circa 2017 when craiglist was still around kicking, and we didn’t know it would be going away. I had recently moved across country and was living on my own. I was in my mid twenties and attending university for law school when everyone around me had already been in long relationships or would brag about the experiences they’ve had.
I had no experiences to share. I didn’t have any. I felt like I was missing out on something so one night, when I was feeling lonely and horny, I thought I’d post an ad on craiglist just to see. I made it very simply and straightforward. I said I was a virgin who wanted to meet someone to loose my virginity and hopefully learn some things.
For the first 2 days, I only got dudes and scam emails to reply. However, I came back home from class on the third day and checked my messages and saw there was a message from an anonymous person with just a phone number to text. I was extremely scared because it could have been a random guy trying to rob me.
Eventually I got enough courage to text the number and surprisingly they replied back. We got to know a little bit about each other and she asked me some basic details. I sent some sfw pictures but she only said she’ll verify herself on the phone – not send any pictures. I figured that would be okay and after 3 or so months of constantly talking, being turned on and sexting, we set a date to finally meet.
I finally arrive and I find out she has 4 dogs and 5 cats. They were really friendly though and I remember she said that her dogs aren’t normally this friendly with strangers so that kind of calmed me down a little. We just sat in her kitchen and had some tea and talked for a little bit about her work and life and then she invited me to show the house. I genuinely thought I was getting a tour of the house but it turned it she lead me to her bedroom and said okay, let’s get naked.
I was extremely nervous and I think she realized that as well. She asked me if I ever eat pussy before and I said I hadn’t. She said, let’s start with that so I called upon all of my memories of /r/sex and the stories I had read on here about going down on a women and give more effort than I had to anything else in my life. I think she really enjoyed it because she lifted her hips, grabbed my hair and moaned really loudly throughout.
Afterwards, she asked if I was ready to have sex. I said it was the only thing on my mind. I lost my virginity in missionary and she was very supportive and encouraging the whole way. I will never forget it.
After we had been in missionary for a while, we tried some other positions until finally I came inside her. We then spent 2 hours or so just cuddling in the bed and laughing and talking and sharing the experience.
Overall, I’d say it was my most memorable night with her. I was really lucky to have found someone who was understanding, open minded, and extremely beautiful. We still keep in touch to this day even though I moved from that country 5 years ago. I definitely learned so much from her.
So yeah, that’s pretty much it. I’m more than happy to talk about some of our other times together but that was essentially my one and only craiglist experience and it was the best I could ever ask for.
Source: reddit.com/r/gonewildstories/comments/11ibjbf/i_lost_my_virginity_from_craiglist_fm
Do plan on meeting her again anytime?
How old was she?