Shopping Spree Gone Wrong: Mistaken for a Woman – Crossdressing Stories

welcome to Miss Scarlet Subscribe and don't miss out on Patreon Have fun The morning sunlight greeted Robert casting a soft glow upon the clutter of fashion cataloges on his coffee table It was a clandestine collection one he'd accumulated over days studying sizes styles and trends Each page a road map to his hidden desires His fingers unsteady with anticipation rad through his cropped hair as he gazed around the apartment his haven Here 20 m from the life he publicly led he'd practiced perfected and pondered the strides and heels the art of makeup application all preparing for this very moment tags still whispered promises from the sundress he'd selected hanging like a silent invitation The blonde wig an impeccable disguise stared back with silent scrutiny Across the room the strappy sandals in that elusive size 11 women's a rare gem from an online boutique beckoned As he stared at his own reflection Robert whispered the words that held the weight of a lifetime just this once just to know what it feels like After shaving meticulously and applying foundation that had taken three YouTube tutorials to get right Robert slipped the sundress over his head The soft fabric caressed his skin in unfamiliar ways as it settled into place The dress white with delicate pink and purple flowers hung a bit loosely around his waist but otherwise fit his tall frame surprisingly well He secured the blonde wig carefully adjusting until it framed his face naturally A touch of mascara some blush and a swipe of pink lipstick completed the look The strappy sandals added 3 in to his height making him tower at 6'3 "Hello," he said to his reflection voice pitched higher than normal "I'm Charlotte. " The name had come to him days ago Elegant but not flashy perfect for a first outing His fingers brushed the car keys on the counter Northbrook Mall waited 40 minutes away far enough that the chance of running into someone he knew approached zero His heart pounded against his ribs as he stepped outside scanning the hallway before hurrying to the elevator The drive passed in a blur of anxiety and second thoughts What if someone recognized him what if he looked ridiculous what if the women at the mall could instantly tell he didn't belong each traffic light offered another opportunity to turn around Yet something propelled him forward The mall parking lot loomed ahead Robert chose a space far from the entrance taking deep breaths before checking his appearance one final time in the rear view mirror Just a few hours he promised himself Walk around maybe buy something small then go home The walk across the parking lot proved the first test The sandals while stunning weren't designed for someone unaccustomed to their structure His ankles wobbled slightly with each step forcing him to slow his pace The automatic doors parted Cool air conditioning rushed to greet him along with the ambient sounds of the mall conversations distant music the clacking of footwear on tile Robert no Charlotte now stepped inside eyes downcast waiting for shouts of recognition or mockery that never came Nothing happened People streamed past without a second glance A group of teenage girls giggled nearby but it had nothing to do with her A security guard nodded politely The world didn't stop spinning Emboldened Charlotte lifted her chin and headed toward the directory Women's clothing stores beckoned from every wing Her nervousness gradually melted into excitement as she mapped a route Nordstrom first then perhaps the boutiques along the east corridor The women's department at Nordstrom stretched before her in a landscape of colors and textures Charlotte trailed her fingers along a rack of silk blouses savoring the sensation Another rack held cardigans in autumn colors and beyond that skirts of varying lengths awaited exploration May I help you find something ma'am the voice startled her A saleswoman in her 50s with immaculate makeup and a black pants suit smiled expectantly The word ma'am hung in the air between them The first time anyone had addressed Charlotte as a woman I'm just browsing Charlotte managed voice catching before she adjusted to a higher pitch Thank you Of course We're having a sale on summer dresses if you're interested Second rack to your left The saleswoman moved away leaving Charlotte in a state of quiet triumph Her first interaction had gone smoothly No raised eyebrows no suspicious glances She'd been accepted without question The recommended sail rack proved irresistible Among the offerings hung a beautiful navy blue dress with white polka dots Charlotte checked the size 14 and lifted it from the rack The price tag showed a significant discount "That would look lovely with your height," came the saleswoman's voice again "Would you like to try it on? " Panic fluttered in Charlotte's chest "A fitting room meant confined spaces potential questions exposure.

" "I think I'll just take it," she replied "I know my size Are you sure we want our customers to be completely satisfied Something in the woman's gentle persistence broke through Charlotte's hesitation Perhaps this was part of the experience the trying on the assessment the ritual of women's shopping that she'd only observed from afar Actually yes I'd like to try it on The fitting room attendant a young woman with vibrant purple hair handed Charlotte a numbered plastic card "Let me know if you need anything else," she said with casual friendliness Inside the small cubicle Charlotte hung the blue dress on a hook and studied herself in the three-way mirror The floral sundress had served its purpose but seeing herself fully transformed from multiple angles brought a rush of emotion The blonde wig framed her face softly and the makeup though amateur effectively softened her features She slipped out of the sundress carefully avoiding disturbing the wig and eased the polka dot dress over her head It fit perfectly across the shoulders and chest tapering nicely at the waist before flowing to just below the knee The saleswoman had been right It complimented her height beautifully Charlotte emerged from the fitting room with newfound confidence I'll take it she told the saleswoman who beamed approvingly Excellent choice Would you like to wear it out the opportunity to leave the old dress behind felt symbolic Yes please At the register Charlotte presented her credit card Robert Mercer embossed on its surface A moment of panic seized her until the cashier processed the transaction without comment Of course people used others credit cards all the time spouses partners family members With the sundress tucked into a Nordstrom shopping bag Charlotte ventured deeper into the mall Each step in her strappy sandals grew more natural Her posture improved shoulders relaxed Store windows reflected a tall blonde woman with a growing smile The cosmetics counter at Macy's drew her next Display cases glittered with promises of transformation Foundations eyeshadows lipsticks in every conceivable shade Charlotte approached cautiously admiring the artful arrangements Looking for anything specific today a makeup artist with flawless contouring and dramatic eyeliner appeared at her side I need Charlotte hesitated I need everything really I'm just beginning to build my collection The woman Tiffany according to her name tag brightened A blank canvas My favorite What's your skin type the consultation lasted 45 minutes Charlotte emerged with a bag containing foundation that actually matched her skin tone brushes of various shapes and sizes neutral eyeshadows for beginners and a lipstick in dusty rose that Tiffany swore would bring out the warmth in your complexion Confidence growing with each purchase Charlotte decided to brave the food court for lunch She selected a salad from a Mediterranean stand and found a small table near the center fountain The art of eating carefully to preserve lipstick proved challenging but manageable 3 hours into her mall adventure Charlotte had accumulated four shopping bags and countless small victories She'd successfully navigated women's clothing departments makeup counters even public restrooms slipping into a stall quickly and efficiently Not once had anyone questioned her presence or identity The lingerie store loomed ahead Victoria's Secret with its pink striped facade and window mannequins in elaborate bras and panties Charlotte hesitated This seemed a boundary too far too intimate for her first outing As she turned to head toward the exit planning to end the day on her current high note a familiar voice froze her in place Charlotte is that you the name registered before the voice's owner did Charlotte turned slowly confusion turning to horror as recognition dawned Standing before her shopping bags in hand and head tilted inquisitively stood Elaine Westfield his boss's wife Impossible scenarios raced through Charlotte's mind How could Elaine possibly know the name she'd selected for herself how could she recognize someone who didn't exist until today i'm sorry Charlotte managed I think you might have me confused with No no it must be you Elaine insisted stepping closer Charlotte from the hair salon on Maple Street You did my color last month the Auburn Highlights Relief flooded through Charlotte so intensely her knees nearly buckled Mistaken identity The simplest explanation I'm afraid I'm not Oh Elaine's hand flew to her mouth I'm so embarrassed You look exactly like my stylist Uncanny resemblance Please forgive me No need to apologize Charlotte assured her preparing to make a polite exit I'm Elaine Westfield by the way She extended her hand My husband Thomas runs Mercer Architectural Solutions The mention of her workplace her actual name embedded in the company title sent a fresh wave of panic through Charlotte She shook Elaine's hand weakly Nice to meet you I'm Charlotte Charlotte elaine prompted Charlotte Wilson The surname came from nowhere Perhaps a street sign glimpsed on the drive over Such a pleasure Are you shopping for anything special today common courtesy demanded engagement however brief Just picking up a few things Summer refreshes for my wardrobe Your dress is absolutely darling Elaine commented gesturing to the navy polka dots Where did you find it nordstrom They're having a sale I should have checked there first I've been looking for something for the company lunchon next week Elaine's eyes lit suddenly Actually Charlotte this might sound forward but would you be interested in joining us it's our annual ladies lunchon for executives wives and female staff Thomas mentioned their short on attendees from the design department this year The invitation hung in the air like a suspended anvil Charlotte's mouth opened but no words emerged "It's at Laameon downtown next Thursday at noon," Elaine continued mistaking Charlotte's silence for consideration "The food is divine and the company is even better A chance to network with the ladies of MAS. " "I I don't actually work at Mercer," Charlotte finally managed Elaine waved dismissively Doesn't matter We always welcome friends of the company Thomas is always saying we need fresh perspectives She pulled out her phone Give me your number and I'll text you the details Trapped in the escalating charade Charlotte recited her personal cell number the one that also belonged to Robert Mercer MAS's senior design coordinator who would absolutely be expected at work during the lady's lunchon Perfect Elaine beamed tucking her phone away I'll also add you to our group chat The ladies will adore you We need more tall women to balance out all the petite ones I'm not sure I can No excuses It'll be wonderful Oh look at the time I must run Thomas is expecting me for dinner with clients Elaine touched Charlotte's arm So lovely meeting you Charlotte See you Thursday Before Charlotte could formulate a response Elaine disappeared into the stream of shoppers leaving disaster in her wake The drive home passed in a days of panic Charlotte now transforming back into Robert with each mile replayed the conversation repeatedly By the time he reached his apartment the blonde wig tossed onto the passenger seat and lipstick wiped away with a tissue he'd counted at least 12 ways the situation could implode Inside his apartment Robert dumped his shopping bags on the couch and collapsed beside them His phone buzzed with an incoming text Hi Charlotte It's Elaine Westfield So wonderful meeting you today Here's the info for Thursday's lunchon looking forward to it Below the message lay all the details time location dress code business casual or smart sundress and a list of expected attendees that included the CFO's wife the VP of marketing and Robert's own administrative assistant Denise A second text arrived moments later I've added you to our group chat Ladies please welcome Charlotte Wilson to our lunch next week Robert stared at his phone in horror as notification after notification rolled in Welcome messages from women he knew professionally women who worked alongside him daily women who had no idea that Charlotte was sitting in his living room wearing a navy blue polka dot dress and strappy sandals The charade had spiraled beyond control If he didn't attend Elaine would surely mention the snub to Thomas who might mention it to Robert himself If he did attend the consequences were unthinkable He paced the apartment dress swishing around his legs The new makeup purchases sat accusingly on his coffee table The blonde wig stared from the passenger seat of his car visible through the living room window An idea formed slowly outrageous terrifying but possibly the only way forward Charlotte would need to attend the luncheon Charlotte would need an identity a backstory a reason for her connection to MAS That wouldn't raise suspicion And most importantly Charlotte would need auburn hair not blonde to ensure no connection to the woman in the mall if Elaine mentioned their meeting to Thomas Robert reached for his laptop one week to prepare for the performance of his life The following morning at work Robert listened attentively as Thomas Westfield discussed upcoming projects in their weekly staff meeting Before we wrap up Thomas said "Ela wanted me to remind everyone about the lady's lunchon next Thursday Apparently attendance is looking sparse from the design department. " Robert cleared his throat Actually sir I believe my cousin Charlotte might be attending She mentioned meeting your wife yesterday Thomas brightened Charlotte Wilson yes Elaine mentioned her Your cousin eh elaine was quite taken with her Said she'd be a wonderful addition Charlotte's visiting from Robert hesitated Portland She's also in design different firm I thought it might be good for her to network while she's in town Excellent initiative Robert Always good to keep connections in the industry strong The lie bought Robert temporary safety Now he just needed to ensure that Robert and Charlotte never needed to be in the same place at the same time The weekend provided crucial preparation time Robert drove to a different mall two counties away to purchase an auburn wig high quality with natural looking layers that fell just below his shoulders He practiced walking in his heels until blisters formed then healed He watched countless makeup tutorials focusing on techniques to soften his jawline and accentuate his eyes He drafted a detailed backstory Charlotte Wilson 38 senior designer at a boutique firm in Portland visiting her cousin Robert for 2 weeks divorced no children specializing in commercial interior spaces Enough specific details to sound authentic vague enough to avoid easy verification By Wednesday evening the transformation had evolved significantly from his mall debut The auburn wig suited his coloring better than the blonde and his makeup skills had improved remarkably The navy polka dot dress had been pressed and a delicate silver necklace added to complete the ensemble "Hello," he practiced in the mirror voice pitched to what he hoped was a natural sounding feminine range "I'm Charlotte Wilson Robert's cousin from Portland.

" Thursday morning arrived with nauseating intensity Robert called in sick to work a first in his seven years at Mayas Denise his assistant sounded concerned "Nothing serious," he assured her "Just need a day to recover Probably back tomorrow. " "Take care of yourself," she replied "I'll reschedu your meetings. " "Oh and I'll see your cousin at the lunchon today Mr Westfield has been talking her up to everyone.

" Robert's transformation into Charlotte took nearly 2 hours Each detail required perfection The auburn wig styled in loose waves Makeup applied with surgical precision The navy dress accessorized with the silver necklace and a matching bracelet A light floral perfume completed the effect The drive to Lameison downtown felt like heading to the gallows Charlotte rehearsed names relationships company structure details anything that might arise in conversation She parked three blocks away not wanting to risk being spotted emerging from Robert's distinctive blue sedan Lameon's elegant facade loomed ahead Through the windows Charlotte could already see women gathering in the private dining room Women who knew Robert Mercer as a colleague a supervisor a professional acquaintance women who would now meet his cousin Charlotte Just 2 hours she whispered to herself Smile be pleasant keep conversation focused on them not you The matraee greeted her warmly Name for your reservation madam I'm with the Mercer Architectural Solutions lunchon Charlotte replied pleased with how steady her voice sounded Ah yes right this way Most of your party has arrived The private dining room buzzed with conversation 15 women of various ages sat around an elegantly set table cocktails and appetizers already being enjoyed Elaine Westfield spotted Charlotte immediately rising from her seat with a delighted expression Charlotte you made it She embraced Charlotte warmly the scent of expensive perfume enveloping them both Everyone this is Charlotte Wilson the wonderful woman I met shopping last week She's actually Robert Mercer's cousin visiting from Portland All eyes turned to Charlotte Among the faces she recognized Denise her own assistant along with several departmental secretaries executives wives and the head of human resources who had processed Robert's employment paperwork 7 years ago Such a pleasure to meet you all Charlotte managed taking the empty seat Elaine indicated directly across from Denise Robert called in sick today," Denise said immediately "I hope it's nothing he might have passed to you. " Charlotte's heart stuttered "Oh no He was fine when I left this morning Perhaps something he ate disagreed with him. " "Men are such babies about stomach upset," laughed the CFO's wife breaking the tension "My husband acts like he's dying if he gets indigestion.

" The conversation shifted to general agreement about men's poor handling of minor illnesses buying Charlotte precious moments to settle her nerves A server appeared at her elbow Sparkling or still water madam sparkling please Charlotte unfolded her napkin placing it carefully on her lap as she'd practiced So Charlotte began the HR director Patricia Mueller Elaine tells us you're also in design Which firm in Portland wilson and Associates Charlotte replied smoothly Small boutique firm specializing in commercial spaces Any relation to the Wilson in the name my ex-husband Actually I kept the name professionally after the divorce The answer seemed to satisfy Patricia who nodded sympathetically The first course arrived a delicate salad with goat cheese and candied walnuts Charlotte watched the other women for cues on which fork to use mirroring their movements "How long have you been in design?