Cross Dressing

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)

DSC_0083

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……………………….

 

2015-09-24 10.33.25

2015-09-24 10.40.22

 

 

 

 

 

 

 

 

2015-09-24 10.47.22

2015-09-24 10.40.33

  • 1
  • 2