(M)y first Craigslist experience with sex

Sat, 08/17/2013 - 19:43 -- Anonymous (not verified)

So, I was always curious about sex on Craigslist, so after toying around with some ideas for an ad, I realized that I loved to masturbate and thought it would be kind of hot and kinky if I stroked my cock while a woman watched me. Then, if anything else occurred after that, so be it.

So, i took some really hot pictures of my cock, and posted them along with an ad that simply said something like "watch me stroke my hot cock" or something to that effect. Within a couple of hours, I had one legit e-mail from a 35 year old woman, who described herself as petite with big tits that used to watch her boyfriend jack off and really enjoyed it.

Over the course of the next few days, we exchanged a bunch of e-mails and we were both incredibly turned on thinking and talking about it. Finally, one night, she drove up to my apartment and sat down next to me on the couch. We chit chatted and made small talk for a while, but every now and then, she would give me this little smile and glance down at my crotch, as if to say 'ok, let's get the show on the road'.

Finally, I asked her, do you really want to watch me stroke my cock now? And she replied 'yes'. Before I exposed my cock to her, I wanted to make sure it was nice and hard, so I took off my pants, put some oil on my hand and slipped it into my underwear, slowly stoking and teasing my cock as it was still shielded from her view. Then, once I was rock hard and huge, I asked her one more time if she was ready, and she nodded.

With her still sitting on my couch, I stood up, and right in front of her face, slipped off my underwear and exposed a nice, thick, hot cock. She audibly gasped and just stared at it. I could tell she was really turned on and enjoying the experience. From there, for the next 30 minutes or so, I just stroked it for her in all sorts of different positions, letting her get a really good look at it. I had the impression that she wanted more than just to watch, but I didn't really want to fuck a stranger.

Eventually, she started to rub herself through her jeans and then took off her shirt to expose a bra full of D-cup tits. At that point I took it just a little further and rubbed my cock against her cleavage, and then she wrapped her hands around it and stroked it some too. The fact that she was absolutely loving my cock was really turning me on! Then, she asked if she could suck it, and of course I let her. Eventually, she took off her bra and exposed her tits completely and took off her jeans so she could rub herself while sucking my cock and letting my slip my cock between her tits.

After bringing myself close to orgasm so many times in about an hour, I finally had to let go, and told her I was about to cum. She opened her mouth and stuck out her tongue and let me cum all over her tits and face. It was the hottest orgasm I had had up until that point. Something about a perfect stranger coming over to my house, watching me stroke my cock, sucking my dick and taking a load of cum all over her was really exciting.

The next day we traded e-mails about the experience and she kept telling me how much she loved my cock and wanted my cum all over her tits and face again. The next time she came over, she ended up bringing a vibrator and getting herself off several times while watching me. We probably did this off and on maybe a dozen times, and since then I became addicted to craigslist and found a lot more women to have fun with.

I find that posting different ads, other than "Let's fuck" get more responses for the intrigue factor. So, not knowing what sort of response I would get, I posted one about how I always fantasized about shaving a woman's pussy.

Lo and behold, after a week or so, I received a response from a 19 year old woman that lived way out in the boonies who wanted to take me up on the offer. So, after another weeks worth of chatting online, I hopped in my car with some shaving supplies and started the 90 minute drive to where I was meeting her.

We agreed to spend the night in a hotel, but I was to meet her at a local gas station first and then follow each other to the hotel. It seemed a little fishy, but whatever. As it got close to meeting time, she told me what she was driving and what gas station she was at, and sure enough when I drove by I saw her car there waiting for me. I was a little nervous, but finally drive in and said hello. Then she followed me a couple of miles to the hotel.

Throughout that week of chatting online, we talked about sexy clothing, and I told her to wear something sexy and a little slutty, and boy did she ever. She showed up in a short miniskirt, thigh length stockings heels, and a cute little halter top that pushed up her little A-cup tits. She was wearing a jacket over all of that, but once I checked in and we went into the room, she removed her jacket and revealed a hot outfit. Then, she told me the best part. She also wasn't wearing any panties!

I asked her to prove it and she hiked up her skirt and revealed a massive bush. I have never seen that hairy of a pussy, especially on a younger woman. She let me take some pictures so we could do a before & after comparison too.

After the initial nerves wore off, I told her I wanted to eat her pussy first and I went down on her for about 15 minutes before telling her it was time to shave it clean.

I used an electric hair trimmers first, then some warm water, shaving cream and a razor to make it completely bald. Throughout the whole experience, she of course got very wet and turned on.

I took some more pictures of her now bald, shiny cunt and ate her out for another 20 minutes before we were both naked and fucking. I shot my load all over her tiny tits after a blowjob and then left.

Since then, we've had a lot of really dirty chats online, traded lots of pics and met a couple of more times. Problem is she is so far away and I have to get a hotel each time, but it is worth it. She is really kinky and the last time we got together I shaved her again and I fucked her with a huge cucumber wrapped in a condom.