They knew she was on a date and she didn’t want them to know she was fucking an older guy on the first date. I was disappointed for a few seconds, but I had a backup plan.

She still had over an hour before she needed to be at her friend’s house. And it was raining outside. So I suggested that to get out of the rain, we go chill in my car for a little while. She liked the idea, so we walked over to my car and got inside. I took her hand and held it on the way to the car, and almost as soon as the car doors close, we’re making out. Pretty soon I start kissing her neck and ears and I can tell she’s really getting turned on. But there’s a problem. I’m parked on a busy street and we’re in plain sight of everyone. Luckily, there’s a parking garage just a block away so I suggest we go there for some more privacy. 

After finding a secluded spot in the garage, we start making out again. But of course, the front seat of a car isn’t the most comfortable place to hook up. The center console is in the way and stopped us from really getting close. So I told her we should go to the back. The kissing resumes once we’re in the back seat, this time with a lot more touching and groping. I reach down to start playing with her pussy but she stops me. She says she’s on her period. Now, I’ve heard this excuse before. Sometimes it’s been real, sometimes probably not. I got the feeling from Madison that she wasn’t making it up, but I asked her to let me see under her panties to make sure she wasn’t lying. And sure enough, there was a tampon. Again, this isn’t something I would have asked most girls to do. But I got a feeling from Madison that she wouldn’t mind, and I was right. If we were in a bed, I would have told her I didn’t care about her being on her period, but being in a car without any towels or anything, I didn’t think period sex was a good idea. 

So we kept making out and I took out my cock. Before I could tell her what to do, she took the hint. She started giving me a spectacular blowjob that I can honestly say was one of the best I’ve ever had. I’m alternating between moaning in ecstasy and doing quick glances around the parking garage to make sure no one is looking. Since her pussy is off limits for the night, I pull down her panties a little and stick a finger up her ass while she’s sucking my cock. And wow does she like it. She starts moaning and sucking my cock even more enthusiastically, swirling her tongue in a way that sends me straight to heaven. I wish she could have kept doing this forever but the last thing I wanted was for a security guard to bust us or someone to park near us before I had a chance to orgasm. 

After a few more minutes I decide to give into my urges and allow myself to finish. I cum into Madison’s mouth and she swallows every drop as I catch my breath and come to my senses after such spectacular pleasure. 

In the afterglow, I ask her if that’s what she expected to happen. She tells me she didn’t, and that I’m bad for corrupting her like that. I’m not sure if I believe her, but I don’t really care either way. I talk to her a little bit more about her plans for the evening and ask her if she’s going to tell her friends about what happened. She laughs and says she’ll just tell them we had a nice dinner. 

We did end up having real sex on the second date, but nothing will top the trill of that first experience with her. I’ve had sex on plenty of first dates before but something about her age, it being in a semi public space, and my success at salvaging what looked to be a lost cause of a night really make this one stand out in my mind. 


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