School at St. Agobard Island Ch. 03

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Jack spends the night in Rose's dorm.
3.2k words
4.39
7.6k
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Part 3 of the 3 part series

Updated 06/09/2023
Created 04/17/2020
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Carible
Carible
77 Followers

I woke up to sunlight the sound of soft footsteps around the room. Before I opened my eyes, I took a moment to remember where I was and why I was in a bathrobe. Yesterday, I got my clothes stolen, and Paz let me sleep in her house. This was her robe. Being naked around her had made me so horny that I dreamt she gave me a handjob, I guess. It was a very vivid dream.

I opened my eyes. Paz was walking into her room with a basket of clean laundry. She was fully dressed. I looked at the clock. 8:30. I sat up and noticed the morning wood creating an obvious tent in my robe. I guess that's what I get for dreaming about Paz jerking me off.

She exited her bedroom and noticed that I was awake. "Good morning, Jack."

"Good morning," I said meekly.

"Good news. I visited my father, and I brought back some of his old clothes that I thought would fit you. You can put on an outfit whenever you're awake. The clothes are in my bedroom. And you can keep the outfit too."

"Oh, thank you." I started getting up slowly, with my arm covering my morning wood. When Paz walked off to the kitchen I went into her room and closed the door.

Looking around, I saw a computer, a dresser, a filing cabinet. Pretty much what I would've imagine a teacher's bedroom to look like. Except when I turned around I noticed a poster of what looked like some kind of heartthrob singer. That would belong better in a teenage girl's bedroom.

I ignored it and look through the basket of clothes. There were cargo shorts, dress pants, a vest. Kind of a weird assortment. I found a pair of jeans and a flannel shirt. I put those on. There was underwear in the basket too but I didn't wanna wear someone's old tighty whiteys.

It was all slightly small on me but as someone who had worn a lot of hand-me-downs, it was nothing I couldn't handle. When I left the bedroom, Paz was making breakfast. She stopped when she heard the door open and walked over to me.

"Oh, that outfit works nicely," she said. "... Jack, could we sit down to talk for a moment?"

"Um, sure," I said, as we each took a seat at her kitchen table.

Paz looked serious. "What happened last night... It was a very serious mistake, Jack."

"Last night?" I asked.

"Yes. The... the somewhat sexual encounter that occurred," said Paz. I guess that wasn't a dream. "It was something that... I don't know what came over me in the moment, but we could both get into serious trouble for this. Well, mostly me."

"Oh," I said.

"It seems sick to ask you to keep it a secret, but I am afraid that if somebody found out, I could lose my job. It is only my second year as a professor. I just want to say that I am so sorry to have put you in that position, and to put you in this position now. It was very unprofessional of me and wrong." Paz sounded sincere and scared.

"No, I... understand. I won't tell anyone. I wouldn't have anyway."

Paz nodded solemnly. "I still haven't gotten word on a replacement key."

"I'll go back to the dorms and see if my friend will let me in again," I said.

"Alright," said Paz. "My doors are always open if you're out of luck."

I eventually had breakfast and started the trek back to the Academy. I couldn't believe Paz Whitman actually gave me a handjob. The more I thought about it, the more I thought it would be awesome if other people knew about this. But I wasn't fixing to say a word.

I got back to the school and I hung around for a while in the chairs in different lobbies. I didn't want to go to Rose's room because I felt like it would just be awkward to ask to sleep there and then leave and come back later. So I got lunch, and hung around more. When I eventually had to pee, I went into the bathroom with all my clothes on, disregarding the rules.

I grabbed some pamphlets from somewhere and read them all. They were boring. It was probably six o'clock when the boredom was getting hard to bear.

I caved and knocked on Rose's door, and to my delight, she answered.

"Hi, Jack!" she said. "What's up?"

"Hey," I said. "Uh, gee, it's a really weird situation I'm in and I need your help. Can I explain in private?"

She let me in and I started to explain as a blush fell over my face. Sitting with her on her bed, I told her everything except for Paz being topless, my erect dick being pressed against her back, and her giving me a handjob. She looked shocked the whole time anyway. I noticed on her alarm clock that it was only two o'clock, not six.

"Damn. This Whitman lady sounds so nice," said Rose.

"Uh, yeah. She is."

"But you never explained what happened to your clothes in the bathroom."

"Oh, I don't really know," I said. "But I think this guy Archie stole them. Do you know him?"

"No, what's he look like?"

"Preppy, skinny, curly blond hair."

Rose said, "You're describing half of the people here." I laughed.

"Well, I'll point him out to you if all three of us are ever in the same place," I said.

"He sounds like a horrible person. Now I'm scared to ever go in the bathroom again. Thanks a lot, jerk." I chuckled. Rose smiled and put her hand on my knee. "But I'd be happy to let you stay in my room until you get your new key."

"Thank you so much, Rose. It means a lot."

"Just make sure you're out of the room when I'm changing. We're not all as comfortable as you are running around the school in the buff." I buried my face in my hands. "You're pretty fucking unlucky. How many strangers have seen you naked since you got to this island?"

"I don't like to think about it."

"... Hey, so, we're in the same chem class, right? Wanna do the problem set together?" she asked.

So we worked on the homework and sort of flirted, I guess you could say. We took our time with it. Eventually we went and got dinner from the dining hall. I met some other friend Rose had made. I forget his name already. I noticed Archie on the other side of the room but I didn't feel like pointing him out to Rose as I had promised.

When all was said and done, Rose brushed her teeth and we were back in her room and I thanked her again for letting me stay there. I still wasn't sure where I was gonna be sleeping though.

"I really owe you one," I said. "So if you ever need anything, just say the word."

"Oh good. I could use some help right now," said Rose.

"Right now? ... With what?"

"My back is just killing me. Do you do massages?"

"Sure, I can try..." I said.

"Great!" said Rose, as she plopped face-down onto her bed. "You can start with the shoulders."

I went to the side of her bed and hesitated for a few seconds before I put my hands on her shoulders and started to press in different directions. I didn't really know what I was doing. "How's that?" I asked.

"Could use more pressure."

I pressed harder, but I was afraid of hurting her. I guess massages are supposed to be a little rough. I could feel the shape of her bra straps through her shirt. I pressed my thumbs into the exposed flesh at the base of her neck and she went, "Mmm, that's good. You know what?" Rose reached her arms down her body and then pulled her shirt over her head, with only a little bit of difficulty.

I kept rubbing her shoulders as I looked all over her back. It was smooth but with many contours. Shoulder blades, spine. She had some freckles on her back. "Could you get the middle parts of my shoulders?"

I rubbed with my hands centered over her white bra straps. "Like here?" I asked.

"Yeah. I know the problem," Rose said, and she reached behind her back to unhook the bra. She shimmied the straps off her shoulders and onto her arms.

There was a lot of skin from her neck to her lower back. I kept massaging her shoulders and Rose seemed much more relaxed than me. She said, "Could you get the lower part too?"

I gladly moved my hands to her lower back and started massaging with a hand on either side of her waist. My dick was starting to stir. I pressed my crotch against the side of the bed to keep it down but it only helped my excitement.

I felt that I was being seduced, which was something new for me. Girls had liked me before, but had never made it so easy. I contemplated what to do next. How do I make a move without being presumptuous? I continued to massage as I tried to come up with a plan.

"That's enough. Thanks, Jack," said Rose, happily, as she hooked her bra back up.

"That's... all you need?" I asked.

Rose sat up and put her shirt back on. "Feel a lot better now. Thanks so much. You have magic hands."

"So you don't want any more than that?"

"... No, why?" asked Rose, looking a little puzzled. She smiled again. "Anyway, I should be getting to bed soon. I don't know when you usually sleep, but..."

"Yeah, now is good," I said.

"Great. The bed isn't really made for two, but-"

"I can sleep on the floor. That's fine," I interrupted, starting to get sick of the unaddressed sexual tension.

"No, no! It's not made for two but we'll fit. It'll be fun to share," insisted Rose. "Just leave the room while I change. Go on."

She shoed me out of the room and I waited in the hall for about a minute, listening to clothes shuffling around inside until she let me back in.

She was in just a tank top and briefs. "Okay, now I'll leave so you can change," she said, headed for the door.

"Uh, Rose? I obviously don't have anything to change into," I said.

"Ohh, you're right, aren't you?" She seemed to be playing dumb. "Well... you can't sleep in jeans and a button-down shirt. I don't mind if you sleep in your underwear. That's what I'm doing, basically."

"Um... I'm not really wearing any underwear."

Rose laughed. "You're just, like, freeballin' it? Why?"

"I had to choose this from someone else's clothes. I didn't wanna wear someone's underwear!" I explained.

"Well..." Rose said, walking over to me. "If you're not embarrassed or anything..." she started to unbutton the shirt I was wearing. "I certainly don't mind you being comfortable." She finished off the buttons and I took my shirt off.

"Do you mind?" she asked, as she put her hand on the fly of my jeans. "Do you want to be comfortable?"

"I mean... Yeah, why not?" I said.

She unbuttoned and unzipped the jeans and pulled them to the floor. "Okay," she said. "I am really tired. I need some sleep so badly." She laid down on her bed and tried to make room for me. I laid down beside her. There was not a lot of room.

"You look like you're gonna fall off," she said. "Well, how 'bout we switch places and you hold on to me so I can't fall off. Sound good?"

I swallowed, saying, "Yeah, sounds good." Rose pushed her arm under my torso and I clumsily crawled over her as she crawled under. My penis was hanging down and definitely brushed across her body. I quickly started to get hard.

She faced away from me and put my arm around her so we were spooning. She shimmied up into me. I let my dick press against her ass since she didn't seem to avoid it. And then we just stayed there.

Rose didn't move or speak or do anything to indicate that she wanted to do anything more than sleep. If she wanted to fuck, she was definitely going about it the wrong way. Involuntarily, my dick kept growing and I assumed she could feel it on her butt.

I subtly caressed her arm with mine to see if she reacted. Nothing. After what felt like an eternity, Rose rolled over so she was facing me. Her eyes were closed, but she put her arms around my torso. Then she lifted her leg and wrapped it around mine, so my erect dick was pressed right against her underwear.

Her body was warm and soft, and it was a struggle to keep still with my arousal. We were face to face but her eyes were still closed.

I opened my mouth and spoke as quietly as possible. "Rose?"

She opened her eyes and looked dead at me. "Yeah?"

"Were you asleep?"

"Nope."

"I don't know how to ask you what I want to ask you," I said.

"Well, just ask. I won't be offended. Unless it's something offensive."

"Some of the things we've been doing... the massage, you taking my clothes off, you, uh, us being in this position... it's sort of... making me turned on?"

Rose looked a bit amused. "Yeah, I can tell."

"I feel like we're in a somewhat sexual position here. Do you... plan on us... doing anything?" I asked.

"Well, Jack, I like you a lot. But I don't think I'm ready to do that with you. I want to know you better first."

"Then why are you doing all of this?" I asked, slightly irritated.

"For fun?" Rose said, frivolously.

"... Okay. I have to go to the bathroom."

"Have fun," said Rose.

I climbed over her, my dick once again brushing across her. Then I put on my jeans and went to the bathroom. I didn't like the feeling that Rose was playing with my arousal for fun. But it was working. So I got to the empty bathroom, masturbated furiously for a few minutes in one of the stalls, cleaned myself up, and came back to the room.

Rose smiled, half asleep. "Look who's back."

I climbed back into bed, leaving my jeans on and facing away from her. "Aw, what's the matter?" she said.

I rolled over to face her. "I don't really wanna be teased, or used for fun."

"Sorry, I wasn't trying to tease you, Jack. I wanted both of us to have fun. Just some fun without having sex. And it's way too hot for jeans."

Unfortunately, she was right about it being too hot. I was sweating up a storm and nobody wants their balls pressed against denim or their dick pressed against a zipper. So I took the jeans off and threw them on the floor.

I guess... why not have "fun," right? So I cuddled up close to Rose, obliging to her idea after all.

Earlier, when I was trying to figure out whether Rose wanted to have sex with me, it was impossible to sleep. But now, knowing that we were just sleeping, I actually found it quite comfortable being naked with our sweaty bodies pressed against each other. It wasn't long before I was asleep.

--------

I woke up with my arms wrapped around Rose and my morning wood pressed against her ass cheek. It felt good, but it made me horny. Her hair smelled kind of sweaty. My cock wanted relief. I pressed myself closer to her. It was weird being totally naked in bed with a girl and not having any shot at sex.

I involuntarily wriggled a bit, causing the bed to squeak. I think this woke Rose up. She slowly rolled over to face me, smiled, and said, "Morning, sleepy head."

"Good morning," I said. She gave me a peck on the cheek as if she'd done that before and then sat up. She looked at my erection and then gave it a tap with her fingers to watch it bob around like a bobblehead. She smiled to herself. She went off to the bathroom and I started jerking off.

It became clear how much pent-up arousal I had from last night. The door suddenly opened back up and I let go of my dick. Rose entered the room laughing and closed the door behind her. "What are you doing there?" she said. I closed my eyes. I didn't know what to say.

Rose said, "I saw there's some clothes in the common room. Just, like, sitting on a table. They couldn't be yours, could they?"

"Can you bring them in here?" I asked.

"Well I don't want to touch them if they're not yours. Come take a look."

I got up without putting anything on, thinking my confidence might impress her. I peeked down the hallway and saw my outfit from two days ago lying on a table.

I smiled at Rose. "Yeah, that's mine."

"Well go get it!" Rose grabbed me by the butt and pushed me out into the hallway. I had been through so much embarrassment at that point, that I didn't really mind running to the common room naked to grab my clothes.

I ran back to Rose's door, which she had closed behind me. Oh lord, Rose. I knocked and started hurriedly pulling the clothes on. I was in the girls' half of the dorms and aware that at any moment a girl could walk out of her room, toothbrush in hand, and see me naked. I knocked again and kept getting dressed.

Rose finally opened the door when I was fully dressed. "That's not funny," I said, walking into her room. "Anyone could have seen me."

"Your keys in there?" Rose asked.

I checked my pockets. Keys. Phone. I smiled. "Yeah."

"Then what are you still doing here?"

"Thanks for letting me stay here," I said. "You might be the best person on this island."

She smiled and shifted her weight cutely. "Yeah, I know."

I stepped closer to her and naturally our hands raised up to hold each other. I pulled in close and kissed Rose on the lips. She kissed back and it felt like magic. I couldn't pull away for a long time because it was too nice.

Eventually the kiss ended and we stared into each other's eyes.

"... See you around then," I said.

"Yeah, um, seeya."

I walked back to my room, unlocked it, and went in. It felt so good to shut my own door behind me.

You'd think I was tired of being naked by now, but my clothes actually felt quite uncomfortable. I stripped naked and masturbated thinking of Rose.

I really liked Rose. She was pretty and sweet, but it was more than that. All I knew for sure is that I wanted to see more of her.

Carible
Carible
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BizarroMeBizarroMealmost 3 years ago

Please don’t give up Carible. There’s more story to tell, right?

AnonymousAnonymousover 3 years ago
Excellent stories

When will you be writing the next chapter?

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