Driving Miss Debbie

by Caroline Bradley
May 2002

 

"Excuse me, madam, may I see your driver’s licence?" The smart policewoman proffered a hand devoid of rings or varnish, "nothing to worry about, this is a routine vehicle and driver check, we’re just doing this as part of an increase in police visibility following a spate of vehicle thefts in the area"

A well manicured hand depressed the driver’s door window button and the driver opened her handbag and removed a single plasticised card with the new driver’s license, complete with photograph. The policewoman’s practiced eye scanned the card and her eyes widened briefly, she shot a glance at the occupant of the smart Mercedes coupe and then handed the card back, "Thank you, madam, you may proceed."

Debbie retrieved the card, smiled a little wanly at the policewoman, and gently drove off as the window closed on the outside world. In her rear view mirror, she could see the policewoman watching the rear of the car and Debbie was sure she took a note of the number plate as the car accelerated into the traffic flow. Her heart pounding, Debbie drove carefully within the speed limit and headed for home.

Back in the house, Debbie kicked off her high cream court shoes and took off the tailored jacket of her cream suit. Stepping lightly in stockinged feet, she went over to the drinks cabinet and poured a stiff glass of Scotch Whisky; glass raised she caught sight of herself in the wall mirror and she toasted her reflection whilst expertly moving a stray strand of hair from her face. Phew, that was a close shave.

The following evening Debbie was again driving through the leafy suburbs of Hampshire when her reverie was shattered by flashing blue lights in her rear view mirror. Automatically, she pulled over and a large police car sped past, siren wailing. Her heart was in her mouth and she vividly remembered the previous evenings encounter with the law. Undeterred, she drove on to a quiet neighbourhood and parked the car, stepped out onto the pavement and, handbag over her shoulder and heels clicking on the concrete, set off purposefully towards a large office building set back from the street.

Two hours later, in the fading light, Debbie returned, the car’s sidelights flashed once as the remote unlocked the doors and, swinging her long legs into the vehicle, the motor burst into life and the car moved off. Once again, the pattern of the previous evening repeated itself as she drove home carefully and relaxed in the comfort of her living room.

Over a week went by before, one evening, returning to her car parked in the Hampshire street, she had just placed her brown leather handbag on the seat beside her and was preparing to drive off when there was a sharp tap on her driver’s side window. Debbie, shocked, looked round to see the policewoman of a week ago, now dressed casually, standing by the car; she depressed the window switch and waited, scared, as the firm visage of the policewoman was lowered to the window.

"Hello, again, Madam. I would like a word with you please, may I sit in your car?" The woman proffered an identity card. Debbie moved her handbag off the passenger seat as the woman sat down.

"I suggest you drive off from here and head for your home, I will explain en route". Heart pounding, Debbie started the engine and, a little jerkily, drove off.

"We’ve been watching your movements this last week and, I have to say, we are a little suspicious of precisely what you are up to. However, to set your mind at rest we have no reason to suspect you of any wrongdoing but we would like to talk to you about helping us in our enquiry’s." The woman smiled, "can I suggest that we drive to your home to discuss this in a bit more detail?"

"My home?" Debbie whispered, "well, we could ask you to come down to the station!" The woman gestured behind her and Debbie saw a police car close behind, "OK, my home it is." The woman pulled out a radio and pressed a button, "OK, guys, all set up. I’ll call when I need you."

The Mercedes drew up to Debbie’s home and the two women walked swiftly up the drive and into the house.

"You go ahead and pour yourself your normal drink, I won’t, I am on duty." Debbie’s shock at the obvious ramifications of what the woman had just said made her gasp.

"Yes, after the supposed random stop last week we have had you under surveillance. We had seen your car in Alton on a number of occasions in the same area as a surveillance operation and we were keen to establish precisely what was going on. Our ruse was simply to establish initial contact with you and to see the pattern of your visits to Noonan Russo, the offices you visit so regularly."

Debbie sat down, the policewoman sat opposite. "May I ask your name? Mine’s Victoria but most people call be Tor."

"Er, Debbie" was the whispered reply. "OK, Debbie, you have nothing to worry about and this is not an official interview, just a chat, are you OK with that." Debbie nodded, a strand of auburn hair swept across her furrowed brow.

"I need to ask you, firstly, I assume that you are also David Berry?" Debbie nodded, "No problem, it is not illegal to dress in women’s clothing and I must say you do look very good." Debbie mouthed a thank you. "We need to know what you get up to in those offices."

Debbie blushed, "Er, well," "Go on," Tor encouraged, "I won’t bite."

Slowly at first but with increasing confidence, Debbie explained. It all began 3 years ago when Debbie began to flirt with a guy called Paul in an Internet Chat room. The flirting and chatting had gone on for about 18 months before they had met, at a party organised by one of Debbie’s friends in the transvestite community. Paul was a straight guy, married with kids, who was fascinated by transvestites and he treated Debbie with great tenderness. Debbie had been cross-dressing for years and, although it had eventually led to the breakdown of the marriage with Sue, Debbie did not consider herself homosexual, yet Paul was very attractive and she adored the attention he gave her. Their meetings were sporadic at first, Paul not wanting to jeopardize his marriage, but in the last few months they had been seeing each other most evenings after work. Debbie would drive to his offices and they would then go out, mostly to a country pub for a drink and a chat. Paul seemed to need to talk to Debbie and she enjoyed the attention, there was nothing remotely sexual in these encounters although Debbie was beginning to nurture ideas of her own in that direction.

"And how do you arrange to meet, does he call you or is it vice-versa?" Tor asked with a smile on her lips, "no, he always leaves a text message on my mobile, he’s paranoid about anyone finding out about me."

"And have you ever been into his office?" "Yes, once or twice, we have met for lunch on a few occasions and we have a ruse whereby I introduce myself to reception as someone from a client company. Why, what is all this about?"

"Debbie, we are concerned about precisely what the company is doing. We have no reason to suspect Paul but we need to gain access to the offices to check files and their security is state-of-the-art." "I see, you want to use me to get in, why me?"

"Frankly, because you seem the only one who comes and goes regularly yet has no real connection with the firm and, I am afraid to say, we do have some photos of you and he together which we could use to turn him to our side if necessary." "Oh God, don’t do that, I couldn’t let Paul be compromised like that it’d kill him and us," Debbie’s eyes glistened in panic, "what do you want me to do?"

"Next time he calls you for a lunch meeting, call me on this number," Tor passed over a smart business card "Victoria McCabe; CI6; "I’ll come with you as a colleague and, once we are in, I will go to the ladies and you and Paul can go out and enjoy yourselves." Tor smiled and briefly touched Debbie’s arm.

"I have never met a transvestite before, I always thought you were perverts and gay prostitutes, I am ashamed of my previous prejudices. Debbie, I’d be happy to go out with you as girlfriends and I’d love to borrow that cream suit of yours, it looks divine." Debbie smiled with some relief and offered Tor a drink, "Oh, why not, I am due off now anyway".

They chatted for a few moments when Debbie said, "Listen what size are you, 14 or 16 I’d say?", "16 top, 14 bottom, why?" "Follow me". Debbie took Tor’s hand and led her upstairs to a large bedroom kitted out as a dressing room, opening one of the wardrobes revealed ranks of smart skirt suits and dresses; "here, try this on", Debbie handed Tor a black beaded dress with a gathered waist. Tor at first demurred but, with a little persuasion, agreed and Debbie left her to it.

Downstairs ten minutes later, Debbie whistled as Tor drifted into the room dressed not in the dress Debbie had proffered, but in a dark red wine coloured skirt with matching long jacket over a black silk bodice, "Tor, you look fabulous!", "And you have some fabulous clothes, I am so jealous." They giggled, "Let’s go out for a meal, if you like," Debbie suggested, "Not in this it’s too dressy," responded Tor.

An hour later two smartly dressed women were seen leaving Debbie’s house and climbing into the Mercedes. They drove to a local Italian restaurant where the waiters almost fell over themselves to serve the two glamorous clients. Back at the house, Tor sighed, "Thanks Debbie, you are such great company, I haven’t laughed so much in years, but I guess I better call the boys and get myself a lift home."

"Oh, do stay a bit longer, I’ll drive you home,"" No you won’t, I live to far away and anyway,, another drink and you’ll be over the limit." Tor smiled, "Tor, you said you weren’t married but avoided any other questions, can I ask you if you have a significant other?"

Tor’s smile faded, "I did have once, but no longer, just me and the job."

"Then stay the night here and I’ll give you a lift in the morning, we can chat, I so rarely get any company, especially female company."

It was 4 in the morning when Debbie and Tor finally stopped chatting and finished the last of a bottle of excellent Chardonnay. They had found out a lot about each other; Debbie from as early as she could remember had played with girly things and dressed in mother’s clothes, her marriage had been fine but her wife couldn’t stand the uncertainty of Debbie and wanted the man she had married. Since the divorce, Debbie had more or less lived as a woman full time, her job as a web site consultant meant mostly working from home and only rarely did she have to revert to being David for interminable boring meetings. – even then it was impossible to resist the urge of wearing lingerie under the staid man’s suit,

Tor had been a tomboy and fiercely sporty and competitive all her life. Her father was a policeman and the career choice had been ingrained from an early age; she joined starlight from school and quickly rose through the ranks, joining the elite CI5 group two years ago. Her personal life was a little more complex; sure she had boyfriends and even an engagement but it all seemed wrong somehow. In the force were a number of openly lesbian officers and yes, Tor had been propositioned, but she resisted. More recently she had been living with another girl to help with rent and this relationship, whilst non-sexual, had been quite fulfilling for Tor. Her girlfriend had left 6 months ago after a blazing row when she had accused Tor of lying after Tor had been out on a 48 hour surveillance operation.

"Listen, I’ve made up the spare room bed and left on my nighties there for you, sleep well." Debbie smiled as they parted at the top of the stairs. "Thanks", Tor‘s hand brushed Debbie’s arm briefly.

Debbie went to her room and took off her clothes, she had begun to despise her naked reflection – the face of a smart, well coiffured woman and the body of a thin man with no body hair. Ah well, slipping into a pair of comfortable panties, she shimmied into a long peach satin nightgown and sat at the dressing table, carefully removing her makeup. A quick wash and pee and she slid into bed, it was late and she must get some work done in the morning.

Moments later, Debbie wok with a start as she felt someone get into the big king-sized bed with her – it was Tor. "You OK with this?" Tor whispered, "depends on what this is", Debbie smiled. Tor’s hand slowly slid along Debbie’s satin clad body, pausing at where her breasts should be. "Sorry, nothing there," said Debbie, "Never mind, maybe we should swap." With that Tor’s hand took Debbie’s and planted it on an ample breast, nipple already erect.

The kissed, slowly at first but with rising passion, in the dark of the bedroom each was lost in their own fantasies. Tor took the lead and slid under the covers, Debbie could feel her hands and her hot breath as they explored her body. They threw the duvet off and Tor whispered, "Let me do this, I promise you will like it".

Slowly running her hands down the outside of Debbie’s thighs, Tor then ran her fingers up the inside, raising the hem of the nightie as her fingers neared her panties. She repeated this three or four times, Debbie was losing count as the waves of warmth and pleasure wafted over her. Tor’s hand then slid inside Debbie’s panties and caressed the smooth skin, Debbie’s penis was raging hard, trapped between her thighs. Tor started to massage an area just above the base of Debbie’s penis, a gentle circular motion, pushing deep into the muscle. " Now, Debbie, pretend that you are trying to pee, just push down as I rub, that’s it, push, rub, push, rub", Debbie tried and could feel the mounting pressure in her hardness

Tor continued to rub as she leaned over Debbie and kissed her full on the mouth, with wet lips, she bent down and started to lick the hem of Debbie’s panties, taking the mound in her mouth. Debbie moaned with pleasure, this was incredible, this was truly lesbian sex with another woman.

Tor changed position and straddled Debbie, she could sense the nearness of Tor’s panty clad behind and reached up, feeling the tight satin material just above her face. Debbie used her long fingernails to insinuate a finger between the panty and Tor’s leg, the finger almost immediately sliding into Tor’s wetness; Tor let out a low moan and lowered her behind. Debbie took the hint and pulled the tight material to one side, lifting her head up to the proffered body, Debbie smelt and tasted Tor’s warmth as her tongue slid into Tor’s warm embrace. "Oh, yes, Debbie," Tor moaned softly.

Tor’s circling massage of Debbie’s pubic region stopped as she slid down onto Debbie’s prone body, Debbie adjusted her head and soon had all of Tor’s warm pussy in her mouth, Debbie felt Tor try to force open her legs and Debbie readily obliged. She felt her hands reach into the tight confines of her panties and pull out her raging hard penis. Debbie gurgled win ecstasy as Tor’s warm lips firstly kissed the end of her penis and then opened to take the length of her shaft deep into her mouth.

They lay like that for a few minutes, each concentrating on sucking and massaging the other’s pleasure zones, suddenly Debbie felt Tor tense and, with a quiet whimper, a warm flow of juices spread across Debbie’s face. Tor relaxed slightly, then resumed sucking Debbie’s penis, using her hands now to massage the base and the shaft. Moments later it was all over, Debbie tensed, screamed and shot a bolt of cum deep into Tor’s hot mouth

 

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.