S.A.R.D. #16 – Kathrine

WARNINGI’m going to be discussing something of an adult nature. I am whipping this out as it comes to mind and I have thoughts that are raw and uncensored – I may or may not use vulgarity. Oh, and it may have tons of grammatical and spelling errors too (Oh, the horror!?!?!). This post is intended for mature audiences (i.e. ages 21+). Also, names have been changed to protect the not-so-innocent.


In my previous entries on the series discussing my Sexual And Relationship Development, I only discussed things that were only breaching the surface of my emotions regarding sex and relationships.  But, it would make sense for me to discuss those relationships that were serious and had a major impact on me.  Granted, I had dated girls previous to the relationship I’m about to discuss – I might have even called some of the girls I dated “girlfriends” – but up until this point, I had not had one serious relationship like I did with Kathrine (Kat). Without one doubt in my mind, the relationship I had with her was the first “real” relationship I had and, unfortunately, it really was doomed from the start – although neither one of us knew it. It was an intensely emotional relationship, but it was intensely sexual too. There were so many things we did with one another that I believe we both came into understanding our sexual interests together.  To say we were immature isn’t exactly accurate, it was more like we simply needed each other in a way that wasn’t healthy. You see, we began dating when both of our parents were undergoing divorces and, as a result, we began to try and fill the holes our parents left us with one another. I don’t believe she and I ever hated one another, but when the relationship began to unravel, we didn’t understand how to exit gracefully and there was plenty of hurt at the end.

We met while we were in high school, but we only joked around with one another when we were each in the groups of our friends. My friends and I would would tease her and her friends. Obviously, some of it was flirtatious and being upperclassmen (we were juniors and she and her friends were freshmen), we probably did it with a misplaced sense of pride. The teasing was returned. as well, and this continued through our high school years. I had become a little bit of a friend with Kat, because she had a couple of friends I ended up dating. She and I never dated in high school, but that would change the summer after my freshman year of college.

I happened to be hanging out at a local mall with a childhood friend of mine and she was walking through the mall with one of her friends from high-school. In high school, my friends and I had a sophomoric inside joke where we would tell a girl she “had a nice shirt” when were, in fact, saying she had a nice ass.  As we passed Kat and her friend in the mall, I looked at her with a grin and said, “Nice shirt”.  She stopped me and said something like, “You like my shirt, huh? Is that the only thing you like on me?”  Her flirtation was with a major grin and it sparked the conversation that would lead to us dating. We exchanged phone numbers after I asked her out on a date.

The dating was light, but quickly turned into something serious as we began to see each other more often and began having sex.  It’s kind of sad now, but I can’t remember the first time we had sex – I’m not sure if it’s because the amount of time that has passed or the fact that our sexual experiences didn’t remain benign by certain standards (although, admittedly, nowadays it may be considered fairly innocent). This summer between my freshman year of college and my sophomore year had also seen the start of her parents’ divorce. My parents would divorce a year later.

Even as I write this, I’m not sure I can fully express this relationship in a single post. There were so many things that occurred, that his post merely feels like an introduction that would need to be addressed in multiple posts. But this relationship contained a lot of emotional ups and downs as we looked for ways to support one another through our parents’ divorce. It had the ups and downs that occur in relationships as they develop over time. The relationship had times of jealousy, separation, times of arguing, times of pain, times of happiness, cheating (on her part, not mine…ahem!), and sex.

Oh my gawd, did it have some sex. There are so many sexual things we did together and discovered about one another over the course of our relationship. Without going into too much detail, I would say that we involved porn, toys, threesomes (2-mmf), pegging, crossdressing, truth and dare, spin the bottle, more sex, and so on and so forth.  To discuss everything in a single post would require so much time and room. We were together from the time I was 18 until I was about 23, but I ceased contact with Kat when I was about 24, a few months before meeting my wife.

It was a relationship that began with flirtatious teasing and ended with me, childishly expressing that I hoped she died of aids (side note: She’s fine, married to the guy she was living with while still fucking me at the end of our relationship)…

Needless to say, I’m not sure the breadth of this relationship can be expressed in a single post. With that being said, I haven’t decided if I will create a subtitle to S.A.R.D. and call it “Kat”, or simply reference “Kat” with a tag in subsequent posts.


9 thoughts on “S.A.R.D. #16 – Kathrine

  1. I can’t help but get the feeling that perhaps some regrets still cross your mind. It’s a bittersweet memory, with things you miss in your life now and things you might feel that never can be again. Both of you are not free, perhaps you have wondered if she thinks of your times the same that you do. I think that maybe there is something still raw about that time and writing about it could help come to terms.
    Big hug my princess.

    Liked by 1 person

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