Holding a Fleshlight for a Friend

Everyone in this story is 18.

Chapter 1: The Gift

On the day my brother left for college, he came to me and gave me a box of "goodies". He made me swear not to tell Mom and Dad, and not to open it until I was alone later. He added, "There will be plenty of this when I get to college."

I accepted hesitantly, hoping maybe it was weed.

That night I found that it contained a nice fleshlight and some lube. Wow.

I immediately took it out and started having my fun with it. I pushed it right onto my hardening dick and found it to be even better than I had heard. I couldn't help but finish in probably fifteen seconds, and I went for round two immediately. I probably came four times that night, and barely slept. I cleaned it in the morning while I was in the shower, and hid it under my bed for safe keeping. I love my brother, I remember thinking to myself.

My buddy Zayne came over the next day to work on a school project, and then just hung out like we often did. We were both eighteen. We had been friends since we were kids. Parents were gone so we had the house to ourselves. This is when we would normally get up to some nonsense, maybe some risque websites and stuff like that, but nothing too wild.

Eventually, I told him about the gift. His eyes lit up and he laughed way harder than I expected. "Your brother gave you that? Dude, that's awesome."

He got quiet for a moment, then surprised me by asking if he could try it. I was thrown but eventually shrugged and said, "Go for it." He disappeared into the bathroom for a couple minutes, and I couldn't avoid hearing the telltale sounds of its vigorous use, squishy and sloshing. Be he came back looking a little flustered.

"How was it?" I asked.

"I couldn't really get it right," he said.

I was shocked. "There's no wrong way, man. Just stick it in."

"I thought you were supposed to go at it like it's a girl," he said, sort of exasperated, "isn't supposed to be just as good as pussy?"

"Just crank it, bro," I said, losing interest in his disappointment.

"Nah, like the whole thing is it's supposed to be like actually putting it in a girl, but I can't get it to hold still where I need it!"

The frustration on his face elicited some empathy from me. "Ah, ok. Well it's not a girl, it's just a sloppy silicone pussy. Personally I love it."

"Can you...hold it for me?"

I was confused for a second, before it dawned on me what he was asking.

"You mean while you use it?" I asked, shocked.

"Nevermind," he said, looking red and embarrassed.

I didn't say anything. We continued to work on the school project for a couple hours, but he seemed off, disappointed. We ended up talking about how weird it is growing up, how confusing it can be navigating relationships and expectations. It turned into a kind of unexpected heart-to-heart, which wasn't super normal for us.

Of course we moved on to chatting about girls from school, and what we would do to them if we had the chance. The brief thrill ended when he pointed out that he's far too shy to talk to girls.

I was tired of him wallowing in this weird self-pity, so I decided to be a good bro. "Hey dude... if you wanna use the thing... I'll hold it for you."

His eyes lit up. "Really??"

"Yeah, sure, here." I grabbed it from where I had it stowed away, and handed him the bottle of lube. "Go nuts."

I could already see him tenting his pants, so I closed my eyes and held out the toy in both hands, bracing for him to start going at it. If he was anything like me, it wouldn't take long anyway.

I heard his pants unbuckle and unzip, then the bottle cap snap open, then some squishy rubbing as he applied the lube. Then, I flinched when I felt wet skin touch my hand.

"Woops," he said, as he adjusted his aim, and I felt him pushing against the toy in my hand. He was in. To my surprise, he started out rough as hell. He was really dead set on treating this thing mercilessly. I couldn't even hold it straight from this angle.

"Hold it still!" he said, laughing.

"I can't, you're going crazy on it!" I shouted, my eyes still closed

"Hold it against yourself, then," he said.

I opened my eyes to give him a what the fuck face, and I almost forgot he was nude in front of me. The surreal sensation of abruptly seeing your best friend naked hit me like a thunderbolt. The main surprise was that his tool was the size of a fucking baseball bat.

"What the fuck..." I said, not even loudly, just in shock.

"What?" he replied.

"You're huge, dude. That's like...bigger than an elephant."

"Really?"

"Yeah, I think so. Haven't you seen a dick before?"

"Not hard, except in porn. They're not far off."

"Yeah, porn stars are bigger than average, dude."

"Oh, yeah, that makes sense."

He pulled all the way out of the toy, and the length of this thing was shocking. It looked like an arm.

--[]--

I grabbed it and laid down on the bed, holding it steady against my chest like a makeshift assistant in a very bizarre science experiment. He stepped closer, hesitating for a second, then knelt down so we were almost face to face. I wasn't expecting him to be that close. Like, I could feel his breath on my cheek. My eyes darted to his, and for a second, neither of us said anything.

"Just, uh, hold it still," he said, trying to sound casual but clearly a little nervous.

"Yeah, yeah, I got it," I muttered, eyes looking anywhere but directly at him. The whole situation was so awkward it looped back around to feeling kind of funny.

He adjusted slightly, and we both burst out laughing at the sheer absurdity of it all. The tension broke, and that weird closeness, while still definitely weird, didn't feel as uncomfortable as I would've guessed.

Zayne was focused, adjusting himself slightly as he got ready. I tried to play it cool, but the image was burned into my brain. It was one of those unexpected realizations you're not quite sure what to do with in the moment, so you just file it away and move on.

Instead of going at it from across the bed, Zayne surprised me by stepping over and straddling my face directly, like, right over me. He positioned the toy against his hips, and as he leaned in to get the angle right, his hips dipped lower than I expected. Suddenly, I found myself nose-to-shaft with him, and his balls were literally plopped onto my forehead.

I burst out laughing, and mumbled around his cock literally pushing against my face, "Bro! Personal space!"

He laughed too, a little flushed. "Sorry, it's just easier this way."

"Whatever," I said, still holding the toy steady, trying not to laugh again. "Just don't teabag me."

It was dumb and funny and exactly the kind of thing that would've mortified us a year ago, but now just felt like part of this strange trust exercise in being young and too open with your best friend.

And honestly? I didn't mind. It was fun in the weirdest, most unexpected way.

But in that moment, while I was doing my best to hold it steady and pretend like I wasn't pressed against my best friend's cock, I started to feel something unexpected myself. A kind of flutter in my stomach, nerves maybe, or just the sheer weirdness of the situation catching up with me. But it wasn't just ants in my pants. There was a strange kind of excitement too, like my body didn't quite know what to make of the closeness, the heat, the sound of our laughter mixing with the most surreal circumstance imaginable. His dick started sloshing in and out of the toy in my face, and his sweaty balls coated me with his musk. His big dick was a masculine checkmate. He was more than me, in some ethereal way.

I started to feel a bit of pressure in my pants. Not exactly a full-on reaction, but enough to notice. Enough to wonder.

It didn't freak me out. It actually kind of added to the hilarity of it all. Just one more thing I didn't expect, another notch on the 'what is even happening' scale of horny era chaos.

Then, without warning, Zayne really got into it. He started picking up the pace, getting more comfortable, more intense, like he was trying to prove something to the toy, or maybe just to himself. His hands slid instinctively to my sides, gripping my abdomen to steady himself, which made me laugh through my nose in surprise.

"Whoa, dude! Easy on the abs," I joked, trying not to drop the thing.

He grinned but didn't slow down. And, yeah, his enthusiasm meant his hips were moving more wildly, and his balls? They were definitely making way more contact with my face. Over and over, along with his shaft, they were rubbing my skin raw and indelibly marking my brain with a reminder that he was the man here.

I stopped laughing. It was kind of thrilling in a strange way. Between the energy, and the sheer absurdity of the whole thing, as his pace increased toward orgasm, my body seemed to respond further. Not long after the laughter stopped, I was hard as a rock. Not just nerves, this felt different. Like this had, somehow, kind of become a hookup?

It was weird, sure, but not bad. There was something real underneath it all. Something new between us. He humped the toy wildly while I held it against my chest, and his most vulnerable body parts were literally pressed against my face.

When I thought it couldn't get any more gay, he reached down and grabbed my dick through my shorts. He didn't even stroke me. He just squeezed. And he squeezed hard.

I tensed up, holding the toy tightly on my body, and against the will of my brain, hips thrust and my cock pulsed, and released squirt after squirt of my load into my shorts. He held tightly while I throbbed in his fist, and the dark spot grew on my shorts above his hand. He never stopped humping the toy, only going faster when he saw my body's reaction.

At one point, my hand slipped and I noticed something. He was so long, his large tip actually poked through the far end of the toy when he pushed in all the way.

"Bro, you're breaking the laws of physics!" I said, stunned.

And then he finally finished, his body performing the slow, arhythmic jerking dance of the male in orgasm, the tip of his engorged rod was fully through the other end of the toy, and it got all over me. It coated my clothes, my crotch, my stomach. He pulled out slowly, and I finally saw the light of day again.

He cracked a smile and nodded. It was one of those odd, young moments that felt strange at the time, but years later, you realize it was just part of growing up and learning how to trust people with your awkwardness.

It didn't get weird, not really. He was grateful, I was curious, and we both got a little better at laughing at ourselves. And that's what made it a memory worth holding onto: not the object, but the unexpected closeness and honesty it sparked.

My mind was shot after such a strange experience, and I just quietly wiped myself off with a towel, while he sat there letting his monster hog hang down, resting on the carpet between his legs, still naked on his lower half.

After a minute of silence, he looked at me. "Are you mad at me?"

I looked at him confused, "No, dude, why?"

"I don't know... I just nutted all over you."

"Well, don't tell anyone, and we're cool," I said, "you can hold it for me next time. And then some."

He looked at me for a moment like I was speaking another language, then his jaw dropped with realization.