The last person I hooked up with on AdultFriendFinder — though not the last person I met or talked to — was a mistake. In fairness, as I have been typing up these stories many of them were mistakes and a wiser me would not have done the things I did. That said, this story deserves it’s rightful place among the others.
I was on the couples profile that I had with my active friend with benefits. Our intent was to find couples to swing or swap with, but I know she talked to a few single guys once in a while and I talked to a few single girls. Neither of us were opposed to inviting a single person to join us, but we were really picky about the guys and unicorns are rarely found in the wild.
One afternoon I was home — I had taken a sick day / mental health day — and was horny and looking for fun. There was a profile of an 18 year old girl that was relatively new, had a few blurry pics, and a little bit of information. I reached out to say hello and got a prompt reply. They were eager to talk to me, liked my photos, but told me they weren’t into girls and didn’t want to join a couple. She did say that she was interested in meeting up just with me though.
My FWB and I didn’t have a strict rule about that, so I thought ‘why not’ and she told me she would be in the city in 45 minutes. She had just gotten out of her last class — she was still in high school — and she needed to drop a friend off downtown anyway. I said sure, gave her my phone number and address, and waited patiently for 45 minutes.
I got a call from her and she had a sweet, demure, voice. She said she was there and I popped out of my apartment to let her in. She was definitely the girl from the pictures; teeny-tiny, blonde hair, big blue eyes. She was wearing a catholic school girl outfit, had big braces on her teeth, and was carrying a backpack. I was very, very concerned that this girl was not actually 18. I was probably 25 years old, maybe 26, and while I didn’t mind the age gap assuming she was 18, I wasn’t trying to go to prison. As we said our hellos a cab pulled up and another girl in a catholic school girl outfit popped out and walked over to us.
“Oh, that’s my friend, I’m giving her a ride home.” My ‘date’ — I’ll call her Jamie — turned to the new arrival — I’ll call her Laura — “Are you done already?”
Laura responded, “Yeah, he was fast, but it was really good.”
“What happened?” I asked with genuine interest.
“Oh,” Jamie informed me, “I dropped her off to have sex with a guy that lives down here.”
Laura nodded, “He’s older, but he is really good in bed.”
Laura, for the record, was gorgeous. Jamie was cute and petite, but Laura was something else. Dark hair, blue eyes, great smile, very curvy, and she carried herself like a 20-something unlike Jamie who looked and acted more like a 15 year old.
“Well I guess we should all go inside.” The situation was a little more awkward now than before, but… that is the game you play meeting strangers online.
We went up to my apartment and I talked to both the girls. I was trying to understand if this was a common thing for them and why they were so at ease meeting a stranger online and just going into his house less than an hour after connecting. Laura was a regular at this, Jamie was new to it but very eager. They didn’t have an answer as to why they were so chill; they just were. I found out that Laura was only 17 — 18 soon — and I made Jamie show me her ID to prove she was 18 — which she was. I found myself stuck between a socially uncomfortable rock and a very aroused hard place.
I didn’t want to hook up with Jamie. I did want to hook up with Laura. I could hook up with Jamie — and she came her specifically to meet me — but I could not hook up with Laura because she was too young. Being… socially awkward… in situations like this, where I set an expectation for someone, I suddenly felt the pressure of having to perform. So I invited Jamie to my bedroom while I got Laura something to drink and set her up to play Rock Band on my Xbox for a while.
Jamie and I headed up to my room and her entire ‘way too young to be doing this’ vibe continued to grow. I’m sure some perverse part of me was turned on by it, and I hated that part of me. It didn’t stop me though. I told her to strip for me and she did it fast. Her little skirt came undone and she stood there in a cute little pair of panties that matched her outfit. She undid the buttons on her blouse and took off her bra exposing tiny little breasts with big erect nipples. She looked up at me with the utmost innocence in her big doe eyes. She was probably 4’11” to my 6’2” so she had a long way to look up.
I instructed her to lay on my bed and spread her legs for me. I told her I was going to eat her pussy better than anyone ever had or ever would. I pulled off my shirt and got on my knees in front of her and took in the sight. Her pussy looked as small as she was; like I could wrap my entire mouth around it and then some. That was exactly what I did; I kissed around her legs and pussy then took the whole thing into my mouth.
She tasted sweet and I really enjoyed myself with her. I don’t know how experienced she was, but she was enjoying herself immensely. She panted the cutest little moans as I licked and sucked on her clit and she went wild when I slipped a finger into her. A few minutes in and she came for me; her whole body shaking like a leaf. As soon as she calmed down and began to recover I remember looking down at her and thinking to myself ‘that was all you needed to do, she should go now.’
“Can you fuck me now?” She asked innocently.
“I’m not sure.” I was being serious, not playing hard to get.
“Please?” She started to rub her pussy.
“Uh…” I was hard as a rock and, honestly, this was hot even though it should not have been. “Yeah.”
I pulled off my pants and my cock sprung up right away. I’m not huge by porn star standards, but I am well endowed. Better than average length and very thick. Her eyes got wide when she saw it and when she reached out for my erection I was done for. Her hands were so tiny and when she wrapped them around my cock she was able to stack both one on top of the other with room for another hand if she had, had one. I felt like Ron Jeremy or Johnny Sins in that moment. She tried to take me into her mouth, but I was worried about the braces so I stopped her after she gave it a few lollipop like licks.
“You really want this cock in you?”
She nodded at me “Yes, oh yes, please.”
I grabbed a condom from my nightstand and I pushed her back onto the bed and aimed my thick cock at her teeny-tiny pussy. I wasn’t sure I’d fit, but I was too far committed not to try. Surprisingly, she took me in fairly easily. She was very, very wet and very, very horny for me. I had to go slow at first and she was tight, but after a few minutes I was inside and able to fuck her. She kissed me and it was very awkward. I had never kissed someone with braces before and I wasn’t a fan. I started to feel incredibly guilty again; especially when I would look down at her tiny little frame and her child-like appearance would catch me off guard.
I wanted to make it as quick as I could, but I also had this nagging voice in the back of my mind that was telling me — perversely — that I should put on a good show. I wanted to impress Laura, who was downstairs and could likely hear everything, and maybe when she turned 18 we could get together. Yep, that was me, fucking a girl I didn’t want to fuck in the hope that I would impress her friend so I could take her to bed with me in a few months. Not my proudest afternoon.
That said, I fucked the living hell out of Jamie. The idea of having the opportunity to be with Laura when she turned 18 was a tremendous turn on. After Jamie came again I took my turn and filled that condom to the brim. We got dressed, I showed her the bathroom so she could clean up, and I chatted with Laura. She and I had intense chemistry and I was doing everything in my power not to be a creepy piece of shit by asking her if she wanted to go upstairs with me next. Fortunately, I resisted the urge, escorted them both out, and then ran back inside and took the longest — coldest — shower of my life.
I knew that what I had done was not cool on a number of nuanced levels. That night I told my FWB what had happened and we had a bit of a fight about it. It took a few days for things to smooth over, but in the grand scheme of things it didn’t hurt our friendship that much. I never saw Jamie again, but I did stay in touch with Laura. She and I never ended up hooking up, not that I didn’t try. It just happened that she would have a boyfriend when I was single and I would have a girlfriend when she was single.
Regardless, aside from a few couples my FWB and I talked to over the next year or so, that was that. I didn’t meet girls solo anymore and AFF was just a horrible website. Super sketch, and not worth the time or the absurd amount of money the site wanted to use it.
Source: reddit.com/r/gonewildstories/comments/myvteb/she_showed_up_wearing_a_catholic_school_girls
For a moment i though this story was going to end up being a murder story.