Riley Gendreau
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The Kinky Dare: Cumming in The Classroom (Exclusive April 2025)
🕑 Added 2025-04-18 21:32:04 +0000 UTC(Characters are consenting adults.)
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 a new challenge at least once a week, and so far out of fifty challenges, I’ve completed each one.
That brings me to today, which got me a new dare, which might be the kinkiest thing I’ve ever done. The dare I was given was to go to my college, take a bunch of gender change pills, strip nude, insert a vibrator into my ass and vagina and tie myself to the chair using rope.
So not only was it public nudity, rope bondage, double penetration, humiliation, and multiple orgasms, but I also got to add a bit of gender change to the mix, which I’ve only done once when I was dared to wear a tight latex suit and ride a mechanical bull with a large dildo in place of a saddle.
Back to the current dare. I have to do all of that and then cum ten times. Once I’ve done that, I then have to get myself free by untying all the knots in the ropes. I also have to do this all within an hour, as after that other people start arriving at the college.
I could be in some big trouble if I get caught, but it was worth it for the thrill and the pleasure these dares give me, plus I’m pretty good so I have nothing to worry about, especially with my girlfriend, who’ll be helping me.
She wasn’t super into my level of kinky at first, but she made me a deal: when I do kinky things, she gets to film it and post it online to make money, which she does share with me. So honestly, it was a win-win to accept.
I take her and we head to a classroom that’s barely used and we get to work. I remove my clothes while she sets up a few cameras and gets the pills ready. She tossed me the bottle and I took a few and began to change.
In minutes I go from an Avenger guy to a pretty woman with a slim waist and small breasts. My girlfriend looks at me and suggests I take a few more pills to increase my bust, as it would make the video much more appealing for the fans and, of course, be more pleasurable for me.
I nod and take five more, and after I do so, I watch my breasts like balloons until I have two massive breasts trying to pull me down. I pose sexy and ask if this is good enough. My girlfriend looks at me and smiles, then tells me I was indeed sexy.
She then takes my hands and ties part of the rope around one of my wrists. She then uses it to pull me over towards a chair. She pushes me into the chair and asks me if I’m ready to do this and if I’m sure I want to do it.
I tell her I’m more than ready and tell her to do her worst. She nods and begins really tying me up. She tied my wrists together, then moved up to my upper arms and wrapped the rope around them several times before tying the ends together.
She then went around my breasts, above and below them a few times, before coming up between my cleavage, around my head, and back down my cleavage. Then for the last bit of that section, she tied the end of that rope to my wrists so I couldn’t get off the chair.
After that she tied my lower thighs and ankles together. Now there was only one more step before my challenge started. My girlfriend went into her purse and pulled out a pair of very large vibrators. I was a bit nervous about the size, but she assured me it would be alright.
I then watched her lube them up, then lean over and squirt the lube onto my butthole and vagina. It was cold, which didn’t feel great, but when she used her finger to rub it in, that all changed, and I knew that once they were inside me, this would be amazing.
I lifted my butt up first and let her shove the first one in there. I’ve done anal a ton and have had large things like this in there before, so I was more than used to the stretching feeling and intenseness of being filled up, and yes, I love it.
Next up was my vagina. This was something I don’t have much experience with. This would only be the third time I’ve done something as a woman, and only once did it involve something inside me, and it wasn’t nearly as big.
As my girlfriend pushed it into me, I realized it felt similar to when the one went into my ass, with the only real big difference being how much more sensitive my vagina was. It was nearly as sensitive, and thus having this shoved inside me was ten times more pleasurable.
Once it was fully inside me, my girlfriend let me catch my breath before she started the cameras. Once the cameras were on, she told me to have fun. She then clicked a button on a remote, and I felt both vibrators turn on.
Instantly I felt my entire body heat up and I started gasping, which soon turned into moans that I was trying really hard to keep quiet, but that was a fruitless effort. It felt too good, and I was really enjoying it, which was good.
I managed to cum for the first time in less than two minutes. I felt my cum flow around the vibrator and squirt out of me and down my legs onto my chair. I felt the bliss of an orgasm wash over my body, and before it even started to fade, I could feel I was close to my next one.
As each orgasm came and went, I began to moan more and more and struggle more and more against my restraints and the chair I was bound to, and at one point the puddle of cum I made nearly made me slip right off the seat and fall to the floor, but I managed to catch myself.
After about a half hour of nonstop pleasure, I managed to cum ten times, which meant it was time for me to start untying the knots to release myself from the rope. I struggle to focus for a bit, but eventually I get my hands around the knot holding me to the chair.
I begin to fiddle with it. It takes me a few more minutes but I get it undone and manage to move my arms from behind the back of the seat. I was about to start trying to untie my wrists, but my next orgasm came.
Number eleven caused everything to start going wrong. Not only was it more powerful than all of the others so far, but I shot so much cum out and onto my seat, which once again caused me to start to slip, and unlike last time, I wasn't tied to the chair to help me catch myself.
So I slipped downward, spreading my puddle of cum all over my back as I went down to the floor. I was now lying on my back, which made it really hard to get my wrists untied, and to make it worse, my cum was now dripping off of the chair into my face.
I knew I had to roll over, but I also knew it wouldn’t be easy with how slippery I was now thanks to all the cum paired with how I was tied up. I tried several times but didn’t get it. I needed something to give me that extra oomph.
I look at my large breasts. That was the answer. I had to use them and their weight. Having come up with that idea, I began shaking my breasts back and forth, and with each swing I turned more and more, and after a couple dozen, I managed to flip onto my stomach.
I didn’t really think that through that much, as I landed on my breasts and started crushing them, which was such an intense feeling it caused me to cum yet again. After coming down from the orgasm high, I focused again on the knots.
I only had about ten minutes left to get free, and it was hard enough as it was, but now that the ropes were covered in cum and hard to grasp, it was nearly impossible. I fumbled around trying to just hold the knot in my hands, and it only got worse when I tried to pull them apart.
It only felt as though the knots got tighter. The college bell went off and I looked up at the door and felt my heart drop. I was out of time; I needed to get free and get out of here in the next few minutes or someone would surely discover me.
I muster all my strength and manage to sit myself up. I then proceed to have yet another orgasm before scooting backwards and using the end of the chair to saw the rope. Luckily the rope was pretty cheap, so I started getting through the layers.
The only problem was how my girlfriend tied them; I had to break the right layer in order to get them all to fall. I managed to get through three layers when they finally fell off and released my arms a bit. I quickly went on to untying my thighs.
Right as I got the ropes off of them, the door opened, and I looked up to see some random guy looking at me. He didn’t say anything and looked confused for a moment, but then smiled when he realized what was going on.
I panicked a bit and went to untie my legs, but I wasn’t fast enough and he called his friends. So I quickly had a group of horny guys watching me struggle to untie myself. Then the most embarrassing thing happened: I came again, right in front of all of them.
They start cheering, laughing, and pulling out their phones. I’m then overcome with shame and embarrassment, but it felt so good. The humiliation nearly made me cum again. After several minutes with all these guys watching, I managed to get myself free.
I grabbed my clothes and the cameras and ran out of the classroom. I met up with my girlfriend in the bathroom, who helped me clean off and change back into a guy. I then gave her the cameras and we walked out of the bathroom to find the whole school amused about something.
I already knew what it was, and my girlfriend was just finding out as her friends shared the videos and pictures those guys took of me. She looked at me and laughed. She then said it seems I completed the dare, just not in time.
She then slapped me on the butt and said she wished me better luck next time. I let out an embarrassed laugh. After that mess I really shouldn’t do any more, but honestly it was so much fun and by next week, I know I’ll be accepting a new dare.
Comments
Riley
I once felt that way myself. I think as long as you like what you like, and it doesn't hurt you or anyone else, there's nothing to be ashamed of. Also, most kinky people are slightly perverted, but we're perverted in the best way.
last_of_workers
Yes... I thought that I was a normal person and I couldn't be called a pervert, but reading this story I discovered that I wouldn't mind being in this character's place... how am I supposed to live with the realization of this fact?
