The Art of lill jo

As all my regular readers know, I have a very devoted blog friend who goes by the name of "lill (Ms Julie's punished sketch slut) jo". lill josephine (as I like to call "her") has her own blog and tumblr site and contributes her sketches to those who ask (and she always seeks my permission, which is sweet).

I love his work so much that I thought I would present a "best of" gallery here with my comments. There are very many images on this one page so it may take some time to load them all. They are all high resolution so you can enjoy them as a slide show as well without my commentary. Please enjoy either way!

Fun With Trainers 

As many of you know, I have hired a series or pretty young women to be in-home personal trainers for my husband. I've always managed to bring them willingly into, to a greater or lesser extent, our kink. Over the years I've requested many images from lill jo either illustrating actual events or fantasies based on actual events.

This first is one of my all-time favourites. It captures a moment in time where one of david's fitness trainers gave him a spanking in the living room while I watched. lill jo and I went back and forth to ensure it was as accurate as possible. This was early days for david and my did he blush (both sets of cheeks)!!!

Trainer 1

Below we have david doing a "pants down plank". His trainer has a stopwatch counting down the full minute. She encourages him to hold it by alternating swats to his rump and teases of his erect cock. Lovely and true to life scene! Pants down plank is still a go-to move for his trainers.

Trainer 2

Here's another where she had david running stairs without pants. Each time he got back to the bottom she would make him bend over and smack his ass with her crop. His penis looked very funny as it hopped and flopped down the stairs as we watched!

Trainer 3

And here is one in the gym, with his trainer and I alternating smacking him. I love the exercise ball because he really is that exposed. And that includes his shy bottom hole which is always exciting for me to see as that is his fuck hole. Here his trainer is targeting it, in fact (it is a tempting target).

Trainer 4

Here we see david taken in hand for one of his regular (nude) weigh-ins by his trainer. He just can't seem to shed those few extra pounds. He will be consequenced. And yes, he always gets throbingly erect in a female dominant type situation. How embarrassing for him and fun for us!

Trainer 5

Here is a much earlier one, before I decided to retain the services of young ladies for his training and did it myself. And let me tell you, eating a full bag of chips earlier in the week plus a weight gain? It's the strap for him!

Trainer 6

Sometimes the threat of feminization in addition to the hairbrush can be a great incentive to get him to work harder during his training sessions. Here his trainer followed through. Unlucky for david that my sister was visiting at the time and got to see it all. And believe me, that hairbrush got used as well. Sue and I could hear the smacks and howls from my little girl emanating from the basement gym!

Trainer 7

I think this one might have been lill jo's fantasy of my sister Sue, myself, and his trainer putting him through his paces, which in this case first includes tenderizing his bumhole and then publicly fucking him like a whore. Never happened but should have!

Trainer 8

A little workout on the treadmill, anyone? We don't have a treadmill but do have an elliptical trainer, and this scene is therefore not so far off reality. His trainer encourages him to pick up the pace with her switch to the backs of his legs. He can run faster or be switched in his panties. His choice.

Trainer 9

Here he is all femmed up for his training session. So humiliating to be made to exercise like that by his fitness trainer!

Trainer 10

Of course, sometimes his trainers are curious about our lifestyle. I am happy to demonstrate and have them participate even. For example, here is my husband all dolled up the way I like him prior to a session with the strap-on. I mean, if he's going to be bent over and fucked like a woman he should be dressed like one too.

Trainer 11

We'll start by cleaning him out. She needs to be taught that procedure.

Trainer 12

Next is his spanking to get him in the right mindset for what's to come. I'm happy to let her administer it.

Trainer 13

Sometimes they are real scorchers, these pre-sex spankings. I'm glad to see she's getting into it in the spirit intended. Don't want him putting up a fuss when it's time for him to receive some cock. The brassiere is a "go to" for me. Panties are just too close to men's underwear. They can lose impact over time. A bra with C-cup inserts? Exactly.

Trainer 14

Now it's time for the main event. He can suck on my cock as I coach his trainer on how to give it to him in the ass.

Trainer 15

He's been a good boy. He's allowed to clean out my asshole as his trainer milks him.

Trainer 16

If course, it's always "down the hatch" after a good healthy ejaculation! She was happy to feed it to him.

Trainer 17

Here's a nice little fantasy where I put him into a cock cage until his diet and exercise improve. His release will be entirely at the discretion of his trainer. As you can see, she is quite delighted with this new motivational tool, as am I. david, on the other hand, is mortified that this young lady will be in full control of his sexual release. He had best work hard if he expects her to allow him to ejaculate anytime soon.

Trainer 18

It's also fun to have him femmed up and whipped with a wire coat hanger by his trainer. That too is highly motivational.

Trainer 19

In this true to life episode, I put david into his bra for the first time in front of his trainer. I also decided he needed the belt and, as I was not at all interested in his complaints, a ball gag. This is quite accurately depicted.

Trainer 20

And finally in this category we had his trainer over for a nice chicken dinner that included a cum-sauce for him and a glass of very special pale yellow wine I made for him myself. She got a kick out of it and he was soooo embarrassed!

Trainer 21

Fantasy Scenes

One of my favourite things is to dream up fantasies along with my various e-subbies. Sometimes lill jo brings them to life for me.

In this first one, some poor boy whom I imagine is a fraternity pledge is going to be receiving his paddling from his frat's Sister Sorority right in the middle of the campus. He obviously somehow got on their bad side. Perhaps he was fresh with one of their pledges? Of course the sorority sisters find it hilarious to make the male pledge dress en femme and ball gag and restrain "her" for the big event.

Fantasy 1

Not so fast. Didn't the pledge bylaws require this to be a bare bottom paddling? Let's get those panties right down for your pledge paddling. Never mind all those college kids. They'll hardly be able to see anything as your penis is sooo tiny.

Fantasy 2

Fortunately the campus cops come before his ass was completely blistered and let the young man down.

Fantasy 3

Someone is in big trouble though. The boy cannot be a rat and takes full blame, saying he likes to dress in women's clothing and asked the ladies to tie him up and paddle him. Well, the University takes a very dim view of that, and his week-long Viagra-fueled punishment will be made to fit the crime!

Fantasy 4

School Days

One of my e-subbies had a fantasy about school days that lill jo helped bring to life along with some of his own.

Do you suppose these two boys will continue being smart asses in Ms. Julie's class after this? lill jo knows that this particular method of restraint is a favourite of mine with my husband. david spends a lot of time with his penis and sac stuck behind his legs like that. Boys are so vulnerable when they are whipped in that state, and they look like girls from the front!

School 1

When a boy's been very bad in Ms. Julie's class he must strip to his underwear and apologize to the whole class for the disruption.

School 2

After that it's across Ms. Julie's knee to have those underpants lowered for a bare-bottomed blistering in front of the whole class.

School 3

Then it's underpants down corner time for the naughty boy until the bell rings, and let that be a lesson to you all.

School 4

Of course, if you students keep up the sniggering for too long, you will get a taste of some of the same.

School 5

And if the in-classroom discipline doesn't seem to cut it, there's always the cane at school assembly. If the boy wets himself in fear either before or during his caning, he will be made to remove his soggy underpants and then clean up the mess himself while everybody watches.

School 6

Day to Day Life

lil jo has done a number of images for me that just reflect my day to day life with my husband. One reason we are into this is that my husband is no great "cocksman". A half-dozen weak thrusts is all I could ever expect before he blew his load, assuming he didn't blow his load on my pussy before he even entered, that is. In fact, forget pussy, david even jizzed his pants when kissing a girl in ninth grade!

Life 1

When it's my turn, well, suffice to say I am always hard and ready and fuck him a good long time to make up for his inadequacies whether he likes it or not (though he keeps coming back for more, I must be doing something right!)

Life 2

I do enjoy teasing him to the point of distraction, but then denying him. In that case, I do love seeing him squirming where I put him, his back against the wall, his hands on his head, his throbbing hard and drippy penis getting absolutely no relief whatsoever. Especially entertaining when girlfriends come to visit. Or, even worse as far as he is concerned, emptying his balls and then using that paddle I have beside me. I do that when I need him to mind me.

Life 3

Of course, he is no stranger to the hairbrush. He's the one who first handed me the hairbrush, so I aim to now make each and every session across my knee a memorable one for him. Be careful what you wish for!

Life 4

Of course, I also like to vary the implements and positions. Diaper position with implements is an especial favourite of mine. I especially love this position when other women are present to watch.

Life 5

When I have more planned for him, this position lets him see what's coming next. If he's looking scared, that's because I'm sporting Adam which he knows to be a real challenge for his mouth and anal sphincter. A good sound strapping first, though, with the promise of more to come if he misbehaves during sexual relations, works a charm to have him accept the inevitable.

Life 6

Here is another depiction of the same. A real bun burner! I enjoy banding his panties around his ankles so that he has a clear view of them as I strap his ass and thighs. Panty trained and strapped hard by a capable woman: what's not to like?

Life 7

And closely related to this position, and hard to pass up, is "the facial". Notice the well-spanked bottom, the dildo in his hole, and the cock rubbing. It must all go into his mouth or else. Well, he wanted a release...

Life 8

The below is a very common position and a very common situation in our household. When I feel like catering to his perverse needs he is told get himself ready, to slip into his panties, lie down on the bed across several pillows, lower his panties to his knees, and wait for me to come up. He'll then get his much desired strapping and pegging. Afterwards I'll straddle his face and he'll be required to service me orally to orgasm. First pussy, then ass.

Life 9

Often our domestic scenes will involve discipline for some imagined or actual shortcoming of his. Corner time usually precedes discipline and follows it both. I make it a point to administer corner time in the brightly lit living room. For discipline he almost always is required to wear punishment panties. I try to be creative with corner time and sometimes "humble him" by forcing his genitals behind his legs and belting his thighs together so he cannot release them. A butt plug in his anus can add to the punishment. It had best not fall out! Then it's hands on head and nose in the corner for however long I say. We have even had visitors when he was in exactly this state (my kinky sister and her friends in particular, and they got to watch the butt plug removal and the spanking after!)

Life 10

Corner time has so many possibilities. Once I roped his genitals up to his neck and took a light switch to them. lill jo saw fit to add me eating a nice purple plum in honour of david's purpled plums. Oh, and in case you were wondering, no I do not run around exclusively in stiletto heels and lingerie! lill jo is allowed some liberties (though I often have to remind him to not undress me for authenticity's sake, and to refrain from any unwarranted femming up of my husband!).

Life 11

Sometimes I can be very strict with my david. For instance, a good old fashioned country switching followed by corner time.

Life 12

The nice thing about corner time is that it's satisfying his perverted needs, with very little involvement from me. A heavily vibrating dildo up his rump keeps him amused for an hour or so and keeps his cock dribbling down the backs of his legs as I relax.

Life 13

Another great thing about our lifestyle is that we include housework as part of our "scenes".

Life 14

I find it much easier and more fun to "make him" do housework and punish him afterwards for real or imagined failings then to do it myself. Ha ha!

Life 15

Here is david doing some "corner time" against the wall. Freshly spanked. Punishment panties lowered. Arms behind his back fastened with sticky tape round and round. He's made to hold a coin up with his nose. If the coin is on the floor, or if the sticky tape is broken at all, it's another spanking and a restart of his timeout from the beginning. And I'm dead serious and he knows it.

Life 16

Sometimes a timeout can be in an even more humiliating position. This is actually a fairly common one where he must hold his cheeks apart to show off his slut hole, usually before or after a fucking. My sister has seen this view of him!

Life 17

And this is often what happens to him when he finds himself in this position, regardless of who is there to see it, regardless of how well used that hole has been or is about to be. A good whipping to his hole followed by overly vigorous anal intercourse with an overly large dildo is what I call a "punishment fucking".

Life 18

Oh no! More corner time. Garter and hose, panties lowered, thighs belted tightly together, balls out, nose in the corner! One hour, mister. If you move, you start again after a strapping and a ball switching.

Life 19

And again. He spends more time in timeout than you can even believe. That's a belt around his thighs, clamping his legs together so that his cock and balls are just where I want them. Plus it makes standing straight a trifle difficult. And yes, that is a ginger root up his rectum. Ouchy!

Life 20

I also own a stool and a fat dildo I've fastened to it. Sometimes he must perform penance there - feet dangling, hands on his head - so that he feels the full measure of that dildo in his rectum for as long a timeout as he has earned.

Life 21

He may get home from work and find that his next outfit is already laid out for him.

Life 22

Isn't he cute with his little dress, wig, and breast forms. Hopefully I can confine the use of this hairbrush to your hair, baby.

Life 23

Or maybe the dress can come off and you can enjoy a bit of a teasing in the kitchen while I cook for you? Don't think there will be an ejaculation for you, though honey, unless you manage to ejaculate in your panties as you're across my knee getting the wooden spoon to your saucy behind while I'm waiting for the meat to cook!

Life 24

And you better make sure you're on top of your chores, honey. If not, a strap to your backside will certainly remind you.

Life 25

Public Play

It's always fun involving other women in our play. I have a very accommodating sister for one, and she can often scare up some kinky friends as well.

This sort of "forced" feminization and spanking punishment can happen even when visitors are present. They may even be willing to lend a hand. Pulling his panties tight up his ass crack is painful for his genitals and makes him acutely aware of his exposed anus as the material tightly bisects it. My British friend here enjoys caning "schoolgirls" like david. She got her chance soon enough and there was precious little mercy shown!

Public 1

I very much enjoy taking david out shopping for women's underwear. On one very notable occasion, at Victoria's Secret, I had him trying on bras with the help of the salesgirl. She was very amused by it all, and did a terrible job of shutting his change room door. He was laughed at, for real, by both staff and clientele.

Public 2

Sometimes I put him in compromising positions and invite strange women over to see. It's always a big laugh for my friends. The brassiere is particularly humiliating for him.

Public 3

Here is one of lill jo's fancies. The boi's wife seems very upset with him and he will be cleaning his friend's house as a result, sulky or not. She has full permission to discipline "her" as she sees fit.

Public 4

And along the same vein. I like how much he is blushing, how stern his wife is, and how racked with laughter is the friend! This is how to put a husband in his place!

Public 5

If he's reluctant to get the housework done, or does a poor job, well you know what will be the result of that. A sufficiently strict hairbrush spanking that he will be well motivated to do a better job in future.

Public 6

And here's david at a little party organized for his benefit. He must present himself en femme, ask each woman in turn for a spanking with the hairbrush, and at the end must submit to a very publicly delivered session of anal intercourse from his wife. Will he ever live this down? I know for an absolute fact women love to see a man put into lingerie, spanked to frantic kicking and tears, bent over, fucked hard and crying like a girl on every hard thrust, begging for his public disgrace to end. Women are cruel, especially in a group!

Public 7

More than once my david has had to be fucked while other women watch. In this case it is my sister seeing him put through his paces after he'd been whipped.

Public 8

Once my sister and I milked him into a dish. He was then made to crawl into the corner carrying his cummy dish, and then lap it all up like a bad little doggy. And yes, this was extremely embarrassing for him!

Public 9

What if another couple dropped by after one of his punishments? Corner time is inviolable, not matter who is there to see it.

Public 10

Should I dress him en femme and show him off to the couple? He had best curtsy, or else!

Public 11

And wouldn't our neighbour enjoy my little doggy woggy?

Public 12

And finally, sometimes our scenes are extremely public, such as the time I spanked him at the nude beach with my flip-flop. "You WILL NOT stare at the naked ladies, young man, and you will certainly NOT become aroused doing so!"

Public 13

My Man-on-Man Fantasy

I've always wanted to involve another male in my husband's domination, however that is just fantasy for now. Fortunately, lill jo can bring it to life for us.

First I'd tell him to go home and cook dinner for two. He'll be serving. I've already laid out his outfit on his bed. Yes. Panties, bra, stockings, heels, and a short maid's dress.

Man 1

There we go. All dolled up!

Man 2

Meet my friend, Hank, david. You'll be cooking for us tonight. Let's see a proper little curtsy now.

Man 3

Can you believe he burnt the dinner??? Perhaps it was a deliberate little rebellion?

Man 4

Here, Hank, you talk some sense into his backside!

Man 5

Time for his punishment stool now.

Man 6

Up you go!

Man 7

Comfy, sweetie? I hope not. You stay there while I entertain Hank.

Man 8

How about some two couple action? A little paddling competition perhaps. Who can last longest?

Man 9

We could dress them both up before their mutual cocksucking.

Man 10

And then it's on. Who will last longest in this "69" competition?

Man 11

Oh yes, you have a visitor. Go down and greet him properly, with a kiss and a curtsy.

Man 12

He will be made to service our visitor. He complains, but I can see the bulge in his panties. Besides, I have the cane at the ready to deal with any disobedience.

Man 13

Don't think he'll got off lightly.

Man 14

Perhaps a ballerina costume would be nice. I'm enjoying watching this!

Man 15

Kiss my feet, boi, or my boyfriend here will paddle your ass!

Man 16

Not good enough. Across his knee you go, missy.

Man 17

The paddle is next. I need to prepare him for what's coming.

Man 18

Let me get it hard and ready, Hank.

Man 19

Now fuck him hard. Harder! OMG!!!

Man 20

Maybe two men at once? One for each hole. Now play nice, boys!

Man 21

I might invite my sister over to watch.

Man 22

Watch everything!

Man 23

Joint Cop Fantasy

Here's one we worked on together. Julie's next door neighbor boy who was hired to do some chores around the house was caught red-handed by her.

Cop 1

The boy needs a lesson. Julie keeps him dressed as he is and calls her brother the cop.

Cop 2

They discuss the boy's future in perv prison.

Cop 3

The boy decides summary punishment is better than jail. In that case, Julie goes first.

Cop 4

He may be having second thoughts!

Cop 5

But he still has a strict belting coming!

Cop 6

And now it's time to pay for the trouble he caused Julie's little brother. First suck on it.

Cop 7

Now take it.

Cop 8

The boy is sentenced to a month's service in Julie's house. Julie and her daughter are very strict with him.

Cop 9

And when Julie's brother comes calling, they make sure he is all dolled up for him.

Cop 10

And ready to service his needs.

Cop 11

Only another four weeks of punishment, boy.

Cop 12

An Unconventional Friend

I met a new friend who was willing to assist in domming my husband. This is what she looked like. How would david feel about getting domme'd by her?! I intended to find out.

Friend 1

I wanted to setup the scene so that she and I would walk in and catch him masturbating to internet porn.

Friend 2

First we'd give him a taste of the strap the way I like to do it. Shit, but she doesn't hold back at all!

Friend 3

But she indicated a particular interest in paddling him, and even brought along her very own fit for purpose paddle.

Friend 4

I thought I would finish him off in the wheelbarrow position. She gets a nice view of his anus and genitals, and I get to smack right down into his crack.

Friend 5

So, you like getting your rocks off in front of the computer, eh? Well you won't mind getting them off in front of my new friend, then. Right into the doggy dish.

Friend 6

Now eat it all up or it's another paddling across her knee!

Friend 7

Maid Fantasy

I had another e-subbie pen pal where we dreamed up a maid fantasy for my "daddy". I caught daddy in a lie and blackmailed him to accept a strapping from the maid.

Maid 1

After that, it was off to be fitted for his own maid's uniform and a solid day of housecleaning.

Maid 2

And here's the maid and I getting daddy ready to expose his dirty secrets to my Mom.

Maid 3

 Now it's the maid riding his face while Mom and I whip his ass!

Maid 4

Caught Masturbating

It's another little fantasy from a reader. I thought I'd show you how lill jo and I work. I first set out the scene and get preliminary sketches for my approval. Once they are considered a go, he delivers me the final product.

Here is my catching my nephew masturbating.

Caught 1a

Caught 1b

I make him lay there exposed while I lecture him.

Caught 2a

Caught 2b

Now he's in for a spanking.

Caught 3a

Caught 3b

He needs to be taught how to properly relate to women. The young next door neighbour girl can help with that.

Caught 4

Take it!

Caught 5a

In living colour.

Caught 5b

Whimsy

And sometimes lill jo just get a lill whimsical, such as this Picasso-style rendition.

Whimsy 1

Or taking hubby for a walk.

Whimsy 2

Flouncy little gurl!

Whimsy 3

Kissing...

Whimsy 4

Pretty serving girl.

Whimsy 5

The scullery maid gets a bit reluctant to put some elbow grease into her cleaning chores. A red bottom soon cures that.

Whimsy 6

And here's my husband hard at work on the dishes. How delightful!

Whimsy 7

Me and my daughter getting david ready to be presented as a gift on domme night.

Whimsy 8

Poor little baby!

Whimsy 9

Nice polka dot panties.

Whimsy 10

Sulky in the corner.

Whimsy 11

Forced to suck cock in his DDD breast forms and negligee. A delicate little tear down his face.

Whimsy 12

Looking pretty for his new "boyfriend"

Whimsy 13

Time to "perform".

Whimsy 14

Now this is being helpful. If he spills a drop he'll be licking it up and swallowing.

Whimsy 15

So sweet!

Whimsy 16

So bashful. That little panty does not cover a lot.

Whimsy 17

Cutey pie!

Whimsy 18

Time to go for a walk?

Whimsy 19

Oh no, silly. Out on the street with the other subbies.

Whimsy 20

Did sissy break the vase?

Whimsy 21

That's not good. Curtsy please.

Whimsy 22

Now panties off.

Whimsy 23

Time for some discipline.

Whimsy 24

Now go serve the men.

Whimsy 25

And my friend and I in the garden.

Whimsy 26

White or red?

Whimsy 27

Billiards, anyone?

Whimsy 28

Here's a nice gag for him. A few hours in that gets him ready for the real thing.

Whimsy 29

What if he's discovered? How humiliating would this be?

Whimsy 30

Oh come on...

Whimsy 31

A Visit

As a reward, I sent lill jo a naughty photo of me and asked him to masturbate to it, and then to be sure to write me telling what his thoughts were afterwards. Turns out he masturbated to the fantasy of coming to visit me in Toronto and stay a couple of days with my husband and I.

Here is lill jo after I picked him up from the airport. I had him en femme before he could even unpack!

Visit 1

He did want to give me his gift, though. It was a strap-on with a clit and anal stimulator attachment. Very nice. I would put it to good use this weekend.

Visit 2

First thing I did was make sure his bottom hole was well plugged. It would be kept that way most of the weekend.

Visit 3

Then I put his nose in the corner while I fetched my cane. You can imagine what happened next. And a heck of a lot of it all weekend long!

Visit 4

When david got home, I introduced him to lill jo. She had to say a proper hello to david. Afterwards, I would take my new present for a spin up her ass.

Visit 5

When I was out I dressed her up like a little cheerleader and suspended her in her high heels with a ball gag. david was allowed to go visit her and user her holes as he saw fit.

Visit 6

We even had a threeway!

Visit 7

The End

Finally, I once made lill jo stand holding a piece of paper with his nose against the wall for 30 minutes (all on video so I could watch after the fact and make sure he did it properly) dressed up en femme. He was somewhat worried that somebody in the house might barge in on him, and this is how he expressed himself...

Worried 1

I suspect many of you figuratively worry about this with regards to your pervy porn habits! Ha Ha!

All good things must come to an end, so let's end here now with a big heartfelt thank you for my friend lill jo for all these exciting images!

Thank You from us all!

[Please leave comments below. Tell us which images particularly catch your eye and why!]