Driving Miss Debbie

by Caroline Bradley

June 2002

 

Part 2

 

Debbie awoke a few hours later to a crumpled but otherwise unoccupied pillow on the other side of the bed. She smiled to herself and sat up in bed, gasping in fright as her reflection in the mirror showed a badly askew wig, severely smudge makeup and a deep 5 0’clock shadow. Her left breastform had detached itself and had slid down her chest, making her look like Quasimodo!

"My what a sight!! Debbie exclaimed and jumped out of bed. She took off the wig, the other breastform and cleaned her face with a tissue before tidying up the mess in the bedroom and, going downstairs, removed the glasses and empty bottles; the ‘phone rang,

"Hello sleepyhead, it’s Tor! Listen I can’t talk too much, have to go out on patrol in a sec so, thanks for last night –you are one special person, I really loved the time we spent, can I call round this evening, say at about 8?" Tor’s voice gushed over the ‘phone, "Yes, of course, shit what’s the time?"

"Half nine love," "Oh God, I need to be in a meeting at 12, must go, see you".

Debbie ran upstairs and pulled off the creased and stained nightdress, dumping it into the linen basket, turning to look in the mirror she scowled as, looking back was clearly an unshaven man with no body hair, painted toe and fingernails and smudged lipstick. Leaping in the shower it took 10 minutes to shave and get clean and a further 30 minutes to remove the false nails and get the last vestiges of makeup off. David now stared back in the mirror and he started to get dressed, he’d not worn male underwear for years now and, instead, chose a pair of soft pastel blue knickers, pulling on a matching bra he sighed as he left the cups empty and instead pulled on a heavy black chino shirt and grey trousers.

He left the house in a hurry and ran straight into his neighbour, "Hi, Dave, how are you, no trouble I hope?" "Sorry", "The Police, I saw you had a police car outside for a bit and one returned early this morning." "Oh that, no, just something to do with an accident I saw, that’s all." David was anxious to get away from this busybody and get to his meeting, which he made with minutes to spare.

Later that afternoon, tired and hot from an interminably boring meeting, David got home; the message light on the answerphone was blinking.

"Hi, Debbie love, it’s Paul, listen the wife’s away, any chance we can go out tonight for dinner, I know it’s short notice but I’d love to see you – call me on my mobile, byee"

Paul’s voice sent shivers down his spine, as Debbie he and Paul had been seeing each other for 3 years now and had a platonic, but loving relationship. However, it was very rarely that Paul left a message, their meetings were normally set up by texting each other.

Debbie’s encounter with Tor, the policewoman last night, had made her worried that Paul was in some kind of trouble, maybe that’s why he called. What to do, stick with Paul and warn him, or explore the relationship with Tor – it was the first time Debbie had been unfaithful to Paul – and with another woman – how confusing can life get?? David put his work things away and went upstairs to run a bath, it was always better to think whilst relaxing and performing the magical transformation into Debbie.

Relaxing in a hot, scented bath 10 minutes later after having carefully removed the varnish from toenails, the new Gillette Venus razor was gliding over already smooth legs, arms and torso, including the all important heart shape around the groin. Careful scrubbing of finger and toenails followed by judicious use of scissors and nailfile crafted short fingernails and elegantly rounded toenails.

Stepping from the bath, a vigorous towelling and massaging with Chanel No9 body lotion was followed by billows of heady Chanel talc. Standing on the bath mat, the next steps were liberal application of a perfumed deodorant and then careful wiping of the bare chest with a alcohol cleanser, this was allowed to dry as she (he always moved from Dave to Debbie when the first item of female clothing went on) stepped into a pair of sheer black high-leg lacy panties. Adjusting Dave’s manhood into the crease of his butt, Debbie put on a white satin underwired bra and carefully adjusted the position and the straps – checking the position in the mirror she applied a spray of silicone cement onto the underside of each breastform before nestling them carefully in the cups of the bra and allowing the adhesive to come into contact with the bare chest. This was always the most magical of moments as her silhouette changed to female and the reassuring weight of the breasts changed her posture.

Debbie threw on a pink short towelling dressingown and skipped into the bedroom, arranging her makeup and nails, she pushed toe dividers onto her feet and proceeded to carefully paint each toe with first one and then a second layer of a bright red varnish. Whilst this was drying, tweezers came out to remove a few stray eyebrow hairs and then she covered her face in firstly a cleanser then a toner, dabbing the excess off with cotton wool. A matte foundation to match her skin tone, evened out the flaws and helped try to blend in the line where breastform met flesh. Then subtle shades of pink and blue accentuated her eyelids as blue kohl highlighted her lower lid and, finally, blue lash enhancing mascara slid onto her already long lashes.

She carefully outlined her lips in a dark shade of plum before filling in the lips with s lighted shade – two coats, blotting in between to leave a sensual kiss on the tissue. A soft blusher and a final dusting of translucent powder finished the makeup, she turned and smiled at herself in the mirror before brushing out the long, auburn, curly wig and affixed fresh adhesive tape to the front and sides. The hair set off her face beautifully and she brushed and combed until she was happy with the result; a set of diamante drop earrings and a long thick gold chain around her neck and a matching chain around her wrist competed the illusion.

The final steps were ready to be made, she chose a pair of sheer nearly nude hold up stockings, removed her toe dividers and satisfied that the varnish was dry, rolled the stockings up each leg, marveling at the thrill it always gave as the sheer material touched the recently shaved legs. Next came a sheer white camisole, being careful not to smudge it with make-up and she then stepped into a short red tailored skirt, zipping it up and the back before sliding it around and checking the back slit was correctly places.

She sat back down at the dressing table, carefully to slide her hand under her skirt to minimise creasing, and then laid out the mid-length acrylic nails onto a plastic surface she used to protect the table. The smell of the nail glue pervaded the room briefly as each nail was placed carefully and securely, a quick file to shape and then carefully three coats of matching varnish were applied and allowed to set

Moving carefully so as not to smudge the nail varnish, Debbie selected three rings and slid two onto her right hand and one onto the middle finger of her left. She then uncapped the Chanel No9 perfume bottle and liberally spritzed the heady aroma onto her neck, at the base of her throat, and with a smile, up her skirt. Looking into the mirror she rebrushed her hair and reapplied more lipstick.

Satisfied that the nail varnish was dry, she selected a pair of red 4" heeled shoes with ankle straps and placed them on her feet. A red shoulder handbag and a short black leather jacket completed the ensemble –she was ready for anything now!!

So, what to do?? To call Paul and arrange a favourite assignation at a quiet country pub where he would treat her like the lady she felt, or to call her new lover, Tor, - why not both??

"Victoria McCabe please," the desk sergeant asked her name before putting her through, "hi, listen, Paul has asked me out this evening, I thought I should tell you"

"OK, Debbie, listen," Tor was professional and business like, "go ahead and act as normal, I’ll call on you after 10.00 this evening and we can catch up on things,." Tor giggled.

She called Paul, who was in a meeting, so she left a message to call her back. A few household chores later the ‘phone rang; "Hi it’s Paul, what kept you?" "A girl has to earn a living you know," she quipped, "still OK for tonight?" "Sure, but don’t come to the office, how about 7.30 at the normal pub?" "I’ll be there!" He rang off.

About an hour and a half to kill, Debbie grabbed her jacket and handbag, picked up the keys to the Merc and walked out of the house, slap into the neighbour again!

"Er, hi, is Dave there only I, er I?" Debbie interrupted, "no, he’s out" The neighbour looked perplexed and was even more confused when Debbie showed an enticing amount of leg as she swung herself into the low-slung Merc; she smiled and drove off at speed.

15 minutes later found her at the local shopping centre where she quickly stocked up on essentials like food and wine before browsing the jewellery display and a dress shop. In the dress shop the owner recognised hr and smiled, it was a shop Debbie had visited often and, whilst she was sure that the owner suspected Debbie’s secret, the lady was far too professional (and probably far too thankful for the business) to say anything. A blue satin cap-sleeve blouse took her eye and after holding up against her and admiring the way it shone in the mirror, she asked to try it on; " Certainly, madam, those seem to come up a little small, so you might want to take the next size up to try as well2.

Sure enough, the 16 was tight, but teh18 fitted very well and looked good against the red skirt; she took it off, rearranged her white blouse and skirt, being careful to lift the skirt and pull the blouse down to give an elegant crease-free waist. "I’ll take this please, and have you got any stockings?" The shopkeeper showed Debbie an array of exciting nylon and lycra hose and she chose three pairs, paid up and started to leave the shop,

"Excuse me madam, might I have a word?" The shopkeeper smiled, "In private?" Debbie’s heart jumped a little but she demurred and the lady bolted the shop door and turned the sign to Closed.

"Sorry about this, and I am sure that you are in a hurry, but I just had to know," Debbie just waited, "You are a man aren’t you?" Debbie just nodded, "I thought so, you have been here many times and, few years ago, I was convinced you were on of those.." "Transvestites?" Debbie offered, "Yes, don’t worry, I think you look great and I have no problems with it, I just wanted to know, you see, my name is Angela Gilbert, I am Paul’s wife!"

Debbie tried hard not to react but it must have shown, she had been buying clothes from the wife of her boyfriend!!

"It’s alright, I have known for quite some time that Paul was not being entirely honest with me, so I had him watched and, sure enough these photo’s proved it." She handed Debbie some shots of her and Paul holding hands outside the pub she was due to meet him at in 30 minutes time." I always thought he had another woman, imagine my surprise when that other woman turns out to be a man in woman’s clothing, no, don’t say anything, I am sure you are not to blame, and the private detective has been unable to show if you, Er, spend any time alone together outside of public place"

Debbie found her voice, "Mrs. Gilbert," "Angela, please, ""Angela, I do not mean to hurt you, Paul and I have met regularly, yes, and he has been very sweet to me, but you have my word that we have never gone beyond kissing – it is a platonic relationship."

"I find that hard to believe in one sense, yet I have no proof and I do not want to confront him as I love him dearly and, well, good men are hard to find aren’t they?" Debbie just smiled, "I am due to met Paul this evening.." "I see, yes he called me to say he would be late and wouldn’t need dinner, I suspected immediately that’s why, when you came in here I had to talk to you – what’s your name by the way?" "Debbie, Debbie Fraser is what it says on my credit card anyway," Debbie permitted a wan smile, there was an agonising pause, Debbie could see the woman was struggling with a whole host of emotions, "I thought of threatening to expose you, of exposing Paul, of…oh, I don’t know what to do…," she trailed off, wiping a small tear from her left eye.

"Angela, I would be lying if I said that I was not attracted to Paul, yet you’ll just have to take my word for it that I have never had sex with a man and I am not sure that I would."

"But surely you are gay?" "No, few transvestites are gay as far as I know, yes we want to be accepted as women and to be treated as such but not many go all the way; in fact most are in stable married relationships." "Are you married, Debbie?" Angela was being very sweet, Debbie felt terrible that she was involved in this woman’s heartache, "not now, I used to be but my wife couldn’t handle the thought of Debbie." "I see, so where do we go from here, you should get going otherwise you’ll be late for Paul – I know he hates anyone being late!" She smiled, "Can we talk again?" "Yes, of course, tomorrow’s Wednesday and I know you close in the afternoon, shall I come round about 1 o’clock and maybe we can have lunch together?" "I’d like that, and thank you."

Debbie shook hands with Angela and quickly left the shop, in a daze and in a hurry, her heels clicking on the concrete as she trotted to her car, threw the purchase onto the back seat and dropped into the driver’s seat, pulling down the sunshade to open the vanity mirror, she quickly brushed her hair and touched up her lipstick before reversing out of the parking slot and gunning the engine, she joined the homeward bound commuters util she turned off a country lane and pulled up outside the pub. Paul was already there supping a pint of bitter, he smiled when he saw her and stood up to give her a kiss as she reached his table.

"My you look good, you OK?" His eyes narrowed, "yes sure, no problems but I need a drink, G&T please Paul" She used his time at the bar to compose herself, check her face in her mirror compact and apply a little powder on a shiny spot on her nose.

They chatted aimlessly and Debbie relaxed into his attentive company, she declined anything to eat and mumbled something about needing an early night because of work commitments in the morning. Paul went quiet, then he leaned closer to her and whispered, "I think there’s something up at my company and I don’t know what to do, the directors seem closed mouthed about something and I don’t like it!"

Debbie listened as Paul recounted some financial irregularities that had come to light when he was preparing his department’s annual budgets and how, when he had asked his boss, a main board member, everything was hushed up and he was told to forget it. Paul wasn’t happy with this and had been given ushered into a rare interview with the CEO who made it clear that all would be well, and Paul "looked after", if he turned a blind eye to the apparent error.

Debbie’s eyes widened as she realised this may be the issue that the police were interested in.

"Paul, I think you should also know something else to add to your troubles," she recounted her earlier talk with Paul’s wife. He sat silent and stunned as she talked through the whole meeting at Angela’s dress shop, his only comment being an "Oh shit" when she finished.

"What now?" Debbie’s eyes gleamed at Paul, her heart was racing, she felt emotional and close to tears as she realised the implications of the next steps they may take.

"I, I, I don’t know – you say she seemed cool about us, frankly I am amazed that she had the bottle to get a detective, no that’s unfair – you’ve arranged to meet for lunch tomorrow – hell that’s complicated. I’ve been caught, we’ve been caught, yet nothing’s happened," their eyes met briefly, "and my wife knows I am seeing a transvestite!"

Debbie flushed and looked around the darkening pub garden, but all the other tables seemed engrossed in their own conversations. "I think you better go home to her and call me tomorrow so as I know what to expect from her when we meet at lunch."

Paul, pensive, got up and they walked over to their cars. Debbie opened the Merc and Paul graciously opened the driver’s door to allow her to slide in. Before she closed the door, he bent down and kissed her deeply on the lips, her heart fluttered but he slammed the door shut and confused, blinking to keep the tears at bay, Debbie fired up the powerful engine and drove home.

Tor was standing on the doorstep as Debbie parked the car.

"Hi, love, great outfit…..you OK?" Tor’s smile faded as Debbie got out of the car, her expression clearly one of someone in emotional turmoil. They got into the house and Debbie started to sob on Tor’s shoulder, the events of the day tumbling out of her lipstick smudged lips; the meeting in London, Angela’s unhappiness, Paul’s work worries and her own confusion. Tor gently caressed Debbie’s hair and then fixed them both a glass of cool white wine.

"I see, a bit of a mess then?" Debbie smiled wanly, her eyes all puffy, her mascara reduced to dark rings under her red eyes.

"You really like Paul don’t you?" Debbie’s eyes watered as she nodded. "And how does he feel for you my love?"

"Don’t know," she sobbed, "he’ll stay with his wife and I’ll never see him again won’t he?" She blubbered between intakes of breath.

"Oh dear, you have got it bad my girl, come here." Tor patted the seat beside her and Debbie walked unsteadily over and curled up her legs, her upper torso leaning on Tor.

Tor rubbed Debbie’s forehead and ran her fingers around Debbie’s lips, despite her emotional state, Debbie could feel stirrings inside her as this strong woman reassured her. Debbie raised her head and kissed Tor’s full lips, Tor’s hand slid down Debbie’s white blouse, pausing to cup the breastforms before starting to rub her skirt just above her crotch. Without pausing her massage, Tor stood up and laid Debbie down full length on the sofa, Debbie closed her puffy eyes and let the waves of sensation wash over her.

She tensed as Tor’s hand caressed her knee and then started to slide up her stocking clad legs until one hand was massaging her through her skirt and the other was gently rubbing up and down her panties. Debbie’s tensions and worries of the day pent up in her found almost immediate release as she arched her back on the sofa and filled her black satin panties with hot steaming cum.

"My, my, we were needing release weren’t we?" Tor smiled as she looked down on Debbie before kissing her lightly on her cheek.

"Make love to me, take me, I need to feel loved," Debbie sighed,

"Then go and get yourself cleaned up and sort out your makeup, I’ll be upstairs in a few moments."

Debbie struggled to get up, holding her panties to prevent cum running down her legs. She waddled up the stairs and quickly showered and dried herself before selecting a very skimpy g-string and a short black lacy nightie with matching negligee.

 

To be continued…………

 

 

 

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© 2002 by Caroline Bradley. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.