Driving Simon

My name is Rachel Stevens. My job is a little unusual, but I like that; I’m a chauffeuse. I quite enjoy my work and I get to wear this real spiffy little uniform in light grey with a cute little peaked cap – all made to measure. I look damn good and I get paid for it and paid well, too.

I’m employed by this big retail company to drive around one of the directors. I’d better not give any names, so I’ll deliberately change those details. The company is a big high street business and I don’t think they would appreciate themselves or their directors mentioned here. As I’ve said, I really like my job. My name is not really Rachel Stevens, by the way.

I don’t just chauffeur (or should it be chauffeuse?) the one director, of course, but I mainly do. I pick him up in the morning, drive him to work and in the evening take him home again. During the day, I have sundry other duties like ferrying clients to and from meetings and the airport, station or bus stop (ok, I’m fooling: these types don’t use buses). Essentially though, I am Simon’s chauffeuse.

Not that I call him Simon, of course, it’s always ‘Mr Green’, or ‘Sir’. He calls me ‘Stevens’ or ‘Miss Stevens’, except in one particular type of situation, as you shall see. Sometimes, we don’t drive straight home after work. These are the occasions I am writing about. Here, I shall call him Simon.

‘Let’s go cruising, Rachel’, he’ll say and off we will go to the dark streets, where we drive along at a slow speed which makes it clear that we don’t really intend to be getting anywhere soon. This is strange for many people try to get through the seamy seedy underside of the city as quickly as possible.

Kerb crawling its called. The girls here are lined up, waiting. Some look better than others. I don’t like it much, but I’m safe enough. The cops don’t like this sort of thing either, but I guess that’s one of the advantages of having a chauffeuse … so easy to say that we are lost and asking for directions, so believable if it’s a woman driver. Far more believable than the truth, I expect: we’re out trying to find a whore for Simon.

How does a clean-living girl like me get involved in such a business, you are probably wondering. Well, it never originally started like that – Simon used to be a bit more discrete. Originally, it was ‘I need to pick up a friend’, and then as he felt more comfortable with me, or maybe bolder, this just kind of evolved. It’s all a bit difficult to imagine and I certainly find it difficult to describe. There’s something voyeuristic about all this – I’m not directly involved and yet the whole situation involves me. I don’t like to think about it too much; it’s puzzling and I think it tells me something about myself that I don’t want to know.

But it’s not about me. It’s about Simon, sitting in the warm comfort of his nice chauffeuse driven company car, looking for his evening’s entertainment.

He always likes drawing this part out. He’s probably like this in restaurants: taking his time perusing the menu; trying to find just the right dish to satisfy his appetite. We drive along a bit … browse … sometimes we park … look … drive around … come back … park. It’s difficult trying to tell it, but it’s what we do. It’s a waiting, looking, thinking, planning game.

And then we swoop – it’s like a commando raid. He’s spotted one – I don’t know how he’s made his decision, but he’s made it and we’re going in. Slowly I pull the Daimler out, careful to not obstruct traffic … it’s difficult negotiating with a prozzy when there’s some guy behind you tooting his horn. (Tooting his horn … that’s a good one!) Okay, maybe that’s not really swooping, but it has that kind of dramatic feel to it (my imagination kind of livens things up, sometimes).

This all very much follows a pattern. It will help my story if I just take one particular case as an illustration. Simon is not very imaginative and, although there is occasional variety, this recent incident (just last week) is pretty much typical.

This is Jessica. She looks 25, but is probably younger … 20, perhaps, or maybe she’s older; you can’t always tell by the light of the streetlamps. Impressive cleavage, bigger than mine, but I don’t feel jealous: that is not a cleavage that you put in a uniform, unless you’re making a porno, that is. She exudes confidence as she moves. I’d be cold dressed like that. She is wearing a leather jacket over a cheap red dress, which does a lot to show off her figure, but little to keep it warm. She approaches the car like most people approach a cash dispenser; it’s probably much the same to her.

Simon handles the negotiation. He has this down to a fine art: he waves a big wodge of notes. This guy is a financial director and he can’t talk money to a street girl. I guess he likes the idea of being able to buy her; it’s more than she’s worth, but the illusion would be broken if he had to haggle with the merchandise and the illusion is probably everything – I think Simon’s inner world is a little fragile.

The sight of the notes is enough for her and she climbs into the car beside Simon. I can’t see, but I imagine she puts a solicitous hand on his knee. I put the car into gear and we pull away.

‘I’m Jessica’ I hear her say. ‘What’s your name, honey?’

He gives her half the wodge of notes, which disappears from view amazingly quickly (well, no I don’t see, but I bet it does). He doesn’t answer the question.

‘You’re my bitch’, he says (where has he got that from?). ‘You will address me as ‘Sir’! I want you to take off your clothes.’

‘Now. Bitch!’ (He hasn’t given her a chance to comply, yet; but I guess that’s all part of it.)

‘Yes, Sir’ she says and undresses. It doesn’t take long; she’s not wearing much.

‘I don’t take it up the ass, Sir’ she says. (Simon’s not into that sort of stuff anyways)

Simon has already got his cock out and has been stroking it while watching the girl undress. I can’t really see this either in the rear view mirror, but this is what I know is happening. I’m trying to keep an eye on the road, which is more important than my boss masturbating.

‘You want me to suck that for you, sugar?’ she says. There is a pause. ‘Sir’.

I see Simon’s head nod behind me, feel the small movement in the car as the weight of the two bodies behind me shifts. I do find that slightly erotic: I know what is going on; I have the evidence of my senses; I can feel the subtle changes in motion in the car, but I cannot see. I can see all of Simons face in the rear view mirror; see his expression change, as it will and know that the cause is Jessica down below sucking his dick. His eyes meet mine in the mirror and I am drawn into the whole experience in a way I find difficult to understand.

The eroticism is usually spoilt by Simon’s occasional need to give me some form of commentary like: ‘Rachel, she’s taken it all,’ or stupid requests like: ‘Rachel, can you find some speed bumps, please?’ Men!

It’s normally a 25-minute journey. The windows are dark tinted, which is just as well when we are stationary at traffic lights. At some point I usually lose interest in what is happening behind me. I have a job to do. Simon, I know, likes to play and tease, but he’s saving himself for later.

I park the car in the drive. He has a nice big house, but there are no lights on except the PIR, which was triggered when the car drove up the graveled entranceway and approached the building.

Jessica is dressed again. She gets out holding his hand and he follows. He has not bothered to ‘adjust his clothing’ (I love that phrase) and his cock is still jutting out obscenely in front of him. The cool night air does not seem to reduce his excitement and he obviously has no idea how ridiculous he looks. The drive near the house is quite secluded, so no one is to see what goes on apart from us. I try hard not to giggle.

He opens the front door with his key and we go inside. The lounge is large (of course) with two matching leather sofas on either side of the big brick fireplace.

‘Take a seat’ he says. I sit on one sofa and Jessica sits on the other. I’m quite relaxed, the grey leather is nice and comfortable, just a shade darker than my jacket. Jessica is nervous though. I guess it’s not the securest of professions. I wonder if she feels safer with me there, or whether my presence in my neat little uniform is just a bit too strange for her.

Simon moves to the sofa that Jessica is sitting on (yes, it’s still sticking out, bobbing about in front of Jessica’s face). Jessica, who I think is unsure of exactly what is expected now, starts to suck his cock again, probably just because it’s there in front of her.

Simon is standing sideways to me, I expect deliberately to give me a good view. He talks to me, because that will keep me looking at him and the girl who is trying to swallow his cock. Having me there must be a big turn-on for him. I don’t know what he thinks I make of it all. Perhaps it’s my indifference, maybe it’s the uniform (did I tell you I’ve got this real nifty little uniform?): something clearly works for him.

Jessica is really doing a good job sucking Simon’s stalk (she’s sucking Simon’s stalk – try saying that quickly! Giggles.), somehow she’s managing to involve her whole body in the process. In many ways it seems just a bit too good to be true, but it is beginning to excite me just a little. I try to think of other things. Jessica continues working on Simon’s cock, her body submissive to his will, but her mind, I think, has gone shopping.

Simon, though, does not really care where Jessica’s mind might be right now. Her mouth is doing a most professional job on his executive member; taking it in deep, pulling it out; licking around the swollen purple head with her tongue; she slurps noisily for effect and then it’s back in again.

‘Oh Yes!’ says Simon, momentarily forgetting me, and the remembering me again. He doesn’t really want my attention to wander.

‘Can I get you a drink, Rachel?’ he asks.

‘A tonic water would be nice, thank you.’ I say. There’s no reason not to be comfortable and I think Simon would be disappointed if I refused.

Simon removes his cock from Jessica’s mouth and moves to the drinks cabinet. He drops ice in the glass and pours the drink. Simon knows how I like my tonic. Jessica looks annoyed; I suppose she is offended that pouring me a drink seems more important than her fellatory skills. I can’t help but wonder whether this is some blow to her professional pride (perhaps she takes pride in her professional blow?). The messages Simon is sending in this bizarre little tableau are very confused, but perhaps that’s all part of the game and I’m no psychologist.

Simon’s dick is still stiff and waggling about as he brings the glass to me. It is wet from Jessica’s mouth and maybe some precum; I don’t really want it too close to me. He looks just as ridiculous as before. I thank him nicely and he returns to Jessica on the sofa, his prick as stiff as ever, knowing that I am watching.

‘Time to fuck.’ he says.

I watch as Simon tries to stuff his thick dick into one of his black condoms. He likes the look of black condoms. Jessica positions herself, lying back on the sofa pulling her red skirt up around her waist. Her legs are open: no panties; maybe she never put them back on; maybe she was never wearing them in the first place. She seems to have forgotten about me now the situation is a more familiar one.

‘You want it, slut?’

‘Fuck me, Sir, fuck your filthy slut!’ (I thought she was meant to be his bitch? Oh well, I guess you shouldn’t take all this stuff too literally!)

‘She wants it, Rachel!’ (pathetic!)

He’s between her legs on the sofa, his cock stiffly rigid in its black mac doesn’t really look like part of the rest of him (he could do with a bit more exercise – I giggle quietly to myself; that is probably what he thinks he is getting). He rubs the tip of his cockhead along her slit and she moans theatrically.

‘You want it, bitch?’ (Back on course, Sir.) and before she can answer again he pushes forward, his prick opening her up: she moans a bit louder and wriggles.

‘Oh Sir! Siirrrrr!’ She plays her part. I guess I play mine.

He continues slowly pushing deeper up inside her. He is smiling and his eyes are closed, enjoying the sensation of feeling his cock sliding into her tight slippery heat.

‘Oh Yesss! Fuck Me Sir, Fuck Me!’

Simon grips her hips and starts pounding hard into her. I think he’s forgotten about me right now, caught up in the pleasure of fucking his tart. She seems to be pushing hard back up towards him, meeting his thrusts. There is grunting and moaning with badly vocalized obscenities to lubricate the sexual performance of both participants.

There’s something about being a spectator to this that seems very surreal. I imagine someone else looking at this strange scene: me, all smart and pretty in my little grey uniform and cap, perched on this big leather sofa, sipping my glass of tonic water; while across from me and blatantly in front of my eyes, my boss is energetically screwing a girl he’s just picked up from the streets. I think an observer would wonder what is going on inside my head: I know I would and I know I know; and maybe that’s why I am telling this story.

This does funny things to me, but they are difficult to describe. I put my cap on at a jaunty angle, which I think makes me look a bit more like an air hostess, while across from me two bodies moan and thrust and sweat in sexual heat. This is the gruntfucking stage: Simon grunts and thrusts and Jessica goes ‘Uh … Uh … Uh’, more or less keeping in rhythm. Her legs are up in the air and Simons bare bottom is pumping away obscenely between her thighs. I am unsure how conscious he is of me watching.

‘Uh! … Uh! … Uh!’

Simon has slowed down. I didn’t think he could keep that level of activity up for too long and he is probably close to coming. Jessica is flushed and breathing heavily beneath him. Simon has remembered my presence. He turns to look at me, his body still moving slowly within Jessica.

‘You ok there, Rachel?’, his white buttocks move up and down; he manages a particularly deep thrust as he says my name.

‘Yes, Sir, fine!’ I smile and raise my glass, only quarter full now.

‘Almost done now, Rachel.’ He says, his cock still firm inside Jessica. He wants me to see, needs to know that I see him having sex with this girl that he cares nothing about. Perhaps he fantasizes about me being his mother watching him being a naughty little boy. He’s courting my disapproval. But perhaps I am the fantasy; perhaps he enjoys imagining what is going on inside my head.

He pulls out, still stiff, still wearing the condom. I hate this bit. He still has not fully cum. Standing over Jessica he pulls off the thin rubber sheath and, now his cock is free, starts to masturbate quickly, purposefully. Jessica lies there: she thinks he’s going for a face shot, but perhaps she doesn’t care.

Stroking. The full length of his cock. This is a theatrical wank. He looks sideways to make sure I’m watching. I raise my glass.

And then he cums. There’s usually a lot – maybe he saves it up, I don’t know. Thick white ropes of the stuff jerk out of his dick over Jessica. It’s her dress he wants, her little red dress. He doesn’t want his cum anywhere she can easily wipe it off; he wants it to soak into her; wants her to go home tonight with his jism wet against her skin. He’ll be lying in bed tonight thinking about that.

Jessica lies there. ‘Oh No, Sir,’ she says, protesting ‘Oh No,’ but she just lies there; if this is what he wants to do, she will just let him. Her takings for the evening are good; the dress will wash. I don’t like it though; it seems a mean and unnecessary indignity.

More thick white goo spews over the little red dress. I can see the creamy deposits streaking and pooling on the cloth.

When he has finished, lifting the hem of the spoiled garment, he wipes his sticky cock clean. Jessica just looks on impassively; mind still shopping, I guess.

That’s it. Simon has no more interest in Jessica (if he had any real interest, anyway). He counts out a number of notes. I know he’s not really counting; he’s just turning over the bits of paper. He doesn’t care about the money; it’s all the act of purchasing what he wants and proving he can. Jessica counts though as she watches; you can see it in her eyes.

Simon tosses the money onto Jessica, probably trying to hit a wet patch. He doesn’t offer her the chance to get cleaned up; it’s done; it’s over. Jessica produces a tissue and tries to wipe herself.

‘Rachel will take you back. Rachel?’ The concern for Jessica is false; he doesn’t even look at her; it’s all about involving me again.

‘Yes, Sir.’ I get up from the sofa, placing my empty glass on the side table.

Jessica gets up, still wiping. I don’t think she wants to hang around either, now the business has been done. She clutches her jacket, money and cheap little handbag where she keeps her tissues. She’s trying to hold some dignity too, but not too much, she knows that’s not what is expected of her.

‘Thank you, Sir!’ she says. Simon has little interest in her now, but I guess she has little interest in him either.

I open the front door. It’s dark outside, but as Jessica steps out the PIR triggers again illuminating her brightly out on the gravel drive beside the car. She stands there, isolated

Simon has followed me. He stands behind me, inside the house and probably out of sight of Jessica, but she is not looking anyway.

‘What do you think, Rachel, about all this?’ his tone is conspiratorial.

‘I think you’re a whacko, Sir, but it’s none of my business, is it?’

‘You’re a good girl, Rachel.’ he says and I think almost kisses me, but then thinks better of it. I’m not too sure what he means; whether it’s my honesty or discretion he likes, or just my damn contrariness. I’m pleased he didn’t kiss me.

Jessica gets into the back of the car and I drive her back to where we picked her up. Looking at her in the rear view mirror, she looks small, but defiant. Somehow I can see her better now than I could before, even in the house: I reckon she is about 20. She is counting her money. It must be a good take for her. She hates me: I’ve got a nice uniform and an expensive car; she has a cheap red dress with wet patches where Simon’s semen is drying into the fabric. Neither the car or the uniform belong to me, but I look like I belong. When I drop her off, I’ll drive away in the nice uniform and expensive car and she’ll be back on the street again.

I do and she is.

As I drive away, I see her stand by the side of the road waving goodbye, as if to a friend. This puzzles me at first, but then I think I understand: it’s the car she is waving to. She wants to be seen waving goodbye to a friend who owns a car like that. Another illusion.

Simon is alone now in his big empty house.

* * * *

Why do I put up with it? Well, the money is good and I really like the job. Simon is, apart from his sexual tastes, a very considerate person. I know he is using me to fulfill some part of his private needs and, although I am not too sure exactly what that is, I don’t begrudge him that – actually I feel rather sad and sorry for him.

There is something else. While the events I witness while chauffeuring Simon around leave me pretty much indifferent, I do have other sides to my life. My boyfriend and I live together and he really likes the uniform too. I’m the sexiest thing he’s ever seen, he keeps telling me. But he tells me more often after one of Simons evening entertainments. And he doesn’t just tell me; he does something about it. The sex is INCREDIBLE. But I’m not going to tell you about that.