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My Sissy journey
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By *rhuges OP Man 6 weeks ago
Cardiff |
I had always been into the sud dom world mistress sub ect, but not the sissy maid world.
Well it all started about a year ago.
I had been chatting on line to a mistress in her late 30s, I was early 40s.
After answering questions as to what I was looking for she set up a meeting in a pub.
She was looking for a sub to do the house work ect, but their uniform would be stockings and panties to enforce to the sub that he was not worthy of being called a man.
The evening of the meeting came .I arrived at the pud 10 minutes early and found a secluded corner to sit. I ordered a for myself.
Well the meeting time came and went ,it was now 20 minutes over and she hadn't showed up or texted.
I thought I'd give it a round half hour before I left.
Just as I was about to leave I heard my phone bleep. It was Mistress Lisa.
The pub seems busy come out side and meet me in my car, a white Range rover vogue.
I immediately got out of my seat and racing into the carpark
I found the Range Rover and opened the passenger door. Get in says the woman.
She was a larger lady with all the curves in the right places. She was wearing a long black mac ,she had long brown hair with hinds of red in it. Here face was immaculately made up as were her hands with long red nails .
Pull down your pants she commands . I pull them down to reveal my white frillys and black stockings .
She puts her hand inside my panties and feels my already hard cock. Well she says that little cocklete needs locking away doesn't it.
Yes mistress I say meakly.
We discuss her needs and I try to convince her that I am the person for the job. Right Jack she says ,it you want me to train you ,you will be known as Jackie, is that an issue?
No Mistress I've just never really experienced Sissy subs.
Right she says be at my house next Friday at 6pm . Don't be late |
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By *rhuges OP Man 6 weeks ago
Cardiff |
So the following Friday I turned up on time. Stripped off so I was only wearing panties and stockings . I was given meanial duties to perform like dusting and cleaning.
If I missed anything or didn't do the job to the standard she required I had to pull my panties down and go over her knee for a sound spanking. Several times I started to sod, her response was ,spare the rod spoil the sissy.
This had been going on for Five or six weeks, so when I turned up and Mistress Lisa said I have a surprise for you jackie I was a bit taken back. She produced a PVC maids outfit. I will need you to wear this tonight Jackie we have a guest coming.
I had no choice but to put on the maids out fit, dispite my reservations a out being a sissy it did feel nice and it did give me a hard erection.
Mistress jade is coming to visit.
I did my normal duties ,I was just finishing up when the dor bell rang. Go answer the door Jackie Lisa ordered.
I opened the door. A petite blond woman was standing there. Hare make up was immaculate as were her long red nails. She was wearing a full length shiny plastic mac.
Come in I say it was only then that I noticed she had a leash in her hand
On the other end was a fully blown sissy. Big frilly dress immaculate make up and a pink wig.
They followed me into the lounge Mistress Lisa greets Jade and offers her a chair, whose your new sissy? Mistress Lisa asks. Oh this is keekee say hello keekee. Hellow mistress Lisa keekee says in a high feminine voice.
Then Jade says I was a little taken aback when your sissy didn't kirtsy to me she says.Is this true Jackie ? Mistress Jade asks. Yes mistress I say I forgot I was so nervous, it will not happen again. And what do we do to make sure things don't happen again Jackie?
I reluctantly pull down my panties I fall across Mistress Lisa's lap. Wack wack wack 10 had spanks, I squeal. WA k wack wack another ten hard spanks.
I felt so humiliated being spanked with an audience.
Do you think that was appropriate? mistress Jade Lisa asks. I think that since she disrespected me I need to punish her as well.
Ok that makes sense, Jackie get over mistress Jades knee now.
I walked over and bent over her knee.
Keekee can you get my paddle out of the bag.keekee pulled out a wooden paddle from her carpet bag and handed it to jade. Keekee blow me a kiss and smiled as I felt the first stroke I yelled in pain ,after another five my legs were kicking and I tried to put my hand up to protect my poor backside. Put that hand down this instant you naughty girl shouted Mistress jade wack wack wack another 10 strokes, I was now crying. Stand up girl! Mistress jade commanded Now show me your kirtsy, I kirtsyed wack another had stroke of the panel again! She said this time lower!! I do it again Wack!! I was fully crying now.
Keekee show this girl how it's done. Keekee gets up and does a graceful Kirsty ,I try to copy. Needs work but will do for now I suppose, now go get yourself cleaned up, you look a mess! |
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By *rhuges OP Man 6 weeks ago
Cardiff |
I disappeared to the bathroom my poor bottom still throbbing in pain.
I tidied myself up and come back into the lounge and knelt beside Mistress Lisa.
Feeling better? She asked Yes mistress I said.
Right you're in for a treat now my girl. Mistress Jade has offered to give you a complete make over to be a proper sissy , you lucky girl.
I wasn't sure I wanted this but decided to smile and say thank you mistress.
Keekee was told to fetch the makeup kit from her car.
Keekee returned with a huge bag. I followed her to the bathroom.
Strip she commands . Now, you stupid girl!!
I stripped and showered she shaved off any stray hairs , pulled my foreskin back to make sure it was clean , cleaned my arse out, had me put some pink stockings and frilly pink panties .She than had me sit down and started applying makeup , I wasn't sure I wanted this, and said as much to keekee. If we don't do this we'll both get a hard spanking now shut up and let me do my work.
She did the lot false lashes rouge, lipstick earnings and finally a pink wig like hers,and a frilly pink sissy dress.
Right that's the best I can do!
She led me back into the lounge the two Mistresses were chatting. Wow said Mistress Lisa, aren't you a pretty girl , thank you mistress I say.
Keekee whispers something to mistress Jade.
So way isn't this slut in chastity Lisa? She asks.
I've been meaning to do it she laughs.
Jade beckons me over ,she roots in her back and pulled out a pink plastic chastity cage. Lift your dress she commands. I lift my dress terrified she may punish me again. She pulled down my panties hold my cock and fits the cage. She then wipes her hand with wet wipes
She hands Lisa the key.
Right girls we have another surprise for you both . We are hosting some guests in a little while to show you two off. I hope you will not disgrace yourselves. |
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By *rhuges OP Man 6 weeks ago
Cardiff |
An hour later the door bell rang. Get the door Jackie Says Mistress Lisa. I open the door there is a large gentleman dressing in a tux and a large women in a long flowing black dress .She was in her late fifty's immaculate make up and immaculate nails. I kertsy and invite them in. They come into the lounge and say Lisa lovely to see you just come straight from the opera.
This is Jackie and the other is keekee.
They will do anything you ask watch this. Girls show Lady Sophie your Chastity cages.
We both stand in from if her lift up our dresses and pull down our panties.
She laughed ,can we see who is the smallest she says.
Our chastity cages are removed Girls sand facing each other and give each other a kiss says Lisa. Keekee pecks me on the lips. No!! Girls tongues commands Jade. Sir John(they guy in the tux ) was laughing, like two lesbian school girls he laughs.
Keekee put her tongue in my move I put mine in hers.
I had always thought of myself as straight, not sure if it was the humiliation or the taste of keekee's tongue but my cocklette was completely hard |
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By *rhuges OP Man 6 weeks ago
Cardiff |
Lisa laughs keekee your cockette isn't had yet. Jackie get down on your knees and get her cock hard
.I hesitated, I'd never sucked a cock before . Now!! Demands Lisa.
I go down on my knees and start stroking keekee's cock. No you stupid girl laughs Jade use your mouth.
I slowly put keekee's cock in my mouth and can feel it grow.
I find I'm actually enjoying the experience or I would if I wasn't so humiliated.
After several minutes keekees cick is rock hard. We both stand in front of Lady Sophie with are dress pulled up and our cocklettes standing to attention. She takes the cotton tape measure and multiplys the girth x length.
Oh she laughs Jackie definitely wins this one .
For some reason I felt proud.
So which one would you like to bid for Lady Sophie Lisa asked .
She has a whisperer conversation with Sir John. He writes something on a peace of paper and hands it to Lisa. She laughs I couldn't possibly rent her how for that she laughs and writes down another figure.
How about this says Lady Sophie We offer the smaller amount but if see please us both we will add a bonus payment.
That's acceptable says Lisa.
She then looks at me. Jackie you should be very proud of yourself , this is your first rental, now don't let me down and I will expect a very nice bonus from Lady Sophie.
It then occured to me that this mature couple had been bartering a sum of money to rent me out
Now I'll expect her back tomorrow, but injury free welds and bruises are allowed but too many and you'll have to pay damages as I will not be able to rent her out until they fade
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By *rhuges OP Man 6 weeks ago
Cardiff |
Lisa attached a collared around and my neck and gave the leash to Lady Sophie.
Sir John heaved himself up and said lets go Sophie.
Sir John and lady Sophie disappeared through the door , Sophie pulls my leash come on slut she say I hope you're going to be a good girl
I was both very scared and very excited at the same time .
I followed them to a black Range Rover. Sir John got in the driving seat.
Open the rear door for Lady Sophie commands Sir John.
I open the rear door and she got in shuffled to the over side and pulled me in by my leash .
She says to Sir John I should have used gloves when I measured their cocks John, my finger feel all sticky from pre cum .
She looks at me and points one of her well manicured fingers at me. Suck my finger clean sissy she commands. She puts the first finger in my mouth and I such on it.
When her fingers had rings on them she took them off and had me suck them before having me dry and polish them with a lint cloth |
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By *rhuges OP Man 6 weeks ago
Cardiff |
We drove for sometime before we slowed down . Sir John presses a button on this dash and gates open. We drive in ,the gates shut behind use.
Sir John gets out, I get out and open the over door for Lady Sophie.
Sir John opens the front door and goes in.
There are two stair cases winding up to a landing. Sir John says I'm going to get a whiskey darling, meet you up stairs.
Lady Sophie leads me up the stairs past several rooms ,then enters one. It has a huge round bed in the middle ,with chairs scattered around.
She hooks my leash over the Cornor of the bed . Heal she says. I kneel and she disappears into the ensuit.
Ten minutes later she reappears wearing only her high heels stockings and panties. Here large breasts swaying.
Just then Sir John enters, very nice my dear he says ,and embraced her in a passionate kiss. He pulls off his pants ,I had to look twice his cock was enormous.
Lady Sophie sees me looking ,yrs she says ,that's a real man's cock.
Now go over and place sit John.
I crawl over ,his cock is only semi hard. I lick the end then kiss his cock down to his balls I massage his balls with my hand before putting his cock in my mouth. I gag immediately, Lady Sophie laughs. My eyes are watering and I have saliva dripping from my move.
Lady Sophie lays on the bed on her back Sir John comes to the front of her, her legs go over his shoulders and I have to guide his cock into her wet engaged pussy |
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By *rhuges OP Man 6 weeks ago
Cardiff |
Sir John starts fucking her. Sissy calls Lady Sophie suckle on my nipple. I climb on the bed and put my mouth around and her large engorged nipple and start sucking and flicking with my tongue. I swap between her to large breasts.
She moans as Sir John pounds her, this is what a real man can do sissy she moans to me.
She starts to shake and moan clenches her large white thighs are and sir Johns neck.
Sir John moans as he empties his load into Sophie's cunt .
Sissy your on cleaning duty sir Jonn commands.
First I get of the bed crawl around and start to clean Sir Johns cock. I squeeze the end to push out any cum and lick it all up.
I then go between Sophie's legs, I can see cum dripping out. I lick her clean then have to clean the floor to lick up her cum juice. |
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So damn hot. What a lucky sissy indeed |
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Keep going It’s dream come true |
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So hot! I would totally love to be in that position x |
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By *rhuges OP Man 6 weeks ago
Cardiff |
Lady Sophie gets off the bed and disappears into the ensuit. She reappears 10 mins later with a sexy black strap on attached to her.
Sir John sits on the bed and as me on all fours in front of him.
I believe they call this a spit roast my dear he smiles as he puts his large cock in my mouth.
I feel cold lube being rubbed into me arse, then feel the strapon slowly enter me I wince, I can squeak as Sir John has my head in his hand ,moving it up and down his cock. I'm gagging my eyes are watering and I have saliva dripping out of my mouth.
Lady Sophie now picks up the rhythm, fuck me bark darling she commands, I start moving my arse in rhythm with her.
Lady Sophie reaches down and starts walking me. I am soo turned on at this point |
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By *rhuges OP Man 6 weeks ago
Cardiff |
I came in seconds, and that my dear is why your a sissy not a real man laughs Lady Sophie. She has me lick up all my cum from her hands. Jackie says sir John keep going you haven't finished with me yet .
Sophie then says Jackie you get the champign from the fridge and I'll finish off Jonny.
I jumped of the bed and when to the fridge in the room. Sophie starts to suck jonny's cock.
I pop the cork take out three flutes and pour the champagne.
I put three glasses on a silver tray and bring them over. Sophie takes one and then dribbles sit johns cum into it from her mouth, then mixes it with her finger . She hands me the glass . Sir John and Sophie take the other two.
Grab that saucer will you dear says mistress Sophie. I bring over the saucer, she takes my flute and pours the champagne mixed with cum on yo the saucer.
She than takes off two of her rings and drops them into the saucer. On all fours Jackie chop chop. I go on to all fours and start licking up the champagne. Sir John and Lady Sophie are kissing between taking sips of champagne. |
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By *rhuges OP Man 6 weeks ago
Cardiff |
Oh she says the rings had cum on, so clean those after she says.
I drank the champagne and clean her rings, then help each ring in my mouth so Lady Sophie pushed her finger into my mouth fitting her ring on.
You have down so will sweeties she says I think I'll reward you with a kiss.
I so wanted to snog her I lift my head up she bends down and kisses my forehead.
Wait she laughs did you think I was going to kiss you on the lips ??? No Lady Sophie I lied.
I think she did laughs Sir John.
Can you imagine she laughs , I think you may be forgetting your place young lady, and you know what we do to sissy's who forget their places don't you?? |
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By *rhuges OP Man 6 weeks ago
Cardiff |
Come on Sweeties says Lady Sophie over my lap. She is sitting on the edge of the bed.
I crawl over her lap. She grips my hard cock with her large white thighs .
Wack wack wack wack wack she strikes my bottom I squeak like a sissy. Oh I do love to hear them squeak laughs Sir John.
Wack wack wack . You need to understand your place you naughty sissy girl lady Sophie's scolds.Youbare here for our entertainment not your own. I'm sorry mistress I squeal it will not happen again.
My tears are starting to well up in my eyes She stops fetch my hair brush from the ensuite Jackie she says in a stern voice. Now! She commands. I get off her lap and start to walk toward the ensuit. On all fours sir John says.
I go on all fours and crawl into the vach room
I'll expect the brush to be held in your mouth I hear Lady Sophie shout.
I crawl back holding the brush in my mouth. Lady Sophie takes it from me and points to her knee.
I really crawl over her lap again. Wack wack wack wack wack.
I am now crying , please Lady Sophie, I promise to be a good girl please forgive me.
After 10 strokes with the hair brush I'm crying.
She turns me over and pulls my head toward her erect nipple. I suck egerly as she rubs my stinging bottom. There there she says you know it's what you need don't you |
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By *rhuges OP Man 6 weeks ago
Cardiff |
Now go to the bathroom and get cleaned up.
When I come out if the Bathroom Sir John is already asleep Lady Sophie is sitting up in bed yet large breasts exposed. She taps the space next to her. I jump in and lean my head on her very amble breasts.
The next think I remember is waking up. Both are gone. I hear someone in the en suite.Lady Sophia come out dressing a very nice designer dress , Sir John is off golfing I have to take you back to Mistress Lisa, so have a quick shower and meet me down stairs.
I had a shower cleaned myself up, still in all my sissy clothes I walked down the stairs and into the kitchen.
She gives me a coffee then ushers me out of the house and into the passenger seat of her black jag.
As we are driving back she says to me Did you enjoy yourself last night Jackie?
You cannot imagine how much I said.
Well she says I have a proposal to put to you.. .. |
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By *rhuges OP Man 5 weeks ago
Cardiff |
We have been keen to employ a maid for sometime, but because we'd want a live in it would somewhat stunt our type of play.
We had never thought of a Sissy maid until we had a chat with your Mistress.
So would you consider a full time maids position?
I was a bit shocked, well I said generally only do this on weekends , I do have a normal full time job Lady Sophie.
I have discussed this with Sir John and we would be willing to pay you a salary of 25k plus free quarters and food plus holidays at least twice a year either in our property in the South of France or in Whistler sky resort in Canada.
Sir John would help you rent out your property as well.
I was very very tempted as I hated my job.
What a out mistress Lisa? I asked.
I can come to an arrangement with her young lady. Don't let that put you off .
Before I could stop myself I said I'd love to accept Lady Sophie
Good choice said Lady Sophie Sir John will be placed.
We were driving cross country along quiet B roads .
Right she says to start with you will call me Mistress Sophie from now on. Yes Mistress I said.
As she is driving she hoists her dress up with one hand , I think you need to please me now slut she says .I undo my safety belt a d bend over. Her white soft fleshy thighs really turn me on. My head disappears between them .My tongue is darting in and out of her shaved wet fanny. I feel her pushing my head and squeezing her thigh around it.
I use my fingers as well as my tongue. Lady Sophie pulls over into a layby just before she moans and soaked my head .
I come up and adjust myself using the vanity mirror.
Right she says don't say anything to Mistress Lisa today. I will speak with her tomorrow.
With that she pulls up out side Mistress Lisa's house. I thank Sophie, she extends her hand for me to kiss, which I do.
Mistress Lisa comes to the door
I was wondering were you were Jackie she says.
How did it go. It went very well mistress I said.
Good she said then I'll expect a nice bonus from them .
No come in and get changed
One of Mistress Lisa's rule was she never wanted to see me dressed as a boy.Myboy clothes were in a room at the front of the house. I changed into them and left to drive home |
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By *rhuges OP Man 5 weeks ago
Cardiff |
I didn't hear from anyone for several days. Wednesday evening I got home, there was an A4 envelope waiting for me. I opened it and it was the contract for the maids position .
There was a 3 months probation but in that time they would pay my mortgage, after that Sir John would arrange a suitable person to move in .
I signed it and sent it back straight away.
I also received a text the same evening from Mistress Lisa.
She told me that Lady Sophie had told her about the job offer and had received and had offered compensation . She hoped it worked out ,but if it didn't give her a call.
I gave a months notice at work.
The month went really slowly until my last Friday came.
I had a text from Lady Sophie, tell me to report to the that evening at 6pm .
I was told to ensure I was dressed appropriately.
By this time I had quite a few sissy lingerie and dresses.
I dressed in pink stockings, pink high heels pink frilly panties and bra and pink and blue frilly dress.
It was winter so by 5 it was dark. I locked my house you put my suit cases in the car and set off for my greatest adventure. |
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By *rhuges OP Man 5 weeks ago
Cardiff |
I didn't hear anything for about a week. I came down from work one day and there was an A4 envelope waiting for me.
I opened it up and it was the contract. I read each page, they would provide lodgings and food for me with a 25K salary.
There was a 3 month probation period . In that time my mortgage would be paid. After which Sir John would organize a lodger .
There was a letter from Lady Sophie, she said she had been in touch with Mistress Lisa and agreed a compensation package which would be paid to her on satisfactory completion of my probation.
I was to arrive on a Friday evening fully made up and in my pink frilly dress and panties.
Friday Eve eventually arrive. I bathed cleaned and shaved all my hair. Took me an hour or so to get ready and eventually put on the pink wig.
I drove there and pressed a button on the other gates. They opened automatically, I parked around the back. I had been told never to use the front entrance unless specifically told to. I parked the car and rang the bell at the back Sophie opened it I curtseyed .
I have an unexpected guest in the drawing room Jackie. Can you please bring up prosecco and cakes in 5 mins. I curtsey again and say Yes mistress Sophie |
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By *rhuges OP Man 5 weeks ago
Cardiff |
I wheel the trolley up to the door and knock. Come says Mistress Sophie. I enter the room and push the trolley to were Mistress Sophie is talking to a young slim girl early 20s at most .
I pour the prosecco into two glasses and give one to Sophie and one to the young lady.
She looks at me and starts laughing, what the fuck is that she laughs. I can feel myself going red. She is our new maid Sophie says. No is it male? she asks. It's a Sissy explains Sophie, well has it got all its parts? She asks.
Jacki show my niece Laney your parts.
I am so humiliated a girl less than half my age. Now! Jackie Sophie says.
I pull down my panties and lift up my dress revealing a very small soft cock . Omg it's small Laney laughs Where is your chastity device your lady asks Sophie. It's in my bag mistress I didn't have time to put it on. Go fetch it this instant you naughty girl. I curtsy virtually crying with embarrassment I leave the room |
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By *rhuges OP Man 5 weeks ago
Cardiff |
I come back with the plastic pink cage and hand it to Sophia.
Lady Sophie has me pull down my panties and lift my skirt once more. She holds my balls with one hand and starts to put it in the cage.
Partly humiliated and embarrassed and hugely turned on the warmth of Lady Sophie 's hands caused my cock to start to grow. She slaps my cock hard, and there will be no of that nonsense young lady she said crossly ,I squeal my cock shrinks and the cage is fitted and locked into place.
Do you ever punish her Aunty asked Laney. Oh yes she knows what happens if she's a naughty girl Laney. Let me show you.
She points to her knee. I'm sorry mistress it will not happen again I sniffle. She points again . I slide over her lap and pull my skirt up.i feel her rub my bottom then wack wack wack wack wack ,5 hard slaps.Laney squeals with glee. Do you always use your hand ?Aunty she asks. No says Sophie we had a paddle as well .oh oh can I see that please she asks.I don't see why not. Jackie go get the paddle,Laney then says Aunt can we call her Jennifer instead I don't like Jackie.
I'm sure we can do that Laney can't we Jennifer. Yes mistress I say, now run get me the paddle Jennifer.
I go out of the run and into another were there is a large cupboard with all the equipment .
I return with the paddle curtsey and hand it to mistress.
Can you give me a demonstration Aunty asks Laney. Of course my dear. Jennifer and she points to her knee |
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By *rhuges OP Man 5 weeks ago
Cardiff |
Now ! Jennifer, now don't show off in company. I lay around Lady Sophie's lap. I feel the paddle smooth my arse. Then Wack wack wack you see Laney it's all in the wrist action.Can you do that again Aunty Laney asks Wack wack wack wack, I'm squealing now but the pair of them are completely ignoring me.
Can I have a go ?ask Laney of course say Lady Sophie. Jennifer get up and get over miss Laney's knee. I get up and shuffle over to Laney and get over her knee. I was over twice the age of this young girl but she had all the power over me. I was so ashamed.
Wack wack wack wack. Very good dear, you're natural.
Wack wack wack wack. Ooh I like this ,I'm now sobbing. Can I punish her the next time? Aunty
No Laney say Lady Sophia ,but you can certainly watch.
Jennifer you may now go clean yourself up.
I pull my panties up and with my arse still stinging go get cleaned up.
As I leave Lady Sophie says to me Jennifer if I'm not here you will listen to Miss Laney as if she were me. Do you understand . Yes Mistress Sophie I say |
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By *rhuges OP Man 5 weeks ago
Cardiff |
I rest on my bed for an hour. The bell goes for the lounge.
I get up and make my way down.
I knock on the door. Enter a voice says. I come in and curtsey. Sir John is sitting in an arm chair opposite Miss Laney and Lady Sophie . A malt for me and a G&T for the girls Jennifer he says. Right away sir I say curtsey and rush out of the room.
I make the drinks and return.
I hand them out, then Sir John says to me ,it's come to my attention that the ladies were a bit harsh with you this afternoon Jennifer. Yes sir I say. And Lady Sophie put the cage on without milking you first. Is that right?
Yes sir I say.
Lady Sophie says yes that was wrong of me so to make a mense would you like to be milked now Jennifer?
Oh yes Mistress I say that would be wonderful.
But who's to do it ?laughs Laney.
Then Laney says let's but all our names in a hat and let Jennifer pick one.
Lady Sophie laughs ,such a good idea.
They right names on four bits of paper and have me pick one at random.
Who have you picked Jennifer ?asks Sir John |
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By *rhuges OP Man 5 weeks ago
Cardiff |
I unwrap the paper and look at it. Myself I say glumly. Right says Lady Sophia, let's get you ready.
She unzips my dress and I wiggle out of it. She pulls down my panties and unlocks the cage to release my cock.
So I'm standing in the middle of the room wearing high heels stockings and a bra. Lady Sophie Sir John and miss Laney are all watching me. You may begine orders Lady Sophie
I feel so very humiliated and yet my cock is getting hard.
I touch it and slowly start wanking it.
My face feels bright red, as I slowly play with myself in front of an audience.
It doesn't take long until I put my hand up and say may I cum Mistress Sophie. Shall we let's hear Sophia asks the over two
Laney then says can I have her cum for me Aunty please please.Sophie laughs, ok Laney just this once. I'm ordered over to miss Laney. I feel her warm hand touch my cock and I cum over it. On your knees and lick my hand clean you dirty little slut shouts Miss Laney.
I go on my knees and clean and suck the cum off her hands and fingers |
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By *rhuges OP Man 5 weeks ago
Cardiff |
Right said Sophie ,Sir John and I are going to the cinema room are you joining us Laney. No she says I'm off out.
Jennifer says Lady Sophie, clean yourself up, then come back and clean the room please.
Yes mistress I say.
I clean myself up then come back and clean the room up. I pick up the piece of of paper with the names on that chose who milked be.I just happened to open one of the pieces of paper, it had my name on, opened another it also had my name on. The bitch I thought Laney put my name on all the pieces of paper.
Once I'd finished I I knocked on the cinema room door. Enter came a voice. I come in and curtsey . You Sir are madam need anything else this evening I asked.
On says Ladie Sophie you may go to bed. Please make breakfast for 7 tomorrow morning. Yes Mistress I say. I'm about to leave the room when Lady Sophie says is there anything wrong you seem a bit stressed. I couldn't help Myself , It's Miss Laney I say. Oh what has she done asked sir John. It's just that when she but the names in the hat as to who was going to milk me she put my name on all the pieces. Did she now says Sir John. That seems a little unfair, I shall have a word with her. Thank you sir I say , and head for my room |
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By *rhuges OP Man 5 weeks ago
Cardiff |
The next day I had breakfast ready for Sit John and Lady Sophie when they came down the stairs. Eggs on toast with hot coffee. After breakfast they said we are off to golf now Jennifer miss Laney is out so you have the house to yourself.
If you finish your chores you are welcome to use the cinema room .
I did all my chores within 3 hours. I made myself a coffee and when into the cinema room. Chose a movie and started watching it, Eating popcorn. About 20 minutes into the film I hear the door open, oh I thought they re back early. It was Miss Laney. How dare you she said how fucking dare you.
Come here now!!!! I jumped out of my seat and stuttered I was given permission Miss Laney I promise.
As I get up to her she brings her hand down and slaps me hard. I all over. How dare you complain about me you silly girl she shouts, Sir John rang me and told me!!!.
I'm sorry Miss Laney I say. Oh sorry will not cut it young lady come this way and marches out of the room.
This girl was half my age half my weight and yet had the power to do anything she wanted to be. I could feel my cock straining at its cage |
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By *rhuges OP Man 5 weeks ago
Cardiff |
She walks into the punishment room and opens up a cupboard .She pulls out a red ball gag . Kneel she orders. I knew. Open ,I open my mouth and the ball gag fitted a fixed in place. Right she says this will stop you snitching .
She then has me bend over a horse ( like a volting horse)
She finds a cane and swishes it.
Right she says 10 strokes for punishment. 1 2 3, I scream in pain , saliva running down my chin as my screams are held in my the gag, 4 5 6 . My legs are kicking , keep those leg still slut she says 7 8 9 10.
She puts the cane down. My arse is stinging like hell. I then feel her start inserting something into my arse. It going inside me and I'd held on place by a belt are and the waist. Now stand up. I stand up. I then feel immense pain in my arse and fall to the ground. Laney shows me a key fob. When zi press this button it will shock your arse young lady. Now go stand in the corner. I stand facing the wall. Don't you dare move until I get back Jennifer she says and disappears out of the door |
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By *rhuges OP Man 5 weeks ago
Cardiff |
It felt I had been there for hours but probably less than 2.
The door opens and I clench ready for the shock.What is going good n here I hear Lady Sophie say .I turn around, what the hell has happened to you Jennifer she says with concern in her voice. She removed the gag. What happened? She asked . I'd rather not say I say I undo the belt round my waist and pull out the butt plug. She sees my marked arse. Omg this was Laney wasn't it she say angerly. Id really rather not say I niff. You go get yourself a hot bath Jennifer.
I was in the bath for about an hour. When I came down I heard voices in the lounge. I walked in and there was Laney arguing with Lady Sophie.
Right she said I really have had enough of you. She grabs her and puts her over her lap.
Laney sees me. You snitches again!! She says angerly. No she did not says Lady Sophie.
Jennifer you may watch this.
She pulls up Laney's white tennis skirt to reveal her lovely peach shaped bum . My mother will not be happy with his she shouts. Your mother sold Lady Sophie has told me to discipline you in anyway I see fit young lady she scoulds |
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Mm...good to see Lady Sophie looking after her sissy. I hope she gives the little brat a good hiding. She obviously doesn’t understand the dynamics of the Mistress/Sissy scenario |
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By *rhuges OP Man 5 weeks ago
Cardiff |
Wack wack wack wack wack How dare you treat my maid that this Wack wack wack wack you will apologize to Jennifer now!!.
No I will not cries Laney. Go fetch me the paddle Jennifer say to me. You would not dare cries Laney. Wack wack wack wack.
I give mistress Sophie the paddle . Wack wack wack wack. Ok ok cries Lanie I'm sorry Jennifer she cries. For what asks Mistress Sophie. I'm so sorry for punishing you Jennifer I had no right, I'm sorry she cries.
Do you except her apology Jennifer? Yes I say. She lets Laney off her knee. Now go to your room young lady she says sternly.
She then adjusts her dress and brings out one of her large breasts. She points to her lap.
I lay down and start suckling on her tit . . I feel her removing my cage, and she slowly starts milking me. I was in heaven |
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By *rhuges OP Man 5 weeks ago
Cardiff |
After I have cleaned Mistress Sophie's hand and lick all my cum up, the cage is put back on and I'm sent to bed.
The next morning I've prepared breakfast as normal. Mistress Sophie and Sir John come down for breakfast, Think you Jennifer says Sophie, Miss Laney has gone away for a while she says.
After breakfast . Mistress Sophie say right I'm out for the morning so carry on with you duties Jennifer.
About half way through the morning I'm summoned to Sir Johns office. I knock on the door, enter he says.
He his behind one of those large antique desks with green leather on top. He is talking on the phone. He point to the floor. I bend down and can see his trousers are down. I crawl under the table and see his large cock switching. I hear him say , yes we need to make that act law ,we need to rally the Lords. I take his cock in my mouth and feel it grow |
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Omg omg I didn’t once again reach the end  |
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By *rhuges OP Man 5 weeks ago
Cardiff |
I can hear him on the phone, the power he has really turns me on. I like and kiss his balls then like a long the stem.
I inserted it into my move as I hear him say, we hill have to bring this up in the house it's just not damn well good enough.
His cock is too big to take it all ,I do my best and gag.
I can feels his cock tension before he shoots his load into my mouth. I clean his cock for him , then slide out from beneath the table. He butss his hand on the reciever and says that will be all Jennifer. I curtsey and leave his study. |
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This is perfect, thank you xxxxx |
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By *rhuges OP Man 5 weeks ago
Cardiff |
I spend the rest of the afternoon cleaning and ironing.
I'd just folded the last piece of clothing when Mistress Sophie comes in. I've just inspected the lounge Jennifer and I've found dust! I am sorry mistress I say ,I'll go do it again.
What do we do with girls that don't meet Mistress Sophie's high standards Jennifer, they get punished mistress. Yes they get punished. Meet me in the punishment room in 5 minutes please. Yes mistress I say glumly.
She bends me over and has me lift up my dress. She pulls down my panties and says oh dear there are still marks from your encounter with miss Laney. Now what to do...... |
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By *rhuges OP Man 5 weeks ago
Cardiff |
Follow me she says. I follow Mistress Sophie into her study. She turns on her PC. She beckons me over and points at her side I kneel at her side. She is looking at an excel spreadsheet. She says I've read that the optimum time to milk a sissy is every 5 days any longer and they don't concentrate on their duties. Well I'm going to add another 2 days . You were due to be milked in 3 days , it is now 5 days. She changes the date in her spreadsheet and all the dates up to the end of the year change by two days. Every time you do not come up to my standards an extra two days will be added. Do you understand me Jennifer?. Yes Mistress Thank you.
She is wearing red high heels black stockings red pleated skirt and white blouse.
She hoists up her skirt, you're making me feel horny Jennifer she says kiss my stocking tops.
I Kiss her stocking top then her large soft white thighs.
She opens her legs I smell her scent from her moist clean pussy.
Lick it girl she moans. My tongue enters her ,she pushes my head deeper into her thighs .my cock is hurting as it force against its cage. Mistress Sophie leans back on her chair ,her large white arse comes into view luck my arse she moans. I plant my head as far into her arse as I can. My tongue enters her arse hole, it tastes so sweet. She is moaning and shaking until I feel her orgasm over me. She pants in her chair. Slowly gets up and says well done Jennifer , tidy yourself up and tidy up my study please ,there's a good girl |
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By *rhuges OP Man 5 weeks ago
Cardiff |
I cleaned up the study with my cock straining at my cage. I realized that being a sissy meant you had to have a lot of self control, I just tried to think of other things. The rest of the day went without incidence.
The next morning I was up preparing breakfast.
Lady Sophie and Sir John came into the kitchen a out an hour later to be served breakfast. After which O supplied sir John with an ironed copy of the financial times.
He looks over his paper and says you do realise you're 3 months probationary period I'd up today don't you Jennifer.
I said I hadn't the time had gone so quickly. Report to the lounge at 9am please he says.
Had I fail it? Were they going to send me home. I hoped not.
At 9 I knocked on the lounge door , come came a voice. I entered and curtseyed to Sit John and Lady Sophia who were sitting in two arms chairs.
So said Lady Sophie how do you think you have done. Well mistress I say ,it was a huge transition tofor me to move in and become a permanent sissy. I guess I could have done better. I then go down on my knees please please take me on.
They both laugh of course we will you have done a sterling job laughs sir John. There is one thing though says Lady Sophie. Sir John would like to fuck you, but due to his large appendage ,he fears he may hurt you so we would like to start stretching your sissy clit for a few months before he tries. How do you feel about that.
So Sir John was an over weight aristocrat ,but the power he had over people and especially me was a huge turn on and the thought of him wanting to fuck me was a huge turn on .
I certainly have no objections to that Mistress I say. Good days sir John be a sweety go on all fours with your arse facing us.
I do this hand lift up my skirt. ISir John puts lube on one of his fingers and inserts it inside me, then 2 then 3 and slowly starts finger fucking me
My cock is now almost unbearable as it strains against the cage, at last he stops ,then fully inserts a small butt plug, we will leave this in and changed it for a bigger one in a few days time .
Well if your happy Jennifer we are happy to make this role permanent |
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By (user no longer on site) 5 weeks ago
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Yay! Three cheers for Jennifer xxx |
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By *rhuges OP Man 5 weeks ago
Cardiff |
I was so happy, I never thought I'd make the transition from part time sissy to full time. I had come such a long way.
I awoke the next morning and realized it was milking day. I made Sir John and Lady Sophie breakfast as usual , nothing was said, they both went out to golf and I was told to complete my cleaning duties as normal. No mention of milking , I was so frustrated. I needed to cum so badly.
They came back mid afternoon, and ordered G &Ts. I brought their drinks in on a silver tray. Curtseyed and gave them their drinks. That is all said Lady Sophie. I felt so frustrated but tried not to show it as I walked out. Wait To Lady Sophie says. Isnt it milking day today Jennifer?
Yes Mistress it is I beamed.
They were both on the big sofa talking about their stocks and shares. Lady Sophie takes the key from around her neck , has me stand by her and unlocks the device. She then slowly massages my cock while in deep conversation with Sir John.
It takes about 10 seconds before I spurt warm cum all over her hands.
She removes her rings and then has me lick all the cum off her hand . She then stops the conversation with Sir John has me open my mouth and puts her ring in .no suck these clean ,then get a lint cloth to polish them Jennifer. I suck on her rings , before taking them out of my mouth and polishing them .I then put the rings back on lady Sophie's gorgeously manicured hands .
Lady Sophie then licks my cock back up |
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By *rhuges OP Man 5 weeks ago
Cardiff |
On all fours now Jennifer. I go on all fours and lift up my skirt. My panties are pulled down and the butt plug inserted a few days ago was removed ( I had had to remove it a few times for me ablutions so hopefully I'd reinserted it correctly).
The butt plug is slowly removed and a bigger one inserted. I squeal as it's inserted up to the hilt. My panties are pulled back up. Right young lady says Sir John, stand up. I stand up, now take off your wig. I take off my pink wig to show my real hair. Right says Lady Sophie I think it's about time we get rid of that nasty wig and die your real hair. Can you place strip. I take my cloths off. And your lingerie Jennifer says Sophie . I am now naked except for my pink cage. Do a little twirl says sir John. I feel so turn on and humiliated as I twirl completely naked in front of my mistress and master.
I follow mistress to the bath room, where she has me hand my head over the bath and she dies my hair pink. You are now a permanent Sissy she laugh.
My manicurist is coming this afternoon Jennifer I thing we will have some lovely pink nails fitted for you |
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By *rhuges OP Man 5 weeks ago
Cardiff |
Sure enough the manicurest came. I was introduced and long pink nails fitted.
I was really pleased, Lady Sophia had me but all my male clothes in a bin bag and disposed of them.
You are now a permanent Sissy she says with delight.
She then puts bright red lipstick on me I says Sir John loves to see lipstick marks on his cock .
An hour later Sir John arrives home. Mistress has me parade up and down the lounge showing off my new pink hair and long pink nails. I have put nice red lipstick on her Jonny she says.
Oh you spoil me he laughs and sits down in an arm chair. Well Jennifer? Says Mistress Sophie. May I pleasure you say? I ask.
Well since you have made such a big effort Jennifer you may. I unbuttoned his flies and release his cock, which by this point is rock hard. In minutes I have him moaning as I lick and kiss it. You can shallow more than that sweety Lady Sophie says and pushes my head . I gag and my eyes water I feel him stiffen and then feel his warm cum fire into my mouth. I with draw and they both laugh when they see the lipstick marks on his still hard shaft.
Do you think I could try fucking her yet Sophie? he asks I'm so fucking randy
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By *rhuges OP Man 5 weeks ago
Cardiff |
I followed Lady Sophie and sir up the sirs and into the bed room. Lay on your back with you legs in the air I was told. Sir John stands at the bottom and lifts my pink stockinged legs with red high heels over his shoulder. As a treat I thing we can remove this says Sophie pointing to my cock cage. She takes the key from around her neck and removes it my small hard cock shoots out. They both laugh. I hold my dress up and my panties pulled off. He slowly removed the butt plug , I moan as Sophie lubes up this hard cock ,I feel it at the entrance of my clit. He presses slowly as it enters me . He with draws then pushes back in. Each time pushing in a little deeper. Look laughs Sophie her little cocklette is hard. Sir puts his hand around my cock , his signet ring with his family crest on rubbing against my skin.
She slowly starts to fuck me and milking me at the same time I moan with both pain and pleasure .
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By *rhuges OP Man 5 weeks ago
Cardiff |
Sorry Sir John starts to fuck me  |
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What a great story, lucky sissy. |
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What a wonderful story. You area very lucky sissy. |
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By *rhuges OP Man 5 weeks ago
Cardiff |
As he is fucking me with my legs over his shoulders, he starts to milk me. Everytime t ell him I'm near to cuming, he slaps my cock several times, my erection goes down ,he then starts milking me again. About 15 mins in and he has managed to get his large cock all the way in he starts to moan, I am stealing like a school girl as he slowly builds up the rhythm. You are a damned good fuck my girl he moans as he squirts his cum inside me. He with draws and disappears into the en-suit.Lady Sophie replaced him and to my huge surprise she leans over and starts to suck my cock. I was in seventh heaven.
After a few minutes I say mistress I'm about to cum. She continues to suck until I cum in my mistresses mouth. She gets up walks over to me and opens my mouth with her hands. She then dribbles my cum into my mouth ,until it's all gone.
Go get cleaned up now Jennifer then come back and clean up the room.
She then hands me the butt plug, remember to reinsert this sweeties we don't want your clit to go too tight do we. No mistress I say I curtsy ,as I leave the room sit John comes out of the ensuit, slaps my arse and say to Lady Sophie that was a damn good fuck, thank you my dear
Lady Sophia replaces him |
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Mmmmmm Just what I needed tonight  |
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By *rhuges OP Man 4 weeks ago
Cardiff |
The next day I'm now making breakfast when Sit John and Lady Sophie appear.
Lady Sophie immediately says bend down and pull your dress up.
I do as she asks she pulls my panties down ,which reveals the butt plug in place. See she laughs, I told you she would have it inserts. Sir John laughs yep you were right darling. I get back up and serve breakfast and sit Johns financial times.
Jennifer we are having some like minded friends over tonight. Don't be offended but we will need to collar and leash you for the evening. That would be fine Mistress I say.
Throughout the day I complete my chores at about 4 pm I get called into Sir Johns study.
He tell me to bend over his desk. I bend over ,he has me hold my skirt up. He pulls down my panties and plays with the butt plug ,before pulling it out. I feel him lubing my arse.
I feel his large cock at the entrance before it is slowly eased in. I so need to fuck you young lady he breaths.
His cock is slowly pushed inside me. I squeal in my pane and pleasure, my cock is straining at its cage.
He slowly starts to fuck me , moaning and getting deeper each time.
Sophie suddenly appears Oh John she says I thought we'd agreed you wouldn't fuck her until our guest were here. I'm sorry my darling I just had an urge, we I hope you will still be able to perform tonight dear.
They were having this conversation ,with Sir John still fucking me as if I didn't exist, This was a huge turn on for me and I start moaning. |
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By *rhuges OP Man 4 weeks ago
Cardiff |
Sir John laughs don't worry , I will with that I feel his cum explode into me. He withdraws.
Jennifer Lady Sophie's says. Go get cleaned up .I have Laid out the dress you will ware tonight. I pull up my panties still feeling SirJohns cum running out of my arse. Don't forget this says Lady Sophie handing my my butt plug.
I get showered then go into my room.
On the bed are pink high heels with matching pink stockings, a pink basque and a pink sissy dress with lots of petty coats sawn in so it looked really frilly.
It took me about 2 hours to get cleaned up make up and dressed. |
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By *astpoetMan 4 weeks ago
where the world takes me |
What an amazing story  |
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By *rhuges OP Man 4 weeks ago
Cardiff |
I came down stairs and was inspected by Lady Sophie, she checked my stocking seams were straight,all hair removed , make up perfect. I was then told to go to my room and wait.
I look out of my window and see lots of people arriving and a catering truck.
It got to about 9:30pm and I assumed I'd been forgotten about.
Just then the light on the console came on telling me to got to the large dinning room.
I good down the stairs and into the big dinning room
There was a long large table with 12 people on each side. Both men and women, aged probably between 25 and 60.
I see Sir John and Lady Sophie at the far end. They wave me over.
I noticed there is another Sissy standing next to sir.
This is Rachel he says, don't worry she's not replacing you it's just for tonight.
He then explains I am to stand at the far end, Rachel will be at the other. The music will start . We walk along butting out hand on the shoulder of the person we are walking by. When the music stops the shoulder that we are touching is the person we will slide under the table and pleasure.
The music starts I walk down the line of people until the music stOps. I stop at a women in her late 20s with a short black dress on. I see Rachel has stopped by a guy in his 40s
We both go under the table. I used my tongue and fingers on her smooth moist fanny. I can hear her moaning before I get a gush over my face mmmn.
Rachelstill has the guys cock in his mouth. He cums about 2 minutes later.
Right says Sir John Jennifer wins. Rachel is led to a low horse in the middle of the room. She is bend over. The young woman who I had made cum gets up takes the paddle by the horse. Lift up your dress Rachel says. Rachel lifts up her dress. The women pulls down her panties wack wack wack wack wack wack. Five strokes of the paddle.
Shall we do it again asks sir John. There is a unanimous Yes from all the guests |
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By *rhuges OP Man 4 weeks ago
Cardiff |
The music starts again ,this time I get a man in a Tux Rachel gets an older woman. He cock is already out of his trousers, I luck the end and pull his foreskin back ,put the tip in my mouth while massaging his balls. He groans and stiffens ,then shoots his load into my mouth
I turn my head Rachel has her face pushed right in the women's pussy. She xums several minutes later.
Rachel you know the drill laughs Sir John. Rachel walks slowly over to the horse and lifts her skirt. The man in the tux comes over wack wack wack wack wack wack. Rachel's arse is now very red. She looks at me crossly .
Again asks Sir John Yeeees comes the reply. This time the music stops when I'm touching Lady Sophie. I go between her large fat soft thighs ,her stocking tops brushing my face.
I'm picking her pussy ,my fingers go past her pussy and into her arse, she moans . Rachel has a young women as well .
Lady Sophie gushes first.
Put after catching her breath she says that I'm disqualified for fingering her arse.
She says Jennifer to the horse.
I go over to the horse and bend over it .
Lady Sophie comes up Wack wack wack wack wack wack wack wack wack wack wack.
How dare you touch your mistresses arse with out permission Jennifer Wack Wack wack wack wack.I am now crying ,I'm sorry mistress ,I got carried away.
Right says sir John ,we are going to have a small auction, people can bid to fuck Jennifer and Rachel |
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I'd so love this to happen to me!! |
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By *rhuges OP Man 4 weeks ago
Cardiff |
With my arse still stinging, I am kneeling at Lady Sophies feet watching the auction .
A couple in their 40s won me. He was slim good looking in a tuxedo she was slim long black hear, simple black dress with a diamond nose stud.
Sir John asks public or private guys?? The women answers Public, there's a huge cheer from the other guests.
The women Lillian disappears with Lady Sophie While the hight of the hours is adjusted so my head is in line with Tuxedo man's groin.Lillian reappears dress gone, in purple a black panties and bra set with a strap on attachment |
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By *rhuges OP Man 4 weeks ago
Cardiff |
Mr Tuxedo unzips his fly's and flops out his semi hard cock.
I eagerly let him guide it into my mouththe lady pulls down my panties and pulls out the buttplug. My arse hole feels loose and needs filling.
I feel lube being pushed into my arse,before I feel the head of the strap on being pushed into me.
There is a little pain as it's pushed in but turns to pleasure as she starts to fuck me |
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By *rhuges OP Man 4 weeks ago
Cardiff |
I was eagerly sucking Mr Tuxedo 's cock gagging a few times this made the audience cheer , zlHe gets more enthusiastic and starts face fucking me .I can see my lipstick smeared around his cock. Meanwhile The strapon lady was starting to fuck me deep and hard, I was in ecstacy, fuck me make slut I heard her say as I started to move my arse in rhythm to her thrusting.
I'm not sure how long it lasted. Mr Tuxedo pulls his cock out of my mouth and drips it in to a champagne glass. Lady Sophie comes over pours some champagne into the glass and mixes the cum with her finger. The strap on is removed and Lady Sophie quickly reinserts the but plug, we don't want your clit shrinking do we Jennifer she laughs. She then gives my the cum champagne cocktail and watches me drink it. Everyone claps, I was so proud.
Right Jennifer time for you to shower and go to your bed young lady |
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By *rhuges OP Man 4 weeks ago
Cardiff |
I was up early the next day cleaning up the dinning room, mess everywhere.
It took me around 2 hours before everything was cleared. I was just about to start cleaning the floor when Lady Sophie appeared.
You did well last night Jennifer she said, but never ever touch you mistresses arse without permission, do you understand???
I when down on my knees a begged for forgiveness, I'll let it slide on this occasion she said.
You have now been with use 6 months. As a reward to deliberate I was thinking of renegotiating your contract.
Oh I will you be paying me less money.
Well says Lady Sophie we were thinking of putting the money in a trust fund for you as well would like to own you, and you cannot pay something we own.
How would you feel about that? I would love it I say.
Good she said just one more thing, you will have a tattoo as proof of ownership, is that acceptable. Oh yes mistress definitely.
That afternoon Sir John and Lady Sophie had me sign the new contract. She then took me to a tattooist about an hour and a half away.
I had to pull down my panties, he looked a bit surprised to see my pink cage, but I guessed he saw a lot of strange things.
He started tattooing just above my groin. It was very painful.
When I looked at it it say property if Lady Sophie.
Wow I was now owned .
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