Riley Gendreau
patreon
The Kinky Dare: Cumming In The Backdoor (Exclusive May 2025)
🕑 Added 2025-05-29 21:55:51 +0000 UTCWhile 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-one challenges, I’ve completed all but one.
That brings me to today, which got me a new dare. After my last dare failed and the videos and pictures circulated, I got quite popular on the kinky website I used to get dares from, and with it the dares got even kinkier.
Seeing as it was the next week. It was time for a new dare. My girlfriend sifts through them looking for something fun and finds one that makes her laugh. I asked her about it, and she told me not to worry; all I needed to do was wait in the bedroom while she set it up.
I nod as I trust her completely and go to the bed. It took a couple of hours, but she came back with a bag of things. She started by handing me another gender-changing pill. I laughed and made a joke about people really liking my feminine form, which she laughed at and said she understood why.
I take the pill and start removing my clothes, as they soon wouldn’t fit. My girlfriend sets the cameras up while my body begins to change. Like before, I was turning into a woman, so I got shorter and thinner, large breasts grew on my chest, and my cock and balls were replaced.
I felt myself get aroused as I looked down at my massive breasts. I mean, I am a guy, but being a guy doesn’t mean you can’t enjoy the pleasures of big breasts when you have them, right? I mean it’s all for fun, and I plan to have a lot of fun.
Once my girlfriend sets up all the cameras, she comes back over and hands me the outfit I’ll be wearing, and I was happily surprised to see it’s some very tight, very revealing latex. It was split into five parts: two thigh-high socks, two sleeves, and a top.
A top that didn’t cover an inch of my breasts, which was perfect. These big melons of mine would be free and erect during this dare. After getting everything on, my girlfriend comes over with the gear I’ll be using this time.
It was a ball gag and a bit of rope. The gag was put into my mouth, and the ropes were used to bind my arms behind my back. With that done, my girlfriend told me I was ready and began to tell me about the dare.
There were a lot of them that wanted to see me lose my female virginity. A lot of people want to see me get fucked by a man, but she said she thought that might be a bit much for me for now, so she found one that's a stepping stone.
So today, while a female is bound in rope and latex, I’ll be having my ass fucked. The dare itself was to make a man cum using my ass while wearing latex and bound up, and without orgasming from the whole thing.
I gulp; it sounds amazing but hard. She then clapped her hands and told me it was time to get started. She turned on all the cameras and left me waiting by our bed, and a moment later a large man with no clothes came walking in.
He was tall, buff, and handsome, but most importantly, his cock was at least eight inches long, and it was soon to be in my ass. He comes over to me and smiles. He caresses my hair before touching my breasts for a bit.
He called me quite beautiful and said he was happy to satisfy me. He then picked me up and put both of us on the bed. He then helped me get into position above his cock. I found myself in a bit of an awkward spot.
I was crouching right above his crotch, and the tip of his cock was touching my left ass cheek. We both stopped for a second while he reached over and grabbed the lube my girlfriend had left. He takes a bit and coats his cock.
He then takes the bottle and pushes it into my asshole. He gives it a bit of a squeeze, and I feel the lube start to fill me up. I made a bit of noise from the pleasure as that happened and found myself excited to have his cock in my ass.
Once he removed the bottle, and the lube started to leak out my ass, he took his cock and held it in place and told me I was good to lower myself. I did so and began to moan as his large cock opened up my ass and pushed as far inside it as possible.
Once It was most of the way in; the man held my stomach. He was holding me up since my arms were bound and I couldn’t do so myself. This also let him pick the speed we went, as I was relying on him to help me up and down.
At first he went slow, which was to spread the lube around a little more; it also gave the guy time to get fully hard, which made him even larger. With both of us seemingly prepped, the real fun started. He started lifting me like I was a small weight.
Up and down I went, my ass bobbing up and down with his cock sliding in and out of my ass, and my breasts resting on the guy's face, thrashing around and sometimes poking him with my very erect nipples.
It was amazing, too amazing, and without thinking about it, I nearly orgasmed. When I felt it come, I quickly clenched my whole body, which included my ass. So I tightly held the guy's cock, which made him moan.
That made me laugh, as I knew I could use that to win. So from that moment forward I kept myself as tight as I could and started to ride his cock with as much force as I could muster. The guy clearly loved this as he continued to moan.
I tried to use this to my advantage and make him cum and continued to clench as I rode his cock, but I didn’t realize how much strain that put on my muscles, and after some time exhausting myself bouncing up and down, I got a cramp and stopped.
That split second was all my pending orgasm needed in order to complete. I crouched over the man, with half his cock in my ass, my hands behind my back, and my head pointed up as I gasped for air and squirted all over the man's lower stomach and upper crotch.
Once I was done, I felt my face heat up from the shame and embarrassment. I’m not even sure why, maybe from losing another challenge, from being a woman who just got fucked, or from the fact that I was really liking these new dares. Perhaps I find losing kinky as well.
Either way, with drool coming out of my mouth and cum dripping from my vagina, I slowly turned my head towards the camera pointed right at my ass and showed off my shameful look. Might as well show the viewers I know I’ve been defeated.
As I stared at the camera, the man decided that was a good time to reward me for my hard work, and he began to unload himself in my ass. It felt a lot like when he had the lube bottle in there; glob after glob of liquid entered inside me.
This time though, it was much thicker and warm instead of cool. Once he finished, he removed his face from my breasts and thanked me for a wonderful time. He then lifted me up and slipped out from under me before dropping me tits first on the bed.
He then left the bedroom, and I looked towards the door, waiting for my girlfriend to come back in and let me out, but she didn’t seem to come right away. So I just sat there humiliated and leaking that man's cum out of my ass but loving every second of it.
Yet another failed challenge, but that’s okay; it was great, although I’m sure once my girlfriend posts this one, I’ll get a ton of new dares, which I can only assume involve me turning into a busty woman as well—at least I really hope so.
Comments
last_of_workers
you know, reading the last story, I decided that it was a single story... as it turned out, I was wrong and now I'm very happy about it because the sequel is in no way inferior to the previous part and in some ways even surpasses it. Overall, I really liked this story.
