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[EROTICA] Cheating: Part One

“Now, are you going to be a good boy and listen to Me... or am I going to send THIS video to the school disciplinary board?”

“Alright what do you want?”

“Be outside My room at 8pm sharp tonight”.

“But...I had plans to join the guys for a couple of drinks to celebrate the end of our exams.”

“I’m not stopping you from joining them, just know that if you’re not outside My room at 8pm tonight, that video is going to end up with the school disciplinary board.”

“Ugh, fine.”

“See you tonight, My dear boy”.

Just then, Caittrin’s shuttle bus arrives. I was still taken aback by what had just transcended over the past 5 minutes. I was alone waiting for my shuttle bus back to my dormitory and out of the blue, my Resident Assistant (RA) Caittrin came up to me and sat beside me. The only time we really bonded was during our Residence Orientation camp but once the camp was over we became hi-bye friends. Admittedly I would steal glances of her every now and then when the opportunity arose, she was a short, petite looking girl with a really sweet captivating smile. If you weren’t mesmerized by her looks, her toned, athletic body would definitely get your heart pumping and boy did she just manage to get my heart rate up but not in the way I had ever hoped for, blackmailing me for cheating during my online programming methodology exam. It still baffles me how she managed to record me cheating without my knowledge. I knew I should have locked my door before starting on my exam.

I didn’t know what to do, but what I knew I couldn’t afford was to let that video end up with the school disciplinary board. Not only would I end up failing this module but I would also definitely end up losing my scholarship for it. I thought to myself, maybe I could just take out a few hundred bucks and give it to her so that she’d stay hush on this matter. I wasn’t very well off, but heck if it came down to that I would be willing to part with that few hundreds of bucks just to close this matter.

It was only a few hours since I last saw Caittrin at the bus stop. I was in my room, anxious of what was to come. Most of the students staying on campus went out to celebrate the end of exams, either that or they had already packed up and left campus to return to their homes. I too should’ve been out celebrating if not for the fact that I just got blackmailed by my RA. It was 755pm, I was getting ready to leave my room and head downstairs to find Caittrin when suddenly I received a message:

“Change into your suit. And put on your blazer as well.”

“Who the fuck wears a suit on campus like this? That’s so embarrassing.”

“Do you think you’re in a position to argue? Also, don’t be late.”

“Wtf this is ridiculous. How can I change into a suit and still meet you in 5 minutes?”


She didn’t reply any further. It was so frustrating because she and I both knew that I was at her mercy. I still couldn’t comprehend why she insisted on me wearing a suit and blazer on campus like this, but I figured it doesn’t matter. It was just one night of making her happy and it would be all over.

It was 8:05pm, I was finally at her doorstep. It was embarrassing being so overly-dressed on campus like this on a Friday night. I stood outside her door, anxiety overwhelming me as I hoped that nobody would walk past and see me in my state. No response, did she fall asleep? I knocked on the door a few more times but still no response. I dropped her a message stating that I was outside her door and no reply either.

A few minutes had passed and there were starting to be a couple of girls walking by the common area to wherever, not that I cared. The only thing that bothered me was that they were giving me weird stares like I was some weird pervert considering the fact that this was an all girls’ floor. Where the fuck was Caittrin? Was she toying with me? Just as things could not get more embarrassing for me, the door opens.

“Come on in, hope you enjoyed the stares you were receiving while waiting outside.”

“WTF! Did you intentionally leave me outside your door like this and ignore my messages?”

“Duh... As long as I have this video, which by the way has been replicated across multiple cloud storage accounts, You’re under My control...”

Just then, Caittrin grabs me by my necktie and pulls me closer to her, for the first time since I met her I was so close to her. She had this feminine lavender vanilla smell that was so addictive I couldn’t stop taking whiffs and sniffs of it.

“You see little boy, if you don’t do as I say, or if I’m not happy with your attitude, you know where this video is going to end up. So you better be a good boy... and for starters, get on the bed and close your eyes. Spread your arms and legs and do not, I repeat, DO NOT open your eyes until I tell you to do so..”

I thought to myself, well I was in no position to argue and I figured, maybe if I just listened everything would be over by the end of the night and this episode would be over and I could finally move on with my life.

So I did, crawling onto the bed, spreading my arms and legs as instructed. Once I was in position I closed my eyes, telling myself that everything would soon be over.

The next thing I knew, I had a blindfold put across my eyes, it smelt of rubber. Not only that but I could feel some sort of rope being tied around my right wrist. Soon after, my left wrist followed, then my right ankle, and finally my left ankle. I didn’t know what was happening but I felt really nervous about what was to come.

“Now, let’s begin...”

Slowly but sensually, I started to feel the buckle of my belt being undone, and in one fell swoop, pulled away from my pants. This was followed by the zipper of my pants, being slowly and teasingly unzipped, revealing my crown jewels

“Wow you’re shaven, and a pretty neat job at that. No underwear too mmm, what a naughty boy you are... Hehe of course I know! I asked you to go commando, and I’m glad... you listened”

“Now, how does it feel... to have My supple little hands wrapped around your...little... dick.”

Just then, I started to feel her tiny but warm hands wrapping around my dick. I won’t deny it but it felt really good. The more she played with my dick, using her fingers to toy with the tip of it, occasionally giving it a few strokes, the harder and more sensitive it got.

“Wow, just a bit of stroking and teasing... and you’re already so hard? Oh My... you’re such a slut aren’t you? Getting all horny in a situation like this, well... I can’t let you experience only pleasure, this IS supposed to be a torture session for you. How does it feel to have My pointy nails digging right into your balls?”

Out of the blue, I felt something sharp pressing against my balls, forcing my body to react, making me struggle helplessly against the restraints. I shrieked in pain as I begged Caittrin to stop.

“Sssssssh... you’d disturb the neighbours, keep your volume down. Here’s something to keep your mouth busy while I enjoy your body...”

The next thing I knew, I had some sort of a ball-shaped silicone put into my mouth, and fastened around my head that was preventing me from making too much noise.

“Awwww, you look cute all tied up with that red ball gag in your mouth, let Me take a few pictures for safekeeping. And oh My, that THING is still so hard? You truly are one big slut aren’t you?”

Caittrin then started to crawl onto me, advantage of being such a tiny girl I guess. She removed the blindfold and to my amusement, there she was, clad in a tight latex bodycon dress. Arm-long latex gloves with knee-length boots, giving her an impression of a height boost. But what scared me the most was what she held in her hands, a pair of nipple clamps.

“Now... they say that guys tend to have less sensitive nipples than girls. Help Me prove them wrong okay???

Slowly and teasingly, she started unbuttoning the centre buttons of my dress shirt, revealing my nipples that were for some unknown reasons, erected and standing at attention. Using her fingernails, Caittrin started dragging them across my chest, careful to apply a little more pressure on my nipples with her nails, making me squirm into the ball gag each time. After she was done and satisfied, using her index finger and her thumb, she rolled one side of my nipple between those 2 fingers, and after a few rubs, used one side of the clamp for that nipple. She then repeated the same process with the other side of the clamp for my other nipple, all the while, smiling to herself at the predicament I was in, only able to squirm in pain into the ball gag and struggle against the ropes.

There I was, shirt half unbuttoned and having only my chest exposed with a pair of nipple clamps torturing my nipples as though I were some pornstar, all tied up and restrained with a ball gag in my mouth.

“Now, let’s get back to the main course, shall we? Look at that throbbing hard-on of yours, leaking so much pre-cum already?!”

Using her fingertips, Caittrin rubbed against the tip of my hard-on, picking up all the pre-cum along the way and cleaning it against my face.

“Now, here’s a sexual education lesson for you, I’m going to show you how WE girls use sex toys and you’re going to experience one of these sex toys yourself! Doesn’t it sound fun?”

Reaching out under the bed, Caittrin takes out what I’ve only seen in the occasional porn videos that I’ve watched, a huge-ass Magic Wand. I swear it was way larger than I had expected it to be when seen up close.

“Remember, don’t you dare cum without my permission. If you do I’m sending that video straight to the school disciplinary board, no arguments”

I looked at her, nodding in agreement as I continued to stay anxious about what was to come.

Carefully placing the wand against the tip of my hard-on, Caittrin turns it on to the lowest setting, letting it vibrate against my sensitive hard-on as she tugged on my nipple clamps occasionally. And surely enough within tens of seconds I was already at my limit and about to burst my nuts. I started struggling against the restraints, mouthing into the mouth gag the words “please can I cum?”

“That was fast?! It wasn’t even a minute. Oh My, you’re WEAK. Maybe let’s try that again okay? I’m going to give you 30 seconds and you can only cum on the 30 second mark okay? Any earlier or later and I’m sending that video”

I nod in agreement and soon enough, the countdown started. Caittrin turned the wand on once again and placed it against the tip of my hard-on, but this time she didn’t use the lowest setting, she had set it up one notch higher as I could feel the strength of the vibrations being way stronger this time.

“30, 29, 28, 27, 26, 25”

I was already at my limit 5 seconds in, how was I to hold out for another 25 seconds, but I knew I had to listen or my life would be ruined, and so through sheer determination, I gritted my teeth against the ball gag and held on...

“24, 23 22, 21, 20, 19, 18, 17, 16, 15”

At the halfway point, Caittrin sneakily turns up the vibration strength one more notch, making the wand do work much harder and stronger. By this time my cock was so sensitive and throbbing so hard that I was even afraid of cumming...

“14, 13, 12, 11, 10”

At this point, the door opened. In came one of Caittrin’s friends that I recognised would always be hanging out with her.

“Just in time, I’ve got My little plaything here just about to cum, stay around for the show!”

“9, 8, 7, 6, 5, 4, 3”

The wand goes up one more notch, making the vibrations much more intense than before. I struggled to keep myself in check and more importantly not cum until the 0-second mark.

“2, 1, 0”

At this point, I stopped all my struggles and shot out, load after load, shot after shot, shooting cum all over my own body and shirt. It was the most intensive cumming I’ve ever had in my whole life. My cock was throbbing so much even after that intensive cumming and it was even more sensitive than ever.

Just as I was catching my breath, my mind was still in a state of blank, blatantly ignoring the fact that one of Caittrin’s friends just walked in on me cumming like a pornstar and my cock still being exposed.

“Good boy, you didn’t cum too early, I was surprised you could hold out. Enjoyable wasn’t it? Now, I’m going to go for a quick supper with my friend here and when we’re back, we’re both going to be enjoying ourselves playing with you okay? The night ain’t over yet little boy, and meanwhile, here’s something to keep you entertained and all aroused up”

Caittrin took her laptop and placed it in front of me, turning her laptop to some lesbian femdom porn video, and while she was at it, she took a smaller vibrating wand and using some ropes, placed it against my sensitive hard-on and turned it up to the smallest setting, enough to keep me aroused and bothered but not enough to let me cum.

“Be right back dear, stay horny for Me... will you? We’re going to have a long night”

As Caittrin closes the door behind her, locking it, I started to think about what just happened, but soon enough my sensitive hard-on started to remind me of the vibrating wand that was there and my thoughts were distracted towards what was happening down there instead.

[ To be continued in MEMBERS ONLY STABLE ]

Special thanks to Pet Q for the erotica submission + Edits by Yours Truly .

*Disclaimer: Note that the write up above is fictional and consists of CNC scenes. None of these events occurred in reality and any resemblance is just a coincidence.

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1 Comment

Pet Rob
Pet Rob
Apr 06, 2021

Dear Mistress Caittrin,

This is a nice start.

If only this could happen to me in reality.. looking forward to the rest of the story.

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