uptown-pillow-princess - Tumblr blog

[uptown-pillow-princess]

a comic about cuddles

[uptown-pillow-princess]

Why do you hate straight people

heres my paypal

i’ll answer your question when i recieve payment :) thank you so much!

[uptown-pillow-princess]

So much has been said about femmes being the perfect porn material for their butches, but you know what? A delectable scenario for me is when a butch yearns to be the perfect porn toy for their femme.

My sub top butch, made to please—desperate to please—and pavloved to ache between their legs the second I so much as insinuate any willingness to allow them the privilege of making me feel good.

Throbbing inside their boxers, which are getting messier and messier by the minute, hips mindless pumping into thin air—undoubtedly imagining how slicky and easy it'd be to simply slide all the way inside the hole they're dying to fuck long and deep, being then massaged and sucked in by my inner walls, trapped inside my cunt til their bush is soaking with a mix of both of us and my cervix is kissing the tip of their cock—only to be forced to hump back onto whatever is under their body when the disappointment of not being hugged by my pussy crashes upon them.

Being told to be good. Being told to listen.

Being momentarily shushed if any shyness comes to the surface... reassured and guided by soft touches, a kiss on their forehead, a scratch behind their ear...

Being instructed into which ways to best touch themself, for exactly how long and in which speed, and to not hide any new noises from me if they really do need to shoot their load deep into my womb as much as they keep begging me to...

Being told to spit into their hand, all over their cock, and to fuck up into that unsatisfactory channel til they're allowed to use the lube, and recreate, as close to it as possible, the feeling of fucking into my tight, warm pussy...

Maybe throw in a fleshlight, too, uh? So they can show me exactly how good they can be, prove themself and their skills to me, never missing any of my inquiries, never making me wait for too long...

Like a good boy, no matter how delirious the whole situation and pleasure turns them into, describing to me how every thrust feels like... but more importantly, how they imagine every thrust will feel like once they can have the real thing.

Then I get to describe in vivid detail how watching them putting on a show I run makes me clench and drool uncontrollably over my own inner thighs—spread and flaunted in front of their eyes... one hand disappearing between my legs as I toy with my clit, the other holding the camera now aiming directly at their crotch... a souvenir for later—whilst whispering over the delicious sounds of wetness and friction all the things I'm going to let them do to me...

If they earn it.

[uptown-pillow-princess]

Need to be so cute and tempting that you just have to fill and corrupt me. Sit me on a classic vanity and make me watch you thrust in and out. Make me wear lingerie that does nothing to cover my tits or crotch. Sit me in your lap and finger me until I’m begging to cum. Force me into a mating press whenever I get shy. 🥺🥺🥺

[uptown-pillow-princess]

its kinda fun to let prey pull away a little when you already have it held down and stuffed full of your cock because then you can feel its tight hole gripping your dick as it lifts itself up off which then lets you thrust back in nice and deep and fast when you lunge forward to pin it again

[uptown-pillow-princess]

Fuck casual. devote yourself to me. show me the depth of your clinginess. give your all to me and watch me give it right back to you. you dont have to hide with me, my love.

[uptown-pillow-princess]

UGHHHHH

[uptown-pillow-princess]

It's honestly crazy that discussion around testosterone HRT skews so much towards the beginning stages of it (to the point that you have dozens of guys thinking their transition is "failed" if they don't pass by like a year in lol) and what the initial changes of the first couple of months to years look like, like the classic laundry list of those early basic changes like bottom growth, voice drop, etc, when IMO literally none of that compares remotely to the depth and intensity of the long term total masculinization you start to experience like 3-5+ years in.

[uptown-pillow-princess]

[uptown-pillow-princess]

How to Finish

I drew this poster for Jon Acuff and his FINISH book tour. Big thanks to Jon for this collaboration, his book has some great ideas about how to complete creative and life goals.

[uptown-pillow-princess]

[uptown-pillow-princess]

doing cute domestic stuff for my butch while dressed all pretty with a fabulous robe (see photo for reference), the dream methinks

[uptown-pillow-princess]

Don't think there's anything better than being fed and fucked and not having to worry about a gd thing for a whole day. And a new house warming gift!

[uptown-pillow-princess]

pretty girl, sweet girl, babygirl, good girl, my girl…

[uptown-pillow-princess]

idc (i'll definitely cry)

[uptown-pillow-princess]

i need to flirt or be flirted with everyday or i’ll shrivel up and turn into dust and blow away in the wind

[uptown-pillow-princess]

thinking about the other day when she first pushed inside me and i was having a little bit of pain and needed her to hold still for a second and then go slowly. and she did, she was gentle just like i needed, giving me time to adjust while i closed my eyes and breathed into her neck. but as i started to feel more comfortable and i pulled back to look at her, i realized that her self control was hanging by a thread. she was looking at me like an attack dog looks at an intruder, fighting against its every impulse while waiting for its master to give the kill command. knowing that i hold her leash, while at the same time knowing that that leash is thin and could snap at any moment, made me feel like i’d died and gone to heaven. simultaneously so powerful that i could get a god to treat me with care just by asking nicely and so powerless to stop her if her self control breaks and she decides to rip me apart. i realize that the dog metaphor and the god metaphor are blurring together here but you get the point