My New School Ch. 01

Brittany and Chelsea began talking about a number of different things, like homework, teachers, and something about a party on Saturday. I didn't catch most of it because they talked so fast, plus I could feel Samantha staring at me silently. I looked over and as soon as I caught her eye with mine, she smiled and turned away in embarrassment. Chelsea then asked her "Hey, Sammy, are you going to the party tomorrow?"

Samantha replied nervously, "I don't know. I don't have anyone to go with, and I don't know that I'd have much fun anyway."

"Oh nonsense," protested Brittany, "It'll be great. Plus, if you ask nicely, I'm sure Jason here would go with you!" I turned to look at Samantha again, this time she just looked at me with a mix of fear and excitement on her face.

"He wouldn't want to go with me, I'm sure he'd rather go with you, Britt, or maybe you, Chelsea." She looked down at the table in front of her, clearly defeated.

"Actually Samantha, I'd love to go with you!" I said.

"R-really?" She asked, looking up with a hopeful doubt in her eyes.

"Of course! I think you're really cute, and what better way to make a good first impression on everyone than taking the cutest girl at school to the party?"

"Oh, you're really laying it on thick here, Jason." She had a bit of of a scowl on her face, and her eyes narrowed making her look less than amused.

"I'm serious, I really do think you're cute, and I'd like the chance to make new friends, plus get to know you a little." I could tell that she didn't quite believe me, but she was definitely getting closer. I could also tell that she like me, and to be honest, I really did think she was the most attractive person I'd seen so far. She wasn't traditionally pretty, not like Brittany was, but I've never been attracted to girls like that. She had more of an exotic beauty to her, whereas Brittany and Chelsea were your typical, stereotypical, cheerleader types. Samantha seemed like she had a lot more going on upstairs than both of them combined, and that really got my gears turning.

"Well, okay I guess. But I'm not much of one for parties, so if I leave to hang out in my room, don't get offended, okay?"

"I won't, I promise. In fact, I'm not much of a party guy myself, so if you'd rather do something else, I hope you'll let me join you." It was true, I never really like parties that much, especially ones where I didn't know anyone.

"Even if it's just going back to my room to watch TV or a movie?" She asked hesitantly, no doubt feeling like her self perceived boring nature would drive me away.

"Especially if it's just watching TV or a movie," I said confidently. "Parties are a lot of pressure and I'd much rather duck out early to go relax instead."

"Really? You're not just saying that, are you?" She asked cautiously.

"Really." I looked in her eyes, they were beautiful, almost a reddish brown color that stirred feelings inside of me that I'd never felt before. It was a little scary, but at the same time, incredibly exhilarating.

"Well, okay." She smiled as her confidence returned, sure at that point that I was telling the truth, though I still could tell she didn't quite believe it all. I felt like she had a difficult time getting attention with the likes of Brittany and Chelsea in her company. They were so outgoing and bubbly, while Samantha was much more subdued, I could certainly see why she might have a tough time.

"Awesome!" I replied enthusiastically, "What room are you in? I'll pick you up at 8."

"I'm in a single room, number 324," she replied.

"No kidding? We're neighbors then! Mike and I are in 325, right across the hall!"

Samantha's eyes got wide and she smiled even bigger this time. "Great! I was hoping I'd get to see you around quite a bit!" She said.

"Especially after what I just told you," Brittany said jokingly. Samantha shot her a dirty look, and I looked over at her with a knowing smile.

Chelsea piped up too, "I know I'd like to see more of him," she said, nudging my arm with her elbow. Samantha's face kind of dropped a bit after that, knowing that now she had competition she couldn't possibly beat in her mind.

I just ignored it, and kept my attention on Samantha, which seemed to put her at ease a little more. I finished my food shortly after Mike finished his, and we stood up to leave. "Can I walk you back to your room?" I asked the gorgeous brunette I'd just met.

Samantha hesitated for a moment, then smiled at me and agreed. I stood next to her and offered her a hand, which she gladly took as she stood, too. After she was standing next to me, I offered her my arm in a joking, almost exaggerated kind of way, giving her an out if she were to feel uncomfortable with that.

She didn't though, and gladly took my arm as we began the walk back upstairs. Mike walked behind us, and Chelsea and Brittany stayed behind for a few minutes. They lived on the second floor on the other side of the building, so they took a different stairway.

When we got to our rooms, I told Samantha that I was really glad to meet her, and I looked forward to going to the party with her the next evening. She smiled and kissed my cheek before going into her room and closing the door behind her.

Mike and I walked into our room and I followed him over to his side. "Hey, man. What was up with the way you looked at Brittany? Is there some history there or something?"

"Well," he began with a great deal of hesitation, "kind of. At the beginning of the year, I had, shall we say, and embarrassing moment at the pool, and she laughed at me for it. She used to tease me a lot about it, until I finally told her to stop."

"What happened?" I asked, trying to imagine what it was that was so bad.

"I was standing by the side of the pool, trying to put my goggles on, when she came up behind me and pulled my swimsuit down, then pushed me in the pool, naked in front of everyone." He looked really upset about it, and I wondered then what she'd teased him about.

"That wasn't a nice thing of her to do. What did she tease you about though?"

"She laughed at me for having a small ass. She teased me about it constantly for over a week, calling me cutie pants and stuff like that."

"I can see where you could take that personally," I assured him.

"Everyone said she was just flirting with me, but I didn't see it that way. It was humiliating. Everyone saw my dick, plus the water was really cold that day, so everything shrank quite a bit by the time I got out of the pool again, and she still had my swim trunks. She refused to give them back unless I turned around and showed her my 'little ass' again. Then she wanted me to do jumping jacks in front of everyone. I did, and she gave them back, but the damage had been done already."

"That sucks, dude. I can't even imagine what that was like. Did she get in any trouble for it?"

"No. Everyone but me thought it was funny. The worst part is that I used to have a really big crush on her, I couldn't believe she'd treat me that way." Mike looked down at his feet as he sat on the bed. I could tell it still really affected him in a big way. I had the suspicion however, that Brittany really was just flirting with him, albeit she certainly could've come up with a better way to do it.

"So that's why you got so quiet when she sat next to you, it makes sense now." I said, not offering that I was formulating a plan to get them together later.

"Yeah," he said. "I'm going to go for an evening swim. Care to join me?"

"That sounds good, let me find my bathing suit." I walked over to my side of the room and searched through every box and bag I had, but I just couldn't find it. "I think I'm going to have to pass on that tonight, Mike. I can't find my suit. I think it's in the box of clothes that I shipped over here. It still hasn't arrived yet."

"That's okay, the pool is usually empty this time of night anyway, and swimming alone clears my head. I could use it right about now."

"Okay, well enjoy yourself. I should be here when you get back." With that he changed into his suit and headed out the door.

By that time it was almost 9 o'clock and I was unusually tired so I decided to just go to bed. I took off my shoes, then my jeans and shirt, leaving them in a pile on the floor. I then flopped face down into my pillow, and without even covering up, I was out.

* * *

I woke up the next morning to a knock at the door. Mike answered it, and the person said they were looking for me. He told them he'd get me, and I'd be right out. Mike turned the corner into my half of the room, and didn't seem phased at all to see me laying face down, naked on my bed. He told me the administration had sent a student assistant over to come get me, they needed to talk to me about my schedule. I got up, almost forgetting I was nude, before pulling on my jeans, shoes, and shirt. Mike turned back towards the door after I was dressed and opened it again.

"Hi Jason, my name's Matt. I'm an assistant for the staff here, and they'd like to see you in the office. Do you know where it's at?"

"Hi Matt, no I don't. Would you mind showing me?" I asked.

"Sure, no problem!" We walked down the stairs and out the main entrance to the dorm building. We crossed the courtyard over to the main school, and he led me right to the proper office. Sitting inside was the school counselor who told me that due to safety requirements, before they could finalize my schedule I had to take a physical exam, and a swimming test in order to be cleared for all the classes I had to take.

They called up another assistant to escort me to the medical part of the building, this time, it was Chelsea. "Hi Jason!" She beamed. "I get to take you for your physical I guess."

"I guess so, where is it?" I asked.

"It's just down the hall a little ways, but first, you need to go to the locker room and strip down to your underwear. I know it sounds strange at first, but it just makes it quicker and easier for the school doctor."

"Okay, just lead the way!" I said as I followed her down the hallway. She walked me into the locker room and stood there to watch as I undressed. I don't think she needed to watch me, but I got the feeling she wanted to. I was a little nervous because the boxers I was wearing were kind of loose, and my dick had a bad habit of popping out of the front of them whenever it felt like it.

I managed to stay covered though, and she led me a few doors down to the medical room. The nurse guided me in to an area behind a curtain and asked Chelsea to stay outside. She pulled the curtain behind her, then told me to remove my boxers as the doctor would be in shortly. She turned her back to me while I removed them, then asked me to sit on the table and wait there. Once I was seated, I covered myself with my hands and she turned back around. "Okay, you're all set. The doctor will be in in a few minutes." She said, and pulled the curtain back open to leave.

I was glad I was covering myself, because Chelsea was still standing right outside. When the nurse left, she didn't quite close the curtain all the way, so Chelsea had a direct view of me sitting there naked. I pretended like she wasn't there, because at that point, what else could I do? I just had to wait for the doctor to arrive, and hopefully close it behind him.

That didn't happen though, she came in through a different curtain. When I turned around I saw four other girls sitting on a bench across the other room, and the doctor didn't even try to close that curtain. Great, here I was, going to be on full display for not only Chelsea, but four other girls, too.

The doctor asked me to turn to my right so she could get my measurements and to put my hands by my side and keep them there. This gave all five girls a direct view of my penis from the side. Chelsea on one side, and the other girls on the other. Oh, not to mention the doctor didn't appear to be older than mid twenties, so by the time I dropped my hands, I was red with embarrassment. She went through her checklist and did the normal routine, blood pressure, checking my breathing, so on and so forth. Then the hernia check came. She put on a glove and squeezed one of my balls between her fingers. "Turn your head and cough, please." I did, and accidentally made direct eye contact with one of the girls on the bench in the other room. They all giggled when they saw how embarrassed I was. With that part finally over, the doctor had a surprise for me. A prostate check. Yeah! A prostate check at 18 years old! I couldn't even begin to imagine what for, but when I asked, all she would tell me is that "it's normal procedure for males here at this school to receive one as part of a 'sexual health' checkup.

I had no choice. She had me go to the other end of the table and bend over, my ass pointed directly at the four girls on the bench. I looked up and saw Chelsea beyond the other curtain, and now standing next to her was Brittany! This had just gone from bad to worse, and it wasn't over yet.

The doctor gave me a plastic cup, and told me to hold it below my genitals to catch my release. My release!? This wasn't an exam, it was a full blown prostate stimulation, to completion! I'd heard this was a thing, but I never imagined I'd have to have it done to me at a doctor's office, much less in front of all these female classmates!

It got even worse from there, it turns out the four girls on the bench were not only there for their physicals, but as a learning experience as well! The doctor called all four of them back into my room while I'm bent over this table. She begins by asking them if they all have a clear view of everything, then she puts on her gloves, and lubes up her index finger. She tells me to relax, and that I might feel some discomfort at first, but it's all normal. She slides her finger in my asshole and starts to move it around, searching for my prostate gland. She finds it and makes a note on her chart. She then pulls her finger out and I hope it's over. It's not. Now it's the first girls turn, she gloves up and does the same as the doctor did, with her direction of course. Then the other three take their turns at it, meanwhile also having a very good look at my bits from behind.

I think it's about over when the doctor says "now I'm going to demonstrate the prostate milking technique. Pay attention, especially to the patients genitals. When done properly, this creates a very powerful orgasm, and a very productive ejaculation." She puts her finger back inside of me and starts massaging my prostate. I get hard within seconds, and I know Brittany and Chelsea can see it quite well from their vantage point since they've moved much closer without me noticing.

This goes on for a few minutes and I can feel the precum dripping from my engorged dick. I was surprised at just how good this was actually feeling, and even though I should've been embarrassed beyond belief, the fact that I had six attractive girls watching everything just made it that much better. Not to mention, the four from the bench were in their underwear, too, although I couldn't see them very well at this point. My mind wandered back to the day before in the shower with Brittany, and the image of her standing there naked, plus the image of her bare ass bouncing away from me pushed me over the edge. I let out an involuntary grunt and moan, then came full force into that little plastic cup I was holding between my legs.

My knees buckled and two of the girls each put a hand on my hips to steady me, thought they were more accurately grabbing my naked ass. I just kept cumming and cumming, I had no idea an orgasm could last that long, it was actually really amazing. Before I knew it I was spent, and every last drop I had in me was now filling up this little cup. The doctor took it from me and sealed the lid on tight. "Okay Mr. Quinn, you're all set. You probably will want to lay back on the bed and recover for a few minutes though, an experience like that can really take it out of you."

She wasn't joking, it really did. At this point I didn't care about my audience, I just laid back on the table and tried to catch my breath. All four girls at this point had gathered around the table, and were all looking at my slowly fading erection. Once it subsided, it flopped forward and landed on my balls, causing all the girls to laugh, including Brittany and Chelsea, who had pulled the curtain open even further and were basically standing in the same room!

After a few minutes, the doctor came back, leaving the curtain open even wider so that I could see even more female students in the room with the bench, and they could see me. She told the original four to take their seats again, once more the curtain remained open. She then told me to get up and put my underwear back on, I was done and I had passed. At that point, I was beyond caring about all the people watching me, it was supposed to be a professional environment, and whether it was or not, I was going to pretend it had been, just to save what little was left of my dignity.

She called for Chelsea to then escort me to the pool for the swimming test, but first to let me get the rest of the way dressed. She stood in the locker room with me again as I put all my other clothes back on, smiling at me because of the scene she'd just witnessed.

When we arrived at the pool, I met the swimming instructor, Ms. Clark, another young woman in her twenties who seemed much nicer than the doctor was. She told me to go behind a curtain in the corner and change into my swim suit. When I informed her that I didn't have one, that I was waiting on my delivery to arrive with my other clothes, she told me that it couldn't wait, as we had to get this done today.

She then told me to just strip to my boxers and swim in those. Sitting in the bleachers of the pool were around thirty students, all in their swim suits, awaiting their turn in the water. About ten of the students were male, the rest were females. A few snickers could be heard as I stepped out from behind the curtain, once again in just my boxers.

I grew up swimming in different pools, and was actually a really good swimmer so I wasn't too worried about this test. I was worried about my attire however, and as it turned out, for good reason. As soon as I dove in the water and started towards the other end of the pool, I felt the elastic waistband of my underwear begin to slide further and further down my lower body, eventually the kicking of my legs caused them to fall off from around my ankles. Now I was naked in the pool, being watched by all these people. Once I finished the first lap and turned around, I began searching for my lost pair of boxers. I heard Ms. Clark blow her whistle and yell at me to stop. I looked up, and there was my underwear. In Ms. Clark's hand. I stayed in the pool, treading water to keep afloat hoping the instructor would toss them back to me. She didn't.

"Mr. Quinn. I was afraid this would happen. Get out of the pool and stand up here, facing the bleachers." She couldn't be serious, could she? She wanted me to stand completely naked in front of all those people? Not wanting to disappoint her further, I complied with her instructions and climbed out, covering myself with my hand as soon as I got my feet on dry ground. "Hands on your head, Mr. Quinn!" She barked, anger in her eyes.

"Are you familiar with the rules here at Stephens?" She asked.

"No, Ma'am. I just arrived yesterday and haven't had the chance to read the rule book yet."

"Well, let me bring you up to speed on the rules of the pool. Anytime a student looses their suit in the pool, it's an automatic five day punishment."

I wondered just what that punishment would be, as if standing in front of thirty plus of my peers wasn't bad enough.