Craigslist Chronicles Ch. 01

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.

I think they sensed my discomfort, cause things soon changed up.

He told her to blow me. She declined.

She reluctantly agreed to a handjob, reaching over and taking my soft dick in her hand, stroking it. It felt soooo good, her soft skin on my cock. Honestly, I still had trouble getting hard with him watching.

We talked about it a little bit. She said I was welcome to jerk off. Said I could cum on her anywhere other than in her hair. She suggested on her tits. I was kinda disappointed, hoping for something more, but agreed.

They went back to fucking. He was on his back and she was riding him. I stroked myself while watching, and touching her. I started rubbing my dick along her harm, and her shoulder, and her neck. I thought maybe if it was right next to her face she'd take it in. But it didn't happen.

Somehow he pulled me forward and I was kneeling over his shoulders, again with his mouth on my dick. At this point, it was soft again, and didn't last long before I pulled away.

I went behind her, and again resumed stroking myself. I rubbed my hard dark everywhere I could on her. She was leaning forward kissing him. I was now rock hard, stroking furiously. I touched everywhere and rubbed myself everywhere I could. toward her ass. All over her back. She even reached back to move her hair out of the way for me. On her neck, to.

I remembered he comment not to get cum in her hair.

I kept stroking myself while they fucked.

Soon, I felt it approaching. I didn't give either of them any warning.

Standing straight up on the bed, I released my semen onto her. I came onto her back. The first couple shots pooled near her left shoulder blade. Then a few more dribbled more toward the center of her sexy back.

I've always liked a girl's back. Its so sexy and natural. And now I had just cum all over one. That part was the best experience of my life. And on top of it to see the product of my work on her skin.

When the first warm shot of my cum landed on her she left out a soft moan. Yes, she enjoyed it. I know, not many girls might enjoy having a strange boy cum on them while they have sex with their boyfriend, but she did.

After I finished, they stopped grinding. The guy asked her if I came on her. She confirmed that I did. He strategically maneuvered out from under her, not upsetting her balance, and went off to the bathroom.

She stayed laying on her front to keep my cum pooled on her back.

I layed down next to her and we kissed. I finally asked her name. "Kay," she told me. I have no idea if its real or not, but I thought it cute.

The guy came back from the bathroom with a wet rag. Before cleaning up, though, he grabbed a camera and snapped a picture of her cum-covered back. The he cleaned her up.

We talked for a few minutes afterward, mostly random shit. Somewhat about all my firsts that night.

Then she agreed to spread her legs and let me eat her. I honestly have no clue if I was doing it right or not, but she seemed like she was enjoying it. My first taste of pussy was delicious. The smell was great. I wanted to keep going but she stopped me. Too sensitive from the recent fucking.

I was, of course, hard from smelling her cunt, and suggested I could cum again. They declined, saying it was getting late and they needed a meal break, also time for me to go.

They disappeared into the kitchen leaving me to get dressed. Once I had my coat on (it was february), she wandered back in naked, alone. I was thrilled to have a moment alone with her and just her.

She reached up, kissed me, and we made out for several minutes. I touched her everywhere I could. "Thank you for coming, and cumming." She laughed at her own bad pun.

I pleaded for another chance, even a quickie just to say I did it. She was so pretty, and fucking hot. But it didn't happen. We kissed one last time and I headed for the exit.