Riley Gendreau
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The Kinky Dare: Cumming In The Club (August Exclusive)
🕑 Added 2025-08-04 17:24:44 +0000 UTCFirst monthly exclusive for August 2025
The Kinky Dare: Cumming In The Club
While some people enjoy normal sex, some people like to add spice and get kinky, and then there are those who love the world of kinks and are the kinkiest of all. I’m one of those people, and the kinkier something is, the more arousing and pleasurable it is for me.
There isn’t anything I can’t get off to or anything I won’t try. I even joined a website for kinky people where they give each other dares to do. I take on a new challenge at least once a week, and so far out of fifty-two challenges, I’ve only failed two of them.
So I’m on a bit of a losing streak, so what am I to do other than take a new dare and try to get back to winning? So my girlfriend sifted through the thousands of dares I’ve gotten last week and picked the one she thought was the best.
Like the last dare, she didn’t tell me what it was beforehand. Instead, she blindfolded me and brought me someplace, which told me that it was another public-type stunt, like back in the classroom.
Once we arrived, I continued to be blindfolded as we walked inside. I heard quite a few women whispering to each other as I walked by, which got my little man downstairs a bit excited, as I was starting to fantasize about what I was doing here that would involve them.
Not long after entering and being pulled around, my girlfriend stopped me and started to strip me down. Once that was done, she told me to open my mouth so she could feed me the pills. I laugh and ask her if it’s really another dare that involves me being a woman again.
She laughed with me, then told me that all the dares I got this week involved it, and it seemed people were going to keep requesting it. So my kinky adventures will be done in the female form for the foreseeable future, which is fine.
Once my body changed, giving me my wonderful curves, massive breasts, long hair, and completely feminine figure, my girlfriend told me that part of the dare involved a vibrating dildo being shoved in my vagina and asked me if it was okay for her to insert it.
I smile and tell her the day I don’t want a sex toy inside me is the day I’ll be dead. She didn’t say anything, but I suspect she was shaking her head, hopefully with a smile on her face. After that, I felt a very cold, very large lubed-up dildo push inside me and fill me up.
I couldn’t help but moan, and my girlfriend told me to save it for the show. I tell her I have plenty more of that in me and not to worry. The video would be a great one. She agreed with me on that, then started to put some clothes on me.
I asked her what she was putting on, as it didn’t feel like latex or the normal things I’d wear. She told me she started with a bikini top and bottom. Over the bottoms, I was getting fishnet leggings and then a tight black mini skirt.
Over the top, I was getting a mesh long-sleeved shirt, with a tank top over it, and then finally a denim jacket. To finish my outfit off, I was wearing a pair of ten-inch heels, which were nearly impossible to walk in, but my girlfriend said I wouldn’t be doing much walking.
She then checked me over and said I was ready for the dare. She then held my hand and walked me somewhere. I felt a curtain hit my side, and once we were on the other side, music started to play, and I heard a ton of guys cheering.
I found myself getting completely nervous; I’ve never done anything in front of a crowd before, but I loved kinky, and this already felt pretty kinky, so there was no way I was going to back down. I was going to beat this dare and end my losing streak.
After walking for a bit, my girlfriend stopped me, had me turn around, and pushed me up against some sort of metal pole. She then took my hands and lifted them up, tying them to the metal pole above my head. She then did the same with my feet.
With that done, she told me the dare was about to start. She then finally explained what was going on. We were at a strip club, and I was currently tied to a stripper pole. My dare was to free myself before I’m stripped nude.
The fun part is every time I cum, I lose something I’m wearing. The first thing will be my blindfold, and then my clothes will come after that, but the real kicker to this challenge comes from the dildo inside me.
It’s a special one that this club uses, which allows the audience to tip the person wearing it. If I get a tip, the dildo will vibrate or thrust. So if I get enough tips, it’ll go long enough to make me cum, which means I’ll lose a piece of clothing.
My girlfriend told me to figure out how to get free quickly, as there were a ton of guys ready to tip me already. She then wished me luck and said she’d be back to remove the pieces of my outfit when I cum.
With that, the dare officially started, and the audience was able to tip me. Right away the tips came floating in, and the dildo was vibrating like crazy. I was thrashing around and moaning like crazy, and the pleasure was enough to get lost in, but I couldn’t do that.
I had to gather all my willpower and focus. I had to break these ropes, and the best way to do that was to move them up and down the pole until friction burned through them. That may have been my first mistake.
Turns out, me doing that made it seem like I was rubbing up against the pole begging for more, so the amount of tips that came in doubled, and the dildo started vibrating and thrusting. My moans got louder, though I’m not sure anyone but those in the front row could hear them.
I was unable to hold off my first orgasm, and I felt myself filling my bikini bottoms with cum, followed by it leaking down my leg. The music stopped suddenly, and an announcer let everyone know that I had orgasmed, which meant it was time for me to strip.
I gulped and felt my face starting to burn. It was beyond humiliating having people watch me orgasm live like this. I wanted to die of embarrassment, but my damn kinky self was loving it, and before my girlfriend made it to me in order to remove my blindfold, I came again.
Again the announcer told everyone, and I heard my girlfriend laughing quietly as she approached me. She asked me if I was having fun, which I couldn’t deny as my cum dripped off my legs and onto the floor below me.
She removed my blindfold, giving me my first look at the club, the people inside, and the situation I found myself in, which only added to my humiliation, which works against me. After I adjusted to the light, my girlfriend asked me what she should take off first.
I looked down and picked the jacket I was wearing. She nodded and ripped it right off of me, which got the crowd going wild, and along with it, my dildo. I once again drew upon any willpower I could in order to focus and resist an orgasm while I continued working on the ropes by my legs.
I managed to free one of my legs before anything else happened, but as soon as I got one part of myself free, someone gave a big tip, which set the dildo to max for three minutes straight. It was too much to ignore, and I found myself bouncing up and down as it thrust inside me.
Not long after that, the pleasure of an orgasm flowed throughout my body, and globs of cum flowed down my legs. One announcement and losing my mesh t-shirt later, I was back at it and trying to get my other leg free.
My thought process was that if I had my legs free, I could get more leverage for working on the ropes around my wrists, which were much thicker. Some more time bouncing around and rubbing my ass against the pole, my other leg was free.
I was feeling pretty confident at this point, as I still had six things to lose before I failed the challenge, so I should have had no problem. That confidence didn’t last, as happy hour started, which meant all tips were worth three times as much.
So they could pay the same amount but fuck me much more, which is what happened. The dildo started vibrating and thrusting on max nonstop. I fell to my knees and started moaning and bouncing up and down along with the thrusts.
I quickly lost my skirt, fishnets, and bikini top and bottom, leaving me in just the pasties and heels. I was still on my knees, and my legs were covered in cum, and when I wasn’t moaning, I was trying to catch my breath.
At that time I pretty much gave up on the challenge, thinking I had no chance. I was exhausted from the pleasure, and I hadn’t been working on breaking the ropes, at least I thought. It turned out that while I was bouncing, I continued to burn through them.
I heard a snap and looked to my side to see a rope falling down. A big smile appeared on my face, and I started to cheer. I was so happy and excited that I let myself cum again just to reward myself for winning.
I enjoyed every bit of it, even as a couple dozen men watched me squirt out the side of my dildo. I was enjoying the feeling of pleasure when suddenly the announcer said I was apparently giving up and giving in to the pleasure.
I look towards him and wonder what he meant. I then tried to move my hands to show him I had gotten free, but that’s when I realized they were still stuck. I looked up and saw that there was another set of ropes holding my wrists to the pole.
They had been hidden underneath, and I didn’t even realize. I let out an awkward gulp as my girlfriend approached me again with a big smile on her face. She pulls the heels off my feet and tells me what I already knew. I was out of clothes, which meant I failed to escape, and I lost the dare.
She tells me to have fun, and that once I finally manage to free myself, we can go home. She leaves, and my dildo starts vibrating again. I can’t believe I lost another dare… I mean, this was sort of amazing, but still… I need to win one! So next week, no matter what, I’ll win!
Comments
Riley
It's someone's favorite on deviantart. They actually asked me to make more, which is mostly why this one came up. I do think I'll just keep making them intense, kinky situations, as it's been a lot of fun. As for out mc, he did pretty well, winning fifty times in a row, but winning streaks always end, but in this case, I'd say that most of them were tamer, and not many involved turning into a woman, so that seems to be what gets him, and by that I mean he enjoys being a kinky woman too much.
last_of_workers
Well, I can judge now that the series "The Kinky Dare" will be a long-standing fixture among your regular stories and I must say I'm all for it! Watching very difficult and extremely perverted tests is an incomparable pleasure! So I will hope that this series of stories will stay with us for a long time and best of all forever and I also hope that the professional skills of our main character will wake up again and he will start winning at least occasionally... Just looking at his 3 losses in a row I don't believe that he won 50 times before... This makes him seem not a professional but a braggart... In general, the story is very good and I really liked it so I'm looking forward to the continuation!
