Guy dates girl(s)

My New York dating chronicles

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The Model

I’ve dated a few models in “my day” (saying that makes me sound like a grandpa, right?) and on the whole, the stereotypes are true - they’re tall, skinny and vapid. This girl was different.

Let’s say I work in the creative field. She and I had crossed paths a few times before and the chemistry was palpable. I like a tall, skinny girl as much as the next guy but personality and a nice face matters more than anything and this girl’s got both. She’s independent, successful, quirky, and speaks a fluent language (specifics would make me feel like I’m giving too much away, so use you’re imagination). We were fast friends and on the whole, I was around her what’s most important when around your girl or guy - myself. You like that, right?

Before we’d even hung out outside of work capacity, I asked her to be my date to a party. It was weeks away at the time and our heavy txt and IM flirting was too much. I had to see her. So I asked her to lunch, under the guise “hey, come help me pick out some shoes for this thing we’re going to.” She obliged. We spent the afternoon together, walking around and getting to know one another. We went back top my place to get out of the cold and hang for a bit. It’d been a little while since I made the move on a girl so you can imagine I had a pit in my stomach the size of a baseball when we I ended up sitting on my bed, shoulder-to-shoulder with this model watching funny videos on my computer. You know when you look at someone and you linger? We lingered. And as soon as the moment felt right, I turned my head away like a character in The Waltons or some shit.

I had an appointment in an hour, so we had to say goodbye. I wanted to kiss her but didn’t know when I’d muster up the courage points. I handed her her coat and then absent-mindedly put her scarf around her neck. Luckily I’m not a douchebag (I seriously didn’t plan this move) but I realized as soon as I did this that I set up the perfect moment. I kissed her and it was awesome. Perfect fit. Good feeling, right?

So we go on our party date, things are going well, we go out a few times, dancing, a couple of dinners, fooling around. She’s revealed to me at this point that there’s a guy in her life she hadn’t officially ended things with, but who she insists is not great for her (“He doesn’t challenge me. I know we aren’t getting married.”) Since things were at their early stages, I thought that was totally fine, considering she seemed to be playing for my team and I didn’t set out to look for anything serious.

By the time New Years rolled around, I felt comfortable enough to invite her up to my folks’ place. Not just her and I - it’d be my cousin and his girlfriend and the two of us. She came up, we had a great time. Slept together for the first time (first three times) and she was growing ostensibly attached. It was a great weekend. By the end, I could tell things were gonna get serious.

We get back to the city, she and I don’t see each other for a few days. She texts me and says she officially put the cap on the “other guy” situation. Another couple of days go by and we don’t see each other. I’m busy and whatnot. She ends up text me stuff about how confused she is. How bad she feels. I say, “don’t sweat it, let’s talk.” I go to her place and she tells me she’s been really confused because this “other guy” (who shares a name with me… isn’t it ironic?) has come crawling back and has made a mistake and wants to show her how much he can REALLY love her. She’s seduced back into it.

“I’m so confused because he’s all I’ve wanted for 6 years but things have been up and down. And with you, there’s so much potential…” I totally sympathized. I told her I’d been in a similar situation before. I once crawled back to an ex-girlfriend of many years after I realized she just started up a serious relationship with another dude. I felt like I had to prove myself, both to her and my conscience. So I cried and begged and pledged and when I got her back, I got to give it a real, mature try - I gave the relationship a go with no pretense, being as lucid as possible, as a new man. In the end, it didn’t work out, but at least I got to find out for sure if it really worked. So anyway, I sympathized, and I told her as much. I really did totally understand. On the one hand it sucked I wasn’t about to spend more time with this beautiful, talented woman with a great personality but on the other, relationships are a lot of work. We both enjoyed each other, we had our time, let’s be friends, our story ends.

Not yet.

A week after we cut it off, she asks me to see Avatar. She’d started things back up with he-who-shares-a-name-with-me, but I figured, “what the hell, we’re just friends.” So in the cab on the way to the theatre, I ask, “So, does your boyfriend know we’re hanging out?” She goes, “Yeah. He’s not thrilled.” I sort of sat there for a second. “Don’t you think that’s a little wrong?” She goes, “Why would it be? He knows we’re not going to hook up or anything.”

For the rest of the night and the sweeping, three hour James Cameron epic with flying blue cats, I was on edge. She asked me to drinks afterwards and that’s where I drew the line. “I got an early morning tomorrow, I’m sorry. Have a good night, babe.” I gave her a kiss on the cheek and high tailed it out of there.

That night, we IM’d one another. She goes, “Hey, are you okay? You seemed a little on edge tonight…” I proceeded to tell her that I was really looking forward to being friends with her, yet her asking me to Avatar after getting back with her ex-boyfriend - who was less than thrilled with her hanging out with the guy who only a week before she was sleeping with and eating his mom’s cooking - made me uneasy.

“I was really hoping we could be friends,” she said. “Me too, babe. But I still like you and I miss you and that’s a problem.”

“I know,” she types. And we haven’t spoken since.

It sucks, because I realize she’s a little too young upstairs to have the wherewithal to know what isn’t toxic for her. I respect having to close chapters; having to figure out what’s right for you, even if it means going back behind enemy lines. I hope she’s doing well, and maybe we’ll try this again sometime when she’s not being a total bitch.

Jk.

Filed under dating, model sex cheating avatar

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The Squirter

It took courage writing that title. I swear l’m not categorizing the girl. She’s so much more than the sum of her sexual mythology.  But, yeah. I dated a squirter.

We went on three dates, slept together on the first and last. The last time we saw each other, she came to my place, we shared a bottle of wine. Talked for a few hours, and started fooling around.

Now, it’s a dangerous thing to get physical with someone you don’t know that well, but we played it safe. I did start going down and her and had a brief moment of panic when she grabbed my shoulder - after I’d coaxed my way down there, reassuring her she had nothing to be embarrassed or ashamed of - and pulled me back on top of her. Shaking her head, “Mm-mm,” as if to say, “Don’t. Bad idea,” I listened. She got on top of me. And got close to climaxing.

“I’m gonna come… Oh god, it’s going to be a mess…”

I gave her another minute of encouragement until she had an orgasm. ”Oh god. I’m squirting!”, she goes. No wonder she didn’t want me down there. If she’d have finished with my mouth on her, it would’ve been the sexual equivalent of dunking my head under a faucet. When she finished, no joke, it felt like someone took a lukewarm cup of tea and poured it all over my crotch. It wasn’t nasty in the least. While foreign to me, I liked it a lot. I’d go so far as to say it was pretty hot.

“I’m so sorry. Oh god, I’m so embarrassed,” she said, covering her mouth, sheepish. “No way! That was hot,” I said, “Do it again.”

And she did it again. And again. Four times. My sheets were soaked. She was enthralled. I was smug.

“That’s never happened before,” she said.

The next morning, we had breakfast and walked around the neighborhood. The sex was good, but the conversation was stale, and though we’d slept together twice and had some really tantalizing conversation, I had to end it.

What’s proper protocol to end something in which you meet a girl, go on a couple dates, sleep with them twice and they tell you that they “like you so much.” That you’d been their first lay in a year? I found myself in a position where I had to break it off over the phone. Since my work schedule wouldn’t allow our conversation over coffee, I figured I’d do the next best thing (I learned my lesson long ago that breaking something off over via, say, Myspace message, isn’t the greatest or un-douchey of methods).

“I’ve been thinking a lot about us over the past couple days, and I was thinking, I don’t want to waste our time. I like you a lot but I think you and I both know this isn’t a love match.”

Ugh. That shit’s never easy. But luckily, she agreed. Told me although she wasn’t looking for a serious relationship, she did find me very attractive and was open to the idea of being together at some point, but appreciated my honesty, and recognized the missed connection on the overall. I told her I’d love to go to coffee and talk at some point. Some of my female friends don’t think that’s entirely necessary, but I feel like kind of a shit for ending it over the phone. Fuck me, right? Anyway, I don’t want to make coffee an empty promise. Hopefully she’ll come around.

Thus ends the tale.

Filed under dating sex squirter