In the fall of 2009 I put up an ad on Craigslist, not for the first time, asking if anyone wanted to help me lose my virginity. Sometimes it was placed in romantic m4w, sometimes in casual encounters. It wasn't necessarily serious, mostly a curiosity to see who and what type of responses I got. Kindof an interesting experiment.
Over the months, some responses included the usual spam, offers for pay sex, encouragement to change my mind, etc. One in particular was from a guy who talked about him and his girlfriend opening up their bedroom. We ended up exchanging several emails, and then some pictures.
After a bit, he invited me over his place one night around 9pm. Ill be honest, it was a bit of travel and I didnt know where I was going, so I flaked out. A couple weeks later, he invited me over again, with a mid-afternoon timeframe. I accepted. At this point neither of us knew the other's real name. I had used an alias on the CL email.
I was slightly late arriving at his apartment. As it turns out, I was only about thirty seconds behind the girlfriend. I knocked, entered, and we exchanged awkward greetings. He was wearing pajama pants and some sort of t-shirt, I think, didn't really pay attention. She had apparently come from work; was wearing black stockings and a mid-thigh length black dress.
I'd say she was about 5'5, maybe 5'6, not super-thin but definitely super hot, very attractive. Long, flowing, soft brown hair. Pretty eyes. I wanted her but didn't know how to act.
I sat on the couch. She sat on his lap in the chair while they each had a drink and made small talk. Then, suddenly, suggested moving it to the bedroom. They walked in and I followed.
He walked to one side of the bed; she to the other. They each began taking off their own clothes. "What now?" I asked naively.
"I dont know about you, but we're gonna get naked," she said, looking at me while stripping like she would if she were in her own bathroom. I stood and watched. My first real naked girl.
I slowly took my clothes off and put them in a neat pile in the corner. It felt weird being naked with another person in the room. I was a little too nervous to be hard.
Once they were both nude, he layed down on the bed, she crawled over to him. "I wanna suck your dick." Just like that. That simple. I leaned in for a closer view.
It wasn't a big dick. They talked about that later, and how they were both okay with it. She was bobbing her head up and down quickly. It was actually kindof a slobbery blowjob. I didnt know if it was supposed to be slobbery, first I'd seen, but it struck me as so.
"Do you want some help with that?" I found myself asking. I don't even know why. Yes, I had thought about sucking a dick before, but never begun to act on it. That guy wasn't even that attractive. It was just in front of my face and I wanted to do something dirty and naughty.
She took her mouth off, kept her right hand on the base, and passed it to me. I opened my mouth and took it in.
Not having a clue what I was doing, he made a remark about teeth, but otherwise seemed to enjoy it. This carried on for maybe a couple of minutes before I tired of it and she resumed the blowjob. I resumed my watching.
The guy tried to put his hand on the back of my head for me to go down again, but I didn't really feel like it.
