Naughty Chris

Played around and now he's locked away.
September 13
You look distraught. That must have been quite some thrashing you got from Mr Hardcastle? And quite a load of ironing you brought back with you, I guess he wasn’t joking when he said he would get his daughter’s family’s washing for you too! Thirty strokes of the dragon cane, my… no wonder you can’t walk properly. I guess you won’t be asking to caress my bottom again will you? You cheeky boy! Mr Hardcastle certainly does a better job of punishing than I ever did! Anyway, that’s no concern of mine. I’m about to go out to the theatre with Greg now…. he is going to love this outfit don’t you think? And I can promise you that we’ll be having a happy ending to the night, which means you will need to give Mr Hardcastle another blow job too!  Now I guess you are going to be ironing for Mr Hardcastle at least until ten o’clock… after which I want both bathrooms scrubbing clean, the bedroom dusted and vacuumed ready for us when we get back, then I want the kitchen floor and benches scrubbed, and you’ll need to clean the oven that you forgot to do last night. So it is going to be a long night for you, which will hopefully take your mind off the pain….. and don’t forget, it’s saturday tomorrow and I expect you to be up by six am to start work on the back yard. It is so good having you to do all the chores like this… and all for just a glimpse of my legs every now and then. You’re so easy to please :)

You look distraught. That must have been quite some thrashing you got from Mr Hardcastle? And quite a load of ironing you brought back with you, I guess he wasn’t joking when he said he would get his daughter’s family’s washing for you too!

Thirty strokes of the dragon cane, my… no wonder you can’t walk properly. I guess you won’t be asking to caress my bottom again will you? You cheeky boy! Mr Hardcastle certainly does a better job of punishing than I ever did!

Anyway, that’s no concern of mine. I’m about to go out to the theatre with Greg now…. he is going to love this outfit don’t you think? And I can promise you that we’ll be having a happy ending to the night, which means you will need to give Mr Hardcastle another blow job too! 

Now I guess you are going to be ironing for Mr Hardcastle at least until ten o’clock… after which I want both bathrooms scrubbing clean, the bedroom dusted and vacuumed ready for us when we get back, then I want the kitchen floor and benches scrubbed, and you’ll need to clean the oven that you forgot to do last night. So it is going to be a long night for you, which will hopefully take your mind off the pain….. and don’t forget, it’s saturday tomorrow and I expect you to be up by six am to start work on the back yard.

It is so good having you to do all the chores like this… and all for just a glimpse of my legs every now and then. You’re so easy to please :)

(via chastewiddlesissy)

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Take a little look sweetie.  Awww…. Does that get you all frustrated and sore with your little weenie locked up tight for a whole year now? I have told you before, don’t even ask if you can caress my buttocks! My body is totally off limits to you… after all you’re all locked up so why do you even want to frustrate yourself like that? Anyway, for your disobedience you can make an appointment to go see Mr Hardcastle! He can give you the thrashing you deserve… and don’t ask again… OR ELSE. Oh dear…… Mr Hardcastle promised you a caning with his dragon cane if he you misbehaved again this month. Ouch, that is going to hurt frightfully!! No honey, you know I never change my mind. You will report to him as ordered. It’s up to him to decide your punishment now… but I will be thinking of you while I make out with Greg. Now off you go!

Take a little look sweetie. 

Awww…. Does that get you all frustrated and sore with your little weenie locked up tight for a whole year now?

I have told you before, don’t even ask if you can caress my buttocks! My body is totally off limits to you… after all you’re all locked up so why do you even want to frustrate yourself like that? Anyway, for your disobedience you can make an appointment to go see Mr Hardcastle! He can give you the thrashing you deserve… and don’t ask again… OR ELSE.

Oh dear…… Mr Hardcastle promised you a caning with his dragon cane if he you misbehaved again this month. Ouch, that is going to hurt frightfully!!

No honey, you know I never change my mind. You will report to him as ordered. It’s up to him to decide your punishment now… but I will be thinking of you while I make out with Greg. Now off you go!

(via chastewiddlesissy)

September 9
Right Sissy, pay attention. Here are today’s special assignments…. Two o’clock, Mr Brown is coming in…. Take him in to my office and give him a thirty minute blow job…. Of course you have to swallow! Mr Phillips is coming in at seven, after everyone has left. He is into spanking, so make sure you have the heavy paddle out on your desk. I am afraid to say you won’t be sitting comfortably by the time he has finished! Not that that’s a problem as you will be on your knees to say thank you afterwards. After that you can head off home. 

Right Sissy, pay attention. Here are today’s special assignments….

Two o’clock, Mr Brown is coming in…. Take him in to my office and give him a thirty minute blow job….

Of course you have to swallow!

Mr Phillips is coming in at seven, after everyone has left. He is into spanking, so make sure you have the heavy paddle out on your desk. I am afraid to say you won’t be sitting comfortably by the time he has finished! Not that that’s a problem as you will be on your knees to say thank you afterwards.

After that you can head off home. 

(Source: demut1, via femdomhotwifecuckoldinterracial)

September 2

(via strictwomen)

August 22
Well I had a great time with Greg. And I spoke to Mr Hardcastle next door about him being too rough with you. Problem solved. We agreed that you will just get jerked off once a year going forward, so you have plenty of time to recover… I also agreed that whenever I go out to get fucked, you’ll pop round in your maid’s outfit and give him a quick blow job. Fifteen minutes max, as you need to get your chores completed still. I am well aware that means four or five times a week, he’s a real man, and that’s how often they need an orgasm! Don’t be so silly… You get to wear sexy clothes all the time instead. And I show you my legs every now and again. That’s more than you need. Oh, I almost forgot. From now on, Mr Hardcastle will be putting you over his knee and tanning your backside too if your work is not up to scratch. That’s a big help for me… So of course I said you would do all his ironing too, as a thank you gesture. I do enjoy having you as my slave. Now come on over and you can clean all Greg’s cum out of me.

Well I had a great time with Greg. And I spoke to Mr Hardcastle next door about him being too rough with you. Problem solved. We agreed that you will just get jerked off once a year going forward, so you have plenty of time to recover… I also agreed that whenever I go out to get fucked, you’ll pop round in your maid’s outfit and give him a quick blow job. Fifteen minutes max, as you need to get your chores completed still.

I am well aware that means four or five times a week, he’s a real man, and that’s how often they need an orgasm!

Don’t be so silly… You get to wear sexy clothes all the time instead. And I show you my legs every now and again. That’s more than you need.

Oh, I almost forgot. From now on, Mr Hardcastle will be putting you over his knee and tanning your backside too if your work is not up to scratch. That’s a big help for me… So of course I said you would do all his ironing too, as a thank you gesture.

I do enjoy having you as my slave. Now come on over and you can clean all Greg’s cum out of me.

(via chastewiddlesissy)

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I know sweetie, it must be a bit much for you, all locked tightly away like you are. That is why I usually wear jeans or lrack suit pants around you. After all, you wear the panties and skirts in this house. But Greg is coming over and he loves to see my sexy legs. Of course I’ll be having sex with him. A girl needs a real man for real sex too. Don’t be silly, you were never a real man. As if you could ever please me! Why you’d be lucky to last thirty seconds. And I know you keep saying that’s because I only let you out once every three months. But let’s face it, you weren’t that good before I locked it away. Anyway, this is much better for all of us. You work hard in the office all day to keep me in the style I expect, and then you come home and do all the chores. You’d have no energy left if I let you have sex as well! Then who’d do all the chores? So, with no distractions, you can focus on working hard; I can focus on having a good time, without having to worry about keeping you pleased; and the beefy guys I meet each week get to have a great time stroking my legs and screwing me! So you see you really are important to me. And besides, I get that old guy next door to jack you off. Well of course you have to dress in your best frock and suck him off afterwards, why else do you think he agreed to jerk you off. Well if he is too rough, you’ll have to discuss that with him… Now that’s enough ogling my legs, get back to your ironing… my sister will be round tomorrow morning to collect her clothes and your three nieces. So make sure those pleats are razor sharp in all their school tunics… And my Mum will be looking for her stuff tomorrow night too… You don’t want a taste of her cane again I’m sure. Back to it… NOW!

I know sweetie, it must be a bit much for you, all locked tightly away like you are. That is why I usually wear jeans or lrack suit pants around you. After all, you wear the panties and skirts in this house. But Greg is coming over and he loves to see my sexy legs.

Of course I’ll be having sex with him. A girl needs a real man for real sex too.

Don’t be silly, you were never a real man. As if you could ever please me! Why you’d be lucky to last thirty seconds. And I know you keep saying that’s because I only let you out once every three months. But let’s face it, you weren’t that good before I locked it away.

Anyway, this is much better for all of us. You work hard in the office all day to keep me in the style I expect, and then you come home and do all the chores. You’d have no energy left if I let you have sex as well! Then who’d do all the chores?

So, with no distractions, you can focus on working hard; I can focus on having a good time, without having to worry about keeping you pleased; and the beefy guys I meet each week get to have a great time stroking my legs and screwing me!

So you see you really are important to me. And besides, I get that old guy next door to jack you off.

Well of course you have to dress in your best frock and suck him off afterwards, why else do you think he agreed to jerk you off.

Well if he is too rough, you’ll have to discuss that with him… Now that’s enough ogling my legs, get back to your ironing… my sister will be round tomorrow morning to collect her clothes and your three nieces. So make sure those pleats are razor sharp in all their school tunics… And my Mum will be looking for her stuff tomorrow night too… You don’t want a taste of her cane again I’m sure.

Back to it… NOW!

(Source: assart, via chastewiddlesissy)

August 16
Oh I have some fantastic news…. You know I have always had a concern that when you step out out of line, I am not the best one for punishing you…. I mean, I tend to go easy when it starts to hurt and you cry out. And I am sure you take advantage of that. Anyway, I was with Joel this morning, he’s the big, black guy with all the muscles, lives three doors up? You had an argument with him a few weeks back… You ended up reporting him to the authorities. Well understandably he thinks you’re a total prick. Anyway, we were chatting after we made out, he’s very good by the way! He thought it was totally hilarious when I told him how I keep you in chastity and you have to wear ladies’ lingerie. He thinks you must be a real wimp. But that’s not the point…. Turns out he is into a bit of kinky stuff and when I explained my dilemma about how to deal with you when you step out of line…. Well he had the perfect solution. I just send you round to his place and he will deal with you. It should work out really well. He has a real gym horse that he will secure you to. He said nobody, never mind a wimp like you, can be expected to stay in position for a thrashing with the cane he has for you. Seems I have been way too soft with you! He has a 39 inch dead shot dragon cane. That means it has a lead weight at the end, apparently it is frightfully painful. He showed it to me and I have to tell you, it looks positively evil… I mean real scary! I was terrified just looking at it… Still that’s not a problem since it won’t be used on me…. Thank God! I mean I nearly wet myself when he laid a stroke on the sofa! It landed with a retort like a rifle shot. And he said that wasn’t full force! Anyway, we agreed that 12 strokes would be the minimum and 36 strokes the maximum, depending on your offence. Most usually it will be 18 - 24 cuts. I have to draw up a report slip, sort of like at school, where I write down what you are to be punished for. Then we both sign it, and you call him up to make an appointment. He reviews your report slip and sets the punishment… we both felt I might still be too lenient if I decided the number of strokes. Oh honey….. You’re shaking like a baby girl! This gives you such a great incentive not to step out of line. And if you really are that worried… Well just behave yourself, it’s that easy. Of course in return for him disciplining you, I agreed to to fuck him again, but I was going to any way. So this is a real win:win:win; I mean given what he thinks of you there is no way he is going to go soft on you. I don’t have time for your pleading, I’m headed out with the girls, I reckon this dress should pull me a guy later though. I’ll see you after I get back from making out.

Oh I have some fantastic news…. You know I have always had a concern that when you step out out of line, I am not the best one for punishing you…. I mean, I tend to go easy when it starts to hurt and you cry out. And I am sure you take advantage of that.
Anyway, I was with Joel this morning, he’s the big, black guy with all the muscles, lives three doors up? You had an argument with him a few weeks back… You ended up reporting him to the authorities. Well understandably he thinks you’re a total prick.
Anyway, we were chatting after we made out, he’s very good by the way! He thought it was totally hilarious when I told him how I keep you in chastity and you have to wear ladies’ lingerie. He thinks you must be a real wimp. But that’s not the point….
Turns out he is into a bit of kinky stuff and when I explained my dilemma about how to deal with you when you step out of line…. Well he had the perfect solution.
I just send you round to his place and he will deal with you. It should work out really well. He has a real gym horse that he will secure you to. He said nobody, never mind a wimp like you, can be expected to stay in position for a thrashing with the cane he has for you. Seems I have been way too soft with you! He has a 39 inch dead shot dragon cane. That means it has a lead weight at the end, apparently it is frightfully painful. He showed it to me and I have to tell you, it looks positively evil… I mean real scary! I was terrified just looking at it… Still that’s not a problem since it won’t be used on me…. Thank God! I mean I nearly wet myself when he laid a stroke on the sofa! It landed with a retort like a rifle shot. And he said that wasn’t full force!
Anyway, we agreed that 12 strokes would be the minimum and 36 strokes the maximum, depending on your offence. Most usually it will be 18 - 24 cuts. I have to draw up a report slip, sort of like at school, where I write down what you are to be punished for. Then we both sign it, and you call him up to make an appointment. He reviews your report slip and sets the punishment… we both felt I might still be too lenient if I decided the number of strokes.
Oh honey….. You’re shaking like a baby girl!
This gives you such a great incentive not to step out of line. And if you really are that worried… Well just behave yourself, it’s that easy.
Of course in return for him disciplining you, I agreed to to fuck him again, but I was going to any way. So this is a real win:win:win; I mean given what he thinks of you there is no way he is going to go soft on you.
I don’t have time for your pleading, I’m headed out with the girls, I reckon this dress should pull me a guy later though. I’ll see you after I get back from making out.

(via chastewiddlesissy)

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Don’t be so stupid. As if I would go to all this trouble dressing up for you! And don’t even think about touching me. Rick just called to say he’s in town, so I am rushing off to his hotel for the night. I know it’s your night for your monthly release. But this is more important, I haven’t had a good fuck since Wednesday…. So you’ll just have to wait until next month now. No, I am not releasing you tomorrow instead. I’ll need a lie in, and then I am off shopping before a night out with the girls. Besides you have the housework to get done on a Saturday. I think that’s enough staring at my body for now… go get started on the the ironing… and my bedroom needs cleaning and the bed made before I get back… and my bathroom needs to be cleaned, I made a bit of a mess in my rush.

Don’t be so stupid. As if I would go to all this trouble dressing up for you! And don’t even think about touching me.
Rick just called to say he’s in town, so I am rushing off to his hotel for the night.
I know it’s your night for your monthly release. But this is more important, I haven’t had a good fuck since Wednesday…. So you’ll just have to wait until next month now.
No, I am not releasing you tomorrow instead. I’ll need a lie in, and then I am off shopping before a night out with the girls. Besides you have the housework to get done on a Saturday. I think that’s enough staring at my body for now… go get started on the the ironing… and my bedroom needs cleaning and the bed made before I get back… and my bathroom needs to be cleaned, I made a bit of a mess in my rush.

(via chastewiddlesissy)

August 14
Is that you Rick? You’re home sooner than I expected… Robert just called, he had to come to town at the last minute and was hoping to catch up. I explained we had tickets to see your favourite band for your birthday. Turns out he likes them too; so you just lucked out… No meal out, no concert and no release I’m afraid. Don’t be silly… I could hardly tell him to come round after the concert… leave him all night on his own, we only catch up once a month. As if I am going to have time to tend to your release… he’ll be here in twenty minutes. You’ll just have to wait until next month… Now go and make yourself useful. Clean up the bathroom, put some nice music on for when he arrives and then take yourself into the study. I had been thoughtful enough to mark out a few verses from the Iliad, in Latin, for you to copy out… I thought it might help to keep you occupied and take your mind off the disappointment. I was going to let you copy it out ten times… But seeing as you’re acting so selfish, you can write it out twenty five times… So you might want to get started right away as that will take you over eight hours… And I want you finished in time to clean me up after Robert’s spent his load, you know how much he spurts!

Is that you Rick? You’re home sooner than I expected…
Robert just called, he had to come to town at the last minute and was hoping to catch up. I explained we had tickets to see your favourite band for your birthday. Turns out he likes them too; so you just lucked out… No meal out, no concert and no release I’m afraid.
Don’t be silly… I could hardly tell him to come round after the concert… leave him all night on his own, we only catch up once a month.
As if I am going to have time to tend to your release… he’ll be here in twenty minutes.
You’ll just have to wait until next month… Now go and make yourself useful. Clean up the bathroom, put some nice music on for when he arrives and then take yourself into the study. I had been thoughtful enough to mark out a few verses from the Iliad, in Latin, for you to copy out… I thought it might help to keep you occupied and take your mind off the disappointment.
I was going to let you copy it out ten times… But seeing as you’re acting so selfish, you can write it out twenty five times… So you might want to get started right away as that will take you over eight hours… And I want you finished in time to clean me up after Robert’s spent his load, you know how much he spurts!

(Source: wanktrance, via chastewiddlesissy)

August 9