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!

Husband gets sexy handjob across Wife's Knee

david's been a doll lately. He's always thinking about me in the sack. At bedtime, when I nuzzle my bare backside up against him he immediately starts fondling and kissing me, quickly progressing to going down on me and giving me one or a few really lovely orgasms. Of course, afterwards all I want to do is roll over and go to sleep, so poor hubby is left with a massive hard on. He's not allowed to jerk off in bed when I'm trying to sleep (for obvious reasons), and he's not allowed up and out of bed (as he starts his day very early and needs his rest), and he also mustn't wiggle or squirm (so annoying!). As a result, every now and then I get quite guilty over not reciprocating, so yesterday I decided I would give him a treat.

I collected him early for bedtime. I had him strip down to his undies and lie across my lap. I was seated on the side of our bed. I started in by giving him a light hand spanking and hand groping as I teased him by moving his underwear in and out and around. I then pulled his underpants down his legs and off his feet and continued with my light spanking and fondling. I reached between his legs and pulled his cock and balls out, making him close his legs to trap them where I could see them and touch them.

I continued his spanking and also started fondling his penis and testicles with my small, soft, cool hand. david is very verbal-sexual so I like to spin a few fantasies for him as I do this. Here are some of the sorts of things I said.

"So aren't you ashamed? Across your wife's knee getting spanked like this. What would the ladies at the office think if they knew this is how you like to get off? Like a naughty little boy across his Mama's knee?"

I can gauge the effectiveness of my little stories by his squirming and moaning, the colour of his cocktip, and the strength and "twitchyness" of his erection.

I reached over to the bedside drawer and pulled out the baby oil. Though his head was down and away, he could tell from my motions and the sounds what was coming, and he squirmed deliciously across my knee. I opened the bottle and poured some baby oil on his cock and balls, and into his ass crack, and started massaging it in. I also kept up with alternating to his light hand spanking as well, now with an oily hand. His breathing got faster.

"Remember how you used to go to massage parlours behind my back? Is this what those girls did to you? Did they rub your cock like this? I imagine they didn't have you across their knees though! What would they have thought had you asked them for what you really wanted? To be across their knees like this, getting a spanking. Would they have laughed at you? Called you a sissy boy? Or at least thought it? What if one of them had taken one look at you, sized you up, and put you across her knee? You would have liked that, wouldn't you have? Maybe I'll take you back there, and pre-arrange for a girl to do that while I watch. Would you enjoy that? Maybe pay for two or three to come in and watch as well. Sissy husband getting a sissy handjob across a young lady's knee, your panties pulled right down. Getting spanked like this while you get rubbed? Swallowing afterwards. I think they'd enjoy seeing that."

Then I started playing with his bottom hole with my other hand. I teased him by touching gently and slowly pulling away. His ass followed. I held my finger touching but just out of reach so that the only way he could get penetrated was by pushing his ass aggressively into the air, impaling himself that way, which I allowed.

I changed the scene again.

"You like that, do you? You like me touching your bumhole? You're behaving like such a little slut, begging for my finger up in there. Is this what your Doctor does to you? Puts her finger up in here and feels around? Do you embarrass yourself like you're doing now when she does it? I bet you do and don't even know it. I was in to visit her the other day, did you know? She has a very young and attractive nurse who just started. I gave her my permission to conduct your next digital exam, while the Doctor watches and double checks of course. I hope you don't mind? I also requested she check the volume of your ejaculations. I think it's headed down a bit, although you might prove me wrong today. I want a nice big healthy load so there's more for you to have to swallow afterwards. Ha ha! You know I even told the Doctor and nurse that, and do you know, they laughed aloud? I suggested they kill two birds with one stone and put you across the young nurse's knee just like you are now for both the prostate exam and your ejaculation test. Can you imagine that?

You across the pretty young nurse's knee, her doing to you what I'm doing now, while the Doctor watches and shakes her head at my pussy whipped husband? I said to speed it along that they should slap your ass like a little whore. That you get 'turned on' by being spanked by a woman. They had a huge laugh over that one!"

He bucked and squirmed with those thoughts in his mind as he jetted a huge ejaculation into my hand and onto the backs of his legs. I scooped up as much as I could into the palm of my left hand. I outstretched it in front of his face as he remained across my knee, and made him lap it all up as I continued spanking him, and then swallow it all down as I watched, every last drop (Julie's rule!).

Christmas Tradition with Sister Sue

Well, Christmas and now New Years have come and gone. We have had a bit of an on again and off again tradition regarding Sue's gift to david, but she has carried on the tradition this year: The Christmas Spank and Wank!

2016: Husband Given Hand Job by Sister

2012: Sister Milks Husband

This time there was no formal exchange of gifts or cards within the family except for the kids (we decided it's getting to be too much). david did give Sue a gift from us - one nice and one very nice bottle of wine when the family was over at her place, disguised as a hostess gift - Sue knew to serve the nice one, and stash the very nice one for a special occasion.

But david had the temerity to go up to Sue and say, with a big puppy dog face, "I know you already gave Julie her present, but nothing for me this year?" I was standing right there and might have blushed a bit. Sue patted david's cheek and said "of course there's a gift for you, just like Julie's". Oh oh for him! Sue was over the other day, during the holidays, to deliver it, and boy did she ever!


By the way, I guess I should say that subsequent to my strict but sexy bare breasted disciplining from Sue (see Spanked by my Sister), that she and I did have a chance to chat in person. I had her alone and coquettishly thanked her once again for my spanking. I was trying to figure out if she was ok with things, if it might happen again, if she wanted one, or what.

She said that she thought I didn't want to talk about it at all. True. I got up the courage, though, to tell her that I couldn't help thinking about it... (so bad!). She got a smile on her face and asked what part of it I thought about. Ok, now we're flirting! (and with my sister! Yuck!) I felt this question was an oblique reference to my having had an orgasm or three during my spanking (!).

I dodged having to admit to my orgasm by answering instead, "I thought most about how much it hurt!", which I said with what I hoped was a cute pout.

"Oh, is that it?" she said, laughing at me, "well you just let me know when you want another," she said with a big grin.

Oh good. I was glad she did not regret it at all. Knowing how she reacted last time to my asking for it to be not so hard, I thought I would play that game again: "ok, but not so hard next time?"

"Harder," she said, "and longer - careful what you ask for." Ohhhh! If I ever get up the nerve to ask again, my bum is going to be soooo sore and red! I am such a fucking switch and she knows it. I knew because of this answer that it would be impossible to get it out of my mind now!

But I wasn't done playing yet. Wondered what she would make of my next demand: "But not my breasts next time, ok? That really hurt." I said it with a concerned look in my eyes. Guess how she answered? Yup!

"Especially your breasts next time," she said. "I'll whip them rosy red." Relentless!

"They're delicate," I said, cupping them gently.

"Yes they are," she said.

"Well I might not ask, in that case!" I said with another pout.

"Your choice," she said. Checkmate!

"Oh fine. But will I ever get to return the favour at all? Give you a nice little spanking?" I asked.

She looked at me as if she was scandalized: "No!" she said. "What do you take me for? A submissive?" She said this with a sneer in her voice as she said the word "submissive".

Oh great. She thinks less of me for having submissive tendencies. I felt that sort of pierce me. I used to identify as a pure top myself. There is nothing in the least embarrassing about that. But identifying as a submissive, no other way to cut it, is humiliating. You crave your kicks by submitting yourself to another, undergoing whatever humiliations she dreams up, taking whatever pain she gives out, just for that feeling. It's tummy churning in its embarrassment. But that tummy churning embarrassment is exactly part of the feeling you are after!

So that was that. I now know a repeat performance is on offer, and pretty much know what I would get if I were to ask her again: an epic ass beating plus a breast whipping! I'm sure she would not spare me the embarrassment of another orgasm across her knee either. And it's not so much of a stretch her ordering my husband, under her direction and supervision, to sexually abuse me as well. She used to have Barbie and Ken dolls. Now she has the two of us. It would be so bad. Now, if only I can stop thinking about it!

Anyways, this post is not about me, but rather about david's Holiday gift from Sue: his spank and wank, so let's get back to that!


When Sue came over david was very excited. He so likes his sister-in-law and is so excited to see her. I made him strip bare and show us exactly how excited he was to see her!

"Wank first or spank first?" asked Sue. We have a friend from the UK who refers to male masturbation as "wanking". Sue has taken to use it to mean giving him a handjob as well (perhaps incorrectly? Help me out you Brits out there!).

"Ummm... spank first?" asked david, hopefully.

"No," said Sue. "Given you so impertinently asked me for your gift this year, I think we'll do it the other way around. And this year your wife will give you your wanking, and then I'll give you your spanking."

"What fun!" I said, clapping my hands in glee. I hoped david wasn't too terribly disappointed by this turn of events. I guess I wasn't sorry that Sue was insisting I do the honours. While intellectually I enjoy allowing Sue to give david a handjob from time to time, there might be a touch of stupid jealousy in there. I was secretly glad she was asserting who was the wife in this relationship, but would never admit that!

"Should we make him hold his splooge in his mouth while you spank him?" I asked, in what I thought was a very nonchalant manner. It's a favourite trick of mine, especially when I know the spanking will be hard. A very effective way of gagging him. I am such a sadist. I love hearing those clothed-mouthed screams of pain from my man knowing he's holding in a big mouthful of his own ejaculate. Somehow fitting for males, given the amount of hornyness they generally get up to (although I'm one to talk!)

"I don't see why not. Let's," answered Sue.

"Where should I do it," I asked, "up in the bedroom alone with him, or down here with you?" I wasn't 100% sure what she wanted, given she had requested I do the more sexually oriented honours.

"Oh right here is fine. I want to see." Sue enjoys seeing a male made to spurt, especially my husband.

"Stay there," I told david, "I'll get the oil." I left david standing in his altogether in front of my sister, excitement on full display, while I went to fetch the baby oil and a towel. I wonder what they talked about while I was gone?

david receives his handjobs with the baby oil

I spread the white towel out on the seat of the couch and had david come over and lie face up. He remained very excited as he lay down.

Isn't that a pretty sight?
Eager and ready. So naively waiting there.
Willing to put up with any amount of
teasing and abuse, just for a nice cum.

I also brought down with me the dreaded wooden spanking spoon we keep in the bedroom (I now know it very well - very intimately acquainted, she and I).

I asked Sue if this was what she wanted, and she told me that I had read her mind. She had a little grin on her face, which I interpreted as being a reference to my wooden spoon spanking at her hands, when I came while across her lap (Blush Blush Blush!)

I sat next to him on the couch and began dripping baby oil onto his cock and balls and then started rubbing him.

"Hope you enjoy this," said Sue. "You know what's coming next," she added as she smacked the wooden spoon into her palm.

Audrey Knight

I rubbed him until he had gotten very excited indeed and then I started teasing him, much to Sue's delight. I squeezed the bottom of his shaft and made his head stand out bright red. Like this.

Then I gave his cocktip a good hard smack. Then pushed it down onto his tummy and spanked the underside of the shaft and head up and down until he howled. Amazing how fast he limpens! Then I started in rubbing him again, quickly getting him back to full hard-on. As he was getting close, and I was feeling some pre-cum I lightened my grip and just gently circled my fingertips around his head.

"How am I doing?" I asked Sue.

"9.5," she answered, playing the Russian judge at the Olympics.

"I think he's ready to spurt," I told my sister.

"Awwww. Are you ready to spurt david? asked Sue. "As soon as you do, it's right across my lap for your spanking."

"And the more you cum," I added, "the more you'll have to hold in your mouth during your spanking. You'll get to swallow it all afterwards. But you better open wide and show me a good mouthful of cum after Sue is done with you, or else I'll take the skin off your bum with my strap."

As we spoke like this he got even more excited. And I let his cock dangle in the air completely, just giving him the slightest little rubbing on his urethra.

"Please...!" he begged me as he made a shameful display of humping his hips up and down trying to get me to touch him harder.

"I'll need Sue's permission, but maybe we should start your spanking now," I suggested, "with you in this state. Let you hump Sue's knee while she spanks you and cum all over her lap." I winked at Sue as I said this. It was self-referential, as I had done exactly that across her knee but we had never discussed it. The wink was also so she would know I was not serious about it. "She'd have to hike her dress right up so you don't mess it, and take her pantyhose off so you can rub her bare skin."

"Yes! Please Yes!" begged david, thinking that I was actually serious and this was something I had arranged with Sue. Poor deluded boy.

"I'll make a deal with you," I told him, if you can hold off for... let's see now... another whole minute, then we'll ask Sue if she would do that for you. Ok?"

"No! Please!!!" said david, knowing he could not last 10 seconds if I started rubbing him in earnest again.

"Well, let's see you try anyways," I said in a cheery voice as I re-engaged with his cock and started giving him full hard slow shaft to tip strokes with my tight little slippery closed fist.

"No!" he begged as he squirmed under me, "I can't!" he begged.

"Do you like it tight like this?" I asked him. "Is it like fucking my bottom hole, david? Like what Sue made you do to me after my spanking? Is that what my hand feels like, david? I hope you don't cum early this time, like you did when your cock was buried up my butt." I had the dual purpose of making david cum, but also just couldn't stop thinking about my spanking from Sue!!!

"Oh no!" he said as he ejaculated all over and onto the back of my hand.

"Oh! You bad boy!" I told him. "Just can't hold it, can you? And just look at the huge mess you've made! That's all going in your mouth now, young man, and you can just hold it there while Sue gives you the spanking you deserve."

I told him to "open" and "don't swallow" as I transferred as much of his ejaculate as I could from my hands; and his cock, tummy, and balls; to his mouth. In the process I assaulted his penis by squeezing out every last drop and roughly rubbing his now super-sensitive tip, a trick I had learned not so long ago: post-orgasm punishment! He wiggled and flopped, amusing both me and his sister-in-law as I concentrated on his poor abused cocktip. david was unable to say anything or even beg, given the mouthful I had made him hold.

I then got a cloth from the kitchen and cleaned his midsection up a bit.

"Poor boy," I said, fondling his balls. "Now you have to get your spanking after you've cum. It's going to hurt a lot more like that, won't it?" I asked him.

"Mmmm mmmm" he said nodding his head up and down, keeping his mouth tightly closed.

"You won't swallow now, will you?"

"Nnnn nnnn" he said, shaking his head no.

"Good, because I don't want to have to strap the skin off your backside after Sue's already spanked you. But you know I will, don't you?"

"Mmmm mmmm" he nodded his head up and down, confirming that he did know that. Well, not literally taking the skin off. More figuratively speaking.

"Will you go over you sister-in-law's knee like a good little boy, and take every last stroke?"

"Mmmm mmmm" he nodded affirmatively.

"Just look at him, Sue," I said to her, "his cheeks like a little chipmunk's."

"You keep that all in your mouth," echoed Sue, "and don't swallow any. There'll be inspection after, and I'm sure you won't be wanting your wife's strap after I'm done with you," stated Sue. david nodded affirmatively at this. Then turning to me, Sue said, "give me the towel for my lap, he may be still a bit wet and goopy."

I took the towel and draped it across Sue's lap which she re-positioned to over her left knee only. Ominously she then took him right over her left knee and placed her right leg across the backs of both of his, clamping him down with his bum high. Not promising for him regarding leniency!

Love this image!
Could be Sue, david and I.
Just colour me blonde and substitute the wooden spoon for the hairbrush!

Sue deployed spoon to bum. She started a bit lightly, but fairly rapidly ramped it up to a level that had david wiggling his ass and "mmmm"ing. The way she had him bent over (similar to the drawing above) gave her easy access to his lower cheeks, thighs, and inner cleft. As she spanked, his little brown bumhole winked at us saucily! She was as determined with david as she had been with me to well-punish those naughty bare ass cheeks.

She must have stuck with it for at minimum a good hearty five minutes or so, at a rate I would guess to be about once a second. But I wasn't timing or anything. It did feel long, though! So well over a couple of hundred good hard ones that left his backside deep red with spoon-shaped bruises white in the middle. He did look like he was suffering, especially as he had to keep his mouth closed throughout and breath entirely through an increasingly snotty nose. The entire time he was kept jacknifed and clamped over Sue's left knee, ass high. Despite the length and the severity, I did feel that she had nonetheless gone harder on me!

When she decided he was done, she released him and he sank down onto his knees, clutching at his cheeks. His eyes were wet and his nose was running, but no big tears like for me. We had him there kneeling, positioned in front of Sue and I. I made him look up at us and show us. He opened his mouth like a little bird, and it was clear that there was still a good deal of ejaculate in there, at least to the extent that Sue and I were both satisfied with his efforts. I grabbed him gently around his throat with my one hand, tilted his head back and clamped his nose with my other, and ordered him to swallow. I could feel his throat convulse as he swallowed down his own load. Love that!

"Good girl!" said Sue as he took his ejaculate down his throat.

"A little corner time now," I told him.

"Here, stick this up his bum," suggested Sue, handing me the wooden spoon!

"No! We may want to use that again." (was I speaking about myself?). "And besides, I don't want to get splinters up his ass. Here, I have an idea," I said, and went to the kitchen and pulled out a red plastic spoon. More washable and less splintery!

I had david bend over and put his arms down on the couch. Then I used the baby oil to lubricate the handle of the spoon, and inserted it up into his rectum, far enough that it would stay there. I touched up his backside a bit more with Sue's wooden spoon. We both laughed as his red plastic spoon jiggled around in the air, amplifying his butt's movements. Sue came over and jiggled his little tail for him.

I then sent him to stand in the corner showing off his red bum with that ridiculous red spoon sticking out his anus. Sue suggested we make him carry an egg around in the bowl of the spoon, and whip him if it drops, but she wasn't serious.

how humbling... Evil sisters... what mischief!

I didn't take any pics of david like that, so I thought I would find some reasonably close images on the web and insert a red spoon myself into his ass using Photoshop. Not such a great result, but gives you the general idea! Humbling to have to stand there in front of his wife and sister-in-law after,

1. a forced handjob from his wife, making a spectacle of himself in front of his sister-in-law;
2. a good hard wooden spoon spanking across his sister-in-law's knee in front of his wife;
3. having to hold his own cum in his mouth during that entire ordeal, under threat of a severe strapping from Mommy if he didn't;
4. a forced slutty swallow afterwards (every last drop!), minutely witnessed by us mischievous sisters;
5. and then having to endure us laughing at a kitchen spoon inserted deep into his rectum for corner time!

Priceless.

We left david there while Sue packed up and left, bright red ass cheeks on show, the kitchen spoon obscenely protruding out his rectum. Afterwards I came up to him, grabbed him by the ear and dragged him up to our bedroom. I told him the spoon stays in until he's gotten me off at least three times with his tongue (three is my magic number. I was horny watching him get his bum beat so it was not much of a challenge).

A nice gift from Sue on top of my earlier one to him. What a sexy holiday season for him!