Sizing

I have one interest, and one interest only.

I’ve always had very good spatial awareness. Parallel parking? Do it with my eyes closed, for a challenge. All right, one eye closed, don’t fancy losing my no claims discount.

My Da used to call me his little pack rat. He’d get me to help him pack his suitcase for work trips, forgetting that he’d have to pack it hisself for his return journey. We’d end up on a video call with me giving him instructions and him tearing his hair out but between us, we’d work it out. I still miss him.

So I suppose it’s not surprising that I now earn my living as a sizer and fitter at the lingerie shop that opened three months ago off the High Street.

Sizer? I barely know ‘er!

Sorry.

But aye, you know the place. The one that looks like it should sell wedding gowns “by appointment only”, given the exclusive decor but really, anyone with enough cash is welcome. Now that I think about it, a fair few are brides-to-be and their wedding parties, so maybe I weren’t far off.

Lisa weren’t keen on hiring me, not at first. A man, sizing and fitting bras? She’d be laughed out of business! The police would be called! She was convinced though, when at my interview, I pointed out that she was wearing the wrong size.

“What, just by looking?”

“Yes ma’am. Not that I were looking, not like that you know...”

What can I say. I know an ill-fitting bra when I see one, even if it’s under clothes.

“So what size should I be wearing then?”

“Well I can tell it’s off, but I can’t tell what it should be. I’d need to see what I’m fitting afore I fit it, don’t I?”

She claps her hands over her bosom, a gasp of outrage echoing through the empty shop. “Cheeky!”

I shrugged. It’s true, it is. She thought about it, then turned away. So did I, out of politeness, and after some rustling and swearing, she handed me her bra. “Here’s what I had on. If you can find me what you think the right size is, I’ll take you on a 2 week probation.”

I took the bra. It were a nice one: lilac, delicate lace, underwire. Nothing special, but beautiful and well made. Still warm to the touch. And fragrant, even without me holding my nose to it. She jerked her head. “Take your pick, all our stock’s on the shop floor. You have ten minutes”.

I looked at her chest for a moment. She’d covered back up, but I could see enough to get a good idea. I looked back up at her face, a faint blush tinting her cheeks pink. I suppose a young man openly staring at her chest while holding her bra in his hand is objectively an embarrassing experience for anyone. “Right you are ma’am.”

I didn’t need the ten. Two minutes later I was back at her desk. “Try this one. And if I may, the colour matches your blouse better. You could leave the top couple of buttons undone, show off this elegant trim, it’d be very nice. Very nice indeed.” I grimaced. “Soz. Mam always said I were the sort to filter my mouth by stuffing my foot in.”

“No, you’re all right. Give it here.”

She took it from me, then turned away again. Did this place not have fitting rooms? I wondered, as I turned back. I noticed that there were mirrors along the walls, and in them, I could see her as she unbuttoned her blouse. I gulped. “Wait, I’ve given you the wrong size!”

“What? How do you...?” and then she remembered the mirrors. Our faces now a matching shade of red, she wordlessly handed me the bra, an arm over her breasts. I took it and dashed back to the rack, swapping it for the right one. “Here, I’m sorry, I didn’t mean to look, I just didn’t want you to think I don’t know what I’m talking about because I do, not just bras specifically but I can size anything and-” she held a hand up to stop me verbally shitting all over her, and took the bra. “-aye. Try it.”

This time, she didn’t bother turning, but I did. Mam raised a gentleman, she did, and I know my right from my left.

Lisa cleared her throat and I turned back. “It’s...it’s so much more comfortable,” she murmured. Not sure why she sounded so surprised. I told her, I did. “Feels almost like I haven’t got anything on. And you were right about the colour.” She looked at herself in the mirror again, admiring the look before offering me her hand. “Start on Saturday?”

That’s how I ended up here. Word hasn’t really spread about me. Nobody wants to admit that they’ve had a nice young lad eye them up and tell them what to wear. But I do have a small reputation building amongst those in the know, and Lisa’s a shrewd one, she is. She knows her business. She put me to work learning every single size for every single model we carry, and I took to it like a duck to the wet stuff.

It got to the point where I knew some of our regulars well enough that I could tell them which bras to wear at which point of their monthlies. People always forget that size changes in response to hormones, fitness level, life events...aye. I’ve been researching. In short, I know my work, and I’m happy. And as long as she’s making money, so’s Lisa.

And then one day while I’m stacking boxes in the back, I hear her gasp. She sticks her head in and hisses at me. “Fashion royalty in the house - Jessy in a Dressy just walked in!”

“Jessy in a what?” She doesn’t answer, just lobs her mobile at me before disappearing out front again. I catch it easily in my off hand. Good spatial awareness, I’m telling you. Underrated superpower.

I looked at it. JessyInADressy. Fashion influencer. I scroll a bit. A million followers. Queen of every look - classy escort, girl next door, hot librarian - looks like she can pull anything off. All while wearing the wrong size bra.

“I’ve heard you have a miracle bra sizer here...” I hear from the shop front. That’s my cue. I straighten my tie, wipe my hands clean, and walk out.

“That’s right, and here he is!” Lisa beams cheerily.

“But he’s...a he!”

“A most astute observation, ma’am.” I reply drily. Snooty customer, snooty me.

“We’re an equal opportunities employer,” Lisa hurriedly interjects. She knows I’m getting a bit tired of having my gender thrown at my face when I’m just trying to do my job.

“How do I know he’s not deriving some sort of...sexual gratification from this?”

“Ma’am, in a world with a billion different fetishes, how do you know Lisa here isn’t getting sexual gratification from you being a roaring bitch to someone you’ve just met?” I ask. Mam was wrong about my filter. That was very restrained of me.

“What? You...” JessyInADressy turns red, then purple. I’m fascinated at the various shades she’s displaying, and mentally catalogue them against the colours we stock.

And then she surprises me. She bursts out laughing.

“Okay, miracle worker. Tell me what size I should be wearing.”

“Can’t. Need to see ‘em first.” I’m still annoyed. Lisa nudges me gently with an elbow, and I let go of some of it. Some. She nudges me again, less gently this time. All right Lisa, all right.

I can almost hear the gears turning in JessyInADressy’s head.

“You want me to...and then you’ll...” I nod.

“I’ll do it...if you undress too. So that I’ll know the moment you get turned on.”

This is new. I turn to look at Lisa. She had a pleading look in her eye. I can tell, even behind the pound signs. She won’t hold it against me if I say no, I know that. We have a nice mutual respect thing going on. But Mam always says to try everything once. It’s how I know I don’t like how cardboard tastes.

“It’s very unprofessional ma’am, but all right. You show me yours, I’ll show you mine, and Lisa here will be our chaperone to make sure there won’t be any funny business.”

Lisa locks the door and puts the “Closed” sign on, shutting the blinds as she goes. JessyInADressy doesn’t waste any time. She’s in a light sundress, and she simply slips the spaghetti straps off her shoulders, allowing it to fall to her feet and stepping out of it. She has on a matching pair of sky blue panties and bra. A little bow on the front of the panties, and the same between the bra cups. Very chic, very demure.

“All the way ma’am, or just the bottom?” I ask politely. She grins impishly and draws a circle with her index finger, indicating the full nude option. Lisa better be giving me a big bonus on this.

I take a bit longer to undress than she did, removing first my tie, then my jacket, which Lisa takes from me. I unbutton my shirt and take that off too. I’m not one of them built lads, but lingerie gets delivered in surprisingly heavy boxes, and so I have a reasonable physique.

I think about it, and take my shoes and socks off. “Nothing worse on the eyes than a naked man in shoes and socks,” I murmur, and JessyInADressy nods, impressed at my level of sartorial expertise. I tell you. Research.

I take my trousers off, and all that is left is my boxer shorts. No tent in sight. I catch JessyInADressy’s eye and ask, “On three?”

She laughs and reaches behind herself to unhook her bra, which is at least a couple of inches too small in the band. I think she’s actually enjoying this.

“One, two, three!” she calls out, and leans forward, dropping her bra at the same time my boxers fall. I should probably have thought about the unfairness of me going fully nude while she keeps her knickers on, but oh well. I’m here to do a job and it’s up top I’m sizing her, not down below.

Both garments hit the dark, hardwood floors with a soft plap. She and Lisa both look downwards. Maybe they want to be sizers too.

Flaccid. And, as much as I hate to admit it, looking rather shrivelled. I’m a grower, not a shower, and Lisa keeps the air conditioning right down low in summer, which I’m normally grateful for on account of the tie and jacket, but not right now.

I notice JessyInADressy’s nipples are also feeling the effect of this as they begin to stiffen, little goose bumps marking her flawless skin. Afore anyone thinks I’m a pervert, bear in mind that the whole point of this exercise is for me to examine what I’m fitting. The fact they grow to twice their size when she’s cold is a relevant piece of information.

“I can’t decide if I should be relieved or offended!” she says, as she keeps looking down. I can’t decide either.

I ignore her, continuing to evaluate her breasts. The poor things have marks on them from how tight the bra was. I reach out and touch the side of one gently with my fingertips. “See these marks? Your band is too small.” I bend and pick her bra up to look at the label, letting out a low whistle. “28C? Sounds good, it does, but you’re more a 30, 32B. Depends on the make.”

She gasps as I touch her, which I barely notice. I’m in work mode. I go over to the racks, and pick out one that’s in the same shade of blue. “Try this one, you’ve got a good eye for colour, so no need to change that.”

My cock flops about as I walk and I try to ignore it, though I notice Lisa’s eyes have barely gone above waist level since I got naked. So much for mutual respect. I’m going to have to have a word. I’m a professional.

JessyInADressy tries the bra on, checks herself out in the mirror. She cups her boobs with her hands. Don’t ask me why, surely that’s the bra’s job.

“That’s...bloody amazing, how did you do it?”

“Miracle worker, aren’t I?”

The rest of the afternoon continues like this, me selecting bras for her, and she even gets me to help her put some of the more complex pieces on. She asks my opinion on a couple of things, and actually seems to appreciate my advice, and the cash register in Lisa’s head makes dinging noises each time the yes pile on the counter grows.

She serves some wine and cheese and crackers that she keeps in the office for bridal parties. JessyInADressy seems to enjoy the attention. I decline - it’s Lancashire cheese, for crying out loud. Everyone knows Wensleydale’s- all I can say is, good thing she doesn’t run a cheese shop. Even I wouldn’t be able to help her.

Throughout the entire occasion, I stay soft, even when she “accidentally” grazes my scrotum with her fingers while I’m helping her take off a bra with a particularly stubborn catch that got tangled in her hair. I’m working.

Then we’re finally done, and she pays for her purchases, adding a massive tip for me. Lisa bags up her purchases in one of the heavy paper bags, the ones that look proper class in all white with a splash of red in the corner.

JessyInADressy puts her dress back on. She doesn’t bother with a bra. After all that work. Tch.

Once her dress is on, she slips her panties off, and places them in my hand. I notice the gusset is rather damp. “I always like to match,” she whispers in my ear, kissing me on the cheek and thanking me for being a gentleman. “I’ve left my number at the desk. If you ever want to meet up unchaperoned...call me.”

And with that, she breezes out and is gone, stopping only to take a quick selfie of herself in front of the store. I see the picture on her grid later that night, and spot that in the background, barely noticeable, you can just about see me getting dressed. If you didn’t know better, you’d think my bare arse in the corner was just light reflecting off the shopfront glass.

We now take appointments for the JessyInADressy Fitting Experience. It’s surprisingly popular, enough so that Lisa’s thinking of branching out into sex toys. She reckons I might be able to help with selling those too, although she hasn’t quite told me how. I didn’t think they were sized.

What does the fitting experience include? Well, you’ll have to book yourself in for one to find out, won’t you?

*****

Enjoyed the story? Got questions? Want to get in on a book-club style discussion about any of my writing, or got a piece from someone else you want to discuss? Click here to drop into my subscriber chat! I can’t promise cheese and wine, but I will be glad for a natter.