My New School Ch. 01

"For the next five days, not counting weekends, you are not allowed to have any covering whatsoever. This includes towels, underwear, hats, socks, or shoes. You must remain completely naked until Friday, including today and tomorrow. Is that clear?"

I couldn't believe it! How could this be right?

"We teach accountability here at Stephens, and since you weren't accountable enough to ensure the proper swimwear, resulting in lost clothing, this is your punishment. Next week, I expect you to have proper attire for my class. Do you understand, Mr. Quinn?"

"Yes, Ms. Clark. I understand." I said sheepishly.

She then turned her attention to the rest of the class. "Now, beginning this semester we are implementing a new addition to this punishment for students. Robbie! Bring me the box."

Uh oh. This wasn't looking good.

A male student in a small Speedo came forward holding a box about the size of a shoe box. Ms. Clark opened it, and pulled out a bottle of clear gel. "Mr. Quinn, take this bottle, and apply a generous amount of lubricant to your rectum, then resume your position with your hands on your head."

I did as I was told, and spread a sizable amount between my ass cheeks, making sure to lube up my asshole really well, as I had no idea what was going to happen next. I then put my hand back on my head as I was told.

"Now students, in this box are two different items, one for females, and one for the males. The female item," she held up what equated to a vaginal butt plug, " is this device. It is to be inserted directly into the vaginal opening, and not to be removed until lights out at 10 pm. Once 6 am comes, you must reinsert it, no exceptions." She then pulled out a smaller object, thankfully, that was for the males. "This is part of the male equivalent. Same deal, out at 10, back in by 6. This piece," she held up a rubber ring with a rather large bulge on one side of it, "goes around the shaft of the penis, and must be placed back on the offending student by 6 am every morning."

I couldn't imagine a worse punishment. I had to face the entire student body, naked, with a sex toy in my asshole, and a cock ring on. "Mr. Quinn, turn around, face the pool, and bend over and grab your ankles."

Again, I did as I was instructed. Ms. Clark lubed the long, curved, black object and gently inserted it completely in my ass. The only thing keeping my hole from swallowing it were two rods at the end, shaped like a "T" that fit between my ass cheeks, and then right behind my balls. She then took her hand and lubed up the ring, then grabbed the shaft of my dick and lubed it up as well. I could already feel the pressure on my prostate similar to the doctor's finger earlier in the day. Each small muscle I moved, worked the device to apply pressure, not only to my prostate gland, but to the area between my balls and my asshole. This was an entirely new sensation, and it would've been quite pleasurable had it not been for the humiliating factor of such a large audience, that would only grow larger in the coming days.

The swimming instructor then slid the ring onto my cock, with the large bulbous piece pressed against the tops of my testicles. She then took two elastic strings with plastic hooks on the ends, and used them to tie the ring to the device in my ass. "This is to ensure that the ring stays firmly in place, regardless of the student's arousal level. You may now turn around and put your hands back on your head, Jason."

I stood and turned to face the students. A mixture of shock, disgust, and curiosity was spread among their expressions. Ms. Clark then reached in the box one final time, and pulled out a small rectangle with a button on it. "This, is the controller for all the devices deployed at any given time. One push of the button and it sends a signal to every device at once, initiating a very strong and powerful vibrating function, lasting no less than thirty seconds, and up to twenty minutes."

She gave one quick push of the button and suddenly both the insert, and the ring began to vibrate almost violently. I was instantly overcome with the sensations, and I fell to the floor. Every muscle in my core was in a full spasm, sending shock wave after shock wave of overpowering sensation throughout my whole body. After fifteen seconds of this, I came. It rushed out of me so hard, and so fast that some of my ejaculate almost landed on the feet of the people in the front row of the bleachers. It was still going, and I was still unable to do anything but lie there, naked, writhing in a mixture of embarrassment and great pleasure.

When it was over, I looked up, and to my horror I saw her. Samantha. The girl I was supposed to have the date with tonight. Oh no, I couldn't now. There was no way I was going to a party, naked, hooked up to super powered sex toys. Even watching a movie with her would be too much humiliation to stand. Sure her friends had seen me naked before, but she was different. She was supposed to be the one deserving of it, not just seeing it based on circumstance, yet there she was, looking down at me, then down at the puddle of semen at her feet. I couldn't look her in the eye, there was no way.

"Ms. Charleston," barked the instructor. "Join your classmate here at once. Mr. Quinn, get up and resume your position."

I slowly got up off the ground, my legs barely able to support myself as they were shaking so badly. I closed my eyes and put my hands on my head, wishing so badly that this would be over soon.

I heard someone walk up from the bleachers and stand next to me. "Remove your suit and put your hands on your head," I heard Ms. Clark say to the girl. "Now, apply this lubricant to your vagina, then bend over and grab your ankles, just as Mr. Quinn did."

I opened my eyes to see Samantha, standing next to me, stripping out of her one piece swim suit. Her small, firm tits sat nicely against her body, her tight toned stomach led down to a shaved pussy mound, and her long, skinny legs just completed the package. She turned around and bent over, allowing me a look at her from behind. Her tight, pink pussy peeked out from between her legs, just below her small, puckered asshole. She was the most amazing girl I'd ever seen, and she was about to be violated in a similar manner that I just had.

"Samantha's punishment is for talking back to me on Friday. Apparently she decided that she knew better than I when it came to who had passed the swimming test last year, and who hadn't. Now, while she was correct that she had previously passed, her tone was entirely too disrespectful for her to address an instructor with. She shall now receive the same punishment as Mr. Quinn here."

I watched as Samantha slowly inserted this bulbous device between her tight little pussy lips. Moisture was dripping from around her opening as she slid it further and further inside of her until finally, she had it in all the way. "Now stand up and resume holding your hands on top of your head."

She did so as she looked over at me, a slight twinge of fear showed through the look of utter humiliation on her face. "The last demonstration was only a test, in reality each time a signal is sent to the devices, it will increase the time amount, double the last one. The test signal was thirty seconds, this next push will be a full minute." I braced myself for what was coming next. I looked over at Samantha, and gave her my best look of support. Just before Ms. Clark could hit the button on her remote, I grabbed the girl, and held her tightly as she held me back. Suddenly, we were both pulled to the floor, and wrapped in each others arms, we had to endure a full minute of this punishment.

After it was over, we were all dismissed from the test, and told to return to our dorm building. Samantha and I walked together, hand in hand, back across the courtyard to the stares of several hundred students, all gazing at our nudity and genital adornments. We went straight inside and up to our rooms. We parted ways in the hallway after she asked for a rain check on our date night. "Given the circumstances, I agree." I told her. I kissed her on the lips after we hugged one more time and closed our doors.

* * *

"Dude, what the fuck happened to you?" Mike asked when I came in naked and exhausted, then collapsed on the floor in front of the door.

I explained the medical exam, the prostate exam, and then the swimming test. "I should've packed my swim suit with everything else I brought with me," I said. "And what's worse, Samantha had to do the same thing because Ms. Clark didn't like her attitude. We've had to postpone our date."

"Damn, that really sucks, Jason. Look, I know it's not a good time right now, but Brittany saw me in the hall earlier. She apologized for the way she treated me after seeing me at dinner last night. She asked if she could come over and hang out tonight. Is that okay with you?" He asked, clearly putting his roommate before his sex life.

"Absolutely, Mike. She's seen me naked twice already, it's not like she's going to see anything more than she has of me. She was there for the whole prostate thing."

"Are you sure? You look exhausted."

"Yeah, I'm positive. I'm going to go to sleep now," I said as I slowly got up and walked into my side of the room. I once again dove face first into my bed, and buried my face into my pillow and closed my eyes. A few minutes later, Mike walked into my room.

"Hey, Jason?"

"Hmm," I grumbled from the pillow.

"I feel so bad about what happened to you today, I should've said something, and I definitely should have offered you the use of my swimsuit."

"Don't worry about it, Mike. It's cool man. I should've read the rule book."

"Maybe," he said, "but you're new here, you had no way of knowing. So, in a small show of solidarity, look at me."

I slowly lifted my head up to find Mike, standing completely naked by my bed. "I'm going like this the entire week that you have to, though I don't have the devices inside of me, I hope it helps relieve some of the humiliation you're going to feel."

"It's okay, man. You don't have to do that for me. Besides, Samantha is in the same boat as I am, it'll all work out."

Just then, there was a knock at the door. Without warning in walked Brittany, just as Mike had made his way back to his side of the room. "Oh, wow. Mike, you're naked!" She said, happily.

Mike then explained what happened to me, and why he was now without his clothes. "It was kinda my fault, Brittany. I owe it to him."

"That's so sweet! Samantha has the punishment, too. Fuck it!" She said, as she stripped bare with us. "I'm going naked, too now. The nudity is bad enough, but the sexual component? That's too far. We can show the administration that we don't agree with their tactics, if we show up naked, too, it'll take some of the edge off of what they see as something bad."

"Thanks Brittany, I'm glad you understand."

"You're so sweet, Mike. I've always liked that about you."

After that they didn't say another word, they laid on his bed and kissed each other.

Soon, there was another knock at the door. "Jason?" a sweet voice called out. "Can I come in?"

I got up and opened the door to find Samantha standing there. "I don't think you want to, Mike and Brittany are having a moment," I said with the best half-laugh I could muster as I stepped into the hall with her.

"Actually, I really don't want to be alone tonight. Can you come stay with me?"

"Sure. If we're going to go through this punishment, we might as well go through it together, right?"

"I'd really appreciate that, Jason. Thank you."

We stepped across the hall into her room. She put on a movie and we laid in her bed together until it was time to take out the contraptions we had forced upon us.

I helped her remove her device, and she helped me remove both of mine. We still weren't allowed to wear any clothes, but at that point, it really didn't matter. We laid back down and she asked, "Would you like to sit on the balcony with me? It's a really nice night outside."

"Sure," I said as I followed her out the door, and into the night with the stars shining brightly overhead. We stood out there for a few moments, holding each other until I leaned over and kissed her.

"That vibrator made me really horny, and seeing you naked is about to push me over the edge right now. You know, I've never had sex outside," she whispered.

"Me neither," I said back softly.

"Do you think we'll get in trouble for having sex out here?" She asked, seemingly concerned with what the punishment might be.

"We already are in trouble," I said, with a devious grin.