tagTranssexuals & CrossdressersA Conversation with a Lady

A Conversation with a Lady


This story was inspired by Gemsissy and her wonderful shopping trips...


A select lingerie shop in a small northern English market town. The shop front reads 'Cherie.'

I walk in and I'm surrounded by wonderful things by Lejaby, Aubade, Lise Charmel. A stylish woman is behind the counter; she's mid-40s, slim, blonde, tall. She has tanned skin, expertly-applied makeup with natural-looking peach-pink lipstick. She's wearing a tight-fitting, beige ribbed sweater and black trousers. She's on the phone and I notice her French manicured, square-cut white nails. I notice a pack of Silk Cuts on the counter with a lighter on top.

She talks to a voicemail and she has a calm, soft voice and a Manchester accent. "Yes, it's Cherie Lingerie. This is Cherie speaking. I'm just letting you know your order should be here tomorrow. I'll ring to confirm when it arrives. Thank you..."

I pick up an impossibly flimsy, sheer red bra as she smiles towards me. "Hello..."

"Good morning," I smile back.

"If there's anything specific you'd like to see, please ask..."

I replace the amazing bra. "I'm looking for a basque; something luxurious and exclusive... Black lace, embroidered flowers..."

"Ok," she smiles, "perhaps something like these?" She indicates a couple on a rail. "Have you any idea of the size?"

This is the bit I always find so enjoyable. "Actually, it's for me... I'd like to try a couple on, if that's OK?"

She pauses momentarily, her manicured fingers clasped together at shoulder level in a very feminine gesture. "Yes, that's fine..." she smiles, her composure regained. She eyes me up. "You'd be..."

"My bra size is 40B, but I wear forms to bring me up to a D or DD cup. I have them with me..."

"Ok," she says quietly as she selects a few in my size. "Is it for a special occasion?"

I smile. "Yes, a party... I'll be wearing it under a silk bridesmaid dress..."

She smiles and her eyes widen. "That sounds exciting..." She passes me a couple of gorgeous basques. "And maybe as it's such a big day you might like to try this one..."

"Oh, that is so pretty..." I feel my face flush as she hands me this almost invisible little garment. It's light as a feather, completely transparent except for the lace trim, pink and orange embroidered flowers and vines, and little bows on the suspender straps. The bra cups are completely see-through.

"Isn't it just," she purrs. I want to kiss her. "It is expensive, it's true, but just look at it... I was about to have a coffee; would you like one?" The shop is otherwise empty and she makes lattes for us while I take three basques into the large changing room. I undress, apart from the essential strong, male underwear that just about preserves my modesty, and put on one of the basques. It's by Lejaby, gorgeous and a wonderful fit.

"Could you just lace the back for me, please," I ask Cherie as I hear her outside with the coffees.

She comes in through the curtain. I have the forms in place in the cups and she says "That looks sweet on you!" She stands close behind me and begins to pull the laces tight. I can hear her breathing and taste a faint hint of cigarettes on her breath. "I bet you're quite tall in heels... so, if you're the bridesmaid, who is the bride?"

"My wife... she's going to be wearing a wedding dress and bridal lingerie. It's more of a party than a ceremony, though."

"And the groom?"

"Anton, her lover. Our lover..."

She finishes lacing and takes a step back as I look at myself in the mirror. It feels and looks fabulous.

"It sounds like quite an interesting day... maybe not a family occasion!" We both grin at this.

"I agree, it must sound screwed up." I undo the ribbon, and start to wiggle out of basque No1. "I'll have to tell you about it, some time..." I hand the Lejaby back and whisper that it's gorgeous. I'm naked but for my underpants, and have an obvious erection, but, a worldly businesswoman, she is comfortable with me in that state. She hands me another basque; it's by Aubade and has more satin and more frills.

This one fastens at the front, and we're eye to eye as she helps me. "Why don't you tell me about it now," she smiles.

I take a sip of my coffee. "Well, Anton..." I can't think of an alternative word: "Fucks both of us." I glance at her but she isn't phased; she just appears genuinely interested. "It's an unconventional arrangement. He's very nice to my wife, takes her to dinner and treats her with lovely things. They both like me to dress in female clothes, in the bedroom and I also go out with my wife shopping as a girl, and to clubs and select swinger parties."

The Aubade is more structured, and more burlesque. it feels gorgeous as well, but in a different way; I wouldn't be happy with it under the dress, as it needs to be shown off.

"After the party we're flying off to a villa on the Amalfi coast for a week. We've joked that it's a honeymoon, which is why we're having the party, and the dresses and everything. Anton doesn't live with us, yet, but we want to see if we think it will work out, us all living together."

She takes a sip of her coffee, smiling. "Ok..."

I have a good look at myself in the Aubade and start to unhook. "Also, usually I don't get to dress up very often; to play with my wife and Anton, parties and very occasionally a weekend, but I'll be a woman for a whole week." I'm grinning from ear to ear and flushed, and she responds with her own grin.

"All the things that a glamorous woman like you would do. I'll sip cocktails by the pool in a swimsuit, red lipstick and heels; I'll sleep in a pink chiffon negligee, I'll spend all day in silk lingerie with a pretty made-up face."

She chuckles and sips her coffee. "when you say it like that, it can be quite fun being a woman..."

"So the week will be a try out in that respect, also..."

I hand her the Aubade which she puts back on its hanger. There's a pause as we sip our drinks; I glance at her to see if she got the meaning of that point, but unsure, I explain anyway. "We're going to see if we'd like me to live as a girl all the time." As if to give her approval to this, she hands me the floaty, sissy Agent Provocateur with a naughty smile.

I start to pull it on; there's virtually nothing to it, and I feel more than naked. She starts to fasten the tiny hooks, and I feel a stiffening. "All the time... would that mean surgery?"

"Not down below. But definitely breast enhancement. My wife and Anton both like big breasts; she's a 38D, and they'd like me to be a DD or E cup." It's thrilling to be dressed in this flimsy garment while discussing the idea of having big boobs, especially with its transparent cups. "I think I can be more stylish with C or D..."

"It does sound exciting, if that's what you want..."

"I'd have to leave my job; I'd be a kept woman!" I blow a kiss and we both laugh gently. "I love the thought of wearing a bikini. And I'll definitely be buying that red bra!"

The basque looks sensational and I know it's the one. It does feel a little tight across the back, I tell her. "The Agent Provocateur," she explains with her naughty smile, "is designed to be worn with heels. You'll be surprised what the subtle change in posture does to the fit."

I smile. "I actually bought some with me! I was hoping I'd get a chance to walk, see how it feels... Can I see some of your silk stockings, please?" I would never wear holdups with a basque like this; Cherie knows this, instinctively, and doesn't fetch any.

"These are the best... 10 denier." I unwrap them; they're gossamer-fine, barely black and seamed, with a very narrow lace band. I sit down on a chair and point my toe, sliding a stocking up my shaved and moisturised leg.

"Oh, these are divine. I'll take four pairs of these."

"I usually close about now on a Wednesday," smiles Cherie. "No, don't rush. Have a walk round and see how it feels; I don't have to be anywhere else."

While she turns the sign to 'closed' and locks the door, I attach the clips and step into my patent black sandals. They're by Dior with diamantes and a 3 1/2 stiletto heel, and I love them. I heel-and-toe few steps and the fit of the basque instantly makes sense, as my back arches and my posture improves. "Wow, I see what you mean! It feels totally different..."

She watches me from behind the counter. "You've clearly done that before... Why don't you take your time and have a stroll round the shop? I'm going out to the yard for a ciggie; I'll have to close the door to keep the smoke away from the merchandise, but take your time..."

The door closes behind her. I stroll, watching myself in the mirror. My shaved body; the silicone forms filling the cups nicely; my short-bobbed, platinum-blonde fringe falling over my eye, and all that amazing, glamorous black lace lingerie. I can make out Cherie in the yard, arm across her chest, an endless stream of cigarette smoke rolling from her mouth. A mature woman, who smokes regularly will take about 3 minutes. I release my cock from my male underwear and step out of them. I walk slowly through the aisles, trailing my arms to feel silk, satin, lace on my skin. The rustle of fabrics and clink of plastic coat hangers is like music.

I take the red bra from the rail and brush it against my erection. Finding the matching knickers, I pull back my foreskin, pressing the head of my cock into the gusset of the flimsy panties. I close my eyes and imagine a glamorous woman- possibly even Cherie- pulling them on, her vulva in contact with the traces of my precum. Every urge in my body wants to ejaculate into them, but I put them back on the rail. I spot a glorious pink chiffon robe and put it on, wrapping it around me as I see Cherie walking back across the yard, crushing her cigarette underfoot as she exhales, in one fluid action.

I tell her I'll definitely be taking the basque, the robe and four pairs of the divine stockings. "I really don't want to take this pair off... do you have the suspender, from the same range as the basque? Oh, and the panties in a 12-14." I give her a wink. "Do you have ouvert?"

"Naughty. Of course we do..."

Back in the changing room, I take off the basque, replacing it with the prissy little suspender belt. I couldn't possibly wear the ouvert panties right now; neither do I want to put on cotton underpants. I had anticipated this so I have black lace boy shorts in the bag. I get dressed again, in my white jeans and striped T-shirt with a slim fit, cropped grey hoodie. Cherie has the bill: "Right. Agent Provocateur Signature basque is £280; 4 pairs of silk stockings at £38 each is £152; Signature suspender is £100 and ouvert panties are £68. Pink chiffon robe is £80." She says quietly "Total is £680..."

I produce my platinum card efficiently; Cherie doesn't know my monthly budget for lingerie and shoes alone is £1000. I sit on a chair to put on my converse shoes but I don't; they say femininity is a state of mind, and surrounding oneself with such delightful lingerie has put me firmly in that mindset. I put the Dior heels back on and fasten the tiny buckles.

I stand up and giggle at Cherie. "Your shop is adorable, darling." I take out my pink lipgloss and apply a coat in the mirror; my Mercedes is parked just around the corner, and I'm sufficiently femme, and androgynously dressed, to pass. "I think I might just have to come and work for you..."

Cherie giggles back, thrilled. "Maybe you'd like to invest? I was thinking of maybe upsizing..."

I look at myself in a full-length mirror, putting on my RayBan mirrored aviator shades as she hands me a large paper carrier bag containing my purchases. "Cherie, darling," I say, kissing her on the cheek, "You mustn't change this delightful shop one bit!"

The bell tinkles as I leave the shop, the sound of a sissy angel getting her wings.

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by Anonymous

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by dacoach4408/26/18

so cute

Would love to see the sissy play with the owner.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by OpenMouth08/08/18

Thanks for the comments...

Yes, I liked writing this. I'm too masculine to be the central character, but I do fantasise about being young, blonde, slim and adventurous, with a naughty streak!

I agree that there doesn't have tomore...

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by yukonnights01/28/18

Nicely written. It just goes to show that some stories don't need racy sexual escapades to be meaningful. A simple day in the life of an average person can also be a peek into another world. There'smore...

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by cdCindy101/11/18

loved this story

I loved this story as it's exactly what I would love to do at a local women's clothing store. However, I'm still in the closet and there may be people who know me in my male life. I will have to go outmore...

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