In the late 00's I was 19 and home from college for the summer. I had been hoping to get laid at some point but nothing had panned out and the summer was almost over. OKCupid was still a fledgling website, or at least I had never heard of it until I found myself making an account on hopes of scoring.

I get a message from an average looking woman in her 30's. Brown hair, chubby, small boobs. Only one picture, and it's not very good quality. She says "I know I'm a lot older than you but people tell me I look like I'm 19"... I have no idea who would tell her that, because she absolutely doesn't. But my brain is too horny to care, so I kinda ignore her weird comment and make it clear to her that I'm just looking for NSA sex. She says that she's fine with that and almost right away gives me her address. I pull it up on MapQuest and print out the directions. It's a couple towns over but not too far away. I tell her I'm on my way. We hadn't even exchanged numbers—this was all on the okcupid messaging system. I'm nervous and excited to hook up with a woman who is that much older than me. At that age, I felt it was a really big age difference.

I pull up to the house and park in front. She's standing on the front porch wearing blue jeans and a black t shirt. She looks even older than her pixelated profile pic. I'm super nervous, this is my first time to try having sex with a complete stranger I messaged online only a couple hours before. She invites me in... and there's a grandma looking lady on the couch. She tells me the it's her mom and then introduces me. "Nice to meet you." It's so awkward... I didn't know it was gonna be her mom's house. "Mom, we're going upstairs." "OK."

It's not really "upstairs", more like 8 steps up to a hallway, we go to the room at the end. We attempt some awkward chit-chat. It's hard to describe exactly, but this lady is just weird. Almost like she's a little slow. She's showing me the different stuff in her room, like when you first visit a friend's house when you're 10. "This is my [blah blah blah] I got when we went to [wherever]".

I sit down on the bed and pull out some weed and a aluminum foil pipe I had crafted (which I've since learned is probably toxic and should not be used). I ask her if she wants to smoke with me, she says yes. We pack it up once maybe twice, and I was good to go. I lean in and we start making out. She's not very good at kissing, and her upper lip is pretty fuzzy. I pull up her shirt and bra and suck her pink nipples. She has a belly, more than any of the girls my age I had been with before. It's also fuzzy.

But I'm feeling good and beyond horny and I can't keep my dick in my pants for another second. I take it out and she strokes it for a second before I stand on the bed so that its level with her face. She starts sucking, not very enthusiastically, but it's doing the job. I pull a condom out of my pocket and open it. She takes the cue and starts taking off her jeans and panties while I roll the condom on.

To be perfectly honest, up until this point the entire encounter has just been weird and disappointing. She lays back and spreads her legs. Her pussy is shaved, but not freshly, so there's a good stubble (which would eventually become a fetish of mine). I slide in, and it's amazing. Super tight, and not just warm but HOT. At this time in my life I had only had sex with 4 girls, who were all highly attractive teenagers, and many times it was bareback... but even with a condom on this homely 30-something woman's pussy felt so much better than anything I had ever put my dick in before. Some pussies are tight at the front and then open up once you get in. Some pussies are so tiny they feel like they're trying to push you back out. This one was like a glove. It felt like it was milking me. I don't know if she practiced kegals all day every day or if it's just her natural God-given talent. With my previous girlfriends I could normally have sex for a decently long amount of time, but with this lady's mysterious wonder-pussy I'm definitely not gonna last long.

I'm at the point where I'm so hard and close to the edge that I can't make one more single movement without cumming. I've got my dick halfway in her, frozen in an attempt to prolong ejaculation, and I can feel her pussy actively squeezing. I ask her "where do you want me to cum?" —I've always preferred cumming on women. Or cumming in their mouths. And the girls I had dated up to that point had all seemed to be into it, too, so even though I was wearing a condom, in my mind the question was not that crazy.

Until that point, we hadn't spoken a word since we started smoking. She doesn't say anything back. Her crazy pussy muscles are trying to crush my cock. I ask her again "Where do you want me to cum?" She replies in a gutteral whisper, "I want you to keep fucking me" ... So I do! I probably don't make it more than 10 pumps and I'm blasting into the condom, but still trying to pump her as long as I can per her request.

knock knock knock... Mom??

"That's my kid."

Oh God. I hope I don't have to meet her fucking kid now. I can't get my pants on fast enough. He's continuing to knock and call for her. She's blowing him off, maybe she's stoned and doesn't know what to tell her kid is going on. But he keeps on knocking. We finish getting dressed. "That was great! But I gotta go. See ya!" and I practically jump over this little boy to escape down the hallway down the stairs and practically run out the front door and drive away as fast as I can.

How can an experience be so simultaneously bad and good at the same time? But either way, I'll never forget that woman's magical pussy, and all in all this is a fond memory for me. My very first weird internet NSA sex.