Riley Gendreau
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The Kinky Dare: Cumming For The Fans Pt1-2 (October Exclusive)
🕑 Added 2025-10-27 22:58:31 +0000 UTCFifth and sixth exclusive for october 2025
The Kinky Dare: Cumming For The Fans I
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-three challenges, I’ve only failed the last three of them.
So I’ve been on one hell of a losing streak, but I won’t let that get me down. I’m determined to win the next one. Like before, my girlfriend picked this week's dare, then started preparing it while I waited in our bedroom.
It surprisingly didn’t take very long before she came in and said it was all set up. She then had me take the pill that turns me into the big-breasted, horny bimbo I’ve gotten quite used to being. I did make a joke about every dare lately involving me being a woman.
My girlfriend looked up at me and just smiled at me. So I assume she’s picking them on purpose, which I don’t mind; these dares are a hundred times better as a woman. Maybe that’s why it’s been harder to win, but I can’t wimp out and only pick easy challenges now, can I?
Once I changed, my girlfriend surprisingly had me wear normal women’s clothes, which was quite different, but I didn’t question it. Instead, I just kept following her and waiting to find out what I was doing today.
We got in her car, and then we took a short trip through town. It seemed we were doing something in public again, like last week's dare, but I found it quite interesting that she had me turn into a woman before we got there. I wonder why she did that.
After driving for about ten minutes, we arrived at a large warehouse, which I recognized. It was often used for events, things like concerts, parties, really anything that could have large crowds. We get out of the car and my girlfriend leads me to a hidden back entrance.
That led to the backstage area, which had tons of kinky stuff sprawled across it. My girlfriend told me to stand around and wait for her to check on things, so I walked around checking out the stuff here. There was a large cage and a small one.
Next to that was a wooden horse and a pillory. There were nearly a hundred dildos, all different lengths and thicknesses. The sight of them nearly had me drooling. I still have no idea what we were doing, but I hoped it involved at least a few of them.
There were a ton of other toys and furniture and I would have looked at them all had the curtains for the stage not suddenly opened up behind me. I turned around to look out, only to have some spotlights shine on me.
I was blinded for a moment, and before I could open my eyes, I heard cheers from a lot of people. When my vision came back, I saw where they were coming from. There was a massive crowd looking up at me.
I raise an eyebrow and look around, wondering what was going on and why they were here. As I stood there confused, someone put their hand on my shoulder. I turn my head to see my girlfriend, clad in a very tight latex suit, with very high heels, holding a riding crop.
She smiles at me and tells me to blow a kiss out to my loving fans. I looked at her confused, then at the crowd. I could feel my face burning as I realized they were the ones submitting dares and watching my videos.
I let out an awkward laugh and asked my girlfriend what we were doing for the dare this week. She said I’d soon find out; she then used a riding crop to whip the back of my leg, making me fall onto my knees. The crowd loved that and started cheering again.
My girlfriend walked in front of me and told me to remove my clothes. My face burns even more as I think about undressing in front of all these people, but seeing as I’ve done this before and they’ve all seen me naked before, it really shouldn’t be this embarrassing.
I remove all my clothes and then get back on my knees, going with whatever we were doing here and waiting obediently. My girlfriend addresses the crowds and thanks them all for coming here and joining me for this week's dare.
She tells them it’s time for the main event to begin. She claps her hands and the monitors on the walls around us all turn on. Then I watch as everyone in the crowd pulls out their phones and starts doing something.
Suddenly the screens had pictures of the kinky items behind me on them, and next to the image was a number, some of which were increasing quite quickly. After a minute the pillory seemed to have the most votes.
My girlfriend clapped again and said the crowd had spoken. She clapped her hands again and a pair of women wearing full-body latex suits came out and wheeled the pillory out to the center of the stage. After that my girlfriend whipped my back with her crop and told me to get in it.
I nod, stand up and stick my arms and head through; moments later it’s closed and I’m locked in place. My girlfriend addresses the crowd again and tells them it’s time to tell me what the dare is this week.
She then looks at me. She tells me that this week's dare is to let her fans pick objects to pleasure her with, and for every time I cum, I have to spend one day as a woman, and for every ten times I cum, one lucky fan gets a very special night with me.
If I cum fifty times, then I officially lose the challenge, and if I lose, my girlfriend told me that she was going to leave me bound and give every single fan here a chance to play around with me. She then whispered in my ear and told me there were nearly three hundred of them.
I gulp and look out at them. This was going to be tough, but I had a bit of leeway. I can cum forty-nine times and still win… I mean, that would also mean I’ll be stuck as a woman for forty-nine days and have to spend a night with four fans, but at least I’d win.
I think my girlfriend realized what I was thinking, and she took her crop and slammed it down on my large ass, making me cum instantly. She then laughed and said this was going to be much harder than I thought.
I looked down a bit ashamed as my cum shot out towards the floor and all over my legs. I hadn’t even realized I was so aroused; I guess I’m so used to being on the edge lately that it’s sort of normal. So she was right; I was going to need to hold it in as best as I could.
My girlfriend turns toward the crowd again and tells them it’s time to pick another item. They all pull out their phones and start voting, all while my girlfriend walks around me hitting me with her crop every few seconds.
She stops when the voting ends. I look up at one of the screens to see what won the vote. The image looked like some sort of machine with a rod, which I’ve never seen before, but it was bound to be quite kinky.
My girlfriend clapped her hands and told her assistants to bring out the fucking machine. I raised my eyebrow and tried to look behind me, but thanks to the pillory, I couldn’t move, never mind see anything behind me.
My girlfriend walks away and comes back a moment later. She stands in front of me and shows something to the crowd. She asked them if they thought it was a good choice and they started cheering.
She then turned and showed me what she had. It was a twelve-inch-long, three-inch-thick dildo shaped like a tentacle. I let out an awkward laugh as she walked behind me with it. After a few moments, I feel the thing push into my ass.
I let out a loud moan as I’m split open and filled up, which could barely be heard thanks to the crowd cheering so loudly. Once the dildo is in all the way, I start trying to catch my breath. As I did, I noticed the screens were now showing off my ass.
I could see the base of the dildo poking out of my ass, as well as the metal rod it was attached to. As I stared up at it, my girlfriend hit a switch, and the machine suddenly started thrusting in and out of my ass. I began moaning again, and I knew I was already close to orgasming… this was going to be a tough one… I wonder how long we’re doing this for.
The Kinky Dare: Cumming For The Fans II
It’s been about two and a half hours since my girlfriend brought me to this place, stripped me naked and started this week’s dare, which also involved putting on a live show for my many, many fans that I apparently have.
The dare was sort of simple. I had to let the crowd decide what to do to me in order to make me cum, and for every day I cum, I have to stay a woman, and for every ten times I cum, one fan gets to have a special night with me.
Lastly, if I cum fifty times, all of my holes will be open to every horny man in the building, which is somewhere around three hundred. When we started, I had hope that I’d be able to win this challenge.
Now, however, after starting with being locked in a pillory and fucked by a fucking machine with a tentacle-shaped attachment, I wasn’t so sure. They used that on me for the first half hour, which made me cum fourteen times.
So at that point I was up to fifteen, which wasn’t a great start, but I still had plenty to go before I lost. The fucking machine was pretty intense, so I made the foolish assumption that it would be the most pleasurable thing.
However, after we were done with it, the voting began again and the next situation I found myself in was just as intense. I was placed on that wooden horse I saw before, with an inflated butt plug in my ass, a ball gag in my mouth and nipple clamps that pulled on my nipples.
My girlfriend then picked two random people from the crowd to come up on stage. She then gave each of them a long feather and told them to tickle me to their heart’s content. They were more than happy to do so.
I found myself trying to laugh through my ball gag, all while squirming around from being tickled. The squirming then led to me pressing the peak of the wooden horse into my vagina and moving the inflated butt plug around, which was incredibly pleasurable.
I managed to hold out during that segment and they only made me cum eight times. I was so tired after that and I felt like my body couldn’t possibly cum anymore, but the next segment proved to me how horny and desperate my body is.
I was put into a latex suit like my girlfriend’s, but with some bonus things added. I was put into a pair of very high horse hoof heels, had a pair of horse hoof gloves strapped to my hands, had a saddle strapped to my back and finally had reins put into my mouth.
My girlfriend had her assistants dressed the same way, but they got one more thing that I didn’t. They had strap-ons attached to them, and they were quite large. I knew right away why they had them. They were for fucking me.
Luckily this segment was a bit of a game; they had to chase me around, and only when one of them caught me were they allowed to fuck me for two minutes. We all had the same heels on, so we were stumbling around and falling quite a bit, which helped me, but there were two of them.
So they caught me a few times, and when they did, they mounted me from behind and picked one of my holes to shove their strap-ons into. There were even a few times where they both caught me at the same time, which meant they used both my ass and vagina at the same time.
As the segment went on, the assistants got more of an advantage over me. As I came over and over, my cum dripped down my legs and eventually to my heels, which made me slip and fall more often.
That segment lasted a whole hour, and I got caught and cucked by the sexy pony women a total of twenty times, and of those twenty times, I only came eleven times. That brings us up to the latest segment, the one I just finished.
My girlfriend told them that this would be the last one, and that meant they had to vote for something really good; as if they wanted to have the meet and greet afterward, they needed to make me cum sixteen more times.
After that the voting began, and I honestly couldn’t even picture what they’d come up with, as everything up until that point was already pretty kinky, but my fans are as kinky as I am and came up with something.
They had voted to have me tied up from head to toe, blindfolded with earmuffs on so I couldn’t see or hear, and lastly, they voted to have a magic wand set to max strapped to my vagina. For the next half hour I sat there squirming in the dark, unable to see or hear anything.
It was just pleasure, nonstop pleasure. It was the perfect thing to get me to fail. Without being able to hear or see anything, I couldn’t focus my mind on something else. The only thing my mind could focus on was the amazing feeling spreading throughout my body every time I came.
After my sixth orgasm, I started to panic a bit. I was only ten away from losing, with no idea how much longer this final segment was going to go on for. So I began thrashing around trying to dislodge the magic wand.
It was secured very tightly to me, as if my girlfriend expected me to try this, so the only thing I managed to do was get the top of the magic wand to pull up and then slam back down against my vagina, which hurt, but my damn kinky body and mind loved the pain.
So that only added to my pleasure. I came two more times before stopping to try and think of something else. I decided to try and flip myself over, thinking I could press the wand against the floor and my vagina to force it to stop working.
However, when I did so, I landed on my breasts and the weight of my body pressed them quite hard into the floor, which I should have known would be pleasurable. I came again, which made me quickly give up on this plan and start trying to flip back over.
I was moaning and drooling all over myself at that point, and I could feel my cum puddling up on the floor below me. I gave up trying to flip over for a moment in order to try and regain some of my strength to flip myself over.
As I sat there switching between moaning and catching my breath, my thoughts started to race. I’ve orgasmed over forty times so far, which means no matter what, I’m going to be spending time with four of my fans.
It also means I’ll be in this very sexy, very horny body for over a month. The thought should make me embarrassed or maybe ashamed, but it just aroused me further. I started to picture all the kinky things I could do; I even found myself wondering if I should do dares daily during that time.
Those thoughts didn’t help me one bit, as just thinking them led me to orgasm again. I tried to think of other things, but that didn’t work, so I went back to my previous plan of rolling back over. I swayed back and forth in order to gain more power.
Once I felt I had enough, I went full force and started rolling, which turned out to be a mistake. I rolled myself to the edge of the stage and nearly fell off. It would have hurt a ton if I fell, but more importantly, I’d probably have come from it.
Fortunately, I didn’t roll off; unfortunately, I rolled close enough to the edge for my fans in the front row to reach me, and I suddenly found myself being touched and grop ed in various places. One of them even tried to slip their finger inside of me.
I think my girlfriend stopped them, though, as I suddenly felt her crop hit me right on the vagina, which made me orgasm again. I assume she told them they could touch me on the outside, but they’re not allowed to slip anything in me.
The grop ing, vibrating and orgasms all continued for what felt like forever, and when the magic wand finally stopped, I was beyond exhausted. I sat there motionless, trying to catch my breath and trying to convince myself not to pass out and sleep for the next week.
As I lay there, my girlfriend's assistant came over and picked me up. They dragged me over to a chair and sat me down. They then removed the magic wand that was strapped to my leg, then the ropes, and finally they removed the earmuffs and blindfold.
It took my eyes a minute to adjust, but when my vision came back, I saw the screens around the warehouse all had the word "congratulations" with my name next to it. They all then changed and flashed the number forty-nine.
I felt a smile appear on my face and I looked over at my girlfriend, who's wearing normal clothes again. I ask her if that means what I think it does and she nods, saying it did, and that completed this dare.
I jumped up and raised my hands into the air to celebrate, which caused my breasts to bounce up and down and my cum to splatter all over the place. The crowd cheers alongside me as I celebrate my first win in a while.
Out of fifty-four challenges, I’m now at fifty-one wins and three losses. I lower my arms and blow a kiss to the crowd and thank them all for being here and being such loyal fans of mine. I encourage them to continue sending me their kinkiest dares.
After I finish speaking to them, my girlfriend starts speaking to them and telling them it was time for the random drawing to see which four lucky guys got to spend the night with me and give me a dare to complete.
Today was a kinky marathon, which was a nice change of pace, but now it’s back to the normal routine, and this time, my kinkiest, horniest fans will get to choose what dare I’m doing. I wonder how that’ll go.
Comments
Riley
I'll be honest, this one was a bit different. That "Win" might just be a trick. After all, she still has to be a woman for what was it, forty-nine days? And she has to take a dare from four lucky fans. So perhaps that "win" was just to distract our hero. C;
last_of_workers
Well, here we are, a sequel to "The Kinky Dare," and for the first time, we witnessed our hero's victory! Although I think the rules of this particular game were a bit unbalanced... I just can't shake the thought that cumming less than 50 times a night is too easy a victory condition... that's the only downside I see, otherwise the story is simply amazing!
