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Thanks to Francois for the proofreading and tips!
Chapter 4 - Shopping Trip
Joey was waiting outside school to pick me up, punctual as ever. "Jump in, runt."
Halfway to the mall, he pulled over, and turned the car off.
"So, you know we need to like... talk about that, right? Like more than just me teasing you a bit?"
"Do we need to? Let's not and just say we did, please?
"Sorry, kiddo. Kinda one of those big talks that needs to happen. Number one, those weren't your undies, so who do they belong to? Are you being a perv and stealing people's boxers? Number two, and I don't care either way, really, but are you gay? Bi? Or just a weirdo?"
"The first one, no I'm not stealing anyone's boxers, they were like, given to me I guess - they're from this guy I li- I know from school. And the other thing, I don't know."
I was frowning, almost scowling, head down. It was hard to have to talk about this without... someone who gets it, who's going through it. And for it to be because of what he'd seen, me huffing on a guy's used fucking trunks?
"I don't know if I'm like... I don't know. I just know I like Lachlan is all. And some other boys. But maybe some girls. Sorry."
I had tears in my eyes and my hands were balled into tight, red fists. I wasn't crying, not really, but my tears had started to roll down my face. I wasn't sad; it had just been so hard to say, but now that I had told Joey, it felt like a weight lifted.
"You don't need to be sorry."
He put an arm around me and pulled me into a sideways hug.
"I told you I don't care either way, there's nothing wrong with you liking this Lachlan boy, or liking other boys, or maybe liking girls. Does Lachlan like you back?"
"I think so, I don't know."
"Well does he treat you nice?"
I nodded, unsure how true that had actually been, and he resumed the questioning.
"Well, whatever the case, just make sure you're being careful, alright? And I don't just mean be careful not to fall too hard too fast, I mean like, are yous using protection? Condoms? Just because you can't get pregnant, doesn't mean you can't get sick. STD's?
"Dude, shut up, that's so gross to talk about with you!"
"I'm just saying, make sure you use them if anything does happen, you can borrow some of mine or I can buy you a box of minis if you don't fit mine."
He winked and nudged me with his arm, laughing, as he turned the ignition and pulled back onto the road. The rest of the drive to the mall was light-hearted, filled with chatter of all sorts. I think he knew that conversation had been a bit heavy for me and wanted to keep everything else as light as possible, and it worked. I felt far better having let another person in on it all, and he made things feel normal still, instead of weird like I'd thought he might.
After arriving and getting something to eat from the food-court, I followed Joey into two different clothing stores, as he bought himself several different shirts and pants, making sure to make several different variations of 'do you think my ass looks hot in these? You'd know best' jokes as he tried the pants on. Then it came time for the underwear.
"So you're after trunks, or boxer-briefs?" He asked simply, as if I really knew what the difference was. He saw my somewhat confused look, and explained.
"Trunks come down to about here" he brought a finger to about an inch or two below his mid thigh, and then continued: "Boxer-briefs only come to about here." His finger now sat about two to three inches above mid thigh, before he said "Never mind, we'll get you some of both, I'll help you expand your wardrobe a little, we'll get you a few new styles to try."
He tousled my hair, and then we went into the underwear section. I had to keep my eyes moving, or looking up, scared that if I stopped, I'd look like I was staring at one of the hot men in nothing but their underwear on the packaging and advertising all around us. Of course, I wanted to stare, but felt now was not the time to do so.
"So what size are you? Did you fit that Lachlan boys boxers?"
I started going red and he continued: "I knew you'd try them on, you freak. It's ok, kid, you're allowed to try out gross stuff like that. God knows I've done my share of shit people would think was gross, and enjoyed plenty of it too. You look like a medium, maybe a small."
He grabbed a few pairs of different colours, sizes, and lengths off the rack, and headed to the changing room. I followed along, wondering what we were going there for.
"Really? Like what?" I probed, unsure what I might hear, or if he'd tell me anything.
"Well, one of my exes, you remember Jessica? You'll get a kick out of this one, she liked her ass being eaten, but she liked eating mine even more. It's pretty good, trust me, you'll enjoy it."
My face was completely red now as we stood outside the changing room lockers, and I looked around to see who could hear him, hoping for no one. That was when Lachlan came out of a changing room, two shirts in his hand, and a grin on his face.
"You will, will you?" He smirked and winked at me, and my face became as hot as an ember.
"Hey, Lachlan. What - um - what are you doing here?"
"Well I bumped into Eric today, we talked a bit, he told me how jealous you were getting over this imaginary girl you made up, and how you'd be here after school and I should talk to you, so.. here I am."
"So you're the famous boxer-briefs Lachlan, eh? Heard.. well.. not enough about you. I'm Joey, Andy's older brother."
He held out a hand, and Lachlan shook it. For some reason he almost looked nervous. Usually he always seemed confident, but he had gone somewhat red in his face for once. It was hot seeing him blush, and I could only imagine it was at some other guy knowing about him giving me his underwear.
"Nice to meet you, sir. Yeah, I'm Lachlan." He shook Joey's hand, and his eyes travelled up Joey's tall frame once more before climbing back down and settling at his large hands, unexpectedly soft.
"Anyway, you two can look after yourselves for five minutes, I wanna grab a couple t-shirts. Andy, hop in the changing room and see what size you are."
"You're not allowed to try the underwear on in the store though!" I whispered in a stressed tone.
"So? They don't have cameras in there; I'm not wasting money buying two of every pair."
With that he wandered off into the racking, leaving us here alone, his arm with shirts on it, my hand holding several pairs of underwear.
"Andy, you never told me your brother was so hot! I couldn't help from blushing when I shook his hand..."
"I noticed that" I replied, then he continued.
"So, the jealousy thing, huh? You thought I was hooking up with some girl from school? Upset over a rumour that I'd done something with some girl last night?"
I nodded and apologized, but he rested a hand on my hip and lowered his voice a bit, leaning closer to me.
"You don't need to be jealous. The only person I was with yesterday was you, and my Mum. I was messaging you last night, remember? You really think I'd be messaging you while I was balls-deep in someone's throat? Actually, scratch that, that sounds kinda hot. But still... you don't need to worry. I like you, Andy. I think you're sweet and cute and funny. I think we have a connection, and I hope you do, too?"
I nodded my head, and he said "Good. You don't talk much, but we'll work on that. Gotta get that confidence up sp you can stand in your own voice and feel good to say what you think. Anyway, aren't you meant to be trying those on? He directed me into a stall, and I locked it from inside.
"I don't even know what these are meant to fit me like?"
I said from behind my locked door, dropping my uniform shorts to the floor, and sliding my loose boxer shirts down my legs.
"Try some on, and I'll tell you if they fit right or not. Show me what the ones you're wearing now are like."
I un-snibbed the door to let him in and quickly re-snibbed it behind him, fearful someone else might see me with no pants on. He looked me up and down, twice, and I felt sweat begin on my forehead. He knelt down to one knee, looked up at me, face only inches from my tightly held package, and said "May I?"
He put his hand on my thigh, and it felt like electricity, feeling his skin touch mine. He put two fingers up to the elastic band at the bottom of the underwear, and rested them there. "These look really good on you, I can see in the mirror behind you how well they frame your ass, and the way they hold your package is nice, shows it off really well, but I think these are a size too small for you." He slipped the two fingers under the elastic, so that they made contact with my skin, as the underwear held them tightly against my flesh.
"This here, should be comfortable, not tight. You don't want it cutting into your leg, man, you want the elastic to sit confortably on your skin and go tight when pulled, not when there's two fingers flat in between you and them."
He stood back up, and placed his hands on my hips, and this time dipped both his thumbs into the waistband of them, also decently tight.
"See? They shouldn't almost be leaving a white mark around your waist; that's only because they're overly tight on you. Try the mediums on."
I stared at him, trying my best not to think about the erection that was between us since his hands first touched my thigh. He kept his eyes on mine, hands still on my hips, and said again "May I?"
I nodded my head, and closed my eyes as he leaned in and kissed me on the lips. It was soft, but almost desperate, and I felt that sense of urgency reciprocated inside of me. My hands came to his shoulders as our lips broke apart for a breath before colliding once again, his left hand sliding up from my waist, under my top to feel my body. I gasped as he glided up my skin, sensitive and reactive, almost ticklish but in a pleasurable way. His lips broke from mine and began kissing along my jaw onto my throat, down along my neck. My hands clutched at him and pulled our hips together hard, both of us softly rutting against one another, as his lips began caressing my neck, my breath becoming ragged almost immediately from that.
"You like that?" He whispered gruffly in my ear, hand grabbing my hip firmly, as he returned to kissing my neck with more vigour. My breaths were coming faster and harder, and I had my face buried in his shoulder, trying hard to suppress my moans and whimpers. Suddenly and without warning, I felt my whole body stiffen against him, and my nails dig against his back, a wet spot quickly forming inside of the underwear a size too small for me.
We stood still, silently breathing for another minute before I could even lift my head off his shoulder. By now the wet in the underpants had gone cold, and become uncomfortable.
"I-I'm really sorry, I didn't mean to-"
He cut me off, shushing me.
"Shh, it's ok, cutie. It just means you can't put those back on the shelf. Here, let me help you out of them."
Thank you for reading this far, hopefully if I get some good feedback, then part 5 will be up within a few weeks!
Again, if you enjoyed my story, flick me an email on discord3231@gmail.com and tell me what you thought of it. Even if you don't enjoy the story, still email me, I can take constructive criticism if you're cute!