Sex and the City, Part I

I grew up in a pretty big city that embraces diversity of all types. I have since realized that it was probably the best place I could have been raised, considering how different I am from the mainstream in many ways, to have that accepted and encouraged by others. Also, being the distinctly curious sexual being that I am, my city was one of the best places to be, in that there were plenty of opportunities to observe, explore, and to try out new things. One thing I've always liked about my city is that you can find just about anything you're looking for. That and the fact that freakishness is not only accepted, but it's encouraged in a sense. That is my kind of place!

Before the internet became mainstream, before the Web, I discovered a local chat network (XX Net -- 'XX' being the city name) that had terminals in local coffeeshops all over the city. I had read about the internet and thought it was so cool, so when one of the Net machines cropped up in a neighborhood coffee house, I jumped on it. XX Net was a local BBS that focused less on message boards and games, as most of the other BBS's did, and far more on chatting. It connected some of the funniest, most intelligent people in the city and I was enthralled. Soon, I was hooked and scrounging up my allowance to buy a modem so I could log in from home. To give you a time frame, I was 15 and so excited to find a used 14.4k modem because it was top-of-the-line and the fastest speed available. Kind of funny now, right?

I made a ton of friends via XX Net, which rescued me from the social black hole that was my 75-student private school (there were maybe a dozen people in my entire class). Over the next few years, I was a regular. I engaged in a lot of different social activities like hanging out and going to 'Net-Gets', parties, and bonfires. Most of the sexual experiences I had during this time were somehow related to XX Net.

I consider myself as actually having lost my virginity at 18, but the truth is that I had tried to have sex a few times before that. None of the first times worked because the guys could enter me, but only part of the way. It was like they were being physically blocked and it really hurt when, thinking they just needed to break through, they tried to proceed anyway. After a few similar experiences, I saw a doctor because I thought I had a hymen of steel, but it turned out my hymen was fine. I had a psychological condition that caused me to tighten my vaginal muscles like crazy, preventing penetration, because I was so nervous.

In any case, I went through a slew of random sexual encounters at this time. I fooled around with guys I didn't know very well, and because I had no real intention of losing my virginity to them, I gave more head than I care to remember. The first time I tried to have sex was with a man who was married and practically separated from his wife. He was probably in his late 20's and we were both attracted to each other, so we ended up in a somewhat seedy hotel. We had some drinks and made out, but for the reason above, sex ended up being a no go.

The next guy was someone I'd met at a festival and our drunken attempt at coupling in his tent was once more somewhat of a failure for the same reason. Though I will never forget his answer to the problem: to lean back and try to ram it inside me with a great deal of force, but missing, and instead ending up ramming his cock in my ass.. totally unprepared, unlubed, etc.. all I can say is MOTHERFUCKING OW. Aaaaand that was pretty much the end of that.

The next guy was Bryan, a guy I was dating and whom I really liked. He was a sweet guy. He lived about 30-45 minutes away, so after one date that ran late, I invited him to stay over. We ended up making out and as things got more hot and heavy, he told me that he was a virgin. We tried to have sex, same deal.. no go. I was at the peak of dealing with my sexuality and ended up breaking up with him not long after because I was all freaked out.

Later on that year, I ended up successfully having sex with Jeremy. He and I were close friends and I felt very comfortable with him. There was never any pressure to have sex, other than from my end, and though I had a bit of a crush on him, no chance for a relationship. He'd had his heart broken by some bitch that had treated him like shit and he was still healing. It ended up being the perfect situation. Because I was left to boil in my own arousal, I was totally ready to have sex with him. I was relaxed, very turned on, and I trusted him implicitly. Amazingly, this time, things fell into place. He entered me easily, slid past my hymen, and right into fucking me. Even better was that it only hurt a little and for a short time in the very beginning, and right away it all felt so good and enjoyable. I ended up being quite glad that things had worked out this way and that he was the guy that deflowered me.

Anyway, all of this is a bit of backstory leading up to a story I want to retell.. Part II will be the details of the orgy I attended in my city at age 18.