July 19, 2006

This guy was soooo stoked that someone answered his ad.

After a few emails and a phone call, it was decided that I would come over at midday. He was a graduate student, and I had just quit my job.

We decided that I would dress as if I was going for a job interview. I put on a business suit and heels... but no bra or panties.

When I got to his place on Hayes St., it was obvious he didn't live alone. The apartment was decorated too nicely, plus, more obviously, some of the magazines had a woman's name on the address label. He said he lived with his ex-girlfriend. They no longer shared a bedroom, but neither of them could afford to move out...

After my "interview" we went to the bedroom. I had to find some way to convince him to hire me.

I stood facing the bed as he stood behind me. He unbuttoned my jacket and slipped his hands underneath my shirt to play with my nipples. He started licking my neck. It was gross. His tongue was slimy. I had to tell him to stop.

I took off my skirt and laid back on the bed. He dutifully began to lick my pussy. To his credit, he did lick for a long time, but it just wasn't that good. Finally, I pushed his head up and scooted back. He got a condom and put it on his (unremarkable) dick. After a couple of minutes he came. I didn't.

I said, "Well, I'm gonna go." He said, "You don't have to, you can stay, we can do it again." I replied, "I don't think so," and got dressed and left.

When I got home I found an email from him apologizing for being so lame and asking for another chance to please me.

I ignored it. I also ignored the four more progressively begging ones that followed before I blocked all email from his address.

July 15, 2006

I need a rebound. My boyfriend and I have just broken up - for good. I love him, but it's over. I need someone to help me forget... at least for tonight.

This was the first time I'd ever posted. I had NO idea what I was getting myself into. My inbox was flooded almost immediately after I posted that ad. Why do men feel the need to send photos of their genitalia? Who takes photos of their genitalia, for pete's sake?

After a whittling down process, I settled on one candidate. We exchange a couple of emails, and he sent me his phone number. We chatted for a bit and I got his address. It was late - about 1 am when I got to his apartment in the Lower Haight.

I was super nervous. He asked me to have a seat on the love seat in his room. He sat next to me and began to massage my shoulders. This didn't really help, but I figured "in for a penny, in for a pound," so I went with it. There wasn't really any small talk. He laid me down, pulled down my pants and underwear and dove tongue first between my legs.

I didn't reciprocate, instead I just asked him to put a condom on. He fucked me for a while, then said "let's go into the living room." He wanted to fuck me bent over a chair in front of a window overlooking Haight Street. We did that for a while then went back to his room to fuck some more. He pulled out some lube and asked if he could fuck me up the ass. "I've never done that before," I said. He assured me that he'd be gentle. He was... but I don't think it's my thing. I told him that "there's something to write about in my diary."

I didn't come. I wasn't surprised or disappointed. It takes a lot to get me there under the most "usual" of circumstances.

I left soon after. I felt like such a "bad girl." I kind of liked it. I have no idea what his name is, but I remember where he lives.