How bad was your first time? (Mini-TR included)

[toohigh]

So my first time was like 2.5 yrs ago, and god was it awful. This thread doesn't make me feel too bad about it, but it still was a horrifying experience for me.

I had met this chick like 2 or 3 weeks before I closed the deal. I was at a strip club with the guys I was working with at a radio station. Our show had just got canceled, so we decided to hit up a strip club to take out our frustration.

The strippers were alright, but this one cocktail waitress was smoking. We chatted up for a bit, and I guess the fact that I was out of a job and drunk made me fearless, as I got her number and was spitting game to her like I was an expert PUA. Truth be told I still have ZERO game, but whatev.

So anyway, a couple of nights later, another DJ from the radio station I was working at wanted to set up a get-together on my dad's boat. Turns out he knew the cocktail waitress that I had met the other night (don't really remember if this was some strange coincidence or what, but looking back, the ho prollay just got around), and brought her along with some other peeps. When we recognized each other, the attraction level skyrocketed, and we were hooking up pretty much all night. Started off in the parents' bedroom of the boat, then continued in my car while we all went to some other strip club that night. No sex yet, but some serious making out/groping/dry-humping was going on. This was enough for me at the time, too, b/c I hadn't even hooked up with a chick before to the extent I was with this one. I was still totally clueless.

Things continued in a similar fashion, with a little bit of tension between us because she was 26 and I was 21 (didn't bother me but she kept bringing it up that we couldn't be serious b/c of this), until the day she took my virginity. We went out to some club to celebrate my birthday which was a few days passed. We all got trashed and had a pretty sweet time from what I remember. Then we head back to the boat at like 3am. Here was where the first problem happened on my sex-quest. Cocktail waitress had this step-brother, who was basically the world's biggest mooch. Totally dependent on her, and would basically tag along with her everywhere. Well this night was no different, so while I'm getting things going with cocktail waitress back in the bedroom on the boat, this guy barges in at least twice, complaining that he wanted to borrow my car so he could go home and pass out. F that, I'm not letting some random, drunk [censored] drive my car over 30 minutes. Cocktail waitress and I try to ignore him, and she keeps complaining about what a pain in the ass he is, probably cuz he was the only person not getting any out of everyone we were with that night. Just totally awkward all around.

The next problem occurred for me during the act. Like many others in this thread, I just couldn't really get my mojo going, and was all but limp for 90% of the entire experience. This was caused by my complete amateur status when it comes to sexytime, severe performance anxiety, combined with being pretty drunk and really stoned, and still steaming from her step-bro barging in every 5 minutes. My mind at this point is racing in a million different directions, part of me completely stoked that I'm finally sexing, and with a hot, hot, hot chick, and the rest of me just completely confused and frustrated. When I finally got it going, I was doing her missionary, and the [censored] bitch says "I want you to come inside of me, be a daddy!" over and over (she already had 2 kids, lol). Ughhh, this really ruined the mood for me, but I was determined to at least get off somewhere on her body, just not inside.

We try every position, [censored] I couldn't even get it in doggy style cuz it was too limp. It was just a complete disaster. Half the time I had a condom on, which really shrinked my package, and it slipped off like twice, so we were both like "F it" and I just rawdogged it the rest of the way. We even took a break, and I called the captain of the boat at like 8am to take us all for a ride. During the ride, we went back down to the bedroom to try again, and she was riding me while the boat was getting bumpy cuz of all the waves, and she was enjoying it thoroughly, but I still couldn't finish. ARGGH, so annoying.

Eventually I guess we just gave up, I remember her saying something like "you must not want me" and me just laying face down in the bed with my head buried in a pillow cuz I was so ashamed.

And to make the whole experience even more [censored], I got a [censored] staph infection (that's what the dermatologist called it) from the dirty ho on my groin area. Thank god it wasn't teh herp, but it still hurt like hell and was just gross and took like a month to go away. Talk about running bad at sex...

This experience left me with absolutely zero confidence with women, and still haunts me til this day. Thankfully, the one positive I did learn from this was not to blow crazy amounts of money on chicks (I spent like 2-3k with this girl between me buying her stuff, going to see her where she worked and blowing mad money there, and taking her out to clubs and dinners). Now I am stuck with a mentality of being as cheap as possible when it comes to women, where I feel like it's not my lack of confidence that has been hurting my game, but the fact that I simply would rather save my money than spend it on a chick.