Sandy's Story - First Assignment

I've been helping this delightful couple, vanilla Tom and spanko Sandy, to get Sandy the spanking she needs from Tom.

Where we left off in Sandy's Story - Tom's Response, Tom was willing to give it a go and so we did a preliminary exercise where they read through some material regarding the spanking fetish and discussed it.

Before progressing to any "hands-on" exercises, I sent Sandy and Tom a confirmatory email concerning safewords.

Hey guys,

Before I get you at all hands-on with one another, I want you both to acknowledge for me that you will use "safewords". You read about them in the blog article, but wanted to confirm explicitly.

For the full stop safeword, many use "red". You guys can choose your own if you like.

Because part of this kink is for the bottom to want to feel the emotions of resisting a bit, and maybe say things like "no, please, not that!" or whatever, we need a separate word, otherwise unlikely to come up, that means a full stop to activities and a snap right back into reality and a careful and loving check-in, no matter what, and with zero exceptions.

If either of you are getting uncomfortable, physically or emotionally, with where a scene or activity is going, you use the safeword. Tom, that applies to you also. If you are getting uncomfortable in the midst of doing what you've agreed to do in advance, you can safeword out as well and check-in.

If you do safeword out, the rule is that the session is done. You'll need space to digest and discuss and understand what each of you are feeling before you try again.

And no recriminations if a safeword is used. You're learning each others' boundaries, and it's part and parcel.

Is that ok? Do I have your words on that?

They both responded back with a nice quick "yes Ma'am" on that one, so I felt that aspect of due diligence was done.

Sandy had done some scans for me of her formative childhood spanking materials. I blogged about the first one in Sandy's Story - Barbarella.

First spanking image Sandy masturbated to at 13 years old

There is an erotic book she purchased subsequently called "Ellen's Story" that I will also post soonest.

Sandy mentioned that Tom spotted her scanning these things in

P.s. Tom saw what I was doing as I was scanning and asked me about it. I told him everything above. He declared me a "precocious" child, but admitted to jerking off to naked girls at that age himself. Double standard or what?

P.p.s. I got a little worked up doing all that scanning and stuff, and we had great sex that night. I came being fucked doggy style and fingering myself, and then he nutted a moment later into me. Because it was top of mind, I imagined he was Roderick from Ellen's Story and I was Ellen. But per your instructions, Tom was banned from spanking me. I think he may have wanted to, though.

I was inspired by that to dream-up my first hands-on exercise and wanted to run it past Sandy to see if she was ok with it.

Sandy,

Glad the sex was good, and yes, no spanking until I say so! Thank you for filling in more of your origin story. And I LOVE Ellen's Story!!!!

I had an idea reading your account of your childhoodd masturbation and was wondering if you are good with it. I was thinking of making Tom "order you" to masturbate like you did when you were a kid as he watches. Maybe read aloud to him your favourite part of Ellen's Story, and then, when you are ready, turn over with that pillow between your legs and masturbate while he watches. I'll tell him to lightly pat your bum as you're doing it, so you get a hint of a spanking sensation. I would ask you to vocalize your thoughts around Ellen's Story as you get yourself off. Is that something you think you'd be ok with doing?

Also, in contemplating what to tell Tom, I've not really dug into what you want, spanking wise. You said "anything you like, I like", but I want to dig into that more. So here are some more questions for you:

[... Sandy reproduces my questions in her response...]

That's all I can think of for now! Quick answers are fine.

Julie

Sandy very quickly wrote back to me.

Hi Julie,

Masturbating like that in front of Tom would be highly embarrassing. Triggers my "being discovered" fears. But I could bring myself to do it if Tom asks me to.

Answers to your other questions:

1. Is it your goal to get to a "taken-in-hand" sort of "spanked girlfriend" relationship like mine. i.e., really spanked for when you do something wrong? 

That's what I fantasize about, but I'm worried what the reality of it would be like for our relationship. It doesn't need to be for real, like you, but if after he spanks me for a while and we drift into it a bit naturally, like you did, then I would like that, I think. But I'm not 100% sure.

2. Are you excited at all and do you want more S&M and master/slave sort of play, or is it pure DD? 

I'm pretty much 100% domestic. I see some of the whips and chains videos and I turn into a total vanilla myself and think they need their heads examined. Am deeply conscious of the irony of what I just wrote.

3. Are you into girls at all?

No, not really. Lesbian scenes don't do anything for me. The thought of being spanked by an older woman in a domestic type situation does turn me on, though (Julie...).

4. Do you wish to do fantasy roleplays, and if so, what sort of roles (principal/student, cop/civilian, judge/accused, doctor/patient, boss/secretary, ...)

Yes, all of those things sound like fun. You left off "Strict husband / Naughty Wife" roleplay, but that would be my go to.

5. Do you have a strong Daddy/daughter sort of fetish? Do you want to be his little? Is diapering a thing for you?

No, not as strongly as you. The thought of my actual Dad spanking me is a total turn-off. I guess we're not 100% the same. Good thing you're asking. But my "strict husband" fantasy sort of merges into an "abstract daddy" sort of thing, if you know what I mean? So my fantasy husband treating me as if I was his daughter is a bit of a turn-on. I don't get turned on by being a little or being diapered, but if I'm "forced" into those things, as punishment for being immature maybe, then it becomes a turn-on. For example, I liked it in your book where as punishment for your pride you were required to go to Sunday School and be treated like the little kids, diapers and potty and everything.

6. Is spanking the only punishment you crave or are there other things, such as corner time, line writing, mouth soaping, enemas, plugs, ginger roots, icy hot, pussy punishment, breast punishment, ...

Any and all of those things I'd be willing to try at least once. As long as it was in a domestic context.

7. Would you enjoy any sort of mild public play, like being told by Tom in front of another man that you're being naughty and you're going to get a spanking when he gets you home?

Yes! Subject to not upsetting people or getting Tom arrested for wife beating. Would also be turned on even if Tom just threatened to make my spankings public while he was spanking me.

8. You mentioned before you consider yourself anal erotic. Would you like to be fingered or fucked by Tom in the ass?

Fingers for sure. Not sure what an ass fucking would feel like. If it would be too painful then no. But the idea of it as "punishment" is sexy.

9. Do you want to be "punished" by Tom using vibrators on you and in you, getting you closer and closer to orgasm?

Sure!

10. What are the spanking positions you most dream about? 

- Big number one is OTK.
- You've described the pussy straddle variation, which I dream about.
- Being bent way over something
- Diaper position

11. What are the sorts of implements, if any, you would want Tom to use the most? (belt, hairbrush, paddle, cane, switch, flogger, ...)

I don't know if we'll ever get him past the hand, and that would be good enough (and the one I want most).

But, belt, hairbrush, strap, paddle, those sorts of things would be good. Not sure about canes or switches. Floggers don't feel domestic enough (but I do fantasize about a French martinet to the fronts of my bared thighs).

And you didn't ask, but spanks to the thighs (front and back), inner thighs, inner bum crack, even tits and pussy, are all a yes in a domestic type scene.

Now you've gone and gotten me very worked up.

Sandy

Aren't those all lovely answers! Tom - take careful note. We're writing a "manual" here for your girlfriend. It was pretty much all as I thought, but a little different around the edges, so I was glad I cleared it all up.

I decided to go ahead with my exercise. I sent Tom an email.

Hi Tom,

I wanted to clear up the safeword thing before I gave you a bit of a hands-on exercise.

I have a kinky and educational thing I'd like you to ask of Sandy. I've already cleared this with her and she's game.

Like all spanko bottoms, she likes to be told what to do by her "top" (that's you), so don't ask her if she wants to do this, tell her she's going to do it. Even if (especially if) she says no, you should insist. She'll eventually do as she's told if you're firm with her.

As you're just getting used to this, Tom, if you are starting to feel like her "no" really does mean "no", then check-in with "I hear you saying no, but I'm not hearing our safeword..."

Ok, this is what I want.

She's probably shared with you that she has this favourite spanking novel she had from the time she was a kid called "Ellen's Story". She used to use a flashlight in her room at bedtime, re-read her favourite bits, and then put down the book, turn over on her tummy, hike up her nightgown, squeeze a pillow between her legs, and finger herself until she orgasmed thinking about the scene she just read. She was always nervous, and a bit turned on, that she would be discovered doing this. This was when she was 13-14, and it was very formative to her fetishistic sexuality.

I want you to insist she does this with you watching. First have her in bed in her nightgown, no panties, or nude is ok also. Ask her to choose a favourite part and have her read it out loud to herself, with you in the bed beside her (fully clothed) listening. She's not to read it to you. She's to read it to herself, but out loud.

Then tell her to show you how she masturbated as a kid. You might have to insist against some embarrassed resistance here. Being embarrassed like this is part of her fetish.

As she starts doing it, pat her gently on her bare bum. Not caresses, just super light taps with your open palm. It's not a spanking, it's just the hint of a spanking. Move all around her bum, and even a little into her bottom cleft and her inner thighs. Ask her to tell you who she is imaging she is, and what she is imagining is happening to her.

Tell her she is a naughty girl, and she deserves a spanking. Have her acknowledge out loud that she is a naughty girl. Then ask her how naughty girls are punished. You're not going to spank her, it's just a tease. And don't be tempted to swat her ass, only very light spanks. Goal is to drive her crazy with anticipation for a real spanking from you somewhere down the line.

In the immediate aftermath of her orgasm, pet her and hug her close and praise her for being such a good girl and for being so obedient with you.

I think observing her in her "native element" like this will actually be very instructional for you.

If you get horny from all of this, feel free to have sex with her as usual afterwards.

Julie

Tom wrote back,

That actually sounds fun. Will do.

That's nice. He seems to be getting into it. I immediately wrote back to Sandy to confirm.

Sandy,

FYI, I've asked Tom to "make you" do that masturbation exercise I wrote to you about. He knows I've cleared it with you so no backing out now. I think a little bit of resistance would be appropriate from you. Beg him not to. Tell him how embarrassed you would be. Not too much, but a bit to get him used to being firm with you.

If it's not happening for you, fake an orgasm. I need this to be an absolute success for Tom. Praise him afterwards on how masterful he was (lie if you have to!). Thank him for doing this for you. Reward him with great sex, and do something unexpected for him later, like cook a great meal as a big thank you. I won't publish this email, so if you do fake it, your secret will be safe!

Julie

Sandy immediately wrote back and said,

You're enjoying this, aren't you? 😉

I gave a one word "Yes!" response. Ha ha!

So, I did publish the above email, because as you shall read below, no faking was required, just the opposite in fact - the little minx was on a hair trigger, and mostly because Tom did such an amazing job!

It was a couple of days until it happened, and then I received an email from Sandy with a her recount of the exercise.

Hi Julie,

Tom and I completed our masturbation assignment. It was really good. We've decided to each write you our takes, cc'ing one another if that's ok. Here's mine. Tom proofread and helped me get a few of the facts straight. Not sure if the talking we reproduces is 100% dead on but it was more or less like that Tom and I both agree.

It was yesterday evening, around 9pm. Tom came to me and says we have some homework assigned by you to take care of. I knew what was coming. Thank you for the heads up.

He told me to put on something like the nightgown I wore when I was 13, go get "Ellen's Story", and meet him in the bed.

I went to the bedroom and Tom had lit two candles (! awwww !), had the lights dim, and had run the space heater with the door closed so that it was toasty in there (I always like it warmer in the house than he, so it was a real treat and a sacrifice).

I don't have a nightgown anymore, but I do have a longish night shirt, so I put that on. I got the book and then I joined him in bed. We were both on top of the covers. He had all his clothes still on. I normally sleep naked, so going to bed like this actually made me feel little again, given the context.

He told me to pick my favourite passage from the book and to read it to myself, but out loud so he could hear. I teased him that it wasn't reading to myself if he could hear it.

"Do as you're told," he told me but with a smile.

Oh, my heart skipped a beat at that. THIS is what I want.

"Ok," I said.

I picked my very favourite part. It was pretty long, practically a whole chapter, but it was a dear old friend and I needed her there with me that night.

It's the passage I sent you already, in Chapter 3, A Plot of Civil Disobedience. Two 18-year-old girls get bare bottom spankings from three rough workers because the girls were misbehaving. Maybe you could post those pages if you publish this?

I read all 15 pages aloud with Tom beside me listening. My voice caught at the best parts, and I squirmed on the bed. At a certain point I put my hand down, lifted my nighty, and rubbed myself as I read. I couldn't help it. I looked over guiltily at Tom as I did that. He just smiled back. He looked like he was enjoying it.

When I was done he needlessly asked, "so that turns you on, does it?" I answered, "yeah".

He then told me to show him how I masturbated when I was a kid, with the pillows.

You said to put up a little objection, Julie, and it came very naturally. I told him it was embarrassing and I didn't want to. It was literally half true. I was embarrassed, and part of me didn't want to, but another part did.

"I don't care. You wanted this. Get going."

"No"

"Do it."

"No"

"Do it, or else."

"Or else what?"

"Or else we'll stop."

Well he called my bluff.

"Ok, fine."

I knelt up on the bed. I put one pillow where my tummy goes, and another pillow turned sideways and pushed between my legs as I hiked my nightgown up. I then draped across, my bare bum high, the sideways pillow pushing into me.

"Now what," he asked.

"Now I think about the book and I rub myself."

"Shall I read you bits of it?"

"Yes please."

He went to the beginning and started scanning. He then read out the first spanking scene, where Rachel is being spanked.

He read, "'Ow! Oooh! Oh do stop, please!' Rachel howled in shame and misery as Clem's great slab-like palm descended speedily again and again in a blur of motion upon her blushing, shuddering, buttocks."

As he read, I slipped my hand down to rub myself with.

Then he put down the book, leaned over to me, and started gently tapping and stroking my bum with his hand and asking me a series of questions.

He asked me, "What's happening to poor Rachel, Sandy?"

"She's getting a spanking" (as I said that, I squeezed my knees together and rubbed a bit harder)

"That's right. How is he spanking her?"

"Across his knee, on her bare bottom"

"Is it a hard spanking?"

"Yes. Really really hard"

"Who else is watching?"

"Jacob and Simon"

"Are they enjoying the view?"

"Yes"

"What do they see?"

"A naughty girl getting a good hard spanking that she deserves."

"You're a naughty girl"

"Yes."

"What do naughty girls get?"

"Spanking"

"What kind of spanking?"

"A hard spanking, on their bare bums."

"That's right. And what else do Jacob and Simon see as Rachel gets her hard spanking from Clem?"

"Everything."

"Tell me what, specifically, they see."

As he asked that, his hand started lightly slapping right near my pushed up pussy. I squeeze my knees together more and push my bum up higher.

"Her pussy," I said.

As I said that his hand dropped onto my pussy and it sent an electric jolt through me.

"Oh Fuck!" I cried out.

"What do they see, Sandy?"

"Her pussy!"

"That's right, they see her little pussy, wriggling and jutting out as Clem spanks her so hard, just like your pussy is doing now."

As he says that he fingers me and it totally takes me over the edge. I scream as I come, and my body is shaking all over. I have a bad habit of swearing as I come, and the harder I come, the louder it is "oh fuck, Oh Fuck, OH FUCK, OH FUCK!" I'm almost laughing at how intense that orgasm was. I felt like it was 15 years in the making.

I come down from it, on my side a bit, still clutching the pillow between my legs.

Tom said, "Holy shit."

"That was the BEST orgasm of MY LIFE," I told him.

"I can see that."

"You're amazing," I told him. "You can make love to me if you want?"

"No, no, no. You need time to recover. I'll run you a bath."

Ohhhhh. So sweet!

I just lay there in bliss on the bed as he ran it. I felt so completely satisfied, from the top of my head right down to the tip of my toes.

Tom put me in the bath and he undressed and hopped in with me.

We had a talk about what just happened. He said he understands now how intense my fetish is. He also said that he loved to be able to make me cum with mostly just his words. I agreed. He said we're definitely going to explore more, and that we'll anxiously await our next homework assignment from you.

Thank you so much, Julie. Great choice for homework.

Amazing, amazing, amazing.

Sandy (and Tom)

Well that went as well as anybody could have expected!

My gosh. That sounds great you two! I'll be interested in your unique take also, Tom.

Julie

Tom then writes,

Yeah, it was fun. She has it bad. It was good knowing that I knew she was deliberately going to resist a bit, and that she has her safeword, so I had no problem ordering her around. It was what she wanted, and I could see that it excited her, so it was fun and did not feel abusive.

It was king of clever that you had me tapping on her bum so gently, because I felt like I wanted to hit it a bit harder.

It was a good passage to focus on because it seemed to have a lot of elements that turn her on. Just by observing her reactions as she read it I could tell what excited her the most, which was the hard beating and the pussy exposure to the onlookers.

When I read the short passage, all I had to do was press her on what was going on, and she turned herself on telling me. I really barely brushed her pussy from behind and she came.

You also told me to tell her that she was a naughty girl, and she was being a naughty girl, so that was easy. I kind of enjoy her being my naughty girl, so that was fine.

Good first exercise. Looking forward to more.

Tom

I'm kind of winging this as I go with these exercises for Sandy and Tom, so getting that great feedback really keeps me stoked! I already have a good idea what their next exercise will be 😈.

I'll detour a bit on my next blog entry and share some of Sandy's out-of-print "Ellen's Story" book so you can read the full passage that Sandy read aloud, and more.