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...