College Roommate Cums Home With Me

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.

"That was my first time giving one to someone who wasn't me," I said as he handed me his towel.

I wiped my hand off and let the towel drop to the floor.

"I want to feel what it's like to give one," he said as he started to get back into my bed.

"Sure, but on one condition," I said.

"I swear I won't tell anyone," he said preemptively.

"Okay, two conditions," I said with a laugh.

"What?" he asked.

"Put those on," I said as I pointed to Riley's heels at the foot of my bed.

Kyle looked around my room, trying to figure out where I was pointing.

I grabbed my phone, turned on the flashlight, and showed him.

"Oh, man. Are you serious?" He asked incredulously.

"Yeah. I bet they'll fit. You're small, like a girl," I said deviously.

"I dunno, man," Kyle hesitated.

I pulled my covers back to show him the bulge in my boxer briefs.

"Ugh, fine!" he said resignedly.

He walked over to the black patent leather pumps that were reflecting the light of my flashlight and started to step into the right shoe. It popped right on.

"See? Perfect fit," I said with a smirk.

He put his hand on my bed to balance himself as he stepped into the left shoe.

"Damn, these really do pinch," he said as he got in bed with me.

I pulled my boxer briefs down, he immediately grabbed my dick and started tugging.

After about a few minutes, he moved his head down to spit on my dick, and without thinking or hesitating, I pushed his head toward my dick.

Seemingly also without thinking or hesitating, Kyle opened his mouth and started sucking my dick.

"Oh, fuck!" I exclaimed. "That feels really good."

Kyle turned his head while he bobbed up and down, then he started to grab my balls. Squeezing and caressing while he made a slobbery mess all over my dick.

He pulled his mouth off and came back up next to me and continued stroking.

"Your dick feels so good in my hand," he said as he was catching his breath.

"I bet it would feel even better in your ass," I said jokingly.

He rolled over and said, "Do it."

"Wait, what?" I asked, surprisedly.

"Fuck me before I change my mind," he said.

Without hesitation, I started to work my dick into his tight little asshole.

"Fuck, you're tight," I said as I tried to push in.

"I've never had anything up there before," he said through small grunts of pain.

"Stand up," I said.

He got up, and I followed him. I grabbed my phone and started recording with the phone's light on. I set my phone down on the nightstand, hoping I was getting everything in frame.

I turned him around to face my bed and said, "Bend over. Spread your feet a little."

"I've never worn heels before. I'm trying to keep my balance," he said.

"Put your face on the bed and spread your ass," I said, ignoring him.

He listened obediently and I started to work my dick into his ass again and after slowly pushing against his asshole, it suddenly popped in.

He gasped in surprise. I grabbed his wrists and held his arms behind his back as I slowly pushed my dick all the way in his ass.

Once I was all the way in, I asked, "Are you ready?"

He was biting my sheets, but I could see him nod enthusiastically.

I started pumping his ass as I held his arms pinned behind his back.

Eventually, he loosened up a bit, and I let go of his arms and grabbed his hips. He pushed himself up to stand.

"Fuck, you were right. You feel so good in my ass. Don't stop," he said.

I reached around to grab his dick and he was rock hard again. I started stroking him while I fucked his ass.

"I'm going to cum again," he said.

"Cum with me," I said.

I could feel his dick start to erupt again and his asshole was clenching around my dick.

"Cum in me," he said.

I kept pumping his ass and stroking his dick as I started to cum.

"Fuuuuuuck," I said as I let loose a steady stream of jizz in his ass.

"Uhhhh, uhhhh, uhhhh," he moaned as he came all over my hand again.

I kept cumming in his ass as I put my fingers covered in hot, sticky jizz in his mouth.

He sucked on my fingers as I slowed down in his ass.

I slowly pulled out of his ass and wiped my dick off with his towel from earlier.

He took the towel from me and wiped his dick and the bed as best as he could.

He walked to the bathroom, still wearing the heels, and closed the door. He came out a few minutes later, still wearing the heels, and said, "It won't come out. You fucked me pretty deep."

He picked up his boxer briefs, put them back on, and sat on his bed. He took the heels off, rotated his foot a little, and said, "That was fun. Better than I expected."

"Yeah, and the heels made you the perfect height," I said.

"I might have to get a pair when we get back to the dorms," he said.

"Oh, yeah?" I asked.

"Yeah. You think I'm gonna let you not do that again? If I had known that's what it was going to be like, I would've done it the first week we moved in," he said.

"Oh, really?" I asked.

"Yeah. If you weren't stroking my dick, I probably would've cum again anyway. Plus, in the dark, a hole is a hole, right?" he asked.

"For sure," I said with a smirk. "I mean, you're small, hairless, and you have a mouth and an ass to use. It's not a huge leap with the lights off," I agreed.

"Make a note of the size of those heels," he said as I was putting my boxer briefs back on. "I definitely want a pair if that's what it does to you."

I picked up one of the shoes, turned it over, grabbed my phone off the nightstand, stopped the recording, and took a picture.

I sent him the video and picture of the bottom of the shoe.

A few minutes later, he asked, "Whoa, you recorded that?"

"Yeah, man. You think I was gonna let the opportunity pass me by?" I responded.

"Damn, my legs look good in these," he said. "Thanks for sending it," he said.

"I'm gonna go put these back because there's no way I'm going to be awake first tomorrow after all that," I said with a smirk as I picked up the other shoe.

I quietly crept downstairs, put the shoes back where Riley had left them, and made my way back to my room.

I got back in bed, and I could tell Kyle was already asleep. I quickly fell asleep, replaying what had just happened in my head.

The next morning, we woke up, got dressed, but neither of us mentioned what had happened the night before, until we were leaving my room to go downstairs.

"Your jizz is still in me," Kyle said with a smirk.

"I guess that makes you my bitch," I said with a laugh.

We got downstairs, and breakfast was nearly ready. We sat at the table, and my mom asked how we slept.

"Great," Kyle said. "I fell right to sleep almost immediately. That bed is way better than what we have in the dorms."

"Good," my mom said. "It sounded like you guys were up late."

"Not really," I said. "I gave him a short tour, showered, and pretty much just went to bed." I came down for water in the middle of the night, but I went right back to bed after that.

"Hmm," my mom said.

Riley came downstairs, already dressed and ready to head out.

"Don't you want breakfast?" my mom asked her.

"No, thanks. I'm meeting some friends for brunch to catch up," she said.

She looked down at her shoes and said, "Okay, let's try this again..."

She started to step into the right shoe, and as it popped on, she said, "Hmm." Then she stepped into the left shoe and said, "Oh, my God!"

"What?!" my mom asked in surprise.

"They fit perfectly now! Maybe I was just swollen from the plane yesterday," Riley said.

"Oh, yeah. My rings get tight whenever I fly, too," my mom said.

Kyle and I exchanged glances and shared a smirk. Apparently, getting hot and sweaty while getting fucked is all those heels needed to create some give.

Kyle and I spent the rest of winter break fucking and sucking. Every night, one of us crept downstairs to borrow Riley's heels. She even had a few pairs in her closet that we knew she wouldn't miss. I eventually let him fuck my face, but he never tried to fuck my ass. In hindsight, I can tell you that he was saving that for when we got back to the dorms, so he could punish me for stretching his asshole and filling him up every night.

I even got some road head on the drive back to our college. He was one dick-hungry little slut.

Stick around for the next story about how we worked things out and came to an arrangement.