The Second Time's Not A Charm

Upon the recent dissolution of my two and a half year relationship, the longest I've ever had, I'd thought I'd made a smooth transition from guy to guy with the presence of Drew, a fellow student five years my junior. Drew and I shared similar interests and he seemed willing to do nice things for me without expecting anything in return. How nice. We hung out as friends for quite some time, going to dinner, movies, hanging out. I admit I wasn't attracted to him off the bat, but he has an easygoing, humorous personality that eventually made me want to fuck him. Still, I could never figure out if Drew just liked me as a friend or wanted me as his girlfriend. He never gave any indication at all that he was sexually attracted to me. I guess young guys are like that

I should mention that my "ex" and I still talk and one afternoon, when my best friend needed a photographer and witness for her wedding to a Ukrainian immigrant, we got together and had sex in a desperate heat of passion. Later that night, I met up with Drew, and in an awkward, pot and alcohol induced moment, we too, had sex for the first time. I had successfully made the transition from ex to current in one day. Or so I thought. I was so giddy! I called all my girlfriends to brag, but, being the horny bunch they are most had already done something like that before. A few days later, I made the official announcement to my ex that I was seeing someone else and he hung up on me in a fit of anger. Almost immediately, I regretted it.

The first time Drew and I fucked, it was strange and wonderful all at the same time. Like those moments you wait so long for that you can't believe they're happening when they finally do. He was completely silent, only asking, "Should I go get a condom?" at one point, but never saying anything else. Maybe he didn't want to disrupt his downstairs neighbors, but I almost felt guilty making any noise, so I tried to whisper. I was used to being with a guy who loved talking about sex and having someone talk dirty to him more than he liked having it. Drew never talked about sex, never talked during sex, and never talked about the sex we had after we had it. If anyone knows my friends or me they know this is not acceptable. I couldn't tell if he enjoyed himself and was afraid to ask.

However, in the days afterward, I kept thinking about fucking Drew, how I liked his cock, his technique, the newness of getting to know someone's body for the first time. My best friend told me the only thing I could do was have sex with him again. Still, we went back to being "friends", hanging out, but never acknowledging that we had sex with each other. Things got really awkward and Drew got kind of rude. I started thinking more and more about my ex and how badly I wanted him back. I tried calling him, telling him I made a mistake, but he wouldn't communicate with me at all. My best friend moved away and my other best friend announced he was moving away in a month. I was a neurotic mess and was being torn to pieces. Worst of all, I needed sex, badly.

I have a love/hate relationship with the opposite sex and if a man loves me at all, I can eventually make him hate me. My ex and I are the perfect example of that, but we are very forgiving of one another. Our tumultuous two and a half year relationship has had more ups and downs than a roller coaster, long gaps of us not speaking to each other, and more nasty words than I ever spilled out as a dominatrix. Even so, we are both very similar in many ways and after several weeks apart, we find ourselves dying for one another and sending text messages saying "miss you" and "I am sorry", blah, blah, blah. Absence really does make the heart grow fonder and, when the two of us finally get back together, we realize how obsessed we are with one another. This time was no different. When he finally picked up his phone, we talked smoothed things over, met for a drink, and were full of love for one another. I told him I'd slept with Drew and he forgave me, but wanted to hear the details (as always. Yes, he knows about my lifestyle).

Despite all this, the Drew situation was not over. We still hung out, went to movies and such, but the sex part was suspiciously missing. I was curious to experience it again, so I invited him to a film screening one evening with a group of friends and waited to see where the night took us. My best friend's suggestion that he might be gay started to make a little more sense as he expressed more interest in hanging out with my flamboyant friend Sam than me. Nevertheless, we ended up at his apartment after a few drinks, I popped in a porn ("Misty Beethoven", no less!) and we started making out. Right away a red flag went up. He seemed distracted, unwilling to touch me, and just fucking lame in every way. I wanted to fuck; he wanted to dry hump. Ugh. At one point, he went to the bathroom to get a condom and peed for ten minutes. He came out still wanting to fuck, but I was turned off and my pussy was dry as a bone. It was some of the worst, most unpassionate sex I'd even had in my life. So bad that I wanted to charge him for it. In fact, I've been paid for sex better than that and enjoyed it a lot more. In the morning, we got coffees with some free coupons he had and within an hour, I barfed it up and was puking the rest of the day. Apparently, bad sex makes you physically ill.

Whether or not Drew and I remain friends (which might be possible), I have sworn off sex with him forever. The second time was really not a charm and the third time was even worse. It was a good experience for me though, as breaking up and fucking someone else made me realize how much I love my "ex" and how he will always be my current, despite our troubles. Though he may not always be the best lover, at 37, he is full of love and passion, something 25 year old boys like Drew lack.