I was in my first year of college, and this was my first time living away from home and my first time with a roommate, Kyle. Kyle was in a similar situation to mine, but he was from the other side of the country. My parents' house was about six hours away by car, so driving home for weekends wasn't really feasible, but I was planning to visit for winter break.
Kyle, on the other hand, was in school on an athletic scholarship. He was a stereotypical broke college kid -- not like I was rolling in money or anything myself. We made do, ate on campus, picked up odd jobs here and there -- mostly moving furniture on the weekends.
As final exams were upon us at the end of the year, during a study break, I mentioned that I was going to be going home for the winter break and asked if he had any plans. He mentioned that as much as he'd like to go home, the plane tickets were too expensive, and he didn't want to ask his parents to buy a plane ticket for him.
"You can't spend the holidays alone in this sad little room!" I exclaimed.
"Well, what am I supposed to do? It's way too late now -- tickets are going to be double what they were a month ago," Kyle said.
"Come with me!" I said. "I know my parents won't mind, and I have an extra bed in my room. I was always having someone stay over when I lived at home. Friends and relatives. We were like a hotel sometimes, haha."
"I mean, if you're sure it's okay, that would be pretty awesome," Kyle said meekly.
"Bro, say less. You're coming," I insisted. "We can leave right after finals. It's about six hours away without traffic."
"Awesome," Kyle said happily.
We got through finals, talked about what there is to do in my dinky little hometown, and made plans with my parents to make sure they were actually cool with it. Of course, they were.
The day after finals, we loaded up my car, which only took a few minutes since we would only be gone for two weeks.
The drive was pretty easy, and we took turns driving when we stopped halfway for lunch and gas.
We got to my parents' house and I let myself in. My mom greeted us warmly, and I showed Kyle up to my room. He set his bags down on the bed, kicked our shoes off, and we went back downstairs.
We caught up with my parents, and they got to know Kyle.
"Your sister should be here in time for dinner," my dad said.
"Oh, cool! I wasn't sure if she would be able to make it," I said.
My sister was in her last year of college, but she was on the other side of the country, so she was flying in.
"Do you need me to pick her up?" I asked.
"No, she said she's renting a car so she can come and go and visit her friends while she's here, too," my mom said.
Just then, we heard a key go into the deadbolt, and my mom jumped up to greet her.
My mom and sister walked into the living room, where we were all hanging out, and I said, "Riley, this is my roommate, Kyle. Kyle, my sister Riley."
"Hi," Riley said. "My feet are killing me. I underestimated how much walking I'd have to do." She removed her heels and left them next to the other shoes by the door. They were a stunning pair of Louboutin pumps that looked brand new.
"Nice kicks," I said.
"Thanks," she said. "A little Christmas present to myself. I just wish I had worn them sooner to start breaking them in."
"Yikes," I said as she put her feet on the ottoman.
"Beauty is pain, little brother," she said with a smile.
We had dinner and hung out a little more before calling it a night.
"I'm exhausted," Riley said.
"Me, too," I said. "But at least traffic wasn't terrible."
"You should all go to bed," my mom said. "We have plenty of time to catch up."
"Yeah," I said. "I'm gonna take a quick shower before bed. I can show you where everything is," I said to Kyle.
"Cool," he said. "I'll take a shower after you."
We said goodnight and headed upstairs. I showed Kyle around. Since my bathroom was attached to my bedroom, it was a pretty short tour.
"Toilet. Shower. Towels," I said sarcastically as I pointed to each.
"Thanks. I would have never figured it out," Kyle said with a laugh.
I took a quick shower and came out into my room, just wearing a towel around my waist.
"It's all yours," I said to Kyle.
"Cool. Thanks, man," Kyle said.
"It's just a shower. Calm down," I said with a laugh.
"You know what I mean," Kyle said.
"I know, man. Don't even worry about it," I said.
Kyle went into the bathroom and closed the door behind him. I heard the shower turn on, and I started to get dressed, pulling clothes out of my dresser. Just a pair of boxer briefs and a t-shirt to sleep in -- just like back at the dorm.
I started putting a few things away, turned on a bedside lamp, and turned off the overhead light in the room. I got in bed and started playing around on my phone.
Like me, Kyle came out a short while later with just a towel wrapped around his waist.
It wasn't unusual since this is how we behaved in the dorms.
Since Kyle was on an athletic scholarship, he was really trim. He was also small. He was about 5'6" and 135 pounds, but it was all muscle. He was also very into competitive swimming and water polo and was completely hairless from the neck down.
But there was something different about being in my bedroom versus being in the dorms. He looked... different. I tried to ignore the intrusive thoughts that were creeping into my head. I had never done anything with a guy, but I was always curious.
He rummaged through his bag for a pair of boxer briefs, put them on under his towel, hung his towel up on the hook on the bathroom door, moved his bags to the floor, pulled back the covers, and got in bed. No shirt.
"That dresser over there is empty, if you wanna put your stuff in there while we're here," I said as I pointed to the dresser on the other side of the room.
"Oh, cool. I'll do that tomorrow," Kyle said.
I was trying to make him feel at home, plus no one likes to live out of a suitcase for two weeks.
"Are you ready for me to turn off the light?" I asked.
"Sure," he said.
I turned out the light, rolled over, and continued to play on my phone.
After a short while, I thought I heard what sounded like tossing and turning, but it was followed by steady, deep breathing, so I figured he must be asleep.
Then again, a few minutes later, I heard rustling. I slowly turned over to see Kyle's silhouette. About halfway down, it looked like there was movement.
"Dude, are you really beating off right now?" I asked with a laugh.
"What?!" Kyle said in surprise.
"We've been living together for months. You think I don't know your routine by now?" I asked with a laugh again.
"Fuck," Kyle said. "Okay, don't get mad, but your sister is hot, and when she took her heels off, I felt like there was a spotlight on my junk."
I laughed and said, "I'm not mad. If you can land her, more power to you. Is that why you had a pillow on your lap?"
"Yeah," he said with a hint of embarrassment.
"Well, just don't make a mess," I said. "Should I turn on the sound machine or something? Maybe I'll go downstairs for a glass of water. It won't take you too long to finish."
"Oh, my God!" Kyle said. "You've been awake every time?"
"Mostly," I said. "Keep your voice down. We don't need any company."
"Right," he said.
"I'll take my time in the kitchen. I'm sure you need to pick up where you left off," I said.
"Oh, my God," he said with even more embarrassment.
"Do what you gotta do, bro. It's natural," I said as I got up and left the room to go downstairs to the kitchen.
"Uggggh," Kyle said as he pulled the covers over his head to hide his face.
As I walked down the hallway, I noticed I was hard.
"That's new," I thought to myself.
I went downstairs, got some water, and walked around the ground floor for a bit. As I started to head upstairs, I saw my sister's heels. I picked them up to check them out. It had a size stamped into the sole, but it was some weird European sizing system.
The intrusive thoughts won this time.
"Fuck it," I said to myself under my breath.
I came back into my room, and Kyle wasn't finished.
"Damn, still?" I asked with a laugh as I set Riley's shoes down and got back in bed.
"Yeah, when you caught me, it threw me off, and all I've been able to think about is that you've been awake every other time," he said.
"Need some help?" I asked jokingly. Half-jokingly, but he didn't know that.
"I mean... maybe..." he said shyly.
"Whoa, dude. I didn't know you're into guys. Or me, for that matter," I said, genuinely surprised.
"A helping hand is a helping hand, right?" He asked with a hint of irony.
"This is weird," I said.
"You don't have to! I was just joking," he said quickly.
"Now or never," I thought to myself.
"I know I don't have to, but what if I want to?" I asked quietly.
The silence was deafening.
Kyle got out of bed, let his boxer briefs drop to the floor, and walked over to my bed.
His body was perfectly smooth. He must have waxed just before we left. I could see his dick dangling between his legs, semi-erect in the moonlight coming through the window.
I pulled the covers back and scooted over to make room for him, and he quietly got into my bed. I reached over and grabbed his dick. It was warm and thick in my hand. I had never touched another dick before. It was weird, but it felt good. I started tugging on it, and it got fully erect almost immediately.
I brought my hand to my mouth, licked my palm, and went back to stroking him. Kyle moaned softly at my dedication to getting him to cum.
I started to twist my hand as I stroked him, focusing on the head, and before I knew it, his breathing grew quicker, and he was erupting all over my hand.
His breathing slowed as he became more relaxed.
"That was my first hand job from a guy," he said as he got up to grab his towel.
