Jay Friday
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A Tailored Release
🕑 Added 2025-07-28 13:30:46 +0000 UTCAuthor's Note: As mentioned in one of my other recent posts, I'm still working on the final chapter of Hospital Stay; it'll be released in August at some point as a bonus to the usual cadence of Monday releases. But here's the second June poll-winner -- a stand-alone story, although as you'll see, maybe it leaves room for a sequel at some point. :)
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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. And thus: me, following in my mother’s wake as she strode into the menswear boutique with the air of a woman who expects someone to immediately be available to meet her every whim.
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?”
She 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 the woman’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. “One of my sales associates will 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 already moved on as well. 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. Madison here is one of our personal style consultants. She’ll be helping you today, Nathan. ”
“Um, thanks.” I pulled my attention off of Madison. 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 go by Nathan, or 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, 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 to a tailor who had offered me a beverage. 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.
Now that we were sitting facing each other, I could see she was a few years older than me; maybe in her late twenties. “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 were 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 realized that she’d 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. So 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, 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 ongoing 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 for myself. 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 made 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 scooted around and was standing close, peering over my shoulder, and I hadn’t noticed.
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 classic 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, but 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 her eyes were on me, an amused expression on her face. I had no idea how long she’d been watching me, instead of looking at my phone.
Or been watching me stare.
“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 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.
“It’s right. White shirt, a tie that’s got some blue and some notes of copper to it, maybe, so you pull from her dress and the wedding palette. You’ll look great.” She sounded satisfied.
I just nodded.
Madison glanced back at my phone one last time as I slid it back into my pocket. “Which is good, because your date knows what she’s doing so you’ve gotta bring your A-game. She’s pretty, and that’s a great dress for her figure.”
She got a speculative look in her eyes as she put the suit jacket on its hangar back on a rack. “But not your girlfriend, huh? Have you two ever been involved at all?”
I shook my head. “No, just childhood friends, like I said.”
Madison picked up a cloth tape measure. “Really? Not anything at all? No back-from-college hookups during Christmas break or anything?” She was disbelieving, and…pleased? Amused?
I couldn’t tell, exactly. So I just laughed uncomfortably. “No…why?”
“Oh, I feel like childhood friends sometimes have unspoken sexual tension, don't you? And you were just, y’know, staring for quite a while there. Hold your arms straight out to the sides, please.” Her amusement turned peremptory on the last sentence.
I did so, still off-balance.
She moved to stand behind me, wrapping the tape measure around my chest. “Well, maybe this wedding is an opportunity to see if there’s any chemistry there, you know?”
She murmured the words close to my ear, and I realized that all of this – the picture of Grace in that dress, Madison’s teasing – had taken me from somewhat hard to fully erect.
My cock strained against my jeans. “Uh, yeah, I guess,” I muttered. I was glad she was at least standing behind me.
She moved the tape to my arm, wrapping it around my bicep; her fingers traced along my arm as well, as she cinched the tape around me. “I mean, I feel like weddings are always good for that sort of thing. Good music, dancing, drinks flowing, you’re celebrating two other people’s romance, having a good time…you’re both headed back to hotel rooms alone, unless…”
And then, to my horror, she stepped around in front of me. Worried she’d see my cock tenting my pants, I kind of…sagged, a little, as I stood there, in an effort to make my erection less obvious. God, this was fucking embarrassing, and the only thing that would make it work would be confronting this woman with the outline of my hard cock.
Through my t-shirt, I felt her fingers graze me at my waist as she wrapped the tape measure around it. “Nate, straighten up please,” she instructed. “Otherwise the suit jacket won’t fit.”
Reluctantly, still trying to keep my hips back a little bit to make my erection less obvious, I met her gaze and straightened a little.
She giggled. “C’mon.” She prodded me, gently, at my belly button. “Straighten all the way up, Nate. We’ve got a reputation to maintain; I can’t have you running around in a suit that fits weird because you’re slouching when I measure you.”
I straightened up all the way, glancing down. My cock was now incredibly obvious through my pants, and my face was bright red. “I, uh…s-sorry…” I mumbled the words out, not sure whether I was apologizing for the slouch, for my cock, or both.
“Good. Stay standing just like that.” It seemed to me that she lingered much longer on this measurement than the others. For a few seconds, she just looked down silently, biting her lip in concentration as she looked at the measuring tape.
At least, I hoped she was looking at the measuring tape.
My erection was incredibly visible, protruding against my pants, though.
“Well,” she mused, “making this work will be tight...”
“W-what do you, uh…” I said, unintelligibly. I felt completely on the back foot, and looking down, I could see my cock twitch at her comment. It sounded like she was talking about-
“I mean, you’ve got a slim waist; the drop between your chest and your hips is significant. Ordinarily we’d probably insist on making it custom; adjusting something off the rack will be tough to do while still meeting our standards.”
“Oh. Right. Um, okay…” There was no teasing innuendo in her voice, just a thoughtfulness -- someone puzzling out a problem. She was just taking my measurements. A professional. Maybe a flirty professional, sure, but a professional.
I wasn’t sure whether to be relieved or worried, at that thought.
On the one hand, it felt a little less like I was being bullied when she laughed.
On the other, it meant that she might be really pissed if she realized the effect she was having on me.
She pursed her lips. She walked over to the rack and pulled a pair of suit pants that matched the jacket off of a hangar, checking their size. “Okay. I think the tailor will be able to make it work, but it means I should probably pin and mark the pants instead of just taking your measurements on those. So I’ll need you to change into these. You can change in our bathroom; head back into the hallway and go into the first door to the right.”
I took the pants and fled, grateful for a reprieve.
In the bathroom, I pulled off my jeans quickly enough…but then glanced at the mirror and froze. The wet spot in my boxers at the tip of my throbbing cock had grown embarrassingly large. I’d been leaking precum the whole time.
In fact, I was turned on enough that I considered jerking off for some relief. With how aroused I was, I knew it wouldn’t take long to finish. Madison was just so...sexy.
But I didn’t need my cock leaking the aftermath of an orgasm into my boxers while she finished measuring me. Especially if Madison was going to be at face-level with my groin.
The way things were going, it was all too easy to imagine what would happen. She’d be adjusting my pants. Then she’d wrinkle her nose cutely, asking me if I was wearing cologne, saying she’d never smelled this particular scent before, but that it wasn’t unpleasant; maybe I should wear it tomorrow night, Grace would be impressed…
My cock was throbbing as I thought about it. Jerking off seemed like a bad idea.
Waiting for my erection to go down was going to be an exercise in futility, too, I knew.
All I could think about was Madison’s big hazel eyes, the way her tits strained against her blouse, the teasing tone in her voice. The warm, assured touch of her hands. There was no way I’d be calm in any reasonable amount of time.
And the last thing I needed was for her to come to the bathroom door to check on me. With a resigned sigh, I settled on adjusting my cock so that it was more or less pointed straight up. I put on the suit pants. The material was thinner, and they were cut differently from my jeans, but the waist was pretty loose – my cock was a lot less visible, angled this way.
The process had gone quickly enough on the suit jacket. Hopefully the pants would be done and I’d be out of here soon enough.
I returned to the room; Madison was bent over, rummaging through a cabinet in one corner. I got a nice view of the curves of her ass before she stood and looked over at me. “Great! Those look loose, especially around the waist, like I expected. Stand up here again. Now, let’s see…”
I stood, and she walked in a circle around me, eyes fixed on my midsection. I tried not to blush under the scrutiny. At least my cock, while still hard, wasn’t massively tenting my pants right in front of her face.
“Good. Now, hold still while I measure…”
She took the measuring tape and wrapped it around me, right at the waistband of the pants. I swallowed hard, looking away from her face, three or four inches away from my cock. I could feel my cock twitching at how close she was, and I didn’t need to make this more difficult for myself.
And then she brought the measuring tape lower, like she was measuring around my hips. I felt the tape pleasantly drape across my erect length, pressing into it a little as she pulled it taut around me. Shit. It was probably making my erection really obvious.
But she only held it there for a moment. “All good, I think we can make this work,” she said, thoughtfully.
And then she pulled back, pulling the tape away from me and standing up. She moved slowly, like considering what adjustments to make to my pants.
As a result, in the process of her standing, I felt her forearm smoothly brush up the entire length of my cock, an inch at a time.
I froze. There was no way she hadn't noticed that.
And on top of that, the sensation made me suddenly and acutely aware of just how close to an orgasm I actually was. The situation – her nearness, the unintentional teasing, how attractive she was, how embarrassing it was that I was this turned on – was so hot. I hadn’t realized just how close I was. A few more touches like that and I’d be cumming in my pants.
I was close to blowing my load for her, and she wasn’t even doing it on purpose.
The realization was mortifying.
And then she let out a little scandalized gasp. A gasp that broke whatever spell I’d been under and made me aware of just how precarious my situation was.
Oh, fuck. She’d noticed, like I'd expected. Realized that she’d just touched my rock hard cock. She was going to kick me out of the store, or maybe call the cops–
“Nate.” Her tone had gone admonishing.
“S-sorry,” I stuttered. I didn’t want to even risk looking at her.
“You should be!”
“No, I-I know, yeah, I am,” I mumbled. Jesus. I was probably going to jail.
“I mean, you can’t have your phone in your pocket while I’m measuring, it throws the fit off completely!”
I blinked. I looked at her.
The severity on her face was only mock-severity, a twinkle in her eye. “Take it out and put it over there. Do you have anything else in there? Car keys? Anything, y’know, bulky in your pants is going to throw the fit off.”
She’d thought it was my phone she’d brushed against.
I pulled my phone out. The mental rollercoaster I was on – so aroused I was ready to cum, confused about whether Madison had even noticed my erection, and now the sheer relief at her not having noticed – just seemed to go on forever. I took in a shaky breath and gave her a tentative smile. “Uh, sorry again.”
“Oh, it’s fine, I’m just giving you a hard time.” She gave me a pat on the arm. “You know, I should probably just pin things in place and mark them with chalk anyway, we don’t need to measure again.”
She grabbed a handful of tailor’s pins, started pinning the cuffs of the pants up a little higher, then taking in the fabric around the calves a little bit, too.
I watched her work, glad for the reprieve. I picked up my long-forgotten beer, and sipped at it, hoping the cold shock of liquid hitting me would cool my overeager libido, how heated this encounter felt.
It did help, a little.
And then, as she moved from my calves up to my thighs, a little of the condensation on the beer can dripped.
Directly onto her exposed cleavage.
She let out a hiss of breath at the sudden sensation, glancing up sharply. Her eyes took in what had happened quickly, though, and crinkled into a smile. “Jeez, that fridge does really keep the beers cold, huh?”
I nodded, dumbly. I was staring at the beaded water on her cleavage. As I watched, she smeared it with a finger, spreading the moisture across the expanse of one full breast.
My cock twitched again as I watched her glistening cleavage. The sight was seared into my mind. I had no doubt my boxers were a mess of precum.
“Almost done. Thanks for being so patient.” She’d arrived back at my waist, was biting her lip in concentration as she stuck tailor’s pins into various places in the waistband of the pants, cinching it tighter around my waist.
“Sure.” She was hot, but I was ready for this to be over. Madison had given me enough material in the spank bank for months.
“Okay, last thing. I need to mark this with chalk so the tailor knows how to hem it. That’ll make sure the drape is right…tight, but not too tight, so you can dance nice and close with Grace!” She glanced up at me, continuing to work her way around my upper thigh and waist.
As she leaned closer to get around to my side, it pressed her chest into my boxers. I could feel the mounds of her tits, full and soft, one on each side, my cock in the middle.
The sensation that I was close to cumming, that it wouldn’t take much stimulation at all, surged back in me. I closed my eyes, trying to stave off the orgasm, hoping she couldn’t feel my cock wedged between her breasts. Hoping this would only take a moment.
But she wasn’t making any moves to adjust her position.
"Madison, uh, wait a sec, something um, feels like it’s getting pinched, maybe by the pins, I think,” I said, desperation causing me to get creative. I couldn't last much longer. I opened my eyes and looked down at her, hopefully.
She met my eyes. “Pinched? But I’m being so careful to make sure it feels good.” There was a slight, satisfied smile on her face, now, as she looked up at me.
My cock lurched. Oh, god.
I’d been wrong. There was no mistaking the look on her face. Not only had she known it was my cock earlier, she was doing this on purpose.
And I could see, from the smug look in her eye, that she also knew that I was on the verge of cumming.
“You know, I’m realizing I forgot to mention.” Her voice was conversational. “I heard Nancy and your mom talking when you first came in, and I’ll actually be at the wedding tomorrow too! The bride and I are friends. So exciting for Kelly and Steve, right?”
Oh, fuck.
This wasn’t just some woman I’d never see again. She’d be at the wedding.
And I was about to cum in my pants against her chest. “Oh, uh, awesome,” I mumbled, automatically. I was focused on trying not to blow my load with her tits pressing into my groin.
“And this means I’ll get to meet Grace, and see how the two of you look together with you in that suit! I bet she’ll think you’re cute!” she said it with enthusiasm, still fiddling with the chalk around the waistband of the suit pants.
The combination of realizations – that she’d been doing it all deliberately, teasing me and working me up, now knew I was about to cum, and she’d see me tomorrow night, too – was too much to bear.
I was about to cross the point of no return. I’d waited too long. Even if she’d pulled away, as I’d hoped — and she didn’t – it might be too late to stop what was going to happen.
“I hope we’re seated near each other at dinner…you seem so fun…” As she spoke, she leaned further into me, and I felt her tits press around me with more pressure, luxuriously soft…
She hadn't even taken her clothes off, I told myself desperately, trying to calm myself down, fighting to keep from cumming. I hadn't even taken my clothes off. The thought was humiliating.
It didn't matter. That was it. The orgasm swept over me. There was no holding it back.
I tried to let it happen silently...but after all her teasing, a few moments of her chest against me had stoked my arousal to a height I hadn’t expected. And holding back the pleasure, fighting it off to the limits of my stamina, trying to resist her, meant that when it finally overwhelmed me, it was explosive.
As I felt my cock spurt the first jet of cum into my boxers, against the softness of her chest, I let out a low, slightly horrified moan. Not a loud one, but loud enough for Madison to look up and make eye contact with me.
“Everything ok, Nate? It doesn’t look like anything’s pinching.” she asked, quietly. Smugly. Victoriously.
I knew I wouldn’t be able to speak coherently, so I didn’t say anything. I was doing my best to control myself as I came, minimizing how much I moved and the noise I made. But I still bucked my hips a little against her chest, helplessly.
“I bet Grace’s going to be so impressed by the suit. It’s almost like I’ll be your wingwoman, huh?”
She twisted a little bit, as if inspecting the fit first on one side of my body, then the other. The effect caused her chest to shift and back forth, softly rubbing against my cock.
It felt exquisite. “Nngh,” I grunted out another spasm of cum into my pants.
She was still pressing her chest into my groin. “I mean, maybe I’ll help you out tomorrow night too. You seemed to find the fitting today…helpful.”
I was overwhelmed by the combination of pleasure and embarrassment; I didn’t know what to say.
A few more final throbs of my cock, and she pulled away. I realized I’d lost control so much that I had almost been leaning against her chest; I wobbled and then slumped back, lightheaded.
“At any rate, I think we’re all finished up, huh, and faster than I expected! I’ve got a few other things to take care of before I’m off for my lunch break. You can change in the restroom and leave the suit pants on the hanger in there. Don’t worry, we’ll give them a quick press and clean once the tailor’s done. I’ll make sure to leave a shirt and tie up front, too.”
She stood up, moving towards the door. “And feel free to use the restroom if you need to freshen up before you head out. Nancy can ring you up in the front. The suit will be ready in a couple of hours.”
I was completely at a loss for how to proceed. What was I supposed to do, get mad? Thank her for making me blow my load? Thank her for...fitting me for a suit?
Uncertainly, I settled on a tentative and vague, “Um, thanks?”
And then I started moving towards the door.
“Oh, no need to thank me. We pride ourselves on offering exceptional service.” The words were sarcastic, and she studiously didn’t look down at my groin, but her lips quirked into a smile as she looked over her shoulder, on her way out of the room. “See you tomorrow. I can’t wait to meet Grace!"
Comments
Bob
Thanks!
roxas_duh
I loved the way the story was structured. I am eager to see this continue soon as well
Bob
Thanks so much!
Sam
When you put the scenario in the poll I didn't expect that much from it compared to all the other great stories. But this was a really entertaining one. I think if you decide to continue it, I would enjoy more from this as well.
