Friday, 23 February 2018

Jonathan art manips: Stepdads Take Charge

The absolute dream for most older single guys is to hook up with a moneyed divorcee with an 18-year-old son (or sons). As well as getting to tap some no-doubt-neglected housewife ass and spend her alimony, older gents know that white-middle-class boys are just desperate to have their deepest gay fantasies (and they all have DEEP gay fantasies) explored by a bigger, stronger, older man with the authority that only a stepdad can wield!

Having had a man's finger in my ass after a spanking, I can confidently say that, once you've spanked a boy till his bottom glows and his tight little buttole is puckering like crazy and begging to be penetrated, then if you slip a finger in there OF COURSE he's going to disgrace himself and moan like a whore even if his mother and sisters are present! One can imagine that it isn't too hard to work out what those 'strange sounds' might be, and the girls will be teasing their brother relentlessly (checking their watches - oh isn't it is nearly his bedtime Daddy - knowing full well that for their little brother bedtime means buttfucking!)
Being made to perform a 'blumpkin' is one of my dirtiest fantasies, and though I managed to create it earlier for a prison scene I much prefer it in this domestic setting. Just imagine the humiliation of sucking on an older man's cock while his eye-stingingly smelly shit splashes into the toilet bowl!
I took a lot of inspiration from Betty and her friends for the absolute glee that the boys' female relatives take in their abject pain and humiliation. There's something hot about a spoiled sadistic sister, who loves getting her innocent brothers into trouble so she can watch their humiliating punishment while knowing she will never have to suffer anything so bad herself! And in a house where I could be made to strip naked for spankings and hot gay sex acts on the whim of a dominant older make has been a big fantasy of mine every since I read about Teddy and Dickie being made to remove their clothes for endless whippings, wankings and cocksucking 69ings!
Although obviously I am bisexual, I am outwardly straight. While I get off hugely on fantasies of being spanked, made to suck cock or lick ass, and fucked in my tight little butt, in some ways being subjected to more 'romantic' or 'affectionate' aspects of gay sex would be even more humilating (and exhilarating) for a supposedly straight boy. The toesucking stepson in the third pic is inspired by one of my favorite stories - 'Using my straight neighbor' by Sebastian - about an older gent turning his younger neighbor into his gay sex slave. Here are some of the highlights...
It was afternoon and he was in my flat with his shorts pulled halfway down his thighs. He was over my knee and getting spanked. He had the underwear I’d been wearing the previous day stuffed in his mouth and his hands were tied behind his back...

Two hours later I’d made him strip naked for me. After a while I was able to untie him because he was cooperating and knew that verbal protests would have consequences that his red and tender arse could probably no longer take. He was kneeling before me naked and licking my feet, balls, arse and sucking me off, all the while holding eye contact to show his submission, just as I’d taught him to do...

He was mine now. I knew that and so did he. I explained this to him once more and in no uncertain terms as I sat on my sofa and he knelt before me, naked on the floor, sucking on my big toe obediently, holding my gaze and nodding every now and then as I spoke...

I now viewed him as my unconditional property. I’d fucked him in all possible positions and made him look in the mirrored doors of the wardrobe and watch himself getting fucked by me. The rest of the time I made him hold eye contact. Whenever I had him in the missionary position I made him kiss. This overstepped another line for him, and he protested. But he only protested once, and the spanking that this brought him made sure that he not only regretted it but apologised and asked me to continue fucking him...

Obviously all this is hot hot hot, but I find myself especially turned on by having to maintain loving eye contact while sucking an older man's toes (or his cock!), or being kissed passionately by his bristled mouth with my hands bound behind my back and my legs spread, as his full weight pins me to the bed and he fucks me missionary style in my tight little butthole. I soooooo wish I'd spent my youth enslaved in this sort of relationship with an older man, be it a stepdad, neighbor, landlord or friend of my parents.
And speaking of my youth, like all middle-class whiteboys I often wore my mother's clothes and makeup for my pathetic wanking sessions. I even used to insert dildos in my ass, so if only I had been as lucky as the boys in the last pic and had a big strong stepdad who regularly reamed my sissy fuckholes with his real, rock-hard cock!


  1. Brilliant scenes of what boys should expect from their strict step-daddies. Thank you!

    1. You are very welcome! And your use of the word 'expect' has sparked my imagination - I'm picturing a cute 18-year-old collegeboy whose mother has just remarried, reading this post and quaking with fear (and excitement) at the thought of what's going to happen on his first night under his new stepdaddy's roof!

    2. What a lovely thought... and of course being a visitor to your naughty site he deserves everything coming to him!

  2. Hi,

    Even if I don't have deep gay fantasies, I like the idea of a boy spanked by his stepdad till his bottom glows and his tight little butthole is puckering like crazy and begging to be penetrated.

    The temperature finger-taken in front of sadistic mother and sisters, the fact that the boy moans like a whore when the stepdad slips a finger in there can give them some ideas!

    The mother.
    She always insists that maintaining intimate hygiene is important for health and well-being of children.
    When it comes to cleaning the anus, (both the outside and the inside) she tells his son : "you, like many people, just aren't doing it right. Sometimes, if you don't wipe properly, fecal matter can accumulate in the anal area causing irritation and discomfort, and being the cause of odors."

    Talking about feces she does not want to waste her time with digital stimulation and things like that with her son. She is in favor of thorough asshole and rectum cleaning.

    As for me, the mother says, I find that a baby-bottle brush fit more easily into his tight anus and is easier to grip.
    It scrubs the rectum more thoroughly than a hairbrush
    My old baby bottle brush is also the only brush I tried that has a separate mini-brush for cleaning the tip of his cock

    The sister.
    One morning, she was right after her hairbrushing so her hairbrush came in handy. Of course, she used the bristly head of the brush, not the handle.
    The asshole of her brother got insanely swollen and painful as she progressed.
    His asshole got swollen and sensitive for two days but, what is important, it became crisp and clean (and his stepdad kind of enjoyed it)

    His stepdad, as to him, prefers a toilet brush deeply stuck in his little slut's rectum.

    1. Oh FUCK!!! I will never look at my toilet brush in the same way again...

  3. It's up to the little slut to clean it !