Training My Unwanted Roommate

I applied for a single dorm room even before I was accepted to the college. Not that I was anti-social, quite the opposite, but I was appalled by the idea of sharing a bedroom with a stranger.

Still, it seemed I was out of luck. With only days left before the semester started, I had to accept a double. To make matters worse, neither of my parents had the time to drive me. This meant spending 8 hours on a train and not bringing more luggage than I could carry.

By the time I'd arrived, picked up my keys and found my room, it was already quite late. I was tired, hungry and in a very bad mood. All I could think of was getting to bed as soon as possible. I had even forgotten the whole roommate thing.

That, however, I was reminded of the very instant I swung open the door. One of the beds was located less than a meter from the door. The first I saw of my roommate was his bed covers being quickly rearranged. He had obviously been fapping when I interrupted him.

None of what happened next was planned. Nor would I say it's representative for how I usually act. But being tired, hungry and annoyed can change anyone.

I let the door close behind me. He was staring at me and I at him. His face was bright red, which was hardly surprising in this situation.

None of us said anything for a few seconds.

"Hi, I'm -" he started.

"Were you fucking wanking?!" I interrupted, unloading all my built-up frustration onto my new roommate.

"I was... Ehm..." he hesitated. "Uhm, no I mean -"

"It's not a difficult question," I shouted at him. "Were you or were you not stroking your meat?"

His evening had not gone the way he had anticipated. Now he seemed confused and embarrassed.

I was steaming, allowing myself to keep unloading my frustrations.

"Well, were you?"

"I..." he whimpered. "Yes..."

"What was that?" I kept shouting. "I can't hear you."

"Y... yes," he said.

"Yes what?"

"Eh, yes I was... I was masturbating."

His face was even redder than before and he was cringingly holding on to the edge of the duvet.

The shouting had helped and I felt calmer. As I was thinking of a way out of this awkward situation, I realized that I was actually quite curious as to how far I would be able to take this. I decided not to pull back, but to instead continue and see where it led.

"So, are you gonna finish?" I asked, not shouting anymore, but trying for my most dominant tone.

He stared at me, face still bright red.

"No, I ..." he stuttered. "No, I'm ... eh ... I'm good."

"Finish," I said sternly, fixing my eyes on him. "Finish what you started so we can get this over with."

He looked nervous, bordering on scared. I kept my eyes fixed on him and did my best to maintain a stern and serious face.

Nothing happened for quite some time. He gulped nervously, and one of his hands slowly let go of the duvet and disappeared down under, towards his groin.

Not being able to find any other way out, he had decided to do as he was told. And I could see he started to slowly tug on his dick.

I've never really been dominant before. And I don't think I'm intimidating enough to dominate anyone like this in any other situation.

But for a freshman college kid, who probably moved out from parents' only days ago, it doesn't take much. Add to that, having just been caught red-handed and then yelled at by a stranger, that'll put you in a vulnerable situation.

He wasn't looking at me anymore, instead he tried to focus on the task at hand. I did my best to keep up the appearance as the dominant man in the room. It must have worked because he really did seem to put in the effort.

After a few minutes, I started to get bored watching his hand bobbing under the duvet. I grabbed it and yanked it off him. Too quick for him to try and stop me, but he was quick to cover his junk with his hands.

"I did not," I talked slowly and with my most dominant voice, "tell you to stop."

He looked up at me again. Now he seemed desperate, almost pleading.

"You have one minute to get it done," I was making it up as I went. "Or you'll wish you had."

My empty threat had worked. Reluctant at first, he started to pick up his wanking again. He struggled to get hard, but once he got it up he soon got his pace back up.

I had no idea how long he kept at it. Neither did he, for all I knew, so it hardly mattered. It did, however, seem like he was having some progress. He might even have started to enjoy it.

If I wanted to torment him further, now was the time. And no matter if he enjoyed it or not, I knew I did.

"Time's up!"

He was close and it was obvious that he wasn't planning to stop. This didn't surprise me in the least. However, I think my retribution surprised him.

Before he could see it coming, I whacked my fist square in his balls. I knew he would protect himself from a second blow, so I decided to go all-in on the first.

He groaned at first then whimpered.

"You had your chance," I told him. "Now go to sleep."

His dick had gone soft instantly after my fist hit his ballsack. He was clutching his aching nuts, as to comfort and protect them.

I paid him no attention, took off my jacket and opened up my bag to get my bed linen. After I made my bed I went to brush my teeth. When I got back he was back under his duvet sleeping. Or, more likely, pretending to sleep.

Feeling quite pleased with how the evening had turned out, I stripped down to my boxer briefs and got in bed. It had been fun and I was curious how far I could continue my ad-hoc experiment. Maybe sharing a room would be so bad after all.

*

Something woke me up a few hours later. Turns out my roommate was at it again. To be honest, I was surprised that he'd be up for it again so soon. Guess his raging teenage hormones kept him from getting any sleep and this was the only solution he knew of.

That's when I decided: if he was going to wake me up at night, I'll be using him as my toy from now on.

I listened quietly for a while. My plan was to let him get close before I interrupted him. It was difficult to tell exactly how close he was, but I decided to get up.

He looked terrified and stopped immediately. I pulled off his duvet and he instinctively hurdled up towards the corner and covered his junk with his hands.

"That's it," I said. "From now on, as long as you share a room with me, you don't get to cum unless I tell you to. Is that clear?"

He didn't reply.

"Is that clear?" I repeated.

"Yes," he whispered.

"Good. Now get soft and go back to sleep."

He gulped and looked down to where his hands were desperately trying to conceal his boner. He knew as well as I that it wouldn't go soft on it's own anytime soon.

"You better get it down quick or I'll have to force it down."

I looked at him and he looked back at me in panic.

"Put your hands behind your head."

He didn't obey but kept trying to conceal his boner with his hands.

"Now don't make this harder than it has to be. Put your hands behind your head or I swear I'll make sure you'll regret it."

After a short moment of hesitation, he did as he was told. He closed his eyes and clenched his teeth, so he probably had a pretty good idea of what was coming.

This time I managed to get two rapid blows to his balls, one with each fist. His reaction was almost identical to last time.

I dropped his duvet on the floor and got back to bed.

"If you wake me again, trust me, you'll be sorry."

My threat had worked and I slept until 11 the next day. When I woke up his bed was empty.

At first, I thought he had pulled up and left altogether, but I soon realized that he was just out. Most likely, he was emptying his nuts somewhere. I finished unpacking and went for a stroll around campus.

*

My roommate didn't return until around eight that night. He opened the door slowly and snuck his head in, as if hoping to find me asleep or, better yet, gone. I was following his odd behaviour with some amusement and when he saw me he flinched.

"Hi," I said.

He came in and dropped his bag on his bed before he replied.

"Eh... hi."

I went back to my books and he kept quiet for some time. It was obvious that this was making him uncomfortable.

"I... eh..." he said after a while.

"Yeah?"

"Last night... I -"

"Yes?" I interrupted.

"I was... I mean I -"

"Look," I interrupted again. "It's not very complicated. If you're going to live with me you follow my rules. Is that clear?"

"But I..."

"Is that clear?!"

"Ehm... yes, I -"

"Good. I don't want to know of any more illicit masturbation and I don't want to be disturbed by you again. Understood?"

"Yes," he mumbled.

"Yes, what?"

He hesitated for a moment.

"Yes... sir?"

"Good. Now Keep quiet and let me study."

The following weeks, we didn't talk much. The semester started and we both were busy studying.

One day, as I got back from class, I noticed a pair of his briefs on the floor. There was nothing unusual about finding clothes on the floor, we were both rather messy, but these had very obvious cum stains on them.

I wasn't so naive that I thought he'd stop jacking off just because I told him (and threatened him) to. But now I had proof that he had disobeyed me, and that meant I could have some fun. The briefs went in my drawer while I went online to order some supplies.

*

A few days later, I was waiting for him as he came back from class. I was sitting arms crossed, with his cum stained briefs prominently placed on the desk in front of me.

He entered quite casually, but as soon as he saw me he started to look very uneasy. Then, when he saw his cum stained underwear on my desk, he froze and just stared at them.

"I -" he tried after a few moments.

I interrupted him immediately.

"It seems you have a problem following our very simple rules," I said.

"I didn't mean to -" he said hesitantly.

"You didn't mean to wank and jizz all over your panties, it just happened. Is that what you're trying to say?"

"No, but -"

"That's enough out of you, boy! You disobeyed me and you will be punished."

"Punished?" he asked.

"From now on, you don't talk unless I tell you to. You lost that privilege when you decided to have a wank in my room."

"But -"

"Not another word out of you! Now get those clothes off and come over here."

He did nothing but stand there, looking like he was trying to find a way out of the situation.

"Don't make me tell you again. Trust me, you don't want that. Now get your clothes off."

Again, he hesitated. Soon though, he slowly started to remove his socks, then his t-shirt. It was obvious that he was stalling for time, but I was in no hurry so I didn't mind.

There was another hesitation before he removed his pants. I said nothing but kept my stern eye on him and waited. This worked and soon he saw no other way out than to take them off.

Now he was standing there in only a pair of tight white briefs. They looked pretty cute on him and I considered letting him keep them for now. Eventually, I decided against it.

"Panties too," I commanded.

He blushed and gulped, but eventually started to take them off. He turned around, so I wouldn't see his junk.

"Turn around."

He did but covered his groin with both hands.

I enjoyed looking at him. He had a nice body and he was so obviously uncomfortable and humiliated by the situation.

"Come over here."

I pushed out my chair and instructed him to lay down over my lap. It's hard to describe the expression of unease and discomfort on his face, but I must admit I loved it and it had made me rock hard by now.

Once more he surrendered any hopes of an escape and lay down over my lap. I let my left hand feel his amazing little bubble butt, caressing and squeezing his round butt cheeks. My cock squeezed against his side, so he could probably tell how much I was enjoying this.

"Now, I think this will be a bit noisy," I said as I picked up his cum stained briefs. "And we don't want to disturb our neighbours. So open up, will you?"

I pushed the briefs against his closed mouth. He clenched his way shut, but using both hands I managed to pry it open and force the undies in.

"Make sure those don't fall out, alright?"

He instantly opened his mouth and spet the briefs out on the floor.

I picked them up and managed to get them into his mouth once again. This time, before I took my hand from his mouth, I grabbed his ballsack with my other hand and started squeezing hard. He moaned and whimpered, but the sound was muffled by the briefs.

"Now don't let that happen again," I said as I pulled his ballsack and squeezed his balls harder. "Do you understand?"

He nodded frantically.

"Good," I said and let go of his balls. "Now I'll have to punish you for being a disobedient wanker."

I raised my hand and landed the first out of many hard blows on his sweet little butt cheeks. He groaned exactly how I had hoped he would.

At a slow and steady pace, I kept smacking his butt, alternating between the left and right cheek. It started to turn a delightful red colour. I paused to stroke his cheeks with my hand, feeling the heat that his sore buttocks were giving off.

I whacked them again and I could hear from his moans and sobs that they were really getting sore. This meant it was time for the crescendo.

Up until now, I had been keeping a slow and steady pace. Now, I upped the tempo, whacking his cheeks a few times every second. This gave his nerves no time to wind down before the next pain impulse.

His screams were muffled but still audible enough for me to enjoy. He tossed and turned from the pain, trying to get away from my palm. Eventually, he fell out of my lap and onto the floor. He ended up laying there sobbing and with tears running down his face. The cum stained briefs were still in his mouth, muffling all his sounds.

"I think that's enough for today," I said. "I trust that you have learnt your lesson."

He whimpered but didn't reply.

"Come here," I said.

He did nothing at first. I reached down to help him up off the floor. His legs were shaking, but he managed to stand up.

"Come," I said and guided him to sit on my lap.

"We don't need those anymore," I said and raised my hand to his mouth. "You can spit 'em out."

He opened his mouth and I caught the spit-soaked briefs. I put my arms around him and he put his head on my shoulder and started sobbing.

"There, there, good boy," I comforted him. "You see now what happens when you're disobedient?"

He nodded.

"And you promise you won't disobey me again?"

"Uhu," he nodded.

"Well, I want to believe you," I said. "But we should take some precautions, just to be sure."

"What?" he asked quietly.

He had almost stopped sobbing and the shaking wasn't as bad any more.

"Stand up, will you?"

He did as he was told. This time he was too distracted to worry about covering his junk.

From my desk drawer, I took out the chastity device I had ordered a few days back. Since I couldn't measure him, I had to eyeball the dimensions and I really hoped it would fit.

"What is...?" he asked.

"You speak when spoken to, remember? You've been a good boy now, but don't make me spank you again."

I put the ring over his balls and cock. I had practised this on myself a few times, so it went on fairly easy. The ring fits nicely, so next up was the part that went over his dick.

This took some fiddling. Fortunately, he didn't become hard. This made things a lot easier. Soon I had managed to lock his cock and balls up.

"Now, if you ever feel that you deserve to cum, you come to me and you ask my permission. Is that clear?"

"Yeah, ehm, but -"

"No 'buts'. It doesn't matter if you want to take a wank or if you plan to bone some chick or dude, don't know your preference and I honestly don't care, you come to me and you ask my permission. I think I've made myself very clear."

"Yes... Ehm... yes sir."

He looked down at his trapped cock and examined the device with his fingers.

"Good," I said. "Now look at the shelf. You see that GoPro, the one with the red light on it?"

"Have you been film-!"

"Shush. You're not to ask questions and if you want to be able to cum anytime soon, you'll do as you're told."

There was an expression of defeat on his face.

"Yes, Sir," he mumbled.

"Now look into the camera and say 'I'm a naughty wanker and I can't be trusted not to play with my wiener all the time'."

No need to say, it took quite some convincing before he would so openly humiliate himself in front of the camera. After proving to him how safe his chastity device was, and that I had no intention of lending him the key unless he complied, he realized that this was his best option.

"I'm a naughty wanker and I can't be trusted not to play with my wiener all the time," he said quietly, looking into the camera.

*

A bit more than a week later, while in class, I got a text from him. It had taken longer than I had anticipated and I was almost feeling proud of him for being able to withstand his urges for this long.

"Please, Sir, I need to cum. Please!" his text read.

Thinking it rude to leave him waiting, I replied at the earliest convenience:

"Clean the room and do the laundry, yours and mine. Do it well, and we'll talk."

"Yes, Sir!" he replied almost instantly.

"Good boy," I thought to myself and got back to the lecture.

When I got back to our room, it had been vacuumed, the beds were made and piles of laundry were gone. The bathroom didn't look bad either.

Moments later he came from the laundry with a huge pile of, at least somewhat neatly, folded clothes.

I told him to put my clothes in my drawers. As he was busy putting our laundry away I asked him:

"So what do you need to cum?"

"Huh?" he replied.

"Do you watch porn, rub your nipples, sniff your armpits? Well, I don't know, what do you usually do when you jack off?"

"I guess I usually watch porn."

"Like on your laptop?"

"Yeah, or on my phone."

"Alright, show me."

He brought out his laptop, went to PornHub and found some video of two generic porn actors fucking casually. It wasn't bad, just very plain and boring.

"Alright, get naked and get started."

He wasn't so reluctant to take off his clothes this time.

"Will you unlock me... Ehm, Sir?" he asked as he was pulling off his pants.

"Yes, of course," I replied as I brought out my keychain. "Would be difficult otherwise, wouldn't it?"

He smiled a little, for the first time.

I unlocked and removed his chastity device. Then I sat on his chair, right next to his bed.

"Alrighty, you got five minutes."

"Wait, are you going to watch?"

"Yes, of course. Otherwise, what would be the point? And for taking back, you now only have four minutes."

"But I -"

"That's three minutes and counting."

He was smarter than to waste any more time. Now he focused only on the video and on his newly freed cock.

It had gone hard the moment it got out of its cage. Now he was stroking it eagerly and I could tell he had a huge built-up need to cum. He was soon moaning as loud as the girl in the video.

"10 seconds left," I called out.

"No wait, please! I'm so close," he said desperately as he increased his tempo.

"5 seconds."

He looked so desperate and I really did believe that he was close. But rules are rules.

"Time's up. Let go of your dick or I'll punch you in the nuts."

He kept at it for two more seconds, but he realized I would follow through on my threats, so he decided to stop.

"Noo!" he cried out. "I was so close!"

His cock was twitching and wet with precum. I couldn't help but smile. My own cocks was just as hard as his by now.

"Please, Sir! Please let me cum," he groaned.