OK, try your best not to get judgemental on this one because it isn't my usual MO, and none of it was planned, it just sorta happened. Anyway...
Years ago, I put up some kind of a post indicating that I was looking for a girl. I honestly don't remember the post I put up, I just remember that I got a response from a girl claiming to be 18. I was skeptical. Then she told me she was looking for 'help', and I got REALLY skeptical. Still, I was willing to play along, and there are a lot of kinds of 'help' that people can need, so whatever, I let it play out. Eventually she explained she was trying to get painkillers for her friend, who she indicated was in legit pain.
Now, this is absolutely where I should have stopped. Not only is this potentially a set-up to get robbed, and it's DEFINITELY a set-up for a police sting operation. As luck would have it though, I had recently broken a bone and had a fuck ton of pills left over because the doctors used to hand them out like candy and I never particularly liked them. Also, the 18 year old girl sent cute pics and explained she was a virgin, and that I could potentially take either her anal or vaginal virginity in exchange for enough pills, and at that point I was unfamiliar with thirst traps and catfish, so I was like, "Golly, this sure sounds like a sweet deal". If this were a movie, right now is where you hear that music that lets you know the lead character is about to die.
We set up a meeting in a cheap-ass local motel. This was in another state, and it was snowing like crazy. I was aware enough to know there were at least a few kinds of trouble that could be headed my way, but in hindsight, I realize there are about a millions terrible things I opened myself up to here. Regardless, my heart was in my throat. I hadn't done many motel-based rendezvous in my life at this point, so the idea of meeting a stranger for sex was unnerving by itself. Then I started to think of all the possibilities of how it could go wrong, the least of which was being stood up. Then there was a knock on the door. I looked through the window and saw a single, very cute girl, shivering in the snow, apparently alone. I let her in.
Turns out, she was totally awesome. Not a cop, not a mugger, nor a cult member looking for fresh sacrifices. Nope. She was a sweet girl with a pretty normal life. She was Caucasian, pale skin, dark brown hair. Brown eyes, small nose, big eyelashes. Tall with petite breasts and a healthy round ass. Genuinely very pretty, you'd totally want to date her on looks alone. Then we got to know each other. We both made obligatory speeches about not having done 'this sort of thing before', and she explained a bit more about her friend who needed the medication. Nothing super specific, but it sounded like a legit enough chronic pain conduction. She also mentioned that, although having recently turned 18, she was still in high school and had just won an award at a debate meet the previous weekend. I cannot tell you what a turn-on that was.
After we got to know each other a bit, we talked terms. Before meeting we'd exchanged a lot of messages and anal sex and vaginal sex both came up. She had waffled between the two, but ultimately landed on vaginal. When she was in the actual room though, she changed her mind at the last minute to anal. I'll not lie, I was elated at the notion of either, so it almost didn't matter in terms of satisfying me. I was, however, not super experienced with anal at that point, but I'll get to that in a minute.
When we finally agreed on anal, I asked her to strip fully nude. She said something like, "Uh, do I have to?' and asked me why. I nearly laughed, not in a mean way, I just couldn't believe it needed explaining. "Well, it's because you're hot, and I want to see you naked. It's a turn-on.". She replied with something like, "Oh", and then proceeded to strip down. She had a very sexy body. Flawless skin. Perfect pink nipples and delicate handfuls that I barely got to see as she immediately assumed the doggy position. And there it was. Her wide, white, virgin ass, pointing right at me.
I was already hard but knew enough to lube her up before diving straight in. What I didn't know then was that there is actually such a thing as TOO tight, and I only spent a minute or two fingering her asshole with the lube. To any of you taking notes at home, buy a high-end anal lube, and take your time playing with that virgin butt. Be gentle, and wait for it to relax around your fingers. One at a time. Work your way up to two. You get the idea. I did none of that and tried to push in as soon as she was lubed up. When you see this scenario in porn, you always see some poor girl scream in agony as her unprepared anus is forced open by a monster cock. Well, in this scenario, my cock was as solid steel...but her tight ass was pure titanium, and my shaft got bent in half. Easily one of the most painful things to ever happen to me. I was seeing stars. My eyes were watering and I did my best not to cry out like a little bitch. The girl was being very chill and wasn't even looking back at me, she just asked me what was going on. I told her I'd need a minute while I tried to figure out my next move. I took a minute and let the blood pressure die down, but I honestly thought I might have done some serious damage to he veins. The idea of going home in a penis cast seriously crossed my mind. But then I looked at that gleaming white virgin butt, and I did my best to walk it off mentally. I'm a big fan of anal, and I'd never been with a virgin on any level, let alone taking a girls anal virginity. And she was sooooo cute. I just couldn't stand the thought of losing out on the opportunity. So, I took some deep breaths, applied a LOT more lube, and went for it.
Despite the pain, and the awkwardness, I can tell you honestly I've probably never been as aroused as I was while sodomizing that adorable debate team captain. I wish I could say I fucked her hard for hours, but I came in her asshole almost immediately, and she'd only signed on for a single boink. We didn't even kiss, and her clothes were back on before I'd even lost my erection. Still awesome. That said, my dick hurt for DAYS after, and I had an enormous purple bruise on one side. Absolutely worth it, but I do wish I'd been more patient with that first entry, this could have been a way different story. Oh well.
One funny coincidence I remembered from this one was the fact that I moved to California just a few months after this. The girl and I actually stayed in touch for a while, and she reconnected with me right after I left. The irony was, that she had apparently just been in California, and I got the impression she was originally from there. So, had the timing worked out, we might have hooked up again just for fun. At least I like to think so. Also just kind of funny that she had just left Cali right before I was planning on moving here, because the state we actually met in is fairly far removed from CA.
As with all my stories, it is 100% authentic, I am doing my best to protect the identities of innocent civilians, so I will never give out names or photos or other personally identifying info, but if you have any other questions, let me know. Also, for the record, the circumstances of this story really were a one-time thing for me, and although I will happily fuck cute girls in the ass anytime they ask, I do not have any painkillers, and I will not reply to anyone inquiring about any kind of deals like that. It was a weird situation, not a lifestyle.
Oh, and one more thing - no one should ever, under any circumstances, repeat any of the stuff I did here. I'm serious. The fact this girl was real, actually a girl, and not a maniac or disease-infested drug addict or a cop or a fucking vampire, all of that is a magical fluke you should never expect to repeat. If a stranger ever contacts you offering an adorable virgin ass for anything potentially illegal, you are 100% being tricked. I honestly still barely believe this one really happened, and the only reason I do is because I nearly broke my dick trying to penetrate the world's tightest ass.