My only experience [F]ucking a rando[M] craigslist dude.

A few weeks after I turned 18 (2011) I packed my bags and drove over 500 miles to live in my favorite city. I had a modeling job and a studio apartment lined up there and I was quite pleased with myself. I felt very adult although (I didn’t realize) I was still a naive teenager.

Once I got to my apartment and unpacked my stuff (basically just clothes) I showered, put on my sexiest lingerie, did my hair and makeup, and broke out the bottle of wine I’d been saving for the occasion. Obviously I wanted someone to celebrate with. Tinder did not yet exist. I daringly went on Craigslist “casual encounters” section intending to find a hot twenty-something or thirty-something guy who was looking for a one-nighter. I wasn’t sure if I would be daring enough to go through with it but I was getting soaking wet scrolling through the gallery of local cock offerings.

Although I was intending to find a slightly older, taller, buffer man, I found myself very nervous about the prospect of inviting over such a physically domineering stranger. Then an ad caught my eye. The CL ad poster had also just turned 18 (literally that day) and he was a virgin. Even though he was a cute guy, he was so desperate to lose his virginity that he posted to Craigslist personals as soon as he turned 18. I felt sorry for him. I also thought he was pretty cute.

I messaged him and asked him to come over right away. (He showed ID proof it was his 18th birthday.) We shared a little wine (oops not 21) and then he shyly asked if he could kiss me. I let him lighty, shyly kiss me at first. Then I led him into a deep passionate makeout session. I placed his hands on my chest and let him pull my lacy bra down, exposing my nipples, and he gently pinched and twisted them. He was obviously starting to get really worked up. I was afraid he might cum before we even got started.

He looked up at me with big brown eyes (I remember them so clearly) and he started ranting on about how desperate he had been to lose his virginity that he was willing to post on craigslist. He said he just wanted to lose it so bad that he would have fucked just about any woman who replied no matter what they looked like, their age, or how sketchy they were. He complimented me saying he couldn’t believe he ended up sipping “fancy wine with a hot young model” (it was not fancy wine lol)

I held his head gently to my bare 38DD breasts and stroked his hair. We laid down together that way, both on our backs, his head was on my chest and I could play with his hair. I talked to him and listened non-judgmentally, discussing his feelings. I just wanted to be sure that he was sure he wanted to lose his virginity to me, right then, for the right reasons. When he said yes and I was satisfied that I believed him, I asked him if he wanted to strip off my clothing piece by piece, he said yes to that too.

He peeled off my stockings and garters, unclasped my corset (it was the easy kind) and my bra (I helped him a bit, bras are hard) and I was sitting there in just my g-string. He had seemed so nervous that I thought letting him keep his clothes on for a bit would make him more comfortable and make things kind of hot. He lay back down this time facing my chest, licking and sucking my nipples, swirling his tongue around each one, alternatingly switching back and forth. The whole time he was shyly fiddling with the side-strings of my g-string.

I took his right index finger and guided it to my labia, dipping it into my wet cunt slightly for lubrication, and then guiding his finger to rub pressure in circles on my clit. I figured it would be a good lesson for a virgin. He rubbed in circles for a bit and then smiled the cutest smile, shifting his position. He informed me he is actually left-handed. He unexpectedly shoved both the middle and ring fingers of his left hand into my pussy. I yelped and he stopped, apologized, said he just wanted to see “how deep it goes.”

I told him no need to apologize as I love a good rough finger-fuck. I told him to explore my anatomy to his hearts content. He obliged enthusiastically. He roughly manhandled me, spreading apart my pussy lips, feeling up my asshole, pinching and pulling on my clit. I was loving it. Having my pussy hungrily explored by a horny teenage virgin was one of the unexpectedly hottest experiences of my life.

I asked if he was ready to fuck and he took all his clothes off unceremoniously. His cock was already raging hard. A good solid 6″ or 7″ uncut. (I love uncut.) I handed him a condom and he was just baffled by it. He could not figure it out. I pulled out another condom and I put it on him easily. He looked a little embarrassed but I tried to be comforting.

I french-kissed him deeply again and looked into his gorgeous eyes. I asked him if he was really a virgin. He said yes. I believe him; he seemed like one. I told him I am clean and on birth control, and that I think he deserves to feel natural, raw, skin-to-skin sex for his first time. He eagerly agreed, and I pulled the condom off him. (Yes this was very “naive teenager” of me, but no I didn’t catch anything! I still believe he was a virgin.)

I let him pick the position and told him he could cum wherever he wanted. He laid back and then pulled me on top of him, straddling him, and pulled me in for a deep kiss. His virgin cock penetrated my warm wet pussy while we were making out and he was rubbing my nipples in gentle circles. I was running my fingers through his hair and lightly holding the side of his face. When we broke from the long makeout session, I continued thrusting my hips, pumping my swollen wet pussy lips up and down his bare cock.

When I started to lose steam we flipped over missionary style and began making out again. He reached down and rubbed circles around my clit while fucking my pussy, (just the way I showed him earlier, fast learner!) He told me he was getting close and I told him he can cum anywhere. He romantically kissed me again and told me he wanted to cum inside me. A few thrusts later, he did just that.

I had actually already cum earlier from the rough finger-fucking and pussy manhandling, but the rhythmic throbbing of his cock while filling me with spurt after spurt of hot cum was so hot I came again right at that moment. He collapsed on top of me and I held him close. Lovingly whispering to him that he is extremely sexy and that he made me cum twice on his first time. He smiled and kissed me back. It was late so I let him sleep in my bed with me, holding me, both of us naked. The stuff he had said earlier about how bad he felt being a virgin made me want to give him the full “girlfriend experience” of cuddling and affection. I wanted it to be special for him.

In the morning we had sleepy wakeup sex, showered together (did some oral fooling around in there) got dressed, I made us coffee, and then he went on his way. Before he closed the door on his way out, he stopped and told me again that he had felt like a desperate loser for turning to CL to lose his virginity, but that I had given him an experience beyond his wildest expectations, and a memory he would never forget. I kissed him again and he left. I felt so happy to have made his first time as positive and special as I could for him.

Source: reddit.com/r/gonewildstories/comments/7nhsb8/my_only_experience_fucking_a_random_craigslist