A Tailored Release
Copyright© 2025 by JayFriday
Chapter 3: A Storied Release
Erotica Sex Story: Chapter 3: A Storied Release - 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 Mult Reluctant Heterosexual Fiction DomSub FemaleDom Humiliation Petting
The cold Aspen air bit against my skin as I hurried toward the idling coach bus.
I’d stopped to clean myself up in the bathroom as best I could, but otherwise I’d just headed straight out the door; I wasn’t really interested in lingering in a way that might make the evening even more humiliating.
I jammed my hands into pants pockets, and found the hole – the one Madison had clearly put there deliberately. I yanked my blazer closed, jaw tight.
The music thumped behind me, but I was done. With the wedding. With Madison’s games.
All I wanted was to get to the hotel, shower, and forget the look on Grace’s face, Madison’s victorious smile.
I was two steps from the open bus door when Madison’s voice sliced through the night.
“Nate.”
I turned. She was leaning against the brick wall, arms folded under her tits, dress still clinging to every generous curve. Her eyes glowed with wicked amusement.
“You’re really going to leave?” She tipped her chin at the bus. “After all that? You’ve run most of the race and you’re quitting just before the finish line.”
I regarded her, stony-faced. “I’m done playing your game, Madison.”
She pushed off the wall, heels clicking as she approached. “Even after I promised you’d get laid if you stuck it out until the end? And after all the trouble I’ve gone to serve Grace up to you on a silver platter. After telling you I’d sleep with you, even. I’m a little hurt.”
I shifted, the embarrassment and anger prickling again. “Maybe I’m just not in the mood anymore.”
Madison leaned in. I could smell her perfume, warm against the chilly winter air. Her voice was low and mocking. “I guess I understand, after that little performance on the dance floor. You must know you’d blow your load before you even got inside me. I’m down to fuck, but you wouldn’t even be able to get it in.”
I bristled, jaw set. “Fuck off.”
She laughed, delighted. “Ooh, some spirit. Prove me wrong, then. Or leave, and admit you can’t. Just ninety more minutes. You last until the end of the night, and you’ll get to fuck me however you want. That is, if you can actually fuck me.”
I stared at her, anger burning hot in my chest. “Fine. I’ll stay. But you’d better deliver.”
She grinned, pleased with herself. “Oh, I’m not the one who seems like they have trouble delivering.”
Redfaced, I turned away from her -- and from the bus -- and headed back inside.
Inside, the reception was a blur of noise and lights. I grabbed a drink and hid at the back, avoiding everyone, letting the champagne burn away my shame.
My mind kept circling back to the look on Grace’s face when she realized what had happened, the way her ass had moved against me.
The sound of Madison whispering in my ear as I came, how her tits had felt in my hands. The sticky, humiliating loss of control.
The fact that it had been pretty hot only made it more humiliating. I wanted to crawl out of my own body. Or maybe just dig a hole under the table and hide until everyone else had gone home.
I settled on a second drink from the bar instead, just trying to pass the time until I could leave.
I tried to entertain myself with ideas of turning Madison down -- getting to the end of the evening and then abruptly slamming my hotel-room door in her face. How righteous that would feel.
I knew I wouldn’t. I would need to blow off some steam. And she was hot. But that would be satisfying in its own way, too. Maybe I could fuck her hard, make her beg for my cock. Hell, even making her beg me to stop would be amazing.
I was well down this trail of thought, staring contemplatively at the dance floor, when Grace appeared at my elbow, her blue dress shimmering in the low light.
She looked different now: hair a little mussed, cheeks flushed, eyes shining.
She slid into the chair beside me, sat silently for a moment. When she spoke, her voice was light. “Hey, Nate. Hiding out?”
I forced a smile. “Just needed a breather.”
She grinned, folding her arms on the table and leaning in. “I bet. You know, I wasn’t expecting you to be the kind of guy who finishes before the music even stops.”
I choked on my drink, sputtering. “Grace-”
She giggled, delighted by my response. “I mean, you must’ve been really worked up.”
My face burned. “It’s not, uh, exactly how I wanted the night to go.”
Before Grace could reply to that, Madison slid in beside me, all red silk and a predatory smile.
“Hiding out, Nate? Or just hoping someone else will clean up your mess?”
Grace’s eyes sparkled. “You know, you could’ve warned me he’s a bit quick, Madison, I would’ve taken it easy on him.”
With the two of them ganging up on me, I wanted to sink into the floor and vanish.
Madison put on an expression of exaggerated shock, her lips parted. “I mean, he isn’t. I’m sure it was a one-off accident. He must just like you a lot, or something.”
Now it was my turn to be shocked. Grace was, too. “Come on. I know you’re his friend, but it was pretty ... definitive, from where I was standing. And I had a front row seat, as it were.”
Madison scoffed. “Okay, listen, he hates when I talk about this sort of thing, but I’d better help clear this up. Don’t get pissy, okay, Nate?” Then she leaned forward conspiratorially.
I braced myself. I was sure she’d find a way to make this even more humiliating for me. Grace leaned in as well, clearly excited by whatever Madison was about to share.
“I’ve heard this guy in action, okay?” She fixed Grace with a wicked smile. “I crashed on his couch one night two semesters ago -- he and his roommates were hosting a party, and I didn’t want to drive home. Anyway, he had took another girl back to his room. I swear to god, I heard them going at it for hours. The next morning, she could barely walk straight. She told me -- between mouthfuls of Advil and water -- that she’d never been so thoroughly fucked in her life. She used the word glorious. It was kind of the beginning of the reputation he has, that I was telling you about.”
Grace’s mouth fell open. “Seriously?” She looked at Monica, then at me.
Madison nodded, deadpan. “Dead serious. I mean, I don’t know firsthand, obviously, like we talked about; he’s not my type and I’m not his. We’re just friends. But everything I’ve heard is that Nate can lay pipe, Grace.”
I blinked at Monica, aghast at the lies, but my cock stirring in spite of them.
“Aw, I’m embarrassing him. He hates it when I talk like this. Sorry, Nate.” Madison winked at me, her fingers grazing my thigh under the table.
Grace was eyeing me more thoughtfully, now. “So ... if that’s true, then why ... on the dance floor...?”
I wasn’t sure what Madison was playing at. I certainly felt suspicious rather than grateful. She was up to something.
But nonetheless, I pulled myself together, found the wherewithal to shrug, and give her a sly grin. “I didn’t expect you to know how to move like that, is all. I mean, damn.”
Grace flushed with pleasure, and laughed; she leaned in a little closer looking intrigued. “Well. I have to admit, I just sort of figured this kind of thing happened to you all the time. This is a surprise.”
Madison’s hand squeezed my thigh under the table. “Well, Nate loves surprises,” she said lightly, her tone wicked. “He likes a challenge, too. Trust me.”
Grace grinned appreciatively at Madison, then looked back at me, a new playfulness in her gaze. “Yeah? Think you can handle a little more dancing, then?”
My mouth was dry. Madison’s hand drifted further in across my thigh; I felt her nails graze my balls through the fabric of my pants. I was having trouble recalibrating.
But somehow, Madison had explained away my embarrassment on the dance floor in seconds. Made it a compliment for Grace instead of a humiliation for me.
“Oh, I’m up for it,” I managed, voice steadier than I felt.
Grace stood, smoothing down her dress. “Great.”
I shot a look at Madison as I stood to follow Grace. Madison just smiled, all satisfaction, her hand slipping away ... but not before her palm drifted, soft and slow, across my cock as I pulled myself to my feet. It sent a jolt of sensation through me. She lifted that same palm in a little, idle wave as we walked towards the music.
On the dance floor, Grace pressed against me. For a few minutes, I managed to forget Madison. It was just Grace again: her warmth, her body, the throb of music.
She tilted her head to lean it on my shoulder, speaking loudly to be heard over the music and celebration happening around us. “Madison must be a really good friend.”
“Uh, yeah.” My hands were on the small of her back again; I could feel her warm, bare skin where the back of her dress plunged.
“It’s kind of nice to know that you know what you’re doing,” Grace confessed. “A-after earlier, I worried...”
I let out an embarrassed snort of laughter, grateful that she couldn’t see how red my face was. “Um, totally understandable. But ... much as I hate it when she tells stories about me, Madison’s right.” I set my teeth, gritting out the lie and the final two words in spite of how they pained me.
“So you must really like me, then,” Grace said. Her voice had gone soft; I could barely hear her.
That at least was easy to reply to. I pulled back, and looked her directly and honestly in the eyes. “Yeah. I really do.”
Grace smiled, and then spun around, putting my hands back at her hips so she was swaying with her back against me. “Good. And if Madison is right ... then this won’t bother you?”
I could feel my cock – soft, but engorged and swelling – nestle against her ass through her clothes. She glanced up and back at me, coy.
“I wouldn’t say it bothers me.” I pushed into her butt, hoping she’d feel what was an appropriately thick, masculine bulge. And then I lowered my mouth from her ear, to her neck. Brushed my lips along her skin, briefly.
With a surge of satisfaction, I heard her breath catch in her throat.
“Oh.” She let out the breath with a little sigh, and pushed back into me harder. I knew I’d been staring at her ass all night, but in my defense, it felt justified. She had an incredible butt, and – as she began rhythmically pushing it against groin again – I got harder.
She twisted to look back at me. “You do seem to like girls who know how to have fun on the dance floor, like Madison was saying,” she murmured, an impish little smile on her face.
I grinned back. In spite of myself, I was thinking about what Madison had said about Grace, before I’d lost control.
One of those quiet girls who’s a freak in bed, I bet. Probably loves taking backshots.
I’d been worried that our chemistry had been irreparably damaged after my accident, but the way she was looking at me, I knew it hadn’t been.
God, I wanted to fuck Grace so badly, now.
She was clearly thinking along the same lines, and she leaned in to whisper in my ear. “Earlier, y’know ... before you were surprised by what a good dancer I am...” Her lips brushed against my neck as they curved into a smile. “ ... You mentioned wanting to get out of here early. Still want to? Because I do.”
My heart swelled. “Yeah. I’d like that.”
She grinned, cheeks flushing. “Good. Let’s call a ride, then. We could walk, but it’s freezing outside.”
We slipped away from the dance floor, skirting past the straggle of guests. I felt Madison’s gaze on us as we crossed the room, but I didn’t look back. I was sure she was laying some trap, some new, shame-inducing setup.
We lingered in the foyer; you could feel the bitter cold from outside. Grace pulled her phone out, thumbing at the rideshare app. I slid my arm around her waist, let my hand drift from her low back to rest on the swell of her ass. She looked up at me, gave me a little grin.
The car arrived. We headed outside to meet it. Just as I was opening the door for Grace, we heard heels clicking on the pavement behind us.
Madison, of course. My heart sank.
She was flushed from the warmth inside, dark hair tumbling over her shoulders. “You two done for the night?” she said, her voice icy sweet. “Mind if I catch a ride back to the hotel with you?”
Grace straightened, not pulling away from my arm. “Of course!” Grace’s voice was friendly.
So much for being free of her. But I couldn’t object at my very good friend Madison hitching a ride back with us, could I?
Sighing, I held the car door open for both of them.
The ride was quiet, brief. Blessedly, Grace was sitting in the middle, with Madison on one side and me on the other. Madison filled the silence with some innocuous, made-up story about Lisa, her idiosyncratic roommate. Grace laughed along appreciatively, one of her hands resting, suggestively, on my thigh.
When we arrived and all hurried inside out of the cold, Madison’s eyes lit up at the sight of the hotel bar, just off the lobby – still open, almost entirely empty, a bored-looking bartender standing behind the bar. “A final round of drinks?”
Grace clapped her hands gleefully. I bit back the surge of disappointment. We’d be free of Madison soon, I was sure, just evidently not right now
“I’ll get the drinks!”
Madison and I grabbed a high-top table. I watched Grace go, staring – for what must’ve been in the twentieth time this evening – at her ass, shifting under that blue dress, the sway of her hips as she walked over to the bar.
“Thinking about fucking her from behind, huh?”
At Madison’s soft words, I looked her way. She was watching me with an amused smile on her lips.
For a change, I felt only a little embarrassed; Madison had teased me enough about Grace that it didn’t have the effect it one had. “I mean, yeah.”
“Well, I’m glad I could help you patch things up after your little... lapse of control, earlier.” The smile turned condescending.
I felt a flare of resentment. “It’s your fault I was having any trouble in the first place.”
“Yeah.” Her smile widened. “But you wouldn’t have a shot with Grace at all without me anyway.”
“That’s-that’s not true,” I spluttered.
Her eyes narrowed. “Of course it’s true. I’ve been wing-womaning for you, hard, all night.”
“You said yourself that Grace liked me already, that you just had to nudge her along in the right direction,” I pointed out.
“You sound pretty ungrateful, Nate.” Madison’s smile was almost evil. “And you did leave early, didn’t you? You tried to cut and run. Again.”
I did not want Madison as an adversary. “L-look, I-I appreciate-”
“Oh, relax, Nate. Jeez, you’re wound so tight. This is supposed to be fun for you: a romantic wedding, two pretty girls doing a shot with you at a hotel bar before ... well. Look, I won’t ruin things with Grace, but...”
She trailed off, enigmatically.
“But what?” Over her shoulder, I could see Grace returning from the bar; I was desperate to understand what Madison was getting at.
“But you might.” She gave me an enigmatic smile. “Try not to spoil the fun.”
And then Grace was back with drinks, and too close to keep talking without her hearing us.
“So, Grace, you’ve heard a lot about Nate ... let’s hear a few stories about you.” Madison was all smiles.
“Oh ... it doesn’t sound like I’m having the wild time at college that you all are.”
“Aw, c’mon,” Madison encouraged. “You must have at least a few good stories.”
“Mmm...” Grace made a noncommittal sound, blushing.
“She doesn’t have to if she doesn’t want to, Madison,” I said, quickly.
“She knows that,” Madison responded, rolling her eyes. “She’s not some damsel in distress you need to rescue from my corrupting influence, Nate.”
Grace laughed at that; I reddened and shut up.
“Tell us about your corrupting influence, Madison,” Grace suggested. “You must have some good stories, too.”
“One or two, I guess,” she said, offhandedly. Madison took a slow sip of her drink. “Let’s see... oh. Here’s one not even Nate’s heard.”
She leaned in, her voice dropping just enough to draw Grace closer, conspiratorial. “Last spring, I was at this friend’s birthday party in Denver. Fancy rooftop bar, everyone dressed up, you know the type. I didn’t know many people, but I got talking with this couple—super cute, clearly in that honeymoon phase. The guy was nice, but the girlfriend ... well. I wasn’t wearing this dress, but another one that was, y’know... similar.”
Madison glanced down at her own tits; Grace and I both followed her eyes, automatically, taking in the sight of her tits. I could still recall how they felt in my hands, earlier. How they’d felt against my cock, even through the clothes, yesterday.
“Anyway, the girlfriend could not stop staring at my tits all night. I mean, she was making it obvious. Every time I leaned over, her eyes got wide as saucers; she just couldn’t seem to look away.”
She grinned, glancing between the two of us looking at her breasts with amusement. “Anyway, later on, we got a little tipsy, and it was just the three of us out on the balcony. He went to grab drinks, and she finally blurted out, ‘Sorry, I can’t help it, you just have amazing boobs.’ She was cute, so I told her, ‘As long as your boyfriend won’t mind, it’s fine with me if you want to give them a squeeze.’”
Grace snorted, blushing and covering her mouth. “You did not!”
“Oh, I absolutely did,” Madison said, her grin widening. “She turned bright red, but next thing I knew, she had both hands on me, just ... full-on groping, squishing, like she’d never touched another girl before. She kept saying, ‘God, they’re so soft, they’re perfect... ‘ It was adorable.”
“You’re joking.” I paused, drink nearly raised to my lips. “Come on.”
“Nope, it’s true.” Madison didn’t even look up at me; her eyes were on Grace, lingering, as she went on, her tone languid and teasing. “She got so into it, she buried her face between them. Aaaand that’s when her boyfriend walked out. He just stood stock still, staring at her with her face buried in my cleavage.”
“So then what happened?” Grace breathed the question out, eyes darting between Madison’s face and tits.
“Well...” Madison let the moment hang, then finished, her grin turning sly, “Nothing, actually. She eventually came up for air; we all laughed about it. Next morning, she texted me, thanking me for ‘letting her play.’ She said, ‘You have the best tits I’ve ever touched. No contest.’ And that her boyfriend was like an animal in bed that night, couldn’t keep his hands off her, kept asking her how my tits felt, asked her if she liked it.”
Grace was speechless, her face bright red.
But I wasn’t having it. “Come on. No way that happened.”
Madison shrugged. “I mean, I should still have the texts saved...” She pulled out her phone, and started scrolling.
I waited for her to ‘realize’ she’d deleted them. But instead, a moment later, she just handed me the phone.
Wendy: Thanks for letting me play. God, your tits are fucking perfect.
Madison: Any time. Let me know if you ever want to play some more.
Wendy: God, you’re tempting. Shawn fucked me like you wouldn’t believe last night. Just kept talking about how hot I looked touching your big tits, asking me how they felt, asking if I’d liked doing it...
Madison: Mmm. That’s hot. If he ever wants to get a feel too, I might be game...
Wendy: Should I start a group text with the three of us?
Madison: I’d like that.
That was the last message on this chain, although now I was half-tempted to swipe through Madison’s phone. Jesus.
Grace, watching me, started giggling. “You should see your face, Nate. Guess she wasn’t lying, huh?”
I shook my head slowly, handed the phone back to Madison; I wasn’t sure I wanted Grace to read that exchange.
I’d gotten hard again, I realized. Madison was something else. I wondered if this was her plan for us; not to necessarily get laid, but just to play with us, get us both really turned on, and then set us loose on one another.
Well. If that’s what she wanted, I was game.
As if she could read my mind, Madison just gave me a tight, smug little smile. “It just goes to show you that sometimes you don’t know where things’ll lead until you try.”
I swallowed, hard, my eyes darting between the two of them, the tension winding tighter in the air.
“So, Grace, at least tell us if you’ve had many boyfriends?” Madison’s voice was lighter, more casual; a deliberate turn towards less charged topics.
Twenty minutes later, we all walked out of the bar area. Madison trailed after us in the lobby; we all paused a few feet from the bank of elevators. “Alright, kids, I should probably get out of your hair. Grace, it was really nice to meet you.”
I wasn’t sure what I wanted to happen, now.
Mostly, I thought the right call was to bid Madison farewell and have a far-less-complicated end to the evening with only Grace.
That story, though ... those texts...
And her tits.
I imagined Madison naked, under me.
Or Madison under Grace.
Or even just Madison, egging the two of us on.
In the wake of my indecision, Grace responded first.
“Aw,” Grace pouted, hugging her. “It was so good to meet you too! Nate never mentioned how fun his college friend was! You sure you don’t want to come up to my room? We could all have a final nightcap together before turning in.”
I couldn’t see Grace’s face, but I had an excellent view of Madison’s over her shoulder. So I could see the smug triumph written across her face while she embraced Grace.
“Well, you’ve been a blast, Grace. And I hardly ever get to hang out with Nate like this, so if you’re gonna twist my arm...”
The triumph on her face was unsettling. This was part of a plan, something she was doing on purpose.
It was enough to make me nervous.
We all headed up to Grace’s room, riding the elevator up in a hush that was thick with tension.
Madison was leaning against the mirrored wall of the elevator, arms crossed in a way that emphasized her cleavage in that dress.
Grace was pressed into my side, her fingers twined in mine, squeezing as the floors ticked by. Madison caught my eye in the reflection. A slow, knowing smile spread across her lips, as if she could taste my anxiety.