Chapter one : College Brings New Experiences
I earned my Masters Degree in the first semester of my colligate life. Okay I can sense that most of you are rolling your eyes and saying something like, ‘My oh my, doesn’t he have a high opinion of his intellect.’ Well let me try to explain that a little better. I am using the term ‘Masters Degree’ in a little different way than perhaps you are thinking. Okay, now I probably have you all confused, so let me just stop here and tell you my story from the beginning.
I turned eighteen two months after I graduated high school and just a month before I headed off to college. This would be the first time that I would really be away from home for more then a week or two on my own. Suffice it to say, I wasn’t a very experienced person in any of the ways of life. I was excited about getting out into the world, into a big city, and to start to finally experience all the things I had either read about or heard stories about from others.
The college I choose, well they choose me really, I had received a full two year scholarship, encouraged the incoming freshmen to arrive three weeks early so that they could tour the facilities and get to know the city and the way things worked. I was more than happy to get out of my little home town and get on with this next stage of my life.
I arrived at the dorms midmorning on Monday and quickly learned I would be in a dorm room on the third floor. I would be sharing the room with two other young men, one was another freshman who would be arriving the same day, and the other one who was a Junior, wouldn’t be arriving until a day or two before classes started. The lady at the dorm offices led me up the stairwell to the third floor and walked me to my room. After letting me in she handed me the door key and told me to get settled in and she would return later with the appropriate maps and papers that coincided with my class schedule. I thanked her and she left, closing the door behind her.
The room was small, but spacious enough for three people. There was a bed along the right wall, another along the left wall and the third bed was along the far wall between the other two. There was a small desk at the head of each bed and a dresser at the foot of each bed. In one corner was a small kitchenette and then there was a small sofa and three comfortable looking chairs and a couple of tables in the center of the room. I looked over the beds and opted for the one on the right. It was closest to a window and since the center bed was already made up and tagged, I figured the junior had reserved that one from the previous year. I dropped my bags on the desk by the bed. I noticed the package of linens and towels on the bed. Oh great I thought, I guess I have to make my own bed from now on, moms not gonna be here to do that anymore. I neatly made the bed and sat down on it and looked around the room. I got up and opened the only other door in the room except for the door I had entered. It was the bathroom. It was rather spacious. A large tub, plus a separate shower stall. It had a double sink and a toilet off in the corner behind a half wall. There were three small cabinets on the wall, each with its own key still in the keyhole. I choose the first one and opened it, to my surprise it was filled with all the toiletries one would need. I closed the door and turned the key and removed it and slipped it into my pocket. I took a quick piss and went back out into the main room.
I started to unpack my bags and was putting things into the dresser when there was a knock on the door. “Come in.” I called out. It was the same nice lady that led me to the room.
“Toby,” She began as she motioned to the young man beside her. “This is Jake; he will be your roommate this year along with Benjamin. Jake here is a freshman just like you; while Benjamin is a junior who you will meet I’m guessing in a couple weeks.”
“Hi Jake, nice to meet you.” I said as I walked across the room, hand extended.
“Same here Toby.” He replied.
“Well I’ll let you guys get acquainted and settled in,” She said as she turned to leave. “Any problems or questions just come downstairs and see me. Good luck guys.”
“Thanks, have a nice day.” I replied as she walked out and closed the door.
“So where are you from?” Jake asked me.
“Medford Minnesota,” I answered. “I’m sure you’ve never heard of it, it’s a small town in the middle of the state. So how about you?”
“I’m from Houston Texas,” he replied, then added jokingly. “Ever hear of it?”
“Yeah, I think I have.” I laughed. “So, uh, well I don’t know what else to say, not use to meeting new people yet.”
“Yeah me neither,” Jake said as he dropped his bags on the bed against the far wall. “So when did you get here?”
“About an hour ago I guess.”
“So what are your plans for today?”
“I thought I would check out the buildings on the quad and see if I can follow these maps they gave me.”
“Cool,” Jake answered. “I think I’ll just stay here and chill out for the day and start out checking things out tomorrow.” He turned to his bags and began unpacking and then added politely. “Unless you want company on your walk around?”
“Thanks for asking, but I think I’d rather check it out alone today, see if I get lost or not.” I laughed. I pulled out my cell phone. “Let’s exchange numbers in case I change my mind.”
“Or you get lost?” Jake laughed.
“Yeah,” I answered jokingly. “Plus as roommates we should probably have each others number anyway.”
We exchanged numbers and he went back to unpacking.
“So I’m gonna hit the shower before I leave, you need to use the bathroom before I go in?”
“Oh yeah,” Jake said. “The joy of a shared bathroom, thanks for asking, I actually do by the way.” Jake went into the bathroom and closed the door.
I don’t really remember why I did this, but I did. While Jake was in the bathroom I set my camera up on my dresser and looked through the viewfinder and moved it around until it was viewing most of the room. I plugged it into my computer and pressed the record button and took off my shirt and laid it across the camera covering the red light that indicated it was recording. I didn’t set it up for security really, I didn’t think Jake looked like he would go through my stuff or steal anything, I guess I was just curious what college dorm room life would be like and this might give me a small view into that life. I was sitting on my bed with a towel over my right shoulder when Jake exited the bathroom. I stood up, my clean clothes in my hand and walked towards the bathroom past him, I thought I caught his eyes staring at my abdomen when I did, but I just shrugged it off as being in close quarters and one had to look somewhere, and I was looking at him after all.
I showered and redressed in the bathroom and walked out. I dropped my pants, socks and underwear into the laundry hamper as I went back to my bed and sat down and put on clean socks before slipping on my shoes.
“Well see you in a couple of hours I guess.” I said as I headed for the door.
“Yeah, see you later,” Jake replied and then laughed. “Call me if you get lost.”
I laughed and left the room and headed downstairs and outside. I stood in front of the dorm building for a couple of minutes just drinking in the views of the campus before I headed off on my journey. As I walked down the sidewalk, I had the weird feeling someone was watching me.
I returned to my dorm room after about three hours of wandering the campus. When I got back I found a note on my desk from Jake saying he was bored so he decided to take a walk around the campus too. The note went on to say that he hoped he’d run into me on my journey, but if not he would see me when he returned around six pm. I looked at the clock on the wall, it was four thirty. I had an hour and a half to be alone for the first time. I sat on the sofa and clicked on the TV. After scanning through the channels and not finding anything good, I remembered I had set the camera up, so I decided to see what I had caught on film while I was gone.
I clicked the camera off and unplugged it from my computer and carried the computer back to the sofa and sat down and clicked on ‘View videos’ and then clicked on ‘Recent video’.
I sat and watched as Jake walked from his bed to one of the windows and stood there and looked out for about ten minutes. I got up and looked out the same window; it gave me a clear view of the sidewalk out front. Hmm, I thought, maybe I wasn’t imagining someone was watching me earlier, it was probably Jake. I smiled, being glad that my senses treated me right. I went back to the computer and watched as Jake unpacked his clothes and put them in his dresser. I clicked on fast forward and watched Jake do a speed run around the room doing really nothing, then I stopped the fast forwarding as I saw Jake take off his shirt. I don’t know why I did that, after all I am not gay or anything, but I was curious as to what my roommate looked like, and I figured I’d be seeing him many times in different states of undressed as would he be seeing me the same way. After he removed his shirt I watched him go back to the window and look around. Then he pulled off his pants while standing at the window. I saw he was wearing a tight turquoise blue pair of jockey shorts. They actually looked good on him against his dark brown skin. I couldn’t tell if his skin was that deep of a brown from the Texas sun or if that was his natural skin tone. What followed next both shocked and surprised me, and I must admit, it got me a little excited for some reason.
On the computer screen I watched as Jake walked over to the clothes hamper and opened it and pulled out my red jockeys I had dropped in there after my shower. He held them in his hand and looked around the room before bringing them up to his face and sniffing the crotch. I burst out laughing. I never knew anyone who would want to sniff someone’s sweaty underwear before. I kept watching and was even more shocked to see him start to rub himself through his shorts as he sniffed my shorts. Soon I could see the bulge in his shorts as he kept rubbing himself and sniffing my shorts. After a couple of minutes he pulled his shorts off and revealed his hard cock. It looked small, about five inches or so, it looked smaller than mine and I was just a little over six inches hard. I saw that his skin was the same deep brown under his shorts as everywhere else, so I figured it was a natural skin tone and not just a deep suntan. He stood there naked stroking his hard little cock and still sniffing my dirty underwear. I eyed his body on the screen; he was very slender, but toned. He wasn’t muscular, just well toned, but very slender. It was then that I realized that I had gotten hard myself watching Jake standing there naked jacking off and sniffing my underwear. I thought to myself, well this is new. I had never gotten hard looking at a naked guy before, but maybe it was the fact that he was jacking off sniffing my dirty underwear that had me aroused. I didn’t know why I was excited, I just was.
I kept watching the video of Jake, ignoring my own hard cock as I did. I watched as he kept jacking off and sniffing my shorts. Then he began to lick my dirty shorts, all over the front of the crotch. He turned them inside out and licked the inside of the front of my shorts all the while jacking off. He then sucked the crotch of my dirty underwear into his mouth and it looked like he was chewing on them. After a couple of minutes he pulled my shorts from his mouth, I could see a wet spot on the crotch of them when he did. He lowered them down to his hard cock and stuck his cock into the crotch of my underwear and wrapped them around his cock and began to jack off again. I leaned into the computer and was like, what the fuck dude! He was using my dirty underwear to jack off in. I watched as he stroked his cock faster and faster in my shorts until I watched him cum in my shorts. What he did next almost made me fall off the sofa. He lifted my underwear to his face; I could see his cum all over the inside of the crotch. I watched in horror and awe as he licked his own cum from the crotch of my underwear. He then walked back to the hamper and dropped them in and went back to his bed and grabbed a towel and headed to the bathroom with a handful of clothes. I fast forwarded the film until he emerged fully dressed from the bathroom. I watched as he looked around the room and then left. I shut off the film and leaned back on the sofa. What the hell was that all about, I asked myself? And then glancing down at the bulge in my pants, I asked myself, what the hell is up with you?
I sat there for awhile, wondering what I should do about what I had just watched. I also wondered what I should do, or think for that matter, about the bulge in my own pants. I knew I wasn’t gay, I had a girlfriend back in Medford, and we have had sex many, many times. Yeah, like almost all boys, I had jacked off another boy at summer camp, and played the little games like who can cum first or the farthest or the most. But I had never become sexually aroused just from watching a naked guy jack off. I stood up and shook my arms at my sides and shook my head and asked myself, what the fuck?
I thought about going downstairs and seeing if I could change rooms, but decided not too. I don’t know if it was that I didn’t want to cause trouble for Jake or appear to be difficult on my first day, or if my thought process was being determined by the bulge in my pants. In any way, I decided to do something I never thought I would do. I backed up the film to a few spots and stopped it and printed off the images on the screen. I then typed out a note, again very surprised I was doing this; it was as if my fingers now had a mind of their own and they were typing out the note without me being able to stop them. I looked into my desk and found a stack of envelopes and picked one big enough to put the photos in unfolded, along with the note.
I simply wrote across the envelope, ‘Jake, thought you might find these interesting, I know I did!!’
I looked at the clock on the wall, it was quarter of six. I went and sat by the window and watched out for Jake to come up the sidewalk. In about five minutes I saw him approaching the dorm building. I quickly went out into the hallway and went down around the corner away from the stairs and waited for Jake to come up and enter our room. Once he was in the room I sneaked back down and waited outside with my ear to the door listening, while keeping an eye out in the hallway in case anyone else would come up the stairs. After about ten minutes I heard Jake half cry out.
“Oh god no!”
I figured Jake had opened the envelope and seen the pictures I took from the film. I decided to wait a few more minutes to give him the chance to read the notes.
Chapter Two : A Friendship Blossoms
Jake had come back to the dorm room to find Toby gone. After taking a piss, he checked out the room again and then saw the envelope on his bed. After reading what was written on the envelope, he began to open it, figuring Toby had found some cool stuff on his journey around the campus; boy was he about to be surprised.
Jake screamed out when he saw the first of the five photos in the envelope. He quickly looked around to try and see a camera, he couldn’t. He then saw the note and picked it up and read it:
Dear roommate Jake,
Hi Jake, I guess you saw the pictures, I apologize in advance for filming you, but I was just wanting to get a film history of my first day at college, I never expected anything like this to happen. I am amazed at myself that I actually printed them out and left this for you. I am even more amazed at myself for what I am about to write. I saw you were really into my underwear, did they smell good? I had worn them since yesterday when I tossed them in the hamper. I would ask if you enjoyed them, but from what I watched you do on the film, I guess I needn’t ask that question do I?
Although I found your actions strange and unusual, I somewhat understand them I guess. But you did violate my privacy and my property and I can’t believe I am saying this, but you must be punished for that. Don’t you?
So here’s the deal, either I can take a copy of this film to the dorm leader downstairs and /or post it around campus or you can let me punish you myself. And so you know, that would mean you doing whatever I tell you to do for your punishment when I come back here tonight. Now I don’t know if you are gay or not, it doesn’t matter to me one way or the other. I am not gay, but I have to admit that I got excited seeing you naked and jacking off while sniffing my dirty shorts. So here’s the deal, I am most likely standing outside our door as you’re reading this, so right now I want you to call out my name.
“Toby?” I heard a crackling voice ask.
“Yes Jake I’m here,” I replied. “Finish reading the letter please.”
“Ok.” I heard Jake respond and then he went back to reading. In about five more minutes I heard him speak again. “I agree to your terms Toby, and I’m ready to be punished.”
My hand was shaking as I nervously reached for the doorknob. I almost turned and ran away, that’s what my head was yelling for me to do, but again, the bulge in my pants was urging me to open the door and step in. So in I went.
I nervously entered the room. Jake was as I had asked him to be in the note. He was standing in front of the sofa wearing just my dirty red jockeys that he had sniffed, sucked on, and jacked off in just a few hours ago. I could see his cock was once again hard from the bulge in front of the shorts.
“Wow, I didn’t think you’d actually do this,” I stammered as I eyed up his body. He looked cuter in person then he had on the film. He was really slender and he didn’t have any noticeable hair on his dark skinned body, not even on his legs. “I don’t know what to do now.”
“Well I am ready to be punished for doing what I did,” Jake spoke softly and hung his head a little. “I’m sorry for doing that, I just got kind of excited when I saw you without your shirt.”
“Are you gay?” I asked him.
“I don’t know, maybe?” he replied. “I know I like certain guys.”
“Guys like me?”
“Yeah,” he blushed. “I guess, sort of, I did think you were cute when we met and then when I saw you without your shirt, I just felt something I guess.”
“I see you’re excited again.” I said nodding towards his bulge.
“Yes I am,” He looked down and then looked at me. “So can I ask if you’re still excited?”
“Actually, yes I am,” I blushed. “I don’t really understand why, I’ve never gotten excited over a guy before.”
“I’ll take that as a compliment.” Jake half laughed.
“So what do I do now?” I asked as I walked around him. “Can I slap your ass?”
“If that is to be part of my punishment,” He replied. “I guess you can do whatever you feel like doing to punish me.”
“Cool.” I said as I walked up behind him and slapped his ass softly. He smiled. I slapped his ass again a little harder. He smiled more and I saw his cock twitch. I slapped his ass harder and a few times in a row. “That feels good.” I laughed.
“Yes it does.” He laughed back.
“So,” I said elongating the word for a couple of seconds. “I think you’ve abused my underwear long enough for one day. Take them off.”
I watched as he pulled them down and he bent over and stepped out of them. I saw his hard cock bounce up and down a couple of times.
“Put them back in the hamper.” I instructed him. “And don’t ever touch my underwear again, at least not without permission.” I laughed. I walked around his naked body. His hard cock was skinny just like he was, and it looked not much over five inches long. “How long are you?”
“Five and a half inches,” He blushed “I know I ain’t very big. So can I ask how long you are?”
“I’m thinking you’ll find out soon enough.”
Jake smiled and his cock bounced up and down.
I started unbuttoning my shirt.
“So you liked what you saw when I had my shirt off?”
“Yes, yes I did.” Jake answered as he stared wide eyed at me taking off my shirt.
“Well now you can get a closer look,” I said as I removed my shirt and tossed it to my bed. “Do you want my pants off?”
“Yes, please,” Jake said in a begging whine.
“Well then come take them off for me.”
Jake stepped closer and reached out and undid the snap on my jeans and with a shaking hand unzipped them. He gently pulled them down until he was knelling in front of me, his face at my groin. I lifted my right foot and he slipped the pant leg off. I lifted my left foot and he slipped my jeans off completely. He stayed kneeling in front of me waiting for me to say something, all the while staring deeply at the bulge in my shorts.
“So how long do you think it is?”
“Oh, however long it is it looks perfect through your shorts.” He moaned.
“So since you like licking my underwear, you should start licking this pair while I am wearing them.”
“Yes Toby.” He answered and leaned in; I felt his tongue lick me through my underwear. I watched as he licked up and down my cock through my underwear. I spread my legs a little and he licked down and over my balls and then back up to my cock.
“Do you like the taste of this pair?” I asked him.
“Very much so Toby,” he looked up and answered. “They taste better because you’re still wearing them.”
“So how long do you think it is?” I asked. “Measure it with your tongue.”
Jake put his tongue on the base of my cock through my underwear and licked it up to the tip, and then back down. He did this a couple of times and then looked up at me.
“Well it’s a little bigger than mine,” He said. “I’d say about six and a half inches.”
“That’s a great guess,” I laughed. “Pretty much spot on, your tongue is a good measuring tool.”
“Thanks,” Jake replied and went back to licking my cock through my underwear. As he licked I slipped my thumbs under the waistband of my underwear and pulled them out and down in the front, releasing my hard cock. It bounced a couple of times before coming to a rest jutting straight out and pointing at Jake’s face. He looked up at me as he licked the tip of my cock. I smiled down at him and he sucked my hard cock into his mouth and began sucking. I pulled my underwear down off my ass and he reached up and pulled them down to my ankles and I stepped out of them all the while he kept sucking on my cock and looking up at me. I grabbed his hair and held his head in my hands and began to thrust my hips. I was fucking his mouth with my cock. He was caressing my legs and soon was gripping my ass in his hands as I fucked his mouth. I felt I was on the verge of cumming so I pulled back, freeing my hard cock from his sucking mouth. He looked up at me and smiled and licked his lips.
“Not so fast my little cock sucker.” I laughed, as did he.
“Stand up.” I told him. When he stood up I eyed his body up and down. I walked around him and touched his tight small ass. It was smooth and felt of silk. I ran my hands around to his stomach and up his chest and down his sides, all the way down his legs and back up to his ass. I walked in front of him and looked over his nakedness. I reached out and closed my hand around his cock and stroke it a couple of times. “Feels nice, it seems to fit perfectly in my hand.” He laughed.
“I wish it was a little bigger, like yours.” He said as I stroked his hard little cock.
“No, this is a nice size,” I said. “And I ain’t that much bigger.” I let go of his cock and stepped closer so that our cocks were touching side by side. The tip of my cock was touching his belly just above his cock and his was about an inch shy of touching me. I stepped back and saw my cock had left a little wet spot of my pre cum on his tummy. I reached down and wiped it up with my finger. He reached out and grabbed my hand and lifted it to his mouth and licked it off,
“Tasty.” He laughed.
“I’ve never done this,” I said as I knelt down in front of him. “So let me know if I am doing it wrong.” With that I opened my mouth and took his hard cock between my lips and sucked on the head. I worked my way down the shaft until his entire cock was in my mouth. I did what I saw him doing, sliding my lips up and down the shaft of his hard cock. When it was fully in my mouth I bit down gently at the base of his cock. I pulled back and let his cock fall out of my mouth. I stood back up, our cocks were touching again. “How’d I do?”
“Just like a pro.” He laughed as he reached down and gripped both of our hard cocks in his hand and began to stroke us both at the same time. The feel of his hand stroking my cock, at the same time my cock was rubbing against his was wonderful.
“I don’t think this is much of a punishment for you, is it?” I asked.
“No not really.” He answered.
“Maybe we can postpone your punishment to another time?”
“Okay, if you want to.” He smiled.
I led us over to his bed, his hand still stroking both of our cocks. I lay down and he lay opposite of me, we started sucking each others hard cocks. I had never sucked a guy off before, but was really enjoying this. I wondered what it was going to feel like when he came, but I sucked harder and faster. I felt his cock tighten in my mouth and throb, I saw his balls pull up into his groin and I knew I was about to taste my first load of cum. Jake shuddered and sucked me harder as his cock exploded his cum into my mouth. Surprisingly, I sucked his cock harder and swallowed his cum as it squirted out of his cock. As soon as he stopped cumming, I felt myself about to shot. I was still sucking on his empty cock when I shot my load into his mouth. My cock throbbed and pumped my cum into his mouth and he sucked me in deep and sucked harder on my cock until my orgasm stopped. We both let each others cock fall out of our mouths and just lay there for a few minutes. He was caressing my thighs and balls and I was rubbing his cock.
“Wow, that was amazing.” I sighed.
“Oh my yes.” Jake whispered. “I can’t wait to be punished later.”
“Yeah, I think I will really enjoy that.”
“I wonder,” Jake said as he looked over to the middle bed. “What our room mate looks like?”
“Yeah, and what’s he into?” I laughed. I got up from Jake’s bed, he grabbed my leg and lifted his head and licked the tip of my cock.
“Shall we hit the shower?” he asked.
“Sure.” I replied as I grabbed his hand and lifted him from the bed. I slapped his ass as we walked to the bathroom.
We both laughed.