tagTranssexuals & CrossdressersHostess with the Mostest Ch. 02

Hostess with the Mostest Ch. 02


Chapter Two - Progress and Problems

Candi awoke late the next day with the sun streaming in through the window. For a few seconds she thought she had dreamt the whole thing. Then she noticed her pillow was stained with lipstick, mascara and eyeshadow and she smiled. She could still taste Michelle's sweet mouth on hers.

She rolled over and tried to catch more sleep but her mind was racing. She had so much to do!

First thing was to strip off the lingerie and remove the makeup. After showering Chris felt all vestiges of Candi were gone and he was a little disappointed but pragmatic; there was so much to do and he couldn't do them dressed in a nineteen sixties airline hostess uniform.

He checked out the list Michelle had helped him make the night before. The first thing he needed was more female attire. Clothing he could wear out and about. Not Op Shop stuff but a few good quality items which Michelle had written on a list for him.

Michelle had advised him to go to the Debenhams on the High Street in Chelmsford and to ask for the supervisor of the ladies department, Stephanie Parker. Michelle had also told him to take some makeup so he could transform while there and venture out for the first time. Debenhams was only three streets over from the hairdresser where Michelle had made an appointment for 'a Ms Candace Pops' and it would be Candi's first outing. Chris was nervous but knew that if he wanted to pass convincingly enough to get the stewardess job it was a task he would need to master.

He felt very self conscious when he entered Debenhams but he found the plump but attractive supervisor of ladies apparel section at her station. Chris introduced himself and was rewarded with a beaming smile.

"I'm Stephanie pleased to meet you. Michelle Murphy called me last night and told me you would be coming to see me today," she gave him a genuine smile.

"I know that you're new to this but don't be afraid; I was the one who helped Michelle pick out her first everyday ladies clothing back when she was still Cherri Pops and just starting out. I have reserved a private fitting room just for you so that we can be discreet. The room has floor to ceiling walls for complete privacy, a full-length mirror and a nice table and padded bench for your comfort. Come on over and I'll get my tape measure and we can get started."

"Oh my god; thank you so much," Chris blushed.

Chris stood in the fitting room and stripped down to his underpants while Stephanie measured him and had him put a foot into a Brannock foot size measuring device so she could accurately assess his shoe size. Then she bought him a coffee and had him sit on the little bench.

Chris handed Stephanie the list that Michelle had helped him write.

"This is what I need," Candi said.

"Michelle told me that you intended to transform while you're here so you can leave as a lady. Why don't you do your makeup now and I'll be back shortly with some lingerie, then we can sort out clothes, shoes and accessories for you."

As soon as Chris started applying makeup his mind tripped over and he became Candi. He was quite amazed how suddenly the divergence occurred. It was a little awkward putting on makeup in the full-length fitting room mirror but she did a half decent job.

There was a soft rap at the door and Candi opened it to find Stephanie outside with a shopping basket full of lingerie and other accessories. Candi let her in.

"Wow you look gorgeous; Michelle taught you well...Candi isn't it?" Stephanie asked.

Candi nodded modestly.

"I've got some nice knickers and brassieres for you. One pair each of black, white, and red; all satin with lace trims. I also have some pantyhose in black, grey, and flesh tones. Let's get you into a pair of those first so we can tuck this fellow between your legs out of the way," Stephanie playfully tugged at Candi's flaccid penis through her briefs.

Candi shucked off her man's briefs and sat on the little bench and allowed Stephanie to help her put on a pair sheer grey pantyhose. Candi again marvelled at how delightfully sensuous the sheer hose felt on her legs and buttocks. Stephanie even helped her tuck her penis between her legs pulling the gusset of the hose taut to keep it tucked away. The gentle caress of Stephanie's cool fingertips on her nylon-clad member caused it to become slightly turgid and Candi blushed.

"Step into these," Stephanie knelt down and held open a pair of black satin full-cut panties.

Candi shivered as they glided up her legs and Stephanie pulled them snug around her buttocks and groin. Stephanie smoothed the wrinkles out of Candi's pantyhose and panties so the fabric was tight and sleek. Candi's penis was now quite ductile and she was glad it was tucked away between her legs. She figured that once she got used to wearing such alluring and sensual underwear that she would stop reacting like this every time she dressed enfemme. Michelle had told her that the thrill of stepping into such delightful apparel never really went away but it did diminish over time with perpetual daily exposure.

"Mmm that's working well; no tell-tale bulge, the front of your panties are quite smooth," Stephanie lightly ran her fingers across the front panel of Candi's panties and Candi suppressed a groan.

Stephanie stood behind Candi. Very close behind her. Stephanie was dressed in a navy blue skirt, white satin blouse, black high heels, and taupe stockings. Her makeup was quite heavy and Candi could smell her perfume. She was very attractive for a larger mature lady and her close proximity and constant touching was making Candi nervous and horny.

"Arms out and I'll do up the clips on your bra," Stephanie whispered.

She was so close that Candi could feel her breath in her ear.

Stephanie clipped the bra strap behind Candi's back and untangled the shoulder straps. Her fingers found the cups of Candi's brassiere and slipped inside.

"Mmm. Small but firm," Stephanie pressed herself against Candi's back, her fingers flicking Candi's nipples.

"What are you doing! Oh my..." at first Candi was alarmed but when Stephanie began to nuzzle her neck, her fear turned to lust.

Stephanie kissed Candi on the side of her face and Candi turned her head and locked lips. Candi and Stephanie were both enamoured by the taste of their lipstick and the feel of their soft lips. Stephanie slipped her tongue into Candi's mouth, probing and exploring. Candi pushed her panty-clad buttocks into Stephanie's groin and wriggled her bottom whilst Stephanie caressed Candi's nipples.

Candi spun around. Dressed only in hosiery, panties and bra she felt a little vulnerable but ever so sexually aroused and she passionately kissed Stephanie pulling her close.

The two beautiful ladies kissed and caressed in the fitting room, oblivious to the outside world.

Stephanie's fingers slid down to Candi's thighs and stroked them gently. Candi relished the feel of her silken-clad thighs being caressed, little sparks of pleasure emanated from her thigh to her groin and her semi-tumescent penis began to fully harden. It was actually quite painful squished between her legs as it became erect.

Stephanie sensed Candi's discomfort and she smiled.

"Let me help you with that darling," she reached inside Candi's pantyhose and freed Candi's rigid member from between her legs.

Candi's hard cock sprang forward, still encased in the gauzy nylon and satin of hose and knicker. Stephanie gripped it and squeezed.

"Ohh!" Candi moaned.

Stephanie began to slowly stroke the gossamer clad member as she kissed Candi. She was becoming wet herself and she sighed when she felt Candi's hand slide under her skirt. She was wearing stockings and Candi's fingers stroked the slippery welts and then explored the soft creamy skin above her stocking tops.

Stephanie opened her legs encouraging Candi to explore further and she did. Candi's fingers found the crotch of Stephanie's nylon panties already sodden with her juices. Candi's slid a finger into the silky material and felt Stephanie's labia lips part and found her hooded clitoris erect. She softly rubbed the gauzy nylon on Stephanie's clit and Stephanie's knees began to buckle with pleasure.

"Oh yes sweetheart that feels so wonderful," Stephanie gasped.

"You too darling," Candi whimpered as Stephanie massaged her throbbing cock through her panties and hose.

Stephanie released Candi's cock briefly and rolled down Candi's pantyhose gusset and pulled down her panties, exposing Candi's erect member which she gripped and squeezed; feeling the hard sleek flesh throb in her hand.

Candi pulled down Stephanie's panties and pushed her against the wall of the cubicle. They kissed and caressed until they were both close to climax. Candi lifted Stephanie's skirt and Stephanie lifted herself on her tiptoes and lowered her sopping cunt onto Candi's hard cock.

Candi placed her hands under Stephanie's buttocks and Stephanie raised her feet off the floor and wrapped her stocking-clad legs around Candi's thighs. Candi supported Stephanie's weight by cupping her buttocks and pushing her back against the fitting room wall as she began to fuck the gorgeous shop assistant.

Stephanie felt Candi's rigid, throbbing, cock deep inside her and Candi's pelvis pressed against her clitoris; her whole sex was tingling with intense pleasure. Her cunt was sodden. She contracted her vaginal muscles and gripped Candi's cock in her velvet tunnel.

Candi felt Stephanie's vagina pulse and throb and grip the sensitive glans and shaft of her rock-hard penis and the sensation sent her into a pyrexia of pleasure and she ejaculated deep inside Stephanie who was in the throes of her own climax.

The two pretty women ground against each other, their nylons rasping as their thighs scoured together. They slavered at each other, their tongues intertwined; Candi squeezed Stephanie's buttocks, cruelly digging her fingernails into the soft globes but this only served to stimulate Stephanie further and she bit Candi's shoulder to smother a scream.

As their passion peaked, Candi emptied the last of her seed inside Stephanie in series of deep hard thrusts while Stephanie chafed her sensitive clitoris and labia against Candi's shaft and groin.

Their desire abating, Stephanie lowered her feet to the floor and stood; they leaned into each other, tenderly kissing and caressing. After a few minutes Candi broke the kiss.

"Wow! I wasn't expecting that," she smiled broadly.

"And neither was I. It just came out of nowhere when I started to adjust your lingerie and you started to become aroused and then I couldn't stop myself," Stephanie smiled back sheepishly.

"Although...I don't think you were complaining," she grinned at Candi.

"Oh god no! It was wonderful. And so kinky being in the middle of the store. Do you think anyone heard us?" Candi looked a little concerned.

"Babe. I'll admit to shagging in these VIP fitting rooms one or two times in the past and no one has ever said anything. But I better get out there and bring you some clothes to try on to justify the time we have spent here," Stephanie said.

"And I do need those clothes," Candi laughed.

There was a conveniently placed box of tissues on the small table next to an ashtray and small vase of flowers. The girls disengaged and used handfuls of tissues to clean up, Candi pushing her deflating penis back between her legs and pulling up her pantyhose and panties and Stephanie pulled up her knickers and smoothed out her skirt.

Stephanie made numerous trips to the fitting room bringing in outfits, shoes and accessories for Candi to try. Candi eventually settled on a couple of skirt and blouse combinations and a navy-blue business suit similar to the one Michelle had worn last night. She selected three pairs of high heels, black, red and white and a knee-length camel coat.

Candi left the fitting room wearing a black pencil skirt, cerise satin blouse, the same black panties, bra and the grey pantyhose that Stephanie had helped her change into, and a pair of black patent leather high heels. She was proficient enough to walk around the store without falling but every now and then she would need to check her gait to ensure she was walking like a woman rather than a man.

Candi had Stephanie accompany her and she was nervous but excited to be walking around dressed as a woman. She had come so far in such a short period of time, helped by the fact that she had a trim figure, small stature, androgynous features, killer legs, a falsetto voice and once been an accomplished dancer. She carried it off almost perfectly.

"You look wonderful sweetie. Very convincing," Stephanie whispered in her ear.

After buying more lingerie and a satin negligee they browsed the various displays and Candi purchased a couple of silk scarves, a handbag, two purses, some costume jewellery, two watches and a clothes and hairbrush set. Candi put some plain gold earrings in her ears, a matching necklace around her neck and bangles on her wrist and checked out the results in the mirror at the jewellery counter.

"You accessorise wonderfully," Stephanie whispered in her ear and surreptitiously nipped Candi's earlobe.

"Stop that...I'll miss my hairdresser," Candi playfully slapped Stephanie on the bum.

Stephanie packaged up all of Candi's purchases.

"This is going to come to quite a bomb darling; can you afford all this?" Stephanie looked a little concerned.

"I have a budget babe and so far so good. Can I have it all delivered? I'll pay the delivery fee because I really have to get to my hairdresser," Candi said.

"'I really have to get to my hairdresser,' listen to the pampered doll," Stephanie joked.

"Sure honey, I'll have them delivered at six o'clock ok?" Stephanie patted Candi's hand reassuredly.

"Thanks babe. I think I've got the confidence now to walk over there," Candi replied.

"You'll be fine Candi," Stephanie smiled.

And walk over Candi did, feeling confident and sassy. She quite enjoyed sitting in the hairdresser's chair and being attended to.

"Michelle Murphy made the booking for you hun. You know she used to be Cherri Pops in Transvixen right?" the hairdresser had big blonde hair, over the top makeup, her skirt was so short it barely covered her arse and her heels had to be four or five inches high.

A real caricature of the dumb blonde hairdresser; right down to the chewing gum.

"Yeah I know Cherri Pops intimately," Candi giggled at her own joke.

"Here you go hun. Tada!" Mandy the hairdresser spun Candi around in her swivel chair to face the mirror.

"Whadaya think?" she clacked her gum.

Candi looked good before... but now she looked absolutely gorgeous. Her brunette hair had been cut into a delightful bob with lighter streaks. The fringe rested on her brows and accented her dark eyes.

"Great hey hun?"

Candi nodded and patted at her hair.

"You look dazzling! That figure...those legs...those clothes...and now you got the hair. I know you are 'special' but if Cherri hadn't told me, I would never have guessed," Mandy beamed.

"Thanks babe," Candi was still fussing with her new hair style.

"Cept for those nails babe. What about a manicure? Only two quid and you get false nails, a nice polish, the whole shebang," Mandy's smile broadened when she saw Candi's look of consideration turn to one of assent.

Candi had one more stop. She ducked into a camera shop and paid a small fortune for a Polaroid SX-70 camera with remote shutter release

Candi walked home dressed in her black pencil skirt, cerise satin blouse, grey hosiery, black heels and her camel coat. She strutted down the street, self-assured and confident in her looks. Heads turned when they heard her heels click-clacking on the pavement to ogle her pretty face, trim figure and killer legs. She walked past a construction site and the workmen wolf-whistled and shouted complimentary obscenities.

When she got home she contemplated what a wonderful day she had had. Candi was amazed at how well she had passed as a woman. She had come so far so soon. But it had cost her plenty. She did the mental math and then worked out how much she would need to live on until she finished her stewardess training and started getting a decent wage. She might just have enough now that most of the expensive items had been bought up front.

The job at Bocca di Lupo would have to go; she would need to live full time enfemme to carry this off. She could go back to being Christopher Nyland, evening concierge at the restaurant, for the couple of days that it would take for the airlines to process her initial application but the reality was Candi just loved being Candi.

Besides which the fringe benefits were fantastic; a blowjob from Cherri Pops aka Michelle Murphy and a wonderful fuck from Stephanie Parker.

She impatiently sat waiting for her purchases from Debenhams and when they arrived she 'played dressups' by herself and took numerous pictures of herself with the Polaroid Land camera. She laid out the photographs and selected the best five.

Candi sat at her dresser that night dressed in her negligee, panties and bra. She'd left on her heels as she'd been instructed so she could practice walking in them but she was already a natural. She'd done her voice exercises too and the falsetto was becoming natural to her.

She was tempted to call Michelle Murphy and tell her about her day but she thought, rightly so, that it would be too pushy.

Instead she sat at her writing table sipping red wine and smoking while she wrote a letter of resignation to Bocca di Lupo effective immediately stating family difficulties and the need to travel overseas immediately.

Candi's parents had moved to India a few years ago, there were no siblings and her friends were really just work acquaintances. It was quite easy for Christopher Nyland to disappear and for Candi Pops to appear. She didn't understand why Michelle had said there would be 'difficulties that would seem insurmountable'.

Christopher had remade himself into Candi Pops in just a couple of days, had quickly become convincing with Michelle's help, had been out and about and had never been clocked except for the two women who already knew she was trans.

"You've come a long way baby," Candi sang to herself and drained her wine.

She poured another glass wine and began putting completed applications for airline steward positions, freshly typed CVs, and a single Polaroid picture into each of the envelopes addressed to the big five airlines.

The applications were easy enough to complete; they were mostly 'pick and tick' questions followed by the usual age, weight, height and build and summary of why you wanted to be an airline steward. The direction was to attach a CV stating experience and training that would make you competitive for selection, and to attach a recent full-body photograph.

She had dithered when it came to writing her name on the documents. There was no way any airline was going to take seriously an application from a girl named 'Candi Pops'.

Candace Pops!

That's it! That would be her name.

She posted the envelopes the next day and spent the rest of the week refining her look, practicing walking, posture, gestures and voice. Perfecting her feminine psyche and feminine physique until it all became intrinsic. She ventured out every day so that being out and about enfemme was no longer daunting.

Candi opened her front door five days after posting her applications and found a single letter that had fluttered through her front door mail slot. Her heart started beating faster as she instantly recognised the insignia of Goldwing Airlines.

She nervously tore the letter open before she had even closed the door.

'Ms Candace Pops,


Candi read no further. The whooped and cheered and kicked the door closed behind her and raced into the kitchen with the letter grasped tightly in her fist. She flung open her little refrigerator and took out a bottle of Champagne that she had been keeping for years for just this occasion. She poured a glass and gulped it down and then poured another.

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