The Last Girlfriend (Part 2)

Continuing from my last post, this is the story of my (so far) one and only long-term relationship.  This happened when I was 17-18.  


When I got to Patti’s house I stopped on the sidewalk outside. The light was on in the living room and I knew she was on the computer as always. Her mother’s car was gone from the driveway; she was working late again. I paced outside for a bit, screwing up my courage and rehearsing what I would say. When I was ready, I ran up to the front door and knocked. As soon as I did I forgot all my lines. She opened the door, surprised to see me there at such a late hour and with a trace of concern on her face.

“Hey – what’s up?”

“Uh…can we talk?” As soon as I said that a flicker passed over her face. She must have known what was coming.

She came out and we sat on the front steps, since I wasn’t allowed inside when her mother wasn’t home. In a few minutes it won’t be an issue anymore, I thought.  The night air was crisp and cold since it was only the middle of March. After a few awkwardly silent moments, I cleared my throat.

“I don’t think this is going to work out,” I said.  She looked down at the ground and nodded. I knew she was thinking along the same lines, and mostly for the same reasons, even though she didn’t say anything.  I was going to miss that – the fact that our minds were so much on the same plane that we usually knew what the other was thinking.

But while we were so alike, we were also very different. And we were on different paths in life. We were going away to school in different states. And even if I had a strong enough desire to continue the relationship, I couldn’t have. Some people can have long-distance relationships. I can’t. I need that person here in my life, not hundreds of miles away, only to be seen for a few weeks during the year, without physical contact for long periods of time in between.

Not that there was much physical contact to begin with.  We were both virgins and progress was frustratingly incremental.  It was two months before she stopped freaking if I put my hand on her neck while we made out.  The first time I did that she pulled away and curled into a ball and started shaking.  Um, what?  I poked her and asked what was wrong.  “Usually when a guy does that, it means he wants something more.”

She finally confessed that she was making out with her ex boyfriend once and he touched her breast.  I waited, but apparently that was the whole story.  It took her a while to recover.

Three months in she was okay with ass grabbing.  Four months in – and this was a big day for me – she finally allowed me to touch her breasts.  Through her shirt.  It was a few weeks after I’d turned 18.

After eight months of dating she graduated to groping me in return – but only through my pants.  She dabbled with slipping her fingertips under the waistband of my jeans but wouldn’t go further than that.  Her reason?  “Well, if you came while I was touching you and it got on my hands, and then I touched myself down there and there was liquid seeping out of me, there’s a very small chance I could get pregnant.”

After a whole year of dating she felt comfortable enough to put her hand all the way down inside my pants – sometimes even pulling my penis out to squeeze it or run her fingers along it.  Only for brief moments, though.  Every time we fooled around she’d get me all hot and bothered, and then she’d pull away and we’d have to stop because she was afraid of going too far.

Whenever Patti was at my house I’d have to coax her over the threshold like a nervous stray cat.  She was scared that my neighbors would see her going inside and tell my dad who would in turn tell her mom.  *eye roll*  This wasn’t 1955.  This was 2002.  Not only did we not talk to our neighbors, we avoided eye contact if we went to the mailbox at the same time.  They didn’t give a fuck if I had a girl over.

Her fears weren’t without merit, though.  One day Dad came home early and nearly caught us fooling around.  We took shelter in a closet until the coast was clear. Dad had ladled out enough Catholic guilt over the years and I didn’t need any more helpings.  And Patti was a nervous wreck when we were at her house.  Every 30-60 seconds she’d race to the window in a panic thinking her mother’s car was pulling into the driveway.

However, one day we started getting really hot and heavy.  Shirts came off.  Her bra came off.  Then she took me by the hand and led me downstairs to the bed in the basement.  Holy shit, after a year and a half this was finally it!  We lay down on the bed and continued making out, but after a minute I saw the familiar look in her eyes.  She was getting spooked again.  Sigh.  So I suggested she gave me a hand job.  Or a blow job.

Soon I began wishing I hadn’t.  She didn’t seem to have any clue what she was doing. She moved my dick around like it was a joystick (I know… it is).  She rubbed it between her hands like a Boy Scout trying to start a fire with a stick.  She blew on it.  No, she didn’t blow me.  I mean she literally blew air at it.  Then she squeezed it so tightly that the head turned purple and I was waiting for it to explode and confetti fly everywhere.

This went on for about ten or fifteen minutes. Finally I couldn’t take it anymore.

“All right, stop.”

She let go of me.  Phew.  “What’s wrong?”

“That’s not how you jerk a guy off,” I said, trying to hide my exasperation.

“Show me, then,” she said, sitting back on her heels and folding her hands in her lap.

So I did. I sat up on the bed, jerking off in front of her with my tighty-whiteys around my knees.  And she just sat there looking at me.  The whole time I just kept thinking to myself:  this sucks… this really sucks… I could be doing this at home…

“Okay,” she interrupted. “Let me do it now.”  And she took my dick in her hands and started over.

Five minutes later she was still at it. “Nothing’s happening,” I said pointedly.

“Well, it’s getting really hot…” she observed. Yeah, because it’s getting really pissed off, I thought.  I wrapped her hands around my dick with my hands and moved them up and down to give her the idea.  She still wasn’t quite getting it, and it definitely wasn’t doing anything for me.  Finally I’d had enough.  I pulled my clothes back on and said I had to go.  Then I went home and finished myself off.

I thought about what to do next.  Over time the spark had faded between us and it felt like we were just going through the motions.  Our late night chats were rare and conversation was dwindling.  All we had left was fooling around, but it was proving to be frustrating and unsatisfying.  So three days after President Bush started dropping bombs on Iraq, I walked back over to Patti’s house and dropped a bomb on her too.

She took it well at first, and then broke down in tears.  And that was that.  She moved on to date (and have sex with) other guys. Then she later dropped a bomb of her own:

She was gay.

Except… she still liked guys.

So she was a gay man trapped in a girl’s body.  She eventually moved to Canada, had all her equipment changed over, and began her new life as Paddy, aka The Boy Formerly Known as Patti.  And that’s the last I ever saw or heard of her.

After I dumped her, I started feeling ashamed of myself.  Did I really break up with her because I couldn’t get sex from her?  What a horrible thing to do.  I remembered how I always had to initiate fooling around or making out.  Nearly every single time.  While she would reciprocate and get into it, she almost never made the first move.  I started feeling like a monster as I reflected upon that fact.

For a couple of years I felt like I didn’t deserve to be with another girl, lest I treat her like a piece of meat too.  I spent half of my 20s looking for someone, and the other half not looking and not caring if I ever did.  But I didn’t go on another date for at least ten years.  I was year into this blog when I finally dated again.  30 was looming uncomfortably large on the horizon.  I didn’t want to be a 30-year-old virgin, but 31 proved to be the magic number.  Perhaps blogging is what helped me succeed.

Anyway, now you have the whole story.





8 thoughts on “The Last Girlfriend (Part 2)

  1. By how she acted that girl (or guy I suppose) seems like she had issues. Her extreme reactions to you touching her on her neck and then changing her gender later, something happened to her mentally.

    • *shrug* Who knows. I do know something happened with her dad. He died when she was very young and the official story was “heart attack” but she thinks he was secretly gay and actually died from AIDS, but nobody in the family wanted to talk about it. And the weird thing is, I saw a picture of her after the sex change and she looks exactly like her dad now.

  2. This is a really sad story in so many ways. Sad that Patti was so emotionally fucked up that she couldn’t appreciate or wasn’t ready for a physical connection with another person. Sad that she treated you so badly (yes, playing with your developing sexuality is treating you badly – you were not a wind-up toy and you at least deserved some kind of physical relationship, even if it was mutually discussed and agreed where the boundaries were. Sad because of all the lecturing, posturing and blackmail by both your families about sex and pleasure. Sad because she was obviously a troubled soul whose identity was being questioned. Her reaction to the spectrum of sexuality was, frankly, absurd and bizarre. Touching necks is not a sign of ‘things getting too heavy’ and as for breast touching, waiting a year for that is incredible. Overall, I am glad you made that decision and I’m sorry this happened to you. Thanks for sharing.

    • To be fair I wouldn’t blame her for treating me badly or anything. We were both clueless virgins and had no idea what we were doing. I thought waiting that long to do that stuff was normal, I didn’t know. And I sure as hell didn’t do anything to please her or get her off apart from making out and rubbing her tits. Not to mention I had my own fears and hangups about sex. Looking back I’m kinda glad we didn’t go all the way, because I don’t think I was emotionally or mentally mature enough to handle that at 17 or 18.

      Also with the neck thing, I just remembered another story she told me at the time. She was making out with a guy on the bus during a school field trip and he put his hand on her neck, and then his hand started straying down. So between that and the ex bf story, it was enough to give her unpleasant flashbacks.

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