Hi there! If you havent read my [first post](https://old.reddit.com/r/gonewildstories/comments/huagjp/my_first_comic_con_with_a_fuckbuddy_her_first_3way/) I would recommend doing so, because these stories are all at least somewhat interconnected. I also gave background info on me in the first one, so if you wanna know a bit about me go check that out.
If you dont care about any of that and just want the smut, skip to where it says “SEXY STUFF STARTS HERE.”
Anyway, this all took place starting about two months after the events of my first story. Mandy and I stayed in touch and would sext several times a week, in addition to just chatting and talking as friends. We would also make plans for what manner of debauchery we wanted to get into at our next convention.
Now, it probably wont surprise you to find out that Im on fetlife. This story starts when I happened across a personal ad on fetlife, from a girl in my city looking for play partners or a sort of kink mentor, as she was new to the scene. Her username looked familiar to a name used for by a girl I knew from my friend group around various cons. I looked at her profile, and sure enough, it was her. Her name was Jenny (not her real name) and we had met through mutual friends at cons and had hung out as part of group hangouts and such, but had never directly hung out or really been “friends” just the two of us. We were more like fairly good acquaintances. One thing I DID know about her, was that nobody in our friend group knew she was into kink. It came as a surprise to me, too.
Jenny was very short, very curvy, ginger with waist-length hair and freckles, and absolutely huge breasts that she liked to show off by using corsets as part of her costumes. she seemed very very innocent to the outside observer.
Anyway, she *had* posted a personal ad, so I messaged her. I basically told her I was surprised to see her on there, but it makes perfect sense that she was into kink. I told her I liked a lot of what she was into based on her profile, found her very attractive, had been into kink for many years, and would love to show he ropes. (pun very much intended.)
She responded with embarassment at first, but then she replied that she had checked out my profile and she was… well, very interested, to say the least.
Our schedules didnt match up for a good while so we decided we would meet up and play for the first time at the local convention that happened downtown in about a month. We went over all her interests, limits, safe words, etc. I basically gave her a crash course in intro to kink while getting a feel for what she would want to try and what she was and wasnt into, etc.
The convention arrived, and it was mid afternoon on Friday by the time she got there. I had already checked into my hotel, gotten my badge, and checked out a couple panels. She texted me that she was here, but was with a group of our mutual friends. Important to note, none of our other friends knew she was kinky, and she wanted it to stay that way.
**SEXY STUFF STARTS HERE**
I met up with them and we roamed around as a group for a bit. She was dressed as a sailor scout, and I was dressed as The Doctor once again. I made sure she and I walked in the back of the group, so that I could take advantage of the short sailor scout mini skirt to grope her ample ass, and even slip a finger into her panties now and then. I was also able to confirm she was wearing the buttplug I had told her to wear. I could see her getting more and more flustered, and I loved it.
Eventually I decided shed been teased enough, and it had been long enough that the group wouldnt suspect anything, so I made some excuse about the two of us checking out some panel and we headed off back to my room. We got in an empty elevator to head down to the ground floor of the convention center, and the instant the doors closed I had her slammed up against the wall making out with her. one hand slid under her top and the other grabbed her ass as we kissed. as the floors dinged away I moved one hand around to the front of her panties and began teasing her clit, making her clap her hand over her mouth to stifle her moans. just as she was about to cum, we reached our floor, i slid my hand out of her panties, grabbed her hand, and pulled her along, red faced and panting, as the doors opened.
We made the short walk to my hotel right across the street and got in the elevator there. This time when the doors closed, I shoved her to her knees and pulled my cock out. her jaw dropped and she tried saying something about it being bigger than she expected, but she didnt have time to fimnish as I shoved it down her throat. my room was on the 30th floor and this hotel was largely empty, so we had a nice, long, uninterrupted elevaor ride for me to fuck her face. When we got to our floor and doors open, she tried to pull back, but I held her down and kept fucking her mouth. The doors opened and no one was there, so I stood there in the elevator, doors wide open, and kept fucking her mouth. i kept making her gaga and choke as the doors closed, and this went on for several more minutes. Only when the elevator started moving, having been called to another floor, did I let her stand up and put my cock away. we ended up only going a couple floors down, someone got on, went down one more floor, and they got off. We went back up to my floor and I lead her to my room.
As soon as the door was shut behind us, I slapped her across the face and shoved her face first into the bed by a fistful of her hair. I slid her panties down and tossed them aside. I spanked her ass, softly at first but growing harder with each slap, as her ass turned more and more red. She was very fair-skinned (gotta love gingers) so her ass became VERY red, very quickly. I grabbed some leather cuffs from my bad and cuffed her hands together behind her back. I slid a ball gag into her mouth and secrured it. she was now bent over the bed, helpless and dripping wet, and I wasted no time in splitting her in half. I stoof behind her, put one hand on her hip, and slid into her in one thrust, prompting her to scream bloody murder as i stretched her out. She had a really tight pussy. Like, a REALLY tight pussy to the point where it was almost a problem. im only slightly above average and she could barely take me all the way. from the sound of her screams youd think I was tearing her in two, and that was exactly what I wanted.
I grabbed her hips and started slamming away without mercy, pulling all the way out to the tip on each stroke, and then slamming it back in full force. she began cumming almost immediately, and according to her, she didnt *stop* cumming until I finished. i slapped her ass as I pounded into her, telling her what a dirty slut she is and how I was going to ruin her tight little pussy. Her screaming and wild bucking soon drove me over the edge, and I unloaded everything into her tight, spasming cunt.
After taking a few minutes to recover, I grabbed some more toys from my back, went back over and carefully removed the butt plug. I lubed up a small dildo, and began working it into her ass. Over the next ten minutes or so I lubed her ass up nice and good, and worked up to a bigger dildo, then another bigger one after that. By then I was ready to go again, so without a word I slid the dildo out and slid my cock in. After a couple minutes of slow gentle stroking to let her get used to it, I was done showing mercy and started slamming her ass full force.. She shrieked and tried to squirm away, but of course that just egged me on and made me fuck her even harder. After about 20 minutes I flipped her around from doggy style to missionary, her hands still cuffed behind her back. I made her look me in the eyes as I stuck it back in her ass, and choked her with one hand while I used a vibrator on her clit with the other hand as I pounded her. Soon after I buried myself balls deep and came into her ass. After catching my breath for a moment, I slid out, took off her gag, and told her to clean off my cock, which she did with gusto.
After we laid together and cuddled for a bit, we got ready to go back over to the con. I had her put the buttplug back in, and she asked where her panties were, but I told her she wouldnt be wering any for the rest of the day. After that we went back and found our group and roamed with them for a while, then Jenny had to go off to be in a panel she was part of. After that we both had stuff to do so we wouldnt see each other again till the next day. She was driving in from her home just outside the city each day, and she was giving a ride to a friend so she couldnt stay in my hotel room.
Saturday was fairly uneventful for the most part. We didnt have a good opportunity to sneak away from the group and there were a few other things on the schedule we both needed to go to, so it wasnt until the con was almost ready to shut down for the night that we had a chance to sneak off. We managed to find our way to a corner of the convention center that wasnt being used for anything at that time. We tried to go into one of the meeting rooms but they were all locked. She said she was counterpointed we wouldnt be able to do anything, but I laughed and just lead her to the most deserted-looking part of that floor, a hallway in the corner on the outer edge of the convention center, and pushed her to her knees and told her to get worshiping.
Like an obedient slut she took my cock in her mouth and sucked it like it was the single most important thing shed ever do in life. After I was good and ready, I pulled her to her feet, pushed her up against the floor-to-ceiling windows that ran along that hallway and overlooked the city just two stories below, bent her over and shoved myself into her. she tried to cover her mouth but I was having none of it. I wanted to her this bitch *scream.* I grabbed her wrists and pulled her arms behind her as I pounded her increasingly wet cunt. i reached around and lifted her shirt up, so her bare breasts were pressed against the glass as I used her. I took my free hand and reached around to tease her clit as I fucked her, making her whole body quiver and shake. I fucked her for what must have been another 20 minutes and I have no idea how nobody heard us and came to investigate. soon I was ready to cum and pulled out, spun her around, grabbed a fistful of her hair, shoved her to her knees, and shoved my entire cock balls deep into her mouth, and came straight down her throat.
We tidied up a bit and went back to the main convention area, and that was the last sexual stuff we did that weekend.
Fast forward 3 months and its another convention. This time both Jenny and Mandy are with me, and theyre both staying in my hotel room with me. Whats more, none of Jenny and my normal friend group is at this convention, so we dont have to worry about hiding her kinky side. the 3 of us were sharing a 2-room suite with Jack (from the previous story) and a few good friends of mine; Cameron, Rick, and Ben, as well as Jenny’s friend Allie who was one of her few friends that knew about her kink. (All names changed to protect privacy) I had had 3ways with Cameron and an ex gf of mine before, but I didnt know much about whether Rick and Ben were into kink or anything of that nature.
Anyway, Friday night of the con, all the panels and events of the convention itself were over for the night at 1AM, but this was a huge party con and so everyone always drank and partied and shit in all the hotel rooms that were attached to teh convention center. Me, Mandy, Jenny, Allie, Jack, Cameron, Rick, and Ben, were all drinking and playing truth or dare along with a few friends; Tom, and Nicky. Cameron had a truth or dare app on his phone that automatically selected the dares so nobody had to feel like a creep for being the one to suggest a pervy dare, and nobody got singled out to be targeted for dirty dares. The app also automatically raised the “naughtiness” level of the dares every few rounds. If you didnt want to do a dare you were given, you had to take a shot.
Things were progressing along nicely. People were nicely buzzed but nobody was wasted or super tipsy. All the guys except Rick and Tom were down to just boxers, Mandy and Nicky, were down to bra and panties. Allie had lost her shirt but still had bra and jeans. Jenny was completely naked but was under a blanket. Jack got the dare to put his hand down Nicky’s pants and hold it there till next round. Mandy got the dare to make out with Cameron for 2 minutes, during which time they got really into it and he fingered her a bit. others complained but mandy said the dare just said they had to make out; it didnt say they couldnt ALSO do more.
Nicky got the dare to let everyone in the group grab her ass. Cameron announced the app was rasing the dirtyness level again and it was Allie’s turn. Her dare was to pick someone and have them suck on her nipples for 30 seconds. She didnt want to and so she took a shot instead.
Jenny got the dare to sit on my lap till the next round, both of us naked. Rick got the dare to go down on Jenny for 1 minute. As he did so, I thought “fuck it, we’ve come far enough” and spoke up.
“Hey guys, so… do we all wanna just drop the pretense and just start fucking? We all know thats where this is headed so why not just skip the middleman? If nothing else, I know for a fact that Jenny and Mandy are down to get gangbanged. I have condoms, lube, and some toys in my suitcase.”
After some discussion and mulling it over, Ben and Allie bowed out because they werent really comfortable with going as far full on group fucking, but Allie wanted to stay and watch to make sure Jenny was ok. Everyone else said they were in.
A brief description of people: Cameron was a tall, skinny black guy with short dreads and a pretty decent sized cock. Rick was a muscular white dude with blond hair and a big beard. Tom and Ben were both white guys with average builds, clean shaven, short brown hair, and average sized dicks, though Ben was a bit taller than Tom. Allie was a tiny little Asian chick with a short bob haircut, and fairly flat chest but a nice ass. Nicky was a tall strawberry blonde with chest-length straight hair, a tiny waist and big hips, huge boobs, with an average ass.
I went over a few ground rules for everyone, what the safewords were, condoms were required for penetration, with the exception that I was allowed to fuck Mandy and Jenny raw but nobody else was, etc. And with that, I told Jenny and Mandy to get on their hands and knees on the bed, shoved my cock down Jenny’s throat, and told everyone that all of Jenny and Mandy’s available holes were free game. Cameron came over to Mandy and placed his cock in front of her, and she eagerly started sucking on it. Rick positioned himself behind Jenny, slid on a condom, and slid inside her. Jack took Mandy’s pussy and began pounding away. Tom unfortunately had whisky dick and was having trouble getting hard, so I offered him Jenny’s mouth to help him out. He accepted and Jenny began sucking him excitedly, trying to get him hard but also just enjoying being fucked and sucking a dick.
Nicky was standing against the wall watching all the festivities but not really doing anything, so I walked over to see if she was ok and make sure she wasnt uncomfortable. She saw me approaching and got on her knees and stuck out her tongue. I guess she was just waiting for a cock to be available.
Not needing to be told twice I presented my cock, which she took in her hand and began stroking and licking the tip. I kinda wanted to throat-fuck her but unlike the other girls, I didnt know if she was down with that. While she was blowing me, I asked her a few questions; was she ok with dirty talk, was she ok with being spanked, hair pulling, choking, rough sex, throatfucking, etc. She said yes to all but the throat fucking and choking. As she sucked my cock she started to rub her clit, so I told her “why dont you lay down and let me taste that dirty little cunt of yours.” she laid back on the unoccupied bed and srpead her legs. I teased kisses up and down the inside of her thighs before diving in and plunging my tongue into her pussy. soon she was bucking her hips and her hands were in my hair, grinding her pussy into my mouth. I started licking and sucking her clit and slid two fingers into her and started attacking her Gspot, making her scream and, a couple minutes later, squirt a bit. she squirmed and wriggled under the assault of my fingers, making her cum again and again.
I stood up and went to grab a condom as she lay there panting. I slid it on, spread her legs open wive, and slammed it in, putting her legs up on my shoulders and hammering down into her. I looked over to the other bed to see that Jenny was now getting DP’d by Jack and Rick while Tom face-fucked her, and Mandy was getting pounded into the mattress by Cameron as he choked her from behind.
I pounded Nicky harder, asking her “you like that, slut?” and giving her a light slap accross the face.
“yes i fucking love it daddy!” she grunted out between each thrust
“you like being a cheap little slut? you like being a fucktoy for a room full of guys like this?”
“Yes daddy I love being a fucking fuck toy!”
“you like it when I fuck you hard?” i said as I rammed it into her as hard as I could
“You like it when I make you take every fucking inch?” I ground into her, forcing my entire cock all the way into her cunt as deep as she could take it
“ahh its too fucking deep daddy! its too fucking big!”
I kept ramming it in deeper
“Oh is this cock too big for you? Am I hurting you slut?”
“Yes it so big daddy!” she put her hands on my chest and tried to push me back
“You fucking LIKE when I hurt you dont you bitch?” I grabbed her wrists and pinned them above her head as I continued to brutalize her balls deep, holding her in place and making her take it
“Say you like it when I hurt you!”
“Ahhhh! I like it when you fucking hurt me daddy!”
“Say youre a worthless fuck doll!”
“Im a worthless fuck doll daddy! You can fuck this toy whenever you want! You can use my dirty slut holes however you want!”
“Who do these holes belong to?!”
“Theyre yours daddy!”
“Say my name bitch!” I slapped her across the face
“john!”
“Say my fucking name!” I slapped her again
“John!”
I slapped her again.
“John! John! You fucking own this slut John! Ahhh fuck fuck fuck!”
I rammed it all the way into her once again as I felt myself tense up and cum in the condom inside her, feeling her spasm and clench down on me as she came all over my cock.
“thats a good fucking slut” I said as I leaned in and made out with her, my cock still inside.
After a minute I pulled out, took off and tied off the condom and disposed of it, and went to the bathroom to pee. When I came back, Cameron was still fucking Mandy, and Jenny had cum all over her face and was cleaning off Tom’s rapidly softening dick while Rick went down on her. Jack was standing over Nicky, stroking his cock back to hardness again. He knelt down and put his cock in her face, but I said
“Whoa man, ask first. Only Mandy and Jenny are free-use.”
“Oh shit sorry. uh… can I… is it ok if I put my cock in her mouth?”
“Ask HER dude. jesus.”
“Whatever you want John, its yours. my pussy is yours You can use me however you want daddy.” she said in a daze
“Well, thats a yes then. Use a condom if you fuck her.”
That was all he needed, and he shoved his now hard-again cock down her throat. I turned back to the others just in time to see Mandy spasming like crazy as Cameron came inside her in his condom. As soon as he pulled out, I stepped over and slid in, piinning her down and not giving her a moment to rest. Next to me, Jenny was getting fucked in the ass by Rick while Tom continued to use her mouth. A bit later TOm had Rick and jenny switch positions so she was riding Rick reverse cowgirl, so Tom could use her pussy while she rode Rick with her asshole. After a while I came inside Mandy. I looked over and saw Nicky was now riding Jack, so I went over and had her clean my cock off.
The night went on like this for another few hours. We took a couple of breaks to all rest and smoke some weed in between sessions, but all in all we went, on and off, until almost 6AM. All 3 girls got fucked at least once by each guy, I creampied both jenny and Mandy, and at one point after we had been resting Mandy started eating out Jenny and licking my cum out of her. This led to them 69ing, which got everyone horny again, which lead to me fucking Nicky’s ass and for a brief while her getting DPd by me and Cameron before she tapped out and said it was too much and safeworded. Towards the very end Allie, who had just been watching and, for the last hour or so, touching herself, decided she couldnt stand it anymore and wanted to get fucked, but she wanted to do it more privately, so she and Rick went into the bathroom and fucked for a short while. We all passed out around 6AM or so, with Nicky and Tom not even going back to their own rooms.
The next day when we all woke up most of us kinda wanted to fuck more after remembering the previous night, but we were all far too sore, exhausted, and hung over.
We all took it easy at the con that day, and didnt even really party that night. Just hung out and drank a *little* bit with a much more chill atmosphere. After the convention was over and everyone was back home, we started throwing around ideas of what to do at the *next* convention.
Source: reddit.com/r/gonewildstories/comments/hv2uy2/making_another_friend_with_benefits_fucking_her