A couple weeks ago I put up a post on Craigslist about wanting to lose my virginity, because I'm 28 years old and it was getting embarrassing. I didn't expect anything to come of it but it was a desperate last-ditch effort before getting an escort. I started to feel really pathetic about it because after I posted it I sat there refreshing my email for like an hour hoping for a response and nothing came through.
I kept checking back all day long and nothing, not even spam. Eventually I jerked off and went to bed and feeling extremely bad about the whole thing.
When I woke up the next day I had a new email from craigslist - a response to my post! Awesome! I clicked on it hoping for the best and got something unexpected. All it said was "You down?" and had a picture attached. The picture was a topless self-shot fit girl, no face, big-ish tits covered by her arms, wearing white boyshorts. I figured it was spam and started to get depressed again, but just for the hell of it I ran the picture through google reverse image search and tineye and they both came up with no results. I went out on a limb and decided to assume it was real, since if it was spam they were using a picture that wasn't anywhere else on the internet, so I replied and said that with a body like that, anyone would be down, but I wasn't sure they weren't a spammer.
A few hours later I got a reply, apologizing for not being more obvious. She said she was 28, same as me, disease free, and got really turned on by the idea of fucking a virgin and being the girl that I would remember for the rest of my life. Holy shit! She also asked me to send a picture. So I took a (clothed) picture and sent it and 15 minutes later she replied to the picture by saying "OMG your place or mine?" and gave me her phone number. I thought the OMG was a little weird and didn't understand it but fuck yeah, I was about to lose my virginity to a girl with a slammin' bod so whatever. I texted her and told her to come to my place and gave her the address, and she asked if that night would be good. Fuck YES that night would be good. She asked if I lived alone and I said I did, and she said she would be over at 8. I went out and bought a box of condoms (for the first time ever... it was really awkward).
A little while before 8, she called me and told me she was outside. Holy shit, here it was. I was getting extremely anxious and nervous. I went and opened the door, and here's where this gets unbelievable (I still can't believe it happened) and I found out what the "OMG" was all about. It was a girl I went to high school with! No fucking joke. Not just a girl I went to high school with, but a girl I had a huge crush on in high school. I used to, no joke, jerk off to her myspace pictures on like a daily basis (I didn't tell her that... lol).
I tried to keep my cool and invited her in. We sat and had a couple beers while catching up. I told her about my crush on her in school and how back then I wanted to lose my virginity to her so badly, so it was funny that she was here now. She asked why I was still a virgin, and I told her that I was very shy and didn't even know what to do, and my dick was below average and I was so embarrassed about it that it made it hard to even approach the situation. She thought that was kind of cute and told me she would teach me everything I needed to know that night. It was like a dream come true! I was already hard as a brick and she hadn't even touched me yet, and when she noticed she looked at me and smiled then bit her bottom lip.
She sat down on my couch and I went and sat next to her. I told her again how embarrassing the whole thing was for me and asked if she could just take control of the situation and tell me what to do. She nodded and got on my lap, straddling me. She asked if I had ever done anything with a girl and I told her that kissing was the furthest I had ever gone. She asked if I wanted to feel her boobs and without even responding I reached up and cupped them in my hands, then I just sat there holding them for what felt like forever but was probably only a few seconds. I felt like I was already going to cum, this was the closest my dick had ever been to a vagina and only two pairs of jeans separated them. Then she laughed at me and told me not to be so gentle and took her shirt off. I tried to unhook her bra real quick but couldn't figure it out, so I lifted it up and started squeezing her tits. She started biting her lip again and took the bra off too. Her nipples weren't as nice as I used to imagine them but it was still a great pair and I kept squeezing and playing with them. She started squirming around on my lap and rubbing against my cock, so I ran my hands down her side to her thighs, which I held on to.
She unbuttoned and unzipped my jeans, pulled my dick out and started stroking it. I told her no one had ever even touched it before. She was probably stroking my ego but she said it wasn't as small as I thought it was and that huge cocks weren't all that great because sometimes they can really hurt and they don't guarantee good sex. She asked if I had ever seen or felt a pussy before and I said no. She slid off of me down to the floor and licked my cock from the bottom of the shaft up to the head, then stuck the entire tip in her mouth and sucked/licked it for a few seconds. It felt even better than I had always imagined and I moaned "oh god, I'm about to cum" and she stopped. She stood up and took her jeans off and asked if I wanted to finger her while I cooled down so I wouldn't cum right away. I was waaaay in to the idea (my first time feeling a pussy, hell yeah!!)and suggested moving to the bedroom, which we did. She laid down on my bed and told me to take her panties off. She apologized for not wearing "something sexier" but they were just white cotton boyshorts which I find much sexier than anything else and she giggled when I told her that.
I pulled them off her in what felt like extreme slow-motion. This was my first time ever seeing a naked girl with my own eyes and her pussy was every bit as beautiful as I used to imagine it in my fantasies. It was small and had a kind of natural spread to it and really did look like a flower. She thought it was cute when I told her that. I told her how incredible this all was and she giggled and like fake-yelled at me to stick my fingers in. I stuck two fingers in and felt around and I was in heaven. She was soaking wet and it was slick and warm inside. I gently slid my fingers out and back in a few times and told her I didn't know what I was doing. She again told me not to be so gentle, and to really get up in there and find the spongy part. I stuck my fingers as far in as I could and found what she was talking about and she moaned when I touched it. I kept running my fingertips across it, taking short breaks to pull my fingers out a little and then go back in. Her moaning got louder and more frequent and after a couple minutes she announced that she was about to cum. It was a hell of an ego booster! I started to pull out and she again fake-yelled at me to get back in there and finish the job, so I slid my fingers back in and started rubbing it more intensely. She started to squirm and gasp and moan louder. Her eyes rolled back in her head and she kinda screamed a little and then sighed. She looked at me and smiled and told me I did a good job. That felt fucking great! I was feeling like the fucking king of the world. I pulled my fingers out and sucked her juices off them. It tasted a little salty, not as good as I had always thought it would, but not bad. I told her she tasted incredible anyway.
That was all just the beginning, we had a lot more fun that night... but I need to stop writing for now. I'll finish the rest later if there's interest
