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From Jack to Sissy jacki
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By *rhuges OP Man
over a year ago
Cardiff |
It all started last year. I had been on FS for about a year before hand and hadn't managed to get many responses from couples .
I had just about given up ,but enjoyed reading the forums .
One of them caught my eye , a couple were looking for a sissy maid to help out at their 'special parties' no more information than that.
I idly wrote a response explain I did sometimes enjoy dressing up but I wouldn't describe my self as a sissy by any means.
I forgot about the post until about two weeks later when a mail appeared.
I opened it expecting it to be from a male asking if I wanted a blow job. In fact it was from the couple, they said it was refreshing to read a well written honest mail and would very much like to meet me.
I wrote back I said I was both excited and surprised to hear from them and would love to meet them.
We arranged a time and place, about a 45 min journey for me.
They said although I didn't think of myself as a sissy they would expect me to become one. To show my commitment on our first meet I was told to wear a pair of black frilly panties, if I didn't have any I should buy some for the meet.
Asluck would have it I did had a black pair.
The evening of the meet came aI bathed and removed body hair . Wearing my panties under my trousers I set off for the meet.. |
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By (user no longer on site)
over a year ago
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By *rhuges OP Man
over a year ago
Cardiff |
The meet was in a country pub. I parked up and wondering nervously into the pub. I sent a message in FS to say I had arrived.
I got an instant message back saying we can see you. Come to the table at the back of the pub. Bring a G and T and a white wine, plus a glass of water for yourself.
I got the drinks on a try and slowly walked to the back of the pub. On a table in the corner a couple were sitting down chatting to each other. The women looked up. She was in her mind 40s with a blond Bob pink blouse, with rather large breasts and black skirt with a slit were I could see black stockings.
She beckons me over a finger from her well manicured nails.
I come over and place the drinks on the table.
You may sit says the women in a cut English accent.
What do you think asks the man. He was in his 60s smart dark suit with a few extra pounds around his belly.
I'm not too sure yet says the women.
Right she says you will always address use as Mistress and Sir do you understand ,yes mistress I say in a quiet voice.
You will only speak when asked a question, I nod my head .
The man gets you and sits by me.
Undo your trousers he says. I undo them to expose my black panties. Good girl he smiles he puts his hand down inside my panties and feels my cock.
I'd never had a man feel my cock be fore ,but given the situation it started to get hard in his hand |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Cant wait  |
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By *rhuges OP Man
over a year ago
Cardiff |
I think she's please to see me laughs Sir. Good girl says mistress. Now tell us about yourself.
I told them that I'd always felt submissive and recently got into wearing lingerie in private.
Have you any experience asks mistress. I've met a few pro dommes I say but would love to be owned especially by a couple such as your selves.
Well we'll have to see laughs mistress.
They told me they are looking for a sissy made who is willing to go the extra mile to please her mistress and master.
I beg them to give me a chance to prove myself. Sir removes his hand from my panties.
Now get on your knees and kiss my feet demands mistress.
I look around it's a quiet corner but it's on the way to the toilet and you get people passing out table intermittently.
Now! Demands mistress. I look around noone is there. I get off my chair and get down on my knees. .mistress is wearing shinny black kitten heeled shoes. I start to kiss then . I then notice a random block walking past to the toilet and looking at me.
I can feel my face going red with embassement. Carry on demands mistress. I carry on . Don't you dare get up yet demands sir
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By *rhuges OP Man
over a year ago
Cardiff |
You may get up now slut says mistress, what do you say to me?? Thank you mistress I mumble. Sorry zi didn't hear that she laughs, Thank you mistress I say louder. That's better she laughs.
You will be considered. We will let you know in a few days whether you have been successfully ,we have a few more sissys to see.
I left. I didn't hear anything for about 5 days. I assumed I hadn't been successfully, Should I mail them I thought to myself.
I mailed them a very respectful email asking them could they possibly give me some feedback .
Again another two days I could see that they had read the mail but not replied.
I assumed I wouldn't hear from them again, then about a week later I had a mail from Sir.
Sissy it's taken a bit longer to get back to you then we envisaged, but the good news is we think that we could use you. Would you be interested?
I replied straight back and said Most definitely yes sir.
Right he replied , I was given an address and was told to be there at 3pm on the following Saturday. They were holding a party and they needed an extra sissy to serve. If I did well they may think of taking me on. Permanently. Would you like that sissy??
Oh yes please I mailed back. See you at 3 on Saturday.
I was told to bring along all my lingerie so they could decide how I should dress.
I was so excited |
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By (user no longer on site)
over a year ago
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Mmmmmmmmm.  |
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very nice story - looking interesting indeed. |
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By *rhuges OP Man
over a year ago
Cardiff |
Saturday comes I bathe and shave. Put on my black frillies and stockings. Chino s over the top with a blue polo shirt. Pack my lingerie in a bag and set off.
I follow the satnav to a house in its own grounds. By the closed gates is an intercom.
I press the button. I voice says Yes!. Hi I say it's Jack I'm expected. Jack?? Says the voice who are you after??
I realised I didn't know their names just Mistress and Sir.
I met them last week I say. Who did you meet says the voice sounding irritated now.
Had this been a hoax?? Had they sent me to a random House I wondered?
Mistress and Sir I finally said.
There was silence then the voice said Oh you're their new sissy, the gates opened.
I parked my car and walked up to the large front door .
As I approved it opened. Sir was standing there in a smart suit .
Come in he says.
I enter and he shuts the door.
I'm in a large entrance hall.
There are people all around cleaning arranging tables and flowers ect .
Just looked like a normal busy business.
Strip he commands, but sir I protest can't I go somewhere a bit more private.
He raises his hand and gives me a slap around the face.
I stagger backward.
Leave he says now!!
Sorry sir I say please give me another chance. Be this time everyone is looking at me, some are smirking.
Last chance he says strip now!
I unbelt my trousers and let them fall. I remove my polo top
I stand there in just my panties and stockings.
And the panties he demands.
I slip out of my panties and stand in front of him,wearing just my black stockings.
Chair he demands ,one of the helper brings a large chair and sets it down. Sir sits in it and points to his lap.
To my horror I realise I'm going to get a very public spanking |
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By *rhuges OP Man
over a year ago
Cardiff |
I felt so embarrassed , I lied across his lap as instructed. Whack whack whack In future slut never question a command do you understand Whack Whack Whack. Yes sir I cry Whack Whack Whack. I looked around ,everyone was watching some seemed embarrassed for me some were laughing .
I started to kick my legs as my poor arse started to hurt Whack Whack Whack.
Now get up he commands.
He gets up out of the chair follow he says and walks off with me running behind him after picking up my clothes, with a red arse and red eyes.
He enters a room on the ground floor. There is a chair and mirror , boxes of make up and racks of dresses .Jane!! He shouts.
I women in her mind 50s coming into the room.
Here's the new Sissy he explains. Shall I do the usual sir she asks.
Yes thank you Jane ,with that he leaves the room.
I see you have felt Sirs hand on your botty she laughs. Yes I say , it hurt. Oh you got off very lightly she laughs. Now sit on the chair there's a good girl |
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By (user no longer on site)
over a year ago
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By *rhuges OP Man
over a year ago
Cardiff |
Jane was in her 50s a large lady with short black hair. Her make up was impeccable as we're her long pained red nails.
She started by cleaning my face before applying the makeup, false eye lashes and lipstick. She threaded my eye brows and finally fitted a wig.
I noticed her large breasts under her floral dress,her nipples definitely looked erect.
I stood up and she chose the lingerie I would be wearing red panties and stocking with matching red bra.
She noticed me looking at her breasts. You like ? She asked.my cock was already semi hard.
She took hold of my cock with her hand and played with it for a few seconds, it went rock hard. She laughed, she pulled the top of her dress down to reveal a tight black bra. Here breasts were fighting to get out.
She released one, here nipples were the largest I'd ever seen and very erect. Without waiting my mouth was around it ,I was sucking it for all I was worth.
She started to milk me as I sucked.
Unfortunately within 30 seconds Cum shot out of my cock |
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By *rhuges OP Man
over a year ago
Cardiff |
Jane was in her 50s a large lady with short black hair. Her make up was impeccable as we're her long pained red nails.
She started by cleaning my face before applying the makeup, false eye lashes and lipstick. She threaded my eye brows and finally fitted a wig.
I noticed her large breasts under her floral dress,her nipples definitely looked erect.
I stood up and she chose the lingerie I would be wearing red panties and stocking with matching red bra.
She noticed me looking at her breasts. You like ? She asked.my cock was already semi hard.
She took hold of my cock with her hand and played with it for a few seconds, it went rock hard. She laughed, she pulled the top of her dress down to reveal a tight black bra. Here breasts were fighting to get out.
She released one, here nipples were the largest I'd ever seen and very erect. Without waiting my mouth was around it ,I was sucking it for all I was worth.
She started to milk me as I sucked.
Unfortunately within 30 seconds Cum shot out of my cock |
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By (user no longer on site)
over a year ago
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Great start.
Jackie is so lucky. What I’d do to be in her position. |
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By (user no longer on site)
over a year ago
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By *rhuges OP Man
over a year ago
Cardiff |
She laughed, pathetic she says. Right you're milked now She produces a metal chastity device and fits it to my now semi hard cock. She then fits a padlock . Now she says you can ask for it to be removed, in which case you'll be told to leave or keep it on and you will be milked once a week by me if you're a very good girl.
She fits me in a black maids dress , the dress is short enough to show my stocking tops. A black wig and all the make up applied.
She then fits high heel shoes and a black leather collar.
Right she says fitting a leash to my collar, on all fours I get down on all fours and am led out of the room |
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By *rhuges OP Man
over a year ago
Cardiff |
We enter the hall again, people everywhere, Jane walks over to sir pulling on my leash. Sir is giving orders to people in preporation for some sort of event
Stand girl ! He commands I stand up and Jane hands home the leash. You've done another good job sir says to Jane smiling well done.
Sissy give me a twirl . I spine around as sir observes me.
Lift up your skirt he commands I lift it up . He pulls down my panties to reveal my caged cock. He laughs and says look at this sissy's pathetic cock guys.
I mean come up dressed in overalls to have a look. He laughs that's pathetic guys you have to look at this!
I just want the ground to swallow me up a both men and women were now looking and laughing.
Mistress appears, Ralph she say put the sissy down and get on with organising .
Mistress says to me pull up your panties Jacki there is work to be done .
She picks up the leash and leads me away.
She leads me into a room where there are a number of cages on wheels. About the size for a large dog .
Right she says in the cage.
She then explains another sissy will Join me soon. Then a cover will be out over the cages, At a later time the cages will be wheeled out into the main hall for the entertainment of the guests.
I crawl into the cage nearest me. Mistress closes the door locks it and disappears out of the room |
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By *rhuges OP Man
over a year ago
Cardiff |
There is a blanket on the bottom of the cage. .I set down. About 30 minutes later I hear the sound of high heels on the floor.
The blanket is whisked off the cage and the door opened. A younger TV is put into the cage. In her middle to late 20s. She's got an amazing figure with long black hear and amazing eye lashes. She is wearing a white crop top with a short red checked skirt with red panties and red stockings.
This is Tanya says mistress. Tanya this is Jacki. We look at each other both sitting in the cage.
Well says mistress get to know each other. Tanya give Jacki a kiss on the lips.
Tanya kisses me. She had gorgeous red shinny lip stick on.
I kiss her back. Tongues now mistress says.
Sir come in and laughs just like two naughty school girls he laughs.
We start getting more passionate ,ok girls stop. |
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Getting very hot and interesting. A sissy like me can only dream of such things
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Fantastic story! Thanks for sharing x |
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By *rhuges OP Man
over a year ago
Cardiff |
A blanket is then thrown over the cage. We feel the cage now being pushed. He hear a lot of background chatter as the cage stops.
The blanket is pulled off
We hare in a large hall with men and women in smart evening dress.
Mistress is standing my the cage. Some entertainment she shouts .
Get them to suck each other off shouts a young women in a black cocktail dress.
You heard says mistress in a low voice get to it.
We managed to get into a sort of 69 position and start licking each others chastity device.
They've got cages on laughs the womenlets see if they can still cum.
I have Tanya's lovely cock I. My mouth, hers was a pink plastic device but I could feel it straining at the cage.
Mine was the same ,my cock was hurting as it pressed against my cage put I was so turned on I couldn't get it to stop hurting.
I could feel precum leaking from Tanya's cage.
Shall I let them out!! Shouts mistress.
A lound Yes came back from the crowd.
Mistress unlocked the cage and beckoned us out .
We both crawled out . On your knees she commands.
It's competition time ladies and gents. We need two contestants.
She picked 2men from the audience. One was a young man in his twenties a very good looking pads who obviously worked out dress in a DJ and red bow tie. The other was a large man in his Fifties. Balding also in a DJ with his gut hanging over his belt.
We'll toss a coin mistress says she flips a coin heads or tails she asks the young man heads he says. Heads it is she say which one do you want. Oh Tanya he says, my heart sank. The fat man stands in front of me. Right gents the first one to cum wins.
Girls start sucking.
Tanya eagerly unfastens the young man's flies and pulls out a large thick cock.
Come on you stupid girl complains the fat man get to it.
I unzip his flies to reveal a short but thick cock. |
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By *rhuges OP Man
over a year ago
Cardiff |
At this point Tanya was well away with the guy face fucking her pretty face. The fat man looses patience and pushes my head toward his cock ,he starts face fucking me to try to catch up.
All of a sudden the young man let's out a moan as he ejeculates into Tanya's mouth. Open your mouth orders Mistress, Tanya opens her mouth to show that it's full of cum. Swallow ! Tanya swallows and there is a cheer from the crowd. You stupid girl complains the fat man and pulls my head off his hard cock and slaps my face.
You loose Barnard laughs Mistress. I see she hasn't made you cum, no says the Barndard.
Well we can't have that can we. She addresses the crowd. What should we do about that she asks.
The crowd all say in unison Fuck her Bernard.
Bring out the fucking bench demands mistress. Two men carry on a wooden bench padded on the top |
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By *iM4kinkMan
over a year ago
San Antonio |
"A blanket is then thrown over the cage. We feel the cage now being pushed. He hear a lot of background chatter as the cage stops.
The blanket is pulled off
We hare in a large hall with men and women in smart evening dress.
Mistress is standing my the cage. Some entertainment she shouts .
Get them to suck each other off shouts a young women in a black cocktail dress.
You heard says mistress in a low voice get to it.
We managed to get into a sort of 69 position and start licking each others chastity device.
They've got cages on laughs the womenlets see if they can still cum.
I have Tanya's lovely cock I. My mouth, hers was a pink plastic device but I could feel it straining at the cage.
Mine was the same ,my cock was hurting as it pressed against my cage put I was so turned on I couldn't get it to stop hurting.
I could feel precum leaking from Tanya's cage.
Shall I let them out!! Shouts mistress.
A lound Yes came back from the crowd.
Mistress unlocked the cage and beckoned us out .
We both crawled out . On your knees she commands.
It's competition time ladies and gents. We need two contestants.
She picked 2men from the audience. One was a young man in his twenties a very good looking pads who obviously worked out dress in a DJ and red bow tie. The other was a large man in his Fifties. Balding also in a DJ with his gut hanging over his belt.
We'll toss a coin mistress says she flips a coin heads or tails she asks the young man heads he says. Heads it is she say which one do you want. Oh Tanya he says, my heart sank. The fat man stands in front of me. Right gents the first one to cum wins.
Girls start sucking.
Tanya eagerly unfastens the young man's flies and pulls out a large thick cock.
Come on you stupid girl complains the fat man get to it.
I unzip his flies to reveal a short but thick cock."
i fucking luv the humiliation, a dream for a filthy, submissive little sissy whore like me. |
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By *iM4kinkMan
over a year ago
San Antonio |
Omfg train and use me already, i'm a filthy bitch good for unloading in and breeding. |
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By (user no longer on site)
over a year ago
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Love to be treated like this x |
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By *harbiMan
over a year ago
london/Reading |
Wow so hot, lucky girls |
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By *athytvsubTV/TS
over a year ago
Bulwell, Nottingham |
Loving this, making me strain in my cage xx |
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By (user no longer on site)
over a year ago
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Love it   |
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By *rhuges OP Man
over a year ago
Cardiff |
They put the bend down. It's just below waist hight.
I bend over it as instructed.
My hands are fastened at the front and my legs at the back with velcro straps. Tanya is brought behind me.
The crowd chant lube her up lube her up laughing as they chant.
Tanya is given a tube. I feel the cold lube being spread on my arse. Work it in Tanya instructs mistress. I feel one of Tanya's fingers enter me I give out a girly shreak.
Then two then three fingers , .Her fingers start fucking my arse working the lube in. Look crys some one she's getting a stuffy. My cock is indeed straining against it's cage.
Ok Tanya on your knees commands Mistress
. Tanya gets on her knees and Bernard steps forward with is semi hard cock sticking out of his pants.
Bernard steps out of his pants and stands in front of Tanya. Make him stiff make home stiff chant the crowd.
Tanya starts sucking Barnard's cock. She definitely better at this than Jacki Bernard says addressing the crowd.
Right says mistress guide the cock into Jacki
Tanya takes his cock out of her mouth and covers it with lube before guiding it between my cheeks.
I feel it at my entrance.
I squeal as his cock enters me. Bernard pushes it all the way in. Then slowly starts to withdraw it, the back in. He then starts to fuck me slowly at first but the starts to get faster and harder.
I'm squealing with both pain and pleasure ... |
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By *rhuges OP Man
over a year ago
Cardiff |
I feel his gut against the outside of my arse as he pumps his cock inside me.
He suddenly stops and moans as he shoots his seed inside me and withdraws.
Everyone claps.
Tanya clean her up demands Mistress. Tanya knees NB my arse and starts licking up the cum dripping from my arse.
And that's how you treat a Sissy laughs Bernard addressing the crowd.
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I really enjoyed reading that story would love to be that sissy |
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By *rhuges OP Man
over a year ago
Cardiff |
Tanya is told to unstrap me. I get off the bench and am told to get on my knees.
Right says Mistress Jacki you have a choice. You can get up and walk out and never come back or you can be my property, and your first job would be rented out to Bernard here as his slut.
I look at mistress, my head is saying get up and walk out my cock is saying the opposite, well which is it Jacki??
I heard myself saying I want to be your property mistress. Good girl says Mistress. I'm delighted.
Right that's enough for this evening. Please report back here tomorrow at 9am.
I had some holiday due to me at work so I booked a week off.
That night I was thinking the sensible thing would me not to go back.
I found myself knocking on the door at 8:55 the next morning.
Mistress invited me in and was given to Jane for my transformation a gain .
This took about 1.5 hours.
I was dressing in white blouse black pencil skirt and high heels. I was lead out to a white van. Don't you dare let me down Jacki I heard mistress call as the van drove away. About 45 mins later it stopped. The door was opened and I was lead to a rear entrance. A knock on the door and the door was opened by Barnard in a smart 3 piece suit.follow me he said.
I followed him up the stairs and into a large office. He takes me around to the back of a large desk. Under you go he commands. I bend under the desk I can sit quite comfortably under it.
He then sits in his seat.
Right he says pleasure me!
I unzip his flies and take out his semi card cock. Just then I hear a knock on his door Come! He says. Then quitely to me carry on slut.
I hear a number of people enter the room as I place his cock in my mouth. I hear him say Mr Jenkins your sales figures are atrocious can you please explain why. Mean while I have his cock I'm my mouth sicking on it .
Mr Jenkins trys to defend himself, but Bernard wasn't having any of it.
You need to turn around those figures Mr Jenkins do you under mstand? Yes Sir he says.
I found this was really turning me on |
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By *rhuges OP Man
over a year ago
Cardiff |
He was now hard in my mouth as I held his balls in my had and sucked and licked his short thick cock.
. Right he says. I have an online meeting now everyone out.
Everyone trailed out.
He pud his chubby hand upder his desk and strokes my hair good girl he says.
I feel him tension before filling my mouth with his cum. Swallow there's a good girl he commands.
He looks down ,open wide he commands, I open wide and he examins my mouth butting his fingers inside.
He takes a large signet ring from his finger and puts it in my mouth. Clean it he commands, I suck it and then polish it with a cloth before placing it back on his finger.
At lunch time his meal is brought into him by his secretary . A plate of sandwiches. He break to bits of the sandwich and feeds them to me under the desk.
I then have to suck his cock again in the afternoon. I find it a real turn on to be commanded by a man of power .
5 pm comes and people start leaving ,by 5 30 everyone apart from Bernard have left.
Right my girl he says out you come time for a sound fucking for you.
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Horney story.precum dripping.mmmm |
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Please continue when you can really enjoying this |
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By *rhuges OP Man
over a year ago
Cardiff |
He grabs my wrist and pulls me up. Look what your mistress gave me sissy he smiles, and shows me a small key. Skirt down he commands .I unfasten my skirt and let it all to the ground showing my red camio panties.
He pulls down my oanties and unlocks the chastity device and removes it. What do you say ? He asks. Thank you sir I say giving him a curtsy.
He bends me over the front of his large mahogany desk so my arse is exposed. I feel the lube being worked into my hole.His hard cock is now at my entrance . He slowly pushes it in, using one of his hand to play with my cock. I see you're enjoying this he says as he milks my hard cock .
He slowly pushed it in I squealwith the initial pain , but the pain turns to intense pleasure as he slowly fucks and milks me .
In no time at all I cry oh sir as I squirt my warm white cum over his hands.
A few seconds later I feel the jet of his cum inside me as he moans.
He pulls out turns me around and has me luck my cum from his large chubby hands.
You like a powerful man to play with you don't you sissy. Yes Sir I say. Well he says Thank me. Thank you for fucking me sir I say good girl he laughs.
He than gets the chastity device , please leave it of sure I beg,you know this is for your own good sissy now me a good girl and fit it for me.
He watches as I fit the device on and click the oad lock in play.
He makes a call, your pick up is in 5 minutes he says, he goes to the safe and removes a bundle of money. You're not cheap he laughs.
With that he leads me down the stairs, I can feel his cum dripping from my arse making my panties wet and sticky .
He opens the side door as a black SUV turns up. The rear door opens and I step in. Mistress is driving. She opens her window and Barnard hands her the money. Was she a good girl Bernard she asks. Oh a very good girl he says. I would love to use her again sometime . Mistress smiles closes the window and we speed off |
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By *rhuges OP Man
over a year ago
Cardiff |
She drives me back to her house were I shower and get dressed . When I reappear. Mistress asks me if I want to call it a day or carry on.
I want to say call it a day ,but I hear myself saying carry on please mistress .
My cock straining against the chastity device.
Go home get some rest and report back here at 10am she says.
The next day I'm up dressed in the lingerie I was given and then just a trench coat on as instructed by text earlier that morning.
I arrive on time and ring the bell .
Jane answers the door. She basically looked after all of mistresses sissies a large lady but makeup and dress always immaculate.
Come in she says cheerfully. Mistress has popped out so will not be back for a few hours ,let's get you made up ready for her return.
She leads me into the makeup room .
She sees me eyeing up her large breasts and laughs, only good girls get to play with these she laughs, I was a really good girl for mistress last night I beg.
Jane smiles, sits me in the chair and wriggles out of her tight black dress revealing a purple Basque and matching stockings and pantries.
She releases her breasts from their cage and the flip out. The nipples are huge. I go to suck one, no not yet she scolds and pushes me down between her large soft white thighs |
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By *rhuges OP Man
over a year ago
Cardiff |
Her hand pushes my face against her sweet wet pussy. My tongue enters her and works as deep and as hard as I can her thighs grub my head as I probe her.
I hear a door open then mistresses voice, what the hell Jane, I've warned you about sampling the merchandise before Jane. I can't over look it this time.
Sorry Alexa can we carry on this conversation in private.
NO! Says mistress's come over here. Jane pushes me away. With here breasts still out she walks over to were mistress is and starts to pop them back into her Basque, no says mistress leave them out.
Over that chair now. Really questions Jane, Infront of the sissy?!??
Yes says mistress she looks at me on your knees sissy and watch.
Still protesting Jane bends over the chair. Mistress produces a paddle from a cupboard whack whack whack whack. Ooh Jane complains thats enough !! She cry angrily. Whack whack whack whack whack. Her large white arse is now turning pink and red .
Now get up and make the sissy up as I instructed. Yes Alexa Jane says wiping the tears of pian and humiliation from her face |
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By *rhuges OP Man
over a year ago
Cardiff |
Mistress leaves the room and Jane make me up in silence.
Right you're done she says .
Follow me. She leaves the room I watch as her large gorgeous arse wobbles.
I follow her. Mistress is waiting , oh she says to me don't think you've got away with his mornings antics Jacki.
Yes mistress I say hanging my head.
Janes face flushes red with embassment
.
Right she says to Jane maybe I was a little harsh on you Jane , no you were right Jane says. Never the less I think you deserve some fun. Go get your strapon. Jane smiles and disappears out of the room |
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Absolutely loving this for obvious reasons can’t wait to read some more what a fantastic story |
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Wonderful story.... can't wait for next installment. xxx |
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By (user no longer on site)
over a year ago
|
Carry on please |
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By *rhuges OP Man
over a year ago
Cardiff |
I'm left in the room on my own. I hear voices heading my way. Mistress enters the room with 2 guests. A young couple in their 20s . The girl is wearing a light short green dress shapely tanned legs an green shoes with kitten heels. Her partner, a muscular young man with short dark hair in chinos and white polo shirt .
Mistress shows them to the plush sofa in the room. She then addresses me curtsy to our guests Jacki she says. I do a deep curtsy. I am filled with embassesment and shame knowing the this couple are young enough to be my kids.
Just then Tanya appears with a silver try with two flutes of champagne caviar and crackers lays them on the table by the sofa and curtsies.
Line up next to Jacki mistress commands .
We both stand infornt of the couple.
Give us a twirl laughs the girl sipping her champagne. We both turn on the spot for her.
Lift up your skirts says the young man . We both lift up our skirts.panties down he says.
We pull our pantis down.they both start to laugh. Arrrr how cute they're both caged laughs the girl. She looks at Mistress Alexa any chance we can get those cages off?
Certainly says mistress
She unlocks both our cages and removes them.
Both the girl and the young man start laughing. Imagine if you had a cock that small Hun laughs the girl.
Girls play with each others cocks show our guest what they look like hard.
I felt my face go red.
We held each others cocks and slowly milked them.
Within a minute both were hard.
Which one do you think is the biggest Hun laughs the girl.
Not sure but I thing Tanya's
Just wins.
With that Jane reappears dressing in her purple Basque and large black strap on .
Right says mistress ,which one of these sissy do you want Jane to fuck,?? |
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More more please .. I need this |
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By *rhuges OP Man
over a year ago
Cardiff |
The young couple have a discussion of which one of us sissy's they want to watch Jane fuck.
The girl tells us to turn around pull up our skirts and pull down our panties so they can see our arses.
I hear them say that sissy's arse is slightly bigger than that one's but that one's got a better shape. I felt like an animal being auctioned off. Sadly this really turned me on ,I couldn't hide it with my cock becoming harder .
Look laughs the girl that sissy has a stuffy. We'll choose the other one please Alexa.
Jacki mistress says secure Tanya to the fucking bench.
I obediently strap her hands to the front part and her legs to the rear so her arse is sticking up in the right position to be fucked.
I am then giving the lube which I spread amply around her arse and inside it. I then lube up the stapon.
Jane approaches Tanya and starts to insert the strap on. Tanya let's out a little cry as it penetrated her. Jane's slowly eases it into her bit by bit ,with Tanya squealing as it's pushed in. She gets it about half way before slowly pulling it out and then pushing it in.
The young couple look on sipping their champagne and eating their caviar.
The girl says to the young man, do you fancy the other one pleasuring you while we watch?
Why not he says, slut he commands over here . I kneel between his legs Well? He says have you got something to say to me. Please sir may I have the honourof pleasure you. They both start to laugh , well he says still laughing since you asked so nicely you may |
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By *rhuges OP Man
over a year ago
Cardiff |
He undoes his belt and pulls out a large semi effect cock. I move forward and start to suck his cock good girl he says stroking my hair.
I can hear Jane fucking Tanya behind me. Fuck her harder demand the girl. Jane's rythme speeds up, deeper demands the girl. I hear Tanya squealing. The girl gets up with her champagne and walks over to were Tanya is being fucked. She bend down and starts laughing Hun she calls the dirty slut is enjoying this her tiny cock is kinda hard.
She grabs Tanya's cock and starts to milk her, like that do you slut she asks. Yes mistress Tanya replays in between girly squeals.
The girl then walks over to Jane and starts feeling her large breasts. Get them out for our guest Jane Mistress demands. Jane stops and releases breasts from her Basque, did I tell you to stop fucking asked the girl irritated, no sorry says Jane and starts fucking Tanya again. Her large tits bouncing about. The girl starts massaging Jane's large nipple on her left breast Jane murmers that's so nice . |
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By *rhuges OP Man
over a year ago
Cardiff |
Don't look at her bitch look at me said the young man. He but his hand on my head and started to face fuck me. I gagged a few times as he deep throated me. He's cock slipped out, he picked it up and slapped me across the face with it. Back in he commanded, my mouth slip over his cock again.
The girl was now massaging both of Jane's large tits ,Jane was moaning with pleasure. She then starts to kiss Jane on the lips , keep fucking her the girl managed to say before her tongue was down Jane's throat.
Tanya was now squealing like a naughty girl as the large strapon was going all the way in and out. |
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By *rhuges OP Man
over a year ago
Cardiff |
His cock slipped out of my mouth, lick my Balls you sissy bitch he says. I turn my attention to his balls I lick and kiss them then lick and kiss his cock from the hilt to the tip. That's right he moans worship it.
He tenses as his cum shoots to the back of my throat, he pulls out. He graphs my chin and looks straight into my eyes open wide I want to make sure you've shallowed all of it.
I open my mouth wide and he inspect it. Good girl he says, room for improvement though. I kneel by his side.
Tanya is still tied to the bench Jane has now got the girls tots out, they are gorgeous, well formed perky and tanned. Jane has her head beried between the girls breasts .the girl has her hand up Jane's skirt and is obviously fingering her pussy with the amount of moaning Jane's doing.
Get a room you to the young man laughs.he looks at me go until the sissy then bring her over here.
I untie Tanya and bring her over. You he says to me lay on your back I front of me. I lay on my back he points to Tanya 69 her he commands. Tanya straddles me so her cock is inches from my mouth and mine inches from hers.
Right he says the first one to cum wins. Go!!
We start sucking each others cocks . I love the taste of Tanya's cock and as it's not too big O could take it all in without gagging.
My cock is now rock had and I can feel precum leaking out of it into Tanya's mouth |
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By *rhuges OP Man
over a year ago
Cardiff |
This was the total humiliation sucking a sissy's cock for the amusement of a 25 year old.What the hell was I doing. I was a 45 years old senior manager, but I found this over riding want to please and serve this young man.
I moaned as I ejeculated into Tanya's move ,I raised my hand as I felt Tanya's warm white cum fill my move.
The young man claps ,oh well done bitches now stand up and don't you dare swallow emany of it.
We stood up facing each other. Righ start kissing like to naughty school girls I want that cum to be mixed in your mouths. We start kissing I feel the cum from Tanya's mouth enter mine.
Just then Mistress appears ,well Giles I see your enjoying yourself and I see Sophie has come out of her shell .
Sophie is sitting on top of the fucking bench tits out dress around her middle with Jane ensconced between her legs with her tongue deep in her pussy.
Times up I'm afraid says Mistress,Oh Alexa another 10 mins ???.
Ok Giles I'll be back in 10.
Sophie he called which one of these sluts shall we get to fuck Jane??
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Every single time I read this it makes my little sissy cock hard |
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By *rhuges OP Man
over a year ago
Cardiff |
I hear a loud moan as Sophie orgasms , her juices flood over Janes head.
I'm sorry that will not be happening she says to Giles , I'm not one of Alexa's sluts. Just then Alexa comes back. Giles says one of your sluts is back chatting me Alexia.
Which one she asks. Jane he says pointing to her.
Oh Alexa laughs Jane is my madam, she only performs either because she wants to for for profit.
Oh says Giles Jane I'll give you a £500 tip if you fuck one of the sissy's. Make it £600 and I'll fuck your mother she laughs. Ok £600 it is.
Which one she asks? Which one do you think Sophie? asks Giles .
That one she says pointing to me.
I was please as I really fancied her , but fucking like animals to please a couple ,where was my dignity.
Sadly my cock was taking over and was now rock hard.
How do you want it asks Jane?
Jane was dressed in her purple Basque,her large tits hanging outside and black stockings. ,I was now completely naked apart from a pic about bra and black stockings.
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By *rhuges OP Man
over a year ago
Cardiff |
How do people want Jane to fuck the sissy?? |
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"How do people want Jane to fuck the sissy??"
Who cares . Lucky sissy |
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By *rhuges OP Man
over a year ago
Cardiff |
Get the sissy to fuck her with her tongue laughs Sophie.
Sissy on your back commands Giles .
I lay on my back, I see Jane walking over. Sit on her face Jane .I see Jane's large white arse coming toward my face. Have her rim you first laughs Giles.
Jane's arse sits on my face my tongue instantly starts to lick ,are soft white arse spreads across my face as I force my tongue inside her arse. Nmmmm moans Jane as I lick are gorgeous arse. Move back so the sissy can tongue your pussy laughs Sophie. Jane moves her position, allowing me to take a deep breath , Jane's weight was crushing me .
I started licking are wet pussy her juices already dripping onto my face. Oh god she grabs my cock and starts wanking it.
She starts moving back and fourth as she gets a rytham slowing my tongue is deep inside her as I sport my cum over her hands. Don't you dare stop sissy Jane moans |
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By (user no longer on site)
over a year ago
|
Brilliant story. |
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By (user no longer on site)
over a year ago
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By *rhuges OP Man
over a year ago
Cardiff |
Jane suddenly squats and moans loudly and squirts her love juice, soaking my face and the wooden floor.
Sophie and Giles both clap.
At that moment I wanted to be Jane's sissy bitch more than anything else. Jane gets up and pops her large tits back into her Basque.
Sophie's says look at the mess on the floor. Both of you in your hands and knees and luck it up.
Tanya and I both went on our hands and knees and started licking you Jane's juices.
I couldn't believe I was letting this slip of a girl totally humiliate me.
Alexa coming in. Right she says to Giles and Sophie have you had a good time?
Fantastic laughs Giles, we'll definitely come again what do you think Soph?.
I've had a great time she says adjusting her dress.
With that they both get up and leave.
Jane comes back into the room now dressed in black dress and heels .
That was great Jane Alexa says I see the money is but into your account today .
You two says Alexa stand up. We stand up Jane walks around to the front.
Again I give you a choice have your chastity devices fitted and carry on or leave and never come back.
Tanya immediately says my I say mistress, you may Alexa smiles Jane file her cage back on.Janes fits the cock cage on Tanya. And Jackie she asks? My head is shouting run and never come back, but I hear my self saying fit the device mistress. Jane fits the device on me.
Right she says off you go and I'll see you both back here tomorrow at 10Am.
I realized the all I wanted to do was please Jane in anyway I can
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By *rhuges OP Man
over a year ago
Cardiff |
I went home that evening realizing I only had another 4 days of holiday left.
I didn't mind what I had become or how humiliated I was ,all I want to do now was to please Jane and Alexa.
I had a long soak in the bath that evening removing all body hair .
I was 45 but kept myself in good shape and probably could be mistaken for a 35year old with good makeup. I reackoned Tanya was early thirties.
I hadn't really been bi until this point, I mean I'd sucked a few cocks in the past but that was it.
Any way the next morning I dress in clean lingerie ,but on my trench coat and drive over to Alexa's mansion.
I knock on the door at exactly 10am. Jane answers wearing a fabulous thin pink dress, I could clearly see her nipples staring to get out.
Good morning Jackie she says follow me.
I follow her into the makeup room were she make me up as normal. The whole process now took around 45 minutes.
Did you enjoy yesterday ? Asks Jane. Very much so I say , although it was extremely humiliating having such young people in total control of me.
She laughs, I bet that made it even more of a turn on you dirty bitch she laughs. I smile in agreement.
Right she says follow me to see what's intore for you today.
I think you're going to like it she laughs. |
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By *rhuges OP Man
over a year ago
Cardiff |
I follow Jane into one of the offices. I find it quite natural now to swing my hips like a girl.
Alexa is sitting down at year office.
Hello Jackie she says take a seat.
Barnard wants to see you again, he was delighted with your performance last time, your one of our highest earning girls.
Alexa smiles at me yes your doing better than Tanya if your wondering.
So our proposition is you meet selected clients of our choice and you will be Jane's second in command, James bitch if you like. How does that sound she asks me.
What will be my duties under Jane I ask. Well it will be looking after the other sissy's when required and seeing to all Jane's needs.
What do you say.
Oh yes please Mistress I say.Good girl says Jane. Now follow me. I follow Jane out of the room and back into the makeup room.
She sits on the chair and spreads her large white stockinged thighs apart.
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By *rhuges OP Man
over a year ago
Cardiff |
Her cut glass home counties accent was a huge turn in for me. I place my head under her skirt and push her white frillies to one side .l lick the outside of her gorgeous wet pussy and smell the aroma before darting my tongue inside her. As I start eating her out she moans oh yes you have hit the spot Jackie don't you dare stop arrrrrr oh god that's good arrrrrr and with that she cums claiming my head between those large soft white thighs.She stiffens and then relaxes, I remove my head. Go clean yourself up there's a darling she says still panting.
When I return she lifts up my skirt pulls down my panties and removes the chastity device .
Right she says no playing with it without my permission or this goes back on do you understand . Yes Jane I say. Good girl .
Right she says we have a new sissy just come I today. Will you collect her from the waiting room. She's called Rachel.
I leave Jane and walk to the waiting room. I young man is sitting there . Oh I say I'm looking for Rachel. Oh that's me says the young man. Follow me I walk back to the make up room were Jane was waiting.
Right days Jane to Rachel, strip let's see what I'm working with. The young man starts to remove his clothes.
He is completely hair free and has a thin feminine body.
Jackie fit the chastity device. I hold Rachel's cock , it starts to swell. Shall I milk her first I ask? Yep I think that's a good idea.
Rachel's cock is now very hard as I slowly wank it.I hear her gasp before shooting cum sliver my hand and floor.
I put my hand up to her face and say clean it off. Jane smiles at me. Rachel licks all her cum off my hand and the floor |
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By *rhuges OP Man
over a year ago
Cardiff |
Jane's mobile rings. She answers it, really ? She questioned ok. She but the phone down went in a cupboard and took out a pink collar and leash.
I lift Rachel's hair off her neck for the leash .
Jane say sorry Jackie the leash is for you not Rachel.
What do you mean ?I ask
Sir Barnard,s here ,we want me to lead you into him like a dog. What ? I say I'm not doing it!!
With that I feel a sharp pain across my face as Jane slaps me across the face.
You have forgotten your place madam she scolds, you will do what your told or go home.
I look across at Rachel, I see her shoulders going up and down trying not to laugh.
I was thinking about leaving when Mistress appeared, what's the delay? she asks
Jackie is getting above her station Jane complains.
Right we'll see about thatShe grabs. She sits in a chair grabs my wrist and pulls me over her knee. Right my girl she says as she pulls down my panties whack whack whack whack whack whack whackwhack,my arse turns red, we'll had none of this nonsense my girl or you'll be going home. Do you want to go home?? No I cry Whack whack whach whack.Im sorry mistress please forgive me. Give my the collar she says to Jane. Jane gives her the collar and she fits it around my neck.
On all fours she demands I go on all fours hold this ,she hands the leash to Rachel. I felt my face going bright red I felt so humiliated Infront of Rachel. She was trying not to laugh.
Sir Barnard is ready she says to Jane. I'm lead out of the room on all fours.
Sir Barnard was a CEO of a multi national a very powerful man in his mind 60s. About 5ft 8 and about 3 stone over weight .
How very embarrassing it was it was a huge turn on being submissive to a powerful man .
Sir Barnard was in l large padded chair as I was lead in and the leash handed to him
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By *rhuges OP Man
over a year ago
Cardiff |
Jane hands the leash to Sir Bernard. Alexa coming in Sir Bernard she say, do you mind if one of my new girls come in and watches, there would be a small deduction in your fee. Not at all dear girl he says. To my shame and embarrassment Rachel totters in in her high heels. Go kneel in the corner Rachel and observe.
Yes Mistress she say.
Sir Bernard pulls my leash toward him and pulls my head between his legs. Get on with it girl he says.
I unbuckle his pants and put my hand into his pants and pull out his short cock.
Lick the end he orders. I delicately touch the end of his cock with my tongue, then pull the foreskin back and lick around the head before putting it in my mouth |
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By (user no longer on site)
over a year ago
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Wow ….. love to be treated like this , whited out as a little sissy |
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"Wow ….. love to be treated like this , whited out as a little sissy "
. You and me both |
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By *rhuges OP Man
over a year ago
Cardiff |
Rachel is it Barnard says come over here and hold her leash. Rachel totters over in her high heels and takes hold of my leash. That feels good doesn't it he says, yes sir she says.
He pushes my head deeper onto his cock . He moans as he moves my head up and down his cock.
He pulls my head up. Right he says to Rachel walk her over to the fucking bench
I'm lead by Rachel ,I am furious that this sissy is being used as my superior.
Strap her down. She straps my hands to the front and legs to the back with my arse in the air.
Right says Barnard did you know Rachel a sissy arse becomes more relaxed after a spanking. No she giggles.
Well Rachel what are you waiting for give her a spanking.
I'm not having this I think and start Struggling.
Bernard walk round to the front Rachel come here, hold your foot up so Jackie can kiss it.
I move my head away from her foot. Jackie don't be a silly girl kiss her foot! Now!! he demands.
I reluctantly kiss her foot ,now the other one ,i am so humiliated .
Right he says I want that arse nice and red !! |
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By *rhuges OP Man
over a year ago
Cardiff |
Rachel stands behind me and Whack Whack Whack Whack, harder demands Sir Bernard ,Whack Whack Whack Whack. If you want her to stop sissy you'll have to ask her nicely he laughs Whack Whack Whack Whack. Stop!!! I demand Whack Whack Whack Whack call her mistress he laughs my arse is now red and burning. Please mistress Rachel stop I cry. You may stop now girl says Sir Bernard
He gets up and unbuckles his belt. His trousers fall to the ground. Rachel lubes my sore arse , then guides Sir Bernards cock into me. He starts pumping I squeal as it enters me as he starts to fuck me. I see they haven't put a cock cage on you slut Rachel get under her and start sucking her cock |
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By *rhuges OP Man
over a year ago
Cardiff |
As Sir Bernard was pounding me Rachel was sucking in my cock. Jane came in and laughs two for one Sir Bernard you naughty man she laughs.
I can see we need to put thatcock cage back on you Jackie she says, but Jane I plead it wasn't my fault.
We will talk about this later my girl she says in a cross voice. Just then Bernard pants as his cock shoots his cum into my arse.
He pulls out and pulls his trousers back up.
I trust the session was to your liking Sir Bernard Jane asks.oh spot on dear girl he smiles spot on.
Sir Bernard leaves the room.
Rachel has let my cock go but is still under me.
Untie her Jane's says crossly to Rachel.
I'm untied
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By (user no longer on site)
over a year ago
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Carry on please |
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By *rhuges OP Man
over a year ago
Cardiff |
Rachel take Jackie's lead and follow me. Jackie on all fours!
Total humiliation for me with Rachel holding my lead.
We gointo the hall were mistress is waiting . Well Jane she says was Sir Bernard happy??
Yes I think he was Alexa, but this one was acting a bit bratty. Oh dear says Alexa after we gave her the chance to supervise the other girls.
Rachel I know you're new but we will give you a go. Jackie can be your pet. Jackie you do as Rachel says do you understand !!!!
I was going to complain when Alexa says. If you dare complain you will not have a choice, you will be leaving do you understand?? I say nothing. I said do you understand? I still say nothing. Right say Alexa your out of here, part of me felt relieved but I suddenly found my self saying please mistress give me another chance I promise to be a good girl.
Well what do you think Jane? Alexa asked. Oh give her a chance but she does need to be punished. Agreed says Alexa. How would you like to punish Jackie Rachel ? Alexa asked |
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By *rhuges OP Man
over a year ago
Cardiff |
Let me think smiles Rachel. She whispers something in Jane's ear, at humiliation rather than pain I like it. Jane gives Rachel the key to her chastic device. Rachel gives me the key ,unlock it demands Rachel. I kneel and unlock the device and take it off.
I remove the device , now says Rachel suck it!!
The humiliation was complete.
We haven't got all day laughs Jane. I take Rachel's cock in my move and start sucking it. I can feel it grow in my mouth.
Rachael starts to face fuck me causing my to gag , Jane and Alexa laugh. She goes stiff and shoots her cum into my mouth, swallow she demands. I swallow. Rachel puts her fingers in my mouth to check I'd swallowed her seed. Right she says fit it on your self . I fit it on my soft cock key she say. I hand Rachel the key. If your a good girl she says I may milk you one a week.
Both Alexa and Jane laugh. Come on say Jane follow me Rachel.
Rachel pulls my lead and says heal!! On all fours. I crawl after her into the makeup room.
Jane shuts the door. She lifts her large breasts out of her dress. Her nipple's erect. I get up to suck them. Down girl Jane's say down.
Rachel. Rachel moves forward and places her lips on Jane's nipple.
Stay she said to me |
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Loving this story - especially the introduction of my namesake  |
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By *rhuges OP Man
over a year ago
Cardiff |
Rachel turns to be, rim my arse bitch. Now! Jane laughs, arn't you the dominant one Rachel she says, well Jackie get to it.
I lifted up Rachel's short leather skirt and pulled her pink frillies to one side. I parted her pert arse cheeks and started rimming her. Good girl Rachel moaned as she switched nipples .
Rachel's arse tasted sweet I found that I was doing my best to please Rachel. My hand went around to Rachel's front and touched her cock.
It was hard . Come around the front Rachel moans I slipped in between them . Worship my girl cock Rachel moaned. |
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Omg this is Turning me on so much I’m struggling to keep my cock in his cage I need to release it fantastic story |
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I need more of the story. .. It certainly puts me in my place |
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By (user no longer on site)
over a year ago
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Carry on please |
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By *rhuges OP Man
over a year ago
Cardiff |
I couldn't humiliate my self anymore, I got up and said No!!
Jane looked at me ,
Rachel's head was buried in her large gorgeous tits
Jackie she says calmly think what your doing you silly girl. Your free to go but there will be no way back for you. I'm head was says I need to get the fuck out of this situation, but my cock was rock hard and I felt hugely turned on with the humiliation.
Well Jackie ? Jane asked what's it to be?
I got on my knees and started to but Rachel's cock in my mouth.
Oh now says Rachel taking her head out of Jane's Tits.
You act like that and expect no repercussions for your outburst ? Sorry I say ,Sorry what? Demands Rachel. Sorry Rachel I say. No sorry mistress Rachel she says and looks at Jane. Jane's says yes Jackie address her as mistress, yes mistress Rachel I mumble.
Right you have to earn the right to suck my clit. Lick my arse !! |
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...horny 
