Girlfriend's Little Brother Pt. 01

I eased my way out into the hall and headed towards the bathroom, my hard cock bouncing in my mesh shorts. Once inside, I shut the door and flicked on the light. Yanking my shorts and underwear to the ground, I freed my hardon and grasped it in my hand, sighing as I stroked it several times.

I plopped down on the toilet and got to work, wasting no time in furiously pumping the hard, heavy cock in my hand. Leaning back to get comfortable, I stretched my long legs out in front of me before yanking my tank top up and over my head to rest the hem along the back of my neck.

My eyes closed and the image of Evan's panty covered ass swam up. I jerked faster, remembering how pale and round it looked in the moonlight, the way it felt silky to the touch against my fingers yet meaty and thick in my hand. I could almost hear the sound of my palm making contact with the underside of those perfect globes and felt a shiver run down my body as I recalled the resulting ripple across his cheeks.

I was getting close, but it hadn't taken very much to get me to this point given how horny I was as well as the vivid memories I was using to get myself off. But what finally pushed me over the edge was the sharpest of them all; how slutty Evan had looked standing in front of me with my handprint on his fat ass while his hard cock tented out of the little red panties he was wearing, betraying just how much he enjoyed my rough handling of him.

"Fuck," I muttered, cum bursting from the tip of my cock.

My body spasmed as thick ropes of jizz splattered all over my chest and stomach, coating my abs and becoming matted in the hair that crowned my pecs. I lost track of how many shots of cum I'd fired before they'd finally subsided, but when I opened my eyes and looked down, I saw just how much I'd released. The amount of sperm that I was covered in made me look like a goddamn glazed donut.

I felt my head knock back against the wall as fatigue took over. Slowly, my breathing got back down to normal and I gingerly stood up, trying to avoid dripping cum everything. Snagging a washcloth from the towel closet, I ran it under the faucet and cleaned myself up, mopping up all the semen before it had a chance to dry too much.

Afterward, I crept back into Cara's room and found her still fast asleep. Sliding under the covers, sleep quickly found me, but before I went under, I came to the conclusion that I had just had the best jerk off session in years.

------

After our late night encounter in the kitchen, Evan avoided me for the next couple of weeks. If I'm being completely honest, I was a bit relieved. I needed some time to wrap my head around what had happened and my response to it all. Then there was Evan himself. I had no idea how this would affect our friendship, especially since I couldn't stop thinking about his ass.

I was constantly fixated on it, how it looked and felt. It astonished me that such a hot little rump could exist on his body. One day, not long after the incident, I caught sight of Evan as I came through the front door. He was going up the stairs and my eyes scanned his backside for any sign of the beautiful ass I had encountered just a few nights earlier. Finding none, I marveled at how hidden it was beneath layers of heavy, oversized clothing, like buried treasure waiting to be unearthed.

I jerked off many times thinking about those twin mounds of pale flesh, replaying the memories of that night so often they felt burned into my brain. A few times I even conjured up those images while having sex with Cara. It turned me on, thinking about her little brother's ass while I was inside her, using the memories of when I groped him to help me fill her pussy with cum.

But the more I jerked off while thinking about Evan's ass, the more curious I became about it, and soon I wasn't just thinking about how it had felt in my hand, but also about how it would feel if my cock was buried inside it.

The idea of fucking Evan slowly began to creep its way into my jerkoff sessions. The first time it happened, I was lying back with my eyes closed and my hard cock fisted in my hand, yanking away while picturing his ass, all round and pale, when my cock suddenly appeared behind it, poised to enter.

I came immediately, surprised by how much the idea of it turned me on. So the next time I jerked off, I went a little further with the fantasy and imagined inserting just the tip. Like before, it turned me on immensely, and I kept taking it further and further each time until all I thought about while jerking off was my rock hard cock pounding Evan's luscious ass over and over.

Despite how much I enjoyed the fantasies though, I still felt out of my depth with all of it. I like to consider myself a very sexual and adventurous person, but I'd never done anything gay before. Not because I was opposed, I just never had any inkling, until now that is.

So one night, I found myself navigating over to the gay side of PornHub. I know that porn isn't a great measurement for how sex with another person would be, but I had been thinking so much about fucking Evan that I was curious as to what that might entail.

After some time carefully filtering out what I wasn't looking for, I was left with dozens of amateur videos, all featuring young, thin guys taking dicks up their fat asses. I watched about half a dozen or so, fascinated and aroused by the content.

I had watched plenty of videos of girls getting plowed from behind over the years, and was surprised by how little a difference there was between those videos and the ones I was currently watching. At least in regards to the asses of who was getting fucked, anyway.

So many of these guys had round, feminine looking asses, just like Evan did. It was mind boggling but also hot as hell; watching big cocks pound them, the noise of slapping skin, the dirty talk.

That was something else that had surprised me; the dirty talk. Not really that it occurred so much as the content itself. I was introduced to a slew of new words and phrases in addition to hearing familiar ones applied in very different ways; twink, boy pussy, breeding. I'd never heard men, or their asses, being referred to in so many lewd and feminine ways before. All of it made my head spin, but also made my cock throb.

Yet, despite my growing interest, I was still unsure if any of this would progress beyond just masturbatory fantasies, or even if it should.

The month eventually changed over to May, and I continued to turn it all over in my mind. My relationship with Cara had begun to encounter the same problems we experienced before but had never addressed.

She noticed how distracted I became over all this. Although I assured her that nothing was wrong, I could tell she didn't believe me, and as a result, she began acting clingy again, although this time she was more demanding of my time and attention, which began to grate on my nerves.

On top of it all, our sex life began to dwindle because of how frequently I was jerking off to this new, inexplicable erotic desire that had piqued my sexual interest, something that created even more tension between us.

It almost spilled over one night while we were out with a group of friends. We had been bar hopping and Cara had drunk quite a bit, more than she normally did. She was already in a bad mood when we left her house earlier after I'd snapped at her for blowing my phone up all afternoon. So as the night slowly wore on, the more alcohol she consumed, and the nastier she became.

She called me a shitty boyfriend several times and accused me of being neglectful. It felt like she was trying to goad me into a fight, but I had refused to take the bait, swallowing my anger after every piercing passive aggressive insult.

I tried once or twice to get her to chill out on the liquor, but she brusquely waved me away.

"So now you care about what I'm doing?" She slurred at one point. "Or is it just so I won't embarrass you?"

I let it be after that and eventually she crossed over from drunk and angry to sloshed and sloppy, forcing me to prop her up as I dragged out of the bar while she berated me for ruining her night.

After a tough wrangling, I finally got her into my car and she passed out on the ride home much to my relief. Despite the fact that I had to pretty much carry her up to her room, I was glad she wasn't awake to start anymore shit.

I sighed loudly and rubbed my temples after depositing Cara onto the bed. This had been the absolute shittiest night and the buzz from what little I had to drink wore off long ago, leaving me with a dull headache. I stared at her slumped body and for the first time wondered if our relationship was worth all the shit I had to put up with.

Stripping off my jeans and button down shirt, I pulled on a black tank top and mesh shorts, then dug through Cara's purse for the joint I'd rolled earlier and stashed inside, desperately needing something to help relax me.

Pulling it out along with a lighter, I slipped my feet through my slides and quietly padded downstairs. It was well past midnight and I didn't want to wake Cara's parents. I stepped out onto the back deck and shut the sliding glass door behind me.

It was cool for early May, and the night air felt good on my skin. I leaned against the wooden railing and put the joint between my lips. The moon was my only source of light and it shone down on me as I flicked the lighter several times, the flame finally catching. I lifted it and lit the end of the joint, inhaling a large puff of smoke.

I held it in my lungs and counted to thirty before exhaling with a sigh, the tingling fog already settling over my brain. I raised the joint to my lips, ready to take another hit, when I saw movement out of the corner of my eye and paused.

Turning my head, I saw Evan on the other side of the door, looking tentatively out at me. We stared at each other for several seconds before he held his hand up in greeting. I responded in kind and he pushed open the door a crack.

"I thought I heard someone out here."

"Yeah, well, I think I'm the only person usually up as late as you."

"Right, right..." he trailed off, looking away.

This was the first we'd spoken in weeks and it was still a little awkward.

"Well," he muttered, "I should probably..." he gestured his head in the opposite direction and moved to close the door.

"Wait."

He paused, looking back.

"I just lit this," I held up the joint, which trailed smoke. "Why don't you help me polish it off?"

Evan bit his lip, unsure. "Really?"

"Yeah man, you're still my smoke bud."

A small smile broke out across his face and I thought I saw some relief there as well. He stepped outside, and as he turned to shut the door behind him, my eyes scanned the loose joggers and oversized t-shirt he was wearing, and I wondered if he had on another sexy pair of panties underneath.

He slowly walked up to me until we stood facing each other. I offered him a hit of the joint and he took it. Evan still looked a bit nervous to be around me, and I smiled to let him know all was well.

"So how are you feeling about finals, man?"

"Well," he said, coughing slightly. "I'm a bit worried about my experimental drawing class but I think it'll be ok."

"I don't think you have anything to worry about. You're a great artist."

He blushed and looked away, a small smile on his face, "Thanks, Seth." He took another quick hit before passing it the joint back over.

"So, experimental drawing, huh?" I took a long drag.

"Yup."

"What makes it experimental exactly?"

"We use techniques and materials that aren't commonly used for drawings."

"That sounds really cool, actually."

"It is, I think it's my favorite class I've taken so far. It really pushed me to be more creative and think outside the box regarding my work."

Little by little, as we stood out there talking and getting high, the awkwardness slowly melted away until we were joking around like nothing had ever happened.

The joint was nearing its end as I passed it off, both of us giggling at some stupid joke I'd made. It petered off as Evan took a hit while glancing up at the sky, both of us now silent.

"You know, I'm glad I decided to come out here," he said suddenly. "I almost didn't."

I looked at him. "How come?"

He hesitated, dropping the finished joint into the ashtray on the railing, before slowly proceeding, "I thought it would be really weird between us."

"Because of what happened," I said in a low voice, and he turned away from the night sky toward me, making eye contact. "That night in the kitchen."

"Y-yeah," he whispered. "I thought you'd be freaked out."

"I wasn't. You didn't need to worry."

He chuckled a bit nervously, "Well can you blame me? Guys really don't enjoy finding out they were groping another dude instead of a girl."

I paused, contemplating my next words carefully before saying, "What makes you think I didn't enjoy it?"

His eyebrows raised dubiously, "You enjoyed groping my ass?"

I shrugged. "It's a nice ass."

He smiled like he thought I was joking.

"Alright, what makes it so nice then?" I watched his smile turn smug as he called me out on my perceived bluff, and I could tell he wasn't expecting a genuine response.

His challenging tone and the glint in his eye triggered something. Feeling suddenly bold, I looked him dead in the eye, holding his gaze intently, and in as serious of a tone as I could muster, I began telling him everything I had surreptitiously been thinking the last several weeks.

"How big it is," my voice came out clear and certain. "Not in an unhealthy way, but supple. It's so thick and round."

I emphasized each adjective and watched his smile falter a bit, the first signs of doubt starting to trickle through as he began to question if I was actually joking or not. My heart leapt in my chest and I took a half step towards him, still holding eye contact, a subtle thrum of excitement suddenly running through me.

"And that silky, smooth skin; so pale and sensitive. Even in just the moonlight, I could clearly see my handprint practically burnt onto the surface after I spanked you."

His smile slowly disappeared the more I talked, the gravity of my words finally sinking in. I felt my cock stir slightly inside my shorts, bristling at the hint of sexual tension beginning to permeate the air, and I leaned in just a bit closer to Evan.

"Then there are those cheeks, those two shapely mounds. I couldn't believe how your little lace panties made them look," I prompted.

"How... how did they make them look?" He spoke in quiet disbelief, his smile completely gone now.

A sultry grin slowly spread across my face as he appeared enticed into whatever this was.

"Slutty," I proclaimed emphatically.

I heard his breath hitch slightly, a light shiver running across his body.

"They looked ripe and slutty," I continued, "practically bursting out of those snug, red panties that barely seemed to contain them."

My cock was now half hard from our conversation and the knowledge that I had enticed Evan into this provocative back and forth. He was taking heavy breaths, staring up at me with those big blue eyes full of excitement and terror; his face that of prey willing and allowing itself to be lured in. It fueled a sexual adrenaline that urged me forward, the corners of my mouth turned up in a sly, inviting grin as I spoke.

"But you want to know what I liked best about your ass, Evan?"

"What?" He breathed. "What did you like the best?"

"How it felt in my hand when I squeezed it; soft, but incredibly firm at the same time. I've never felt an ass that magnificent before."

He swallowed loudly. "Really?"

I nodded my head, "Uh-uh, and you wanna know something else?"

Evan nodded his head, slow but deliberate.

Leaning in closer still, I said in a husky voice, "I haven't been able to stop thinking about how good it felt ever since."

His eyes grew wide, searching mine for confirmation; he was still checking to see whether this was all real or if I was messing with him. So I pushed even further, unsure of what would happen but eager to find out.

"I've been playing the memory of that night over and over in my head for weeks; just constantly thinking about your ass, how it looked, and remembering the feeling of it clutched tightly in my hand while I jerk off."

My words hung heavily in the air as we stared at one another in sexually charged silence, both of us waiting, anxious and almost giddy, for whatever would happen next. Finally, Evan took a deep breath, steeling himself to speak, and I felt my cock twitch in anticipation for what he would say.

"Do you want to feel it again?" His voice was low, but clear and full of determination.

I felt my heart skip a beat in excitement, and I nodded before stepping close to him, still holding eye contact. His lavender shampoo was all I could smell, and I breathed it in as I reached under his t-shirt with my right hand and cupped his side. Another shiver ran through him when my coarse fingers made contact with his soft skin.

The erotic tension pulsed between us, and I just stood there holding his side, letting it wash over me. Slowly, I slid my hand to the small of Evan's back, pausing before the tips of my fingers pushed under the waist of his joggers.

Almost immediately, I encountered thin, frilly fabric, confirming my earlier question of whether or not he was wearing panties again. Evan blushed slightly at my discovery, and offered me a small smile. I smiled back, conveying that I enjoyed what I had found.

I continued on, my hand slowly glided down the slope of his ass, marveling at the way it flared out and taking great pleasure in the feel of his smooth, delicate skin. My fingers splayed out as I centered my palm along his left cheek. Pausing briefly, I let the tension and anticipation simmer before my large hand finally enclosed around the puffy mound of milky flesh, squeezing it with all the strength I had.

Evan inhaled sharply, rising up on his toes as my fingers dug harshly into his skin. Our faces were only a few inches apart now, and we held intense eye contact while I mercilessly crushed his spongy, circular ass cheek in my relentless grip. I exhaled slowly in relieved satisfaction, my breath coming out ragged and heavy. Evan's lips, parted slightly from excited wonder, quivered from the pressures on his ass.

We stood like this, our bodies nearly pressed together, for almost a minute; two men reveling in searing sexual pleasure derived from finally fulfilling illicit and long held fantasies.

Eventually, I slowly began to relax my grip, watching as Evan rolled back onto the flats of his feet, until I was gently cupping his ass.

Both of us were breathing heavily, and he peered at me curiously from under his eyelashes, suddenly shy.

"Did... did you enjoy it?" He asked, watchful eyes questioning.

"You tell me."

I took his wrist with my free hand and brought his open palm up to my crotch, pressing it against the bulge of my now fully hard cock.

Evan's eyes went wide as my clothed cock writhed against his touch. I held his hand there, watching his stunned reaction while I flexed my dick against his palm and fingers. It took a few thrusts before he snapped out of his shock and finally picked up on what I was trying to get him to do.

I let go of his wrist once he started rubbing my bulge on his own. Sighing, I closed my eyes and began running my hand across the bottom of Evan's ass.

We spent the next few minutes just touching each other; I stroked Evan's asscheeks in between tight gropes, enjoying the squishy feeling of his plump globes molding around my clasped hand, while he palmed and gripped my stiff cock through the material of the mesh shorts I was wearing, forcing small grunts of pleasure from between my lips.