Ass Licking and Dick Whipping (Jonathan art manips)

Creating manips of Jonathan's artwork has really allowed me to explore my dirtiest kinks and fantasies, which in many cases have been buried deep for many, many years. As a shy teen leafing through illicitly obtained porn mags, I invariably enjoyed the fetish themed ads at the back the most, as they were always choc full of spanking and other kinky content that blew my inexperienced mind.

In one advert for dominatrix services there was a line that went something like this...

Clad in lipstick and fishnet stockings to be toyed with (and more) by two leather-clad gays...

I long had an ambivalent view of sissification, and while I enjoy the full on feminization seen in the works of Safeword Ignored or Lustomic artists, when I'm imagining myself being feminized, used and abused I've realized that I prefer a more subtle form of sissification that almost exactly matches the tagline from all those years ago. 

Maybe a spritz of ladies’ perfume, fishnet stockings, high heels, women’s jewellery like a dainty wristwatch and a string of pearls…

Like a school uniform or sock garters, this sissy outfit is just a way of accentuating my status as the beta bitch-boy who was born to be abused. I love the idea of my perfume wafting across a big strong stud’s nostrils as he shoot his load in my well-spanked sissy ass!

Other taglines I remember from femdom-based adverts read simply:

Spanked till you spunk!

50 lashes of the penis whip!

I'm not a fan of cock and ball torture (though I appreciate it more since I read KD Pierre's explanation that it's more about the anticipation than the impact, and it's so ubiquitous in femdom art by the likes of Sorenutz that it's hard not to develop an interest in it...). But in both real life and in my fantasies, I love having the shaft and tip of my cock whipped with a thin leather implement like the tip of a belt or a slender strap. And like any good subby, I have always fantasized about dominant ladies sitting on my face...

But more recently, I have become aware of the idea of gay facesitting… In other words, me being forced to like back and take it as a big dominant stud sits astride my face, crushing me beneath his sweaty cheeks, my nose pressed deep in his ripe crack, my eyes burning with the manly stench as I gasp for air and my tongue works furiously pleasuring his pungent asshole…

So some of my dirtiest fantasies involve feminization, dick whipping and gay ass-licking. And by creating manips, I can explore all three at the same time!

These three acts sure seem to complement each other, and it's easy to see why us sissy-slut sex slaves would be subjected to having our dicks whipped while our faces are smothered beneath our masters' asses...the CRACK! of stinging leather lash on our stiff little peckers would instantly overcome any aversions we might have to licking our Dominant Daddies' holes like our favourite lollies!

After all, if you spank a guy when he’s sucking your cock then there's always a risk that there might be teeth involved… but if you whip his dick while he's licking your ass, it's only going to make him more more enthusiastic!

Though no matter how well he licks, you won't stop whipping his dick...even without the sadistic power trip, the extra writhing and moaning it produces just feels too good between your cheeks as his tongue remains buried deep in your dirtiest hole!

We even have a dedicated ‘penis whip’ in our house, which is the thin extension strap from a leather strapon harness. It is certainly effective when used on my slender shaft, and it even has buckles so it looks just like a minature version of a Strict Daddy’s Thick Leather Belt (except it’s used on naughty boys’ boners instead of their bottoms!)

But I love to imagine what a dedicated penis whip would be like, as described in the advert...

In my manips, I can depict a bespoke whip designed specifically for punishing the penis… Stockings and heels optional but very much recommended!

And of course gay facesitting and dick-whipping go together perfectly in my dirty little mind...

And lets not even get onto the intense, guilty arousal I feel at the idea of Fartsitting… where a guy breaks wind while my sissy face is buried deep in his crack!

I explored some of my submissive sissy fantasies while corresponding with blog reader Lokijanus, who indulged my fantasy of being forced to be a sissy sex slave to a sadistic older man, and sent a detailed story outlining what he would do to me, which I added as captions to a few relevant manips:

I love these fantasies so much that I incorporated them into the third story from my ebook Lovers Punish Cuckolds 3: In Front of Their Wives, in which a dominant stud details with relish how he turns submissive straight guys into his sissy-slut slaves:

Whether I cum or not, I always make a straight guy suck my cock after I’ve fucked him because I love the look on his face when he tastes his own ass! Sometimes I cum in his mouth but usually I indulge in my dirty love of sitting on his face and making him lick my sweaty asshole. While he does this I whip the tip and shaft of his dick with the tip of my belt or the strap and the moaning and writhing this produces is just amazing. With neither of us in danger of cumming, this can go on for hours, and often does!

After this I usually finish off in his ass or mouth and if he's made it this far I will usually tug him off while I fuck him, though his dick is always so sore and sensitive by this point that I'm not sure how much pleasure it gives him!

I've always loved turning out straight guys and I know plenty of my gay buddies feel the same. It's such a power trip, having a straight boy’s lips around your dick or seeing the look on his face as you penetrate his ass for the first time. I think the thrill comes from the knowledge that, no matter how straight they claim they are, once they’ve had a dick in their mouth or in their ass they can never really claim to be straight again. And once they’ve been defiled, you're much more likely to be able to do it again!

You tend to really push the limits with straight guys, maybe even more than you would with subby gays. And it's amazing how compliant they can be after a sound spanking! Even a long forceful kiss is humiliating for them, so when you start making them lick your sweaty armpits and asscrack, or kiss your feet and suck your toes, always while maintaining eye contact – there’s no thrill like it!

Most tops have straight female friends, and after a few Chardonnays you’d be amazed how many ladies can be convinced that they want to watch their husband or boyfriend kiss another guy, or get spanked, or suck a dick, or all three... If you've got your eyes on a straight guy, sometimes the easiest way to his ass is through his wife or girlfriend!

My friends who fuck both men and women tell me that girls love to watch guys getting fucked by other guys, especially when it’s their own boyfriends or husbands on the receiving end, and my sissy-slut’s partner was no exception! She seemed to get off on all of it: whether it was her man screaming like a girl as I turned his ass black and blue with my belt, or having to work his tongue between my sweaty ass cheeks, or sucking on my dick just before I stuck it in his tight ass and made him moan like a whore.

I started bringing random guys back from the bar to keep her busy– and it turned out that my slave’s woman was as much of a slut for rough treatment as he was! The sounds of her screams in the next room rang in our ears while I had my fun with her boyfriend, not quite sure if they were screams of pain, or orgasm, or both – either way, I didn’t care, and my sissy-slave couldn’t do anything about it!

Sometimes I did fuck my slave in the same room so that as my cock slid in and out of his sore mouth or bruised, purple ass he could watch, listen and smell his woman getting pounded in all her holes by big brutish men and their dirty dicks. I loved making him suffer, and the look of misery on his face was just exquisite as I filled his aching hole with my cum at the same time as his fat girlfriend took another couple of stinking loads in her ass and on her face.

Though my sissy-slut looked so feminine and enticing in his fishnets and heels that a lot of the time the other guys decided they wanted to join me and fuck him instead of his wife! Things always got real rough when that happened – you know what alphas are like when they’re ganging up on a weaker guy! My sissy sub-slut would be on his back or on all fours with a thick cock permanently pounding his sore, purple tush, while his mouth was constantly filled with cock or his tongue was stuck deep in a big sweaty ass… all while his girlfriend enjoyed the show! Although I often brought more than one guy back from the bar, so she usually still got fucked as well!

To be honest, the thought of gay facesitting takes me to some really dark and kinky places. I fantasize about my big strong stepdad who sits on my face as a punishment… and if I’ve been really bad then it’s done naked!

And if you have access to more than one sissy salad-tosster then you might even be able to whip ass and dick at the same time…

Just imagine the glorious gay gangbang you could have if all the studs in the neighborhood brought their slaves along dressed in nothing but fishnets, heels and women’s jewellery; with the tops wearing nothing but their watches and their erections… Masters could bring their sissy slave-sluts; strict stepdads could bring their sissy slave stepsons; dominant bosses could bring their feminized interns; hardened ex-convicts could bring their halfway-house bitches…

Every slave-slut hole and tongue would be put to work servicing sweaty alpha cocks and ass, with the sissies getting whipped hard front and back to keep them eager!

Presumably if you had enough attendees, you could form a big-enough circle to ensure that every stud there gets to cum with a sissy-slut’s tongue in his ass; and his dick in a sissy-slut’s butt!

Going back to the original fantasy that warped my sweet little mind, Jonathan did draw a leather clad gay who looks very much like what I imagine in my fantasies.

But given what he's doing, it seems my teenage self might have gotten a little more than he bargained for...

The Lusty Widow (new Ian Hamilton art)

I have to say I find widows (or rather, women in funeral attire) extremely attractive. Ladies always look good in black, and the traditional widow outfit includes all sort of other very enticing accessories: demi-veils, stockings, gleaming black high heels, her finest jewellery…

There’s a lot to like! And I realised that it would be an excellent basis for another Ian Hamilton commission…

It’s just a shame for us guys that, when our women are looking their finest, we aren’t there to enjoy the experience in the flesh. I’m not sure if ghosts can masturbate, but if they can then I’m sure many an apparition attending his own funeral has wanked himself silly at the sight of his loved one dressed to the nines!

Although for this ghost, he has returned to find his weeping widow taking some ‘comfort’ from the burly undertakers. It must be an extremely shocking scene to return to… but of course he’s still wanking over it!

As usual, I am extremely happy with Ian’s work. The lady truly is gorgeous… I’m not sure if this was a regular occurrence during her marriage, or if she is just satisfying a few urges now her husband is gone, but she certainly looks to be the kind of woman you wouldn’t mind sharing with a few others if it meant you got to be married to her! And those big veiny cocks are both a wife’s dream and a cuckold’s nightmare!

Ian didn’t make the husband too ghostly, so if you prefer I think this could definitely be a conventional cuckolding scene, albeit before or after a funeral. But what would the story be? Perhaps the husband has a rich relative who has popped his clogs, and the wife feels like celebrating their windfall… and those well-endowed undertakers seem much more suitable than her husband for such a special occasion! Or given that they are all buck naked, perhaps they don’t need to be undertakers at all. They could be her husbands’ friends, although given their age perhaps they are dominant relatives of her husband who are keen to show the young couple who runs the family!

There isn’t a huge amount of widow-based porn, but much of the artwork I do have on the subject was included in my post about my book Headmaster for Housewives 6: The Headmaster Makes Housecalls, in which the Headmaster brings some comfort (and, given her taste for corporal punishment, also some considerable discomfort) to his friend’s lusty widow.

And if that isn't enough for you (and if you are attracted to the widow-look as much as I am, it probably isn't...), here's some more... these widowed ladies really know how to enjoy themselves!

Wedding Day Cuckolding (new Ian Hamilton art)

Wedding Day spankings, fuckings and cuckoldings are always fun, and there is a decent amount of excellent erotica devoted to the subject. However, I was always surprised that Ian Hamilton appeared to have never featured a bride in his work, so I decided to commission him to create a wedding day spanking and cuckolding scene...

Clearly the bride is gorgeous, with her well-whipped juicy ass contrasting beautifully with her white wedding attire. But I also wanted Ian to feature my fetish for bridegrooms' clothing, which I always find hot on submissive men. This groom's hat in particular makes him look like the kind of dork whose new wife gets whipped and fucked by other men on her wedding day – I guess that's why real-life grooms always seem to be holding their hats in photos instead of wearing them! I asked Ian to include the hat, though in his original sketch he had the groom without it for a normal look, and I'm still not sure which style of groom I like most...

Usually when I commission a work from Ian, I have an idea of the story behind it, but in this case I really can't settle on a scenario...
Are the newlywed couple serial spanking swingers who are just starting their marriage as they mean to go on, or are one or both of them slightly less than enthusiastic, and need some encouragement with that big leather belt? The bride's hand on the groom's shoulder suggests a certain level of romance even among the furious, filthy whipping and fucking and sucking... perhaps she is thrilled that as a wedding gift he is finally sucking another man's cock in front of her just like she always wanted (even if it took a long hard belt-whipping for him to agree to do it!)
And who are the two dominant males who are having their way with the happy couple? They certainly look a lot bigger and older than the groom (not to mention the difference in cock size!) Are they the bride's former lovers, mature and dominant just like a young lady needs, here to make sure her wedding night goes with a bang!
Or perhaps they are stepfathers or stepbrothers? Or friends of the family? Or bosses of either the bride or groom (or both)? Or even the groom's friends or old school bullies, who somehow ended up on the invite list!
Wedding day cuckolding is such a popular fantasy, but I wonder how much us potential cuckold grooms would really enjoy our not-so-special day... Would you rather be made to participate like the new husband in Ian Hamilton's piece, or just be forced to watch like the (un)fortunate groom in this excellent work:

Maybe they'll make you film it for future enjoyment...

Perhaps you will be used as a piece of furniture by your new bride and her bulls, so that you can be as close to the action as possible without taking any pleasure from the experience...

Maybe your guests will join in, deriving the pleasure you are denied, except perhaps a quick handjob while you are tied up... though I'd say this bride is quite likely to get distracted and ruin her new husband's orgasm ;)

Even the clergymen might get involved!

Or perhaps you are one of those understanding cuckold grooms who treats your bride to a surprise black gangbang on her wedding night... (Art by Carjim)

After all, you wouldn't want to piss her off, and for her to let her bull loose on you... would you?

Art by Rumata Estorian

Romantic Tales of Domestic Discipline (erotic ebook)

Sometimes a woman needs the man she loves to treat her rough...

Three modern married ladies experience the agony and ecstasy of traditional corporal punishment... and it only leaves them wanting more!

Buy it now, exclusively on Amazon Kindle:

amazon.co.uk/dp/B0944339ND

Or read it for free with Kindle Unlimited:

amazon.com/dp/B0944339ND

In the first story, a high-flying executive spends her Sundays as her husband's sex slave, forbidden even to climax without her master's permission...

And it isn't just spanking and cocksucking that she is subjected to...

First her husband makes her keep a pair of silver jiggle balls inside her pussy for the ENTIRE day, driving her crazy. Then he makes her wear a leather bondage choker that is just discreet enough to pass as a fashion statement, but that doesn't stop her blushing badly... especially when her snooty, overbearing mother comes for tea!

With those balls inside her, it isn't long before the proud young businesswoman is climbing the walls with frustration... and when her husband catches her trying to bring herself some unauthorised relief, he thrashes her soundly and then forces her to join him on a long bike ride with her jiggle balls still in place... the poor wife can't decide what's worse: the spanking or the cycling!

Once her ordeal is over, and she's done all her housewifely duties (and her husband has finished watching his football game of course), then if she's a very good girl then perhaps she will be finally permitted an orgasm on the end of her master's thrusting dick...

She will certainly be sitting on a very sore bottom on her smart executive office chair on Monday morning!

This story was partly inspired by a comment I read online a long time again, referring to an overheard hint of spanking outside a church on a Sunday...

Exasperated by the smug suspected corruption in some posh Church of England circles, I recall one Sunday about 15 years ago walking along a Church driveway on the way to a posh service at The Brompton Oratory.On the way I passed 2 attractive Kensington women about mid 30s dressed-well like slightly suggestive tarts-in flowery floaty dresses white sexy stockings high heels hats etc but quite posh.
I distinctly hear them say in audible voices to a man who greeted them words to the effect: "We’re sorry were late it's SMACKED BOTTOMS for us as we didnt get out of bed in time"!!!!
Hurummph I thought this jest was very inappropriate for a Church surrounds....

I understand that the 'Hand of God' has connected with many a pert and well powdered bottom on a Sunday morning!!

If you knew Christians like I know Christians, this wouldn't be at all surprising. What goes on within a marriage can be quite wild.

Needless to say, I found the image of all those prim, powdered church ladies getting their pert bottoms soundly spanked to be rather inspirational. And as the husband and wife in the story are a respectable, churchgoing middle-class couple, a similar scene is very much included...

In the next story, a mature married couple on a walking holiday stumble across a young pair of lovebirds engaging in some rather kinky antics on top of a lonely hill – with the girl having been stripped naked apart from her watch and walking boots, and bent over a suitably mossy rock while her boyfriend whips her soundly with a switch cut from a birch tree. It isn't long before the boyfriend is giving her a taste of his other kind of rod, both of them blissfully unaware that they are being watched...

Of course the salacious show soon has the older couple racing back to their cottage to engage in their own afternoon delights of spanking and shafting!

In the final story, a headmaster in the 'good old days' entertains his wife with lurid tails of the bottom-warmings he’s doled out, and at her urging brings his strap and cane home...

It must have been rather a thrill to be married to a teacher in the olden days, especially if you had an interest in spanking and discipline, and your spouse was willing to regale you with authentic stories of the canings and strappings and slipperings that went on.

This story is inspired by a dimly remembered tale that I think I read on the the British Spanking Mags blog, but can't find now. It featured a headmaster visiting the cinema with his wife, where one of his pupils obliviously misbehaves quite badly in front of him. He reveals himself to the horrified girl, and informs her in front of everyone that she will pay dearly for her behaviour at school the next day...

This gets his wife rather excited, and I vividly remember the description of him entering their bedroom later that evening to be greeted by her big, naked, juicy bottom, as she kneels on the bed and invites her husband to give her a taste of what he will be giving the recalcitrant schoolgirl the following day!