My Boys

Fall 2005

I had just started my freshman year of college. I moved away from home, to a different state; a place where I knew no one. Pretty intimidating, I must say.

Luckily, I got matched up with a great roommate. His name was Will. Like me, he was 18 and a freshman, although he was actually an in-state student.

Will was a good looking guy. He wasn't too terribly tall, maybe 5'10". Slender, but filled out and toned; he was very athletic. He had short light brown hair and a 100-watt smile. And on top of his looks, he had a great personality to boot.

Will and I became best friends while living together. We were inseparable most of the time. I had a great fondness for Will. I never had many male friends growing up, so our relationship was new and special to me. And okay, maybe I was a little attracted to him.

I blame him partly for that. Will seemed to lack the modesty gene. He spent a good portion of time in our room simply in his boxers. Like I said, he was an athletic guy, and his body showed for it. He had a good set of pecs with a dusting of hair over them. And while he didn't quite have a sixpack, his stomach was definitely flat and well toned.

The thing that always caught my eye the most though was the constant protrusion from his underwear. Without even being erect, his member always pushed out the fabric of his shorts rather noticeably. Even when he had pants on, when he sat down, everything seemed to bunch up partway down his leg. I spent many a night wondering what laid beyond those clothes.

Ironically, for all his openness with his body, Will was very tightlipped on the subject of sex. Sure, he'd make the off color joke once and awhile, but talking about it seriously always seemed to make him uncomfortable. He even made it seem like the idea of masturbation was disgusting, as if he never did it. I found that very hard to believe.

I for one was a pretty avid masturbator. I had his schedule figured out perfectly so I knew when I'd have enough alone time to rub one out.

On one such occasion, I was lying on my bed, blankets tossed off of me, pants and underwear around my thighs, and going at it. It had been a couple days, and I was aching for release. I was about 10 strokes away from happyland when I heard something at the door.

Now the way our keys worked, you had to insert the key...the lock would beep...then you turned the key...and opened the door. It was a process that took a few seconds. Usually enough for me to gather myself. But for some reason, I swear this time that door just opened automatically for him.

As the door swung open, all I could think to do was heave the covers over myself. As a reflex, I shot up in the bed, pulse racing, breathing hard. Will kinda froze at the door, the beginnings of a smirk forming on his face.

"Did I interrupt something?" he asked, already pretty certain of the answer.

I panicked, "What? Oh...no, I was sleeping...and, uh...the door scared the crap out of me. Hehe, yeah, you almost gave me a heart attack."

Will stayed at the door and kinda looked me up and down, not buying my answer for a second.

"Well I could leave and come back if you wanna finish your...nap," he grinned.

I wasn't gonna give in, "Oh no, it's fine, just come on in."

He shrugged and entered the room, setting down his bag and sitting at his computer. I laid back down, still covered with the blankets, yet underneath I was fully exposed. How to get my pants back up without it looking and sounding like I was pulling my pants back up?

"You know," Will started, back toward me, "it's not healthy to get worked up like that and not release. Can't be comfortable."

He really wasn't gonna let this go. What did he want me to do, throw off the blankets and say "Yes, okay, you caught me! I was jacking off and you interrupted!"

"Haha, very funny," I tried to play it off. "Like I said, you just shocked me out of my nap."

"Oooookay," he said. "I really don't mind if you finish off ya know."

"Hummanahwha," I mumbled. Had I heard him correctly?

"In fact," he continued, rising from his seat and heading to his own bed, "I might just join you."

As he hopped up onto his bed, I'm pretty sure my jaw dropped from mine. My usually shy as hell about sex roommate had not only told me to jack off with him in the room, but now had offered to join me. Maybe I really had been asleep...maybe I still was.

As I continued to stare slackjawed at him, Will paid me no mind and started fumbling with his belt. Our twin beds were up against opposite walls, but were only about 10 feet apart within the dorm room. So I had no problems seeing every detail of what Will was doing.

His belt came undone, followed by the button and zipper of his jeans. And within moments, his pants were down, almost to his ankles. He did however keep his checkered boxers on. His right hand moved to the center of them and grasped the bulge lying beneath, massaging it lightly.

Any minute now, he was sure to stop and say it was all a joke.

"This isn't freaking you out is it?" he asked.

Here it was. His chance to catch me up in the sick joke. I would say I was cool with it and he'd start laughing and calling me a freak. I just wouldn't say anything.

My body was betraying my mind though. I saw Will's gaze travel down to where the blanket covered my groin.

"I see at least part of you is fine with it," he laughed.

I followed his eyes and saw how the blanket did little to hide my now throbbing erection. He had been right before, it wasn't good to come this far without some sort of release.

"Don't worry, I'm right there with you."

I snapped from my stupor and looked back to his bed. Sure enough, the material of his boxers was now tented up, threatening to tear the fabric in two. I finally realized that he was dead serious about this. There's no way he would reveal himself so intimately without following through.

"Okay..." I finally said. "I give up, you caught me dick-handed."

With a sudden burst of confidence, I pushed away my covers and revealed my intense arousal once and for all. I lay there completely exposed, right hand still wrapped firmly around my 7 inch erection.

"Nice..." Will breathed. I almost thought I heard a hint of arousal in his voice.

I moved my hand slowly up and down my shaft a couple times, allowing him a good look. Then I stopped and turned back to him. I wanted him to know I wasn't about to be the only one in this position.

He got the hint. With a slight hesitation and deep breath, Will eased down his underwear, allowing his cock to snap up and slap against his tight stomach. I accidently gasped a little as I was surprised for three different reasons.

First of all, it really wasn't as long as I thought it would be. I had envisioned this snake like monster hanging down his leg. But in reality, he was probably only about 5 and a half inches. His boxer bulge was probably the result of being a shower rather than a grower.

Secondly, I did find the source of his constant bulges. The boy had balls the size of lemons. And a loose scrotum so that they actually did hang down his leg. That explained so much.

Finally, and what was the main cause of my gasp, was that what his dick lacked in length, he more than made up for in girth. Will was thick. As in, soda can thick. His fingers didn't even meet when his hand was wrapped around it.

"Wow...that's just...wow..." I muttered, not even really meaning to.

He snickered a little, "Yeah, it's a beast. Almost more of a curse than a blessing though. Most girls are too afraid to take it."

"I can imagine," I said drymouthed. Though I had never had anal sex, I couldn't help but feel my muscles clench at the thought of having Will be my first.

I hadn't really noticed that seeing Will's dick and caused me to pick up my stroking again. Suddenly I was almost to the edge again. Our conversation forgotten, we were both quickly stroking and breathing heavily.

Within a few minutes, I felt my balls tighten and cum splattered up on my torso.

Will was still stroking himself, but I noticed he was actually watching me.

"What a mess," he grinned. "I'm sure it feels good though."

"Yeah..." I exhaled. "I should go clean up. Let you finish."

I slipped from my bed, pants still around my thighs. My now shrinking cock hanging defeated. I waddled toward the bathroom and proceeded to clean myself up and redress.

When I returned to the bathroom, I expected Will to be done, but he was still working on it. I kinda paused between our beds, unsure of what to do with myself. In my confusion, I couldn't help but let my eyes wander to his monster cock. Which of course, he noticed.

"Man, I could become a hypnotist with this thing," he joked.

"Oh, sorry," I apologized. "I just...I never knew they could be so...so thick. I can't even imagine."

Will's hand stopped short. A curious glint passed through his eyes.

"Do you...ya know, wanna feel it?" he asked.

"I'm sorry?" I asked incredulously.

"Nothing, nevermind," he quickly amended. "I mean...unless you want to. I don't mind. If you wanna see what it feels like. That's all."

Um...can we say "duh!"?

"Okay...just because I'm curious."

I stepped closer to his bed. Closeup, his thick beast just looked that much more menacing. My slightly shaky hand reached out and found the velvety steel shaft.

Now I have big hands. Bigger than Will's for sure. But even still, my fingers didn't quite meet as I wrapped my hand around the thing. It blew my mind how completely his dick filled my hand. How warm it felt, slightly pulsing.

"If possible, it feels even thicker than it looks," I laughed.

I was just loosening my fingers, when I felt his body give a little thrust. He was definitely pushing his shaft through my closed fist. A hint perhaps? Okay, I would bite.

Rather than release his dick, I slid my hand gently down to the base, til my fingers brushed against the wiry hairs there. Still just barely grasping him, I pulled my hand back up, all the way. I let my thumb brush against his head, also as thick as the shaft. I caught a bead of precum on my thumb, and used it to glide back down again.

"That feels amazing. Girls can barely hold onto the damn thing," Will said.

"Sometimes I guess you just need a man to do things right," I joked, quickening my pace.

I noticed his donkey balls laying down against his leg. My curiousty continued to get the better of me, as I used my left hand to reach out and cup them. Will tensed as I did so, throwing his head back and squeezing his eyes shut. I rolled his giant testicles around in my hand, all the while stroking his shaft faster and faster.

I actually could feel the pull of his balls in my hand before he could even say he was close.

"Don't stop, here it comes," he warned, though I was aware. "Aaaaghhhhhh!"

Will practically screamed in pleasure, his hips pushing up into my still moving hand. I felt and saw the convulsions go through him as he shot his release. And boy, did he ever shoot. Shot after shot of hot cum. And with his hips up and angled, the cum ended up reaching all the way to his chest and neck.

Finally, his orgasm complete, Will laid there gasping for air, covered completely in himself. His cock deflated a little in my hand, but as I had hypothesized, its size remained nearly the same. I let go of him and stood there, feeling awkward yet again (not to mention horny, as my own erection had returned).

"You should go clean up," I suggested.

"Yeah...just wanna lay and bask for a sec. That was intense," he said. "Thank you."

There was a sincerity in his voice that pushed the experience past friends simply messing around.

"Don't mention it," I replied. "Seriously though, don't mention it. To anyone."

"I wouldn't do that," he promised. "It's not something I want to get out there either."

"Good. I think I'm gonna go get some food. While you take a shower."

"Okay," he said. "Hey Shane..."

I had already started walking to the door, but turned around as he called my name.

"Yeah?"

"Maybe tomorrow...I can return the favor."


AN: Hope you enjoyed this latest installment. I know it was a bit of a time jump from Chapter 1 to 2, but most of my experiences take place during the college years. There's more to come with Will, but the next few chapters will center around different exploits with my coworkers.