Falling for My Best Friend

By Jack Case

Published on Jan 12, 2019

Bisexual

This story is loosely based on several people I have met and a variety of situations I have encountered as a boy and young man. While many of the encounters actually happened in some manner, my experience didn't end like the one related here. This story is instead more of a collection of combined memories that have been revised for a happier ending.

CHAPTER 2

Late one Saturday morning, Jake emerged from his bedroom dressed in a familiar pair of green shorts that were cut high on his leg and that always drove me crazy, along with a tight t-shirt with an obscure band logo.

"Hey Noah," he said, "I'm going for a run."

Even though he was out of school and no longer part of the track team, he still enjoyed running and ran whenever he had time. I looked at him but tried not to stare. He turned away from me to get a glass of water from the sink. His pert, muscled ass prominently filled his tight shorts. My heart seemed to skip.

"How long do you think you'll be gone?" I asked.

"Not sure...why?"

"It's very hot out there today. Just wondering when I should call 911 to retrieve your missing and presumed dead body." I replied.

He smiled. My knees felt week. I always felt happy when I could make him smile. I pretended to keep reading my book, looking only from the corner of my eyes as he stretched his muscular legs and arms before heading out. His shirt rode up and I could see his cut abs.

"See you later," he called as he headed out the door. "I'll try not to die."

Even after he had gone, I couldn't get the vision of him out of my mind. Standing in the kitchen, in his short shorts; muscled arms, flat stomach, and a pert ass. There was no way I could finish my book.

I got up and, with a twang of guilt, walked to the doorway of this room. Opening the door, I looked in. It was a mess. His bed was unmade and clothes - both dirty and clean - were scattered about the place. But it was the smell that drove me nuts. There was something about him, some pheromone, that I seemed to be particularly susceptible to. Whenever we were close to one another, his smell would make my heart race.

I stepped into his room. I think that was the first time I was in there without him. I lay down on his bed, and breathed in deep of his scent from his pillow and blankets. It smelled like him - strong and masculine. Oh god, he was driving me crazy. I imagined being here just a few days ago, perhaps it could have been me instead of Heather.

Deciding I needed a break, I gathered some stuff and left the apartment to visit a friend across town. By the time I returned a few hours later, Jake had already returned and showered, and was preparing to head out to meet Heather for dinner and a movie.

"Aren't you gaming with the guys tonight?" he asked.

"No," I replied, "Dave and Steve couldn't make it tonight, so I'm on my own. Guess I'll watch some tv tonight; maybe order a pizza."

"Well, have a good time. Don't go making any messes!" he said with a wink. And with that, he was out the door. My heart skipped. What did he mean by that? Make any messes? Did he somehow know about the other night when I jerked off listening to him and Heather having sex? I mean, I wasn't an otherwise messy person. To distract myself, I decided to walk down the street to the nearby pizza place and pick up my supper. By the time I returned, I had written off Jake's comment as just a joke and nothing specific to the night I creamed my briefs really badly.

After eating, I decided to pee before settling down to watch some television. Walking by his room on my way out of the bathroom, I couldn't help but hesitate and look into his room. It looked apparent from the mess that was in his room that he wasn't expecting Heather to come home tonight. His bed, which was perpetually unmade, looked more of a mess tonight than usual, and his dirty clothes were scattered about the floor; including his green running shorts. My heart stopped. I knew I shouldn't, but I felt powerless. I had to at least look at them closer.

Entering his room, I was drawn to the green running shorts. Lifting them from the floor, I realized that his striped briefs still sat inside the shorts - he had taken them off together. If his room smelled like him, these shorts were a concentrated blast of all the musky smells - sweat, cum, piss - that were his. I brought his shorts and underwear, which were still damp with the sweat of his run, to my face and inhaled deeply. Oh my god.

My cock began to swell in my pants as my heart went into overdrive. Looking out into the empty apartment as only a guilty person would, I checked to be sure the coast was clear before heading back to my room with his running shorts and underwear.

"Is this what he meant when he said don't go making any messes?" I thought. Was he setting me up? I didn't care, and couldn't have stopped myself if I wanted to. I quickly jumped onto my bed and pulled my pants and underwear down exposing my stiff cock and full balls. I placed his shorts completely over my face. Only a few hours ago, his cock and balls and ass had been here. I began jerking myself off as I breathed in deeply his masculine scent. It didn't take me long to get close to cumming, and I knew what I wanted to do. I wanted - no, needed - to cum in his underwear. I wanted to spray my hot sperm right where his sweaty cock and balls and ass had just been. It would be like I was cumming on him.

I felt my balls tighten as my orgasm approach. Quickly, I pulled his shorts from my face and wrapped them around my stiff cock. In only a few strokes, I had the most intense orgasms of my life, and my dick exploded, sending multiple volleys of sticky cum into Jake's underwear. It felt almost like I was coming inside him, or at least on a very intimate part of him.

As my breathing slowed, I removed the shorts from around my cock to reveal the mess I had made. Jake's face flashed in my mind and I heard his voice saying "Don't go making any messes." A huge load of my cum now sat in the crotch of his underwear, which had gone from already damp to now soaking wet. There was no way he wouldn't notice the wet stain I had added to his shorts. For a moment, I didn't know what to do. If I let it sit any longer, it would most likely soak through the underwear and stain his running shorts. So I did the first thing that came to mind - I brought the mess to my face, and buried my tongue in my warm salty, cream, and began licking it out of the crotch of his used underwear, imagining that it was Jake's load I was eating. When I was done, his underwear was soaked with my spit and residual cum, but not too much worse than when I found them.

"Oh my god," I thought, "he is going to drive me crazy." I replaced his shorts on the floor of his room where I found them, and went back to my original plan of watching tv. I found it very difficult to concentrate on anything for the remainder of the night, and ended up heading to bed before Jake got home. "Probably for the best," I thought. "In the mood I'm in, I'd likely throw myself on him when he gets home."

**

The next morning, I awoke late with no intentions other than eating a big bowl of cereal and enjoying a Sunday before I went back to classes. My jaw dropped, however, when stepping out of my bedroom I saw Jake already awake and dressed for a run - in the same green running shorts that I had masturbated into last night! He looked at me with a smile.

"Going for a short run. See you in a bit!" And with that, he was out of the door. I didn't recall him having multiple pairs of those shorts, but would he have thrown on dirty (dirtier than he realized) shorts and underwear to go for a run, since he would just shower when he got home? Looking out the window to be certain he was gone, I quickly ducked into his room. The shorts that I had placed on the floor last night were gone.

"Surely he would have at least put on clean underwear," I thought. I stuck my head into his closet where his tall laundry basket stood. There on the top were the striped briefs that he had worn yesterday, and I had used last night. My libido raced, as I grabbed them and hurried back to my room. I stripped off my underwear and t-shirt, and slid Jake's used (and still damp) underwear on. My cock hardened, stretching out the front of his shorts.

"Is this what they look like when he gets a boner?" I thought. I pulled my cock up flat to my stomach, and began stroking myself through his shorts. The head of my cock stuck out of the waistband and was leaking pre-cum onto my stomach. I stroked myself faster and faster, feeling his tight underwear cradle my ass and balls, just like they held Jake.

"Oh fuck, I want you," I whispered as I stroked myself harder. "I want to suck your cock. I want to swallow your cum." Looking at my cock leaking onto me, I knew it wouldn't be long before I blew my load. Throwing my legs up into the air, I flipped over so that my cock now hovered over my face. Looking at his underwear, I imagined it was his cock that I was stroking. "Fuck, give it to me Jake! Give me your cum!" My balls pulled tight to my body and I began a long, intense orgasm, as I began to cum. I opened my mouth wide in hopes of catching it. Five heavy blasts of thick cream - some into my mouth and some across my face - left me drenched in sperm and smelling of sex.

As my racing heart began to slow, I returned my legs to my bed, while using my fingers to collect some of the poorly aimed cum and bring it to my mouth. I savored the taste, and swallowed it. "This," I thought "was going to be a good Sunday morning." That is until I heard the door open.

"Noah, you still up?" It was Jake. And here I was, lying naked except for his dirty underwear, my dick still half hard, and my face covered in my own cum. And most of all, my bedroom door was open. I pulled my blanket up over myself just in time, as he popped his head into my room. "Back in bed?" he asked. I tried to nonchalantly put my hand to my cheek, in hopes of hiding the evidence of cum there.

"Sorry to disturb you," he said with a smile. "There was a lot of construction along my route, and then a car almost ran over me, so I figured it was fate's way of telling me to skip the run today." I felt myself turning red, embarrassed to be caught like this, cum on my face and only a blanket hiding the fact that I was wearing his used underwear.

"Think I'll jump in the shower. You should shower, too," he said with a wink, "You're a mess."

He left my room and headed to the shower, closing the bathroom door behind him. I jumped up quickly, stripped his shorts off, and put on my own clothes. Looking in the mirror, I could see wet marks across my cheek and chin from my cum. "Oh fuck," I thought, "he knows."

Once I heard the shower run, I ran into his room and hastily placed his underwear back into his laundry basket. Hopefully, he didn't notice that they were missing. Once he was done and out of the bathroom, I took a long shower hoping to avoid him at all costs. But to no luck. When I emerged, Jake was busy making pancakes for us. "Hurry up and get dressed," he said, "Breakfast is almost ready."

We spent the rest of the day hanging out together. While I was extremely embarrassed at first, Jake was especially friendly and funny today. As always, I enjoyed his company. I guess this day turned out pretty good after all.

**

CHAPTER 3 A week had gone by and nothing else had occurred. While there were opportunities for me to get into some mischief (and his clothes basket), I tried really hard to behave. As a couple of weeks passed, I noticed that Jake wasn't going on any dates. His mood was changing, too, from generally friendly to quite grumpy. He didn't talk as much to me and seem aggravated by the smallest things.

I tried to broach the subject with him one weekday night when we had just finished dinner. "So what happened to Heather? I don't see her around here much lately."

His angry eyes locked onto me. I was about to apologize for asking when he replied "We're having a bit of a break. I don't know if things are going to work out."

"I'm sorry to hear that," I replied sincerely. "She seemed nice. I think I liked her the best of all of your girlfriends." After a pause, I added "I hope things work out for the best for you."

I couldn't tell if he believed me, or if he blamed me for his troubles. I wonder if they knew about me eavesdropping on them that night, and it had caused problems. I tried to give Jake wide berth the rest of the week, in hopes that I wasn't the cause of his anger and girl problems.

That Friday night, I saw no sign of him. I went out with friends and came home to an empty house. It wasn't until 1:30 that I awoke to the sound of him coming home. By the sounds of it, something was wrong. He was stumbling and knocking into things when he typically was a quiet person. Not wanting to be the target of his anger, I waited until things quieted down before poking my head out of my room.

The bathroom light was still on, casting a faint light into parts of the apartment. I stepped out to shut it off when I saw Jake laying half on his bed, and half off. His shirt and sneakers were off, but he still had one leg of his jeans on. It looked like he had passed out. I stepped in slowly and quietly asked "Are you alright?"

His eyes opened a crack to look at me before closing again. I stepped in closer and could smell the alcohol on him. Jake didn't drink. Ever. But it looked like he was drunk. Not sure what to do at first, I grabbed the leg of his jeans and pulled his pants the rest of the way off, all the while trying not to let my hands linger too long on his hard, muscled legs. Lifting him up, I pushed him onto his bed and began pulling his sheet over him.

"Let me get you some water and aspirin," I said.

Retrieving them, I helped him take the pills and drink most of the water before he collapsed back into his bed. As I was about to stand, one of his hands came up to grab my arm. "You're a good friend," he slurred. "You always take good care of me."

Sitting on the edge of his bed, I tried my best not to stare, but this was the closest I had ever been to him when he was clad only in those small trunk-style briefs he liked to wear. His body was toned with a light fuzz of hair leading from his belly button down to his groin. He rolled on his side, facing away from me, kicking most of the sheet off of him.

As I stood up to leave, he said "Don't go. Stay with me." I sat back down, unsure what he wanted. Perhaps he wanted me in case he got sick. Perhaps he was just lonely. "Thanks," was all he mumbled before seeming to pass out. I waited a few minutes until I could hear his breathing become slow and shallow. The entire time, his V-shaped back and marvelous ass were facing me. I couldn't help but stare.

Terrified that I was only making things worse, but unable to stop myself, I slowly reached out until my hand softly landed on his upturned butt. It was extremely hard, like it had been carefully sculpted from stone. I moved my hand slowly, feeling the ass that I had admired for many months now.

"I need to get out of here before I do something stupid," I thought.

I removed my hand but before I could stand up, he rolled over onto his back, leaving his entire front exposed to me, including a pronounced bulge in the front of his shorts. Jake was truly a beautiful guy, and his personality just made him that more attractive. How could any woman (or gay guy for that matter) not want him? The light from the bathroom shed enough light to accentuate all of the cuts of his wiry muscles on his thin, runner's frame.

His cock throbbed in his underwear, stretching the material even further. "Oh god," I thought. This was too much for me. My willpower was overwhelmed, and I reached out slowly to touch what I had so long wanted. With one last look at his face and seeing no movement, I brought my hand down onto the large bulge that formed from his large balls and hardening cock. It was so hot to the touch. I slowly moved my hand up and down his length, each time feeling his manhood move and respond to my touch.

With one last feeling of guilt, I removed my hand and started to get up when I heard Jake mumble "Get them off."

Get them off? What was he asking? Did he really want me to take his underwear off? Was he even conscious? Did he know it was me? Perhaps he thought it was Heather or one of his past girlfriends.

"Get them off," he repeated.

Feeling like I was in a dream, I reached out to take hold of his waistband in both hands, and slowly began to lower them. To my surprise, he lifted his ass off the bed, making it easy to slide his shorts down this thighs. I couldn't believe this was happening. More so, I couldn't believe the beauty of his dick. Not quite hard, it curved up along his belly, ending in a large, pronounced head. His balls were large, too, and his groin was framed in a bush of dark hair.

My hands were shaking when I reached down to grasp his cock, and begin to stroke him. He didn't seem quite awake, but he let out a light sigh. I stroked him faster, feeling his erection hardened in my hand. Hovering over him, I could smell that scent that I had come to love, and which drove me crazy. Whatever was in his pheromones, I was defenseless against them.

Before I could stop myself, I leaned over and took the head of his swollen cock into my mouth. I had never sucked someone off before. The only sex I had had was mutual hand jobs with a friend in junior high school. Jake lifted his ass off the bed, surprising me as he tried to drive his cock further into my mouth. Frightened at first, I took a deep breath and proceeded to take him as deep as I could. I slid my mouth over his enormous head again and again, but being inexperienced, could only go about halfway down his shaft before choking. I brought one hand up to stroke the remainder of his cock, and the other to nestle and rub his balls, which were beginning to pull up tight to his body. I didn't know how far this would go, or if I would ever have this chance again, so I increased my movements, sucking and stroking him the best I could. After only a few minutes, he let out a low moan and I felt his shaft swell even larger in my mouth and then begin to pulse. I was surprised when his cock began to shoot cum into my mouth, and frightened when I felt his hand grasp the back of my head, holding me tight to his groin. I could do nothing but swallow as quickly as I could, as multiple shots of thick cum filled my mouth beyond capacity.

Finally, he was done, and his hand dropped back to the bed. He didn't move. I released his spent and softening cock from my mouth, and pulled his shorts up the best I could. "Did that really just happen?" I thought. My mouth tasted like Jake's cum, and my nose was filled with his musky scent.

I quickly made my back to my room, closing my door behind me. I was more afraid than turned on. Even though I had always dreamed of having sex with Jake, I was afraid that I had just destroyed our friendship, which was more important to me. In fact, I hadn't gotten hard during the entire encounter. Would he even remember what happened? Would he want to move out? I went to bed an emotional wreck, and scared to even see my best friend the next morning.

**

I slept late the next morning, and awoke to find no sign of Jake. His car was missing, too, so it wasn't that he was just out for a run. I looked into his room and at his unmade bed. I felt like I was looking at a crime scene, or at a historical marker of where our friendship ended. I felt sick to my stomach. Not wanting to encounter him should he return, I got showered and dressed and headed out of the house as quickly as I could. I spent the day hiking and thinking, and trying to clear my head. I would do anything to salvage our friendship, if that was even possible now.

Jake never came home that night or the next morning. It was late in the day on Sunday when I heard his car pull into the driveway, and him coming up the stairs. I didn't know where to go. Should I hide back in my room, or confront him and get this over with? I tried to steel my nerves for the worst.

He popped through the door carrying a small overnight bag and an empty water bottle. "Hey," he called out in a relatively cheerful voice. He headed straight to his room and dropped his bag, before rushing into the bathroom to pee. I stood uncomfortably in the den, a few steps outside of my room (in case I had to retreat to safety). After a few long minutes, I heard the toilet flush and he stepped back out. "Wow, I had to pee!" he said, "So what's new?"

I was dumbstruck and stammered for a moment. "I...I...ah, nothing." And when that didn't elicit a response, I continued. "I was worried when you didn't come home."

"Sorry about that. I needed to...clear my head a little. I went to my mom's new house out of state and stayed there. I guess I should have told you."

He seemed genuine and, more importantly, not mad at me at all. I was confused.

"It was a long drive. Took me 6 hours to get there. Nice place, though. Oh, she said to say hi. Said you should come over the next time I go to visit. I haven't eaten since breakfast. You interested in getting something for supper?"

I truly didn't know what to say. "Um, okay."

We spent the rest of the evening getting takeout, kidding around, and just enjoying each other's company. It took me a couple of hours before I began to let me guard down. We talked about his past girlfriends. He said he always felt that while he was always concerned about their happiness, the feeling wasn't mutual. I admitted that I thought many of them were selfish and high maintenance people. He agreed. He said that while he liked Heather, she wasn't interested in a relationship right now.

And then he said "About the other night...."

I could swear that my heart stopped in my chest. I could feel tears welling in my eyes. "I'm so sorry, Jake," I said through short breaths, "I'd do anything to take it back. Your friendship means more to me than anything. I'm sorry I did what I did and messed everything." I dropped my eyes to the floor. I couldn't even look at him. And after a short pause, "Please don't hate me."

Jake reached between us, and softly cupped my chin, bringing my face up to look at him once again. Then I received the biggest surprise of my life, as he leaned in and kissed me, soft and gentle and lovingly on my mouth. My eyes closed and I was in heaven. It took a moment after he stopped before I could open my eyes, not wanting this dream to end. When I did, he was looking at me with a smile.

"You know, it's kind of hot on how turned on I can make you," he said. In my stunned silence, he added "Don't think I haven't noticed how you look at me. Ever since we met, I had a feeling you found me attractive. It wasn't until we moved in that I realized that you really liked me. That's one of the reasons I went to talk to my mom. I told her everything. I told her how I wanted a girlfriend who was as kind and considerate of me as you are. Someone who is a good friend, like you are. Someone who thinks I'm hot, like you do."

"You told your mom that I think you're hot?" I said in a panic. "Actually, I told her everything." Now his eyes looked worried. "I told her how I came home drunk, and you put me to bed, and then, well...things happened."

I couldn't believe that he told his mother. My face must have turned red. He chuckled. "Don't worry. She said that she always thought you were nice and asked if I liked you. The more we talked and the more I thought about it, I realized you did fill all of the requirements I'm looking for in a partner. She told me that love is about finding a close friend who makes you a better person; who helps you be true to yourself."

I didn't know what to say to him.

"She also said that she thinks it's apparent that you like me, and that we care for one another. So she suggested that I try taking the next step with you. I've never thought of myself as gay, and I'm not sure if this will work, but I'd be open to you being my `girlfriend' if you're willing to give it a try."

I sat there trying to understand what he was saying. I could almost cry. "But what about our friendship? I wouldn't want to ruin it. What if..." was all I could get out before he leaned in and kissed me again. My eyes closed and I melted in his hands. This kiss was stronger, more passionate. I felt the tip of his tongue enter my mouth and I let him. We kissed for several minutes, before he released me.

"How about we take it slow to start with?" he asked. "Think of it like we're still best friends and roommates, but now with benefits? We can try it for a while and if either of us doesn't like it, we go back to being just friends. What do you think?"

"I don't know," I responded. "What if it doesn't work?"

"What if it does?" he countered.

"But what if you get mad at me, or I get jealous of you once it doesn't work, or we can't go back to being just roommates, or..."

"You know," he interrupted, "If you're going to keep coming up with possible problems, I'm going to have to kiss you again."

I looked deeply into his brown eyes. "Is that supposed to be a deterrent?" I said with a grin. He leaned in once more, as did I, and we kissed again, his hand coming up to run through my hair and down my neck. I reached out to hold his strong arms and shoulders, and returned in that kiss all of the pent-up passion that I had hidden from him over the past months.

When we finally broke the kiss, he said "Well tomorrow's a workday. I suppose we should head to bed." He stood, and reached out to my hand to pull me up from the floor. I felt like I was walking on air.

"Okay. You're right. We can talk more tomorrow. Have a good night, Jake." I drifted as if in a dream, taking two steps toward my bedroom when he called out to me in a whisper. "Well, are you coming to bed?"

I turned to see him, hand outstretched. I stepped back and took his hand, and he pulled me into his dark room, closing the door behind us.

**

Next: Chapter 3: Falling for My Best Friend 4 5


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