Dear Diary,
So it seems my hopes to lock up the naughty chapter of my diary and starting fresh has gone amiss. I’ve reformed to my old ways, and so I’m back to write down every juicy detail. It started when I decided I needed a crush to distract me from my ex. I’d been going to a weekly pub trivia night with friends, and directed the focus of my crushing on the adorable Quizmaster.

Each week that went by I barely said two words to him though, and worried that my flirting skills had been lost after three months of being out of practice. Finally, I turned to Facebook to make my move – the safest way to be bold, I figured. “Dear Quizmaster,” I wrote. “Should I finally work up enough nerve to say more than two words to you at the final trivia night, and actually ask you out, or would that just be an awkward situation for both of us?”

The next day I got a text message from The Gentle Giant, a guy I had dated a year ago and hadn’t seen since. After my last break-up I’d texted him for a booty call, but then quickly took back my proposal, realizing it was way too soon to jump back on the old casual sex train again. Now, weeks later, he’d invited me to see a movie with him that night, and I accepted.

Once I finished work for the day I called a coworker who I’d had my eye on, and asked him to grab dinner with me while I killed time before the movie. He’s a few years younger than me, but very pretty. After we ate I told him I had to meet a friend, but that I was going out the next night and he should join me. We hugged goodbye, and I went to meet The Giant.

It had been a year, but he looked better than ever. We did a bit of catching up in the theatre, shared a bottle of wine he’d snuck in, and we settled in for the flick. After the show, he ran into a couple he knew, and they joined us at a bar for drinks. Somehow it came up that I go to pub trivia each week. “Oh, the Quizmaster is my roommate!” The friend said. I told them how I’d just asked him out over email the night before. “I’m sure he was flattered, but I doubt his girlfriend would have liked that.” Yikes. Guys in relationships shouldn’t have their FB profile read “single”. It makes the hunt even tougher for us single gals on the prowl.

It was past my bedtime and The Giant walked me to a cab. Just before I got in he asked if I would come to his place for a bit. “I’m not going to sleep with you,” I said. He said he was fine with just making out. When I finally got in a cab an hour later, I got a text from the younger coworker asking me to come meet him for a drink. Hmmm, I hadn’t been sure if our dinner was just two friends hanging out, or a date. That text made me sure it had been the later. I declined, but said I hoped he’d come out with me the next night. And he did.

The following day after work we went to a near by bar. I ordered some nachos and several drinks. I told the hot youngin’ about a date I’d been on with Goldilocks where I’d choked on nachos and he had to give me the Heimlich maneuver. I swear to go, no more than 10 minutes later, I was choking. Unlike Goldilocks, who immediately came to my rescue, the boy just sat there and asked if I was “going to puke?” Oh, youth. Obviously I was fine, but a bit turned off by his lack of caring. His pretty eyes made me quickly overlook this.

We barhopped all night, and ended up on the patio of Jack Astor’s around last call. I decided we were both drunk enough for me to make my move. I leaned over and kissed him. Half an hour of making out later, we were kicked out of the bar. I probably should have just got in a cab, but thought the ladylike thing to do would be walk him home. We then spent the next hour making out on his front porch. This guy definitely made me feel like a kid again. He asked if I wanted to come to the side of the house with him…and off came our pants. A moment later I was leaning against a wrought iron fence as he fucked me from behind… the only thing blocking us from Wellesley was a shrub. Thankfully, most gay men walking by didn’t seem to be too concerned by alleyway sex.

I thanked the boy for a lovely evening and made my way home. I guess I’m finally ready for no-strings-attached sex again. And as for the Quizmaster, well I’m off to trivia tonight to see my little side crush. I just can’t seem to let go of my fantasy to be fucked while screaming “Oh Quizmaster…do me quizmaster!” I kid. One thing I refused to get involved in is a guy with a girlfriend. I’ve had my fair share of hurt, I don’t intend on causing any myself, despite the nice ring “Fuck me Oh Great Quizmaster” has to it.