Tuesday, January 16

Babysitter Roleplay Advice Please!

Thinking of doing a "babysitter" roleplay with my husband. Was interested in your thoughts on this particular genre. What would super turn you on?


Here are my initial thoughts.

I imagine he is a fourteen-year-old teenager, a little "too old" to have a babysitter. I am the twenty-one-year-old girl next door, 1950's style: sneakers, socks, skirt, blouse, sweater. I have been asked to babysit him for the weekend while his parents are out of town on a mini-vacation.

I am a very orderly person. My little overnight case is packed in a very exact fashion, everything in its place. On Saturday morning I notice that a pair of my panties are on the wrong side of the suitcase, and are folded a different way than I always fold them. Nothing else seems touched. It is only david and I in the house. I strongly suspect he has been very naughty with them!

I grab the panties and go down to the living room, yelling for david to join me. I hold out the panties with both hands at arm's length and ask him, "what is the meaning of this? Have you been into my suitcase?"


I imagine david blushes, stammers, looks at his feet and denies, denies, denies.

I give him a good hard slap across the face and tell him I know it was him and he should admit it. He again denies, but is starting to tear up. Another good hard slap across his face, and he breaks down crying, admits it, and apologizes.

I ask him what he did with them. He swears he only touched them and looked at them. I keep him there and quiz him on his motivation. "I don't know!" he wails.

"You've been a very, very bad boy," I scold. "You went into my room without permission, and then went through my things without permission in a sneaky fashion. You then lied to me about it when I confronted you. And, worst of all, you were being naughty with my underwear!"

"I wasn't!" he says, referring to the "being naughty" part.

"You certainly were! Fondling my underwear? That is very naughty!" He goes quiet. He is looking horribly embarrassed.

"Will you tell Mommy and Daddy?" he asks.

"No. This is between you and me, young man, unless you make it otherwise," I say.

"Thank you," he says, clearly relieved.

"But don't think you won't be punished," I added. "You'll get a good hard spanking and then I'll wash your mouth out for your lying."

"A... a... a... spanking...?" he says, shocked.

"A good hard spanking, right on your bare bottom," I add.

"B... b... bare bottom...?" he says, even more shocked.

"Bare bottom," I reiterate, "no more backtalking!"

"I'm too old for a spanking," he whines.

"You're not too old to misbehave, so you're not too old to be punished. And I warned you about your backtalk. After your mouth soaping we'll just keep that bar in your mouth while you go across my knee for another spanking. Care to backtalk me some more, young man? No, I thought not."


So that's my setup. You like???

In terms of activities I thought as follows.
  • I'll have him in his size too small tighty-wighty underpants. I'll make him take his pants right off and then have him stand in the corner to "think about his misbehaviour for a half an hour".
    • Question: should I undress him myself down to his underpants, or make him do it in front of me?
    • Would that be embarrassing for a "young lad" to be made to stand in the corner, in only his tighty-wighty underpants, in front of the cute young babysitter, waiting for his spanking? I imagine so.
    • Should I make him do the full half-hour, even just for roleplay?
    • Where should his hands go, at his sides or on his head?
  • When his time is up I'll grab him by the ear and march him over to the spanking chair with the wooden hairbrush placed on it, then sit and take him across my knee.
    • What do you think, should he be made to lower his underpants before going across my knee, should I lower them for him, or can he keep them up until he's across my knees?
    • What's the psychology of having him bare his penis to his babysitter prior to punishment?
    • If he's hard do I ignore it completely or scold him for it?
  • I'll lecture him and tell him this spanking is for sneaking into my room and going through my things without permission. Then I'll give him a good hard one with the hairbrush.
    • Should I warm him up gently with my hand and then build the intensity with the brush? A "real" angry babysitter would start right in with a punishment. Should I do that for realism?
  • I'll stand him up and take him by the ear to the bathroom. There I'll wash out his mouth with soap. Lots and lots of suds. I'll scold him for lying to me and tell him this is what will happen to him every time he lies to me.
    • Should I use a washcloth, or the bar of soap directly, or both?
    • Any special tips for memorable mouth soapings?
  • I'll make him hold the bar of soap in his mouth, take him across my knee, scold him for his back-talking and give him a hand spanking. Then the bar can come out and he may rinse.
    • We've had a bad experience once where I kept the bar in for too long (he was standing in the corner) and his mouth was sore all next day from mild caustic burns. Will try to limit the time the bar is in, but is there a better kind of soap that will damage him least?
  • Then I'll take him to his bedroom, make him lie face down on the bed across several pillows, and use the strap on him. I'll scold him for being "naughty" with my panties as I strap him.
    • Thinking just twenty or so, not to go overboard for realism. Is ok?
    • Should the strap be something I brought along with me to deal with naughty charges, or one I found in the basement, or one his parents told me to use on him if he misbehaved?
  • Afterwards I'll tell him he's taken his punishment, I'm satisfied, and he's now forgiven, and no reason for his parents to know anything about it. I'll give him a gentle and seductive kiss on the cheek.
  • I'll tell him to stay as he is. I'll fetch the cold cream to soothe his buns. When I come back, I'll rub it into his ass and thighs. I'll notice that the strap worked its way towards the insides of his thighs and rub there as well, brushing his balls.
  • When he reacts, I'll ask, horrified, "are you excited by this???"
  • I'll make him turn over so I can see his big erection. OMG! I'll giggle and say none of my panties are safe when he's in this state!
  • I'll ask if he masturbates? He'll lie and say no. I'll tell him that I won't be safe in this house unless he does. I'll make him do it in front of me to be sure it gets done.
    • Question: should I "encourage" him by giving him a little peakaboo at my tits?
Let me know what you think, and any suggestions!


159 comments:

  1. OMG Ms. Julie I love this scenario....I had a hot babysitter when I was young but alas I was too young to really get the full benefit!
    As to your questions...
    I think you should make him undress himself....slowly....telling him which article to remove next...
    I don't know about david but as a young boy, going through puberty, I would have been a little embarrassed and a little excited at the same time to be stripped down to just my underpants...
    And definitely for the full half hour....with the hands held on the head or behind the back...
    He should definitely have to stand in front of you and lower his underpants...then it's time for a few minutes of quiet time while you look it over....then a little laughter and small penis humiliation...
    You're doing this to punish a naughty boy so I think we can skip right to the hairbrush...
    My wife once put the soap in my mouth and used tape to keep it there....an awful 10 minutes that I thought would never end...she also made sure I couldn't see a clock so I couldn't tell how long I'd been there!!!
    Then take the soap out as you lead him to your room and then scold him and leave the panties out where he can see them...
    Then put the soap back in his mouth as he goes over your knee....let him know that if he drops the soap you'll start over!!!
    Take him back to his room as you planned but make him wait while you have to go get the strap....tell him you have to go home to get the strap that your Daddy used on you when you were naughty....
    20 should be fine but you can adjust the number based on how things are going...
    Then make him put on the panties, kneel and apologize, while there you could let him get a peek up your skirt!!!
    Then make him stand and masturbate for you....tell him you're thinking of inviting his friends in to see his red ass in the pretty panties....
    When he cums make him clean it up and put him to bed after....then invite some friends over and you can all have a good laugh at his expense....
    If my sitter had done this to me at 14 she would have owned me!!!!
    Love
    Kaaren

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  2. Julie, Before he is forgiven he should be made to hand wash the panties.
    “ I have no idea what you did with them! “ Standing naked in front of the sink, being spanked and scolded while still touching your panties. A great time to “notice” his erection.
    Have fun!
    Tom

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  3. I like your itinerary of activities just fine......besides.....that list is best coming from you anyway, but......

    personally, I would like it to come out afterwards somehow that it was the Dad who hired you who had been touching your panties, presumably while the Mom was going over her instructions and contact information, not David.

    I think that gives you a set-up for a very different line of questioning with David that could lead to all sorts of other things.

    Just my thought. All the best!

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    Replies
    1. Great idea, but I feel the boy should be punished for his own wrongdoing!

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  4. You should remove david's underwear and make him put on the panties he was playing with. You will see his erection and humiliate him by telling him he secretly wants to be spanked. You will brush Your hand across his hard pantied cock. You will pull his panties down and proceed to paddle his bare bottom across your lap with a long-handled bath brush. david is made to stand in the corner for 30 minutes with arms at his side. You tell him he needs to contemplate what a naughty pussy whipped boy he is. You ear march him to the bathroom and use a washcloth to soap his mouth for initially resisting the idea of getting a spanking. You then make david lie on the bed with two pillows underneath to raise his bare bottom. You retrieve one of david's own belts and proceed to administer a sound whipping with it. When through You notice david is hard again. You proceed to sit in a chair and part Your legs so david can see Your pantied pussy. You make him jack off while staring up Your skirt scolding him the whole time. david is required to cum in his hand and eat all of his own ejaculate. What a great way to start the weekend.

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    1. See, I'm not sure if I should have him put on the panties. It's the obvious move, but would the babysitter do that? Encourage his perversion like that? I need to maintain a "suspension of disbelief" so don;t want to get out of character at all. But worth discussing further...

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  5. Try ivory. It's a lye-based soap, which sounds scary, but the lye is used to create a soap from animal fats, whereas most bar "soaps" are non-fat based detergents. It's not necessarily "milder", but it's different than the others and worth a try.

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    1. Any 'soap' that has undergone 'saponification' has used lye ( sodium hydroxide ) not just Ivory. Also, lye is not derived from animal fat. Any natural soap, or soaps like Dove, etc. use lye in the saponification process.

      The attraction for kinky folks using Ivory for things like mouth soaping or enemas, is the belief that the lack of other color, fragrance, or moisturizing chemicals makes it 'safer'. So you're on the right track, but not for the reasons you stated. ;-)

      All the best!

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    2. Thanks! I guess it's the "sodium hydroxide" which can cause the caustic burns if in too long? Any kind of soap that does not do that? I would love to keep that bar in much longer, but don't want any residual burning discomfort as he reported that other time.

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    3. Active sodium hydroxide in a processed bar of soap should be absent once the saponification is complete. (Ivory insists that any trace of lye is long gone before anyone ever touches their soap.) So if you use something like Dove or Ivory, you should be fine. Just avoid swallowing or some poor fellow is going to be pooping his brains out later!

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    4. Ms Julie - here's a blog post about safe FLAVORED soaps to wash out david's mouth ( https://blogs.babycenter.com/mom_stories/04012013non-toxic-naughty-mouth-soap-teaches-kids-a-lesson/ ).

      Not knowing the timing of this scene, another site suggested using a small squirt bottle of apple cider vinegar and giving him a little squirt on the tongue ( http://www.circleofmoms.com/parenting-debates-hot-topics/washing-out-your-kids-mouth-with-soap-yes-or-no-726830 ).

      A sitter in the '50s would not have had the flavored soap, yet might have been familiar with the apple cider vinegar treatment - perhaps you could wet a cloth (or your undies!) with it and use that to wash his mouth out!

      Choices, choices! Good luck!

      -t.

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    5. Sounds too pleasant! It's the Ivory for him!

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  6. The scenario is more exciting if the young guy feels guilty but also if the baby sitter is a little sadistic and takes the opportunity.

    So for the first slap, you may ask david to approach and question him at length. Then you ask him to put his hands behind his back and you warn him that you are going to slap him because he continues to lie. He must not be taken by surprise but forced to accept the slap that will come (very humiliating). The slap must be strong and hurt him, it is not a joke. So he waits for the second with more apprehension.

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  7. An idea for corner time,
    After some mocking comments on his plump buttocks and how they exceed his tighty-wighties you explain to him that your parents have long imposed you, when you were his age, an infamous punishment and you have always wanted to know what it would look like with a boy, especially in front.
    You tell him his hands should go at his side but passing under his tighty-wighty underpants. Then he has to kneel until the belt of his underpants rise to his elbow crease. He must then straighten up in a prayer position his hands clasped to the height of the torax. With a little help from you, this simple gesture made his underwear goes up deep between his buttocks and on the front. He must keep 10 minutes this humiliating pose, painful and perfectly ridiculous.

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    1. You're mean! You JUST KNEW that I would have to test this out on myself, didn't you???? Well my pussy and bumhole got very abused in the process!!! My panties slid right into the slit of my pussy, and I had two puffy lips on either side! Cruel and unusual punishment. I LOVE it! Maybe after the two slaps, he is still not talking, so I make him stand like this until he does - I don't care how long it takes (but which ought to be pretty quick based on my own experience!)

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    2. You could not resist the temptation...

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    3. Ms Julie - I tried this too and, though uncomfortable in the crack and anal area, didn't hurt elsewhere because things in front just traveled up with the fabric. Perhaps my underwear ( https://www.jockey.com/catalog/product/jockey-seamfree-low-rise-brief ) is too stretchy?

      Any other guys try this and have results similar to mine?

      -t.

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    4. I made him try with his stretch cotton briefs, his hands at chin level. He started to beg me after 7 minutes of trot around the room (and yes, I had added a banana (not peeled) up his ass). I take note to show that to our guests at one of our forthcoming circus evenings.

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    5. Maybe tighter whiter undies?

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  8. ----o Question: should I undress him myself down to his underpants, or make him do it in front of me?
    Answer: Its always more embarrassing for the sitter to do it for him, makes him feel extra helpless and set the stage


    ----o Should I make him do the full half-hour, even just for roleplay?
    Answer: I would say time out with the panties he took around his knees you could even have your sister on the phone acting like you are talking about him with a friend



    ----o Where should his hands go, at his sides or on his head?

    Answer: Behind his head to make sure he does try playing with himself


    --- o What do you think, should he be made to lower his underpants before going across my knee, should I lower them for him, or can he keep them up until he's across my knees?

    Answer: Remove his panties and then use them as a gag for his spanking putting them in his mouth


    ---o If he's hard do I ignore it completely or scold him for it?

    Answer: I would scold him for it letting him know that isn't appropriate and his mother would be very angry with him,


    ---o Should I warm him up gently with my hand and then build the intensity with the brush? A "real" angry babysitter would start right in with a punishment. Should I do that for realism?

    Answer: I think a fun little warm with some teasing about his friends would think if they knew would be fun.

    ---o Should I use a washcloth, or the bar of soap directly, or both?

    Answer: I think a good soaping with a bar paying particular attention to the tongue
    Then a 2nd time out for about 5 minutes with the bar just sitting in with a final cleaning with a wash cloth


    • I'll make him turn over so I can see his big erection. OMG! I'll giggle and say none of my panties are safe when he's in this state!
    Answer: Since he can't behave in panties you should then produce some diapers and keep him in then for the rest of the weekend while he is out and maybe go out and get a couple baby bottles etc for him

    Extra tips: After the soaping and maybe even diapering I would end it with full on make over maybe your sister can come over to act as your friend with a sleep over party and carry on his embarrassment from there


    Emily

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    1. I love many of your ideas! But as I replied earlier in the comments, I need to maintain the suspension of disbelief and so need to channel what a real, strict, no-nonsense 1950s babysitter might do, and it's likely not further panty play or diapering!

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    2. You might want to get into the 1950s fashion with a poodle skirt and blouse

      Emily

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    3. for 1950s I believe with the movie grease you could always just have your sister over as suggested before and I think that could pass and he would have to do whatever you two said in servant mode after your punishment maybe have him write lines between requests etc. I think most kids of every generation tried to blackmail each other so they wouldn't get in trouble at one point or another.

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    4. Just me this time. It's a hubby-wife special discipline roleplay I have planned!

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  9. I would follow it up by taking him shopping wearing the panties and make him purchase his own while you and the sales lady teach him about the different styles

    Sarah

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    1. I think not! This sort of behaviour WAS NOT encouraged in the 50's!

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  10. Most of your ideas, as usual, are spot-on. I would add a couple of points for the spanking:

    1. I'd have him over your knee is his regular clothes at first (i.e., pants and underwear, or at least underwear). Take the pants (but not the underwear) down and start the spanking. Hand or hairbrush, either way, but warm him up a little. Even a mad babysitter might want to teach her young charge a lesson (see below).

    2. Increase the severity of the spanking (still over his underwear) until he's jumping around and pleading. At that point, you can say something along the lines of "Are you going to be a good boy? Are you going to behave and do what I say from now on?" Of course he will say yes. Then comes the kicker: "Hmm, we'll see. All right, say the following: 'I've been a very bad boy, and you should pull my panties down and give me a good spanking on my bare butt.'

    This presents him with a dilemma: does he obey and get a worse spanking, or disobey (at which point you of course would say "I thought so! you're still being a bad boy!" and continue with the spanking over his underwear until he gives in)? Either way, he's screwed.

    2. Not sure a babysitter would do this, but you might tie his hands for the spanking. Just to make sure he doesn't "get away".

    Anon C

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    1. Such a trad-off! I love the pulling of his undies down, exposing him, before going across the knee. But also like this! Maybe I should do as you say, and after he asks, then make him stand up and pull the down before coming back over my knee. Best of both worlds!

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  11. • I'll make him turn over so I can see his big erection. OMG! I'll giggle and say none of my panties are safe when he's in this state!

    I agree with Emily, above. If he can't be trusted as an adult, maybe he needs to be regressed to a baby. Furthermore, you are a BABY sitter, that would fit well. In diapers, his penis isn't a menace anymore, so you can finish to tease him making he drink a milk baby bottle while watch you self-masturbating (or just give him bottle in the mouth), and so make him go to bed with a pacifier in the mouth.

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  12. Goddess Gretchen17 January 2018 at 10:11

    You should incorporate diapers into the scene......

    Goddess Gretchen

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  13. Good idea for your story sure be real life learning experience when done with him and his ass punishment

    Another idea I think be you catch him peeking on you when changing in shower or bedroom you of course embraass grab him by ear scolding him calling him pervert need good old fashion spankings hard over your lap order him strip naked or will tell his mom when get home only way won’t if he agree to spanking from you

    Another one idea you catch him masterbaue to one of your panties but then noticed he has few other years ur panties you thought you lost make him shower. Come to you wearing panties as he will be getting a spanking wearing them if cum in them you will place in his mouth for 1 hours if good boy he can kiss your ass play with your pussy

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    1. Got caught playing with myself, looking at spanking magazines, my girlfriend at the time, now my wife. I thought I was alone in the apartment, she caught me on the toilet naked, stroking. I was soon over her lap in the kitchen and my bottom feeling the sting of a wooden spoon. Of course the neighbors heard, one lady a couple of days later came over with a large paddle, covers more area, quicker results, my girlfriend smiled, thanked her, and turned to me, prior to bed young man.

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    2. Thanks mike!

      anony: too bad she did not use that paddle on you then and there. Seemed like a clear invitation to do so, preceded by a "demonstration" of your naughtiness, to completion in front of her!

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  14. if you incorporate diapers into the scene like Goddess Gretchen says you should give him a couple of suppository as this will ensure a mess and he won't be able to hold it in or know when it will happen.

    April

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    1. Trying to stick with the bay sitter theme and keep it more "realistic!"

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  15. if diapers are on the menu try using the fancy abdl premium diapers from rearz or abdl rearz has a princess design that is ultra sissy

    http://www.cooshietooshiez.com/product-p/pp12.htm

    Jenny

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    1. I'll bear that in mind for future scenes!

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  16. Oh my...

    I’m having trouble visualizing the immediate, angry response. I picture the babysitter more uncertain about her approach...knowing exactly that the naughty boy handled her panties, but more feeling out how to deal with it.

    Perhaps bringing out her refolded panties and setting them out on the table and calling the naughty boy for a discussion.

    She’s in complete control and he’s squirming, immediately knowing he’s caught.

    “Should I call your mom to discuss what you did or do you think we can sort things out on our own?”...telephone in hand.

    “Tell me...why were you interested in my panties?”

    “What did you do to them?”

    “You knew it was wrong to touch my things”

    “You know you must be punished?”

    “How does your mom punish you? Be honest with me. I will come up with an excuse to ask her...”

    I envision a painfully embarrassing discussion where his punishment is figured out together...then you send him to the corner for a full 1/2 hour to think about it before it begins.

    The start might be lines...”I will never touch a woman’s panties without permission”

    Then the spanking. Yes, immediately the brush...she’s not an experienced spanker!...but she has him wear or have the panties in his mouth as a reminder of the reason for the spanking.....

    I’ve done poorly responding to your questions and provided an unsolicited alternate narrative! Sorry!

    peter peter

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    1. Love it! I love the slow torture aspect. But there is an appeal to the strict angry babysitter also... decisions, decisions!

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  17. When the wife spanks me i am ussally hard then she beats me till it goes away then teases me a little and it comes back . Then she beats me til it goes away . She keeps that up till i am to sore to get hard again. Or she makes me masturbate first whitch i absolutely hate and she knows it.

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  18. Love the setup. I'd like to offer the following adjustments similar to peter peter's.

    1) He wasn't playing with your clean panties. He was playing with the used ones you put in the hamper. Perhaps they're on the ground as he rushed out of the room when you suddenly came in.

    2) You put 2 and 2 together as you wonder why he was in your room, why he rushed out, and how did your panties end up on the ground when you're very tidy and put them in the hamper. As a result you're embarrassed and hence angry.

    3) You ask him why he refused to talk. Even after a slap or two. He might say he doesn't know but you know he's lying.

    4) You have him remove his pants and stand in the corner until he's ready to talk. Full half hour! Hands on top of head!

    5) Times up and he's ready to talk. He tells you he was playing with them but you keep probing and it turns out he was smelling them!

    6) You look disgusted at him at this confession. More embarrassing questions. Was he going to masturbate. How often does he. If he has a noticeable erection you have him remove his underpants and stand in front of you bare as you continue the questions. During which you admonish him for getting excited talking about disgusting and perverted things. This is the 50s after all and people are not as open minded!

    7) Time for a spanking. Since he liked smelling your panties you put them on his head with the special area right over his nose!

    8) Hard spanking since babysitter is inexperienced. Also goal is to remove the erection.

    9) Afterwards, if he still has an erection you need stronger measures. The strap. But not lying over the bed since that gives him an opportunity to rub it out. Standing with his hands on head. While you lecture him.

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    Replies
    1. Terrific alternate ideas! Thank you! So many decisions to make!

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  19. OMFG! Please add some baby bottle and pacifier! PLEASE!

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  20. What's the psychology of having him bare his penis to his babysitter prior to punishment?
    If he's hard do I ignore it completely or scold him for it?
    Suggestion....
    That is a punishment for being a pervert so his bottom and penis must be bare, any modesty must be ignored. It is good to show him that, in these circumstances, his pee-pee doesn't mean anything (in others either, besides, as far as you are concerned! - You are still a virgin but he absolutely does not need to know it, such a baby...). It doesn't matter if you see it or touch it. You are definitely not interested in it. There is nothing sexual in this punishment. It doesn't excite any desire in you. It's just punishment. Very humiliating, certainly, but nothing to do with sex.
    You take your time to bare his penis, you notice he is hard and ask him if he thinks it is smart to react like that. You scold him and tell him to calm down. You tell him he is so funny with his throbbing dickie (OMG!).You warn him that you are free to do whatever you want with his penis and testes and that there is no doubt that you will make him go limp before starting spanking. This will take the time that is needed.
    You hit one of his nuts with a flick of a finger, he makes one tiny little cry. You find it fun and vaguely exciting...

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    1. You're really getting into this! Yay! I like the dialogue here.

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  21. Side question, Do you ever do orgasm torture? I.e. give him 3,4 etc orgasms? Or make him cum in a time limit or else? Or give him one then keep going for a 2nd?

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    1. He does not seem capable of more than one at a time, but yes to the time limit, with a strict strapping if he misses the mark and then he has to start all over again with it limp. And yes, I did try continuing to rub after the orgasm. Torturous and safe! Perfect!

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  22. And about his teen asshole? Nothing planned ?
    Maybe he could be so scared that he would poop in his pants.

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    1. 1950's innocent babysitter! So NO!

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    2. Furthermore, a difficult fictional character for david. Should be well trained to be synchronous !

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    3. He can do "naughty guilty little boy" well!

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  23. Just take off your sneakers, bare his bottom and bend him over your knees. Then whack him as hard as you can with your sneakers.

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    1. Oh I like that better than the hairbrush! More "intimate".

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  24. I'd do both. You need the brush in there with the sneaker sole as part of the warm up. "Off my lap, kneel and untie my sneaker...long pause...remove it and hand it to me....pause...get back over my lap. Good call from sneaker person, much more intimate and befitting of that scene!

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    1. I don't know... smacks of fetishistic shoe/foot worship. NOT the thing my 50's babysitter would be into... But good thought!

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  25. Or incorporate the sneaker with my idea above: first a spanking with the sneaker, over his undies, then after he's been made to admit he's a bad boy and needs a more thorough punishment, with a hairbrush on the bare.

    To answer your comment above, Julie, speaking as a sub (well, switch, but sub for our purposes here...) I find it much "better" to stay over the woman's knee and have her pull the underwear down. Just gives me that much more of a feeling of helplessness toward the coming bare-bottomed spanking vs. being made to take them down myself.

    Anon C

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    1. By then the private parts are not on show! Boo.

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  26. brett has some great comments that he emailed me. I'll share them as replies to this comment.

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    1. "I'll have him in his size too small tighty-wighty underpants. I'll make him take his pants right off and then have him stand in the corner to "think about his misbehaviour for a half an hour".
      Question: should I undress him myself down to his underpants, or make him do it in front of me?"

      Being undressed is much more like being treated as a child. If I was sneaking a look at the babysitter's panties, it's because at 14-years-old, I am now fantasizing about girls all the time, and I want them to be attracted to me. Of course, it's completely unrealistic that a young woman 7 years older than I am is going to be interested in me, but that hasn't stopped me from dreaming of the smart-looking 21-year-old girl next door. I was a thousand percent against her being my babysitter, but my parents are such dicks. If only she could see me as being well advanced beyond my years and worthy of her attention. Her undressing me for punishment is several light years from the attention I was hoping for.

      "Would that be embarrassing for a "young lad" to be made to stand in the corner, in only his tighty-wighty underpants, in front of the cute young babysitter, waiting for his spanking? I imagine so."

      You imagine right. As I explained, age regression, or even anything that shows I'm a boy and not a man, is a painful defeat as far as how I wish to be seen. Everyone knows that corner-time is for small children who have misbehaved. I wouldn't believe it was actually happening, that my BABYsitter is punishing me in the most embarrassing ways she can dream up. Stripped to my underpants? This is NOT how a teenager should be treated but, unfortunately, I think my parents would probably approve. So I'm forced to stand in the corner is abject disgrace.

      "Should I make him do the full half-hour, even just for roleplay?"

      Unfortunately, it's going to have to be the full half-hour. Just like for the rest of the punishment, the closer roleplay is to reality, the more powerful it becomes. When I imagine these kinds of scenes, I don't want anything to interrupt or distract from what is being enacted. The whole point is to experience it as reality, not as play. We can't go back and make it real, but that's what motivates the play. If we could get in a time machine, and know that when we arrive at our destination in the past, all the forces and conditions will be in place for this authentic interaction, would we go? It's a scary ride, but I'm in line to buy my ticket.

      "Where should his hands go, at his sides or on his head?"

      I have no experience with this, so without any personal associations involved, hands at the sides seems realistic and more natural. I think either way must be equally humbling, but hands on sides may allow the naughty one to get their nose closer to the actual corner. The important thing is obedience, so however she demands it to be, that is the position and posture that must be adopted and maintained.

      "When his time is up I'll grab him by the ear and march him over to the spanking chair with the wooden hairbrush placed on it, then sit and take him across my knee.
      What do you think, should he be made to lower his underpants before going across my knee, should I lower them for him, or can he keep them up until he's across my knees?"

      You taking them down is a stronger demonstration of you taking the active role in punishment. If a little boy is getting a spanking from his mommy, she doesn't wait for or need any assistance from him. She simply lowers his underpants or does whatever she needs to do to get on with the task she is in charge of and executing to her specifications. He is merely a helpless object to be acted upon. Such is the dominant nature of this babysitter.

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    2. "What's the psychology of having him bare his penis to his babysitter prior to punishment?"

      I'm not a psychologist, but I can imagine the psychological effect. For starters, it's about context. Why is my penis bare? It is certainly not because my babysitter is considering having sex with me. It is only bare because my pants have had to be taken down for a spanking. It stands there only to mock the position I am in. Oh look, isn't he such a big boy now. He has a penis. But at 14, even standing at full attention, it is not an impressive sight by any means. Displayed in such blatant fashion is a boy who is clearly inadequate for any adult relationship with a young woman. His babysitter intentionally exposed him like this, so he can only imagine she is simply amused by the spectacle.

      "If he's hard do I ignore it completely or scold him for it?"

      It's a cruel result of nature, but in his moment of shame and disgrace, standing exposed before a girl who attracts him so strongly, his penis is erect. He would give anything for it not to be so. What he wants is to be cool and detached, not to be seen as a horny little geek begging for attention. His penis is exposed, and he can't control how it exposes his feelings. What is it telling his babysitter? That he has a hopeless little puppy dog crush on her? That he's been masturbating to thoughts of the girl next door? Isn't it obvious that, if his dreams could somehow become reality, he couldn't last a minute before he blows it with his small impotent explosion? This is a moment of mortification for him, so how you handle it is dependent on how you want to exploit it. Ignoring it completely is either a way of saying it isn't worthy of mention, or that his erection is irrelevant to the punishment, or possibly that you are out of kindness sparing him further embarrassment. I find all of those reasons to be humiliating---different flavors and for different reasons. Scolding is blaming him for something he can't control, but if the intent is to enhance feelings of embarrassment, it's a good option. You can assure him that the hairbrush will be quickly taking that boner away. Another possibility is a little teasing, something to validate his fears.

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    3. "I'll lecture him and tell him this spanking is for sneaking into my room and going through my things without permission. Then I'll give him a good hard one with the hairbrush.
      Should I warm him up gently with my hand and then build the intensity with the brush? A "real" angry babysitter would start right in with a punishment. Should I do that for realism?"

      I don't know that realism is the same for everyone. If what feels real is a reenactment of punishment as personally experienced in the past, it really depends on that past and the way their disciplinarian spanked. The sense of realism might not be from personal experience, but from how one has been exposed to the idea of corporal punishment through some form of historical accounting or entertainment. For me, I never experienced anything like a warm-up or building of intensity. It was simply supposed to be maximum bad from start to finish, though maximum punishment was moderated to what would be acceptable and appropriate for a boy, not an adult criminal under some brutal, merciless regime. It just so happened that an acceptable spanking could be something you sincerely wished would never happen again.

      I remember years ago reading an accounting by a man of how he was, as a boy, spanked with a hairbrush by his mother. It really stuck with me. In great detail he described the experience of being spanked long rather than hard. The spanks were given so that at first they were stinging but not really very painful. To the uninitiated it could foster a temporary sense of hope and relief. The entire punishment would consist of these moderately sharp but restrained spanks with the hard, heavy flat of the implacable wooden back of his mother's brush. What made the spanking so memorable and effective was the relatively long build-up of fire on the bare buttocks, the same tender spots spanked again and again and again in a brisk but easy manner. It was a build up of intense pain. Before long, he was unable to keep still, his hips squirming in time with the hairbrush, and then the wriggling movements more desperate. There was no relent in the brush as it continued to scold two spots that must have by this time been shining fire-engine red but not a sign yet for stopping. As you might imagine, feet began to kick, legs to thresh, and there was a higher pitch to the pleading and promises being made. I think we would have had to be there to appreciate the extent of it, but the spanking continued like this until his disciplinarian was satisfied with the result, and the result was a bottom on fire. A different approach, but genuinely and agonizingly real.

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    4. "I'll stand him up and take him by the ear to the bathroom. There I'll wash out his mouth with soap. Lots and lots of suds. I'll scold him for lying to me and tell him this is what will happen to him every time he lies to me.
      Should I use a washcloth, or the bar of soap directly, or both?
      Any special tips for memorable mouth soapings?"

      I've never experienced mouth-soaping or thought much about it other than it must taste dreadful. Gag! And I've heard it takes a long time to get that taste out of your mouth. As a well-known child's punishment, it does pack the right flavor of humiliation. Not sure why, but I would vote for scrubbing his tongue with a soapy washcloth. I think there's something more controlling and "mommyish" about that. I certainly wouldn't like it one bit, so it would be a genuine punishment. Does anyone want soap in their mouth?

      Why the soaping? Well, I think this 1950s babysitter is a natural domestic disciplinarian. She knows little to nothing about kinky BDSM, which at the time was a world deep underground and not something a wholesome girl next door would have been exposed to. If she was exposed to it, though, she would find an affinity for at least some of the common practices. No, her natural instinct is to simply take control of this teenaged boy in a manner with which she is familiar, that being 1950's maternal authority. The question is how far will she take it. She uses mouth-soaping as a punishment because her child lying to her is an offense she simply will not tolerate. It's a clear rebellion to undermine her authority while denying her her right to know everything. There's a feeling when you're under the thumb of such a strict authority figure that makes you more vulnerable than anywhere else. Complete and total transparency is central to the helplessness felt. No secret can be held. No lie can go unpunished. What could be more symbolically straightforward than soap-scrubbing the lies clean from the offending tongue? A foaming mouthful of wet bitter suds is the clearest message that lying to her is unacceptable, and I believe the threat of being marched to the bathroom will truly influence him to be truthful with her despite the strong temptation little boys have to protect themselves with a lie.

      "Then I'll take him to his bedroom, make him lie face down on the bed across several pillows, and use the strap on him. I'll scold him for being "naughty" with my panties as I strap him.
      Thinking just twenty or so, not to go overboard for realism. Is ok?"

      I hate that position of submission over pillows, posed like a poster boy for traditional domestic discipline. If you have him slide his hands, palms up, under the pillows, and tell him you had better not see those hands during his strapping, it should ensure he both stays in place and is prevented from protecting his upturned bare bottom.

      Would twenty good sharp licks with the strap on bare skin still tender and burning from a hairbrush spanking be realistically punitive? I believe so. Well before twenty is reached, I see a teenage boy rocking those pillows, kicking like a gold-metal swimmer, his voice pitched to a frequency only his babysitter can hear. Her scolding will shine the light on why he's having his bottom disciplined to the color of ripe cherries, and his face will reflect the red of shame at having been naughty with her panties. If his babysitter was more aware of fetish psychology, she might have him wearing those panties because, for all intents and purposes, he's her little girl now.

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    5. "Should the strap be something I brought along with me to deal with naughty charges, or one I found in the basement, or one his parents told me to use on him if he misbehaved?"

      That's an interesting aspect to consider. Where did she get the strap? The hairbrush could have been hers for brushing hair, but the strap is strictly an old-fashioned spanking implement. The way I like to imagine the scenario is that this is a special event that grew spontaneously out of the circumstances presented to the characters involved. The babysitter might like the idea of punishing her charges, but that isn't a realistic option in this place and time. At least it wasn't in mine. Babysitters were not given that authority, but that makes this particular scene all the more shocking and embarrassing. She didn't anticipate that a teenage boy would be sneaking into her personal things, but she is seizing on the advantage it offers her. His fervent hope is that no one will find out about his perving, placing him firmly in her clutches. Living next door, she knows this boy gets the strap from his parents, and the idea of that is amusing and exciting to her. She went exploring in the basement and was pleased to find the spanking strap hanging from a peg on the wall. She held it to admire how supple and worn the old strip of leather felt in her hand, possibly a draconian family heirloom, and knowing that to take her place in line in upholding a tradition of generations, she is going to be able to painfully tan the hide of a tight young bare behind. I can just imagine the embarrassment of the boy when he sees the strap his parents use on him in the hands of his babysitter. Does she know they use it on him? This is probably about the time she makes sure he knows that she knows everything.

      "Afterwards I'll tell him he's taken his punishment, I'm satisfied, and he's now forgiven, and no reason for his parents to know anything about it. I'll give him a gentle and seductive kiss on the cheek."

      His embarrassment must be smothering him now. He can't even look at her, but she's so sweet and nurturing it puts a spell on him regardless. To be forgiven by her is like forgiveness from god. Yes, she's a Goddess to him, a benevolent deity protecting him from the harsh judgment of his parents. Her seduction, the delicate kiss on his cheek, will haunt his dreams with a yearning for what can be but an empty promise.

      "I'll tell him to stay as he is. I'll fetch the cold cream to soothe his buns. When I come back, I'll rub it into his ass and thighs. I'll notice that the strap worked its way towards the insides of his thighs and rub there as well, brushing his balls.
      When he reacts, I'll ask, horrified, "are you excited by this???"
      I'll make him turn over so I can see his big erection. OMG! I'll giggle and say none of my panties are safe when he's in this state!
      I'll ask if he masturbates? He'll lie and say no. I'll tell him that I won't be safe in this house unless he does. I'll make him do it in front of me to be sure it gets done.
      Question: should I "encourage" him by giving him a little peakaboo at my tits?

      You're becoming the babysitter of his dreams. Your power over him is immense. He is starving for any scrap you will throw him. He still burns where you touched him with the cream and the electricity of your bare hand. He's never been this close to a woman. You're so close now you're in his blood. The tiniest peak of forbidden fruit could turn him to jelly. Enjoy your power. :)

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    6. Brett's got it right. One other idea for the strap would be to just get a belt from the closet and use that. It will be lighter than the strap, so you'd probably want to do 40 or so licks instead of 20, but on the other hand it would add a further dose of realism to your 1950's scene, plus be a slight change of pace.

      - Anon C

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    7. Somehow I don't picture the babysitter with a belt. I think a "Mom friendly" punishment strap hanging in the hall closet.

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  27. I also received a lovely story inspired by my roleplay musings from a certain "harry". Here it is below.

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    1. "Have you finished your bath?" Zoe called up the stairs.

      "Yeah… I'm in bed," replied Tim.

      Zoe was not convinced. She had been babysitting Tim for years, and knew that he hated taking a bath before bed. It wouldn't be the first time he had tried to get out of it, and she'd warned him about it last week and the week before. She trudged up the stairs and poked her head around Tim's bedroom door. He was tucked up in bed, reading, with a butter-wouldn't-melt expression on his face, which only raised Zoe's suspicions further. He was eighteen, but acted much younger sometimes, and his parents still felt that he needed supervision, and had given Zoe permission to spank him if necessary. He'd been in a troublesome mood all night, and she'd already had to threaten him with just such a spanking once.

      "Are you sure you've taken your bath, Tim?" she asked.

      "Yes, definitely Zoe, I promise," he replied earnestly.

      "You promise? Well in that case, I hope you don't mind if I just go and check if the towels are damp at all?"

      She waited for a reply, but none came.

      "… and if you've been lying to me, you can expect the hiding of your life when I get back," and with that she turned on her heel, and headed for the bathroom. When she got there, she found exactly what she had expected to find. Two towels neatly folded on the rack (Tim would never leave them like that) and bone dry. Zoe was angry, and disappointed. She knew Tim misbehaved, and would try and persuade her he didn't need to do chores, or take a bath, but he had never lied to her before.

      Perhaps she should have spanked him earlier when she'd threatened it… she had only done so a handful of times before, and it usually got through to him. She knew she let him get away with too much. This was really the last straw though, and she wouldn't make the same mistake again. With a heavy heart, she realized it was time to teach Tim a lesson he wouldn't forget. She steeled herself, and walked back to the bedroom, holding the tell-tale towel.

      "Totally dry. Can you explain that Tim?" Zoe asked. There was no response. "I think it's time you told me the truth, Tim," she continued, fixing him with a stare.

      "I am telling the truth, I promise. I did have my bath."

      Zoe's heart sank into her feet, and her face dropped. Any reservations she might have had about punishing Tim disappeared and she marched over to the side of the bed. In one quick motion she yanked back the covers, sat down on the edge of the bed, and flipped Tim over her knee. Before he had time to think, she had landed 5 quick hard smacks on the seat of his pyjamas.

      "I've had just about enough of your behaviour tonight," she said, punctuating each word with another hard spank to Tim's bottom. "I told you three times to take your bath, and I know for a fact that you haven't." More smacks, aimed at the base of his bum and the tops of his thighs. "You've been acting out all night, and now you've disobeyed me again. I promised you the spanking of your life and that's exactly what you're going to get." And then, with a quiet determination, Zoe set about giving Tim the spanking he deserved, her palm bouncing off his blue pyjama bottoms again and again, while he wriggled and complained underneath her.

      After what must have been 5 full minutes Zoe paused for breath. "You know, I really don't think I'm getting the message through here," she said, as much to herself as anything. "Up," she ordered Tim, and he complied. She spun him by his arm and marched him to the wall, pressing his nose up against it: "don't move an inch." She disappeared into the bathroom, leaving Tim wondering what was about to happen.

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    2. A few moments later she returned, brandishing the short, zebrawood bathbrush which Tim was supposed to use to scrub his back. "This is bone dry too… let's see if we can't do something useful with it at least," said Zoe, and she took hold of Tim's arm again, dragging him towards the bed, and back down across her knees. She raised her arm, and brought the flat side of the brush down on Tim's butt with a loud pop. His reaction was immediate – he yelped with pain, and his hand shot back to protect his already sore bottom.

      "That's better," said Zoe, as she caught his hand and pinned it to his back, continuing her assault on his pyjama-clad bottom with renewed vigour. Pop, pop, pop. The sound echoed out as Zoe alternated firm swats on each of Tim's buttocks. After a few dozen solid smacks, Tim was more compliant, and he lay whimpering gently over her knees.

      "OK Tim," she said, releasing his hand, "that was for disobeying me, and not taking your bath when you were supposed to," she said gently.

      "Sorry Zoe," he muttered and started scrabbling to his knees. He was stopped by Zoe's firm hand planted in the small of his back.

      "Not so fast young man. We still haven't dealt with the more serious offence of lying to me." Even saying it made Zoe upset and angry. "For that I need you to really get the point, so these are coming down."

      She transferred the bathbrush to her left hand, hooked her right hand into the waistband of Tim's pyjamas and yanked them roughly over his already-sore bottom. They bunched at his knees, and he let out a wail of protest.

      "Quiet now," she said crossly, "you'll only make it worse for yourself," emphasising the point with a few open-handed slaps to his bare thighs. Tim quietened down. Zoe took a breath, resting her right palm the seat of Tim's briefs. She could see a slight glow of pink through the white cotton, and two clear palm prints on his thighs from her most recent smacks.

      "Now Tim," she said, with stern resolve, "acting out, and misbehaving, and even disobeying me is one thing. I threatened you with a spanking, and that's exactly what you got. But lying to me, and promising when you know you're not telling the truth, is really much worse. I'm going to give you probably the hardest spanking you've ever had right now. It's going to hurt a lot, and the next few minutes aren't going to be much fun for either of us. I want you to spend that time thinking about exactly why it's important to tell the truth, and how much you've hurt and disappointed me by lying."

      Zoe transferred the bathbrush back to her right hand, and proceeded to give Tim the most comprehensive butt-blistering she could muster. Slowly at first, but with an even rhythm, and building in pace. The brush rained down on Tim's underwear-clad bottom over and over, dozens and dozens of times. Her strokes weren't hard at first, but grew in intensity as the punishment progressed. She wanted to keep Tim in pain and discomfort for as long as possible – to keep him alert, and thinking about his misdeeds, but contrite.

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    3. Zoe remembered a spanking she had received from her mother when she'd once lied about something – the rhythmic hairbrush strokes which built in speed and intensity to an unending crescendo of stinging pain. She had lain across her mothers lap sobbing as her bare bottom grew redder and redder, and she had never lied again. She knew she had to teach Tim the same lesson. With a heavy heart, she slipped her fingers inside the leg apertures of his undies, and slid them quickly up into his butt crack – first one side, then the other. Her next stroke landed squarely on Tim's bare butt with a loud slap.

      "NO, OW, stop please," he pleaded.

      "We'll stop when I'm good and ready, and not a second before," she said without breaking stride. The flat, heavy brush was really making an impression on Tim's bare bottom now, and there was a livid red patch at the crown of each of his butt cheeks. Tim squirmed again, trying to maneuver himself off her lap and away from the stinging swats. She took hold of his bunched undies with her left hand, and hoisted him higher onto her lap, hooking her right leg over his and pinning him firmly in place. Tim winced as the wedgie pulled his pants tightly over his penis and balls, which were now pressed against Zoe's left thigh.

      Zoe renewed her assault with the brush. "I hope this is getting through to you young man," she said. Each word was marked with a swat to the same place on Tim's left buttock. "Because I can keep doing this all night:" this sentence was punctuated with repeated swats to his right cheek. "If you want to act like a naughty little boy even though you're a teenager:" back to his left cheek. "Then I'm very happy to treat you like a naughty little boy:" more swats on his right butt cheek. "Do you understand," she asked angrily, adding a flurry of swats to both buttocks.

      "Yes," Tim said quietly. He was crying now. Zoe had a pang of pity for him, but resolved to follow through with her plan in its entirety. Half-measures clearly just didn't work with Tim. She wanted to make sure that he felt fully punished, and embarrassed, and that he wouldn't repeat this behaviour in a hurry. She briefly rubbed the bottom of his bum – bright red, with deep purple arcs where the brush had really hit home. She swatted him once with the palm of her hand. "Up," she commanded.

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    4. Tim stood up. She grabbed his arm and marched him back to the wall, shuffling with his PJs at half-mast. She reached and grabbed a large hardback book from the bookshelf, and dropped it on the floor about a foot from the wall. "Kneel down," she ordered and pointed to the book. Tim kneeled on the hard surface of the book. "Feet off the floor," said Zoe, and she placed a hand on the back of his head and pushed his nose towards the wall. As she did so, she produced a quarter from her pocket, and placed it on the wall, so that it was pinned in place by the tip of Tim's nose. She grabbed his arms, and folded them behind his back, each hand gripping the opposite elbow.

      "Stay right there young man until I come back," said Zoe. "Keep your hands folded behind your back, your feet off the floor and your nose against the wall. I don't want to have to look at you for the next five minutes. And if that quarter falls down, you're going right back over my knee, do you understand?"

      Tim said that he did. Zoe briefly surveyed him – bright red and purple weals clearly visible below his white undies, which were awkwardly bunched up in his butt crack, and pulling tightly and uncomfortably on his balls. Zoe turned and walked out of the room, leaving the door open so she could keep an eye on him. She would happily have left him like that for half an hour, but she couldn't spend all night punishing him… she had college coursework to finish herself, so five minutes would have to do. While Tim settled into his very uncomfortable timeout, Zoe went and got herself a glass of water, and checked her email, before busying herself getting the next phase of Tim's punishment ready.

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    5. When she was ready, she glanced at her watch. It had been closer to ten minutes. No harm there. She went back to the bedroom, and Tim was still obediently in position, with the quarter still held in place by his nose.

      "Right. Your behaviour tonight shows exactly why you still need a babysitter, Tim. If you can't be trusted to take a bath then I'm going to have to make sure you clean yourself up myself. I wish I didn't have to do this, but I'm not getting into trouble myself because you're not washed, so, on your feet young man." She pinched his ear, and twisted roughly, lifting so he had to rise to his feet. "Quick march," she ordered, and turned and led him by the ear out of the bedroom and down the hall to the bathroom.

      Laid out on the sink were a small white face flannel, and a small still-wrapped bar of hotel soap. Zoe laid a towel on the floor and manuevered Tim in front of the sink, facing her. "Arms up in the air," she ordered him. He complied, and she grabbed his t-shirt and lifted it over his head and off, leaving him in his white undies with his PJ bottoms still bunched at his ankles. She turned to to the sink, unwrapped the soap, and ran it under the water. "Now, first of all, little boys who lie get their mouths washed out with soap and water. Hands folded behind your back, and don't move them please." She rubbed the soap vigorously between her hands and the flannel, until there was a mass of soapy suds, then turned back to Tim. "Open," she ordered. Tim shook his head, keeping his mouth firmly shut. "OPEN your mouth Tim, I won't ask you again," said Zoe more firmly, and pushed the soapy washcloth towards his still closed mouth. He turned his head to the side, away from the soap. "I'm going to count to three Tim. One… two…" Reluctantly Tim opened his mouth a tiny fraction. Zoe pushed the soapy cloth in, but almost immediately Tim coughed and spat it back out.

      Zoe's reaction was immediate. With one soapy hand, she slapped Tim hard on the cheek. "HOW DARE YOU. You will obey me immediately, or we will go back into the bedroom right now and start again from scratch. Do you understand?" Tim hesitated for a second, and Zoe brought her hand down across his cheek again, hard. "DO YOU UNDERSTAND?" Tim nodded quickly, shocked by the severity of her response. "Now kneel down, head back and open your mouth, WIDE." Tim complied this time. Zoe wrapped the cloth around the three fingers of her right hand, made sure it was extra soapy and, grabbing the back of Tim's hair to make sure his mouth was good and wide, she used the pads of those fingers to thoroughly scrub his tongue, and the roof and sides of his mouth with the soapy washcloth. Once she'd thoroughly coated the inside of his mouth, she lathered up again and repeated the motion, pushing the washcloth right back along Tim's tongue so he nearly gagged.

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    6. When she was finished Tim's mouth was full of foam and saliva. "OK, Tim. Stand up, rinse out, and then it's time to get you washed and clean." Tim stood and rinsed his mouth in the sink, whilst Zoe lathered up the washcloth again. "Hands on head, and step out of those PJ bottoms," she barked, and Tim obeyed. With the soapy washcloth, Zoe scrubbed his armpits hard, one and then the other. When Tim whimpered at her vigorous scrubbing, she paused momentarily, looked him in the eye, and said, "one more noise out of you and this soap will go back in your mouth."

      She rinsed and lathered the washcloth again, and scrubbed Tim's chest, neck and back, before hooking her fingers into the waistband of his undies and unceremoniously yanking them down to his feet. She lathered up again and roughly scrubbed his balls, penis and ass. She was particularly vigorous scrubbing between his buttocks, and even pushed two soapy fingers quite far up his ass, to embarrass him more than anything else. By the time she was finished Tim was, involuntarily, fully erect.

      "Oh no. Ah aa… I'm not having any of that nonsense. We're getting rid of that thing quick smart." She turned him to face the bathroom sink, and grabbed his erect penis in one soapy hand. With about two or three quick strokes, she quickly brought him to an embarrassing orgasm.

      Tim shuddered as he came, but Zoe didn't miss a beat, continuing to soap his cock, balls and legs as before. Then she grabbed a fresh towel, and vigorously dried him down.

      When she was finished, and Tim was clean, and pink from the scrubbing, she turned him around and pressed his nose to the bathroom wall. "Right," she said. "You can have another 5 minutes to think about what you've been up to. Legs apart and hands folded behind your back." And with that she left the bathroom, switching off the light and leaving Tim in the dark.

      When she returned to the bathroom Tim was still standing with his nose pressed to the wall and his legs apart. Looking down, Zoe could see his penis was getting semi erect. She reached down and grabbed it, not gently, and it twitched under her touch.

      "My my we are getting excited tonight," she said with a smile. "I think I should probably take this opportunity to knock that on the head as well – we don't want you getting distracted by those thoughts."

      Zoe grabbed Tim by the ear and turned him back to the sink. She took a grip of his penis and as it firmed in her hand she rhythmically stroked him to another climax. She was still angry and her action was not gentle. She wanted Tim to understand that excessive masturbating wasn't actually as fun as he thought it was. This climax took longer than the last, but not by much, and there were only a few drops of cum. When he was finished, Zoe grabbed his ear and turned him back to the wall, pressing his head into it. "I'll be back in five minutes to try for another one," she said, and left the bathroom, turning out the light.

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    7. When Zoe returned, Tim's penis seemed fully limp, but she wasn't letting him get away that easily. She turned him to face the sink, and massaged his penis to a semi erect state. Fearing it would be harder to manipulate him to an orgasm directly, she went and retrieved her vibrator from her handbag. Returning to the bathroom, she held it under the head of Tim's penis. In a few moments he shuddered and his knees buckled. A single drop of cum beaded on the head of his penis.

      "What do you think, Tim? Can we manage one more?"

      "No ma'am," Tim replied.

      "Oh I think we probably can," said Zoe, setting the timer for another 5 minutes and pressing Tim's nose back against the wall.

      Zoe returned to the bathroom 5 minutes later and repeated her ritual, turning Tim to face the sink and roughly massaging his cock and balls. This time, Tim felt fully spent, and Zoe couldn't get even a twitch out his limp penis.

      "Oh not so excited now are we Tim?" she taunted. "If you don't get a move on and get hard I'm taking you back into the bedroom and back over my knee until you do. I'll count to three… one… two… three."

      Nothing. Tim stood forlornly, hands on head, as Zoe looked sternly on, her hands clamped over his penis and balls.

      "OK." She grabbed his ear, twisted, and guided him back to the bedroom, picking up her vibrator as she went. "I'm going to spank you until you're ready to give me one more orgasm like a big boy."

      Once in the bedroom she grabbed Tim's black belt from the closet. She knew he was less apt to behave when he had masturbated, and she didn't want him squirming too much. She put his hands together behind his back, and bound them tightly with the leather belt. She then plugged in the vibrator at the head of the bed, sat back against the wall, and manouvered Tim across her lap.

      Without hesitation, she picked up the bathbrush and landed it hard on Tim's still-sore bottom. He jerked and thrashed, but with his hands tied he was easy to control – she grabbed his bound hands with her left hand, hooked her leg over his legs, and went to town on his butt, making sure this was a spanking he would remember.

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    8. After what must have been thirty or forty swats, she felt a twitch on her thigh. "Ah ha," she said. "Let's see how we're doing down there?" She lifted her right leg off Tim's and said "legs apart young man." Keeping her right hand firmly gripped on Tim's tied hands, she swatted the inside of his thigh to make a point.

      Tim spread his legs wide, and Zoe reached through and grabbed his penis and balls, pulling them back and up so she could see them between his legs, smooshed against her thighs and the bed. She stroked and flicked, and abesnt-mindedly toyed with Tim's butt hole, before deciding that he was ready for another dry, painful orgasm. She grabbed the vibrator, and pushing it between Tim's legs she stroked it up and down the underside of his cock. Tim moaned and shuddered and finally came.

      Zoe turned off the vibrator, and gave Tim another 10 quick swats with the bathbrush, before untying him, lifting him off her lap, and putting him gently to bed.

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  28. I think she should leave him his "own personal" pair of panties to always have and to wear when she watches him so he never messes with hers ever again.
    On a separate note that may or may not fit this scenario I've always had was making a sub (or myself depending on watch tendencies) wear cum lip gloss. Wait till your glittery pink (or whatever shade you prefer) gets 3/4 or more empty, fill it up with a large load of spunk. Shake/mix well and enjoy as your sub must re apply glittery cum to his/her lips every 20 minutes or so.

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  29. Sounds like fun - we’ve done this stuff at home. Sometimes the babysitter punishes me because I’ve been rude to the neighborhood girls, and they’re invited to watch and then given “a turn”.

    You’d think the naughty boy would become immediately compliant, but you may notice him peeking up your skirt when you spank him. If so, he’s obviously not being spanked with sufficient intensity.

    Also, my “babysitter” has scolded me - calling me naughty, bratty, obstreperous, etc., so she made me write different sentences with 40 or so synonyms such as “I am obstreperous because I can’t stop trying to peek up my babysitter’s skirt”

    Have fun,

    Rosco

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    Replies
    1. Oh yes, neighbour girls should definitely drop by!

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  30. If incorporating diapers, perhaps the sitter could "find" his old bed wetter diapers in the closet or something. He would then have to admit that yes they were his but of course he doesn't need them anymore. As he is being put to bed early after his punishment, sitter thinks it's appropriate so he doesn't have to get out of bed to use the bathroom. As an experienced baby sitter (emphasis on baby), she would of course have no trouble getting him "pampered" up, all the while comparing him to her other young charges and commenting on how much his diapers look just like the one the two year old down the street wears. I'm blushing and dripping just thinking about how humiliating this would be!

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    1. Yes, and she knows exactly what she's doing, a nice little add on to his punishment. Let's add in baby wipes and a powdering!

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    2. Well, after that she could also accidentally find in the bottom of the kitchen cupboard (or cup place) his old baby bottle (that his mother ended up guarding as a remembrance of when he was a child) still in good condition, and deciding that it's time to reactivate it by a night...

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    3. A bottle feeding. Nice warm milk. In my arms. Nice!

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  31. A fun scenario and roleplay for sure with lots of great ideas from your readers.

    I would like to expand a little on KDPierre’s idea of it being the dad.

    I kind of see it going this way… The parents arrive home early from their trip having had to cut it short. They catch babysitter Julie near the end of her chastisement of their precious david. They are furious that she overstepped her bounds by physically punishing him. They are also angry at david for violating his sitter’s privacy. They decide that they need to spank both of you, him for his indiscretion, and Julie for violating their trust in caring for their little boy.

    It is decided that david will be spanked first and must go over Dad’s knee for a solid bare bottomed hand spanking. This would be followed by his being punished by Mom who decides to use her husband’s belt on him. After his parental punishment he is made to stand in the corner hands on head. His further told not to turn around or he will get more of the same.

    Next is babysitter Julie’s turn. She balks at the idea of david’s parents punishing her. She is then given a choice accept whatever punishment from them that they decide or they will have her charged with assaulting a minor. She hesitates only momentarily and then agrees to the punishment. The babysitter Julie is made to strip in front of both parents. She is further made to stand in front of them hands behind her head as she is admonished by the parents. David’s dad then stands up, takes a hold of the sitter’s wrist, pulls her over to the spanking chair and across his knee for the first of several spanking’s (and whatever else). Likewise for being spanked by david’s Mom (she of course preferring to use various kinds of implements). After all the spanking is done babysitter Julie she is made to stand in another corner hands behind her back. They admonish her further and remind her that she is there for the remainder of the weekend and can expect another spanking in the morning.

    David’s Mom questions again what started all this in the first place and after hearing the full story realizes that she too went through Julie things (making sure there were no drugs, etc.) while Julie was being shown the house alarm system by Dad. Mom confess’ to it and is then spanked by her husband and babysitter Julie for her breach of trust and indiscretion, she is also placed against the wall and reminded of another spanking in the morning. Dad then sits back and admires all three well spanked bottoms.

    The role of the parents could be filled out by John and Tracy.

    I know that there is less than a 0% chance of this scene ever happening, due to numerous reasons, and that it is also a fair bit removed from the strictly babysitter/ward scenario, but it would make for a great roleplay/ scene.

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    1. Don't think THIS babysitter is getting spanked!

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    2. Well of course THIS babysitter isn’t getting spanked!!

      That’s what “less than 0% percent chance of ever happening” means!!

      Perhaps THIS babysitter should have read all the way to the end of the comment! ;-)

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    3. Oh, I thought the less than 0 was because of involving a cast of thousands!

      I do know SOMEONE though, who is just begging for a good spanking...

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    4. I don’t know what kind of math they teach in Hogtown, but two extra people is hardly a cast of thousands!

      As for SOMEONE begging for a good spanking…THEY don’t have to BEG, all THEY need to do is ASK…I would be more than willing to give THEM the HELPING HAND THEY NEED and DESERVE!! ;-)

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    5. Does it means red rumps and thighs for Hogtown people ?

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    6. No, not a cast of thousands… just ONE!

      Oh, and Hogtown is one of many nicknames for Toronto,for those who don't know!

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    7. For spankings in the 6 see Mistress Violet Mays!

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  32. It made me think about a different senario, where the roles are reversed.
    You, Julie is the one who unfairly, as a young lady of maybe 18-20 (the age dosent matter, u get the jest) is forced by her parrents to have a babysitter.
    Of course this babysitter is David, and he is caught going through / trying on your panties.
    I think you see where this is going, a tiny bit of blackmail or plain naughty games and David will have a warm butt, imagine him have to submit to a younger girl, who might even threathen to call her girlfriend/girlfriends over to watch him in set panties.
    It is my understanding that David very much enjoy humiliation in your games, so this would be up there :)

    Best regards,
    Lasse

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    Replies
    1. I like it. David would be 18 and me the precocious 12-year-old domming him! (Fantasy age play folks - don't get excited! I WANT to be that 12-year-old!)

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    2. Just because a man gets distracted and peeks up a woman's skirt, or even reaches into her gym bag to sniff a pair of sweaty panties, does not mean he wants to wear a pair. How humiliating. Not fair, really. Why do women have such sexy underthings after all. It is only reasonable for a man to be a little obsessed.

      Also, younger women don't know how to wield their power responsibly, and are especially likely to get carried away when they are trying to impress their friends.

      This can be a volatile combination.

      -Rosco

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    3. A young woman getting carried away while inflicting embarrassing corporal punishment is somehow very sexy! Poor male...

      Delete
  33. Julie,
    Reading the comments and thinking about your original questions I like the realistic 50’s babysitter approach the most. It is a role you could pull off very effectively. Getting into character would be fun for both of you.

    She comes from a neighborhood home and has known david for many years.
    She has a couple younger brothers and thinks of david as one of them.
    Her mom is home with them all day and is the disciplinarian of the household.
    She has been spanked and seen her brothers spanked many times.
    When she punishes david she will be emulating her mother. Who she has heard,multiple times, say that boys need to be spanked longer and harder so they learn their lesson.
    Nothing sexual from her but she is totally shocked and offended that she catches david towards the end of his corner time trying to clean up his mess. After he has cum.
    Obviously his lesson has not been learned!
    Yet!
    Tom

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  34. As a baby sitter, you don't normally have spanking implements with you. So you need to use normal daily life items.
    The most handy is your own sneakers (I think you plan to wear one for this role play, so choose one with a hefty rubber sole).
    Next implement that was in most houses in a bread cutting board, if you don't have one use a wooden meat cutting board with handle, if you don't use a wooden spoon or a bath brush.
    For the strap, pretend that the boy's daddy forgot his trousers with a belt in the living room.

    Also, if you have a heavy soled home slipper / sandal, leave it beside the door at the entrance (just like they used to do that time, take off their shoes and change into home slippers once they arrive), send him to fetch mommy's slipper.
    Of course you can't make him enter his parents bedroom to fetch things as this in too uncommon for 1950s

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    1. I like that they keep the strap in the open in the basement. An invitation to use it!

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  35. If you look at the first picture, she seems to really want to make him cry. The last picture: she had fun and is satisfied with the result.

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    Replies
    1. Her face is angular. Her body is quite skinny and dry. Her blows must be nervous and hard. She must hurt a lot. Does she feel a sense of power to hurt a lot?
      She takes his pants off quickly, with lively and brisk gestures, an inward violence.

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    2. The first one is still a child, but the last one seems so sadistic that she could birch his teenage boy's belly, penis and testicles pulled back between his thighs, until he screams for mercy.

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    3. I identify more with "the child". Innocently brutal "for his own good".

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  36. ".. should I "encourage" him by giving him a little peakaboo at my tits?"

    Always a crowd-pleaser, and always works for me. And don't leave out your faithful readers who would enjoy a little peek, too!!!

    A,J.

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    Replies
    1. Sigh! Do you ALL need a spanking?!?

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    2. Ms Julie - isn't that the premise of your entire blog - that ALL men need to be regularly spanked hard, for both their own benefit and their significant other's amusement and enjoyment?

      -t.

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    3. "Sigh! Do you ALL need a spanking?!?"

      Does this mean we're gonna' get a peek...???

      A.J.

      Delete
  37. Dear Julie,
    I love the setup for this roleplay. I did something similar with my husband Barry over a year ago. Only our scenario involved me playing a young (age 23 or so) stepmother to his role of a young teenager. I discovered that he had been removing my dirty panties from the hamper and using them to masturbate. Of course, he didn’t want his father to find out, so he was firmly punished in a humiliating manner by me.

    I like your idea of being the prim and proper babysitter and him wearing the tighty-whitey underpants to begin with. With respect to some of your questions:
    • I would recommend that you require him to remove his shirt and trousers, but that you be the one who removes his underpants. Do it before the corner time so that he is completely nude for that part. And do it slowly to increase the humiliation. And be sure to tease him about his penis, especially if it is erect.
    • Definitely require a full half hour of corner time with his hands on his head. I would also recommend that you make him admit to having sniffed your dirty panties and using them to rub his penis. You could then make him hold a dirty pair of your panties against the wall with his nose (of course with the crotch area facing his nose) for the full half hour. If he is erect (which I’m sure he will be, you could hang another pair of your panties on his erectiion.
    • I liked one of your other viewer’s idea about using something other than a hairbrush for the warm-up, since the baby sitter might not have one with. However, instead of a sneaker, I would recommend an good stiff sandal. It will provide lots more sting.
    • As for the mouth soaping, I would recommend a combination lathering his mouth with a wash cloth and then making him hold the bar of soap in his mouth while being spanked.
    • With respect to the strapping, I doubt the babysitter would have a strap with her, but she could use David’s own belt!
    • I also recommend that you require him to masturbate with your panties prior to the strapping. He will remember the strapping much more that way.
    • If you are willing to set the roleplay in current times rather than the 50’s, I would recommend that you use your cell phone to take photos of him in the corner and while masturbating. You can let him know that if ever behaves in this way again, the photos will be sent to all of his friends.
    • Finally, a little peekaboo of your tits could increase his interest, as could some upskirt views of your panties. However, to stay in role, they should be discreet and appear to be accidental.

    I look forward to hearing what actually transpires. I may try a reprise of it with Barry. It should be fun.

    Susan

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    Replies
    1. Thank you! I will post after the roleplay so you all know my final choices!

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  38. Fig him with ginger root while spanking

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  39. Have you done the role play yet?

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  40. Dear Ms Julie,
    I would like to give you a couple of suggestion some are partialy mentioned by others. first of all apologies for my english but i0m from a mediterranean country.
    I suggest you to use the soap such as ivory soap but prepare the soap before by living it for 5/10 mins in warm water, mybe at your side or ready on the desk while spanking. If spanking occurs in the 50 the hairbrush would be more appropriete unless in your scenario you find a strap or a whip hanghing behind the kithchen door as it used to be. But if you are the one carring the instrument probably a brush is more approriate. Belt would also be used often at that time but more by males then females. Another Item very popular at the time was the vimini carpet beater but definately you would not carry it along as a baby sitter. Probably if you are requested in advance by some parents to educate their child your could carry a paddle or a cane which are effective also over a man panties. At the time for unruly children there was another non corporal punishment whish was a spoon o lever oil.....you can buy pills of it and make your husband chew them. Last but not leas disposable diapers are not appropriate. at the time only cloth diaper where available.....a nice folded tower will make your job.

    keep us posted.

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    Replies
    1. I think I will "find" the punishment strap hanging in the hall closet. Thinking I should have david mount it there for real and forever!

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    2. Ms Julie - if your hall closet also serves as a coat closet, perhaps having the strap hanging there would encourage david to be a better host, quickly taking/hanging and retrieving/returning your guests' coats, so as to avoid them doing it themselves and happening upon the punishment strap?

      -t.

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    3. Yes! And if not quick enough, I wonder if anybody would ask about it? "What's this?" I would probably pass it off as a "joke" - "oh, you know, need to keep hubby in line. Ha ha!"

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    4. Yes, making a joke of it would be good! Of course, some people might ask "Are you joking, or serious?" I could see men getting nervous (and maybe secretly aroused) about your answer, and women getting intrigued (and maybe excited, too) by what you say!

      I hope someone discovers it SOON, so you can write about their reaction to your "joke" ;-)

      -t.

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  41. Maybe make him wear t-shirt only with nothing else he has to hand wash your panties for you after giving him a good spanking?
    he will for sure have red sore butt you will inspect them if not done properly he get 50-100 with your thick belt or sneakers

    threat him with telling all of his friends or any of his female friends how he like to wear panties and be spanked wearing them. ask him if he know any female friend phone number threat you going invite them over to watch him get punishment when female friend come over yell door open come in first thing they see is him over your lap wearing panties you spanking him

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    Replies
    1. What a good imagination! Love these ideas.

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  42. Perhaps if you repeat this scenario by involving Sue as the boy's mom who thinks he didn't get enough punishment and spanks him again with the cane saved for big misdeeds.

    ReplyDelete
    Replies
    1. Not this time. I want it to be just the two of us. Let him know who owns that ass.

      Delete
  43. One of the key issues is a violation of the babysitter's privacy. Perhaps the babysitters couls go through David's personal items. Tit for tat seems fair.

    ReplyDelete
    Replies
    1. oooh! And what would he have? Perhaps a copy of Playboy magazine in those days?

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  44. "I give him a good hard slap across the face and tell him I know it was him and he should admit it. He again denies, but is starting to tear up. Another good hard slap across his face, and he breaks down crying, admits it, and apologizes."

    I LOVE the scene. C'mon Dave-boy, confess to my smart phone your dirty perv... Maybe I'll show it later to your momma! Don't look down! (SLAP!) Speak up!... Good boy. Baby sitting it's a hard work but a little blackmail can be a discrete helping hand...

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    Replies
    1. No blackmail like that. I like that as the babysitter I have sufficient "personal authority" to see it through without calling on parents!

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  45. Julie,
    Reading and rereading your role play plans and the suggestions was amazing but sheer torture for me. I reallly begged my wife to give me a break and unlock me earlier than planned from the Birdcage chastity device I wear. Of course my device will stay on until February ;-) But I warned my wife that she better watch out because I’m turned on and frustrated enough to do some serious role playing with her as soon as the frees my manhood. I think she’s looking forward to it.

    ReplyDelete
    Replies
    1. Perhaps she should do this roleplay before the cage comes off (well, MOST of it - right until the very end that is)

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    2. Julie,
      Sounds like it might be fun. Perhaps the role play would be her giving me reasons why my cage shouldn’t be coming off anymore for orgasms, and me begging and pleading to the contrary. I’d suggest that but I don’t want to give my wife any ideas. Besides, she teases about that occasionally.

      Delete
  46. When will you do this role play Julie?

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    Replies
    1. david's been away traveling on business (hope he has not been naughty while away). When he gets back!

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    2. How does he keep his bottom warm and red while he is away? Self-spanking? Seeking professional help?

      Delete
  47. I've found that being forced to kneel on dried beans to be highly effective (an old school method practiced by rigorous monks / nuns).

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    Replies
    1. Mistress Violet!!!!! Very excited to have you comment! What brings you by?

      I shall have to lay in a supply for my bad boy to kneel upon when he's been naughty!

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    2. and then that would be his dinner from the doggy dish too ;-)

      April

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  48. If you really want to live out the FULL Babysitter fantasy and make him like a true little boy, tell him about your "college boyfriend" who's older, stronger, has a much bigger cock than little David there (obviously).

    While David's fully naked and turned on with his freshly spanked bum, maybe treat him like a little boy (using younger language, maybe lying across your lap for some cooling lotion on his rear?) and tell him about ALL the things your college boyfriend does to you that little boys just "can't".

    As your fingers slip into his rear while you're applying the lotion, make sure you emphasize that you DON'T see him as a sexual being, that's left to the REAL men with real cocks.

    And if little David has a humiliating squirt all over your legs while you describe your nights with your boyfriend's bigger, better cock, maybe you've just found a NEW fetish to exploit?

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    Replies
    1. That is... gulp... very exciting...

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  49. I'm again looking at the first photo in your post of the girl (she certainly looks more a girl vs. an adult woman). The more I looked the more I thought - "Damn. That girl could really do it" - use that hairbrush on a bare bottom!!!! And she'd make it real.

    Was there a story behind the photo? Seeing the pic of a sailor on her table, could she just be a very young-looking married woman vs. a teen?

    A.J. (Yes; it's a slow day.)

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    1. Something about her I really like!

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    2. Yeah! I know what you mean. I just like her. Go figure.

      I also note she is holding a mirror vs. the hairbrush that is on her side table. So what do you suppose is on her mind...?

      A.J.

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    3. To reactivate the threat for david of this humiliating punishment among all (and the least desired by him), maybe it would be appropriate that Juliesitter reminds him that a magisterial spanking administered with bare hands by his boyfriend (or sailor-husband ) could be in store.

      (Without speaking about an other one kind of intrusion that could make him think twice before violating a young girl's intimacy again.)

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    4. That would indeed teach him a lesson he would not soon forget!

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  50. Hi Julie,

    As you know I swing by your blog from time to time, but this time I had a client request a session based on this very same role play scene. Living in a FLR is the dream, but hiring a Pro might be second best ;)

    Anyway, we pretty much played out this exact scenario, steering clear of diaper play and bi-scenes. I love the Mad Men-esque vibe, and as I got to play babysitter, I went with a light pink dress & chocolate brown cardigan with puffy shoulders. Soft pink heels and pink stockings. Very innocent but put together in a strict way.

    We had a timeout in the corner, hairbrush spanking on the bottom, and then yes we did the soap in the mouth! I picked out a cucumber soap from a health food store as I just had a feeling that would be the safest, and I also soaked the bar in warm water for 15 minutes before - thanks to a comment from one of your readers - which helped with the suds. I also made sure to put the cream in the fridge - very fun when applied to a sore and rosy bottom!

    Let me know when you've done the scene with your boy and we can compare notes.

    Violet Mays




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    1. Oh my gosh!!! That's amazing! I love that your client was inspired to do that! I will email. This is so exciting!!!

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  51. Client you say ? You sure you know where David is exactly ? "On business"?

    Sounds like he could have made a pit stop appointment with Miss Violet ;)

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    Replies
    1. I know EXACTLY where that boy is at all times. No "pitstops" for him!

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  52. Butt plug with GPS tracker Miss ? That you can access from your phone? ;)

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