Smut Stroll Feature: The Fitting Room, Part Three
The further continuation of a kinky sexual fantasy
{This post is very definitely NSFW; it is also entirely unsuitable material if you’re underage in your locality; only read on if you’re an adult and you like explicitly sexy stories.}
[Fantasy, MF, consensual sex, cross-dressing. All ‘participants’ are adult, imaginary, and entirely fictional - any resemblance to a real person is sheer coincidence.]
This story series is very ‘occasional’ - the first two parts were published two weeks apart in October 2025. I have written it especially for the occasion of the Substack Smut Stroll curated by the one and only Ella Light:
In Part One (https://open.substack.com/pub/philpshepherd/p/the-fitting-room), our hero was seduced into wearing ladies’ panties by one of the staff of the lingerie shop, and gave her a jolly good fucking in return. The scene ended with them finding his partner ‘in flagrante delicto’ with another of the staff:
My partner, spreadeagled face down on the floor, big round bum high in the air, her pussy being pounded enthusiastically by a busty brunette using a huge strap-on; a big, furry, tail protruding from my partner’s anus; both of them groaning out their arousal.
In Part Two (https://open.substack.com/pub/philpshepherd/p/the-fitting-room-part-two), our hero and ‘his personal shopper’ Yolanda, joined his partner Lucy and her bra fitter Beth, and yet more frantic fucking followed, culminating in the following:
“Same time, same place, next week?” asked Lucy, as she tried to extricate herself from underneath the heap of bodies.
And now, without further ado, the action moves forward a week:
The week followed in a haze of lingerie and frantic coupling… Now that the secret of my lingerie kink was out in the open, I really embraced it, and Lucy and I enjoyed a week ‘bonking like bunnies’ with us both wearing a variety of sexy underwear from her collection. We probably hadn’t had as much sex in one week since our honeymoon. Although I seemed to have become insatiable, and time flew by on one level, on another, it really dragged - I could hardly wait to head off to the lingerie shop.
Eventually though, the day dawned. I’d never realised before why Lucy always went lingerie shopping so late - now I knew that it was so that she was there when they closed, and then they could get up to all kinds of naughty shenanigans together after the other customers had left. But that meant I had almost all day to wait. I was like a cat in a hot tin roof, and the day really dragged. I’d probably have felt better if we’d just had sex, or I’d masturbated, or something - but I wanted to ‘save myself’ for later.
After what felt like a year of waiting, and failing to settle down to concentrate on doing anything, the time arrived, we got in the car and set off.
I tried to start a conversation to while away the drive.
“What are you shopping for?”
“Wait and see - it’s a secret!”
“Okay… Who’s going to be there, and what are we going to do?”
“I don’t know. I guess Yolanda and Beth, because they work there; maybe Hannah and Emily, though they don’t join in as often - they have lives outside the shop and usually have to rush off straight after closing.”
“Are there any other customers who get ‘involved’?”
“There’s Elena. She’s Russian, and has the most beautiful accent… She also has an amazing body, and no inhibitions whatsoever - at least, if she has any limits, they’re way beyond our wildest imaginings. There are one or two others, but with them it’s only been once or twice.”
After parking, we walked to the shop, and went in. It was quite quiet - just a few ladies in, of various ages, browsing the racks. I appeared to be the only guy. Yolanda was dealing with a customer, but gave me a surreptitious wink while the customer wasn’t looking. She was looking stunning, in a low-cut dress which showed off her assets to perfection. By the time I looked around, Lucy was nowhere to be seen. There was no sign of Beth anywhere either.
I looked around, feeling slightly lost… Now that it came to it, out in the public gaze, I was definitely a bit embarrassed by my kink. After a few moments, a voice behind me. Female. Sultry.
“Can I help you?”
I turned, and my gaze fell upon a vision of perfection. A slightly older lady, with flaming red hair, the creamiest skin imaginable, huge boobs and a deep cleavage.
“Er, no… Well, I don’t think so.” I stammered, now acutely embarrassed. “I’m here with my partner, Lucy.”
“Oh, are you Phil? I’ve heard a lot about you.” she said, looking me up and down as though appraising a prize bull.
“And none of it good, I expect.” I said, trying to lighten the mood.
“On the contrary,” she said, licking her lips and giving me a somewhat saucy look - slightly shocking coming from a ‘lady of a certain age’, “all of it good. I hear that you enjoy shopping for lingerie.” her gaze lowering to my crotch. “Why don’t you take a seat over by the fittings rooms, and I’ll bring you a drink; what would you like? I’m Hannah, by the way.”
“Pleased to meet you,” I said, “just some water please.”
“Oh, getting you all hot and bothered are we?” she said, winking.
“Something like that.” I admitted, aware that my cheeks were reddening.
I sat, and looked, and listened. Faintly, under the gentle bustle of the shop, I thought I could hear moaning. Was that Lucy? Who knows? Anyway, it sounded as though someone was really enjoying their shopping.
After a couple of minutes, she came back, with a glass of water, and a bag.
“Thank you.”
“Beth says that Lucy asked her to get this to you.”
I opened it and peeped in. Oh boy. Something bright pink and frilly, and what looked like a pair of stockings. My face must have been a picture…
“Do you need help trying it on?” she asked, trying, and entirely failing, to look nonchalant. “If you give me two minutes, I’ll come and help.”
“Er, no, I think I can manage. Thank you though.” I stuttered. She looked crestfallen and eager, at the same time.
“Are you sure? It’s no trouble.”
‘I’ll bet it isn’t.’ I thought to myself.
“Okay then, if you must.”
At this, her face brightened and she turned and sashayed away, giving me an eyeful of her jiggling buttocks. I felt my cock begin to stir in my pants. Was this going to turn, as I’d hoped, into another lingerie-driven sex fest? I hoped it was, but I was also nervous - I hadn’t expected anyone like Hannah - in fact I’d just been expecting a repeat performance, with Yolanda, Beth and Lucy. My mind drifted to remembering last week’s ‘introduction to lingerie shopping’ - it really had been amazingly sexy fun. My cock thought so too… To judge by what was happening! I was just squirming surreptitiously and adjusting my attire subtly to try to make things more comfortable when Hannah reappeared. She smiled at me, knowingly.
“Come on then.” she said, looking around to make sure we weren’t being watched as she led me to the fitting room at the far end of the little corridor. She opened the door, and then followed me in, turning the bolt behind her to lock the door.
“So, what’s in your bag?” she asked.
I held it out for her to take. She tipped the contents onto the bench, and sorted through them. There was a bright pink, lacy, suspender belt, a pair of bright pink fishnet stockings and, nestling in the bottom of the bag, a pair of crotchless knickers, also bright pink and lacy.
“My my, your partner really does have plans for you! she chuckled. “Right, strip!” she commanded, somewhat sternly. I was in my usual, comfortable, clothing - Hawaiian shirt, cargo pants, trainers and socks. I undid the shoes, kicked them off, and my socks swiftly followed. My shirt followed rapidly - I undid one button and pulled it over my head, letting it drop. There was a faint appreciative murmur at this. I hesitated slightly. My cock was at half-mast in my pants and I was a bit shy of stripping in front of a stranger - and what a stranger.
“Stop messing about! Anyone would think I’d never seen a naked man before.”
I took that to mean that she had, so I shrugged, undid my belt and dropped my trousers, revealing my half-hard cock tenting the silky black panties Lucy had insisted I wear.
“Oh, that looks pretty rude!” she said, colouring slightly. “Come on, off with those too!”
“Hey, that’s not fair!” I exclaimed, “You’re still fully dressed!”
“I’m the fitter, you’re the customer - it isn’t the usual practice for the fitter to strip off too!”
“I bet it isn’t the usual practice to be fitting lingerie on a man… Especially not a man with a hard-on.”
“Good point! Anyway, I can’t pretend that I haven’t been looking forward to your visit - in fact we drew lots to see who’d look after you when you arrived. Obviously, I won - as is only right and proper for the manageress.”
With this she undid a button and shrugged, so that her flowery dress slid off her shoulders and caught momentarily on her huge bust, but then fell and pooled around her feet.
“WOW!!” I exclaimed. There she was, clad in matching mauve stilettos, stockings, knickers, suspender belt, and bra… The latter only just managing to perform its role of restraining her tits - which were huge, and rippled seductively with every tiny movement. My eyes must have been out on stalks at the sight. She blushed slightly, and then swayed her hips, setting up a delightful quiver in her flesh. She wasn’t fat, but she was curvy in all the right places, and looked amazing.
“Like what you see?” she said, her voice husky. “Clearly you do!”
My cock had sprung to attention, almost instantly, tenting the fabric of the knickers alarmingly - I was quite surprised that they hadn’t just ripped, to be honest. She advanced towards me, those titties quivering so that I really couldn’t take my eyes off them. She grasped the sides of my panties and pulled them all the way down in one easy movement, planting a kiss on the head of my cock while she was down there, which bucked in response.
“Oooo, excited, aren’t we?”
“Just a bit! Well, honestly, who wouldn’t be? You’d give a monk a hard-on.”
“That would be fun.” she murmured as she stood up, grasping my cock in her hand, and squeezing it, making it twitch against her hand. I held her to me, and kissed her deeply on the lips; her mouth opened and her tongue snuck into my mouth. I felt for the clasp of her bra, and undid it, one hook at a time. My hands sneaked back around the front and slid under it, feeling the soft, pliable, weight of her massive bosom flowing out and down over my hands.
I groaned at the feel of her, my cock thrusting, dragging my hips toward her. She pushed my hands away, and stood back.
“Sit down!” she said, in a voice which brooked no dissent.
I sat, hurriedly, on the bench. She proceeded to strip, slowly, deliberately, seductively; first taking off the redundant bra, and throwing it to me. Catching it, I pressed it to my face, and hummed my satisfaction.
She unclipping the front of one suspender, then half-turned to show me the other as it curved over her generous arse. She looked at me, and puckered her lips as she undid that one too, before rolling off her stocking and kicking it at me. It fell over my face, warm, silky and smelling faintly of her. The other stocking followed, the same way. I was all hers, totally mesmerised by this display. Then she unclipped the suspender belt and dropped it. With one hand I grasped all the feminine attire she’d handed me, while the other slowly, deliberately, wanked my achingly hard cock.
She put fingers in either side of her panties and, turning again so that I had the perfect view of her big, round, arse, slid them slowly down. They caught in her crack, and then sprang free, affording me a brief glimpse of her pussy. She turned, stepped out of them, walked towards me and thrust them under my nose.
“Look what you’ve done!” she said, “they’re all wet and sticky now!”
I dropped everything else, grasped them in my hand, held them to my face and inhaled deeply; they were warm, damp, and smelled absolutely heavenly.
And then her spell was broken, I was on my feet, and we were all over each other - kissing, licking, fingering, wanking. She was amazing - like nothing I’d ever felt before - her flesh so smooth, so soft, her pussy so slick and creamy - I brought my fingers to my mouth and licked off some of her delicious cunt cream. All told she was, well, womanly.
Woman to the max.
She pushed me back, so I had no choice but to sit, and straddled me, sitting down on me, whilst deftly guiding my cock into her love tunnel. She lifted her huge boobs towards my face, and as we began to thrust, I bent and began to suck on her burgeoning pink nipples, first one, then the other, while my hands grasped her buttocks and encouraged her into a rising trot.
In almost no time at all, she and her ample charms proved too much and, groaning, I pumped the entire contents of my balls deep into her pussy in spurt after spurt, uncontrollable thrust after uncontrollable thrust.
“What about me? she wailed, “What about my turn?”
“Sorry - I couldn’t help it… You’re far too sexy for the likes of me.”
“You’ll have to finish me with your mouth.” She stood and placed one foot on the bench beside me, which opened up her thighs and put her pussy on display - open, eager and soaking with our combined juices. I slid down a little, and then I could reach her pussy with my mouth. My cum was beginning to ooze thickly out of her cunt and down her alabaster thigh. I buried my face in her crotch, and licked and sucked, and sucked and licked, at the same time fondling her arse with my hands. Soon she began to quiver and pant. Her arousal was so exciting that even though I’d only cum mere minutes before, my cock was beginning to stir again already. Her movements increased in ferocity, and then she made a whole series of little chirping cries as her pussy spasmed around my tongue, covering my face in her cream as she came, almost collapsing on top of me. We wound up clinging to each other on the bench as she came down from her high.
“Fuck me, that was intense.” she said.
“It was amazing, just like you.” I agreed.
“We need to get you dressed!” she said, suddenly, picking up the knickers. “Pop these on.”
I stood and pulled on the panties. They felt amazing, sliding smoothly up my legs. She took hold of my half-hard cock as I pulled them up, and threaded it through the slit in the crotch, and then gently eased my balls through too. My cock was now fully hard. She giggled.
“That looks absolutely obscene,” she chuckled, “I love it. Quick, let’s get the rest on!”
She fastened the suspender belt around my waist and helped me roll the stockings on, deftly clipping the suspenders to the tops and adjusting the straps.
I stood there, in the middle of the fitting room; seeing myself in each of the mirrors.
“Well… Look at you! What a sexy sight!”
And, indeed, yes, it felt, and looked, sexy in an oddly perverted way - the juxtaposition of silky feminine undergarments, and my slim but muscly legs, not forgetting my erect cock and balls protruding so rudely from the slit in the material, created a truly strange sight…
Which I found a huge turn-on.
Just at that moment, we heard a knock.
“You in there Hannah?” came Yolanda’s voice, as we heard a key turning in the lock. The door opened, and Yolanda’s face appeared around it. A look of shock flashed across her face momentarily…
“WOW Phil! You’re quite a sight, and no mistake!” she exclaimed, the look of surprise replaced almost instantly by one of pure lust.
To be continued…