People who have hooked up with someone much older/younger on craigslist or dating site, how was the experience? (NSFW)


Yeah, this story goes back a few years, to my college days. One summer, I stayed in town to do research for a professor of mine, and had just been dumped by my girlfriend of three years when the summer started. So, feeling lonely, I was scouring the web for porn almost nightly. And not the tame, Pornhub-y stuff, mind you. I was getting weird with my fetishes, which necessitated visiting odd sites filled with pop ups and such. Anyways, I was getting ready to escape to my mastubatory paradise when I accidentally clicked on one of the ads. IIRC it said something along the lines of "HOT MILFS wanna GET LAID." Whatever, that doesn't really matter, does it? My first thought was to close it immediately and get back to my business, but that nasty little thought crept into my head "What if?" I mean, I had heard these things were scams, and I wasn't dumb enough to give my credit cards or use my actual name or email in creating an account or anythings, so I figured "What the hell?" and went for it. Turns out I didn't need to use any substantive personal info to set up the account, which ended up being a nice surprise.

After setting up the account, I figured it'd be a little bit before I'd get any profile hits or whatever from anyone, so I went back to whips and chains galore in my other browser window. To my surprise, though, after just a few minutes, I got an alert that someone had sent me a message. Naturally, the exciting prospect of real sex versus using my hand immediately had me at the other window. I eagerly opened the message from Cougergal97 and it read "Feeling lonely tonight. Where are you from?" After responding to her, we got to chatting a bit and eventually agreed to exchange pics of ourselves over email (again, using throwaway gmail accounts) before deciding when and where we'd meet later that night. In just a few short minutes, I had set up a fake gmail account and had received an email from my potential fuckbuddy! My heart pounded as I opened up the message and I nearly died when I saw from the attached picture that this woman was not ugly in the least. I mean, she had definitely seen better days, but she still looked good, and she seemed to be a reasonably fit 40-something, so I was in. I switched back to the other site and let her know, and then went straight back to the picture. I stared in amazement and excitement at the woman I would be having sex with, but I couldn't shake this creeping feeling I had seen her before. I couldn't figure out where exactly, but there was an odd familiarity in her face. Figuring she probably just had one of those faces, I closed the window and went back to see I had received a message from my potential partner for the night. It was determined that we'd meet up that night in a parking lot that was pretty out of the way, figuring there wouldn't really be anybody there after dark.

Excited by the prospect of sex after what had seemed like the longest weeks of my life, I felt shudders of nervousness trace their way down my spine as I prepared for my big night. I couldn't believe my luck! I was going to get laid tonight! Having finished getting ready with about 15 minutes until I needed to leave my apartment, I decided to take another look at the picture she had sent me. Again, I just could not shake the feeling that I knew this woman from somewhere, but my mind raced and struggled trying to pinpoint exactly how I knew her. Maybe a friend of a friend or something? I was considering going on facebook to see if she had been in a friend's picture or something (stupid idea, I know, but I felt I had maybe met her through a friend or something), but saw that it was time for me to go, so I abandoned my investigations for another time.

Once I got to our agreed-upon location, I nervously approached the only other car in the parking lot, a foggy, beaten-up Camry. I tentatively knocked on the window, and said "Cougergal97?" The woman inside the car nervously said "Yeah... Are you here to, you know...?"

I told her I was, and she opened up the door to the back seat of her car and said "Get in the back, I suppose." I obliged, and a moment later she joined me in the back. Now, even in the poor lighting, I could tell that there was something off about the woman who was there with me. She was much larger than she had been in the picture she sent me, like, we're talking a solid 50 to 60 lbs more. What's more, she seemed to be like 60 years old! I was a bit thrown off, but I thought that I'd give her the benefit of the doubt. Maybe she just didn't have any recent pictures of herself.

I knew I was going to have a tough time getting aroused here, but I was desperate for sex, so I was still going to try, obviously. She noticed my trepidation, and said "Yeah, I know the picture I sent you was from a while ago. I'm sorry, I was just afraid you might not be in if you saw me, you know... Like this..." I told her it was fine, but every second I spent with her in that car, I knew the chances of me being able to enjoy this were diminishing. At that moment, I knew I wasn't going to have sex with her, but I figured I might be able to enjoy head or something. I offered to go down on her first, but she refused and told me she'd do me first instead, so I let her.

She slowly undid my belt buckle and zipper, I think trying to make it sexy or whatever, and then lowered her wrinkled face to my cock before inserting it into her mouth. Never have I been one to complain about a blowjob's quality, as I'm just not attractive enough to be complaining about the sex I'm getting in general, but this one was truly an exception. I'm talking AWFUL here. Like, teeth grinding against shaft and tip, coupled with an overabundance of spit and the nastiest slurping sounds coming from this woman whom I was growing more and more disgusted by with every passing moment. After about 3 minutes of this god-awful experience, I stopped her and told her I'm sorry, this just isn't going to work. I zipped my pants back up and put my belt back on before going back to my car and leaving.

On the drive home though, that nagging sense of familiarity I had been experiencing earlier started creeping back in. I KNEW I had seen this woman somewhere; interacting with her made me more convinced of that than ever. Still though, I just could not figure out where it had been. By this point, it was eating away at me like crazy, but try as I might, I could not figure out who it was. By the time I got home, I had thought so hard about it that I had burned myself out of thinking anymore, so I decided to go on reddit to look at some cute cat photos before retiring to bed for the night. An hour or so later, as I lay in bed drifting off to slumber, it hit me.

It was your mom all along.

PS. This was inspired by another very similar post on another thread like this that I couldn't find. I wanted to link it, so if someone else can find it and link it here, I'd suggest reading it as it's a better read as I recall it.

/r/AskReddit Thread