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.
Eventually, they found themselves in missionary, with me beside them. He was pounding her somewhat hard, but also gentle. I asked if I could kiss her. She agreed.
At 24 years old, it was the second girl I had kissed.
We made out pretty strongly while he fucked her. She was so pretty. Her skin was so soft, I was trying to feel her everywhere. He told me to suck on her nipples, and I obliged. The closer she got, the harder she wanted her nipples sucked. Soon, I heard her cum.
I wish I could've seen her face, but my mouth was attached to her tit.
I have no idea if he came or not, or where.
After they finished, they both turned to me and said "Your turn!" Exciting part.
She kissed me again. Then trailed slowly down my neck. Most erotic experience of my life, feeling her soft lips on my skin. Then down my chest. It tickled when she got to my nipple. Then a little lower. But that's where she stopped.
He, on the other hand, was trying to do the same on my other side. I wasn't really too into it. Nevertheless, I ended up on my back and he took my dick into his mouth. After the first two sucks, I jumped at the sensitivity. Add to it I wasn't too interested, and I quickly pulled away.
