[FM] Craigslist Hookup with a 22yo mom of two

So this goes back awhile….I’d say 15 years and I was in my early 30’s. Back when Craigslist was very relevant and had personal ads. I traveled a ton for work and would usually be in a town for at least a couple weeks, sometimes a couple months. My routine would be to hit the local CL personals a week or two before arrival on a new assignment. Most of my hookups came from in-person meets, but occasionally something nice would pop up on CL.

I met Cassie in the platonic personals. She was a bored stay-home mom of two young children looking just to chat and get to know someone. We emailed back and forth a bit and the discussion quickly turned to her unhappy marriage. Much of which seemed to stem from an unhealthy sex life. Her husband was raised very religious and they did not have any type of sexual relations before marriage. They started dating her junior year of high school and got married shortly after graduating. She had been with a couple guys before her husband, but he didn’t know that. They waited until marriage to have sex and he had never been very interested in it even after that. He was also very vanilla…..they had only ever had sex in a bed with the lights turned off. Almost always missionary. Did not like talking about it and was not open to discussing why she wasn’t satisfied. She went on and on about all his performance issues, his aversion to her using toys, and mostly that she was utterly unsatisfied sexually and thinking about leaving. Even mentioned that his precum tasted so bad she couldn’t even suck him which she enjoyed doing to her boyfriends before. He had never gone down on her or even touched her pussy with anything but his cock.

So we chatted off and on for a week and I would tease her with some of my stories. I had a ton of experience being single and traveling for over a decade. She seemed rather unsure about stepping out and actually cheating, but I could tell I had piqued her interest with some stories. She also seemed very shy about her body, but she looked terrific in the clothed pictures she had sent. She shared some of her fantasies, one of which involved meeting a stranger a giving them blowjob to completion. I mentioned that several ladies had said my cum tasted very nice and she said she might like to find out. It took a few days for her to arrange for a relative to watch the kids while she “went to a dr’s appt”. We agreed to meet at a park that was part of a busy tourist attraction where there wouldn’t be anyone to recognize her. It was a very warm summer day and she was wearing a really cute yellow dress that cut off at the knees. She looked better than her pics actually…5’6″ and 150#. Maybe a little chubby but also very athletic, muscular legs, very small breasts. I told her she looked amazing and she was quite shy about the compliment.

We sat at a picnic table and nervously talked for a bit about random things I really don’t remember. She was very chatty, nervous, flushed face, playing with hair. At some point I asked if she felt comfortable enough with me to go sit in my truck in the A/C. I told her I had dark windows and a windshield shade so it was very private. Maybe we could make out a little. She sat there for a minute thinking and finally said ok. We changed venues and with the A/C cooling things off we continued to chat and I could tell she was quite nervous. She kind of had her hands clasp in her lap and I kept looking down at them because it almost seemed like she was putting pressure on her crotch area. Also was looking because her dress was hiked up a bit exposing legs and I’m a horny man. She could tell I was watching her and I asked if she was horny….and I remember her expression of almost like being caught and blurting “I’m worried I’m dripping all over your seat”.

I laughed and said that would be so hot if it did! Of course I then had to ask if that meant she wasn’t wearing panties…to which she pulled her skirt up to reveal an absolutely beautiful shaved puffy lipped pussy. I complimented her and she pulled it back down quickly kind of embarrassed like. I figured it was time to make my signature move of going straight to kissing her neck and she exhaled heavily. She quickly turned her head to meet my lips and became very aggressive kissing and flicking her tongue in my mouth. She grabbed my head and pushed me down her neck and chest where I kissed as much of her breasts as I could while she was dressed. I ask her if she wanted me to kiss her gorgeous pussy and she pulled her dress back up and said “please”. She spread her legs a little and while the angle was a bit difficult, I could get my mouth and tongue on her clit very nicely. She was absolutely soaked and my seats were definitely getting stained by her juices. I tongued her for maybe a minute until she started moaning and shaking violently. When it seemed to subside and I thought she had fully climaxed, I started to slow down a little but she pushed my head down and said “jesus don’t stop”. I’m generally dominant but I found this so hot. She continued to cum for what seemed like a minute or more and finally said she needed a break. My face was quite wet but she pulled me back up to kiss again and she licked and tongued me to get all of her pussy juice off my face. My cock was so hard and uncomfortable in my pants at this point, I sat back in my seat and pulled it out of my jeans to give it some relief.

She seemed quite happy that I was so hard and she kind of bit her lip as she reached over and grabbed it at the thickest part. I’m not huge or anything but it’s a nice cock…she said it was by far the biggest she had ever held and I could tell by the look in her eye she wanted more. I asked if she still wanted to suck off a stranger and she said yes…but she had swore to herself she wasn’t going to do anything sexual today. I said well it’s kind of too late for that don’t you think? She laughed and stroked me for a bit…I was so turned on it wasn’t going to take much to make me cum. I told her if she stroked it harder she’d make me cum….but instead she leaned over and immediately throated as much of it as she could. Her mouth felt amazing and after a minute she stopped and said my precum actually didn’t have any taste at all and she could suck me for hours. I told her to just to whatever she want but then she kind of flashed back to reality and knew she couldn’t be gone all day. She said she wanted to make me cum and I told her to just use her hand a little to stroke it while she sucked. I warned her that I usually have big loads and she kind of made a mmmmmm sound. It took only a minute or so before I was cumming hard in her mouth and she choked a bit but swallowed it all. She made a AHHHHHH sound after swallowing and I asked if that meant it tasted good. She said yeah…mostly no taste at all but she loved that I came so much. She continued to stroke it slowly and watch as more cum would start to leak out she’d lap it up with her tongue. Eventually the cum stopped and she sat back to relax.

I’m always good for a couple rounds and if turned on I will stay very hard even after cumming. She noticed I was still hard and that it wasn’t subsiding at all. Apparently nobody she had been with before could go more than one round at a time. I started stroking it a little to show her how turned on I was and she reached over and grabbed it again. But this time after stroking it a little she climbed up over the console and straddled me, with her pussy lips laying against my cock. I reached around and grabbed her tight ass while we started kissing, encouraging her to grind on my cock which she complied emphatically. She said kissing made her so horny and she was going to cum easily like this so I told her to grind on me as much as she wanted. We kissed through her orgasm with her moaning in my mouth and legs shaking at my sides. I wanted to fuck her so bad but before I could even say the words, she pulled my cock up straight to her pussy and very slowly slid down on it…making a face that looked of part pain and part ecstasy. She was extremely tight…almost painful for me even, but so slippery it had no problem going in. She moved slowly up and down my cock, stopping every dozen strokes or so to grind on me while balls deep and then she’d go back to long slow strokes. After maybe a dozen sets of that she had built herself up to a screaming orgasm and started grinding her clit fast and hard with me buried deep inside. She continued this routine over and over …giving herself several more orgasms. At one point while she’s riding slowly and taking a break from kissing me, I look over and notice a huge wet stain on my passenger seat. I can feel my ass and crotch are also soaked and have no doubt I have a matching stain on the drivers side as well.

Finally after another orgasm she seems to have satisfied herself and says she’s going to have to get home soon….but wants to know if I can cum again. At this point she’s just slowly riding up and down, breathing hard, and holding on to the back of my neck. I told her it was taking everything I had to hold back this long. She gave me a sexy grin and instantly her energy came back…she picked up the speed of her strokes and began slamming down hard on my cock. At this point push up against her so she’s really taking every last inch I have and this not only surprised her it put her straight into an deep moaning orgasm which in turn instantly put me over the edge. As I started to cum she stopped balls deep and went back to grinding to complete her and my orgasm at the same time. She collapsed onto my chest and we just sat there with my still mostly hard cock inside her. When she finally dismounted I could see the cum running down my cock and balls onto the seat. What a mess but holy shit what a good time. She cleaned up with some paper towels I had in the truck and I noticed the bottom of her dress was soaked in the front where it had been picking up her juices while she was riding. It was also wrinkled all to hell and her hair was an absolute mess. As she walked away I hoped she could get home without anyone noticing she looked a bit dis-shoveled to be just coming from a dr. appt.

But she made it home fine. We met up several more times but went to my hotel during the day whenever she could come up with an excuse to get free. One of my all time favorite hookups as we just fit together amazingly well. I love being ridden slowly and love watching a woman orgasm over and over.

Source: reddit.com/r/gonewildstories/comments/101u9yx/fm_craigslist_hookup_with_a_22yo_mom_of_two