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.

23 thoughts on “So… I Had a Girlfriend

  1. Paddles, handcuffs, blindfolds….Holy Moses how vanilla…At least you didn’t take too many ideas from Kink.com.

    Although I’m glad you talked about a relatively long term relationship and explains your latest break.

  2. I’m so happy for you, but sad as well. These things are bittersweet. The important thing is that you lived in the moment and appreciated the time you had together. Lots of memorable moments and experiences by the sound of it!

  3. Dude. This is great. Nice to do it dozens of times with someone. Kick ass. Well done.

    Yeah being swallowed is awesome especially when they keep going a few minutes more. Crazy sensitive

  4. Loved reading this journey. It’s good your upfront about not having kids. I was the same way and thankfully I found someone who was just as adamant about it as I am. You’ll find someone as well. All women don’t want kids. I can attest to that.

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