So… I Had a Girlfriend

It’s been a while.  The last time I was here, I had a handful of Hinge matches that weren’t really doing anything for me.  I decided to junk the app.  However, one of the girls I was talking to noticed I was gone and panicked.  She messaged me on Instagram (slid into my DMs, as the kids say) and was suddenly a lot more conversational.  Well, this was more like it!  We went on our first date a few days later.

#62

Dawn, 28, a teacher and a local!  She lived only a few miles away, and coincidentally on a road I frequently traverse.  We met a local pub halfway between our houses.  I normally detest meeting in bars and such, but it was a Monday and mercifully quiet.  We got on pretty well, and as I walked her to her car afterwards I saw it was conveniently parked right next to mine.  I took that as a good sign.

We stood there for a moment looking at each other before she giggled and said, “I always get awkward at this part, I never know what to do!”

“I do,” I said and I took her in my arms and kissed her.  We made out for several minutes, ignoring the soft light rain that had developed.  She told me I was good kisser, and she wasn’t afraid to use her teeth and bite my lips a little.  Ooh, a biter!  Does that mean she liked it rough?  The thought got me super hard.  There was definitely going to be a second date.

We went to a mac and cheese place for our second date, and across the street for brews and board games afterwards.  However it was chilly inside and rainy and damp outside – much like our first date – so I suggested going back to my place where it was warmer.  I worried she might take it the wrong way and question my intentions.  Fortunately she was down for it, and we watched a movie and had a makeout session afterwards.  But we didn’t go further than second base.  It was only the second date and she didn’t want to rush things.

Third date was lunch and a hike, fourth date was dinner, and fifth date was dinner at my place.  I’d always wanted to cook dinner for someone and I finally got  my chance.  I thought she might stay the night but she left at 11:30.  Before she left there was some making out, some clothes came off, and my dick went into her mouth.  I couldn’t cum though.  I very nearly did, but I got some weird mental block and just couldn’t bring myself to do it.  What the hell.  And still no sex because now she was on her period.  Didn’t bother me but apparently some women are icky about that sort of thing.

Sixth date was pizza and board games, again at my place. She brought her Chrome firestick and we watched the Zac Efron Ted Bundy movie on Netflix. It was very good. Afterwards we cuddled and kissed a little bit, but I held back because I didn’t want to get too worked up and develop blue balls. She was still spotting from her epically long period (her gyno said it was due to her switching birth control pills), but eventually I said “fuck it” and starting making out with her for real.

Eventually she kissed her way down and gave me a blowjob. This time I came in her mouth, and she swallowed.   Holy fucking shit.  It felt amazing and took me a while to recover from that.  She was the second girl to ever go down on me and the first to go all the way with it.  Definitely worth the 34-year wait.  This girl was definitely a keeper. Even better, I awoke to the good news that her period seemed to be over!  Did I want to try having sex?  Pfft.  You don’t have to ask  me twice.  I grabbed a condom and when it was over I had filled that thing to near bursting.  Phew.

Over the next few months we had some great sex.  I lost count of the number of times we did it, but it was certainly in the dozens.  She had the most voracious appetite of anyone yet. One night she came over to my place wearing nothing but a trenchcoat over some sexy lingerie.  That was one of my hottest encounters ever.  We even experimented with paddles, handcuffs and blindfolds – more bucket list items for me.  There was good orgasm equality and we often climaxed simultaneously or close to it.  I scored some more blowjobs and happily returned the favor.  Dawn was only the second chick to ever let me go down on her, so it was nice to get some more practice.

Dawn helped me cross a lot of firsts off my list.  I finally had someone to introduce to family and friends.  I went on my first ever double date.  I updated my Facebook to “in a relationship.”  She joined me in the gym and we worked out together.  We watched a fireworks display.  I posted my first ever #wcw.  And then just regular couples stuff I’ve long relished the chance to do.  It was so nice to have someone to talk and text with all the time, sharing every weird or random thought.  Sometimes I’d wake up and just watch her sleeping next to me, scarcely daring to believe my luck.

So what happened?  Everything was going great as we approached the five-month mark, until I got the dreaded “we have to talk.”  Turns out… she did want kids after all. In the beginning she said she didn’t want kids, but ended up changing her mind.  I was afraid that was going to happen.  She was a Pre-K teacher, and anyone who teaches kids likes kids, and anyone who likes kids usually wants kids.  And if they want kids, then they have no future with me.  Dawn was looking towards the future, so that put the kibosh on things.  At least that was the reason she gave. I have no reason not to believe her, so I’ll accept that.

In the end I was dumped but at least we parted ways amicably and I have nothing but happy memories.  I gave the relationship everything I had.  Nothing was left undone or unsaid and I have no regrets.  Disappointing to say the least, when she checked off so many boxes for me. And five months – that’s a new record for me. 

All the girls I’ve had success with were fellow Sagittarius.  I don’t put much stock in that sort of thing, but it’s funny how it’s happened that way.  We certainly had a lot in common. Dawn was a brunette, which is also in keeping with the pattern…even if she did go blonde for the summer.  They’ve also been trending younger: 39, 37, then 34, and now 28.  Younger seems to be better in my experience.  More fun and spontaneity, less baggage, and greater sexual energy and openness.

While I’m sad that my time with Dawn has come to an end, I’m also kind of excited to see what’s next.  But I don’t know if I could go back to online dating.  (Of course, I keep saying that…) Even with that as a tool, it takes an average of 1-2 years to find someone interested in me in return, expending a great deal of time and energy in the process.  We’ll see.

Kiss

It’s been ages since I’ve had a second date, but I went on one tonight with The Singer and I dare say it went pretty well.  The original plan was to go to the carnival, but the shitty weather put the kibosh on that.  We ended up going bowling instead.  There was an hour-long wait for a lane so we went into the bar area and had a couple of beers in the meantime.

We found a relatively quiet corner and had a nice conversation.  I found out that not only does she like Harry Potter, but she’s a Star Wars and Titanic buff too.  Score!  She’s very easy to talk to, and the huge mug of beer I had helped as well.  We also delved a little deeper this time, broaching the subjects of religion and politics and the cosmos.  We were pretty much on the same wavelength there too.  She took a lively interest in what I was saying and I was eager to learn more about her in return.

They finally called our names and we went out and bowled a couple of games.  She picked up the tab for those since I bought beers this time and dinner last time.  I appreciated the gesture.  After a couple of good frames I did a spin and a moonwalk, much to her amusement.  When we were done bowling we sat there chit-chatting for a bit before calling it a night.  She had choir practice in the morning and it was getting late.  I also didn’t want to overdo things.

I walked her to her car.  At this point my heart was throwing itself against my ribs.  We’d been texting all week and things got a little flirty the day before.  I was determined to kiss her before we parted ways.  I think she might have wanted me to kiss her after our first date, and I wasn’t going to make the mistake of not doing so this time.  Second date – shit or get off the pot.

We stood by her car making idle chit chat and it was clear she was lingering, so it was now or never.  I said good night and we hugged.  We pulled back a bit, and then I lowered my arms to around her waist and pulled her back in.  She realized I was going in for the kiss and she closed her eyes and tilted her face to meet mine.

As soon as I saw her do that I mentally shouted YES! YES! YES!  Then we connected.  It felt great.  Totally natural and not awkward in the slightest.  I let my hands roam around a bit, running them up and down her back, along her sides, and then reaching up and grabbing the back of her neck.  She pulled me closer against her, and when I put my hand on her neck she grabbed the back of my head and pulled me even closer.  We made out like that for at least a couple of minutes before finally coming up for air.  She opened her eyes slowly and let out a little giggle as she looked me, and then she put her head on my shoulder and just held onto me for a bit.

I said good night again and told her what a nice time I had, and she told me I’m a lot of fun to be with.  Then I said I’d be in touch very soon, gave her one last peck and floated over to my car.  I drove home in a happy little daze.  And now the big question is how to proceed from here.  I’m quickly approaching uncharted territory.  I have to figure out my next move and not screw this up.  I seem to be doing pretty well so far, though.  I’ve been cool and chill and patient, and I haven’t done or said anything weird or stupid.

Oh yeah – and I think she likes me.

 

First dates:  34
Second dates:  4
Third dates:  2
Cancellations:  9
Stood up:  2
First kisses: 3

Lips

I was nervous about meeting Shorty, more so than any other girl I’ve met thus far.  It didn’t help that the evening was off to an inauspicious start and I hadn’t even arrived yet.  Instead I was stuck in traffic.  I ditched the highway for the service road, which was only marginally better.  Finally I passed the source of congestion: there was an accident.  In the shoulder.  All three lanes of traffic were clear, but everybody – including those on the service road – had to stop and look.  Why?  Because people are stupid and that’s what they do, no matter how long I laid into the horn to express my displeasure.

Once I got back on the highway I did my best to make double time.  Unfortunately I ran into another rolling roadblock, i.e. a driver from Virginia.  Every driver from Virginia that comes to NY decides to get in the left lane and go 60.  Tip: when you’re in NY, don’t get in the left lane and go 60 when the speed limit is 55.  You either go 75-80 or you GTFO of the way.

At some point during all this hubbub I managed to call Shorty and tell her I was running late and why.  Thankfully she was understanding.  I only got there 15 minutes late.  She met me outside and we hugged.  First non hand-shaker in a while.  However my physical attraction to her was a bit “meh.”  Nonetheless I had resolved to give her a chance.  That was despite the fact that she was such a fussbucket trying to find an appropriate restaurant to go to.  She Googled every one of my suggestions and changed her mind every time she offered one of her own.  Sheesh.

Anyway. We were seated, we were wined and dined, and between my glass of red and the three hours of sleep the night before (too keyed up) I was getting rather silly.  Enter offensive jokes.  Fortunately she was of the same mind I was, and not only that but she was the first girl I’ve met that didn’t want kids either.  Home run!  Score!  Schwing!  There were a couple of things during our conversation that gave me pause, but more on that later.

Dinner was over, and afterwards we somehow ended up at a Starbucks.  Sigh.  Even though I’ve sworn them off, they still seem to find me.  And even though we’d been together for two hours at this point (JBlondie, take note), we were still a bit nervous and awkward around each other.  It was also getting a bit late so I suggested that I walk her to her car.  Smooth.

Soon we were standing next to her car, and I shuffled my feet a bit and asked whether I could kiss her.  Indeed I could.  So I grabbed her and pulled her close and we kissed.  And kissed.  And kissed some more.  She tossed her pumpkin crappuchino or whatever the hell it was so she could grip me better, and I heard it splatter somewhere in the parking lot.   Our vertical wrestling match went on for several minutes until we finally ended it and said good night.

It was a bit… underwhelming.  I dunno, it felt like I was kissing myself, I don’t know how to describe it.  But she just about told me that things are only going to get more physical from here on out.  So needless to say, we’re going on a second date.

First dates:  19
Second dates:  1
Third dates:  1
Cancellations:  3
Stood up:  2
First kisses: 1
Sexual experiences:  0.5