This story is an excerpt from the fifth book in the “Tricked Sissy” series – “Tricked Sissy 5 – A Free Sissy” – in which Chloe is offered a deal by her blackmailer, Nate: beat him in a racing videogame, and he’ll delete the video evidence of her being a little slut. Fail, and she will have to pay for Nate’s silence not just with blowjobs, but full on fucking!
This nearly 45,000 word erotic story contains very explicit adult material, including oral sex, masturbation, anal play, gay sex, CNC, BDSM, voyeurism, exhibitionism, chastity, being tied up, and more. This story contains ONLY ADULT CHARACTERS and is strictly for ADULTS ONLY!
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Chapter 5 – The Game Proposition
The rest of my day had been filled with dirty looks, hushed comments, and even a few more “accidental” gropings. Two other teachers called me out for my outfit (coincidentally, two female teachers!), and one other didn’t say a word but stared at me during his entire lecture.
It was the end of my last class of the day, and I was looking forward to going back to my dorm and putting on less slutty clothes. Maybe even use a dildo to give myself some relief, as the butt plug would constantly bring me to the edge and then stop, leaving me in a sexually frustrated mess! But a sudden chime on my phone would result in me delaying my plan;
“Saw you around today. Love your style choice!” Read the message. “Stop by my dorm after your class – don’t bother changing. I have a proposition.”
The message was sent by Nate – a jock with short, dark hair, smooth face, and dark blue eyes. He was friends with Neil and Chris – the jocks who recorded me as they fucked me when I was tied down to a park picnic table.
Nate had seen the video and had recognised me on my first day in college. Ever since, I was required to “pay” him in order for him not to share the video with everyone else. Basically, I was being blackmailed into sucking him off every day!
Although at this point everyone pretty much knew I was a slut, yet no one had any actual proof. The last thing I needed was to have a very explicit video of me going viral!
Resigned to my fate, I agreed to meet him at his dorm after my class.
“At least,” I thought to myself, “I’ll be able to record myself sucking him off and get one person closer to my target!”
Thankfully the class didn’t drag on for much longer, so in no time I was heading towards the same building my dorm was located. But instead of going to my room, I found Nate’s door and knocked.
“Door’s open. Come in!” Came a voice from inside.
To my surprise, his dorm was quite different from mine! At least one half was; while he had a bed to one side of the room as standard, in place of a second bed, Nate had a big TV against the wall and a two person grey sofa facing it, where he was currently seated at, wearing a sport branded white shirt, black slacks, white socks with no shoes. It seemed like he never got assigned a roommate, so he turned one half of his dorm into a gaming station!
“I’ll cut to the chase, Chloe,” he said, not bothering to look up from the TV as he sat there, controller in hand, racing a Formula 1 car. “I want to give you the opportunity to… let’s say, ‘buy your freedom’ from your obligations to service me in exchange for my silence regarding your gangbang video.”
“I’m listening”, I answered, intrigued and still standing by the door.
“You race me in this game for 15 laps. If you win, I’ll delete the copy of the video and forget the whole thing. You won’t have to suck me off daily anymore.”
It was an interesting proposition. Part of me would miss the embarrassment of jerking him off in class, or having to blow him daily, anywhere he wants. But a bigger part of me didn’t want to deal with that asshole anymore. Yet, I sensed a catch:
“And if I lose?”
“If you lose, I’ll obviously keep the video and you’ll have to continue servicing me – the kicker is that now I’ll be able to fuck you instead of having you just jerk me off or suck me dry.”
That was quite a risk and I was not sure if I wanted to take it.
“What if I don’t accept this amazing opportunity?” I asked sarcastically.
“Our deal will remain the same: whenever I call you, wherever I am, you must make me cum with that velvet mouth of yours.”
“And how good are you at this game?”
A second after I asked, his car flew into a wall and the words “Game over! You lose!” showed across the screen.
“Does this answer your question?” He asked as he turned sideways to finally face me. “I just got this game today, so I’m quite shit at it.”
I couldn’t tell if he was lying and luring me into a false sense of security or if he was being genuine.
I took a second to mull it over, pretending to not notice him checking me out with hunger in his eyes.
“Deal!” I said as I walked over to him, extending my hand to shake on it.
“Deal it is!” He shook my hand back. “Now sit down, let me show you the controls. And one more thing: don’t think about cheating, or this whole proposition will be null and void!”
As I sat down, I considered asking for a towel of sorts to avoid any fluids coming out of me and staining his sofa, seeing as the plug was still vibrating in me, albeit at a lower setting (maybe the battery was running out?). I decided against saying anything; if he didn’t want my nearly naked ass on his furniture, he shouldn’t have invited me over!
I was also a bit worried at the size of the sofa: although it was a two-seater, it was so tight that our legs were touching. But comfort was not on my mind right now: all I wanted to do is win!
Once he showed me all the buttons to drive the car, he pulled up a split-screen mode of the game and we began racing. Nate had a slow start because he insisted on staring at my legs as we waited for the green flag, but my advantage was short lived as he took me over. The game was far from lost! Fifteen rounds would be enough time for me to recover!
I struggled at first, but was soon closing in on him! Yet I was still struggling to overtake without crashing.
Nate was in the zone and seemed to predict all of my moves before I got a chance to execute them! Suddenly we were 5 rounds down and I was starting to worry.
That’s when I had a stroke of genius! What if I managed to distract him enough so he either crashes or makes a mistake and lets me by? I knew he was turned on by how I looked, so I decided to use that to my advantage.
While still focusing on my own driving, I stood up from the sofa and took one step forward, being careful not to obscure his view and get called a cheater. Instead, I started moving my hips to an imaginary beat; slowly and gently at first, but soon picking up speed and really shaking my ass!
Looking back at him, I could tell he was straining to keep both eyes on the game, as he would often steal half-a-second glances at my booty.
It was working!
Then I tried to bend over at the hips, almost thrusting my ass into his face. His car immediately skidded as his eyes caught my buttplug covered hole, but because of my position I couldn’t press the correct buttons to take advantage of his mistake!
“There’s no point in doing that, Chloe. As you can see, soon enough I’ll not only be able to stare at that tush, I’ll also be sticking my cock deep inside of it! You can’t distract me!” He said as he recovered his car and remained ahead of me.
Starting to feel frustrated, I sat back down.
Suddenly his taunt gave me an excellent idea: what if I played with his dick? Surely that would make it much harder for him to concentrate! Plus I wouldn’t technically be cheating!
With a renewed sense of purpose, I kept my eyes on the TV as I lowered myself sideways onto his crotch, placing my cheek over where his member would be. I could sense a semi erect object under the thin fabric of his slacks and began rubbing my face against it.
It took only a few seconds for it to come to life, getting harder as I increased the weight of my head on his lap. Nate was obviously not wearing anything underneath, seeing how his pants were now tenting just below my mouth.
Nate was indeed finding it harder to concentrate, but he was still just ahead of me in his car. I knew that if I kept it up, sooner or later he would make a mistake, and I would be able to overtake him!
We still had 7 laps to go, so I upped the ante by wrapping my mouth around the tip of his tented slacks, applying some pressure with my teeth on the head of his covered cock, and even slowly bobbing up and down.
But another lap went by and still no dice. If I wanted to win, I would have to do something more drastic!!
Taking my eyes off the screen and, as fast as I could, I held the controller in one hand and grabbed his black slacks by the waistband, yanking them down. He instantly and instinctively lifted his butt just enough for me to get them down to mid-thigh.
His uncut 6 inch thick cock immediately sprung up, unconstrained by his lack of underwear.
My car had spun in the split second it took to free his joystick, so I had to quickly regain control as I slowly lowered my head back onto his lap.
All the while, Nate hadn’t even bothered to look away from the game, clearly determined to win! I was having none of it; I wanted to win, not just to earn my freedom from his blackmail, but to also show him who’s boss!
While keeping my eye on the screen and fighting to get my car closer to his, I opened my mouth and stuck my tongue out, pressing the tip against the tip of his erection. My plan was to tease him as much as possible so he’d lose focus and mess up, so I was about to use all my cock sucking abilities!
As light as a feather and as slow as a sloth, I ran my tongue down his shaft, which had an immediate effect on him as he shivered and almost lost his focus.
“Oh you slutty sissy!” He breathed in with a smile. “What did we agree on about cheating?”
“I’m simply paying you for your silence, as we agreed! How’s that cheating?” I asked with his dick poking my cheek.
“I never told you to start sucking me off now!”
“Well, ok then…” I said, before wrapping my lips around his head as my tongue circled it twice. I then took my mouth off his tool. “You want me to stop then?”
His member throbbed, giving away his true feelings.
“Go ahead and suck me off then. I’ll still beat you!”
“We’ll see!”
I engulfed as much of his cock as I could, trying hard to give him enough pleasure while also focusing on the game.
Bobbing my head, I had to find a speed in which my vision wouldn’t be blurred by the movement . I made sure to drool enough to coat his stick and make it a very sloppy blowjob, as well as using all of my tongue. I didn’t have to look at him to know my distractions were working, as my car finally caught up with his.
Now with only 3 laps to go, I just had to make sure he either came in my mouth (which would be distracting enough for an overtake), or close enough without going over the edge, so that would frustrate him into face fucking me and forgetting about the game entirely!
I opted for the latter, as I wouldn’t be able to pull my phone to record him jizzing into my mouth – and, frankly, what was the point of sucking someone off if it didn’t mean I would be closer to finishing Sarah’s task, and consequently, getting to finally fuck her?
As I felt him getting closer, I took my mouth off him and let my parted lips hover just a hairline above his tip so he could feel the warmth of my breath, but nothing else.
“Don’t fuckin stop!” He growled.
“Only if you intentionally crash!” I bargained, hoping his horniness was so high up, he’d do anything for relief.
“It’s too late for that, my dearest cock slut!” He said with a smile.
It then hit me: not only were we on the final lap, it was the last corner and he was just ahead of me!
I panicked and mashed all the buttons on my controller at once, yet that only resulted in my car swerving in the wrong direction and hitting the barriers, just as his crossed the line and the words “winner” were displayed on his side of the screen.
I instantly knew I was fucked – or better yet: was about to be fucked!
I needed to get away fast, so I leaped from the sofa and made a beeline towards the door!
Sure I had lost the bet, but there was no reason to make it easy for him! After all, he didn’t say he wanted to fuck me right now, so as long as I made it outside and ran away, I’d be able to buy myself some time!
But Nate was a jock. A fit jock. A fit jock with incredible reflexes.
I barely touched the doorknob before I felt his arms wrap around my waist from behind, lifting me off the ground and away from the door.
“Noooo!” I protested, despite secretly enjoying being manhandled.
I tried kicking my legs and throwing myself towards the door, but Nate was thankfully much stronger than me. I could feel his still erect cock being slapped against my legs.
In one continuous motion, he swung me around and threw me down onto his bed, nearly making me bounce right off it as I landed on my tummy, knocking the air out of me.
Before I could react, Nate hopped on the bed and sat on my thighs, his own legs pressing mine together. He grabbed my hands and bent them backwards so they were folded across my lower back. His strength was enough that he could hold both my wrists with one hand, leaving the other free to grab my frilly boy shorts.
“I’ll take my payment now, sissy!” He growled in my ear.
There was the order. Nothing more I could do now.
As he began pulling the panties down, I lifted my hips as much as I could so he could pull them over my butt; I couldn’t risk him completely tearing the panties to shreds as I still needed something to cover me when I walked back to my dorm later (even something so see-through was better than nothing at all!).
“If you had just let me cum in your mouth, I wouldn’t have had the energy left to fuck you now. I bet this was your plan all along, you cock hungry whore!”
Yeah, I should’ve thought about that. But it was too late now.
Nate was impatient and didn’t waste time grabbing my plug by its base and pulling it out. I moaned at the sudden emptiness, and wondered for a while if the cum from that boy earlier today was still sloshing around in me, possibly now leaking from my hole.
But if it was, Nate didn’t seem to care; I felt some warm goo hit me right on my starfish and I assumed it was Nate spitting onto my hole to give some lubrication.
“I’m actually so good at this racing game, that I could win blindfolded. You were only close because I allowed it, but you weren’t ever going to win, sissy. And deep down inside I think you knew it. But you couldn’t resist getting fucked by me, could you?”
Before I could answer, Nate pressed the tip of his cock against my pussy and let it slip in all the way, laying his body on top of mine. With his legs squeezing mine, it made my opening smaller and tighter – and also made it feel like he was much thicker and bigger than he actually was, resulting in some pain for me.
At first, I tried to squirm away, but that only made me press my cage against the bed and have his tool rub against my p-spot. Once he begun pumping, I gave up and resigned myself to just take it and try to enjoy it! Nate must’ve felt my arms relaxing, so he was able to let go and use both hands as leverage on the bed.
Due to my teasing earlier, I knew he wouldn’t last more than 5 minutes, which wouldn’t be enough time for me to reach an orgasm too. I did try to reach around him at one point to insert a finger or two in his behind as I knew he secretly liked it, but the position he had me in made it impossible.
Nate didn’t say much more as he continued to thump his body against mine, his dick slamming deep in me. The only noises were his primeval grunts, like a predator taking its prey.
Soon enough, his body stiffened as he reached the peak of his pleasure; he gave one final shove and let his full body weight rest against mine, as I felt his cock twitching and filling me up with his cream. And just as I was starting to warm up!
He stayed on me for a few more seconds, catching his breath. When he was done, he slowly pulled out. I could feel that the pressure in my insides was beginning to expel his seed, but Nate was quick enough to insert the plug back in, ensuring nothing leaked onto his bedsheets.
Before hopping off, Nate rubbed his wet noodle against my butt to clean it up. He didn’t even bother helping me up, rather just went back to his sofa to continue gaming!
I had to pull up my own boy shorts as I got off his bed.
“Remember, that ass is now mine!” He said, not taking his eyes off the game as I walked towards his door.
Seems like my whole body was everyone else’s property!
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Love and kisses,
Chloe