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Driving Lady Dorothy

Posted by: Age: 50+ Posted on: 1 comments
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A job interview to be the personal driver for a wealthy, matronly English lady requires some special qualifications to satisfy a demanding, perverted mistress


I had been monitoring the postings for any kind of job that would allow me to stay in the London area for a bit. When I saw the new advert for a personal driver I responded immediately hoping to beat the rush for a rather posh job by London standards. The only odd thing about it was the request for several recent full body photos and a face shot. They also wanted my jacket and pant size for a uniform I imagined. I popped off the package of photos and information to the indicated email address and hoped for the best. When I got the reply only a few hours later requesting me to come in for an interview I couldn't believe my luck. The address where I was to report was in one of the wealthiest areas of Surrey, just outside of London. I put on my best suit, a bit worn but clean, a dark tie, and headed out to the interview. Arriving just before 11:00, I found the servant's entrance and rang the bell of a rather imposing and well maintained Tudor estate. "You must be Thomas. I'm Louise, Lady Dorothy's assistant and dresser. Follow me. I'll need to have you fill out some forms and answer a few questions before I introduce you to Lady Dorothy". Louise appeared to be a bit older than me in her late 20's or early 30's and a stunning beauty with auburn hair pinned up very proper, blue eyes behind tortoise shell glasses, long legs, and a distinct Scottish brogue. She wore a very frilly, high collared white blouse that strained against her voluptuous breasts.  Her lacy bra showed plainly through the sheer material as she turned and led me to a small room off the kitchen. Her tight tartan tweed skirt and wide black leather belt clung to her full hips. The skirt had deep slits on both sides revealing the tan welts of her stockings. Her ankle strap high heels clicked on the wood floor as she led me down the hallway to a small table. While I filled in some obligatory forms, she quizzed me on my qualifications. "Lady Dorothy will need you to be available to drive her about at irregular times. Will that be a problem, Thomas?" "It shouldn't be,” I smiled, knowing I would say anything to land the position. "Do you know the London area well, especially the public parks?” she quizzed. "I did pass ‘The Knowledge’ but I failed one of their other tests," I acknowledged, hoping I could avoid explaining my positive drug test for grass. "You're a very handsome young man, Thomas. I should think her ladyship will be pleased with you if you don't fuck up the rest of the interview," she said rather quietly , crossing her legs just high enough to give the briefest glimpse up her tight skirt. She picked up the phone on the table and spoke to her mistress. "Lady Dorothy will see you now, Thomas. We were just preparing to go out when you arrived but she'd like to see you now if you don't mind." We went upstairs to a large bedroom and Louse motioned me to go in by myself. Sitting at a small dressing table was a mature, full figured woman of perhaps 50 years with silver hair that was neatly styled falling just above her shoulders. She was applying her lipstick but my eyes immediately took in her curvaceous form dressed in a sheer lace trimmed white slip. Underneath I could plainly see her white suspender belt which held her tan seamed stockings taught against her ample thighs. Her faint pubic bush and broad buttocks were framed by the suspender straps. She made no attempt to cover herself and showed no trace of modesty or shame as she nonchalantly introduced herself to me. “Come in young man. I’m Lady Dorothy and I should like to employ you as my driver if you are up to the task. You may stand over by the window.” She turned to me as I stood somewhat self-consciously facing her with my back to the large window that looked out over the rear or the estate. “Do you think you can operate the large motor car that my late husband left me? It’s parked below on the driveway.” I checked out the late model town car through the window and replied I had driven a similar car before which was a total lie. “You seem like a very fine fellow from your email response, Thomas. I must let you know that in addition to driving me to my regular public social functions I will also need you to provide your services for my rather…private proclivities.” I could sense what she was going but at just 24 I had not had sex with a middle-aged woman before so I wasn’t sure how I would like it. She sensed my consternation. “Oh dear boy, don’t worry. I don’t want you to fuck me, at least not directly. I just want you to drive me to the park where I can indulge my rather perverted passion for masturbating while strangers watch me. Have you never encountered a woman ‘dogging’ in the park Thomas?” she said with a slight smile. “I rather enjoy watching strange chaps stand outside the car window and stroke their cocks while I play with my pussy. If they are very good and please me I may even let them cum on my stockinged legs or tits.” “I really could use this job,” I admitted rather candidly, “so I’d do pretty much anything you asked if the pay was ok and I had a place to stay.” “Well, Louise can give you the boring details but I still need to see if you can measure up to the task.” Without a further word she dropped the sheer slip off her shoulders and stood up easing the lacy nylon garment over her waist and legs until it fell around her high heels. Then she reached behind and unclasped her full bra letting her pendulous breasts with their saucer sized areolas drop into view. She casually paraded to the chaise that was about 4 feet from where I stood and sat, opening her stockinged legs wide and giving me perfect view of her gaping well lubricated pussy. Her labia were furled about her swelling clit that peaked out like a pearl from its hood. Her dark, full bush extended almost to her navel and partly down the insides of her ample white thighs. “I should like you to take off all your clothes,” she breathed with her eyes partly shut. “Louise will bring in your uniform in a bit but I should like to see if your cock pleases me first. Now, undress and stroke yourself until you are fully erect.” Not hesitating, I removed my shoes and clothes and left them in a heap beside me. In moments I was standing completely naked before Lady Dorothy’s admiring gaze with my firm butt facing the large window behind me in plain sight to anyone looking up from below. I was in excellent shape and very popular with the lasses once they got to see my fat uncut erection. I stroked my cock slowly letting it rise to the occasion until it was at full attention standing straight out from my balls with my glans protruding out from my fully taught foreskin. Lady Dorothy slipped her hand between her legs and fingered her wet slit beneath the taught garters that stretched against her thighs. The door opened just then and Louise briskly entered, her black stiletto heels clicking on the wood floor. She was carrying a driver’s uniform in her hands. Her eyes instinctively dropped to my throbbing cock and sagging scrotum and a slight smile crossed her parted lips. “I think Thomas will work out just fine, don’t you Louise? He seems to have all the qualifications for the job. There’s just one rule that you must obey however, young man. No matter how I may implore or cajole or beg you to fuck me, you must ignore my pleas and not try to penetrate me, ever. If you give in and put your cock inside me I will have to let you go. Your predecessor failed to follow this simple rule and was let go just yesterday. Do you agree to these terms Thomas?” “Yes, milady,” I replied, as I gazed at her fingers slipping in and out of her glistening slit and stroked my shaft while she watched intently. “Louise, can you assist our new driver a bit dear? I’m sure he won’t mind if you undress and join us.” Louise undid her blouse and removed her bra, then unzipped her tight skirt and dropped it to the floor. Her firm white breasts and erect pink nipples were stunning as was her stockinged legs. Like her mistress she wore only a suspender belt and nylons with no knickers to cover her freshly shaved pussy. “How would you like me to help, milady?” Louise asked Lady Dorothy. In a dusky voice, Lady Dorothy gave her instructions. “I should like you to test his will power without giving him the satisfaction of touching or fucking you just yet. Thomas, please lay on your back so that Louise can bring her cunt just above your face. Louise will rub her pussy to orgasm and, if I know her, give you a big surprise. Louise, please straddle his face and bring your pussy where he can see and smell you but not taste your cum?” “Yes, milady,” Louise said with a smile of perverted delight. As she stroked her clit in circles just above my nose, her glistening wet pussy grew deep pink. Her scent and wanton moaning combined to make me insanely hard as I strained to resist expelling my load before Lady Dorothy had reached her own climax. Louise quickly got highly aroused and very much wanted to end the teasing and get fucked by my hard, hot rod. “Milady, I should very much like to slip Thomas’ lovely cock into my pussy now, if you don’t object. I do want to fuck properly and have him cum inside me,” Louise sighed involuntarily as her juices oozed down from the bottom of her cunt. “It’s been so long since you’ve let me fuck a man properly in your presence.” “You are still the same dirty slut you were when I found you dogging and giving blowjobs to those construction workers in the park, aren’t you Louise?. Why don’t you tell Thomas how you would pee for money in the back alleys of Edinburg when you were growing up? No, you may NOT fuck him now, you slutty whore, not until you spend all over his face so he can taste your cum.” Lady Dorothy was leaning back, her legs up and her right hand vigorously sliding over her clit while probing her pussy with three fingers on her left hand. Her tan stockings were pulled taught on her white thighs and her suspenders pulled up as her white girdle bulged over her belly and ass. Her large rippled breasts heaved and swung back and forth as her orgasm began to build and her breathing grew faster. “Oh yes,” Louise gasped, moving her pussy against my face. “Oh, fuck yes.” Her hand became a blur on her clit as her orgasm swept over her. A gush of wet, sweet pussy cum shot from her hole and anointed my open mouth and face. “Oh you dirty, filthy slut Louise. How dare you cum like a slut whore and squirt your pussy juice on sweet young Thomas like that. I’m going to have you CANED for that, do you understand, you slut. Oh fuck, fuck, fuck!”, she moaned as her long, protracted orgasm convulsed her mature body leaving her thighs quivering and her chest heaving in spent passion. The sight of this matronly woman lost in wanton abandon and shrieking in shameless lust drove me over the edge. My balls pulled up and I shot at least six glorious ropes of my hot jism onto Louise’s parted ass. Lady Dorothy momentarily regained her composure, keeping her thighs open wide and running her fingers through her wet pussy lips and damp bush while speaking. “That will do for now, Thomas. Louise will help you clean up and get settled. When you are dressed and I’ve finished dressing as well you will drive me to the park where my ‘audience’ awaits. I do hope you will work out, my boy. I have many such pleasures in store for you and Louise if you can obey my rules.” “Yes, milady,” I responded, my cum still dripping off of her very satisfied and smiling assistant’s ass.

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