Speedo Shopping Humiliation

I'd been dreading this day for some time.

It was the last week of Summer vacation and I was about to start my final year of high school. My name is Simon and I've just turned eighteen years-old. I've been a swimmer since junior high, not the best on the team, in fact probably one of the weaker swimmers. Juniors are frequently called ahead of me to race, and I spend most of my time on the bench, but my family have money, and contributed a lot of charitable donations to my exclusive private school, and so the Principle pulled some strings and, much to the swim coach's consternation, ensured that I always have a spot on the team. If coach ever gives me shit about my attitude, I just tell him my family paid for the fucking pool.

"Come on Simon," my mom yelled. "Time to go to the mall!"

"Just a minute!" I yelled.

We were about to set off to the sports store to pick up my new Speedo. My mom insisted that she come with me to help pick out a suit; even at my age she still didn't trust me to get the right kind on my own. Needless to say, my mom could be a real bitch, and we didn't exactly see eye-to-eye.

"Simon!"

"Dammit mom! Just a minute!" I shouted back down the stairs. "Damn," I murmured to myself. "Fucking bitch..."

I checked myself out in my bedroom mirror. Boyish face, pretty cute, or so I've been told. Short brown hair, medium height, and a good body with a fair amount of shape to it. An average teenager, in most respects at least. There was just one particular area in which I was only too aware that I was not average, and this was the source of my reluctance to venture out and model different sizes of speedos for my mom.

---

"Right, let's see... where's the children's section?"

"Mom, we don't need to go to the kids sec-"

"Ah, here's someone we can ask! Miss, I need to buy my son a new speedo suit for his swim team, can you tell me where they're stored?"

The pretty young sales assistant smiled at me and nodded her understanding. She seemed to get the situation and quietly acknowledged my discomfort with a sympathetic smile. I could tell right away that this chick was definitely into me, so I smiled back, rolling my eyes at my mother.

"Sure thing ma'am, the men's swim briefs are in the section just over there-"

"Oh no," interrupted my mom. "I mean the children's section! Simon wears boy sized speedos."

The sales assistant couldn't help but smile, looking down at her feet in an attempt to hide her obvious amusement.

"Mom!" I started to protest, my voice suddenly sounding high and whiny. "Can't we go to the adult section this time? I don't even think they'll have speedos in my waist size in the kids' department!"

"But dear... we tried that last year and you simply don't... well, 'fit' into men's ones."

"Mo-om!" I hissed. "Ple-ease?!"

"Oh very well! If it'll make you happy..."

We walked over to where the men's swimming costumes were displayed, and I grabbed a pair of royal blue (our team color) speedos in my waist size, 32.

"Now you go ahead and try those on and then come out and show me how they fit."

"Do I really still have to show you?"

"Yes Simon, I'm paying for these, and besides the whole school will see you wearing them at swim meets."

"But we're in a store."

"Why do you have to make this so difficult? Just do as I say."

I grumbled quietly as I stalked over to the changing booth, drawing the curtain behind me. Once safely inside I examined the soft, shiny speedo, holding it up for inspection. I was immediately struck by how the pouch in front of the men's ones seemed so much bigger than on my usual boys' speedos. Just looking at it make me feel, well, intimidated. I could feel my cock and balls retracting slightly and I gave them a quick tug through my jeans before placing the speedo on the little chair and struggling out of my t-shirt and jeans.

I stood there in my white CK briefs in front of the mirror for a moment before sighing and slipping off my underwear, the familiar site of my tiny, cut penis and small balls failed to instill in me much confidence, nor did the meagre dusting of public hair which had finally begun to grow just above my penis the previous year. (Yes, I had gone though almost all of high school without any pubes - most of my classmates had got theirs in middle school.) I stepped into the speedo and pulled it up around my waist. Straight away I could see that, quite simply, I did not even come close to filling out the front of the men's speedos. The material in front was limp and baggy, and I couldn't even make out the shape of my little penis, which sat atop my tight ballsack and poked out at around 2" soft. I turned around and tried to find a more flattering angle, but no matter the perspective my profile didn't even show the outline of a bulge.

"Simon? Come on out so I can see you."

"Aw, mom! Seriously?"

"Yes Simon. Right now." She was obviously losing patience.

Reluctantly I pulled the curtain back, hovering nervously.

"Well come on out so I can see you."

I stepped out into the main store area, acutely aware of all the people around us, many now staring and smirking at the sight of an otherwise normal and athletic 18 year-old boy wearing a pair of baggy speedos which served only to highlight his obvious and distinct lack of manhood.

"So, uh, what do you think m-mom?" I stammered.

She looked down at my crotch, at the loose fabric in the front of the speedo, the light blue color hiding nothing, and she let out a loud and exasperated sigh.

"I think you've just wasted both our time Simon." She angled her head to get a better look at my crotch, tutting disdainfully. "I mean you must have known that you haven't grown any down there this year." She looked up and caught my eye. "I know full well that you measure it before playing with yourself every night, so why bother pretending you can fit into men's speedos when you're so obviously still just a boy down there?"

I was stunned, totally taken aback by her words. When she reached out and tugged at the baggy front of the speedo I jumped back.

"What are you talking about? I don't measure it, I don't play with myself!" I suddenly checked the volume of my voice as a couple of nearby teenage boys, younger than me and both, incidentally, shopping for men's size speedos, snickered at our confrontation, their eyes guided down towards my crotch, causing more muffled laughter. "Dammit mom, why would you even say that?"

"Because why else would a teenage boy keep a measuring tape in his bedside drawer Simon? And don't kid yourself that I can't hear you through the walls every night. Like clockwork, I hear your little moans as you pull on it."

"That's not true!" I was turning red, looking around as more people took notice, pretending to be interested in the merchandise but obviously eavesdropping on this embarrassing scene between a mother and her teenage son.

"Oh don't lie, Simon. I never said anything before because, frankly, it's always over so fast. I even timed you a few times, and never more than a minute before that girly little whimper tells me you're finished! If a minute's all it takes then really you should be wearing little boys' speedos."

My jaw practically hit the floor. I couldn't believe she'd been listening to me jerking off every night! I knew I could be pretty loud sometimes, the feeling when I played with my little dick, stroking with thumb and two fingers, was too much not to moan a little, but dammit, she knew I couldn't help myself cumming so quickly as well...

"Now get back in that cubicle, we're going to the children's department and we're going to get you a pair that fit!"

"Mom!" I wailed, surrendering all dignity as my eyes started to water from this unexpected humiliation.

"NOW!"

My legs were weak, and I was struggling to hold back tears, all too aware of the dozen or so sets of eyes watching me as I walked back to the cubicle in my pathetically baggy speedos.

---

After getting dressed I found myself trailing behind my mother as she strode back towards the customer service desk. The same bemused sales clerk - the pretty young girl - was smiling awkwardly at our approach. She looked to be around 19 or 20, probably a college student. She had a kind of girl-next-door quality, brown hair, pretty face, full breasts and a perfectly curved ass in tight jeans.

"Yes, hello again," my mom smiled grimly. "So we tried the men's swim briefs and as I knew would be the case, my son simply can't hope to fill out the pouch properly in front. So we're going to have to try on a pair of child's speedos instead, isn't that right Simon?" She turned and looked at me, her accusing eyes full of scorn and disapproval.

"Umm, well yeah..." I mumbled.

"It's amazing to me, he's eighteen you know, so I suppose officially that makes him a man, but honestly, it's like he's still a little boy down there!" She said this loud enough for half the store to hear. "He only just started to grow public hair too if you can believe that!"

"Mom, please..." I whine, desperate for this whole episode to be over and done with.

"Quiet Simon, I'm talking to the girl."

The sales clerk didn't bother to hide her amusement this time, obviously finding much to smile about in this bratty, under-endowed high school jock who thought he could pretend to be a real man.

"It's okay, Simon, is it?" she asked. "Here, I'll take you guys over to the children's swimwear and I'm sure we'll get you a suit that you can, uh, 'fit' into."

We moved towards the rows of brightly colored little speedos, many adorned with cartoon characters, and it struck me then that the sales clerk had probably had to deal with many, many loudmouthed, overprivileged jocks in her line of work. I wondered just how much she was enjoying all this. I knew my mom was pissed at me, trying to 'make an example' of me, probably revenge for my constant bad attitude and arrogance, always using my family's money and influence to get whatever I wanted, but when the sales girl, whose name badge read 'Jennifer', pulled out a bright orange speedo obviously meant for an infant, and handed it to me with a grin, I suddenly knew she wasn't into me any more, at least as anything other than a torture victim.

"Just kidding!" she laughed, noticing the fear in my eyes. "What's your team color Simon?"

"B-blue..." I stammered.

"Over here, we've got navy, dark blue, and royal blue. Kids' sizes run by age in terms of the, uh, well the 'pouch' size, um, or design, but waist size is optional for each age bracket," she explained, playing it cool. "Do you think a '16-17 year-old' would be best? I mean you're eighteen, right?"

"Umm, yeah," I said, recovering slightly, managing to return her smile. "I'm eighteen, only just."

"Last year he had the 12-13 year-old's pouch design in a 30 inch waist," said my mother, suddenly talking over me like I wasn't even there. "I'm hoping we can at least move you up 14-15 year-old this year, Simon. And his team wear royal blue. Though frankly I would think a darker color would be less revealing, I mean those lighter ones don't hide anything." She suddenly looked from Jennifer down towards my crotch, and I was instantly reminded of a dozen swim meets which she'd attended; me in my light blue, little boy speedos, tiny bulge on full display, standing next to all the other guys sporting their impressive, hefty bulges. I guess she must have noticed then that I was smaller even than any of the juniors - she was quite right, the light blue speedos hid nothing, and I easily had by far the smallest package on the entire team. The guys didn't give me shit about it, but only because they knew that my father could easily have their father's fired.

So these two women were openly discussing the size of my junk right in front of me, and my own mother had just confessed to this hot girl, on my behalf, that I wore a speedo with a front pouch designed for a 12 year-old kid's dick! I couldn't think of how this could get any worse. I did my best to man-up and defend myself, thinking that maybe I could get out this with some dignity.

"Yeah, well mom, I'm a 32 inch waist now, and I think I'll take the 16-17 year-old ones. I am eighteen after all." I folded my arms, still trying to look tough despite the awkwardness of the whole situation.

Jennifer nodded, "Okay Simon, let's try that first." She selected a pair of bright blue speedos with '16-17 / 32' printed on the hanger. But my mom grabbed them before she could hand them over to me, holding them up to the light to inspect them.

"Oh come on now Simon," she said, laughing lightly. "Look at these, there's no way you could fill... I mean, they're obviously meant for a boy with a much bigger... well, you know!"

I snatched the speedo from my mom, feeling myself getting seriously pissed now. I was almost shaking with anger, desperate to prove myself not only to my bitch mother, but to the cute girl standing next to us.

"Shut-up mom! I'm trying these on!" And with that I stormed towards the children's changing cubicles, past a mother and her kid also picking up some swim briefs. I pushed past them into the changing booth and whipped the curtain closed behind me.

I stood for a moment, controlling my breathing, trying to get ahold of myself. I couldn't believe what a fucking bitch my mother was being, putting me through this. I wish I'd just done what she'd said and gotten the next size up, graduating to the 14-15 year-old speedos. I took a closer look at the 16-17 ones and groaned. My mom was right, the pouch looked huge! Obviously the designers had just figured for dumb parents getting these for their older teens who ought to be wearing adult ones anyway. I guess they looked a little smaller in front than the ones I'd tried on earlier, but still way too big for me to fill out with the meagre assets I was packing. Oh well, I thought.

I slipped off my t-shirt and jeans and kicked off my sneakers, once again dressed only in my tight little white briefs, looking at myself in the mirror. I wasn't as defined as the other swimmers on the team, but I had a flat stomach and some muscle on me, and my butt looked pretty good. I'd always been kind of arrogant around girls though, relying on my looks to get attention, but self-conscious about having such a small penis. I was still, as if it wasn't obvious, a total virgin. I'd made out with chicks, sure, squeezed their tits and even felt their sweet little cunts on occasion at various drunken basement parties. Once with this chick, Laura, I'd gotten so excited just from touching her boobs that I couldn't stop myself from cumming in my pants, suddenly having to get up and excuse myself, cleaning up in the bathroom and then sneaking home. I told my buds that I'd fucked her, of course, that she'd loved riding my cock, but then I'd had to quickly put it around that she was a dirty slut after she denied the whole thing. Thanks to my jock status she was pretty much shunned the rest of the year after that...

Hardly the cool, tough jock I pretended to be, instead always overcompensating for my tiny little boy dick by acting like a total jerk. Damn I was such a fucking loser...

I slid off my briefs now and stepped into the speedo, gently pulling it up first around my ass, then lifting the front over my cock and balls, looking at my reflection as I did so. To my utter dismay, the pouch in front sagged noticeably. I adjusted the drawstring, but it was already tightly tied, and although when I turned to the side, I could barely make out the shape of my little dick poking out, and the hint of my ballsack, I knew my mom was right - these speedos were meant for a guy with a much bigger dick.

"Simon? You ready?" I heard her saying now. I felt myself blushing.

"Uh, they fit fine mom, really I don't need to come out and show you!"

"C'mon Simon, I'm not buying them until I see you wearing them."

"Mo-om! Can't we just get them and get out of here?" I said, again sounding whiny and desperate, like a little kid who isn't getting what they want.

"Simon, now!"

And so I turned and slowly drew the curtain back, stepping sheepishly back into the children's department of the store.

"Um, The- they fit better than the... than the last ones," I said in a small voice, looking up hopefully at them both.

My mom and Jennifer looked me over, eyes resting on my crotch. Jennifer had raised both her eyebrows and was smiling, while my mom just shook her head.

"See Jennifer, this is what I was talking about. I just wish he'd drop this silly nonsense and let me decide what's best for him." She walked over and took a better look at me as I stood exposed in the space in front of the cubicles, my cheeks turning red.

"Well, yes, I suppose I see what you mean, but if they're what he wants..." Jennifer said, aiming for diplomacy, but quite obviously amused at the drooping fabric of the speedo pouch where a healthy teenage bulge ought to have been proudly standing out. "I mean you can kind of see his, um, y'know. I mean, kind of..."

I looked down now at my crotch and to my total shame I realized my little penis, frightened and nervous of all the attention it was getting from these two women, had shrunk up since I'd stepped out the changing cubicle, and now the speedo front was totally loose and baggy.

"It doesn't matter what he wants! He simply doesn't fit them. Really Simon, stop trying to pretend you're a big boy and let's just get you the same kind you had last year, at least you made some kind of... well, impression in those, however pitiful. Jennifer, would you please find us a pair of the 12-13 year-old speedos in a size 32 waist? Obviously Simon's not grown an inch, except on his waist," she said dismissively.

Up until she said this I'd been in a kind of numb daze, horribly aware of other shoppers casting glances at my baggy little speedos, some looking shocked, others smiling or pointing at the near-naked teenage boy sporting a visibly tiny bulge in his loose kids' speedos. But now my heart lurched and I suddenly came to with a sickening realization."

"But mom! Not those ones, can't I try on the others? The 14-15 ones? I'll definitely fill- uh, fit into those! Ple-ease! Mo-om?" More than ever I now sounded like a whiny, bratty little kid having a tantrum in front of his mom.

"Jesus, Simon... Now you even sound like a twelve year-old, will you just do as I-"

"It's okay, ma'am," Jennifer said. "I don't mind. If it makes him happy I'll go get both kinds, really I don't mind."

Jennifer walked over to where the competition suits for boys were displayed, leaving my mother and I standing outside the changing booths. I was busy examining my feet, quietly praying I'd at least fill out the 14-15 year-old's speedos enough that we could finally get out of here. My mom was still examining my minuscule bulge, kind of curiously, before she suddenly looked up and spoke.

"You know Simon," she said, her tone having softened a little. "I should say, it's okay that you want to touch yourself. I didn't mean to suggest you were wrong to do that. All boys do it, so I hear."

"Mom! Seriously? Please, this isn't the time!" I said, aware now of a group of passing teenage girls. They stopped and looked over at me, raising their hands to their mouths in laughter before scampering further into the store, giggling at the sight of my pathetic, baggy speedo.

"Oh, I'm sure it's fine Simon! I suppose I was just a little surprised that, well that you never seem to be able to last very long at all before... um, 'finishing'." She laughed now, looking down again at my crotch, making me feel absolutely tiny. "I know younger boys tend find it difficult because they get overexcited so easily, but by your age you should really be able to last more than 30 seconds, especially when it's only you who's touching it. I mean every night it's the same, you hardly last any time at all!"