Winter Break

by Joe

18 Dec 2013 2372 readers Score 8.0 (24 votes) PDF Mobi ePub Txt


Before I start the second part of this story, I'd like to announce the previous two parts were the introductions. Enjoy the story.

The warmth of the sheets were soothing to me, and as I lay in bed, my eyes half open, I wondered what sort of things would be in store during the winter break I was about to have. I thought about all my friends from school and if they would want to go to the movies, hang out, or party while I was gone. If I went with Mr. Phillips, I would be missed by my friends, at least I hoped so. But this was my last year of school at A. Miller High School, and if I didn't take the trip with the man I was so deeply in love with and had fantasized for years about, I wouldn't ever get the chance again.

As I glanced at the empty duffel bag in the corner of my room, and wondered wether I should pack it, or if I shouldn't, a shrill voice came from downstairs, calling my name, cracking in the middle.

"Damien!" It was my mom, and she was still sad that I wouldn't be able to spend christmas with me. "Are you going to go or not? It's already six thirty!"

I kept lying in bed for another five or so minutes, then I pulled the sheets over the bare skin of my whole body. Sleeping nude always made me feel at the top of my game, and the feeling of the different fabrics rubbing against the weapon between my legs was usually the height of my sleep. I swung my feet over the side of my bed, curling my toes at the feel of the carpet, and stood up, arching my back and stretching my legs as if I were a cat.

While walking over to my drawers for clothes, my siberian husky, Trooper, who my mom had gotten me for my latest day of birth, jumped off the bed and nipped at my heels as I walked. I squatted down, the thick 8 inches of meat swaying in between my legs. I set my hand on his forehead and tousled his hair briefly, then stood back up and opened my drawers, pulling out fourteen different pairs of boxer briefs, a few pairs of shorts (jeans and cargo), quite a few pairs of jeans, tank tops, jackets, v-necks, crew necks, my favorite and softest pair of sweatpants, and a silk black jockstrap Mr. Phillips had recently given me.

I slid the jockstrap up my thick calves and muscular thighs, tightly fitting the straps around the meaty globes below my back, and tucking my man meat into the pouch under my six pack. I slid a tight black tank top over my slightly curly brown hair and over my pecs. I held up the dark green sweatpants and pulled them on after I pulled on my tank top.

After packing all of my things, I stumbled into the bathroom for toiletries. I spread toothpaste on my toothbrush and wet the bristles, while also picking up the Old Spice Fiji deodorant and sliding it slowly across my underarms. After scrubbing my pearly white teeth with the spearmint toothpaste I took the hairbrush and brushed out all the knots form my bed-head. During each stroke of the brush, I put each thing I used and put it in the side pockets of the duffel bag. When I finished, I looked in the mirror. I could see why my friends sometimes compared me to Michael Trevino, I had the same complexion, facial features, and hairstyle as him.

After a trip back and forth to downstairs, forgetting the obvious things, like socks, shoes, and my fleece slippers, which were decorated on the front with two big fluffy black mustaches. Once those two were on my feet I proceeded downstairs with my duffel bag and backpack, which I had filled with things like books, pencils, sketchpads, and chargers. At the bottom of the stairs, my mom handed me my beanie, which I slipped over my hair, and grabbed my iPhone, earphones, and my wallet. I was about to take my keys when I remembered the email I had gotten from Mr Phillips. He and I would be driving there in his car.

"Mom, I need a ride to the coffee shop, could you drive me? And Where's dad?" I asked.

"Your father already left for work, you know he leaves for work at six thirty," she replied. "As for the coffee shop, I can give you a ride, and I have something to give you," She took a wad of 100 dollar bills out of her pocket. "Here's two thousand dollars, in case something happens."

"Mom, I can't take this."

"Just be safe, okay?" She begged me.

I nodded as we walked out of the front door. It was cold out, as the hairs on my arms and the back of my neck had told me. I wanted to pulled out the jacket I had packed, but with the butt-warmers in the car and the air conditioning, I figured I would be all set. I let my mom drive, since I didn't want her to get out after she dropped me off.

The drive over to the coffee shop was silent, with soft sobs in between songs from the radio. When we got there, I immediately saw Mr. Phillips in his sweats and his sweater, with a suitcase under his feet.

"There he is," I told my mom as I hopped out. "Thanks for the ride, I love you."

I pulled the duffel bag out of the passenger seat and slid my backpack over my shoulder. I held the duffel bag in my other shoulder and started towards the table where Mr. Phillips was.

He smiled at me when he saw me, showing off his star-white, twinkling, teeth. His smile had always made me want to melt into his arms and body. His lapis lazuli eyes were making me smile, and as I sat down across from him, at the iron table.

"Hey Mr. Phillips."

"We aren't in school, you can call me Tucker if you'd like." Mr. Phillips said.

"I'll keep that in mind." I replied.

"So, I'll run in and get the coffee, what do you want? I'm paying." He asked.

"Whatever you're getting." I responded.

And he went in, and came back out with two gingerbread lattes in minutes.

"Alright, Let's get going. This all your stuff?" He asked, picking up his suitcase.

I picked up my things and nodded. Then I started to follow him to his car, watching his ass as he led. When he opened the trunk to his Jeep Grand Cherokee, I thought about what it would be like to see him naked. My mind stopped at that thought, when I realized I had, just yesterday, and I had forgotten about it. I handed him my duffel bag and thought about opening his office door, and looking directly into his eyes. When he shut the trunk, I thought about my towel falling to my ankles, and how his gaze had changed from my eyes to my tool. I felt myself getting a hard-on, so I quickly got into the passenger seat and shut the door, then sat down, so the impending growth in between my legs would be hidden.

When Mr. Phillips hopped into the driver's seat I set my backpack coolly in the backseat, pretending the raging boner encased in my jockstrap and sweatpants wasn't even there.

"You have any music you want to play? I've got a port." Mr. Phillips asked. I pulled out my iPhone and plugged it into the port. When Mr. Phillips' keys turned in the ignition, the engine started up, Anberlin's cover of "Enjoy The Silence" came on, and Mr. Phillips pulled out of the parking space he was in and started to drive out of the parking lot.

"You've got nice taste in music." Mr. Phillips told me, when the band Sounds Under Radio came on.

"Thanks," I said, then I looked at my foot. "So why did you start bringing students to your cabin at the lake with you?"

"Oh, it's a long story. I brought my boyfriend there sometimes during summers and winters."

"You're gay?" I asked, startled.

"Actually, I'm bisexual, but not in the way where I only date girls and fuck guys." He informed me.

My eyes were wide by now, I wanted to know more about my bisexual gym teacher. I started to think about the signs. I should've known, by the kiss he gave me at my birthday party, or when he was laying on top of me in the miniature gym, or even when he asked me to start extra yoga lessons with him after school. I felt extremely happy. I thought of this morning, when I was pondering if anything in my desire would happen on this trip.

"So, what happened, that doesn't explain anything to me." I told him. He brought his boyfriend down here often, but that didn't explain why he brought his students to the cabin. Maybe he wanted them to experience what it was that his boyfriend was experiencing. Maybe he brought them down so his boyfriend and him could use them for their own purposes, like mind-blowing, hot, sex. Or maybe his boyfri-

"My boyfriend and I broke up about four years ago, when I became interested in somebody else. I realized that I didn't bring anybody down to the cabin anymore, so I started to bring my favorite students down there, every winter break, and I've thought about bringing some down during spring break and summertime, but never really carried those plans out."

Then we were silent for a while, sometimes making small talk, like talking about the climate, and how it was so cold. Until after four hours of small talk, he asked, "Need to stop for the bathroom?"

"Yeah, I gotta take a whiz."

"Alright." He said, as he pulled in to a gas station.

I got out and passed through the door, walked to the corner of the store, into the bathroom, and up to one of the urinals. I pulled down the front of my sweatpants to just below my low hanging balls, the size of eggs, and took hold of my meat, aiming. I looked to my right and left, noticing the lack of privacy barriers. Then I let loose, peeing freely into the urinal, when a second later, Mr. Phillips came in and started to pee in the urinal next to mine.

"Quite a tool you got there, Damien," He said, smirking, as I shook off the last few drops. I took it as an invitation to look at his. It was uncut, around eight and a half inches flaccid, and had the thickness of a beer can. "You gonna stop staring at mine and put it away now? Before you poke somebody's eye out." He chuckled and shook off, tucking it back into his neon blue boxer briefs.

I didn't understand what he meant, then looked down and realized I hadn't pulled my sweatpants up yet. I pulled up after slowly tucking my dick back inside my pants, then walked over to the sink next to Mr. Phillips, slowly lathering up my hands, slowly making a gesture as if I were jerking off my own hand, but with soap instead of lubricant. When I rinsed off, I patted his back.

"Want anything? I'm about to buy myself some jerky and a coke." I asked him.

"I couldn't possibly take your money."

"No, I want to, trust me."

"Alright I'll have some jerky and a coke, too." He said, putting some emphasis on the 'jerk'. I left the bathroom, grabbing two bags of regular beef jerky and two cokes. I smiled to myself, noticing how he made it sound when he said jerky, he put enough emphasis on the 'jerk' to make it sound like a mistake, but it was so obviously there on purpose. After paying, I walked out to Mr. Phillips' car, and got into the passenger seat, next to the driver's seat, which already contained my yoga teacher, who started up the car and got back onto the interstate.

"Where can I put the food?" I asked him.

"The glove compartment's fine." He responded, keeping his eyes on the road.

I opened the glove compartment, which held nothing but a water bottle, and rolled up magazine in the back, and a still packaged condom. I didn't say anything about it, I just set the cokes and beef jerky in.

"It sure is cold." I noticed aloud.

"Yeah, I'll turn on the heaters." Mr. Phillips suggested.

"Thanks."

I watched the trees go by for about an hour or so, and all I could think about was Mr. Phillips' limp dick shaking back and forth like a rag doll. When I got my mind off it and kept staring at the trees that went my, I started to feel sick, so I closed my eyes for a moment.

When I opened my eyes, we had reached the cabin, and Mr. Phillips had brought me inside, and set me on a recliner next to the bed where he was sleeping. It was around one o'clock in the morning, and Mr. Phillips was completely nude, on his stomach, with only a sheet covering from his feet to the back of his thighs. His round, smooth, perfectly tanned ass was peeking out of the sheets. I looked at his face, he was smiling in his sleep. Then, his eyes snapped open and laid directly on me watching him. I jolted awake.

"Sorry, I must've fallen asleep, the heat was probably making me drowsy." I said, looking out the window again.

"It's cool, you were asleep for five hours though," Mr. Phillips told me. "I guess it is getting a bit hot in here, isn't it?" He pulled his sweater over his head to reveal his perfectly sculpted, tanned, pecs and four pack abs. He tossed the shirt in the back.

I was watching him as he did it, resting my head on the headrest, my mouth slightly open. But I kept watching him, even after he tossed his sweater in the back.

"Yeah?" He asked. "What is it?"

I came back to reality. I had spent a few minutes staring at his body and fantasizing about him. Rubbing his chest, sliding my hands slowly down his pecs and abs until I got to his crotch. My dick has started to shuffle in it's prison again, aching to get out and be pleasured. I shifted in my seat again, looking straight ahead.

"You want me to drive when we get to the next town?" I offered.

"Yeah, thanks, that'll be nice of you. After a while though, we should stop at a motel."

So we drove more, until we got to the next town, where I got into the driver's seat and drove. Mr. Phillips went to sleep, and as I watched the road, I couldn't help to make peeks at his pecs and nipples occasionally. After around five more hours, I stopped at a motel, and set my hand on his shoulder, rubbing it slightly. His skin was as smooth as a stone that had endured a thousand waves. It was shaven to a point of no hair at all, and I couldn't help but touch a bit of his chest before waking him up.

"Wake up, sleepyhead." I whispered.

"Are we there?" He asked, drowsily.

"No, just at a motel until tomorrow morning." When we went in, I walked up to counter. "Do you have two rooms for us both?" I began.

"Actually, two rooms won't be necessary, one room will be fine." Mr Phillips told the woman.

"Absolutely, the room you'll have is room 68." She told us, and handed me the keys, since Mr. Phillips was drowsily walking and seemed a bit dazed. He still didn't have a shirt on, either.

As we were walking, he started to trip. I reached out and caught him in my arms. Then I took him by his bicep and pushed it around my shoulder. I imagined how this would look if he wasn't as drowsy. He would be holding me, his muscles all around me, as if nothing else mattered except that he was touching me.

When we got to the room, I pulled off my tank top and put it over the chair near the desk and turned on the lamp. Mr. Phillips was sitting in the recliner in the corner, catching z's. I crept up to him, careful not to wake him, and picked him up, carrying him over to the one queen sized bed, and placing him under the duvet. I tiptoed around the bed and pushed the sheets and the duvet over myself, tightly resting my head on my head on my pillow, with my hand resting next to me.

The next morning, when I opened my eyes, all I could see was skin. Some of it was me, my hands. My blurred vision started to focus, and I realized I was resting my head on Mr. Phillip's chest. I slowly looked up at his face. His eyes were closed, and from what I could feel on his smooth, bare, chest, he was still breathing. I started to push off the bed, but realized his arm was around my back, in a cuddling position. I maneuvered his arm out from on top of me and pushed the sheets out from on top of me, then stood up and stretched my calves and arched my back, while also pulling my arms over my head in an over-the-head stretch. I crept around the bed to his side and placed my hand on his chest.

"Wake up. We should get going, sleepyhead." I murmured.

His eyes opened, along with a dazzling smile and a quick hand through his dark brown, almost black hair.

"G'morning." He whispered.

"Morning," I murmured back. "Get up you lazyass, we gotta go."

He nodded and got out of bed, stretching his calf muscles, arching his back, and flexing his biceps, stretching his arms out as well. After getting up, he walked over to me, grabbing my tank top on the way, and handed it to me.

I breathed in his scent, the scent of vanilla deodorant mixed with hot man musk. I sat down on the bed, handing the room key to Mr. Phillips, who walked into the bathroom, but left the door open.

"Remember to take a piss before you go." He reminded me, then turned around, and started to zip up after he turned, so I could get an extra glance at his big, flopping cock.

"Will do," I told him. After walking into the bathroom, I pulled down my sweatpants below my balls and did my business, looking down at my own oversized dick. "I'll meet you at the car."

I started thinking about yesterday, when I saw Mr. Phillips' large, uncut, man-meat waving around limply in front of my own. I thought about how my hand quivered, how I wanted to reach out and touch it. I thought about his words in my head. 'Quite a tool you got there, Damien.'

I gently shook off the last of my pee and walked out of the door, so wrapped up in thought I didn't pull up my pants, and my dick was hanging out in the open. But before anybody saw, I realized, and pulled up. I looked around the room, Mr. Phillips must've went down to the lobby to turn in the key.

I walked down the steps to the car and hopped into the passenger seat. Mr. Phillips was already seated in the drivers seat, and had the engine started up. I smiled at him, and he smiled back.

"They were giving out cinnamon buns and coffee. Would you like some?" He asked.

I nodded and reached into his crotch, where he was holding two cups of coffee and had two cinnamon rolls on his lap. I took a sip out of my coffee and slowly stuffed the cinnamon roll little by little into my mouth, taking small bites and swallowing every now and then. When I finished my coffee, Mr. Phillips pulled out of the motel parking lot and started onto the highway.

"So, tell me about your ex-boyfriend. I mean, if you want."

"Oh, You mean Ray.." Mr. Phillips' voice cracked in a sob and he frowned. "I lied to you.. he broke up with me. I fell in love with somebody else.. and he was just.. so.. infuriated.." Mr. Phillips started to cry.

I placed my hand on his free hand, the one he had set in between our seats. He turned to me, and smiled gratefully. My thumb slid back and forth across the tan skin on the back of his hand. I smiled back at him, showing him my pearly whites, that matched his.

"I'm so emotionally damaged," He murmured to himself. "I'm never going to be able to get over him."

"The best way to get rid of bad emotions is to talk about them." I told him, and I rubbed his hand with my thumb more slowly.

We talked for hours on end. He told me about his exes. There was Lindsay, Brittany, and there was Ray. He told me, crying and crying, until his tear ducts were empty. He told me about how he wanted a romantic relationship, but he still wanted frequent sex. I didn't want him to feel so alone, so I told him about my exes. I told him about Conrad and Josue, the only two boys I'd gone out with. How they wanted sex all the time, but how I didn't let them have it. I told him about how I wanted a romantic relationship with plenty of sex as well. By the end he was smiling, and it was around midnight.

"Here we are," Mr. Phillips announced. "it's very big, twelve bedrooms, six baths, lots of living space, a game room, a kitchen-bar, and a dock. Plus more, it reaches underground and rises four stories above the ground. So, we'll have a lot of things to do."