Gary:
early spring 1999
Gary was a waiter at a local Mexican restaurant. It was school girl crush at first sight. The boys I went to school with were cute in an “I’ll be manly some day” kind of way. Gary was hot in an “I’ll turn into a giant douche someday” kind of way. In true douche bag form he immediately made out with another girl and showed up to my house with a band aid on his neck to cover the hickey. Did I slap him and turn him away immediately? Of course not. I made out with him even more. I’d show him that I was way better at it than anyone else! This went on for a month or so. The whole time he was begging me to have sex with him but I had no desire to. I had been hurt so badly by the last guy, I was totally disinterested in it. He was so persistent. I finally gave in. Even though he was only the second person I had ever had sex with, it was horribly disappointing. His penis was so small, the condom literally fell off of it. Fell off. Yes, fell off. It was over in a few seconds and we broke up two days later. FELL OFF.
David:
late spring 1999
Oh David. He was my one true love (or so I thought). He was the senior football stud. I was a junior and had been waiting my whole life for someone like him. Everyone wanted him and he was all mine. I loved him so. We were going to be married and have tons of little football playing, camo wearing, beer swilling babies. It was my dream come true. Even when we went bikini shopping and he told me I would look great once I lost a few pounds. Obviously I cried. He tried to make it better by telling me that in the old days of lords and ladies I would be considered “wealthy” because I was pale and a little pudgy. That means I eat well. Not like the poor people who are stick skinny….I was still over the moon. Clearly I’m an idiot. The first time he told me loved me I sobbed like a war widow. Nothing could go wrong with our love. Until everything did. The summer after he graduated high school we spent every second of every day together. He could do no wrong in my eyes. Even when he got our group of friends thrown out of the local water park and banned for life. That genius tried to give some of our smuggled in booze to a lifeguard. He was brilliant. He left for college at the end of the summer and I would go visit him as often as possible. We were blissfully happy for about a year. Then out of nowhere he dumped me. Two days before our anniversary. In my car. While I was driving. After he had opened the gift I had gotten him. Brokenhearted is an understatement.
The following summer was great fun for me. I had a few boyfriends, a couple of mistakes, a summer fling with a boy I met in Cancun who was from my area. He had the biggest thing of anyone I had ever seen and still holds that title to this day. I never told him that. We are still great friends so if you read this, Congrats!
Steve:
The following spring I went on a trip to Louisiana with a friend to visit her boyfriend. There I met Steve. He was a Cajun boy with a heart of gold. We dated for two and a half years. The first time we had sex his roommate walked in on us with my legs straight up in the air. He stood there dumbfounded, tried to cross the room quickly to get a condom for his own sexcapade, tripped over the space heater on the floor and caused a huge ruckus. There were many encounters like this. It was college and he was in charge of the largest boys dorm on the campus. We had a great relationship. He was sweet, fun, kind and funny. I ended up breaking his heart. He got me back though. We tried to reconcile a year or so later and he promptly met a girl while working in Mexico, cut off all communication with me and married her a few months later. I saw him about 3 months ago. It had been almost 12 years since we had seen each other. I am happy to report that he got fat. His wife is lovely though and I wish them the best.
Jason:
Summer 2003
After Steve I needed a little more excitement in my life. That’s where Jason came in. He was in a band and rebellious. I was 21 and in the most exciting relationship of my life. We partied a lot and had great sex. I was more sexually open with him. Mostly because I was so drunk the whole time we dated. His band played all over the state so where ever he went, I followed. Everything was great until he caught some guy chatting me up at the bar during their set. This brought forth the most jealous being I have ever seen in my life. Things went south. He never out right hit me, but he smacked me around quite a bit. My breaking point was one night when he threatened to kill my dog. Game over. I broke up with him immediately. This did not stop him form stealing my ATM card, taking all of my money, showing up at my house drunk all of the time at 4 am and banging on my door. He would even call me and hang up and if I tried to call back to tell him to stop he pretended like he didn’t know what I was talking about and would call me crazy. Nothing makes me crazier than a crazy person telling me I’m crazy!! Hello?? Caller ID! I know it’s you!! It turns out, he had been stealing my money to take other girls on dates. I really know to pick em!
Trent:
Now Trent is the friends boyfriend from the “Steve” story. Before you go getting all mad at me, they broke up soon after that trip. She cheated on him. Since I was serious with Steve I was spending a lot of time with Trent. My friend, Rebecca, and I drifted apart. I was spending almost every weekend with her ex, after all. Needless to say, Trent and I became VERY good friends. And for YEARS it was JUST friends. Until one night…..Christmas 2004 I went to a holiday party with him. It was at a swanky hotel and had an open bar. I’m in! We had a little too much to drink and ended up in bed. It was great fun. Except for me hitting my head so hard on the headboard we were considering going to the hospital. That was pretty much the extent of our affair. We agreed it would never work and we would kill each other and we both valued our friendship too much to jeopardize it. We are still close friends and I am happy to report that he married a beautiful and amazing woman (way too good for him) a few months ago and I have never seem him happier.
Clay:
The next guy I dated was in the band with Jason. He wasn’t particularly good looking or funny or anything really. He’s probably what you would call a big dumb lummocks. It lasted about 9 months and nothing very exciting happened the whole time.