[M]et an anonymous MIL[F] on Craigslist

I’ve lurked here for a long time and finally decided I should make a contribution or two. I grew up religious and didn’t have my first kiss until I was 21. I also swore off meeting people online. That all changed when I moved to NYC for grad school when I was 22.

Initially I tried dating apps, but then I discovered Craigslist casual encounters. This is one of those stories.

Age doesn’t bother me and I’ve always kind of had a thing for older women. You can understand my delight when I came across a post claiming to be a MILF looking for a younger guy. The pics looked fake, but I didn’t get any hits with reverse image search. I also felt I had nothing to lose.

I fire off my email and shortly thereafter, Donna emails me back. She wants to see more of me, so I take a few pics and send them her way. She’s likes what she sees and asks for my phone number. I’m young, stupid and horny, so I give it to her with barely a second thought.

A few minutes pass and then I get a call from a blocked number. Donna has one of the strangest voices I’ve ever heard, and I can only assume that it’s as fake as her pictures and her name. But that doesn’t faze me.

Donna asks me if I’m clean, and I tell her I am. She says she is also clean and on the pill. Donna then tells me exactly how things are going to play out.

I’m to come to a certain Manhattan street corner and email her to let her know I’m close. She will then tell me when she’s ready, I’ll head to the apartment building, press her apartment’s number and she’ll buzz me in. So far so good.

Once I’m at her door, I’m to knock lightly and she will crack it for me. She’s going to be on her knees just inside the doorway, and the apartment is going to be completely dark. Once I’m inside, she’s going to suck me off till I’m hard, and then I’m to fuck her and leave. Of course I say sign me up.

Things play out exactly as Donna tells me. She cracks the door and I enter a pitch black apartment. Moments later, I’m standing there with nothing but my socks on.

Donna loved dirty talk but told me I wasn’t allowed to pull her hair or spank her. While she starts playing with my cock, I tell her how she’s my little cum slut.

I’mm honestly not a huge fan of blow jobs, but Donna has me hard in no time. Maybe it’s just her age and experience, but to this day she’s the best blowjob I’ve ever had. Now that I’m hard, Donna is telling me how much she loves my big cock and asking if I want to fuck her.

After I say yes, she quickly turns around and I get on my knees behind her. I’d had sex maybe a dozen times total before Donna, and her pussy was truly incredible. It wasn’t the tightest in the world, but she was so wet that I just slid right in.

I didn’t mention it earlier, but Donna was wearing these leggings that went up to her thighs. They were a great material that was stretchy enough for me to get a good grip, but sturdy enough that they were never going to rip or tear. I grabbed on tight and pounded Donna’s pussy with everything I could give it.

She loved it and moments later tells me that she’s cumming. Her glorious pussy gets even better than before. After a few more minutes, I tell Donna that I’m going to cum. She asks if I want to come in her mouth or her pussy, and I can’t say no to a good cream pie.

I shoot my load deep inside her and almost as soon as I’ve stopped, she turns back around and takes my cock in her mouth. At this point it’s so sensitive that her mouth sends tingling sensations up and down my body. I have to put my hands on the wall just to stay standing. After 30 seconds or so the tingling subsides, and then it’s time for me to get dressed.

I put on my clothes and am out of the apartment probably no more than 10 minutes after I entered it. A couple minutes later, Donna calls me and tells me how great my big cock felt in her pussy and how she’s so full of my cum. She also adds that her husband will have no idea that she’s filled with cum from my hot young dick. That was a bit of a surprise, since she’d never mentioned being married before then.

Donna and I met up probably 5-10 times total over the next few years. Sometimes I’d email her, sometimes I’d happen across a new Craigslist ad from her, and sometimes she’d call my phone, asking how quickly I could come fuck her pussy. It’s been 2 or 3 years since I’ve seen or heard from Donna, but on those rare occasions I get a blocked call, my breathing still quickens a bit as I wonder whether she’s on the line.

In case you’re wondering, I never did see what she really looked like. I once tried to let a little more light through the front door, but I’d didn’t work.

This is my first post and I’d welcome any feedback and constructive criticism. This might be my craziest story, but I have plenty of other adventures from Craigslist and Reddit that I can share.

Source: reddit.com/r/gonewildstories/comments/b6f80w/met_an_anonymous_milf_on_craigslist