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Stephanie, a transitioning woman, had gone to a bar by the river in Cambridge to meet a man she had been talking to online. Unknowingly she starts talking to a very dominant local man who, after buying her a little too much expensive wine, makes a deal with her to spend the weekend with him for the cost of £5.

Chapter 3

I wake up some little while later. I am on the same sofa, but there is a soft blanket across me; the light is low and the curtains drawn. It’s clearly dark outside. He is sitting watching me sleep.

“Ahh good, you’re awake; it’s time we got ready for dinner don’t you think?”

“Errrrmmmm, yes Sir.”

“Good. Let me show you the bathroom and you can get yourself dressed. Do you need to go back to your place to find some clothes for the evening?”

“Where are we going?”

“Midsummer House. Do you know it?”

“I know of it, but I’ve never been there. Yes, I really should get something else to wear then.” I think to myself that I had always wished to go there but had never been able to afford it.

“Good, then as soon as you are ready we will take the taxi to your flat and then go from there.”

I go to his guest bathroom, sumptuous, with soft towels and any lotion I could wish for. I ease out the plug and clean myself inside as well I can as well. Then I shower, keeping my hair dry; I don’t have time for that now. My clothes are laid out for me, all of them I notice, so after drying myself and using one of the thick body lotions I first slide my plug back in, then clip my suspender belt around my waist, roll up my stockings, clipping them on. I pull on my knickers, then clip my bra on. I slip the enhancers back in, loving the way they push up my cleavage. Seeing the now deepening bite marks on my breasts and neck I decide the best thing is to leave them until I am at my flat where I have concealer and foundation. My transparent blouse does nothing to hide the marks: if anything it exaggerates them. My skirt looks as classy and chic as when I left my flat many hours ago. I use what makeup I have with me, some lipstick, a little powder, eyeshadow and eyeliner, to finish my face, happy that the electrolysis I had means I no longer have to worry about shaving. A quick look in the full-length mirror and I am happy. I look as good as I can when I have obviously been bruised in sex.

Coming downstairs he is waiting at the bottom.

“Good, I’m pleased you are ready. The taxi will be here in a few minutes, just time for a toast? I took the liberty of pouring you a glass of white wine.” He hands me the glass and raising his to mine he says “to a wonderful evening and a new career: I’d like us to toast stephanie, my prostitute.”

Not entirely sure that I should be either drinking again so soon, or that I should be toasting my own descent, I raise my glass anyway. He looks me up and down, clearly happy with what he sees, but adjusts my blouse anyway, opening a further two buttons. He slips his hand inside my blouse and gently cups my breast, then traces his fingertips over the purple marks, smiling.

“Pretty.” he says.

Finishing our wine there is a knock at the door. He leads me out to a big black Mercedes, the driver looking me up and down with very little self-consciousness. He opens the back door for me, Going round to the other side as I slide into the seat, the driver clearly enjoys the sight of my stocking tops.

“Emmanuel Street.” he tells the driver, then he turns to me “I hope you don’t mind, but while you were sleeping I took the liberty of finding out where you live.”

I do mind, but there is nothing I can do to change it now. The taxi speeds through Cambridge, quiet in the mid-evening. The driver adjusts his mirror to watch as he turns my face to his and kisses me deeply, while stroking my breast, simply brushing my blouse aside. His hand drops and runs up my thigh, pushing my skirt up high as he goes. The driver adjusts his mirror again so that he can see my legs clearly. The car pulls over outside my flat, a lovely old building with huge windows above the Bank on the corner. The driver jumps out and opens the door for me: he smiles at me as I slide across the seat, my skirt pulls up to show both stocking tops, my blouse gaping open to show the lace of my bra. He comes round and takes my hand, asks the driver to wait. There is no way the driver is going anywhere.

We go through the main door then climb the stairs to my door. I’m happy to remember that I had cleared up yesterday. He looks around as we go inside. “Nice place.” He makes himself comfortable in the living room. I offer him a glass of wine which he accepts, and he insists I pour a glass for myself. I ask him if there is any particular style he would like me to wear this evening. He tells me to look classy, but to wear something which gives him access to me. I go to my bedroom and pick out a few dresses. I go back to the living room and show them to him.

“Put them on and show me.”

I go to draw the curtains on the large windows but he stops me.

“No, like this. gaziantep escort Here. Now.”

Nervously I drop my skirt and blouse on the floor. I pull the first dress up, a dark blue sheath with a square-cut neck and a pencil skirt, split on my left leg so that when I walk the welt of my stocking is visible.

“Next one.”

I drop that to the floor and pull up a typical Little Black Dress, tight, short, low.

“Mmmmm maybe later, not classy enough for now.”

That one he puts into a bag. Next is a long dark burgundy dress: I know he is going to pick it before I put it on but I know I will attract a lot of looks. It is fairly modest from the front, slim halter neck, but still low enough to show the swell of my breasts, split to the thigh with a fairly tight skirt, but the back hardly exists. It drops in a deep fold of satin to my waist

“Perfect! Now go and dress.”

I go back to my room and slip off the dress. I discard my underwear and pull out a clean silk suspender belt and knickers. I make sure I am well lubed before pushing a similar, but slightly larger plug in my arse: I know this one gives me more of a wiggle. I clip new seamed black stockings to the six clips and pull up my matching black silk knickers. No way I can wear a bra with this. I sit at my vanity and do my makeup: first some concealer and a good foundation which covers the purple marks, then heavier evening make-up, a quick spritz of Dior Addict and I’m ready. I step into my highest black courts: I’m not expecting to walk far. I go back out to my living room and slowly twirl for him.

He lets out a low whistle.

“Mmmmm, much better, you look divine. Just one slight change. I am sure you are plugged? Please lift your skirt out of the way and bend over.”

I look at him, knowing that the windows are huge, that the lights are on and that he knows and means it . Blushing furiously, I comply. Bending me over the arm of the sofa, he pulls out the plug which he comments that he is pleased to see is a little larger. But then inserts a plug which is clearly significantly bigger and fills me completely. “Now, you are ready my dear?”

“Please, as we will spend the night together, would it be possible for you to tell me your name?”

“I don’t think that is really necessary, do you? You can call me Sir. If someone catches you saying that at the restaurant they will simply assume that you are my assistant.”

“Yes Sir.” I say, slightly disappointed, but turned on at the same time. I get a long silk wrap as we head out to the car. As the driver opens the door for me he grins. He looks round from the driver’s seat and asks where we are headed. You tell him the Midsummer House and he pulls away from the kerb as we drive along. Emmanuel street he says to Sir,

“You made the right choice of the dresses, and thanks for the show, all of us on the street really enjoyed it.” My face is deep red with embarrassment, but he ignores it.

“Good, I’m pleased. Did you see that I put a larger butt plug in her too?”

The driver swerves slightly.

“No, errr I guess that’s what you were doing when she was out of sight.”

“Yes, it is rather special too, it vibrates and is controlled by an app on my phone so I don’t even have to be close. By the way, will you be available to pick us up after dinner, at say 12?”

“Yes certainly Sir.”

I am mortified. They are discussing me as if I was not here… and clearly my neighbours, or at least passersby, had seen me virtually naked. I am thankful that I’d still had my bra and knickers on at the time.

We pull up at the restaurant. I had always wanted to come here, but it is way out of my price league. As the car pulls up the doorman comes to my door and after opening it offers me his hand. I catch a glimpse of the driver’s eyes feasting on me as I get out, knowing that he has seen me virtually naked and that he knows exactly where I live. The doorman mistakes my shiver. “It is a little cold this evening isn’t it, Ma’am, especially when one is dressed so. elegantly.”

Sir comes and takes my hand as the doorman hands us to the Maitre’D

“How lovely to see you, we have your favourite table for you; and who is this delectable creature?”

“Thank you, I am sure you will look after us well. This is stephanie. I found her this afternoon by the river bank. Delightful, isn’t she?”

The Maitre’D takes his coat and my wrap, and we are shown across the restaurant; I can feel many eyes following me. My seat is pulled out for me and as I sit I look around. I can tell we are in a slightly quiet and slightly darker area of the restaurant. The sommelier brings Sir the wine list and he chooses two bottles, a Premier Cru Chablis and a bottle of Chateauneuf du Pape explaining to him that I prefer white wine. A glass of each is duly poured and the waiter explains the dishes of the day to us. Sir raises a toast.

“To the start of an evening of adventure.”

I raise my glass to his. When the waiter returns, he orders our food, not asking me what I want, hatay escort but that is OK: he chooses dishes that sound divine and light.

“While we wait for our food I couldn’t help but notice that you have your knickers on; please take them off and hand them to me.”

I start to stand to go to the Ladies.

“No, here.”

“Yes Sir.”

I thank myself that I’d put them on the outside of my suspenders. I raise my bottom slightly from the chair and with my napkin over my lap, work them down using the slit in my dress. They drop down to my shoes and I lift one foot out of them and bend down to pick them from the floor, trying to look as if I am getting something from my purse. As I do, I feel a buzz starting in my arse. With the surprise I drop them on the floor, just as the waiter is coming back over. He bends down and picks them up: smiling he offers them to me, but Sir puts out his hand and says that I won’t be needing them, and that I had been giving them to him. With a slight nod of the head he hands my knickers to Sir and smiles at me. The buzzing in my arse is increasing and I am getting extremely turned on. Sir smiles at me, repeating that we will be having an adventurous evening.

The food arrives and it is as superb as I had expected, although I do not eat much as I am constantly distracted by Sir playing with the app on his phone which has me on the other end. As we finish our main course and it is being cleared away Sir remarks how much he likes my dress, especially that it shows so much of the side of my tits. I look down and realise he is right. And also that he is enjoying looking at the bite mark he has left there that I hadn’t seen and hadn’t covered with makeup. I blush immediately and looking at my left breast I can see he is right. To make matters worse, that is the side which faces the restaurant. I move my arms to cover it. He smiles. When the waiter comes and takes our order for dessert, Sir asks him:

“stephanie and I were just wondering, do you think it bothers others here in the restaurant that she so clearly has my bite mark on her left breast?”

The waiter coughs slightly and looking straight at my tits says

“Not at all sir, it is only to be expected and shows that you are enjoying her in the way most men here would.”

“So you would like to take her to bed too, then?”

“Of course sir, but I am sure I would never be so lucky.”

“Perhaps, perhaps not.” Sir replies to him.

“Let me get you your desserts Sir, Ma’am.”

He nods and goes away, flustered, to fetch our desserts.

For the umpteenth time that evening I can feel that I am blushing profusely. Sir smiles at me, the humming in my arse diminishing. He excuses himself to visit the toilet and he clearly knows others here, as he talks to the customers at two of the other tables on the way. On his way back he talks to another couple; I see them looking over at me and I blush for what seems like the 100th time tonight. I see Sir showing his friend something on his phone and as he does so my arse comes alive again. I can feel my nipples rock hard and see that they are very obvious through the thin material of my dress. Sir continues to show his friend his phone and the toy starts to pulse. He hands the phone to his friend and now I really have a shock: his friend and girlfriend look over at me and I see his friend is controlling the phone and the sensations in my arse. Then he hands it to his girlfriend who winks at me as she starts the toy alternately pulsing then vibrating fast, then slow, then cycling through. Sir smiles at me as I am clearly almost orgasming at the table.

They all smile at me and Sir comes back over just as our desserts arrive.

“Sir, Ma’am, your dessert. You seem a little flushed Ma’am, is everything OK?

“She is fine,” Sir replies “she is just a little turned on, like a bitch on heat… aren’t you stephanie?”

“Yes Sir.” I manage to say, the toy still going through the cycles his friend’s girlfriend had set going.

Sir looks at me, smiling and turns the humming off, and we enjoy the wonderful passionfruit creme brulee dessert, the wonderful creme coating my tongue and sliding into me, the slight tartness of the fruit cutting through the sweetness. As we finish Sir looks over to me and tells me that before we leave I am to go to the bathroom and change into the very short, low cut, tight black minidress that he had slipped into my bag earlier. Looking, I find it is my bodycon dress. He tells me not to change any of my other clothes, but just to touch up my make-up, and on my way back to thank Jennifer for the way she turned me on, indicating his friends. He orders us both a coffee and I head to the bathroom.

Luckily there is no-one else there, and it is large and luxurious enough. Reaching behind my neck I undo the dress and it slides to the floor. I am now just wearing my suspender belt, stockings and heels. I pull the small black dress up and pull the zip up the side. Looking in the mirror I realise that it just covers the welts on my hatay escort stockings when I’m standing and that when I sit my white skin above my stocking tops will be clear to anyone that looks. For a moment I consider taking off the stockings but remember the specific instructions I was given. Looking in the mirror as I redo my makeup, heavier to suit the black dress, I realise that the dress is very short and clearly designed to be worn with bare legs or tights. It is obvious I am not wearing a bra. I look like a slut. I realise that I can’t spend too long here. I fold my dress up as best I can and drape it over my arm.

Leaving the bathroom I feel naked; I feel like everyone is looking at me. In truth, most are. I walk unsteadily towards Sir’s friends table and see that they are, like him, well dressed, elegant, between my age and his. As I approach the table the vibrator which had been still, suddenly starts to pulse again, I am trying to lean down to speak to Jennifer at the time without exposing my stocking tops. Jennifer looks at me quizzically as I hold on to the chair beside her. I feel her hand on my leg, stroking my thigh.

“Thank you, Jennifer.” I manage to mumble.

“What for, dear?” she replies, sliding her hand under the tight hem of my skirt.

“For turning me on.”

“And how did I do that?”

Her hand has now pushed my skirt up so that anyone that cares to look can see my stocking tops and the white skin of my thigh but the humming in my arse means I hardly notice.

“By controlling the vibrator in my arse.” I just say in barely a whisper.

“Perhaps you should sit down?”

Jennifer slides the chair out and I sit in the chair. I realise as I do that my skirt doesn’t cover my legs at all… and she rests her hand on my bare thigh.

“I do like that dress on you. Of course, I could never wear it, it does make you look so… what do you think Michael?” she says turning to her partner.

“I think it makes her look like a tart to be honest: high class, but a tart.”

“I think you’re right. Yes dear, it looks wonderful on you, because after all, you are a tart aren’t you?”

At that moment the humming subsides. I look over and Sir is grinning and the coffee is on our table.

“Thank you for saying so.” I say, not quite realizing what I’ve just thanked them for. “I should get back.”

“Of course, dear. If you are available next weekend I would love to use you; the same rate of course.”

Blushing again as I realise Sir has told them he has bought me as a whore, I walk as carefully as I can back to the table, thankful for the cover that the tablecloth affords as I tuck my chair in.

Sir congratulates me as we drink our coffee and he compliments my look, commenting that I look just right for my new career. I am starting to relax again, despite being told by three people in the best restaurant in the city that I look like a whore. Perhaps it is the bottle of Chablis that I notice I have more or less finished, by the waiter topping it up whenever he came to our table. Sir eventually calls for the bill. The waiter sees my original dress folded on the chair beside me and offers to put it on a hanger and bag. I thank him, but Sir insists that I go with him to collect it. The waiter smiles at Sir, and I follow him back to the staff area. It’s quiet now, I guess it’s late. He takes a hanger and bag from the rack where the uniforms are and asks for the dress. I hand it to him and he slips it over, covering up the precious fabric in a dry-cleaning bag. He goes to hand it back but holds it just out of reach. I go to grab it, but I’m a little unsteady and I fall into him. He holds me up with his left arm around my waist. His right hand is free to explore.

“You’ve been teasing me all night with your showing off, haven’t you? Well now we are out here, there’s no one going to stop me, none of your posh so-called friends.”

His hand roams up, sliding my skirt up until he can cup my arse. He feels the plug that is in it. Just at that point it starts to hum again and I slump slightly into his arms. “Naughty girl, no knickers: I thought you were a slut, even when you were in this posh dress.”

His hand goes between my legs and I open them slightly for him. “What the. f… What are you, no cunt? But no balls either and I can hardly feel a cock. In that case I’ll just have to use your pretty mouth. On your knees, tart.”

The vibrator in my arse combined with the Chablis means that I am easily pliable. I drop to my knees, and with my long red nails open his trousers and pull out his engorged cock. I lean forward and kiss the tip before running my tongue around the head. I can tell he had been erect a long time so I slip the head into my mouth, caressing it between the roof of my mouth and my tongue, I slide my mouth down, squeezing and caressing the shaft until he is fully inside, then I lift my head to kiss and lick the head before again swallowing his shaft, caressing him the whole time. Very quickly I feel him start to tense, then fill my mouth with his seed. I swallow it all down, being careful not to spill anything. He pulls me to my feet and tells me to fix my lipstick. That done and my dress pulled down as much as it would, he slaps my arse and propels me back towards the restaurant. Getting back to the table, Sir is smiling.

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