A week after the clinic encounter, I emailed Jane to see if she did want to meet again. Her reply was very quick and indicated she did but wanted to know what I wanted from any such meeting.

As I am so submissive I simply wrote that all I wanted to do is to please her and that I find it difficult to express what I like.

She came back with pleasure at my answer and now wanted me to send her a history of my sexual experiences and things that have shaped my desires. This email was signed, "Mistress Jane."

This took a while for me to compile, but I was completely honest with her, about my time in the navy training camp, and travels around the world my first gay seduction by an elderly gent, experimenting with cross-dressing, my walking naked in the fields and so on. I tried to leave nothing out.

She asked for more details on a couple of my experiences, especially those that occurred when I was in the navy and my cross-dressing experience. I obliged her with a full description and what about them excited me most.

These email exchanges went on for several days until finally, she said I was to give her dates when I would be available to visit her for a full day.

With a date agreed I received my final instructions and her address. I was to bring a razor, a shaving stick and a shaving brush. I should be prepared to stay all day and into the evening if required and I should not wear any deodorant or aftershave.

The day arrived and I set off with some trepidation, trying to anticipate what was to come.

It was a huge, double-fronted house that was set back off the road with an in-and-out driveway. I guess her late husband had a successful career in the city or something.

What version of Jane was I going to be greeted by I wondered. Would it be Matronly Jane or Mistress Jane, I was shaking with anticipation as I rang the doorbell.

My thoughts were answered immediately, "You are two minutes late!" she blasted at me as the door opened.

"So sorry, Mistress Jane."

"Come. Up the stairs, second door on the left, go in and wait. Did you bring what I told you to?"

"Yes Mistress," and went to give her the package.

"Take it up with you, go on then, up you go, stand and wait for me."

Up the stairs, I go and into the designated room. It was nearly as large as my flat, I thought, well nearly anyway. It had an en-suite bathroom, a large double bed, a sideboard with a covering over the top and two huge, curtainless picture windows that looked out to the rear.

In front of one window was a massage table, and a small table next to it was set up with prettily styled towels like they do in hotel bathrooms.

I waited and I waited. I could hear her busying herself downstairs and being bored I started walking around the room and looking.

"I told you to stand and wait," she shouted, "not to go nosing around."

I looked around for a camera as the floor hadn't made a noise, how else did she know? I couldn't see one, but it had to be there.

Then I heard her coming and stood to attention as she entered the room.

"It hasn't been a very good start today, has it now?"

"No, I am so sorry, Mistress, I will try to do better." I grovelled.

"Of that, I am certain. where is the razor? she demanded.

I picked up the package and handed it to her.

"Strip," she said.

I immediately undressed and stood naked waiting for her, realising that I was in front of the open window.

"Give me a twirl so I can see you properly. For once, you don't have an erection, that is good, as I certainly don't want it sticking up all day, and for what I have planned it will get in the way."

"Before we start let us both be clear about the rules for today. As we discussed in our email exchanges, I will not permanently mark you, use animals or overstretch your arse."

"If anything gets too much you simply have to say, 'Stop now'. We are both here to enjoy ourselves so we do not want anything to spoil that, so at any point, if you are not certain you want to continue we will stop."

"Is that clear and are you happy with that?"

"Yes, perfectly clear, Mistress, that is perfect."

"Good. I see that you have lost some weight since the clinic."

"Yes, Mistress, I have been following the diet the doctor gave me and I also go to the gym she recommended every day, and swim as well."

"That's good, and do you follow her suggestion about parading your pathetic cock in the changing room? I typed up her notes so I know exactly what she advised."

The doctor, in her letter to me, had suggested that instead of being embarrassed about my size, I should not try and hide it as I currently do in those situations. She suggested walking through the changing room naked, ignoring comments or thinking of them as humiliating, and using them in my fantasies.

It seemed good simple advice until it came to putting it into practice.

"I'm afraid I haven't," I replied.

"Ignoring the doctors' advice is bad, so I will make it an order. You are to use the locker furthest away from the showers and walk naked to them, take your towel but drape it around your neck. We all go to the same gym so I know your showers are communal ones, so make sure to shower with your back to the wall as well."

She continued, "Walk naked and wet back to your locker and strike up a conversation with another member, without trying to cover yourself."

"We know many of the members there so it is easy for us to make enquiries, we even have a couple of participants who go there, and they will keep an eye on you too."

"Now you know what to do, are you going to follow orders?"

"Yes, mistress, I will."

"I am now going to remove all of your bodily hair, hence the reason for the razor. Lie face down on the table."

Without further delay, I felt the lathered brush on my back, followed by the smooth strokes of the razor. Then the same on my bum cheeks and the back of my legs. Then she returned to my bum and lathered up in the crack and carefully shaved inside it as she pulled one cheek over at a time.

A warm flannel rinsed my back, bum and legs, and then a towel was padded over the same area. Then she felt all over it to ensure the job was complete, running a finger the whole length of my arse crack.

"Turn over."

By now I had a small lob on but she did not seem to notice. She lathered up my face, despite me having shaved before I left home.

"I need you extremely smooth for our first bit of fun, well fun for me that is," she sneered.

Face shaving completed, she moved to my underarms which too were soon free of hair, My chest followed, and then she removed all the hair from my stomach down to my cock. Then shaved down each leg ensuring both were perfectly smooth.

She then came back up to my groin and pushed my legs open.

"Hold that pathetic cock out of the way," she demanded.

I did as ordered and she shaved every hair off of my balls, she then wanted me to raise both legs and draw them back to open up my crutch for shaving. This position proved impossible to hold without fidgeting.

"Bugger," she moaned, "Get on all fours, now forehead down on the table, there that's it, arse in the air. Good now spread your arse and stay bloody still."

She now had good access and she quickly shaved all around my hole, and any remaining hairs from my crutch, checking and re-checking that all signs of hair had gone.

She threw the wet flannel at me and told me to rinse myself and then dry off.

"Stand here and let me check you over," she said, "stand in the light by the window, so I can see properly."

This was done to expose me to anyone who might be out there, she took her time to check for hairs, finding some now and then and dry razoring them off.

She went and sat on a low stool and said, "Stand facing me here."

I did so and she said, "Pull the foreskin back."

I di and exposed the head, she looped a noose of thin string under the head and told me to release my grip.

She allowed the string to dangle and then instructed me to turn around. She reached between my legs and took hold of the string and I could sense her tying it to something.

"Bend over and reach behind and spread your arse," she ordered.

Without question I obeyed and suddenly felt cold gel being inserted into me by her finger. Then my cock was pulled down and back by the string and held there. Next, I felt my arse stretching as something was inserted and then it eased.

Once it was in, I could feel it being turned and as it was my cock pulled tighter against my crutch.

"Stand up straight and turn around to face me."

As I straightened I but the pull on my cock was too much and bent again.

“Bugger," She moaned again, "turn around again.”

I felt her turn the object the opposite way and then told me to turn and stand straight again.

Now I could stand with no pain.

"Perfect, now walk to the door and back again."

I did so, realising that my cock had been tied to a butt plug in my arse.

"Look in that mirror, bitch, and tell me what you see."

I looked and indeed it almost looked as if I had a fanny rather than a cock as the combined string and stretched cock split my shaved balls to look similar to a pronounced vulva.

"It looks like I have a vagina, Mistress, just like a woman."

"That you do, and even more so soon."

"Go into the other room to the right and wait for me."

I did so and was a little perturbed by the sight of a lady's outfit lying on the bed, complete with an auburn wig.

"Before we get you dressed I want some pictures of my bitch naked. I want some ladylike poses from you, I promised some to Emily and Emma, so make sure you do your best. In fact, I had better put your make-up on first and add the wig."

She made me sit in front of the mirror which was not too comfortable due to the butt plug. Then she started to make me up, with lipstick, rouge and eye make-up and then finally the wig.

I was amazed at how I looked and could pass as a woman when briefly looked at.

"Use this to pose with," she said handing me a rubbery cock.

Now came the photos, I was posed in all sorts of positions with the cock in hand. I sucked it, licked it and had it between my legs.

Most of the photos were taken with me in view of the window, so I began to wonder if she knew she had a nosey neighbour or something. To me, this was confirmed when once the pictures were done she had me stand looking out the window while she loaded the pictures onto her laptop.

"I've downloaded now and sent some over to the girls. Now let me get my fat bitch dressed."

The wig came off first and then she put a bra on me. It was padded, and she positioned it to her satisfaction. Then came a suspender belt, how do women wear these things I wondered, and over that a matching pair of panties to the bra.

"Put these stockings on, put your foot in and then roll them up, that's the way, make sure you don't ladder them. You seem to know what you are doing, do this all the time, perv?"

"No mistress, only once before as I explained," I whimpered.

"Wig back on, now some more sexy pictures.

I held the cock to my mouth, licked it, and put it between my legs and between the cups of the bra while trying to give a sexy look.

" I suppose that will do, difficult for someone like you to look sexy, back in front of the window while I sort these photos."

Back I went on display until she finished on the laptop.

"Rest of clothes now."

"Slip first, step into it, should all fit nicely as Emma took all your measurements. Now this top and finally the skirt. Yes, that all looks pretty good. These shoes are sensible ones so they will not be difficult to walk in."

When I looked in the mirror I could see what might pass as a middle-aged, chubby female starting to have a little grey in her hair.

"Follow me downstairs, we are going to the local supermarket to do a bit of shopping," she said matter-of-factly.

"What, I've got to go outside like this?" I almost cried.

"No, you don't have to, you can go back upstairs dress in your clothes and go home if you want."

"I mean. well, I just don't know," I blurted out.

"You are the one who contacted me and I want to take you to your limits, but like I said, it's entirely up to you."

To be honest I could feel my cock twitching at its restraint and I was intrigued by the thought of going out although scared as well.

"You are right of course, Mistress, I will come with you."

We added light jackets to our attire, picked up a shopping bag and walked out of the door.

As we walked she was saying, "Your name is Susan, you were my late husband's secretary, who has come for a short visit. Try not to talk too much although your voice is quite feminine anyway."

"Yes, mistress," I replied, practising a higher tone in my voice.

It was quite exciting walking in public, we passed people who she knew and nodded and bid them hello, with no sign of them realising I was a man. I was more worried when we neared the supermarket as the foot traffic increased,

I must be enjoying it as the pressure on my cock was increasing as it hardened and pulled against the string, and I think she sensed it as I tried to ease the pressure by walking with my legs wider.

"Walk properly bitch," she snapped quietly, "you are getting hard aren’t you? What a pervert you are. Just put up with it."

I started to walk as normally as I could and we went into the shop. She was obviously well known in the area as it seemed every other person knew her and greeted us.

"Hello Jane, how are you?" from a voice behind us.

We turned to see a lady similar in appearance to Jane, they hugged and kissed each other on both cheeks.

"I'm wonderful, Sheila, this is Susan, she was Dan's secretary."

"Hello Susan, I love your outfit by the way. Do you know I always imagined his secretary would be a long-legged blond rather than someone like you? I am so sorry, that sounded so rude."

"That is quite all right," I replied in the best voice I could muster.

They chatted for a while and I was forever looking for someone who might recognise me. Unlikely as I was miles away from my town but you never know.

"We must get on, Sheila, we have so much planned for today," Jane said with a big smile.

"Of course, enjoy yourselves, don't do anything I wouldn't do," If only she knew she might not have said that.

"Right, let us get on, just a couple of bits to pick up, then we can carry on."

Shopping was done, she handed me a twenty-pound note and told me to go through the checkout. The young girl on the till kept glancing at me and smiling but I don't think she realised or even cared.

We walked back the same way, and now I was more comfortable in my new identity, actively saying hello to people as they passed us.

Getting back indoors, she told me to make her some tea while she checked her messages. I made the tea and fetched it in on a tray.

"You may join me for a cup of tea then we have to go back upstairs."

I poured the tea out for us both and sat opposite her, albeit uncomfortably due to the plug in my bum hole.

"How did you enjoy our little outing, Susan?"

"Thoroughly Mistress Jane, it was very enjoyable."

"Then we may have to make the next time even more daring, perhaps a more daring skirt, don't want you enjoying yourself too much."

Tea finished, I followed her upstairs and was ordered to stand by the window again looking out.

I heard her typing on her laptop and then suddenly heard, "Hi Jane, are you having a good time? It was Emma on a video call.

"We've just got from an outing at the supermarket," she replied, and then continued, "Is Emily joining you?"

"You took him out, you are so wicked, Jane. Yes, Emily is just finishing with the last morning patient and she will be out."

"What did you think of the pictures, Emma?" asked Jane.

"Oh they were such a laugh, as you know I'm sitting in for you today, so I printed some off, put them in a folder and took them into Emily. She was with this posh old lady, and I said 'Here are some more details for you, doctor.' I thought she was going to fall off her chair when she opened the folder."

"Here she is now, so we are ready at this end."

"Hello Jane, you seem to be extremely wicked today judging by those pictures."

"I am trying to be, Susan, get over here and say good morning to the ladies."

I obliged with a feminine "Good morning."

"He looks really good, Jane, you have done an excellent job, considering what you have to work with."

"Yes not the best of bodies to dress, but he makes a good chubby old girl I suppose."

"Give us a twirl, Susan," said Emma through her giggling, "make it look good as we are recording this."

I lifted my skirt a little and did the best pirouette I could manage. I probably looked more like Disney's dancing hippo in a tutu that anything else.

Hands clapped on the screen as I went around again and again.

"Now we want a strip show, and don't forget to use the props that I know Jane has ready for you."

Music came on through a speaker and Jane removed the covering from the sideboard. On it were a selection of artificial cocks, a riding crop, some baby oil and a long rubber snake.

Jane ordered, " Come on then, you must have seen strippers, so get to it."

I walked to the selection of toys for one to start with, I chose the crop.

I strutted to the centre of the room with it at my shoulder, whacking down on my hip now and then. Then I pranced across the room geeing myself up with it on my backside.

I wiped my brow as if I were hot.

"Take off the top!" one of them shouted.

I gradually undid the blouse, one button at a time, cocking my head and licking my lips in what I thought might be a seductive way.

"Wheeeeee," Emma screamed.

I slid the blouse off one shoulder and then the other and allowed it to fall past my padded bra, as it did I turned my back on them and then turned again with my arms across my breasts.

Whistles came from the audience, then a call to take more off.

The skirt was next, I undid the waist and allowed it to slip to my hips. Then let it drop to the floor and turn my back to them again and bent over to take the skirt from under my feet.

I threw it to the side and picked up a rubber cock from the side. I held it to my cheek and made it bounce off of it.

This bought more shrieks from them and a clap of the hands and a cry of, "She's good."

I put a chair in the centre of the room, placed the cock on it, stepped away and as slowly as I could I took off the slip.

Wolf whistles now came from them.

I sat on the chair with the rubber cock sticking out from between my legs and slowly started to wank it. Then brought it up to my mouth and started to suck on it.

"He wishes he had one like that," one of them said and laughter followed.

I played like that for a while and then started to rub it against my imaginary clitoris, making the appropriate noise as I did.

Now I took off the bra and reaching for the baby oil I rubbed it over my tits, playing with each nipple for a while to the delight of my audience.

"Get them knickers off you bitch," came from the screen.

Turning away again I slowly lowered them over the suspenders and stockings, bending over, but keeping my legs tight together. I retrieved the snake from the side and put it between my legs and turned back to face them.

The snake covered my groin and tits, and I pulled it backwards and forward not revealing anything, and then I pulled it out and threw it to stand there in naked glory.

They clapped and whooped with delight at my effort.

I heard the doctor say, "Jane, have you shaved him?"

"Yes," she replied, "every single hair on his body has gone."

"He does look feminised, how are you managing to keep his penis in that position?"

"I'll show you. Come here, Susan."

I stood closer to the camera so they had a better view.

"I tied some string around his cock head and then--" To me, she said, "Turn around, bend over and spread your arse."

"You see the string come under here and I attached it to this butt plug. It works well doesn't it?"

"Certainly does, but where on earth does a sweet lady like you get the idea for that?"

"In one of my books on BDSM, one mistress shows the same method but hers was done with a catheter with the tube going into the butt plug, so her subject urinated into his arse. I didn't know how to insert a catheter so did it that way."

"I can show you how if you like," said Emily.

"Wonderful, that will make it much more interesting next time."

"Tell him to go out of the room so we can chat," said the doctor.

She did and I left them to their chat, of course, she told me to stand by the window again.

I was called back about ten minutes later and was told to remove the stockings and suspender belt. After I did I felt even more exposed and by now I needed to pee.

"Excuse me Mistress Jane, but I need to go to the toilet," I said to her meekly.

"You pick your bloody moments don't you, you are a nuisance."

"I am not releasing your cock, so stand in the bath and do it there, then use the bidet to wash yourself."

"Yes mistress, thank you very much."

"Jane, take the camera in there so we can watch, go on be a sport," that was Emma again.

So in I go with Jane following, laptop balanced in one hand and webcam in the other.

"Stand in there and let a little out so I can see where it will go."

I followed her instruction and let a small stream out and it went behind me.

"Stop, now face me, legs apart so I can get a view, Yes just like that, you may now go."

With relief, I opened up my bladder and a long stream of pee flowed against the side of the bath and down to the drain. It felt wonderful and I could hear the giggling on the laptop speaker.

"Good girl, now rinse the bath with the hand shower to get rid of your disgusting waste."

"Now onto the bidet and wash your arse and cock well, yes that's it, sit astride the bowl, turn on the taps and give it a good soaping."

"Rinse and dry now, all done, good, so hopefully if it's alright with you, we can get on."

"We enjoyed that little episode but we do think a small punishment is in order for making us wait, what does her mistress think?"

"You know, I think you are right it was unreasonable to make us wait. Now, what could the punishment be?"

"I know, I know!" offered Emma, who else would it be?

"I think she needs a good spanking, what do you two think?"

"Sounds appropriate," added the doctor.

"Yes I agree," said Jane, "Susan, go downstairs and fetch a kitchen stool."

Down I went with shaking legs, I haven't been spanked since I was a child at school. I was completely oblivious to passing the big picture window in the hallway so lord knows what view I presented to anyone bothering to look.

I picked up the stool and returned to the room.

"Put it by the window and then bend over it."

"I am going to use the crop on you as you annoyed us, there will be some streaks on your arse but they will go in a day or so."

She did nothing for a while, I think she was giving me the chance for me to say 'Stop', but I didn't, instead I simply said, "It's what I deserve mistress."

She had the camera set up for the perfect view and I was positioned for offering a good view from the window.

Whack! the first one came down on my backside. It stung like crazy and my arse jumped up off the stool. Whoosh, the whack as another came down again with the same reaction. Another four followed in quick succession and it was over.

"Stand up and face me, naughty girl."

I did and by now I had tears running down through the makeup she had put on.

"Oh look girls, our little girl is crying like a baby. Did your mistress hurt your big fat botty then?"

"Sorry I am crying mistress, I should have taken the punishment better."

"Pathetic," said the voice from the laptop, "a few strokes and acting like that, should have gone to my old boarding school if you think that was bad." It was the doctor speaking.

"Now go back into the other room and you will see another outfit on the bed. Put it on and walk in here in a manner appropriate to the outfit."

When I went into the room I could see a tiny bikini on the bed. The top was modified with some padding to give me boobs, the bottom was little more than a small triangle and string. I also saw another outfit that was still covered but I didn't dare to take a peek.

I heard, "Look under the bed," shouted at me from the other room.

I did and saw a pair of black high heels, mercifully not stilettos but rather cloggy four-inch heels.

Of course, they fitted me perfectly, how did they manage that, so on they went and I practised walking in them, feeling completely ridiculous in this outfit.

I walked into the room again as I imagined a model would walk on the catwalk at a fashion show. When I got near the camera I stopped, smiled, blew a kiss at an imaginary audience, swung around on heels and strutted away.

"What a teaser she is turning into, looks like you have a winner there Jane," said Emily.

"Now can we have some sexy poses from her please," said Emma.

"You heard her, let’s feel the sex coming from you."

I didn't have a clue what to do really, so I started by turning my back on the camera, bending right over and running a finger along my arse crack, round to my supposed fanny. Then I turned and sucked provocatively on that finger, pulled it out slightly and licked along its length.

Then I sat astride the chair pretending to finger my fanny and occasionally sucking on the finger.

They seemed to enjoy it, and I did too as my cock was now really staring against its restraint.

"Come here, bitch, and let me feel you," demanded Jane.

Her hand went between my legs and moved along my cock.

"The bitch is hard as nails girls, should we release it?"

"Oh yes," said Emma, "but keep the bikini on him."

Jane roughly turned me around and pulled the bikini bottom string to one side.

"Spread," she ordered.

I pulled my cheeks apart and she immediately pulled out the plug with a loud pop. It dropped to the floor pulling my cock down and out of the bottoms.

She turned me to face her and roughly grabbed my cock.

Undoing the string she muttered, "Dirty little bitch deserves a good whacking again."

She released my cock and it sprang up.

"Put it away, you perv," she almost shouted.

I did, but that just managed fits of laughter from Emily and Emma as the little triangle of cloth was just being pushed out.

"Photo, Jane, get a photo quick." Emma again.

Jane got her photo to their delight.

"What shall we do now he has his little willy back then girls?"

"Go to the other room again, strip off and stand by the window, if you feel your cock going down, play with yourself. Go on, off you go."

So there I was again at the window, looking out with an erection sticking out. I felt the need to keep rubbing as I was wary of the consequences if it went down.

"We have been discussing events," I jumped as she was suddenly behind me, "the girls were wondering why I have you standing here every time, The answer is, if you look at those houses over there, in the middle one there is a dirty old man whom I have seen several times watching me up here."

"I never draw the curtains because I don't like them closed and I saw him by accident one day with his binoculars looking over here. So I started to secretly check to see if he did it all the time and apparently he does."

"So today I thought I would give him a show, after all, he can't say anything without admitting he is a peeping tom, can he? Now he will see a bit more."

She told me to get the stool again and I feared another thrashing.

"Bend over the stool and spread your cheeks, my little perv."

As I assumed the position, I heard, "Yes, that one Jane."

I felt the lube hit my arse and then it being worked inside with one, then two and finally three fingers, working in and out. Then something hard was there and started to go in, and then it started to vibrate, slowly at first. As it vibrated she worked it in and nearly out. Every time it went back in it was going deeper.

I started to gyrate my arse, seeking more of it. I let go of my cheeks and received a very hard slap on my arse.

"Spread them again, I want him to be able to see this going in and out, don't you dare spoil it for me."

I spread as wide as I could and the pumping continued, the vibrations went up, and my arse was bouncing up and down now.

"Don't fucking cum you bitch," she said in a wicked voice, "or you will regret it."

She must have sensed the precise moment as she removed the vibrator seconds before I would have cum. To be doubly sure she reached under me and squeezed my balls so hard I cried out.

"Up."

"Window"

"Have you spoken to him about what we discussed yet Jane?"

"No, I thought it better if we were all here."

The doctor took the lead, "Richard, yes Richard again now, you will not know that Emma is leaving us soon to go to medical school, so we are looking out for a replacement."

"Now Emma is like you in a way, as ones like you two do not come along too often, You are a natural submissive and Emma is a good student but one who likes to control. She was perfect for our special clinics and will be difficult to replace."

"That is where you come in. We have a short list of pre-meds who look like they may fit the bill, Emma has been sounding them out for me, but we need to try them out and we need a patient for them. Would you be interested in being that patient?"

"Before you answer that part, I also run extra tutorial programs for pre-meds but these ones would not be suitable for our special clinic. This would still involve hands-on examinations but no sexual overtones but purely learning exercises.

It took me a millisecond to think about it, "Yes I would love to help you out."

"I thought you would, just to let you know for the try-outs we will give you our special water for the desired effect, but obviously not for the other. In fact for those, I will be administering a large dose of a bromide-like drug to suppress any urges."

"As their hands-on insights progress, I will allow you to get hard naturally as many men do when examined to give them a taste of what might happen. But that is for the future and I will speak to you at length about it in the clinic soon"

Jane said, "Talking of a drink, you should have some water, don't want you drying up do we."

She passed me a glass of water and directed me back to the window.

What next I was wondering to myself. It didn't look like I would have Emma's hands on me again which was a shame.

"Put this on."

I was handed a rubber mask with holes just for the nose and mouth. Once on, I was blind.

Then I was manhandled to stand somewhere else and I heard, "Wait!"

I heard steps going away, a door opening, and then whispering, then steps approaching again. Was that more than one person now, it was very disconcerting as I just didn't know.

I heard the sounds of what sounded like someone undressing, but again I was unsure.

I heard the bed creak a little, and then I was manoeuvred until my knees hit the side of it.

"Get on the bed and kneel," Jane said.

I got on the bed and shuffled forward as I was directed and turned by a pair of hands. I felt my wrists grabbed and moved down to a shaven pussy. My head was then pushed down to between the legs. Who was this on the bed now I knew someone else was there.

My tongue and fingers went to work on a lovely-tasting fanny. The lips were swollen and my tongue found the clit and worked hard on it. I allowed my finger once lubed with fanny juice to seek out her secret hole and entered her. She did not resist as I pushed in further and she grabbed my head and pulled it hard into her fanny.

Then movement behind me, and someone came between my legs. Then they engulfed my cock in their mouth, what a wonderful feeling it was, Then the same hard vibrator was at my arse and pushed in deep on what must have been its highest setting.

Straight away I started feeling the erotic pulse that being fucked sends through me. I worked harder and harder on the fanny and could hear her breathing increase and she started to push at me and finger herself as well. My tongue was working overtime now and my finger in her arse was setting off spasms inside her.

At the same time, my arse was in ecstasy and my cock was ready to explode. My arse bucked up as spasm after spasm shot through me as the vibrator was hammering away deep inside me, and I could feel that I was about to shoot my load.

My cock was released from the obliging mouth and I could taste my cum as it hit the fanny of the one below me. I lapped it up eagerly still working her clit and arse and then she too came with an almighty scream.

It was not Jane but then who?

The vibrator was still buzzing away inside me, still sending wonderful feeling throughout my body.

"Get up and stand by the bed," Jane ordered.

I reached back to remove the tool.

"Leave it," she ordered, "I will let you know when to take it out."

As I stood, I heard shuffling, water running, steps, doors opening and closing and then nothing.

Jane made me jump as she said, "Take off the mask."

Immediately it was off I looked around but no one else was there.

"Wondering who it was I expect, just think it could have been anyone or maybe any two people. You know one was female but who was sucking you off. I can assure you it was definitely not me, no self-respecting mistress would do that to their slutty bitch."

The buzzing from the vibrator was the only sound now as she stood smiling at me, my legs were shaking as spasms of pleasure continued, and still no permission to remove it.

So I started thinking, two people then, how far away was the clinic I wondered, could it have been those two, no surely not, especially not the doctor.

This was partly confirmed by the doctor on the laptop saying, "Wow that was energetic and exciting to watch, I must say."

No sign of Emma on there though.

"You will never know, but we do and that is all that matters," said Jane.

"I am going to give you six more strokes for making a mess on my bed, for enjoying that arse fucking and simply because I want to."

"Stool, no this time just bend over, hands to feet. Are you watching over there, old man perv?" she shouted out.

Once I was bent over she pulled out the still-buzzing vibrator.

Then whoosh and whack, whoosh and whack again and again until the six were done.

"One more for me," she said.

This one was the hardest of all.

"Tell me how much you enjoyed that whacking, bitch,"

"Every stroke was amazing mistress, thank you so much," I said with tears running again.

"Good now stand there so he can see the marks for a while. Perhaps he is having a wank over it right now. Would that please you?”

"Not really mistress, I am not his to enjoy, only your enjoyment is important to me."

"Good answer bitch. Now go and shower and then come back here to dry off."

I went and showered, carefully soaping my sore arse cheeks, and making sure all the sticky spunk was gone.

I returned to her, towel in hand, she took it and stood me, yes, in front of the window and made a great show of drying me off. Paying great attention to my cock and balls. She was very rough drying my arse cheeks, deliberately so I guess.

She then surprised me by sitting on the chair and getting me to lie over her lap. I anticipated a spanking but instead, she rubbed some soothing cream onto the marks the crop made.

"See I'm not all evil, but I am thinking of dressing you again as you were earlier so that you travel home dressed like that."

"What would you say to that?"

"Erm, whatever you say mistress."

“Give me a minute to think about it. So assume your position.”

I heard her tapping away on the laptop, the video call had ended now.

Then I heard, "Good,” she returned to me and said, "The girls think it will be a good test for you, so I am going to redress you as I did before but with a shorter skirt. That's Emma's suggestion."

My cock was re-tied to the butt plug which was shoved in roughly with no lube and it hurt. Underwear, including stockings and suspenders, went back on, then the bra and blouse. No slip this time just a skirt with a split at the rear and was far too short for a middle-aged woman.

Then she applied make-up again, this time with a richer red lipstick, which in all honesty, coupled with the short skirt made me look like an old tart. The wig was finally put in place and secured and I was ready.

"You never know you might make some money as you travel home like that," she said with a smirk.

She gave me a light jacket to wear and a handbag and a bag full of my normal clothes.

"Keys, wallet, tickets and loose change are all in the handbag. Then she gave me an oversized brooch to put on the blouse. This is like a GoPro camera and records to a card, so do not cover it. When you get home face a long mirror or window so we know you followed orders.."

"Then remove the card and download it to your laptop and send it to me. Is that all clear?"

"Yes mistress, perfectly."

"Go on, send it as soon as you get indoors. Then put it back in the brooch and stay dressed as you are until you go to bed. I will contact you tomorrow for a further download."

I left and headed toward the station. It was late afternoon so it was quite busy. The train was packed with standing room only. To my horror, this sweaty old guy stood close up behind me and kept pushing his crutch into my arse. I tried to move but there was no room.

Then his hand squeezed my bum cheek, it was a difficult situation for me as I could not afford to make a scene for fear of being uncovered. I tried to ignore him, but then the dirty git ran his hand into the slit at the back and his hand reached up to my stocking top. Is this what women go through regularly on trains I wondered.

Well, I was no woman, so I reached behind and grabbed his cock and squeezed it hard. The old bastard had the cheek to smile and blow a kiss, so I went lower and grabbed his balls and squeezed and twisted them until I heard a little cry come from him. He quickly removed his hand and I smiled with satisfaction.

I have never been so glad to get off a train. From the station I walked through the town to my flat, ensuring I kept a lookout for people I knew. My building appeared and I started to breathe easier when to my horror, my neighbour came out the front door. It was too late to avoid her so I just kept walking, she looked at me as she passed, smiled and carried on.

Relief flooded through me as I shut my door behind me. I leaned up against it trying to slow my heart rate that had been going like the clappers since I left Janes. Then I remembered my instructions, I stood in front of my long mirror and said, "I'm home."

I took off the brooch, removed the SD card, downloaded the contents, attached it to an email to Jane, and off it went. I reinserted the card into the brooch, and then sat and watched the downloaded video.

Most of it was of other people but it caught my train journey in a reflection on the window and my interaction with the old man. It was pretty clear as well. I was caught in shop windows as well and quite frankly I was amazed at how convincing I appeared.

I had to sit around all evening with the clothes on and a butt plug up my arse. I eventually went to bed early as I desperately needed to pee.

As I undressed I carefully hung the clothes from a hanger on the door and finally, it was with great relief I removed the plug and my cock was released.

After using the loo, I lay on top of the bed thinking back on the day and what a day it had been. As I went through it in my mind I was subconsciously playing with myself and soon found myself hard again.

I shut my eyes and had pictures of the events racing through my thoughts, I started to wank, then reached down for my prostate vibrator. I couldn’t find the KY gel tube so I sucked on the tool to moisten it, then reached down and inserted it into my arse.

I had the remote for it on my table and pressed it and set it for a slow speed. My other hand was working on my cock, I gradually increased the speed of the tool in my arse. Eyes shut, I was trying to think of that sweet fanny I was licking and finger fucking.

That was not what came into view though, instead, I was watching myself being thrashed by the crop, harder and harder, I sped up on my cock and set the tool to maximum power. The images of the thrashing loomed larger and I exploded in a massive orgasm and once again was covered in my cum.

I got up and showered yet again and wondered what the future had in store for me.

If only I knew then what tomorrow was going to bring me.

TBC