Sandy's Story - Anal and Spanking

Sorry I've been so slow posting about Sandy and Tom, the couple I've been coaching on how vanilla Tom can spank spanko Sandy. Had my own spanking in there that I needed to blog about. But the net result is that I'm at least a week behind where we currently are.

Where we left off was that Sandy and Tom had just completed their first assignment - see Sandy's Story - First Assignment. Sandy was required to read aloud to Tom parts of her favourite spanking novel she acquired at age 13, and then to demonstrate to Tom, to completion, how she masturbated to it. Sandy used the face down, butt up, pillow humping position for her masturbation. This allowed Tom to encourage her with gentle pats to her bottom and brush-bys to her bum hole and pussy as he made her describe, out loud, what she was thinking as she rubbed herself. Sandy is like me as she fixates a lot on the hyper-embarrassing exposure a girl is forced to endure during a public spanking.

For example, the below illustrations I asked lill jo to do for me is my "worst case scenario" for this.

First I am stripped to nude in a roomful of grinning men. Then, not only am I being spanked, but I am being spanked in public as the men laugh at my shame, embarrassment, and distress. And even worse than that, my private parts are shown off during it, as if it was nothing. And you can believe that with the force of the spanking, and despite my being clamped down, my pussy will nonetheless be opening and closing, pouting and pulling-in, all the way through my embarrassing ordeal. And this will be commented on amongst the men.

This is the embarrassment a girl feels during a panties down punishment. And you can't tell me that the pain of a spanking differs significantly with panties up or down. No, they are lowered for one reason, and one reason only: to shame a girl. In addition to demonstrating his dominance in his ability to spank the girl, he's also showing off his complete sexual ownership of her.

For example, this is a photo of me across another man's lap as his wife takes the photo. This man did end up fucking me, doggy style, long and hard, and even sperming into me.

Different girls show more or less pussy during a spanking, due to anatomical differences. I show quite a bit. As this man had me across his lap, his fingertips brushed across my pussy lips as he rubbed my ass; and when he spanked my left low ass and high inner thigh, sometimes the tips of his fingers wrapped around and whipped my pussy lips, entirely "by accident" I'm sure. The extra attention there drove me crazy.

Sorry about that! Got carried away explaining that. Phew. Back to Tom and Sandy!

The first assignment was very successful, so I quickly made up a second assignment for them. Sandy had mentioned that she fantasized a lot about anal play, but she was uncomfortable asking Tom. I have no equivalent discomfort! As well, I wanted Tom to learn where and how and how hard to spank Sandy with his hand.

Hi Tom, Sandy,

Here is your next exercise. You are going to explore sensations associated with anal play and spanking and communicate throughout.

This is NOT a spanking, it is an exercise leading up to one.

Sandy: I want you to prepare yourself as follows. Have a good bath or shower and get squeaky clean. Pay particular attention to your anal region including inside (ask me if you need help here). I want it clean enough to eat off of and nice and empty. Wear your simplest full cut panties. Wear a skirt and whatever feels comfortable on top. No makeup. Nicely fresh faced.

Together, find a very comfortable place for Tom to take Sandy over-the-knee (OTK we call it). Someplace where Tom is sitting comfortably, and where Sandy can drape herself over his lap where both her legs and feet and her chest and head are supported. Side of the bed? Middle of the couch?

Sandy, make sure to have some water-based lube and tissues at hand for Tom.

Get into position. Make sure both of you are comfortable.

Tom - raise Sandy's skirt and arrange it well up over her back. Then slowly pull her panties down to Sandy's knees. Sandy, you may lift a little to assist in their downwards passage. Sandy, show your appreciation by wriggling your butt in delight.

First, I want you to explore some anal play.

Tom - Sandy is highly anal erotic. It often goes hand in hand with the spanking fetish. Even if it freaks you out a bit, I want those Big Girl panties on you. Part Sandy's cheeks and dribble a bit of lube on Sandy's anus (not too much, start conservative). Massage the area around her anal entrance with your fingers and the lube. There are many, many nerve endings around here, exceeded only by her clit, and equaled by her vaginal entrance.

Sandy - show your appreciation for Tom's efforts by wriggling and moaning. Now is not the time to hold anything back. I want that bottom hole begging for what comes next. In fact, I want you begging for what comes next. Ask Tom to please put his finger inside there. Use whatever words for that part of your anatomy turns you on the most. Be explicit.

Tom - take mental note of the words Sandy uses the most. Spankos are often triggered by certain key words. It's different for everybody and there's no way to know in advance. Some will get highly excited by the coarse "asshole". Others it will turn them right off. Some will love "bottom hole", others will get turned off by that. Listen to the words Sandy uses. Make her beg for it over and over as you continue splitting her cheeks and massaging that area so that all the words she uses come out.

Sandy, Tom - you're not role playing. You're communicating. Be honest and open about what you're feeling and doing. If Tom is too light or too hard, let him know.

Tom - there's no right or wrong here. Each girl will be different. And Sandy might not even know what she likes, physically, yet. So explore, try different things, and communicate openly during it. It will be a little embarrassing for Sandy, so you may need to coax her a bit.

Tom - when you think Sandy has begged for it enough, add some more lube and insert a finger in, slowly and gently. It's going to hurt Sandy a little, but once your finger is inside her anal ring will relax around it. Do some twirling motions and some in and out motions. Eventually, progress to having your finger inside her right to the hilt. Make sure your fingernails are super short. (Sandy, you make sure you're clean inside). When she's loose, you can pull your finger all the way out, and push it all the way inside again.

Sandy - as he is doing it, verbally express your thanks to Tom over and over again for doing this to you. Be explicit in how you are thanking him. Use words that turn you on so Tom can know them.

Sandy - if you are comfortable and wish to try, you may ask Tom for two fingers at once.

Tom - you may need to apply more lube as you go as her bottom hole may be a bit greedy in sucking it up.

There is no end goal here, just sensations and constant communications.

Now let's move on to the spanking. Take a pause to allow Tom to wash his hands. Sandy, please wait with your nose in the nearest corner, skirt up, panties lowered, as Tom does this.

When Tom returns, resume your previous positions.

Tom - I want you to start gently spanking Sandy. Please don't use the word "hitting" or "striking" to describe what you are doing. When it's a consenting adult with a spanking fetish asking to be slapped on her backside in this manner, it's "spanking" and you're delivering "spanks".

Do some pre-spanking exploration with your hands. Feel where Sandy's tailbone is. You want to stay well away from that. Feel at the top where her butt ends and her waist begins. Stay below that. Feel around to her flanks where the fat and skin thins. Stay inside of that area. Feel where her thighs start going into the backs of her knees, stay well above that (though the meaty part of the calves is ok too). All those areas outlined are fair game. Including the insides of her thighs (they are VERY sensitive), and the insides of her bum crack. Pussy and anus are also fair game for gentle spanks, as are fronts of her thighs (generally when standing - do a few spanks there at the end when you have Sandy standing and holding her skirt up for you - enjoy the view of her wriggling pussy).

Now, make an open palm, fingers together, gently cupped, and begin spanking Sandy.

You are not only using safewords this time as you are not roleplaying. All words are to be taken at face value. However, let's do get practice with the yellow safeword. Sandy can use that (in addition to any other words this time, not instead of) to indicate when the intensity has gone a touch over her sustainable comfort level.

Tom - experiment with different locations for the spanks and various different strengths and techniques. Tom, Big Girl panties on, I want you to go hard enough and sustained enough that Sandy says yellow.

Remember, yellow means take it down a bit, not a lot, and keep going. A yellow at one point in the session might be at a different point later in the same session.

Sandy - give Tom honest feedback. Ask for it harder or lighter. To ask for it harder, say "green". Ask for it in different places. If this were a "real" spanking of your fantasies, let him know what sorts of spanks and where on you you would want most of, some of, a little of, and not at all. Sandy, do not go nuts. We are not trying to find your limits here, just what a good punishing strength and pace is for you.

Tom - again, there is no absolute right and wrong. Every spankee is different. You are learning the ins and outs of the delightful little spankee over your lap. Also, spankees will differ a bit each time they are spanked. Some times they will be able to take more, and sometimes less. Carefully observe Sandy's reactions. Her movements, her breathing, her perspiration, her scent. Eventually you will take Sandy a little beyond her comfort zone (she will want you to), but not this time.

For myself, I like the majority of the spanks near the undercurve of my butt. I don't like a lot of straying and will get turned off if there is too much of that, but I do like some straying, absolutely. Find out if Sandy is the same, or different, and how.

In each zone you spank (try them all), increase the strength and speed gradually until Sandy says yellow. It's about strength, speed, and duration. Try different combos to get that yellow. Sandy, you will have to spread your legs to allow Tom access to inner thighs and pussy (and, yes, I want Sandy's pussy spanked gently to yellow as well). Don't neglect nearer the insides of her bum crack. Part her cheeks for that. Get a yellow on her inner cleft. Also, directly target her bottom hole, and spank that as well with your fingertips, again until yellow.

As the last thing, have Sandy stand in front of you, holding her skirt up, and give her spanks to the front and front insides of her thighs until yellow as well.

Sandy - all the way through the spanking thank Tom for what he is doing using explicit words that trigger you and turn you on. Tom, take note of Sandy's words to use back on her in future. Note especially how she refers to her bottom. Ass, butt, backside, bum, ... same with vagina, pussy, cunt.

After it's all said and done, I think a big "Thank You" to Tom is in order. Sandy, go onto your knees in front of Tom, free him from his pants, and give him your very best blowjob until he comes into your mouth. I'm not sure if you're a spitter or a swallower, Sandy, but from now on you are a swallower. Hold Tom's ejaculate in your mouth, look him straight in his eyes, then swallow it all down gratefully. Tom will understand this as a big thank you. No orgasm for you this time, Sandy. You're to go to bed hot and horny that night.

Have fun, kids, and let me know how it goes!

Julie

What do you guys think? A good exercise for them? Sexy to boot!

The kids wrote back straight away:

Oh my gosh, Julie!

Tom and I have gone over this in detail. We printed 2 copies so we each could study our parts. We also read it out loud together (I read it to him).

Tom says he is game and will do his best. He's well prepared. He read that Vivien book, he watched the Jillian Keenan videos you referenced, and he read that chapter in your book where Beatrice and Julie discuss spanking. Did I mention how amazing Tom is?

Everything you've written is so explicit. Who does that? You do. We're determined to do this exercise line by line.

And, yes, if you wouldn't mind please writing me back privately on how best to "clean myself out" back there, I would appreciate it.

Sandy & Tom

Keen and enthusiastic kids. I love it! I wrote back some extra instructions privately to Sandy on various methods to get herself cleaned out. I'll spare you the details!

It took them a couple of days to get to this exercise, but then they did and they wrote back.

We did it! Yay! Big success.

I suppose you'll be wanting the blow by blow for the blog? Of course you do. Tom and I are writing this side by side.

Thanks for the cleaning out email. I felt very clean and confident. I got squeaky clean and fresh faced, and dressed in a white blouse I tied up at the midriff (Britney style, but without the Britney bod I'm afraid 😊), and a red plaid skirt I own (what spanko girl does not own one? Always hoped it would send a message to the guys I dated). Had simple full cut cotton panties.

We used the three-seater couch, and Tom sat in the middle and I draped over him. Tom raised my skirt, which was already super exciting. I'd been across Tom's lap before for what we call a spanking attempt, but neither of us knew what we were doing, or what was expected, and it did not end well. This time, we both knew exactly what we were doing, thanks to your email. Tom had his printout right beside him. I knew that the raising of my skirt was the start of a nice long exploration, and so I was excited. Tom says he was excited as well, half for himself, half for me. He reached into the waistband of my panties. I raised my bum up as he lowered them. I gave him a saucy wag. He left them around my knees, as instructed.

Tom had a little bottle of lube right beside him. He spread my bottom cheeks and dribbled the lube right onto my hole. OMG. I knew what was coming and I was excited. I'm a total virgin there from a boy point of view (Of course, I stuck all sorts of stuff up there over the years: pencils, crayons, tootbrush handle, hairbrush handle even). Tom circled his finger all around and brushed back and forth and up and down. As you said I should, I made a point of showing my appreciation by wriggling my bum and pushing up into his finger. I told Tom how good it felt to have his finger there. Something like, "Oh God, Tom, I love your finger there."

We're going to try to reproduce what we said to each other. We're having fun arguments over who said what when, but in the end it'll be close enough.

"Are you excited?" He asked me.

"Oh yes!"

"What do you want me to do with my finger next, baby?" (Confirmed: he was reminding me I needed to beg for it.)

"Please put it in me, Tom?" (I was supposed to use more explicit words, I know, but I was a bit embarrassed, and I thought it was squishy sexy to have Tom "make me").

"Put it in where?" he asked, all innocently.

"Please, Tom, please put your finger deep into my... dirty little bum hole." (yes - that is what I call it that turns me on the most)

"Is that what you really want? You really want my finger deep up your dirty little bum hole?" (LOVED that Tom shot that right back at me. And, as an aside, Oh my gosh, Julie, you are so right. Tom using just the right words turned me on so much.)

I thought I'd try some other words that also turned me on.

"Yes, Tom, please give me a good hard finger fucking right up my ass."

"Is that what you want, naughty girl? A good hard finger fucking, right up your ass. Deep into your dirty little bum hole?" (Tom is getting the hang of this - he said it's a "simple algorithm", he could make an AI do it.)

"Yes Tom." (I found it sexy to use his name, as in, it's not just anybody doing this to me, it's Tom doing this to me).

Tom slipped his finger in, penetrating my bum hole.

"Is that ok?" He asked, checking in.

"Yeah"

"Does it feel nice?"

"Yeah"

Tom pulled it out, re-lubed my hole, then pushed it in again, no more than an inch deep at first. He did that a few times, pulling all the way out, then going back in again.

"Do you like that?"

"Yes, Tom."

"Are you ready for me to go deeper?"

"Yes please"

Tom pushed his finger in. He says he went all the way to the hilt.

It felt... amazing. I couldn't believe Tom had his finger buried as deep as he could up my ass.

"Just hold it there, ok?" (it hurt a bit, and I wanted to get used to it)

I squeezed and relaxed my anal muscles around his finger.

After a bit he very gently started circling it inside of me. "Still good?" He asked.

"Yes"

When I was comfortable I asked, "please would you fuck my ass with your finger?"

"In and out?" He asked.

"Yeah, but not all the way out, ok?"

He pulled out until just the tip was in, and then pushed all the way back in again. At first he went slowly and then quicker and quicker.

"Yellow" I said. (Our very first yellow. Yay!)

Tom slowed right down but kept going.

"Too rough?"

"A bit. Like that is nice. A bit more maybe."

Tom sped up a bit.

This yellow safeword thing is genius, Julie. It's like letting him read my mind. It's just, communication, right? Tom says that it takes the guesswork out, which he really appreciates. He can see that he'll pretty quickly learn where I like it, and what is a bit beyond. He also says that he hardly even needed the yellow, because he could tell from my body that I was there (in retrospect).

"Is this what you want, Sandy?" He asked as he fucked me. "A nice deep finger fucking right up your ass? Right up your dirty little bum hole?"

"Yes Tom"

"Tell me what you like."

"I like it when you finger fuck my ass. Right up my dirty little bum hole."

"And what does that make you?"

"A dirty, naughty, dirty, dirty, girl."

"And what kind of fuckings do dirty naughty girls get?"

"Ass fuckings."

(It's so nice that Tom is so verbal with me - I realize it's such an important part of this kind of play, something I didn't fully understand before. Tom says he's learning that what's going on in my head is 90% of it).

"Shall I try two fingers?"

"Ok"

He tried pushing two in, but it was pretty uncomfortable so I yellowed out of that one and told him we'd need to work towards that. (I told Tom, just now, what I actually want to work towards is getting his cock in my ass. Tom says he's game. What lesson is that, Julie? 😊)

Tom got some tissues and wiped my bottom for me (embarrassing).

He stood me up and he sent me to the corner with my panties still around my knees. He went to the bathroom to clean himself up.

My skirt had fallen and Tom did not order me to keep it raised. It's not the same when you have to do it yourself, but I did. Tom has that feedback ("check", he says). By the way, first time in the corner for me. I like the feeling. Mind you, it was super short. I might not like it if I got a lot longer.

Tom had brought back a damp washcloth and used it up between my cheeks as I stood there (embarrassing - I was getting my ass wiped like a little kid).

We went back to the sofa and resumed our positions. It was time for my spanking.

We won't go into every detail, but suffice to say that Tom was very, very thorough. He gave me a light spank all over first. Then he focused in on various areas. He started light and went harder and harder and faster to that one spot. We did a scale of 1 to 10 (sorry, Julie, we thought the number scale was better, hope that's ok?). I kept giving him feedback, and his goal was to get to 10, which is the same as "yellow". I also have a letter grade to each place he spanked, from F right up to A+. Flanks and way high got an F. Everything else was A or B. Fleshy undercurves were the only A+.

At one point he made me spread my legs. Needed to lose the panties for that. Inner thighs got an A, but also a pretty early 10. Pussy got a surprisingly high B+, and a super early 10. Crack and bum hole smacks got an A (because of the shame factor), and a middling late 10.

Tom went back over a few places "just to make sure he got it". I suspect foul play. (Tom says he couldn't remember about some places and needed to double-check. Sure)

We spent a long time like that. I got very thoroughly spanked, absolutely everywhere. And I mean everywhere.

Tom was surprised how hard he needed to go in some places to get me up to a 10, and how soft in others.

Tom wanted to be thorough so he made me stand up in front of him, and we kept going, as I held my skirt up, all around the sides and fronts and inside fronts of my legs. Also just above my pussy, and right on my pussy from the front. He took his time, working me to a 10 on each of those areas. So embarrassing.

"How about your tits?" Tom asked at one point. You had not said anything about those, but we figured it was an oversight, so Tom had me undress on top, and he slapped my breasts also, from all angles. I am fairly big on top, and Tom held a tit in one hand while he slapped it with the other. He did tops, outsides, insides, undersides, and nips, all to 10, both sides. I gave it all an A. I like having my titties spanked.

You won't believe how red I was all over by the end. Tom said it was like I had a painted on pair of skin-tight, camel-toe showing, shorty red yoga pants on the bottom, and a red bikini on top. Tom was also surprised that it was all gone within an hour. The fact that it cleared up so fast, with no lasting damage, was a comfort to him. For my part I told him I was disappointed in that, and wanted marks that lasted longer to be proud of. He says now he'll see what he can do, provided it's safe.

Of course, I had to do Tom's "thank you", so I did that just as you instructed, Julie, on my knees in front of him, with his legs spread out, pants off, sitting on the couch.

I asked Tom if he could be a bit more rough with me, and push my head down onto his cock more, and make me gag a little. I had never asked him to do that before, though I wanted to, every single time. He obliged me and seemed to enjoy it, even thrusting up into me at the same time. He came in my mouth. Julie, I was always a swallower, because it was the one bit of shame I got. This time I made a show of showing it to him and then swallowing it all down. (Tom says it was extra sexy having me be like that now that he knows it's what I really want).

I did go to bed horny. I "tested him" by begging him for sex, but he was strict and said no, on your authority. I asked him if I could at least masturbate, and he said no to that as well. It's exciting that he did. Looking forward to the day he's going to spank me for even asking.

Another great exercise.

Tom asks, "what's next, coach?"

Thank you.

Sandy and Tom

Fantastic, eh? The power of just open and honest communication. But also, not to underestimate Tom's willingness to "go there" without which none of this would have been possible.