Indiscretions of [m]y youth: Her best [f]riend

As with some of my prior tales of my youth I'll give you a quick heads up about me. At this point in my life I was twenty, I was in college, things were looking good, and generally, I was pretty happy. I was working and had a pretty decent paying job (for that time), school was a little jumbled, but I was getting through it, and on the sex side of things, I was doing pretty damn well.

I got into a relationship with a co-worker. It started off with just sex, as per usual drunk sex, but it developed into a relationship later on. During the first month or so of relations, something odd happened…

The beginning…

Indiscretions of [m]y youth: [F]irst time trying anal.

As with all of my tales of the transgressions of my past, I'd like to start off with a little bit about me. At this point in my life I was 18 years old and was probably in the best shape I'll ever be in. I had just finished playing football, and was still weightlifting and playing other sports for fun. At 5'10 and 170 lbs. I was solid and muscular. For those who care about cock size, I was nothing impressive, just an average 5.5". I didn't get a lot of girls while in high school, random hook-ups mostly and a few relationships that lasted about 2 years combined. However, as I was getting into my final year of school things started to pick up, a bit. This particular story is about the first time that I got to have anal sex. Bit long, but I have broken it up for you.

The beginning…

Indescretions of [m]y youth: [f]ast and furious

For those who read my last post, you know a little about me. I was stupid and brash when I was young. I posted last time that I drove drunk, but at least the story turned out well. Sadly, I must confess, that there was another instance of this completely irresponsible, and dangerous conduct. Again, I have changed the names for privacy reasons of all parties involved. Also, another long read.

The background….

As I mentioned before there was a bar in my hometown that was ridiculously easy to get into and drink at. For this reason a slew of people all under the legal drinking age would regularly attend this bar. To be fair, they never really admitted underage individuals below the age of 18, but that's not to say it probably didn't happen.

Anyway, on one fateful night in my nineteenth year of life, I went to this club with one of my really good buds. This guy was money to take with you. He picked up the hottest girls and lots of them. He wasn't exactly god's gift to women, but he was superiorly confident. The game was strong with this one. I was his Goose, and I knew my role in this duo; play as wingman and go for the girls that his choice was with. This had worked in my favor a few times.

Indiscretions of [m]y youth with a [f]riend’s mom

Sorry for the length of the story, but here it goes. Also, all names have been changed to protect others identities.

A few points about me…

I was nineteen years old and things were going pretty well. I had a job, and at that time it paid way better than minimum wage. I was in college, mostly trying to figure out what I wanted to do. At that time I was fairly muscular, 5'10", and about 175 lbs. I'm not big in the dick department, statistically average. In high school I didn't have a lot of luck with girls, but as I got to college things started to change. Women weren't throwing themselves at me, but I wasn't having much trouble.

Background of the story….

Anyway to the event for this story. I was single, partying my balls off, and generally was on the hunt constantly. This particular night, like many others, I went to a bar that was fairly relaxed about underage consumption laws. I mean this bar was ridiculously easy to get into and get drinks at. I got fairly drunk, and being the stupid, young dumbass that I was got in my car to go home. (Note to those reading, I don't condone my actions, but rather now find them reprehensible.) Anyway, I was halfway home when I realized a few things: a) a cop had just appeared in my rearview, b) I was way too drunk to be driving, and c) I really needed to urinate.