A Tailored Release - Cover

A Tailored Release

Copyright© 2025 by JayFriday

Chapter 1

Erotica Sex Story: Chapter 1 - A young man is teased into losing control in his pants at a suit fitting.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Reluctant   Heterosexual   Fiction   Humiliation   Petting  

I eyed the racks full of fashionable clothing dubiously. Mannequins dressed in dapper suits. An assortment of ties, artfully arranged into a rainbow of color and texture. The store was, at least, well-heated; the weather had taken a turn overnight, and while it wasn’t blizzard conditions, it was quite cold, with a light snow falling.

“C’mon, Mom, can’t we ski first and do this after? You know I love skiing while it’s snowing.” I was aware that I sounded a little petulant, but I didn’t care.

She rolled her eyes. “No, Nathan, we cannot. If you had let me know prior to last night that you hadn’t packed appropriately, we’d have other options. If you had told me in the first place that you didn’t have an appropriate suit with you at college, I would have brought one. As it is, these are simply the consequences of your own actions. So I’m sorry you’re missing skiing this afternoon, but it’s hardly my fault.”

I sighed. My mother never made mistakes like these, but I hadn’t seemed to inherit her organized brain. Of course I hadn’t brought a suit with me to college, or thought to tell her I didn’t have a suit. Or thought at all about what I’d wear to my cousin’s wedding.

I mean, Mom usually took care of all that stuff.

The boutique was high end. But that was appropriate; the family wedding I was attending tomorrow was also high end. Most things here in Aspen were high end, if I was honest; it was that kind of mountain ski town. A limited, upscale set of options for the limited, upscale set of people who vacationed here.

And if you wanted a nice suit, ready in less than twenty four hours, your options were even more limited, evidently. And thus: me, following in my mother’s wake as she strode into the menswear boutique with the air of someone who expects to have her every whim immediately met.

Fortunately, as a result of it being high-end, there actually was a woman available to address my mother’s whims. The woman – probably about my own mother’s age, dressed fashionably, hair in a businesslike bun – immediately greeted her. “Hello, ma’am. My name’s Nancy; what brings you to us today?”

My mother rested a hand on my shoulder. “My son here needs a suit on short notice. It’s for a wedding tomorrow.”

The woman smiled and nodded. “Ah, you must be Mrs. Deveraux. You called ahead. Yes, that’ll be no problem.” I watched her assessing glance taken in my mother’s attire -- chic, in spite of it being February in the mountains. “The Crenshaw wedding, I assume?”

My mother sighed, the gale-force winds of her mood softened by Nancy’s even demeanor and clear competence. “Yes, that’s right. My sister’s son is getting married, and Nathan here needs a suit on short notice.”

“Very well. We can certainly help. Madison, will you come to the front, please?” The woman called over her shoulder, raising her voice only slightly. “We’ll get him measured and pick out something appropriate; our tailor can make rush alterations. You’re fortunate; our selection is actually pretty good right now, we ought to have several options that will work. There’ll only be a modest rush fee.”

My mother nodded, unfazed by fees. Money was never a problem for her. “Excellent, thank you. Now, I’m going to get lunch, Nathan. I’ll see you in an hour or so. Call if you’re done sooner.”

My mother, having successfully checked one more thing off the to-do list, gave me a firm nod, and marched out.

I might’ve felt awkward about the abruptness of her departure, but if I was honest, my attention had moved on from my mother and Nancy. I was watching the woman who was coming from the back of the store towards me.

She was short – much shorter than I was. Long black hair fell in straight lines framing an oval face; big eyes, a cute nose, full lips.

Admittedly, though, my eyes weren’t focused on her face; I was looking at the way she filled out the white button-down blouse and black slacks that seemed to be the boutique’s uniform. The blouse had buttons down the front, the top three of which were unbuttoned to reveal extremely full cleavage – two more buttons past what Nancy had unbuttoned.

In her defense, Madison’s figure looked like it made buttoning any additional buttons impossible, given how she filled out the blouse; her chest strained against the fabric.

Nancy was looking at me. “Madison, Nathan’s mother was the one who called ahead about a suit on short notice. Nathan, Madison here is one of our personal style consultants. She’ll be helping you today.”

“Um, thanks.” I pulled my attention off of Madison and nodded at Nancy. The whole situation was embarrassing. I was twenty-one; Madison couldn’t be much older. And yet, here I was, dropped off by my mom like a teenager at the mall. It was infantilizing.

“Right this way.” Madison’s voice was calm, reserved ... but I could see her give me an amused once-over before she turned around.

I followed her to a back room, watching the sway of her round ass in those tight slacks.

She led me back through the store, glancing over her shoulder at me. “So, do you actually go by Nathan, or is it Nate?”

I just barely managed to pull my eyes up quickly enough to avoid her catching me staring. Now that we were closer, I could see that her eyes were hazel, nearly an amber color. They were captivating; I was silent for a moment before I answered. “Uh, it is Nate, actually.”

She was really pretty. Maybe this wasn’t such a bad way to spend part of the day instead of skiing.

She led me to what must be a room for fitting and measuring. There was a chair in the middle of the room on a little platform; she gestured towards it.

“Have a seat. Can I get you something to drink while we do this? Coffee? A beer?”

I’d never been offered a beverage while shopping. Upscale was nice, sometimes.

I waffled for a moment. I suddenly cared a lot about making a good impression on Madison, and a beer was the more adult choice, I decided.

Although it wasn’t even noon. I could imagine my mother’s disapproval.

Which cemented the decision, obviously.

“Uh, a beer would be great, actually.”

She moved to a minifridge in the corner and pulled out a beer, handing it to me. It was ice cold – it felt great, in the warm store. I cracked it open and sipped.

Then she sat at a stool, facing me, and smiled; it was a polite, completely appropriate smile, although there was more of an edge to it than I expected, like she was about to say something sarcastic or clever.

Sitting facing each other, I could see she was indeed a few years older than me; in her late twenties, maybe. There was a confidence about her. “Now, Nate. First, I’ve got a few questions, and then you can try a few suits on you to make sure you like the color and cut.”

I shrugged. “Sounds good. I, uh ... I don’t really know much about formalwear.” And then I gave her a smile back. Mom gone, beer in hand, pretty girl talking to me. I was enjoying myself.

“Well, don’t worry, you’re in extremely capable hands with me. After we cover color and cut, we’ll dial in the fit by taking your measurements. I’ll pull one of our suits off the rack, we’ll measure and pin it up so it fits you, then we’ll send it all to the tailor and get you out of here; you can come back later on today to grab it. Shall we get started?” She leaned forward, all earnest enthusiasm.

I nodded. “Let’s do it.” I didn’t hear anything suggestive in the way she said you’re in extremely capable hands, but I liked the sound of it anyway.

And I certainly savored the additional view I had down her shirt. The blouse was fitted enough that it didn’t really fall away from her body much, but the angle gave me a better view of her cleavage, and I did get the hint of a brastrap – simple and nude in color, which somehow made it more tantalizing, like I was seeing something she hadn’t intended to show off.

She pulled out a little pad of paper. “Okay. First thing’s first. Tell me about this wedding. Any idea what the groom and groomsmen are wearing? Ties of a particular color, that sort of thing?”

That set me back. “Uh ... I think Steve is probably gonna be in a tux ... the groomsmen, um, I’m not sure...” I trailed off, at a loss.

She laughed. I liked her laugh – it was attractive, knowledgeable, worldy. But it was also the kind of laugh that immediately made you feel like you might be the butt of the joke. It gave me an instant spike of self-doubt. She probably saw all kinds of affluent clientele come through here, people who attended all kinds of fancy parties.

And they probably all knew what the groom was wearing.

In an instant, her amusement subsided; she must’ve seen the embarrassment on my face, perhaps realizing she taken it too far. She rolled her eyes and slapped my arm playfully. “I swear, men don’t pay attention to this stuff. You probably don’t know the bridesmaids colors either, do you?”

I shook my head ruefully. “Uh ... does that matter?”

Madison sighed. “Well, it depends. It probably won’t matter ... but if it does, it matters a lot. Let’s say they’re all wearing navy. And then let’s say I put you in a navy suit, and let’s say it just happens to be the exact same shade of navy as their dresses. And then your mother, who sounds like the demanding sort, asks why I dressed you like one of the bridesmaids. It would be good to avoid that.”

“Gotcha.” Her mention of my mother made me wince. Madison was exactly right.

Satisfied that she’d made her point, she continued. “And are you going solo or with a date?”

I winced again. Another sore point.

I was, as it happened, going with a plus one. Not a date, to be clear. My mother had made me invite a family friend, Grace.

Grace was the daughter of the family attorney, who would also be at the wedding. I’d known Grace since we were kids. But there certainly wasn’t any romance there; there hadn’t ever been. She went to college across the country from me, and these days I only saw her a handful of times each year, around the holidays. We weren’t close.

I’d tried to protest my mother’s choice. I liked Grace just fine, but I didn’t want to be saddled with a non-romantic plus one, even if it was a family wedding. But my mother’s scathing, ‘nonsense, Nathan, Grace is lovely, and it’s not as if you have a girlfriend you’re going to bring’ delivered with a severe eye-roll, had put an immediate end to the conversation.

I sighed, and then realized I’d been silent for a moment or two too long; Madison was now looking at me, quizzically. As if she was wondering whether maybe I didn’t know if I was going alone or with a plus one.

I pulled the sour expression off my face at the thought of my mother’s machinations. “Uh, I’ve got a plus one, yeah.”

“Great! Can you text your girlfriend,” Madison paused, made a slight moue, as if she’d made an error, and then smoothly, added, “or, uh, whoever your plus one is ... and ask what the wedding party colors are, and what color your date’s outfit will be?”

I knew she was probably just trying to be inclusive about her assumptions; for all she knew, I was gay and bringing a man.

But it felt so much like she was mirroring my mother’s incredulity at the idea that I might have a girlfriend.

“Um...” The idea of texting Grace to ask what she was wearing felt a little awkward – I didn’t know her that well – but I didn’t see why not. “Sure, she’ll probably know.”

It felt a little childish. But I still found myself wanting to impress this attractive woman, or at least, to climb my way out of the conversational deficit I’d dug. So I took the chance to specify that, yes indeed, I was a guy bringing a girl to a wedding. A straight guy who liked girls. Super straight. Definitely not gay.

I pulled up Grace’s number, and fired off a text: Hey, picking out my outfit. What colors are you wearing? I don’t want to clash. Also, do you know what the wedding party colors are?

“Good!” Madison clapped her hands together briskly. “Now, while we wait for her to reply ... how tight do you like your suits to fit?”

“Um ... kind of... normal?” I said the word knowing it was almost certainly not the right answer, but I didn’t know what other words to use.

Madison laughed again – it was kinder this time, but still had that same hint of mockery that her laugh had held before. “Nate, you’re at the most expensive suit shop in Aspen. We don’t do normal fits. Stand up for me.”

Uncertainly, I did so, standing on the little raised platform that my chair was on.

“Good.” She scooted her stool over. “Now, let me be more specific. How tight do you want your suit pants to be? These jeans you’re wearing are pretty loose, as a point of reference. Probably looser than you want a suit to be. So...”

She reached out, pinching some of the loose fabric of one of the legs of my jeans about halfway up the outside of my thigh between her thumb and forefinger. “This tight? Maybe tighter? You could go even tighter, if you wanted...” She pinched off progressively more fabric, with each question, demonstrating how tight the cut could be.

“U-uh...”

I stammered the word out. I was feeling a little slow on the uptake, as a few things registered for me in rapid succession.

The first was that, with me standing on this little raised platform and her seated on the stool, my groin was precisely at eye level with her face. Which, I supposed, was the point – to put her in a good position to assess the fit of my garments, top and bottom.

But, it meant that currently, those big, pretty hazel eyes were looking up at mine from crotch height. She still had a little smile on her face at the idea of a normal fit. I could feel her fingers grazing my thigh as she pulled the leg of my jeans tighter. And the angle gave me another excellent view of her breasts, full and round, straining against that blouse...

It was altogether kind of hot.

And then I realized, to my horror, that I was getting hard. Not like, tent-in-my-pants hard. Not fully erect. But engorged. The view, her proximity, and that laugh had done it.

I was hard enough so that – as she pinched the fabric of the jeans closer and closer to my body – I could see the clear outline of my cock as I looked down. She wasn’t really looking directly at it, but it was already hard to miss. “Uh, maybe looser than that...”

“A little looser, huh? Like this?” She glanced up at me, making eye contact, as she let some of the fabric ease out from between her fingertips. “So you can still bust a move on the dance floor?” She brought her free hand up above her head, closed her eyes, and gave a little shimmy of her shoulders and her hips, pantomiming dancing even though she was seated.

“Sure,” I said, hurriedly, staring at her curves as she moved her body to the unseen rhythm.

The realization that this pretty, confident woman was going to get an eyeful of my rapidly-hardening cock if I didn’t get a handle on my arousal only served to make me harder.

I was, fortunately, rescued. My phone pinged, and Madison perked up, stood up. “Oh, maybe that’s your girlfriend?”

I didn’t bother to correct Madison; Grace wasn’t my girlfriend, but she had indeed replied. I just pulled out my phone.

Grace: bridesmaids are in sage; copper and cream are the other wedding colors. One sec, I’ll send you a photo of my dress too. Surprised you thought to ask, TBH; classy of you, Nate.;)

“See? Ladies love a guy who thinks about this stuff! You’re totally going to get lucky!”

I practically jumped out of my skin at the words in my ear. Madison had quietly scooted around and was standing close, peering over my shoulder to read the message, too.

Madison just continued, as if she hadn’t. “Okay, we’ll need to see her dress before I can pick out a color for you, but sage, copper and cream give us most of the usual options, at least. We’ll probably keep you classic – maybe a charcoal or maybe a navy, depending on her dress...”

“Uh, sounds good...” I was blushing, furiously. She’d read the text. And she’d said I was going to get laid. I wondered if she was right; it was the flirtiest thing Grace had ever said to me. A winking emoji.

“How long have you been together with ... Grace, was it?” Madison asked, conversationally.

“Oh, no, we’re not ... um, she’s not exactly my girlfriend. Just a close childhood friend. Knows the family well and all that.” I blurted it out awkwardly.

“Ah.” Madison winced, giving me a sympathetic look. “Maybe not getting laid, then? My mistake.”

I nodded, embarrassed by her initial misunderstanding and even more embarrassed by her pity. We lapsed into a momentary silence, fortunately interrupted by the phone pinging again.

Madison expectantly peered over my shoulder as I pulled open the text.

It was Grace. She’d taken the photo in the dressing room of some department store, standing in front of the mirror. She was wearing a dress with the tags on. A frosty blue, with a floral pattern.

In spite of the terrible lighting and mirror-photo, Grace looked great. She’d always been pretty – a brunette with cute features, and a lean body from years of soccer and field hockey. The neckline swept down in a deep, narrow V, and Grace was twisted at the waist to show off the enticing cleavage that the dress created, as well as the way the rear of the dress swelled out over the curve of her pert ass.

She had a nice butt. I’d always thought so, and this certainly confirmed it.

My eyes admittedly lingered, silently, on the photo for a few long moments, ogling. And then I glanced at Madison ... only to realize that she wasn’t looking at the photo. Her eyes were on me, an amused expression on her face.

I had no idea how long she’d been watching me stare, instead of looking at my phone.

“So, uh, a blue dress,” I said, a little lamely.

A smile silently spread across her face. “Most people can identify colors a little more quickly than that, Nate,” she noted, teasingly.

I reddened.

I was conscious of how close she was standing to me, in order to see my phone. I could actually feel the curve of one of her breasts pressing into my side, warm and full. Her confident, teasing presence was intoxicating.

Then she pulled away, moving over to one of the racks of clothing. “You’ll want a medium grey suit, with your date in that shade of blue,” she mused, aloud. “Not too light; not too dark ... something like this.”

She pulled a suit jacket off the rack and held it up in front of me for approval. It was, indeed, a medium grey. I blinked a few times. It looked... fine? “Um ... looks good to me if it looks good to you.”

“Show me the photo again,” she directed. I held up the phone. Madison glanced back and forth again, from the suit jacket, to Grace’s photo, to my face several times. Then, finally, she nodded.

 
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