Hookup

I’ve read so many blog posts about them over the years, but never did I think I would have a hookup of my own to write about.

It all started a couple of months ago.  My niece and I were talking about dating and swapping stories… hard to believe sometimes that she’s 21 now.   Even harder to believe she’s on Tinder.  She even pulled out her phone and swiped left and right through a bunch of guys.  Very, very interesting watching the process on the female side.  She showed me some of her conversations too.  Not to be outdone, I showed her screenshots of my old conversations.  She really got a kick out of them – so much so that I decided to go back on Bumble with a joke profile and collect more funny screenshots.

This went on for a couple of weeks when one day I got a message at 4AM:

“Hey Tommy, seems like you got low enough standards for my liking :)”

“And apparently we’re both night owls,” I wrote back.

“I think I should say that I have jet lag.  But the truth is…”

“You’re horny…?” I suggested.

“A bit.  Fancying some good old fashion missionary.  Ok… or maybe I will be on top for a little.”

Okay… this had to be a joke.  Someone read my profile and was clearly fucking with me in return.  I even suspected it was someone I knew in real life.  Plus she only had one picture, which is usually a red flag.  But we chatted until the sun rose, and during the day she sent me photos of herself in various states of undress.  After less than 24 hours of sexting and steamy conversation, I met her in a bar in Brooklyn.

#50

Right up until I walked through the door, I kept thinking it was too good to be true.  I half-expected to see one of my friends sitting there, although I doubted any of them would travel all that way just to play a prank.  And the more I talked to her online, the more confident I was that I wouldn’t end up meeting some 40yo hairy fat dude.  But sure enough, she was a real person, sitting right at the corner of the bar in blue jeans and a black top just like the said she would be.

Phew.  And wow.  She looked better in person than I imagined.  Except when I tapped her on the shoulder and said her name, she didn’t look entirely enthused to see me.  Uh oh.  I greeted her and told her I had to use the bathroom and I’d be right back.  After the long drive into the city I was fit to burst, and I went downstairs and pissed a bucket.   When I came back upstairs I wondered if she was going to give me the “you seem like a nice guy” speech and nix the rest of the evening.

She didn’t.  I ordered myself a drink and we took a seat in a booth away from the noise.  She had a beer of her own but didn’t seem very interested in it.  We made chit-chat about nothing in particular, and I was surprised to detect an English accent despite her being Chinese.  But she grew up in Hong Kong, and studied and worked in the UK, so apparently that was why.

After about 10-15 minutes I asked, “Do you want to get out of here?”  She did and we got up to leave.  I knew she had a hotel a block away, but I insisted on meeting somewhere neutral in public first.  As we walked outside I was waiting her to change her mind and wish me good night (as is my luck), but instead she hooked her arm around mine, eventually hugging it with both of hers.  Oh!  Looks like she was interested after all.  She warned me beforehand that – despite her online sluttiness – she was likely to be awkward and shy in person.

To be sure, as we walked down the sidewalk she kept stopping to stare at me with a weird grin.  I kept asking her “What…?” and she kept asking me why I was giving her weird looks.  Uh, because YOU are.  After the third time I turned and put my hands on her waist, and she continued looking up at me with that weird grin.  This seemed like the moment.  I moved my hands up to cup her face and went in for the kiss, but at the last second she turned her head and I got her on the cheek.

Oof.  More awkward.  She wrapped her arms around me and buried her face in my shoulder.  Okay.  What’s the deal?  Well,  apparently she doesn’t kiss on the lips.  Okay there, Pretty Woman.  I didn’t get much more out of her than that, although she later confessed that kissing doesn’t do anything for her.  I didn’t know that was possible, but there are all types I guess.  Maybe the other guys she’s been with were bad kissers? Who knows.  And before we resumed our walk back to the hotel, she blurted, “I might even like you as a person.”

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“I don’t kiss on the mouth.”

“Well, I’d hope that you’d like me as a person.  I’m not just a piece of meat, you know.”  She let out a loud giggle and quickened her step until we were almost race-walking.  We went right into the elevator and up to her room.  She swiped her card and in we went, with me in a bit of a daze.  This was totally surreal.  Was this really happening?  Never in my wildest fantasies did I imagine something like this could be a reality.  And from my ridiculous online dating profile!

She was still a bit awkward, which was making me awkward.  I’d vaguely pictured myself making out with her and slowly removing her clothes piece by piece.  That kind of foreplay is important in helping me determine what someone likes.  But with kissing off the table, there went one of the tools in my toolbox, and it was a bit of a buzzkill as well.  Plus when I looked up from taking my shoes off she was already pants-less.  Somebody was eager to start, apparently.

There was a bit of fumbling about and then we were lying on the bed, first side by side and then me on top of her.  There was more awkward fumbling about as I tried touching her lady parts, but couldn’t seem to get that right.  First she told me to be more gentle, but then she was pressing my hand into her indicating I should use more force.  Then she put one of my fingers inside her, but after a minute of that she wanted my fingers on the outside again.  Finally I hit pay dirt when I started sucking and kissing on her neck and tits.  All girls seem to like that, but she was practically orgasming from it.

We were a bit limited in what we could do.  In addition to no kissing, there was no oral either – for her or for me.  So that basically left condom-only P-in-V sex.  She couldn’t wait any longer and wanted my dick inside her, but she didn’t think she was wet enough.  After leaking pussy juice profusely for an entire day, she was running a bit dry.  But I put on a condom and she slathered lube everywhere, and then we started fucking.  Finally, an area I seem to excel at.  At least, I’ve never gotten any complaints in that department.

She got really wet before long, and it felt so good being inside her.  (Skyn condoms are great, btw).  I’d already jerked off twice that day looking at the pics she sent me, so I lasted a decent amount of time before I unloaded in her.  It was really intense.  I don’t remember it feeling that intense with my ex Rebecca, but it’s been so long that it’s hard to remember exactly.  She came too – loudly – and it was funny because even though she sounded British she would orgasm in Chinese.   It was like I fucked her into another continent.

Afterwards we lay there for the longest time, just talking about stuff. She asked me a million questions, including, “Am I asking too many questions?”  She dropped a bomb about being divorced. She also claimed I’m the first person she’s had sex with in two and a half years.  Wow.  So she’s had a longer dry spell than I’ve had.  Who would’ve thought?

All the while we played with each other’s hands, stroked each other’s arms, and touched each other all over. I gave her a back and shoulder massage because I love doing that.  The entire time I did my best to relish every moment, telling myself that it might be a long time before I get to touch anyone like that again. Sure enough, I remember thinking that exact thing when I was with my ex, and then two years went by.

Eventually she started jerking me off, but it wasn’t doing anything for me. She didn’t have the right touch, even after I gave her some instruction. Then she was telling me to cum even though I was nowhere close, and her telling me that had the opposite effect.  It’s like when the doctor asks you to pee in a cup, and the more you try the more you can’t do it.  Then you start feeling pressure, and in this case I was starting to go soft.  She noticed and started making efforts to get me hard again, which also had the opposite effect.

Shit.  I went back to work on her neck and chest and soon I was almost rock hard again.  We had sex a second time, we both came again (her at least twice) and we managed to snag a couple hours of sleep before morning.  We tried some other positions but they weren’t really comfortable for either of us, so it was mostly missionary. There was one more round of equally satisfying sex before I had to hit the road.  It felt a bit weird waking up in the city, and I drove home in a bit of a daze.  That might have been more due to exhaustion, as I had to pull over and take a nap for an hour in order to make it the rest of the way.

I didn’t jerk off for the rest of the week.  We met for Round 2 the following weekend, and I wanted to save up an especially big load for her.  This time I met her right at the hotel.  She left a key at the front desk for me so I went upstairs and let myself in.

She was waiting in bed in a black lace negligee.  “John McCain died,” were her first words to me as I entered the room.  Wow, you really know how to turn a guy on.  But I did enter a celebrity death pool at the beginning of the year and he was on my list, so he earned me 24 points.  Yay for that, at least.

We got down to business right away.  I was more than ready for her.  I attacked her neck and chest and played with her pussy.  “How did you get so much better at this in only a week?” she gasped.  Easy – I simply remembered what she liked and didn’t like from last time.

Things went a lot smoother this time, and there was no need for lube whatsoever.  She was positively dripping downstairs.  She wasn’t kidding about that. I’d never seen anyone get wet like that – not that I have much experience to judge, though.

Finally she couldn’t take it anymore.  “Get a condom,” she gasped.  I did, and ten minutes later I filled that bad boy to near bursting after not jerking off for an entire week.  But truth be told, I didn’t need to jerk off.   After the previous weekend I found myself feeling fully sated and satisfied.  I didn’t even look at porn or anything.  However, I was ready and raring to go now.  She came many times, and after the third round of sex she took the baby oil I brought with me and dumped it everywhere.  She proceeded to massage my body with hers.  It was amazing, and she ended by jerking me off until I spurted a fourth time. Practically repainted the ceiling.

She wanted to keep going.  Unfortunately, the spirit was willing but the flesh was weak.  I was surprised and disappointed I couldn’t go more than four times.  Apparently sex is more intense and draining than regular ol’ masturbating.  We’d also been at it for five hours by that point.  And we were getting pretty hungry, so we got dressed and headed out to the diner.  She watched in amazement as I downed a plate of pancakes, a bowl of home fries, ham and eggs, and a bagel.  Apparently sex also whips up quite the appetite.

We held hands on the way there and back, which was really nice.  Honestly, I was almost as happy holding hands as I was to have sex again.  I miss that kind of touch and intimacy. We learned more about each other as we walked and talked, and I also learned that a lot of people leave books outside their homes in Brooklyn.  Apparently this is a thing they do there.  I suppose it’s a take-a-book, leave-a-book kind of thing.  Heh – maybe they should call it Booklyn.

We got frisky when we were back at the hotel again.  I was ready to go a fifth time, but exhaustion overpowered us and we fell asleep.  We did have one last glorious round of sex in the morning.  I woke up with her hands on my penis.  In fact, she could barely keep her hands off it all night – even on the way back from the diner.  She said she couldn’t resist squeezing it and that I had a really nice one.  Why thank you.  I think it’s rather swell too, if I may so myself.

And thus ends the best two weekends I’ve had in a long time, and certainly among the best ones I’ve ever had.  She was only in town for ten days and we made the most of her time here.  Now she’s back home.  There’s a possibility she may return in the future, but when that will be I have no idea.  In any case, my scratch has been itched and I’m feeling exceptional nowadays.