My partner was out of state a few years ago and I (now 34F) was lonely, horny and bored. This was when Craigslist personals used to be more of a thing, so I’d surf Craigslist endlessly at work trying to figure out if I was connecting with someone both attractive and sane. One of the personals got my attention. I can’t remember the text exactly, but it was clear this was a confident, intelligent person who could put a few sentences together. He went by “Jon”, which I doubt was his real name. I responded to the ad and we began a very naughty back-and-forth while I was still at work. I was still pretty nervous about fucking complete strangers at that point and at the same time the thrill was electric. I’ve craved that high ever since.
Till this day I remember exactly what I was wearing — a cute blue and white floral, lacy dress that kinda ratcheted up the “innocent girl next door” factor. We quickly decided that he would book a hotel that evening and that we’d meet each other for the first time that very day. My heart was racing from the adrenaline, and I went to the bathroom multiple times to clean myself up because I was just creaming myself all over the place. I told Jon so, and he instructed me to send him a picture of my soaked underwear. I happily obliged.
“When you come to the hotel tonight, I want you to get here without your panties on,” he texted me.
I remember walking into the lobby, my dress swishing around my bare pussy, thrilled that only he and I knew that I had nothing on underneath. We had swapped descriptions of what we were wearing, and decided that I would check in, get the room key, then walk confidently towards the elevator where he would join me. I would then leave first, enter the hotel room and leave the door ajar so he could come in after. I got into the elevator and we were just eye-fucking each other at that point. He was about 6 foot, well built, with a big devilish grin.
Trembling, I walked down the long hallway to the hotel room and did what he said. I had barely set my bag down on the carpet when he came through the door and pinned me to the wall, his hand around my throat. With one swift movement he reached up under my dress and shoved his fingers into my dripping wet pussy.
“Good girl,” he whispered, “you took your panties off like I told you to.”
He fingered me while pressing me against the wall, and I gasped and squirmed beneath him. Then he forced me to the ground and unzipped his pants. I fumbled with his belt buckle and finally got it undone. His hard cock came loose and he laughed when he saw my shocked expression. “You should see your face right now!” He chuckled.
I took his cock in my mouth greedily and almost choked. It had been a while since I had a thick dick in my mouth. I licked and sucked it urgently, trying to get all of it in my mouth. Then, Jon pushed me backwards and threw me onto the bed, face down. He fingered me again and again, and I could hear him getting out a condom with his other hand. He flung it onto the bed: “open the condom for me,” he demanded. I was shaking and almost delirious with desire at this point and could barely rip the wrapper open, but I did. He rolled the condom onto his cock and pushed himself inside me with such force I cried out.
“Oh… my… god….” I could barely eke out words as I heard his balls slapping against the outside of my pussy. Every thrust vibrated through my entire body. I remember him pressing my head down into the bed as he rode me roughly. I still had my dress on and it was riding up around my waist. He didn’t stop pounding away at me for quite some time, and I think I came at least twice – I could feel myself wailing and arching backwards and digging my fingers into the sheets while Jon pulled my hair back and I could feel my pussy tightening around his cock.
Suddenly, Jon paused and laughed. I wasn’t sure what had happened and I was so overcome at this point I couldn’t even turn myself around. He turned me over and said, “Babe, you’re bleeding.” He had basically fucked me so hard I’d started to bleed. I couldn’t feel it yet but I knew I definitely would the next day.
I was so mortified that I was bleeding that we both paused the session to clean up. Jon was very amused but kind about it. I shed all my clothes, which were sticky with sweat, and just sat naked in one of the hotel’s armchairs, catching my breath. Jon and I sat there for a bit, cooling off and making small talk, but while we had plenty of sexual chemistry, I didn’t find him particularly engaging and the conversation soon fizzled out. I was relieved when he said he wasn’t going to spend the night. The hotel was pretty nice and I ended up having a nice suite to myself overnight that we had split the bill for. Not a bad experience for my first no-strings-attached evening since getting married, and after this I would develop a lot more confidence and precision about my sexual appetite.
(The bleeding never did happen again! Not that I want it to – I was fucking sore for days and am *not* into blood at all.)
Source: reddit.com/r/gonewildstories/comments/n43w6v/i_f_fucked_a_random_guy_m_from_craigslist_the