My first boyfriend

As things were winding up with the intern, I posted a random "who wants to watch a movie and cuddle" ad on craigslist. As always, there were a bunch of responses, but a couple of them were actually worthwhile. One guy was pretty cute and I tentatively made plans with him that weekend. I got mail from another guy who sounded nice, but his pictures didn't come through. I only had one free day over the next week. I got mail from the nicer sounding guy with pictures, but he wasn't quite as attractive as the guy I already had plans with. Still, he sounded like the better guy. The other guy just wanted to feel a hard body against him whereas the second guy seemed to have more potential. Then I noticed the first guy's email address was a permutation of "slut seattle" so I decided to cancel and go with option number two.

I made plans to meet him at the dog park. Oddly enough, he told me he was going to borrow his dog from his ex. This should have been a red flag to me.

We exchanged nice mails throughout the week. Eventually they got flirty and then they got hyper flirty. Me, "I'm going to wrestle you and pin you to the ground." Him, "I'm okay with anything as long as you are on top of me." Eventually, he asked for my IM info (god I fucking hate instant messaging...). We started chatting a lot and things started getting more graphic. At one point I pressed him on whether he was a top or bottom, and he got uncomfortable and said that he just wanted to let things develop naturally. I warned him that I'm really inexperienced and shy on dates. He assured me that he was friendly and that things would be fine.

I got to the dog park early and spied vehicles pulling in. We had told each other which vehicles we drove and I saw a car that matched his description and saw a guy that vaguelly fit his description jump out. He was a year older than me, three inches shorter, and mediteranean. Honestly, I was a little dissapointed when I first saw him. He had kind of an average to mildly fit body with a flat ass and a tiny belly. He had a cute face and a great smile though. When we greated each other, he had a great voice. He was pretty masculine. He had a very friendly, warm demeanor and was quite flirty. I relaxed a little with him and enjoyed watching our dogs play. We lapped the park and then I asked if he wanted to grab lunch. He did but was puzzled about what to do with the dogs. It was a hot day.

I had him follow me to my house. I got the dogs some water and cooked lunch. We chatted and had a nice time. After lunch, I gave him a tour of my house. It ended in my bedroom and then I realized this was kind of awkward. I suggested we go sit down in the other room. We both sat down on the couch. I warned him before while IMing that I had never made a first move with anyone. He sat there and laughed and said, "you really aren't going to initiate anything so how about we just hold hands." That was all it took. I pounced on him and soon we were rolling around on the couch. Then I rolled him off the couch and pinned him to the ground. I rolled him over and laid on him kind of like we were in missionary position. There was a lump as hard as a tire iron in his shorts. We took off our shirts and rolled around some more and then he said he was getting rug burn. I apologized and led him to my bedroom.

I wasn't interested in having a fling so I had decided that our pants were staying on. I told him that was what I wanted and he said he was fine with that. We played around for hours and were having a great time. After a couple of hours, I knew that he had an event he needed to go to that night and that he needed to leave soon. I pulled his waist band back a couple of times and looked inside. Finally, I decided that I wanted to send him off with a blow job. I pulled his pants down and started sucking him. He asked if he could reciprocate and I told him no. I sucked him earnest for a long time. He said, "you want to see it work don't you?"

He warned me that no one had ever gotten him off through oral (he wacked off a lot and was kind of rough with himself). Eventually, I shed my pants and we stroked off together. I've always been a projectile shooter with high volume, but I was surprised when I came how intense it was and how many pulses there were. I sprayed everywhere and hit him in the ear. Then he came and shocked me. He completely soaked me from waist to head and got some on my face. It was actually quite a sweet and tender experience (after toweling off).

We met up the next day and took turns fucking each other. It was really sweet and seemed innocent. He hadn't dated much. He had been in a seven year relationship and he ended within the last year. He hadn't had sex for the last couple of years of his relationship. He made up for lost time with me. We exchanged loving emails and talked on the phone every day. We saw each other a couple of times per week.

We had some disagreements but the hardest things were probably that he was in a pretty rough place in life. He and his ex owned several properties together and were still in daily contact. They were also best friends. They fought all the time, and my boyfriend couldn't tell his ex that he was dating. My guy would invite me to things and tell me how thrilled he was that I was going to be his date and then cancel because he found out his ex might be there and felt like it would hurt him too much.

We dated for two months.

Eventually, his ex couldn't afford to live in the house they used to live in together by himself. It was really sad to both of them when the ex was moving out of their house to get it ready to sell. When things were already tense, their dog swallowed a ball and died. It was too much and his already emotionally fragile ex had a meltdown. I stayed up at night with my boyfriend crying about his ex and being afraid the guy would kill himself. I'd take him out to do something and he'd think of gifts to get his ex for Christmas that might bring him some happiness.

On a Friday night, we had talked about getting together and then he decided that he'd rather stay home. He called me the next day told me that he had gone over and smoked pot (and I am pretty hardcore anti-drug) with his ex. I had a hugely busy day and then accompanied my boyfriend to a commitment ceremony for his coworkers that he didn't even like. It was an awful experience. We hadn't had sex in over a week and I wanted to at least cuddle with him after it was over, but he said he just wanted to be by himself that night. I was feeling really unappreciated and abandoned.

The next day, he called me up and said that he really wanted to see me. He was just going to have brunch with his ex (for chrissake!) and then grab a couple of things from his old house and that we could get together in a couple of hours. I was all excited and cleaned up and made plans to have some fun with him. I got everything done and sat around waiting. I heard from him around 6pm that night. His ex's brother had come over and he had got caught up chatting with him and helping his ex. He acted really put out and tired. I told him we didn't need to get together and he acted relieved. I quickly ended the call.

After I got off the phone, a friend called and asked me if I wanted to run grab dinner. I said sure. Then he called back and said he wanted to come over. I told him after dinner. When I got back, he came over and I told him that I was pissed. He was furious that I wasn't being sensitive and supportive. We fought and fought with no resolution. Eventually, we kissed and sort of made up with no resolution. We made out and then went to get ready for bed. He stripped down to his underwear and I came over to him and started to slide his underwear off and he got mad at me and said that we could do that in the morning since he was tired. I was annoyed. I got up the next morning early and went to the kitchen to try and surprise him with breakfast. I started cooking and then he appeared in the kitchen fully dressed and said that he should get going. I couldn't handle it and told him I couldn't see him anymore. He seemed relieved. It sucked.

We exchanged emails after that and it seemed like we might reconcile, but then we started arguing through email. Email is such a bad form for communication, but it is especially bad for negative communication. The tone and subtlety are lost. Things escalated until each of us were saying very hurtful things to each other. He got mad and stopped speaking to me. It's been a couple of months and we have little to no contact anymore.

I honestly don't have any interest in dating him, but he was a special person to me and I hope to have some sort of friendship with him at some point. He really wasn't in a spot were he should be dating. He knows that now, but I was kind of collateral damage. Still, he was a nice guy and it was important to me to see that I could have a relationship with a guy. I do know that there are nice guys out there now. I just need to find some who don't have dysfunctional relationships with their exes :)