My First Job & My First Girlfriend

At my first job I worked for the company for many years and was the youngest person with the most experience. This meant that I worked directly with employees from all over the company up to and including executives as I possessed knowledge and experience about nearly every aspect of the company’s operations. This put me in a unique position within the company. I was well liked and respected by nearly everyone.  I was on e-mail lists and had access to systems that were well above my pay grade.

I was successful at work, but my love life was the opposite.  I had graduated high school without so much as asking a girl for her number or asking a girl out on a date.  I was a real late bloomer which didn’t help, but at the root of it all, I just didn’t think girls were into me.  I had a HUGE fear of rejection.  HUGE.  It was paralyzing.  It also didn’t help that I had always commuted to nearly all of my schools, which meant that I never really got the social experience of being able to easily meet and hang out with groups of friends from school.  You know those group projects most people hated?  I relished them because it gave me social interaction with friends away from school.

My first girlfriend kind of fell into my lap.  Through a guy at work who attended one of the larger, well known colleges in the area, I got hooked up with a lanparty college club.  Now, this coworker headed the group, but one of his close allies was a high school kid who was the son of the Dean of Computer Science.  This was important because it meant that the lanparty group had near carte blanche with regard to running their events within the campus buildings.  This meant that when we had events we would have a place to take over and call our own that was huge and we could be as loud as we wanted in.

The son of the Dean would have a number of his friends come to the lanparties and since I provided equipment from my workplace (due to my position within the company, I just told them I was taking equipment and nobody blinked an eye) I soon became close with him and his group of friends.  Within this group there were a few girls.  Some of them attractive.  One, was gorgeous.  We’ll call her Strawberry.  Strawberry was half japanese, half portuguese, so she had that beautiful asian skin (but with some color), long gorgeous dark hair, athletic build, and an ass (rare for an asian girl).  Strawberry had this smile that always seemed to be around, she just had this  carefree positivity, and was genuinely caring.

Like this, but hotter than Olivia Munn:

I enjoyed being around Strawberry at the lanparties, but because I doubted that she could be into me I waffled between actively seeking her out to be around her at the events (and laughing/flirting with her) and ignoring her and going off to do my own thing (sometimes without anyone else in the group).   As I became closer with the Dean’s son, I found out that she wasn’t romantically linked to anyone, although he had pined for her for a long time (although he had already had attempts with her and she had denied them).  I started to hang out with him and met his parents who were both very nice people.

They must’ve seen something in me as when they all left on a family trip out of state for over a week they asked if I would please house-sit for them. Keep in mind that I was just out of high school and that their son was still in.  I wasn’t that much older than their son and they had only met me maybe twice before this.  Their house was back behind the college and was worth well over a million dollars.  House-sitting for them was a huge upgrade for me and on top of it I’d be much closer to work and also in the same area as the Dean’s Son’s friends (many of whom I’d become close enough to that we might hang out while I was house-sitting).  I of course said that I would house sit for them.  I had no idea they were going to pay me.  They paid me a handsome sum at the time and I was flabbergasted.  I mean, to me all I had to do was walk the dog (fun), feed the reptile (easy), and make sure the house wasn’t a complete wreck.  Heck, they even said I could have our mutual friends over and to please eat as much as I wanted from the pantry/kitchen so it wouldn’t go bad.  And they were paying me to live in their near mansion?  This was nearly beyond belief.

I lived the good life.  I met up with the Dean’s Son’s friends for coed football games right after work, hung out with them at night in the same neighborhood playing Sardines, and all kinds of great fun.  At some point I think I invited a smaller group to come over and watch a movie at the Dean’s place.  This was exciting for me as Strawberry was supposed to be there.  I remember getting all excited and then trying to play it cool during the movie.  She showed up with her male BFF and nobody else.  It was fun, not awkward, and I wouldn’t even mention it except that it led to her and I talking on the phone quite a bit.  The Dean’s son’s room phone (yes he had his own phone line in his room) while I laid in his bed.  We talked so much one time that I knew it was now or never if I was going to ask her out, so I did.

I can’t even remember what I asked her out for.  I think it was either ice cream or dinner.  It doesn’t really matter, because I did it.  I forced the words out of my mouth and she enthusiastically agreed.  I was elated.  I was in heaven.  I had oneitis.  Luckily, she had it too.  Throughout the whole time she had been interested in me, but wasn’t sure that I liked her.  My attempts to not overdo my own interest so as not have my interest in her be exposed (in embarassment I had been sure) probably had made her even more interested in me.  It was pretty obvious from our first date on that she and I were VERY into each other.  I probably held her hand in a movie theater and all kinds of total cheesy rom-com type stuff, but when you are both so into each other, that stuff is fun.  I felt like I had won the lottery.  I had by far the hottest, coolest, smartest girl in the group.  The Dean’s Son luckily was actually a genuinely good guy and didn’t slight me for dating his friend that he had previously pined for.

I spent MANY a night taking this girl out and bringing her back before her curfew.  We watched movies, we went to dinner, we walked in parks, we did just about anything, it didn’t really matter.  Her friends got along with me and I got along with them.  I’d go with the other boyfriends to watch their volleyball matches and even eventually attended my first prom (hers).  I’d get her flowers sometimes at random, she’d write me little love notes and make things for me.  I’d eat dinner semi-regularly with her family, her dad loved me, her mom was polite but guarded and a little harsh towards me (I mean, I was the guy not in high school dating her 16-17 year old).  Year’s later her mom apologized profusely for being such a bitch towards me (her words, not mine).  It was awesome, I can’t lie.  That lasted nearly 2 years, until just before she took off for college.

I never fucked her, because we were both virgins when we met.  I wasn’t sure that I was ready, and she wasn’t sure she was, so we mutually agreed not to.  And really I felt that way at the time.  The only regret I have about it is that I might’ve kept her as a girlfriend if I had fucked her.  Of course, there’s no way to know that, but I know now that if I’d escalated it, I’m sure she would’ve wanted to.  Fortunately, she was perfectly happy to give me oral sex and I was perfectly happy to give her the same.  In fact, her pussy tasted like strawberries.  Always.  If I hadn’t been there I might not believe it, but she did.  She became really good at getting me off and I became really good at getting her off.  She could have multiple orgasms and I had no problems going again after a quick break.  She was that hot, that most of the time when I wasn’t even sure I could get hard again, she could make it happen.

It was pretty damn blissful.  I’m either cursed or blessed as this set me up for a pretty high standard with girls I’d date.  It definitely left me pretty frustrated after I’d had another girlfriend fall into my lap after Strawberry who was also attractive and intelligent.  After my second girlfriend I was left having never really asked a girl out (without knowing her for a long time beforehand) and having never asked for a girl’s number.  I still had a huge fear of rejection, I just had more confidence in the situation of already having a girlfriend, not how to get one.  Soon after my second girlfriend and I broke up, I moved to the beach.  I ended up living in a place and building a social network where it was pretty difficult for people to understand that I had a huge fear of rejection and didn’t have hardly any experience with pursuing girls.

It’s actually pretty funny now that I look back on it.  My nerdy computer startup coworkers thought that I was the fucking man with women because I had two girlfriends while working there that were by far hotter than anything anyone in the company had dated, but in reality I had next to no skill with opening/talking to/closing girls.

Thus started my journey.  Two sort of notches under my belt, but no knowledge/experience to go hunting with.  I needed some kung fu.


~ by aneroidocean on 03/28/2012.

2 Responses to “My First Job & My First Girlfriend”

  1. She’s really pretty. If your first gf was really that pretty, way to go guy!

  2. I have had a similar situation. I would argue that she didn’t raise the bar so much as let you know what good was.

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