Cross Dressing

18Jan 2018
 Dozy Doris humbled and taught respect.
I knocked on Mistress Helen’s door nervously. I didn’t know why she had summoned me but she had sounded cross.  “Get in, and take your shoes off, you worm!” she ordered. Once inside, she told me to stand up straight. “Do you know why I sent for you? she asked sternly. “No madam” I replied innocently.
“Well, I’ll tell you. Not only are you a useless dodgy bodger of a pervy handyman, but when you saw my maid this morning you upset her so much I’ve had to give her the day off!”
“Well, I did say she’s got a nice juicy pair, but I was talking about the fruit bowl. She must have taken it the wrong way” I said. “Don’t be stupid”, she said, slapping my face. “We all know what you meant”. I tried a different approach. “I was only joking,  trying to be friendly. It was just a bit of harmless banter”. Mistress glared at me. “Anyway” I continued “I thought she’d be flattered, and grateful for the attention”. It turns out she wasn’t! When in a hole, stop digging!
“You’ll be punished for your disrespect” she said sternly. “You will also be my maid for the afternoon, and serve me and my guest, Miss Wynters to you!”. “Maybe you’ll appreciate how hard maids work”. I noticed a lovely young woman behind mistress Helen, looking at me severely. “I can hardly believe his cheek!” she said. “He needs to be taken down several pegs. We could start by making him do a striptease”. “Good idea” said Mistress.
They sat down to watch and laugh at my clumsy attempts at Burlesque. “Don’t give up the day job” they advised. “Not that you’re any good at that either. Handyman? You’re not very handy, and certainly not much of a man, are you?” they laughed, pointing at the tiny todger between my legs. “Lets get it covered up. We can take him to the adult shop later, in his maid dress of course, and make him buy himself a chastity device, an extra small one of course!”.
They made me put on a pair of white ladies knickers, followed by the most ridiculously frilly pair of pink satin panties I’ve ever seen. A black satin maid dress followed, complete with frilly white apron, blond wig and lacy maid’s cap. “What a sissy!” they joked. “He looks rather frumpy”, said Mistress Helen. “Let’s give him a frumpy name”. After considering a few options, they settled on ‘Dozy Doris’ as being suitably humiliating.
My first chore was to skip and mince up and down the room, much to their amusement, to tidy my clothes, and curtsey to both when I had finished.
“Every sissy needs a collar and gag” said Mistress Helen. She put a pink ‘slut’ collar on me, and then stuffed a pair of black panties in my mouth, followed by a wooden penis gag to keep it all in place. “I love that gag” said Miss Wynter “We hear so much nonsense from male chauvinistic pigs like him that it’s a relief to be able to shut one of them up. Let’s keep him like that all the time”. “Way ahead of you” said Mistress as she clamped my nipples and attached the connecting chain to my gag to keep my head bowed. The clamps were fitted with little budgie bells so I tinkled as I moved, which they found highly amusing.
I was put over their knees and they both gave me a good hand spanking. “That’s just a warm-up” I was told. “There’s plenty more where that came from, so you’d better buck your ideas up and behave. Now get in the kitchen and put the kettle on!” I turned to obey, but was called back. “Rule 1; Curtsy to us both EVERY time we speak to you”. she warned.
I served them both a cup of tea, and a chocolate éclair. While they enjoyed their refreshment, I had to massage Miss Wynters’ feet. I hope she liked it as much as I did. Once they had finished, I had to tidy their plates away, before being told to stand in the corner with my hands on my head. As Miss Wynters spanked my sissy backside, she told me how good it felt to put a worthless male in his place, and that I had better get used to it. Meanwhile Mistress Helen fetched some rope. What more indignities are they planning for me?
First of all I had to sweep up the mess that Mistress’s pussy (Cat) had made. Then they decided I should polish Miss Wynters’ shoes, while she was still wearing them. The wooden penis gag was replaced with a harness panel gag. This had another pair of panties tucked into the strap, with which I did the polishing. Mistress Helen stood behind me with a wooden spanking implement, to make sure I was giving the task my full attention. Eventually they gave their grudging approval to my efforts.
“He could do with some down time” said Mistress Helen. “Let’s tie him up. We can discuss how we might be able to make some money out of him”. Still gagged, I had to lay on the floor as Mistress  Helen secured my wrists behind my back and Miss Wynters bound my ankles. The ankle and wrist ropes were then tied together to put me in a hogtie. “That’s  sorted him out; but we don’t want to look at his ugly mug, do we?” said Mistress as she put a pink satin hood over my head.
I had to lay there, ignored, while they talked about their various ideas to hire me out to neighbours as a cleaner, or have me trained and restrained as a ‘male pleaser’ and spanking target at their BDSM parties. Alarmed at this, I grunted some involuntary protests. Mistress hit me and told me to be quiet. “If I want your opinion, which I don’t, I’ll remove your gag. Until then, keep quiet!” she said. They told me to struggle to get myself free. I did my best, but I was clearly going nowhere until they untied me. Yet another reason to mock!
Eventually they did release me, only to bend me over the sofa for another good spanking. They hit me in unison on each butt cheek with leather straps. “That’ll teach you to try and speak with your mouth full!” said Mistress Helen. “Speaking of mouthfuls, let’s see how you get on with a bit of dildo worship.”
They each had a massive (compared to my puny penis) dildo. After my gag was released, I had to put condoms on using only my mouth, before giving them each a good oral servicing. “He’s not up to much, but I suppose he does make a passable gobbling teasemaid” said Miss Wynters with a laugh. I took that as a compliment; the only one I was likely to get.
“Go back to your corner and keep still while we think about what to do with you”. I obeyed, but unfortunately I fidgeted 3 times, which earned me a further 3 dozen strokes on my bare, already sore, red backside; 18 from each lady. I had to count them out. Mistress Helen went first with a hair brush and a wooden spoon, and Miss Wynters followed with more of the same. I managed to avoid her attempts to trick me into miscounting, so Mistress finally gave me a few extra ones anyway, “for luck”.
My lesson was nearly over. I had to curtsy to each of them in turn, thank them for their correction, and promise to be more respectful to women in general, and maids in particular. With a final slap on the face I was dismissed. “Get dressed and get out of our sight!”
22Mar 2017

Double Domination with my gorgeous T Girlfriend Tiffany on Thursday 18th May 2017

The lovely Tiffany will be joining forces with me on the above date for lots of #DoubleDomination fun, come and explore your fantasies with us.  https://twitter.com/TiffanyAching4

Spit roast, double domination, four hands massage and much more

One hour double domme £180 a non refundable deposit of £60 paid in advance, balance in cash on the day.

90 mins double domme £280 Deposit as above

Two hour double domme £350 a non refundable deposit of £100 paid in advance, balance in cash on the day.

ALL bookings enqs through Mistress Helen Ryder, once you are booked in and the deposit has been paid then a brief chat with Tiffany can be arranged.

Please note: I do not profit from other adult providers, we are simply playing and helping each other out in sessions.

 

 

 

21Feb 2017

The Lingerie Model & Lingerie Cross Dresser

Heading backstage to my private dressing room I couldn’t wait to crack open a bottle of bubby and have one of my slaves pop by for a nice relaxing foot massage.  I happen to be a mature lingerie model and Dominatrix.  Taking part in a catwalk show always leaves me elated with the pounding music, the cheers of adoration, the vibrancy and upbeat of the show etc it’s always so exciting.

On entering the room I was rather surprised to see Dennis one of the designers I had been modelling Retro lingerie for running his hands over a pile of satin and silky chemises, French knickers and fully fashioned stockings.  Designers sent me free samples all the time so it wasn’t unusual to come back to a pile of offerings after a show.

“Hello Dennis, I’m surprised to see you in here” he hadn’t heard me enter the room as he was so engrossed in what seemed lovingly and longingly touching the garments.

“Oh Helen you caught me by surprise I thought you would be at the after party in the models main changing rooms” Dennis looked rather flushed and slight perspiration was glistening on his face.

I decided to play a game and flung off my favourite Satin robe from What Katie Did https://www.whatkatiedid.com/en_gb/product/1372/lounging-robe-black-satin-1930s over a chair and stand there hand on hips wearing a set of lingerie from Dennis’s new collection.  The sheerest black tulle net and pink lace with a matching thong with a wisp of fabric moulding around my hips and going up between firm round buttocks’.  A matching skirted suspender belt skimming over shapely hips and bra encasing my full breasts.  My pink pert nipples just peeping through the sheer fabric.

Dennis stood there perplexed and his bright blue eyes seemed to light with joy “Oh Helen, you are such a vision” He seemed to be speechless after making that statement.

“Dennis have you ever worn any of the garments you make or tried those styles over there? Waving my arm towards the pile.

“No Helen but I would love to” he looked down at my feet smiling as if not knowing what to do next.

Naturally I took the lead and walked towards him and leant forward gripping hold of his polo top pulled it off over his head “well you can’t try it all on wearing those” I undid the button on his trousers and slowly unzipped them licking my lips suggestively.

Easing on a retro style corselet and then fully fashioned dark grey stockings and a silky pair of French knickers Dennis looked a picture.  I had him stand in front of the full length mirror and lightly ran my hands all over the fabric and at the rapidly growing bulge in the very silky lace edged French knickers.

“Helen this all feels so good but I feel so naughty” Dennis said rather huskily and it was so obvious he was getting off on dressing up with me there.

“Well you are a naughty boy come here” I sat on the dressing rooms chaise lounge and patted my lap.

“Over my knee you naughty boy I think you need a good spanking” well it was a matter of seconds and he was over my lap and wriggling onto my thighs, stockings upon stockings rubbing and a very erect cock just between the tops of my thighs as I placed one leg over his and trapped him in place.

“awwww awwww I’m such a naughty boy, spank me harder Mistress Helen please”

Well I couldn’t possibly refuse, thrashing his buttocks in a flurry of hand spankings and my hairbrush close by I reached for it and used that too.  Bring down the brush a little harder each time and he wriggled harder and harder against my thighs.  Watching his orbs glow redder and hotter I ran my hand over his bottom teasingly.  Followed by a flurry of hard spankings.

“Dennis I can feel your cock humping my thighs you beastly boy, and it feels wet!  I bet there is pre cum rubbing against my silky stockings you filthy messy beast”

He rubbed and bucked harder as my spankings got harder and more persistent and suddenly he cried out with release pumping hot sticky cream into his panties.

“Oh Helen that was amazing” breathless he dropped to the floor and lay on his back.

Smiling and looking down on him I stood legs spread over his face “well I don’t think you have learnt your lesson yet boy” I lowered down onto his face so he would be breathing in my essence as I sipped Champagne and sent a text to my slave that I was ready and to bring along one of my girlfriend models on his way past the main dressing room and an extra bottle of bubbly.  I was felling rather mischievous and wanted to play some more.

Mmmmm yes bring my favourite friend Melissa to the party………………

 

To be continued………maybe………………………………

13Jun 2016

**All photos used with approval of the subject with some edits to prevail identity, fantasy/fact/fiction with no harm to the participant, transient stripes and theatre style roleplay***

It had been a long day dealing with all the miscreants of the finishing school for young ladies and there was just Loretta Cox left to deal with in regards to inappropriate school uniform and her general behaviour.

My name is Helen Ryder and I am the new head mistress at the Burgess Hill academy. I am very keen to implement some new techniques such as aversion therapy, which Loretta would be receiving very shortly!

“Come in Loretta”

“Yes miss”

“Let’s have a good look at your uniform today, do you think you have stuck to school rules Loretta?

“I think so miss”

I lifted up Loretta’s skirt exposing a pair of non-regulation red panties with love hearts on them as well as sheer black lace top stockings.

“These are NOT regulation navy or black knickers Loretta, and wearing black stockings tut tut, you should be wearing long black school socks”

“I thought now I’m a big girl miss I can wear stockings”

“Oh no you can’t young lady, you break school rules and you pay the price, you are going to be spanked”

I grabbed Loretta and pulled her across my knees with head down low and bottom up high I spanked her over her non regulation panties and then to Loretta’s humiliation I pulled them down and spanked her bare bottom!

“Get up Loretta and pull your knickers up”

Loretta’s face was very red and almost as red and glowing as her bottom.

“You are dressed like a tart under your school uniform and as for the length of that skirt, which is very questionable”  “Dress like a tart then be treated like one, that’s my motto”

I  marched Loretta into a class where young ladies were taught the basics of beauty and started applying lots of make-up and red lipstick, it wasn’t long before Loretta was looking like a cheap tart.

“Stand up and look in the mirror”

Loretta stood in surprise at her very slutty appearance “Oh miss I look so grown up” she said smiling and twirling in front of the mirror.

”I was shocked that she had the audacity to look pleased with herself, well you are over 18 Loretta and being as you are so keen to look the part of a slut then you will be treated as such”

Having attended a very forward thinking course recently I had a bag of interesting items for aversion therapy.

I strapped on my black leather harness with a red veiny cock and gave the slut a condom “Loretta I think you can demonstrate how to put this on with just your mouth if rumours are true”

On her knees with her mouth full of cock Loretta certainly seemed to have had some practice and was soon deep throating and gagging on the cock.  Such a shame Mr Baxter the deputy head wasn’t around for Loretta to work on the real thing.

“Get up little slut and over that bench”

I strapped Loretta down to a black leather bench and stood right behind her telling her I was going to make use of her little fuck hole and make her very sore and that it would indeed be punishment and she would be so sore afterwards that she wouldn’t be so quick to bunk off after hours and sneak off to the local barracks and play with the squaddies.

Noticing some unruly public hair I got out a shaving kit I had seen in the beauty room and made her silky smooth.  I applied lots of wet sticky lube to her little fuck hole and finger fucked her first, opening her up and getting her ready for some cock.

I positioned myself behind her thrusting hard in one whole length into her tight fuck hole. Loretta instead of crying out “please stop” she was groaning and asking for more!  I worked her in every position with bigger thicker cocks and the greedy slut was still asking for more until I had her on her back on the gyno bench with her legs right over my shoulders banging her hard and fast.  Only stopping briefly to shave her a little love heart above a very excitable engorged clitty which was very moist.

It was at that moment I thought to myself why bother trying to curb a young ladies sexual appetite and simply encourage her instead, after all I could continue having a lot of fun with Loretta and encourage her to make use of her talents on webcam and getting paid for entertaining the local men as well as encouraging her into a very promising career in porn.

“Get off that bench Loretta and stand over there” I indicated pointing to the other bench ” bend across that spanking bench and stick your bottom right out”

I reached for my very thin cane known as the bastard and told Loretta that as her new head mistress I might well encourage her natural talents but she wasn’t getting off so lightly for her earlier cheek and she would have 12 of the best.

12 strokes later and one very welted red bottom I told her to pick her panties up and dismissed her.

What an end to the day I thought with a smile on my face.

 

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16May 2016
“Panty Perv gets spanked humiliated.”
This is an account of my recent highly enjoyable visit to Mistress Helen. If you ever feel the need to be under the control of a gorgeous dominatrix, great at role-play, with a sense of fun, who can also be strict and severe, then a visit to Mistress Helen Ryder certainly hits the spot.
I was supposed to be measuring up for a decorating estimate for Miss Ryder when she caught me sniffing panties from her washing basket. I was so engrossed that I didn’t notice her filming me on her phone until she barked “put those down you filthy pervert, and get in here! Now!”. She twisted my ear and pulled me into her work/play room. This was full of BDSM equipment: spanking bench, canes, crops, floggers, paddles, cuffs, ropes, gags, nipple clamps, and lots of other stuff I didn’t recognise.
“I’m Mistress Helen, a professional dominatrix” she announced as she slapped my face, “I have perverts like you for breakfast. If you don’t do that work for me for free, I’ll put this film will be all over the internet, with special attention for your wife and your boss. Do you want that?” I admitted that I’d rather she didn’t, and had to accept her demands. A few unpaid hours painting wouldn’t be so bad, and I hoped she would let me go.
“Not so fast” she said. “I’ve bought some new items, and I can try them out on you. Won’t that be fun?”. She didn’t wait for my answer. First up was a very large sissy maid costume. “Get undressed, and look sharp about it!” she ordered. When she saw I was wearing ladies panties with ‘PLEASE SPANK ME’ written on the back, she laughed, before obliging with a leather belt (“seeing as I’d asked so nicely”). I took them off, and she laughed even more at my chastity device. Forced to my knees, hands on head, I had to explain that my wife makes me wear the panties and device because she doesn’t trust me with female customers. “Don’t all wives do this?” I asked, but I just got another slap.
I was put into the dress, with matching panties, suspenders and stockings, a blond wig, and a frilly white hat and apron. “Very fetching” she said. “Give us a twirl and some curtseys”. I did as I was told. “Hmm. You’re about as elegant as an elephant!” she pronounced, as she put me in handcuffs, anklecuffs and nipple clamps. She ran another chain from my clamps to the ankle chain, so I could only take short mincing steps without pulling on my nipples. I was gagged with my own panties, held in my mouth by a bone shaped bit gag. “Sissies should be seen but NOT heard” she told me. Finally, a pink ‘SLUT’ collar with tinkly bells on was buckled round my neck.
 “You might look the part, but how good are you at chores?” she asked as she gave me a pink feather duster. She picked up something painful-looking that was like a short bullwhip with a dragon’s tail on the end, and marched me downstairs to dust her living room, casually flicking my backside with the whip as I did so. Ouch!
Dusting done and dusted, I had to serve her a cup of tea and then polish her shoes with the panties in my mouth while she sat and sipped her drink. By now I had been given quite a lot of penalty points for doing things either wrongly or too slowly. I was taken back upstairs, dusting the handrail as I went, and strapped to her spanking bench. She told me that 40 strokes from various implements, ending with 10 from a cane, should buck my ideas up. The cane was new, as she had recently broken her old one on another slave. I prayed she didn’t want to test this one to destruction too. It hurt, but the cane survived (and so did I) and I was released for my next chore.
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My gag was replaced by a rubber penis gag with a dildo sticking out the front. (I secretly hoped she might sit on it and bounce up and down, but no such luck.) No; she taped a pair of panties on the end, and led me into her spare room, which was full of shoes and boots. Despite my predicament, I couldn’t help laughing at how many pairs there were. For this I was punished. She replaced my clover clamps with a similar but far more painful pair with much stronger springs, and told me I would have to wear them for at least 5 minutes. She then looked for the first clamps. I tried to tell her through my gag that they were still attached to my chains. For grunting out of turn, I was sentenced to 30 minutes in the new clamps. A bit harsh, but when she saw I was actually being helpful she relented, and reduced the time to 10 minutes. “Be grateful for small mercies!” she told me. I could only nod in agreement.
I polished the shoes, and then two rubber dresses, with my duster gag. She removed the clamps, and put me back on the bench for another 30 or 40 strokes before letting me up again. “Stand there, and DON’T look round”, she ordered, as she pushed my nose into the doorframe. When she was ready, she led me by my ear to the bathroom, where I had to clean the washbasin and toilet. Thankfully I could use the brush instead of my tongue!
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For my final dose of discipline, she removed the penis gag, and put my dribble soaked panties back in my mouth, held in place by sticky tape. This time I was secured to the bench with wrist cuffs as well as leg straps. “Blimey, how hard is she going to hit me?” I trembled. Fairly hard, as it turned out, but in hindsight it could have been worse.
I was released, and made to curtsey several times, each one lower than the last, while thanking her for her correction. I had to promise to mend my panty sniffing ways, and she reminded me what would happen to the film she had taken of me if I ever lapsed back into my old habits.
With that, she told me to put my ordinary clothes back on. My only underpants were the soggy panties that had been used to gag me, but they did at least feel cool and soothing on my hot, sore, stripy red bottom. I half expected them to start steaming.
Yours
Pansy Penny
17Mar 2016

Sissy Maid Cherry roleplay and humiliation.

A new maid was due for an interview/session and in the sissy boudoir out lay her new uniform, stockings, dress, and black satin bloomers along with a cute frothy lace edged pinny.

The doorbell rang and Mistress Helen Ryder greeted the new maid who had no name at this stage and took her up to the sissy boudoir room.  Chatting away about past experiences and what would be expected of her today the maid looked quite nervously excited.

“I must confess Mistress Helen that I just want to be a ladies maid and wait upon her”

“Take off those manly clothes, and dress in these” Mistress Helen indicated the clothing pile and helped the maid ease on her stockings.  Not being sure if the bloomers would fit but they were in fact a perfect fit for the maid’s cockette.

“What size shoes are you sweetie?

“I’m an 11 Mistress Helen”  How very fortunate for the maid as a size 11 in low heeled patent court shoes was produced from a rack of shoes and slipped on nicely.

Mistress Helen expertly applied full make-up and then selected a cute wig with a gorgeous shade of strawberry blonde and little flicks and curls.  Placing the wig upon the maid’s head an Alice band was added, it finished off the look perfectly.

“Now stand up and give me a twirl and a curtsy” demanded Mistress Helen.

The maid did exactly as she was told executing a perfect curtsy too!

“Now look in the mirror my dear and look hard and I want you to think whether you might be a Joanna or a Cherry as your new name”

“I really don’t know Mistress” the maid said with her eyes downcast.

“I think you will be known as Maid Cherry from now on, it’s time for basic household duties so follow me”

Maid Cherry followed her new Mistress down to the kitchen where she was instructed to make the perfect cup of tea.  “I like my tea a deep golden, not weak, not strong and not too much milk so you had best get it correct”

Mistress Helen sat down on a chair and maid Cherry made the tea.

“Mmm a bit weak, pop the teabag back in for a while and if no improvement then you will start again” Mistress Helen Ryder was a hard task Mistress at times!

The tea was taken away and modified to Mistress’s liking and maid Cherry was instructed to carry out some shoe cleaning on the very shoes that Mistress had on.  “Plenty of licking and huffing on them before you buff them to a high shine, come on I want to see my reflection in them”

After the shoes were polished Mistress Helen indicated a high heeled pair of patent leather boots were to also be shined as they were required for a session the next day.

“Whilst you are busy cleaning I will choose a nice neutral colour for my nails, as you will be giving me a mini manicure maid Cherry”

“Yes Miss, I might not be very good though, but promise to try my best”

Mistress Helen returned with a bottle of polish, some pads and a bottle of acetone (just in case) and demonstrated how to paint nails.  Very shakily the new maid painted her Mistress’s nails, they didn’t look too bad but clearly the maid needed more practice so she was instructed to paint her own nails.

“Getting slightly better maid Cherry, ok now time to take it off” maid Cherry was given acetone and pads but made a mess of the removal with squeezing too hard and making a mess with drips of liquid falling to the floor.

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“You have earned yourself a spanking young lady” Mistress Helen indicated for maid Cherry to follow her upstairs and to bring a feather duster for dusting all corners of every room on her way and upstairs too.

“I’ve decided to allow you to pamper me some more first, you will wash my feet after I have removed my stockings and massage my feet and legs with this lovely massage balm.  Then brush my hair and massage my head with this special device and then brush my hair again”

Maid Cherry was kept very busy for some time with being on Mistress pamper duties and was clearly enjoying her new role, she hoped that Mistress Helen might forget the tea not being to her liking straight away and the droplets of nail polish remover.

“Mmmm that was very nice maid, now curtsey six times each becoming lower” and then over my spanking bench”

The maid lay across the bench and Mistress Helen pulled her new uniform up over her waist exposing the black satin bloomers.

“20 spanks on each cheek for making mistakes”

“Ouch, ouch” maid cherry wriggled on the bench with her little cockette rubbing against the satin bloomers she was becoming very aroused.

“Well what do we have here?  Is your little cockette growing in those bloomers you naughty girl?!” Mistress Helen picked up her vibration wand and teased maid cherry with it, teasing and teasing some more that oh dear too late what a sticky mess in the bloomers!  Oh dear the humiliation!

Maid cherry was instructed to wash them by hand in the bathroom sink, make-up removed and boring manly clothes returned she was sent on her way with instructions to return another day.

Maid cherry had an embarrassed little smile on her face and her little cheeks were glowing with pleasure.

 

One of my favourite tea manufacturers is http://www.twinings.co.uk/  and if anyone buys me that Red Velvet Easter egg on their front page I will be very happy!

This is useful for all things sissy related http://www.thesissystore.com/

 

23Jan 2016

2pm sharp the phone rang “Hello Mistress Helen it’s slave Lenny I’m parked up as instructed”

Mistress Helen looked out across the road and saw the car as described and gave the house number and instructions to come straight across.

“Hello Mistress Helen, it’s great to meet you at last”

“Jolly good to meet you slave now come and follow me up to my special room”

Mistress Helen led the way and slave followed taking in MH’s lush curves, shapely bottom and long legs catching a peek of her stocking tops as she walked up the stairs.

Slave handed over the remainder of the tribute due with nervous excitement.

Mistress Helen walked around slowly instructing slave to strip.

“Mmmmmm slave lenny, you do look rather familiar and we have already met previously I believe”

Standing naked in the room slave gazed down at his erect cock, he was nervous about where Mistress recognised him from and it led to his excitement wondering what would happen next.

“How is Amy? Mistress asked giving slaves erect cock a little slap with her crop.

“Oh fuck!  You won’t tell her I’m here will you?

“Well that depends on how much you entertain me today slave” Mistress grinned mischievously and walked out of the room returning with a large box.

Mistress Helen produced stockings, a very frilly pink and black suspender belt skirt, a bra with false breasts and a tight wiggle dress.

“First of all this clitty cock needs to be kept under My control” a sissy pink gingham ribbon was tied around slaves balls and criss crossed over and around his throbbing cock (it felt rather good) and on went the stockings and very frilly suspender belt, bra and then the dress.

“Look how pathetic you are in that mirror”

Slave walked over and gasped as Mistress laughed at him.

“I have news for you, I used to work with Amy and had many a conversation about how you simply don’t satisfy her with that thing!  I hear you only last about three minutes and as much as she loves her home life and generous income from your joint jobs, she is bored sexually and we have been chatting about cuckolding”

“She hasn’t told you that surely” spluttered slave Lenny

Mistress Helen told SL all about the intimate chats between her and Amy and that being as slaves little 3 minute egg timer would never satisfy her that Helen would be simply helping her friend Amy by training slave up to be a useful entertaining cuckold husband.

Amy worked for an international company and it often involved working away and with her new very good looking boss David who Mistress Helen had recognised from some of the fetish parties she had attended.  She knew David to be a very accomplished dominant and knew him to be into the cuckold lifestyle.  She would encourage her friend to enjoy those trips away whilst lenny kept the house clean and tidy for her arrival home.  He would be hand washing her sticky lingerie on her return.

Mistress Helen strapped into her harness and placed a decent sized cock in it. “Get those cock sucking lips around this slave”

And so began slave lenny’s training as for the next couple of hours he was made to entertain Mistress Helen with stripper style dancing, made to confess his failings as a lover and how he would write a letter to his wife pouring out his failings and how much he loved her and wanted them to have a happy marriage and his wife a fulfilling sex life with David.  He would be waiting on their every need, being fluffer and cleaning up as and when required.

His training consisted off lots of cock sucking, then having his own anal cherry taken over the bench so that he could be a true bitch.  Shoe cleaning and shoe worship progressing on to bare feet which Mistress Helen had deliberately made as sweaty as possible, instructing slave to get his tongue between every toe and lick them clean.  It was only when he was totally exhausted and totally compliant and ready to write the letter to Amy that Mistress Helen made him kneel on the floor and wank his little cock and make him spurt all over the floor.  His face was pushed down into it and he knew what was expected of him.

“That’s right slave from now on you will be on clean up duties, you will be put into chastity in time and only given permission to cum when it suits either me or Amy.  Now get practising and lick that mess off the floor”

Slave licked the floor clean and then had to wash it by hand too, Mistress Helen threw his clothes at him and told him he was dismissed until another time…

Mistress Helen provides training and role plays in person for sissy cuckold husbands with strapon training, sissy make overs and for those not brave enough to attend in person or wanting long distance training there are websites out there such as this one https://www.sissify.com/sissy-training-assignments/  I can not personally vouch for the site so do your homework!

 

sissy training cuckolding

04Nov 2015

Received from PVC slave, a long overdue piece of homework to include his history, experience and fantasy session.

****** All scenes that I play out are always SSC SAFE SANE CONSENSUAL!******

 

pvcslave Sissy makeover and Pegging

It is fair to say that i have had submissive tendencies for as long as i can remember, and this resulted in frequent fantasies and viewing of such material in magazines and, as it became available, on the internet.  As time progressed, my interests expanded to include a fetish for pvc and plastic which in turn introduced me to the world of FEMDOM.  Whilst not a masochist and not especially interested in the corporal punishment aspects, i started to widen my fetish base.

These tendencies remained even after my marriage, and whilst I tried to interest my Wife in my desires, She had no interest at all in participating.  Over the first few years of marriage, all overtures were rejected, and eventually She agreed that it would be acceptable for me to investigate and “indulge” my desires as long as She remained largely unaware of what i was doing.  This arrangement continued for a few years, with me undertaking a number of visits to professional Dominatrixes, almost always with disappointing results.

These visits did, however open my eyes to the much wider aspects of FEMDOM, and i soon developed an interest in becoming feminised and even an interest in becoming a sissy.  This continued to grow as an interest for me, although still without any interest or contribution from my Wife, although She was aware of most of my secret desires!

As time went on, i started to collect a wide variety of  pvc and plastic items, as well as a number of bondage items.  Experimentation was still however, limited to the occasional visit to a professional Mistress.

A few years ago, i came across an advert for a West Sussex Mistress (now Mistress Helen), and arranged a visit to Her which was the beginning of a whole new trend, and one which continues to this day.

Following that initial visit, (which proved to be rewarding in a way all previous visits to Mistresses had never been) Mistress Helen introduced me to aspects of FEMDOM i had previously not experienced, and pushed my boundaries little by little.

A major lifestyle change occurred when my Wife and i were holidaying in the USA, and a TV documentary programme came on about Female Led Relationships, with examples of how these relationships had changed a number of marriages.  When it came on the TV, i fully expected my Wife to insist on changing channels, and i even suggested doing so myself.  To my surprise, She stated that it might be interesting to see exactly what my fantasies meant in real life to others.  We watched the programme to a conclusion, and very little was said.  It was a couple of weeks later once we had returned home and after that, that things changed dramatically!

As i returned home one evening, i was greeted by my Wife and told to sit and listen.  i sat dumbfounded as She explained to me how the documentary we had watched had made Her think about the whole concept.  She also explained that the whole FEMDOM/FLR issue had cropped up during a “girls evening” where it transpired that one of Her long time friends, Debbie, admitted that She dominated Her husband, and that he was Her full time slave, and how much better Her life had become as a result.  This triggered many conversations and prompted my Wife to decide to follow Debbie’s example and to agree to my many previous requests to dominate me and take me as Her slave.  Although She made it very clear from the outset that the arrangement would be on Her terms, and in no way simply to meet and fulfil my fantasies, i could never have envisaged how much my life was going to change.  Although i was given plenty of time to think about Her proposal and make my own decision to agree or not to serve Her, it seemed too good an opportunity to miss after all my years of requesting just what i thought was being offered, and of course i agreed.

If i had any idea that what was to follow would prove to be quite so far removed from my fantasies, i guess i might never have agreed!  Indeed, Lady Jane – or Goddess (the title my Wife thereinafter insisted, and still insists upon, had even produced a “Slave Contract” for me to sign which, accompanied by some very compromising photos, was to prove Her hold over me in all things, and prevent any thoughts i may have had to back out after that.

As a result, and within days, all my male underwear was removed and all but a couple of items (which She held) destroyed, and i was made to wear female underwear – my sissy panties – at all times, further increased when so desired by Her to include tights and even stockings and suspenders. As if that were not bad enough, i was also informed that i was to be placed into chastity to prevent myself ever being able to masturbate, and that sex was to become something for Her pleasure and to Her timescale.  i was also told that my position was such that all pleasure was for Her alone, and that what i desired or wanted was of no importance at all.  This, i was told, meant that i could expect to provide Her with oral sex whenever She so desired, and for as long as She desired.  i was then fitted with a CB6000 chastity device and locked up, and have essentially remained caged ever since, with only brief and occasional freedom.

Over time, more and rules were issued and my slave contract amended to reflect my ever diminishing status.  i was also permitted to attend and serve Mistress Helen as there remained some aspects of my training that She was still reluctant to address and carry out.  i also discovered afterwards, that Lady Jane was in email contract with Mistress Helen and discussed and arranged some details of how my sessions were conducted.

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One such session that further changed my status, when i was actually instructed by Lady Jane to arrange a session with Mistress Helen.  After several previous sessions, which were as much to cater to my fetish desires and to explore my submissive nature,  Lady Jane made sure that She played an active part in the content of this session, and how i was to prepare for it.   Making it clear to me in advance that i was to make contact withMistress Helen and book a session with Her, i was given a locked case and envelope to take with me the morning of the session and was told to present both to Mistress Helen when i arrived.  i was to have no doubt that this was another potential turning point in my life, when i was also made to wear full feminine attire under one of my pvc maids dresses, and to take along my 4 inch stilettos.  Although i was permitted to cover myself by wearing a shirt and trousers for the journey, this did little to make me feel anything other than vulnerable as i drove to my session with the case and envelope sat on the passenger seat of the car as a constant reminder of what was going to await me.

After knocking on the door at the agreed time, i was let in, and after having presented the letter and case, and of course kneeling to conduct my formal greeting to Mistress Helen, i was ordered to strip down to my maids outfit and present myself for inspection.  To my surprise, i noted that Mistress Helen was wearing a raincoat – hiding what She might be wearing underneath – although Her stiletto heeled shoes were clearly visible.  Without offering any explanation for the coat, and after pointing out one or two errors in my presentation – for which i was promised suitable punishment in due course – i was made to make my way down to the dungeon and kneel facing away from the stairs, and await Her arrival.

As i knelt in the middle of the dungeon floor, i could not help but notice the array of punishment instruments laid out on the whipping bench and hanging up along one wall, nor the selection of dildos alongside a strap-on harness on a small table in front of the St Andrews cross.

After a few minutes, a heard the unmistakable sound of Mistress Helens heels coming down the stairs.  By this stage, i was visibly shaking with nerves, and had to force myself not to turn around and look.

Once down the stairs, the sound of Her footsteps continued towards me until i was aware of Her standing behind me.  With an instruction to open my mouth, a ball gag was soon secured in my mouth; necessary i was told that, as She was sure i was not going to like what She had to tell me, and that She had no desire to hear any pathetic pleas from me.

Only at this point did Mistress move in front of me so that i was able to witness for the first time what She was wearing.  Unsure beforehand what to expect, i was surprised to see that She was wearing A black PVC top and knee length matching skirt.  In one hand She now held the case Lady Jane had had me bring, and in the other the now opened envelope.

Placing the case down on the bench and opening it away from me so that i could not see what was inside, Mistress Helen proceeded to inform me that my Wife had not only already exchanged emails with Her, but also written a note with suggestions as to how She might choose to conduct the session.  She informed me that the contents of the emails and note were to make it clear that this session; unlike those that had preceded it; was intended to be one to punish, humiliate and generally abuse me, and that my wishes and desires were of no importance.  Not only that, but that the session was to last not one hour as i had imagined, but two!  It was also explained to me that the session was intended to subject me to much wider aspects of BDSM than had been the case before.  Specifically, that i was to receive strict and harsh punishment, and that – as befitted the sissy slut that i was attired as – i was to be treated as one, and was to be subjected to a pegging to re-enforce my sissy status.  It was also explained that since i liked PVC and plastic so much, it was only fair that that should play a significant part in the session, but as a form of aversion therapy rather than anything for my enjoyment.

At this point, Mistress produced from the case two PVC macs, and no less than three PVC hoods, stating that She had every intention – at Lady Jane’s request – of using as much PVC as She could to instil in me an association with PVC that would change it for me from something i enjoyed, to something that i would come to dread instead.  It was made clear to me that the intention was that i would be made to wear PVC macs and other PVC and plastic clothing, and come to associate wearing them with humiliation and punishment, and that breath play inside PVC hoods was to become a method of punishment not pleasure, and that finally all previous pleasure or enjoyment as a result of being face-sat would become something to be feared and no longer enjoyed.

As the implications of all this started to dawn on me, She told me to stand up, and clearing the whipping bench of the case and laying it and the various punishment instruments on the floor, She told me to put on the pink PVC mac that She then picked up.  Taking the mac from Her i started to put it on, only to receive a slap across my face, telling me that it was not to be worn normally, but back to front.  This initially confused me until when She had done up the mac at the back, She proceeded to pull the hood over my face and tie it behind my head, informing me that my “PVC aversion therapy” had begun already.

Leaving the mac on, complete with the hood up, i was told to put my hands behind my back, and She proceeded to secure my wrists together in a set of wrist cuffs.  The fact that i was now unable to use my hands to remove the hood even if i wanted to was immediately evident to me, although She took pleasure in explaining to me that my fate was now out of my hands and completely in Hers.

In this helpless condition, i was gently lead over to the whipping bench and told to bend over it.  My ankles were then cuffed to the back legs before my wrists were released, only to be re-secured to the front legs, rendering me helpless.  A further strap was then secured across my back to compete the bondage.  Only then was the mac hood lowered.

Grabbing my hair and pulling my Head up so that i was looking at Her, Mistress Helen informed me that the first of my punishments would now take place.  i was, She informed me, to receive 6 strokes each from a leather strap and a cane as requested by Lady Jane, after a suitable period of ‘warming up’ from one of the floggers.  This punishment was also – again at Lady Jane’s request – to be administered without recourse to a safe word.

This obviously amused Her, as it had become clear from previous sessions that i had a pretty low pain threshold.  Needless to say, it hardly struck me as amusing!  Neither did the fact that She informed me that the punishment was to be administered across my bare bottom.  She then proceeded to undo several of the poppers on the PVC mac, informing me that the other advantage of my having to wear the mac back-to-front was that it made it easy to expose my bum whilst making sure i still had to wear the mac!  My sissy knickers were then also lowered to ensure that i was fully exposed, allowing Mistress to see for the first time that i was caged in my CB6000 chastity devise, something which She also took advantage of to humiliate me still further.

Returning to stand in front of me, She showed me the flogger She held in Her hand, informing me that in future, when not gagged as i now was, i would be made not just to kiss the instrument i was going to receive, but also to beg Her to use it to punish me.   That would come later during the session i was told.

As Lady Jane was not that keen on inflicting pain on me Herself (though certainly not adverse to having someone else do it..) the effect of the flogger when it started was unpleasant.  And the fact that this was just a ‘warm-up’ was not lost on me either.  After what must have been about three minutes of this, i was already feeling the pain, and was far from looking forward to the strap as this too was shown to me before She took Her position behind me once again.

The first stroke of the strap felt as if my already sore rear was on fire, and by number 4 i was already groaning into the gag.  By the time all six had been delivered, i was yelling into the gag.  And yet my ordeal was still not over.  Once more i saw Mistress Helen in front of me, this time flexing a vicious looking cane.  The look of fear in my eyes must have been clear, as She laughed sadistically and informed me that the cane would be far worse than the strap, so i had better prepare for the worst!

As the first stroke from the cane landed across my rear, i was left in no doubt that her warning had not been an idle threat.  By stroke number three i was not just groaning, but screaming (in vain of course) for mercy and for it to stop.  i am sure that on completion there must have been a tear in my eyes as She again pulled my hair to force me to look at Her.  If i had expected any sympathy, i was sorely disappointed.  i was released from the bondage across the whipping bench and ordered onto my knees.  My hands were once more secured behind my back, and then the gag was removed.   Once free to speak again, i was ordered to thank Her for my fully deserved punishment, and even worse, made to beg that i receive further punishments later.

Advising me that She needed to prepare for my next ordeal, She once again pulled the mac hood over my face and tied it off, telling me that it would help me to practice for the period of hooding that was to follow.

For the next five minutes or so, i was aware of Her moving things around and that some music was started.  Whilst the mac hood restricted my breathing, it was not total, and i was still able to breathe relatively normally. It did, however, remind me that once She used one of the PVC hoods as She had threatened, it would be a different matter, and that restriction of my breathing would be almost complete.   Breath play had been one of the things that we had done during previous sessions, though always on a mild scale.  i had a feeling that today was going to take things to a whole new level.

After a while, the hood was lowered, and Mistress Helen was once again stood in front of me.  In Her hand was a black PVC hood, one with an elasticated neck and with a zip over the mouth, but one nonetheless that that would allow no chance of allowing me to obtain any fresh air once in place.  As with all the hoods that Lady Jane had packed, this hood had been used by Mistress Helen in previous sessions, and was one of Her favourites.  Not only did it not allow me to breath, but it was also thick PVC and meant that it also acted as a blindfold.

Without anything being said, She pulled the hood over my head, informing me that as a start, it would remain in place for 40 seconds.  Since i had previously managed confinement for periods well over a minute, this did not worry me unduly, and i managed to last for the 40 seconds without any real problem.  After a very short break with the neck lifted to allow me to breathe through my mouth, but still covering my eyes, the hood was once more lowered, with the instruction that this time it would be 50 seconds.  Again this was managed, and so too were two further hoodings of one minute, and one minute ten seconds, although by the time i had received the last of these, i was definitely feeling the effects, and was glad that the hood was then removed.

Still left kneeling on the dungeon floor, Mistress Helen stated that it was time to experiment with some electrics – something which i really did not enjoy at all.  Whilst She released my hands from behind my back, and proceeded to set up Her electrics equipment, i was ordered to strip off completely and resume my kneeling position.

Once She had everything ready, She produced from the case a purple PVC mac which i was ordered to put on, this time the correct way around.  Next She secured me to the St Andrews cross with my back against the wall.  She produced a collar which was fastened around my neck, and then a penis gag which was stuffed into my mouth and secured in place.  Instead of then starting to use the electrics, She produced a red PVC hood and pulled that over my head.  Whilst so trapped, i was aware that the front of the mac was being undone, and nipple clamps were snapped shut on my nipples, forcing me to yell into the gag.  The mac was arranged to ensure that the front of my body was exposed, and i then heard the buzz as the electrics were switched on before the hood was removed.

As soon as the hood was off and i was able once more to see, She was stood there holding the feared Violet wand.  Although i was shaking my head frantically to indicate that i did not want it, Mistress casually informed me that what i wanted was of no interest, and since i was here because Lady Jane wanted me to be punished, i was going to get a nice session being tortured regardless.  And that is exactly what happened.  For the next 10 minutes at least my nipples, balls and most other areas of my body were subjected to a variety of the Violet wands attachments, the experience only becoming worse as i started to sweat.  The end, however, was only achieved because Mistress Helen offered me the chance to stop the electrics if i agreed instead to suffer CBT and NT instead – which i foolishly (albeit willingly) agreed to by nodding my head furiously.

Stating that it may yet prove to be a mistake, She switched of the electrics and, picking out the key to my CB6000 from the envelope, removed my chastity device – all the better She said, to make me suffer.  And boy, was She not joking…

The nipple clamps were removed, only to be replaced by another set connected by a metal chain.  As if that were not bad enough, She proceeded to hang weights from the chain, further stretching my already sore nipples.  Satisfied that i was suffering enough from this, She switched her attention to my exposed cock and balls.  A series of slaps and twists were then followed by Her tying cord first around my scrotum, and then my cock, ensuring that it was suitably tight and painful.  Next, weights were added to the cord hanging from my balls and my scrotum was stretched until i was forced to yell into my gag.  Satisfied for a moment that i was suitably in pain, She produced a tube of deep heat and proceeded to coat my balls and nipples.  As the ointment gradually started to work, and my groans became obvious, my predicament was made worse still as She set the weights swinging side to side.  Still not satisfied, i watched in horror as She selected a flogger from one of the hooks on the wall, and started to lash me across the stomach and thighs, my attempts to escape its attention only causing the weights to swing of their own accord, further adding to my suffering.

Finally this particular torture came to an end, and weights and cords were removed.  It did not, however, signal the end of my CBT, as She selected a small penis whip and proceed to spend a further 5 minutes flogging my cock and balls.

Once finished, She left me still strapped to the cross whilst She went to get herself a drink before eventually releasing me and removing the gag, ordering me once more to my knees.  As She sipped Her water, She asked if i would like a drink.  When I replied that i would, She said that She would make sure i got a drink soon.

Changing the music on the CD player, Mistress Helen then sat down in Her chair and stated that She would like to see me dance for Her and instructed me to dance as befitted a sissy for Her amusement.  Not being in any shape way or form any use at dancing, it was not long at all before She was laughing at my efforts, whilst insisting that i try and do better.  After a few minutes, She said that that it was noticeable that my excuse for a cock was bouncing around in a manner unbecoming of a sissy, and that i had to replace my chastity devise, which i was made to do stood in front of Her before being made once again to dance.

Eventually i was allowed to stop and was ordered to kneel at Her feet and worship Her shoes, making sure to lick every inch until they shone.  i was kept at this for at least five minutes before being told to fetch the pink PVC mac, put it back on back to front and return to kneel before Her.  Once done, my hands were once more cuffed behind my back, and the mac hood pulled over my face and tied at the back.

It was time, i was informed, for me to once again assume the role of sissy maid, but this time She informed me that i was to be made up to look like the slut i obviously was.

i knelt there once again whilst i could hear Mistress Helen climb the stairs and return after just a couple of minutes.

On Her return, the mac hood was lowered and i could see that there was laid out on the table next to her chair a make-up bag.

During the next five minutes i was made-up with eye shadow, eye liner, rouge and lipstick to make me look like a slut, before She produced from the case a pink wig which Lady Jane had obviously acquired from somewhere, but which i had not seen before. With the mac removed and my hands again un-cuffed, i was instructed to dress in my maids dress and underwear, including pink fishnet hold ups and my heels.  When satisfied, Mistress Helen walked me over to a mirror to look at myself.  The effect of the whole ‘make-over’ was to make me look slightly ridiculous.

After being humiliated by being made to speak in a high pitched voice and repeat several times that “i am just a cheap sissy slut who deserves to be treated as a worthless fuck-toy”, Mistress Helen stated that i should have no doubt that before the afternoon was out, She would make sure that that was exactly what was going to happen.

Before that, i was told, i would need to be subjected to further humiliation and PVC aversion therapy.  i was once again made to put on the pink mac and then to refit cuffs to my ankles and wrists and to kneel with my back to the metal post.  My wrists were then secured behind my back around the post, before my ankles were similarly cuffed together either side of the post.  A piece of rope was then produced which linked my wrist and ankle cuffs, forcing me into an uncomfortable position, leaning forward held to the post just by the wrist cuffs.  This was soon remedied by a leather strap tied around my chest pulling me back up against the post, and resulting in my being placed in a stress position.

Advising me that it was time once again for some aversion treatment, She produced the zipped black hood and pulled it over my head.  There followed several bouts of breath control, each longer than the previous one, until at one stage i begged for escape.  Leaving me an addition 10 seconds, by which time i was almost at the point of passing out, the hood was then removed.  If i believed that was going to be the end of it, i was, of course, to be disappointed!  Moving across once more to the case, Mistress Helen returned carrying a small plastic bag.

The contents She told me, were a pair of Lady Jane’s soiled panties.  In the letter it transpired that Lady Jane had told Mistress Helen that part of my punishment at home – after i had long ago been caught by Her masturbating over a pair of Her dirty panties – was to be gagged with dirty panties, sometimes with a second pair; crutch over my nose and pulled over my head whilst being made to kneel as Her footstool, or knelt in the corner.

With no further explanation, the hood was once more pulled over my head, and the previous hooding repeated, until such time as i was forced to beg to be allowed air.  This time, rather than having the hood removed, the zip was undone and the soiled panties crammed into my mouth before the zip was closed again.  With a warning that i was under no circumstances to spit out the panties, i was going to be subjected to 2 full minutes inside the hood before it was going to be removed.  Despite the warning, i was soon struggling and moving the panties aside enough, managed to beg for release before the hood was removed.

Although the hood was removed, it was clear that i had, if not actually spat out the panties, managed to eject enough to speak, and thus disobeyed Mistress’s instruction.  The immediate effect was to receive a slap across both sides of my face.  To my horror, the panties were forced back into my mouth before a ball gag was then forced on top and secured in place.

As if that were not enough, Mistress then said that for such an act of disobedience, the two minute hooding was to be repeated not once, but twice, and that an additional twenty strokes would be added to my final punishment.  Now totally unable to do anything at all to prevent it, the hood was pulled back over my head.  By the end of the first two minute confinement, i all but passed out. And with only a few seconds to take a breath, the hood was on again.  This time i must actually have passed out because i remember coming to with the hood off, and the gag and panties removed.

What i saw as i came around was Mistress Helen stood in front of me holding her strap-on harness fitted with a large purple dildo.  As i looked on in horror, She proceed to remove Her skirt, and put on the harness.  Once it was on, She stood with it inches in front of my face, and removed my gag.

As i knelt there helpless and suffering from cramp in my legs and arms, i was made to repeat over and over, progressively louder and louder that “i am a worthless slut who wants to suck my Mistresses cock and to be fucked like the slut i was until She was done with me”  Despite my humiliation, i had no choice but to do as i was told.  She then produced a condom and placed it over the head of her ‘cock’ ordering me to roll it down using just my mouth.  As soon as this was done, i was further made to beg to be allowed to suck Her cock before being subjected to having it thrust over and over into my mouth, causing me to gag on several occasions until there was a time when it was possible for me to take it all in my mouth without gagging.

Even then, worse was to come.  After being released from my position secured to the pole, the mac was removed and i was ordered back over the whipping bench and secured as before.  Again, my sissy panties were lowered and my sissy pussy exposed.  Standing in front of me once again, Mistress Helen informed me that it was time that She finally got to peg me and to use me like the slut i had become.  Thrusting Her cock once more into my mouth – informing me to make it good and wet before it was to be rammed up my sissy pussy – i was instructed on how to beg to have Her fuck me long and hard.  The humiliation of being made to suck Her cock, followed by having to beg Her to violate my arse for the first time was more than i could ever have imagined.

What i had not bargained for was how much it was going to hurt, and how much more humiliating it was to get as i was made to repeat that i was now Her bitch and that i deserved to have my sissy pussy fucked whenever She wanted.

Finally, the ordeal was over, and i was left strapped down whilst the verbal humiliation continued.  I was then made to watch as Mistress Helen stood in front of me to remove Her strap-on, informing me that I was going to receive many more such pegging’s, not just from Her but from Lady Jane in the future as well.

And then, to add insult to injury, Mistress Helen proceeded to again collect the soiled panties and ball gag and fit them to me once more.  i then watched as She also selected a vicious looking single tail whip from the rack on the wall, and informed me that i was to receive 12 strokes for failing to thank Her for my pegging.  The first 6 were to be administered as i was, but for the second 6, as well as the gag, i was going to be hooded with the red PVC hood as well.

If the strap and cane had seemed bad, the whip took my pain to a whole new level.  The first stroke caused me to gasp.  By the third i was yelling uselessly into the gag for mercy, and by the sixth, i was crying.

During the brief lull whilst She picked up the red PVC hood, i was just about able through my tears to see the smile on Mistress Helen’s face as She pulled on the hood, informing me that She just loved to see a slave reduced to tears, as well as being able to watch the look of fear in their eyes.  She also went on to add that far from deterring her from continuing the punishment, it just made Her want to carry on even more.  And that was exactly what She did, flaying my already sore and stripped arse with the final six strokes, before removing the hood.

Leaving me gagged and bound, She informed me that She was going to leave me there for a while to recover some composure before moving on with my “training”.

As i lay there, the pain gradually subsiding, and with the tears drying on my face, the reality of my situation started to become clear:  the session had seen me humiliated, pegged, and punished, and exactly what still lay ahead of me was unknown.  All i did know was that i was still due for more punishment, and whatever my “training” involved.

After a few more minutes, during which time all manner of thoughts ran around my mind, Mistress Helen returned and proceeded to release me from the whipping bench and instructed me to pull up my sissy panties and kneel once more.  As i did so, i noticed that Mistress Helen was sat once more in her chair, and had changed to now wear a pair of black PVC trousers and knee length shiny black high heeled boots.  Ordered to move closer, She removed the gag and the panties, and made me thank Her for taking my sissy anal cherry, and giving me some of the punishment i so richly deserved.

Instructing me to get down and worship Her boots, i listened in horror as Mistress Helen proceeded to tell me how She and Lady Jane had exchanged emails over a period of a month or so, and how between them they had gradually devised a plan of how to further my descent into submission and service to Lady Jane.  The outcome of these exchanges was that there was going to be a major change in my lifestyle.  A training regime, along with continued PVC aversion was to be put into place, and i was to formally become Lady Jane’s slave, with frequent punishment and humiliation sessions at the hands of Mistress Helen.  Being taken by a strap-on was to become a regular part of my lifestyle, and so too was my becoming a toilet slave.  This last comment caused me to look up, ceasing my boot worship.

Apart from further slaps to my face for stopping, Mistress Helen laughed as She made it clear that as a sissy slut slave, i ought to be honoured that my Wife was willing to grant me the privilege of drinking Her golden champagne.  Somehow, it did not strike me as being that much of an honour, as my previous experimentation with watersports was far from enjoyable.

Mistress Helen then told me that as a special treat, i was going to receive some training today and She was going to allow me to receive Her golden nectar.

After continuing my boot worship for a further five minutes, i was ordered to lay out the purple PVC mac on the floor in front of the whipping bench, and to lie down on it on my back and with my head by the bench.

Once i had done as instructed, my ankles where cuffed together and tied to the post by a length of rope, and my wrists were cuffed above my head to the legs of the whipping bench.  It dawned on me very quickly that there was no way i was going to move anywhere.

Satisfied that i was where She wanted me, Mistress Helen calmly informed me that since She had promised me a drink earlier, i would soon be allowed to drink Her pee, but that first it was time for some more PVC aversion therapy.  She explained that since i enjoyed being face-sat, i was to have my wish; only that for now it was going to be underneath Her PVC clad bottom, and was going to be a brutal affair with no chance to breathe.  Before then though, She informed me that a little bottom worship was in order, and as She lowered Herself slowly over my face, ordered me to kiss Her beautiful PVC Clad bum as if my very life depended upon it – after all, She said, it very well just might shortly!

Keeping me at this task – one that it was fair to say i actually enjoyed, She sat Her full weight down onto my face and i was at once deprived of air.  For a full minute She sat there motionless by which time i was trying (in vain) to escape.  Easing Herself up for a few seconds to allow me a brief chance for air, the process was repeated several times.  By the time She finally rose, i was once more light headed and close to passing out.

As things gradually came back into focus once more, i saw Mistress Helen standing over me holding the red PVC hood.  Pulling this on over my head, but only over my eyes as a blindfold, She told me that it was time for my drink, but that of course, that She needed to remove her trousers, and that as a mere slave i could not be permitted see her pussy, only to accept its offering, hence the blindfold.

As I lay there, i could hear the trousers being removed, and imagined the sight that was denied me.  i was also aware of Her presence lowering down once again, and readied myself to receive Her offering.  To my surprise, however, She told me that as a special treat, She had decided that before being allowed my drink, She would allow me the chance to have her pussy on my face.  i could hardly believe what i was hearing, but felt  and even smelt, her pussy brushing my lips, only to be removed at once.  Almost at the same time i heard Her laugh as She pulled the hood down fully over my face and resumed Her position with Her pussy over my face, although now covered by the PVC hood.  i was greeted by more laughter as She mocked me by stating that i had to be mad if i thought for even a second that there was any chance at all of any direct contact of Her pussy with my mouth, except when the two were to be separated with a layer of PVC in between them.  i was then forced to endure the humiliation of having Her grind Herself over my pvc covered mouth as She laughed and mocked me.

Having tired of the game, the hood was again raised to cover just my eyes, and it was time, i was told, for my special drink.  To my surprise, i felt a funnel being pushed into my mouth and i was instructed to close my mouth and grip it tight.  Whilst telling me that the funnel was to make sure that i did not waste a single drop, She dropped a further bombshell that Lady Jane had told Her that She had ordered a special toilet box for me at home so that my training could continue, and that it was even my Wife’s intention that in time i could be used and even loaned out as a toilet slave, locked into the toilet box for hours for use by anyone who so wished!

i had almost no time to consider the horror of this, as Mistress Helen began to pee into the funnel in my mouth.  With no choice but to swallow, i was threatened that every drop had to consumed, and that any that spilt would need to be licked up, and, since Lady Jane had demanded it, would add 20 lashes to my final punishment, and that the punishment could be delivered without the use of a safe word. Mistress also took great delight in adding that Lady Jane had insisted in Her note that should i fail in any way and require that no safe word were allowed, my final punishment should consist of a minimum of 50 lashes with a variety of punishment instruments of Mistress Helen’s choosing, but – since the cane was Mistress’s favourite, 20 of the strokes would require to be with the most painful cane available.

As the flow continued, i did my very best to take it all, but at one point spluttered slightly before finally draining the last drop from the funnel.

With the funnel removed, my wrists and ankles were released, and i was ordered to my knees.  After a short delay – which i discovered was to allow Mistress Helen to put on a pair of black PVC hotpants, the hood was removed.

i was made to thank Mistress for the gift of Her golden champagne, and to my horror was then shown several drops which sat on the PVC mac.  Mistress Helen made it very clear what that meant, and i was ordered to lick the mac clean and dry.

Once satisfied, i was made to crawl across the dungeon to kneel in the centre below a set of cuffs suspended from the ceiling.  I was ordered to again strip naked, and the cuffs were lowered, and one was fastened to each of my wrists and then raised pulling my hands over my head, still in a kneeling position.  i was then made to watch in trepidation as Mistress selected 8 different punishment instruments and laid then on the floor in front of me.

Standing in front of me, Mistress Helen calmly informed me that all that remained now was my final punishment.  Failure to appreciate my pegging, as well as spilling valuable pee meant that the clause of no safe word and a minimum of 50 strokes was to be part of the sentence.  Add to that the 20 lashes for spilling pee, and a further 20 for my initial errors in dress on arrival, it added up to 90 strokes.  Since that was not a round number, She added, She was going to make it an even 100.

As She had selected 2 canes, it seemed sensible to give 20 with each of those, which left 60 strokes,  Pointing out that She had selected 8 instruments in total, that worked out nicely as 10 strokes with each of the remaining instruments – a cat-of-nine, the leather strap, a riding crop, the single tailed whip, a dressage whip and a wooden paddle.  As She mentioned each of these six, it was picked up and i was made to kiss each one in turn.  Finally the two canes were offered for me to kiss.

Once this was done, i was instructed to stand, and a metal spreader bar was attached to my ankles, before the cuffs on my wrists were raised up and secured such that i was forced to stand on tip-toes.

As i stood there helpless and dreading what was to come, i watched as Mistress Helen went over to the small table and produced once again the soiled panties, ball gag, and finally a pair of red leather elbow length gloves.  Placing the panties and gag on the floor She proceeded to slowly pull on the gloves, telling me that She always liked to wear Her ‘Punishment Gloves’ for a special occasion, and that this was going to be a very special occasion indeed.

Picking up the wooden paddle, i was instructed to beg Her to carry out my punishment.  As if that were not humiliating enough, i was made to answer questions as to why i was being punished, if i deserved to be punished, and if i thought that the sentence for my punishment was fair.  i was also made to again recite that i was a worthless sissy slut, and that i needed and deserved the training and punishment that She was kind enough to give me.

Once satisfied with my verbal humiliation, She explained once again that Lady Jane had insisted on no safe word.  She also stated that the entire sentence would be carried out no matter how much i as going to plead for it to stop and beg for mercy, and that there was no doubt that i would surely be reduced to both in very short order!  It was made clear that i would be reduced to tears, would cry and scream, plead for Her to stop and probably even resort to swearing and name calling.  With a warning that swearing or name calling would almost certainly earn additional punishment, She added that She would enjoy reducing me to such a state, and would revel in my misery.  She did though, state that after the first 60 strokes, and before the final 40 strokes of the cane, i would be gagged with the panties and ball gag, as by that stage, and thereafter my screams would be really loud and now longer necessary.

And then She moved to stand behind and to one side to begin the punishment.

After the first 10 strokes with the paddle i was starting to think that it was not going to be too bad, and then came the dressage whip.  The first three were almost bearable, but from then onwards the pain became too much and i did indeed start to cry and beg,  The cat was next, and only resulted in more cries and screams.  By the time the first 60 strokes had been completed, and as the single tail fell to the floor in front of me, i was a complete wreck, crying uncontrollably and begging for mercy and begging to do anything to have it stop.

The only response from Mistress Helen was a laugh as She proceeded to stuff the now wet panties into my mouth and secure then firmly in place with the ball gag.  As an added humiliation, She said that She thought some more PVC aversion therapy might be in order, the red PVC hood was again pulled over my head and over my eyes and nose.

And then the caning started.  As expected, it was by far the worst pain so far, and i twisted and turned in vain to try and escape the excruciating blows that rained down on my back, thighs and bottom.  i made no attempt to try and count the strokes, trying simply to endure the pain.  When the blows stopped, i was relieved, but this was to be short lived.  i was aware of Mistress Helen standing in front of me again, tapping my chest with the tip of the cane.  Instead of the punishment being complete, She informed me that there were 10 strokes remaining, and as a special ‘treat’ She would make sure that these were delivered with maximum effect.  And as a further touch, and since i still needed to be made to associate PVC with fear rather than pleasure, the final ten would also be administered with the PVC hood fully on my head.

As the hood was indeed lowered, the final 10 strokes were delivered with maximum venom before the hood was pulled clear of my head for what was the final time.

i was left there swinging for a couple of minutes as Mistress Helen stood in front of me, slowly removing the gloves with a huge smile on Her face, but saying nothing.

Finally – again without saying a word – She lowered me to the floor and removed all my cuffs and the collar before eventually speaking to order me to lie back down on the purple mac, face down.  After a couple of minutes, She started to slowly rub a cooling soothing lotion over my back, bum and thighs.  i was then left there to recover for around five minutes.

When Mistress Helen returned, i was given a glass of water, but only after She had spat into it, and told to drink.  i was then informed that the session was over, and that i was to get dressed as i had arrived, and that i was free to go, but that the make-up had to remain until i returned back home and Lady Jane had confirmed i had done as i had been told.

Once dressed, i was told to repack the case and make sure that i had everything with me.  Finally all packed and ready, i was instructed to kneel and pay final worship to Her boots before being released.

As we arrived back upstairs once more, Mistress Helen gave me a hug, and said that it was very clear that my life was never going to be the same.  She reminded me also of what She had said at my very first session “be careful what you wish for”, and added that Lady Jane had asked Her to remind me “that whatever happened today, or in the future, never to forget that it was him that actually begged Me to dominate him and take him as My slave, and that whatever happens from hereon in, he would only have himself to blame”

As a final remark before i left, Mistress Helen told me that Lady Jane had made it very clear, that today was to be the first of many such punishments, and that i had better get used to it!

And so i left, sore, still wearing my sluts make-up (although it was well ruined by this point!) wondering how i was going to manage the drive back home with my back and bottom still on fire!

 

 

 

 

16Oct 2015

Mistress Helen Ryder greeted G otherwise known as “sissy Sandra” “come in she beckoned and just to confirm you know exactly why you are here!  SS smiled nervously and replied “Yes Mistress, I’m a satin panty sniffer & sissy slut and I am here for aversion therapy and to be punished””

Mistress & sissy sat side by side on the sofa, ss was trembling and shaking as she confessed to all the underwear drawers she had been rifling through and not just sniffing them but masturbating into them and leaving them all wet and sticky.  This had all started in her younger years living at home with Mother “Filthy little panty sniffer aren’t you sissy Sandra, and wanking that tiny little sissy clit”  Shaking her head and showing her dismay Mistress Helen stood up and instructed ss to attend the punishment room, where she would be given some special aversion therapy.

“Remove all of your clothing slut and you are to wear these” pointing at a pile of feminine items.

Sissy Sandra started dressing with Mistress’s help, rolling each of the luxurious lace top stockings onto ss’s legs and attach them to a frilly frothy Agent Provocateur suspender belt and then sliding up a pair of panties over the top.  “easy access for that slut hole of yours a little later” Mistress Helen smiled mischievously as she spoke.

SS was instructed to sit on the edge of the bed whilst she was fully feminised in full heavy and very slutty make-up.  Lots of strong eye shadow, heaps of eye liner and mascara, then blusher and finally glossy red giant cock sucking lips.

Mistress Helen selected a wig and placed it on ss’s head brushing and teasing out curls and then fixing a little black bow to match the slutty satin short nightie “There that’s better, what a transformation slut, you can now look in the mirror”

SS could not believe her eyes “OMG I look just like my Mother” Mistress Helen laughed and said “Well that serves you right for sneaking into her underwear drawer and wearing her French knickers”

“Come here SS & get over my knee it’s time you were spanked”

SS was wriggling and squirming as each satin spank was felt against her bottom, her little clitty starting to stiffen and leave a sticky damp patch in her panties.  Mistress Helen spanking her bottom over and over until SS could feel a rosy glow.

“Get on the bed and lie on your stomach, time to hogtie you as the Damsel in Distress and take some photos of you looking like a slut”

Mistress Helen was snapping away taking photos and laughing at ss being so helpless “Wow I’m working up quite a sweat, time to change my outfit” Mistress Helen removed her satin pussy bow blouse and placed it over ss’s head so that she could see Mistress stripping off, only know Mistress was peeling off her clothing just inches away and selecting another outfit.

SS was in heaven and exclaimed so under the satin over her

“Oh Mistress I’m in heaven”

“This is aversion therapy SS, I think you are enjoying this a bit too much”

“I think it’s time to get that little sissy hole all wet and juicy and some pussy hole training for you little slut” Sissy Sandra felt a lubed up gloved finger easing into her and then a little vibrating toy inserted.  It felt rather good!

Mistress Helen picked up a paddle and started bring it down on each of ss’s buttocks in turn until they were nice and redder than before.  Adjustments were made on the ropes and SS was tied tighter into the hog tie before Mistress Helen walked around the front and removed the satin blouse of SS’s face and showed her the new outfit, a 1950’s style swing dress with frothy net petticoats underneath and a strap-on cock hidden away under the layers.

“Time to start using those cock sucking lips, open wide and show me how you suck cock”  In fact roll this condom onto my cock like  prozzie, the condom was pushed a little way into sluts mouth.

Sissy Sandra meekly complied with rolling the condom on and sucking and slurping on Mistress’s veiny real looking cock, secretly wishing she would soon be impaled upon it and used like the true slut that was emerging, but that’s another story……….

(photos always taken with express approval)

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28Sep 2015

I was bent over dusting busily away in Madams bedroom and thinking that I had a very busy day ahead of and thank god that pervert handyman has left me alone for a while!  I was suddenly aware of breath on the back of my neck and oh heck guess who!

“Hello Helen, having a fine morning I see dusting away & bending over showing off those lovely legs of yours”

“Huh, you shouldn’t be looking!  What are you doing in madams room, haven’t you any of your own work to be getting on with?”

“I’m only being friendly Helen”

“A bit too friendly for my liking with perving up my skirts when I’m bending down and trying to brush past me rubbing yourself over me as you do, you’re just a pervert!”

“Now now Helen I think you need to do as your told, you’ve got me into trouble enough times with that bitch and if you don’t do as I say I’m going to get you into trouble”

The handy man raised his voice “Get over against that wall and hands on your head”

I had heard madam’s car coming back on the drive and thought yes play long as hopefully madam would overhear whatever was going on and I wondered what the perv had in mind.

I gasped as I felt my maids uniform being pulled up at the back and my panties (small silky black pair) and my stockings and suspender belt were all on show, then suddenly whack down came the handy mans hand on my bottom spanking me again and again.

“Take that you little trouble maker, telling tales on me and running to madam every 5 mins just because I’m being friendly”  “Anyway all you are good for is a lowly housemaid, women’s work & women belong in the kitchen”

I scoffed at that remark and it was the wrong thing to do as he spanked me more and more!

“I got caned the other day because of you and then had my night ruined because that bitch put me in chastity!  She ruined my evening as I had a date and knew I would be getting into her knickers”

I laughed and then received another wallop “No way!  Madam wouldn’t do that”

“Oh yes she does all the time, it’s alright for you, you haven’t been working here long and she seems to like you Helen.  Jane the Cane they call her”

Just as I was being spanked some more Madam appeared in the doorway (haha that old goat would be in a lot of trouble now) I thought with madam seeing me pressed up against the wall and my knickers all exposed and I’m sure she saw the last spanking.

“What’s going on here?”

The handyman started spluttering pathetic excuses for why he was spanking me and I spoke up “madam he has been calling you a right bitch and complaining about me running to you and telling tales and he said all I’m good for is housework”

“So you think being a housemaid is a lowly position, you best come downstairs and you too Helen”

I wondered what madam was going to do and followed her down to the parlour

“How would you like the day off Helen and have the handyman do all your chores and serve tea and cake to us both?”

Wow I couldn’t believe it and thought haha serves that old goat for being such a pervert and trying to put me down.  “I would love that madam”

“Right better had you dress the part, c’mon get those clothes off”

He stripped off looking down rather ashamed and embarrassed and I relished in his uncomfortable predicament and had a big smile on my face, especially when I saw he was wearing a chastity device on his little cock.  Haha I wasn’t in any real danger then from what I could see and obviously madam kept a very tight rein on him (what an unusual household and not like my previous employers) I could see working here could me a real eye opener.

Madam produced a maid’s outfit with stockings, a girdle that was crotchless, frilly panties and little pinny and hat and even a wig and asked me to help dress the handyman.  She then gave me some nipple clamps and told me to pin them onto PP’s niplles over the dress. I had the giggles at first but then felt very powerful and superior watching him squirm and his humiliation of being turned into a maid.

Madam then linked up chains to ankle and wrist cuffs and stuffed a pair of panties in his mouth with some sort of head harness to hold it in place.  I couldn’t stop laughing and poked my tongue out when madam wasn’t looking and whispering “haha just look at you now Mr pervert”

Madam instructed PP to get down on the floor and polish her very shiny skirt, madam always dressed in very sexy clothing like corsets and leather too, no Laura Ashley like my last household!

“Now stay on your knees and kneel up facing me” Madam had a sign and camera in her hand.

Madam stuffed the sign in his hands and it read: Pansy Penny frilly panted pervert please punish me severely.  She told me to stand next to him and to call him Pansy Penny for the rest of the day and that the photos were to ensure he didn’t try to put a complaint in about his employment so madam would have them to blackmail him with for the future.

“Get over here and bend over” Madam had a cane in her hand and she started caning PP’s bottom and I couldn’t help but grin.  “Watch me closely Helen as it’s your turn next, want to get your own back on your spanking earlier”

“Hell yes I do madam” I was given the cane and I started hitting PP’s bottom ignoring the cries of pain and laughing as I did it.

Madam looked at the clock and announced it was afternoon tea time and that PP should do my tea errands and not forget to curtsey.

PP did a half curtsey in my direction and madam made him do it again I laughed and poked my tongue out doing a proper curtsey back and taking the mickey.

“Go and sit down Helen and put your feet up”

Well I didn’t need to be told that twice, laying back on madams comfy sofa and flashing my stockings at PP poking my tongue out again.  “PP hissed just you wait you little bitch it will be pay back at some point”

“What did you mutter” asked madam

“PP called you a bitch madam” Madam pulled him by the chains into the kitchen and fastened a tea tray with two slices of fresh cream Victoria sponge (the very cake that the handyman was going to take around to his new fancy piece later) haha that spoilt those plans!

“I’m just popping upstairs Helen so keep an eye on Pansy Penny and make sure she makes tea to your liking”

“Yes madam”

PP carried on making the tea and I thought to myself right time to get him/her into more trouble!

“I liked what you did earlier, that spanking made me a bit horny, want to do it again?”

I bent over the kitchen sink and raised my satin uniform and even pulled my panties up some more so my bottom was exposed.  Well PP was over like a flash and started spanking me again and I was encouraging more spanking with telling PP to spank me more in the middle right over both cheeks.

Madam walked back into the kitchen “I leave you alone for a few minutes and this happens, what’s going on?”

“As soon as you went upstairs PP pushed me against the sink and lifted my dress up madam and said I need punishing for getting him into trouble”

“Pansy Penny you are to continue making tea and afterwards it’s time for the cane, Helen go and sit down and have your tea and cake with me”

Mmmm I bit into the slice of cake looking right at PP with a cheeky glint in my eye as I suggestively licked the cream off my fingers and lips and drank my tea.

After we had finished and PP had to curtsy lots and made to stand in the corner whilst madam and I were chatting about my new role working for her household (I don’t think I could be happier elsewhere) she said if PP was muttering that I had to count them and that would be how many he would get……….well I might have miscounted and made a few up!   Madam  announced it was time to cane PP.

I had to choose two different canes and to pose with them so that PP could be blackmailed by me to do anything I asked of him in the future!  But I couldn’t believe it that when madam told me to crush his head between my thighs whilst she caned him he only started trying to feel my legs up.

“The dirty pervert is feeling my legs up”

Madam made PP get up and go to the kitchen, she stood a full to the brim glass of water on the tea tray. “If you spill one single drop then we start from the very beginning”

Madam caned PP and then it was my turn, I was a tad disappointed that Pansy Penny hadn’t spilt any water and had received all the 70 strokes of the cane.

“A lesson learnt I think and time to go and do Helens chores off you go” PP was dismissed giving me a withering stare as he/she departed.  Rubbing a very sore welted red bottom.

What would tomorrow bring in this unusual household I thought to myself as I skipped off to go and have a nosey around madams potting shed, I had heard some strange noises coming from there the other day and wondered what might be inside……………………….

 

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