The Dildo Awards

R.B. Winters
R.B. Winters
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This is a top ten countdown of the guys that made my life interesting and messy.
10. The DJ: My first real boyfriend. I was 18 and he was 24. The DJ was one of those guys that seemed perfect. He was sweet, attentive, and secretly a gigantic whore. Too bad I didn’t learn a lesson about DJ’s here. The DJ and I were over when I showed up to his apartment and found him in bed with a twinkie. This was one of those moments that made me wonder if he was looking for someone with personality; the boy in his bed certainly didn’t have looks.
9. Newbie: Oh little Newbie. As of late we’ve exchanged a few friendly text messages. I would say we’re on good terms. Newbie was searching for a boyfriend, or at least someone to stand on the other side of the glory hole at the gym. Sadly, I was more interested in my hand. Fun fact: Newbie slept with The Devil before he met me. The problem was that he told me he knew The Devil and said that they never did anything. I went to the sex source and found that to be a wet spot of a lie.
8. Biker Boy: This relationship was short and probably in my favor. Biker Boy was another great guy; he was just a little too possessive. I was forced to show him the door when he told me to choose between my wife and himself. I would never pick a guy over my Ray Ray. Why we kinda liked him: He gave me a laptop for Christmas. Unfortunately, it was replacing the one he broke. Why we’ll remember him: The day I broke it off he locked himself in my bathroom and refused to come out. When he finally left he threw a snowball at my window and then text me five minutes later to ask if we could talk. Ray Ray and I laughed about this for hours that night over a pitcher of beer.
7. Wall Street: If I qualify as a Negative Nancy then he must fit into the category of her mother. Never before have I met a person that was such a downer. The boy had a big package, I won’t lie, but he was so short and skinny I’m surprised he didn’t carry a brick in his bag to keep from being swept away by the wind. Wall Street gave me the choice to be serious or hit the road. I hit the road, literally. I left his place, walked down 34th Street and called Stay Lo so we could start mocking him.
6. Dollar: Dollar will make a great wife someday. He already has the drinking problem going strong and a lady friend to encourage his bad behavior. I did love his lady friend. If I could have stolen her, I would have. I imagine him marrying someone like Wall Street, sitting around their penthouse apartment, and beating the Cambodian children they illegally adopted. I’ll always remember Dollar for hurting his ankle and being unable to help me move into my first Brooklyn apartment.
5. The Cop: This boy has one good thing going for him, and that would be his current boyfriend. Sadly, The Cop recently cheated on his boyfriend and they may be over. The Cop was another nice guy, but he was clingy and had breath like an asshole (I’m not into rimming).  I felt compelled to get even with him after our breakup because he behaved like such a douche. What I did: Slept with his current boyfriend. This ended up working out pretty well for me. Chicago (The Cop’s boyfriend) and I became friends and still talk today.
4. The Trainer: Let me take a minute to say The Trainer is still the best I’ve ever had. That’s coming from 5 years after the fact. I was young and fairly dumb when we met. I was drunk at a club and he grabbed my arm. I confused him for my friend Mandee. We danced and he tried to take me home. I said no because I had a boyfriend at the time. I gave him my number and told him to give me a call. The next day I dumped my boyfriend and 30 minutes later was at The Trainer’s door. He banged me like a cheap drum for two months then sent me a text saying he was getting serious with some guy. I was pissed, but got what I deserved for screwing my boyfriend over.
  Why I win: I saw The Trainer last year. He said I looked great. This was coming from the former fit, gorgeous Greek guy. He was tied down with a house, a boyfriend, and a beard full of graying hair. I found it fitting to make out with the friend he was with and put my hand down his pants. I did pour a beer on my Ray Ray right before all of that, but she loved it; just a side note.
3. The Devil: The Devil was a dick. I could leave it at that, but I won’t. I was behaving like one of the needy gross people that I hate while we were dating. He was behaving like the asshole rebound guys that I go for. There are a few theories out there as to why we broke up. What’s true: I’m a lush and he’s a ho. We’re on friendly-ish terms these days, meaning I got over my enraged phase. Watching him setup his own demise has been more satisfying than any revenge I could ever have. Just in case of emergency, as I always do, I save tid-bits of information. You never know when you’ll hate someone again.
2. The Photog: I’ve had the hardest time figuring this guy out. Come to think of it we were supposed to hang out the other day and I forgot about it, oh well. We’ve slept in the same bed at least 20 times, one of which his hand was down my pants. I thought we were going on a date not too long ago, but he ended up inviting another friend and ignoring me until I left. The Photog is either playing a very odd game with me, or he’s totally not interested in me and I’m not getting it. There’s still time for the plot to thicken here, so I’ll hold off on my final say.
Number One: There is only one person in my life that could be the biggest bitch I’ve ever met. That would be me! Did you think I would name anyone else number one? Yes, I’ve been screwed by guys in every way a person can be. I’ve also screwed… over a lot of guys along the way. I’d say at this point my karmic scale is about even.