Friday, 12 June 2020

Biting the Pillow in Prison (new Ian Hamilton art)

Ian Hamilton has long been one of my favourite artists, and is still going strong creating brand new work on a regular basis. Like most artists, he is game for commissions, but I never realised that he was enthusiastic about creating gay and cuckolding artwork until this year... at which point of course I couldn't resist asking him to illustrate some of my dirtiest fantasies!
And it will come as no surprise to regular readers of my blog that the first thing I asked him to draw was a prison sex scene...

'You'll be biting the pillow in prison' is a phrase I've heard many times over the years, used as shorthand to suggest to a white-collar criminal what he'll be doing while his big burly cellmate buggers him senseless. Like the many other suggestions of what would happen to a nice middle-class boy like me in prison, the phrase always sent a shiver down my spine. But I don't think I've ever see an actual depiction of prison pillow-biting, so I thought it was high time Ian Hamilton added to the small but perfectly formed pantheon of gay prison sex art and showed a pillow-biter 'in the flesh'!

Needless to say I am very happy with the finished piece. It captures so much of what I fantasised about happening to myself in my early twenties... the helpless vulnerability of the submissive guys in the dank surroundings of the cramped cell, particularly the pillow-biter himself... I love the detail of him not only biting the pillow but also pulling the mattress off the bunk, such is the intensity of his fucking! His expression is perfect... so desperate and woeful, but also with a hint of acceptance, as if he's needed a big thick cock in his ass all along and his Prison Daddy is satisfying a deep, long-held desire... only confirmed of course by the way his semi-hard dicklet is rubbing against that conveniently placed bolster!

A word too for the way Ian draws his belts... they look so gorgeously thick and leathery, real Daddy's belts for some real Prison Daddies! The scorching welts on the boys' buttocks suggest how they were used to encourage them to suck cock and take dick, and no doubt also make things a little easier - the penetration of that huge dick is probably a bit less painful among the inferno of the bitchboy's backside! Though if the Prison Daddies managed to stash some belts somewhere, they no doubt managed to hide a bottle of lube in the cell too...

In the second pairing, Ian has captured another of my favourite submissive gay fantasies... to be made to suck a sweaty cock until it is as clean as a whistle! No doubt the other young cellmate is hoping that if he sucks cock well enough then he will be spared an assfucking... but I bet he won't!

The dominant convicts certainly look older and more experienced. No doubt they have a few years on the clock, and it is a real treat for them to have landed such young and nubile cellmates.
Perhaps the unfortunate young prisoners have just arrived, and are being given an immediate introduction to life in prison (notice the guards haven't even got round to making them remove their watches yet... or maybe they and the older cons share my fetish for seeing skinny betas spanked and fucked while wearing dainty, unmanly wristwatches...)

Perhaps there is even an element of  'protection' going on, with the old lags agreeing to take their naive young cellmates under their wing, like in one of my favourite descriptions from a long-defunct gay prison porn site:

They were both new, and the older inmates couldn’t wait to get hold of their precious assholes. Matt and Tom knew they’d have to team up with someone and pay for protection in their own way. Their cellmates gladly agreed to protect them, and very soon their huge balls were slapping up against the guys’ firm asses. Ouch!

Or maybe all the men in the picture are weeks, months or even years into their various sentences, and this is just how the weaker inmates have to spend their evenings! Perhaps they aren't even cellmates, and have been sold to the old lags for a pack of smokes, or given as a reward for some gangland atrocity?

Do the unfortunate young guys even deserve to be in prison? Are they a couple of small-time drugs dealers who attempted to top up their college funds and are now doing hard time?
Or a couple of backpackers who were supposed to be heading off to college, but they got forced to carry a package of drugs into the USA from a less enlightened country (or even had it slipped into their luggage without them noticing) so now they're heading off for a sizable stint in the big house!
Or perhaps they're completely innocent, framed by a corrupt cop or a merciless mafia don?
As usual, my fantasies tend towards them being a couple of unfortunate innocents who through no fault of their own will spend the best years of their lives getting their tight little butts ridden and roasted!

As you can see, Ian Hamilton is capable of illustrating a wide variety of erotic fantasies, so if you are interested in seeing your filthiest dreams come to life I strongly recommend commissioning him via


  1. Great post. It certainly revived similar fantasies i've had.


    sissy terrie

    1. You're welcome! I wonder just how many sissies and betaboys have these prison fantasies...

  2. It's usually DUI or finding a small amount of marijuana. It tends to happen on Friday and Saturday nights, so we end up guests of the county or city for a couple of long days and nights. I usually don't get to bite on a pillow, my new "friends" like to hear me begging and crying, others hear it, making me very popular. And yes you are right, as hard as i try to give good bj's it doesn't take their attention off of my well striped bottom. The last time it was a good month before i was ready to have a few beers, drive a little fast on a Friday night with marijuana in the car. It is very nice of Ian to and yourself to chronicle these experiences, they are a good reminder. And the belts do look about right. I thought they took belts away from you, but they even sell them to the inmates at our local facility, along with other necessities. The processing guard just took the amount out of what i had in my wallet, and handed me the belt. They had plenty of belts, but told me they were out of the pink jumpsuits. It was embarrassing being walked to my cell nude, with my tiny erection, with only a belt that would soon be put to good use.

    1. I'm glad to see belts play such an integral part of the prison experience, and I think I would very much enjoy joining you for a weekend as 'guests of the county'! Perhaps we are the two boys in the pic... I guess if you don't bite the pillow then that makes you the one sucking dick ;)

  3. Yes it is, not pleasant, but my cellmate did an excellent job of motivating me. The poor guards only make minimum wage, they found providing belts helped them to augment their income. We don't mind paying for the privilege of being able to spend at least some time in a private cell.

  4. Sorry, Qbuzz, I've been away trying my best to ay getting moved and I'm finally in. This post along with gerl's comments are just so, so hot. I can't imagine the humiliation of everyone seeing me naked, my little willy trying its best to go back where it came from, my little white boney bottom just begging for some color!

    Oh gawd! Wonder how much some cold cream would cost from the commissary to help my poor bottom after my spankings? And from my own belt? How humiliating! I wonder if the guards take pictures, ones that one would pay for to prevent them reaching family back home, perhaps a wife?

    Imagine you come home to find a 3foot by 5ft poster of you getting a bare-ass spanking across the knee of a con while sucking off another. A picture you paid 20 dollars to have destroyed in prison, only to find your wife paid thirty to the same guards to have it not sent to other family!

    Worse, your often put-upon wife now owns that same belt and plans to use it!

    Oh, what wonderful thoughts as you bite the pillow to have the kids not hear their father's ass-whipping!

    Thanks to you and gerl for your wonderful posts!

    1. No problem Father, glad you have you back. Hope the move went well.
      Yes the threat of sissies (prison otherwise) being exposed to their friends and families is a common threat, and it's rather arousing to imagine what would happen if the threat was following through... especially if it involves the same belts we were whipped with in prison, I love that idea!