O Captain! [thy] Captain!

he/him ★ 20 ★ 18+ sideblog

[fruitfulendeavour]

For you, anything.

★ You can call me Captain (if I can call you mine😉)

⤅ Transman switch leaning dom

⤅ Always open to asks, come yap for my entertainment

⤅ This is a solely 18+ blog

⤅ Want to chat? Send an ask with your discord and I'll message you ❤️

⤅ Likes and dislikes below the cut ↡

✦ Likes

Uniforms/Military/Boots

Discipline and punishment

Sexual inspection/medical play

Roleplay (message me!)

(Especially primal play and military play)

Puppyboys(/girls)/Catboys(/girls)/Etc

Training (+ to some extent, brainwashing)

CNC (Intoxication, somno, etc)

Breeding (as a dominant)

Bondage

Exhibition and free use

Some forms of guro

Praise, degradation, and humiliation

Dehumanisation/Objectification

Bellies, chests, thighs

Probably more that I'm forgetting right now ...

✦ Dislikes

Scat and vomit (neutral towards piss)

Fauxcest

Bestiality

Pedophilia/Loli/Etc

Detrans/Transphobia/Feminisation

Pain (towards myself)

⤅ Header image is "The Kiss in Private" by Hubert Denis Etcheverry

⤅ Profile image is "Arthur Wellesley" by Thomas Lawrence

[gett1ng-kinda-fat]

Just two love birds straining their bedframe💜❤️

[p3bls]

the concept of being "broken in" is so hot like you're gonna fuck me or hurt me so aggressively and with such little concern for my body that you permanently make me more compliant and submissive?

yes fucking please

[dumpster-of-amontillado-deactiv]

wish you were here 😌✨

[faithful-freak]

boy that gets embarrassed that he wants to be a dog… collaring him, making him fetch and do tricks for me despite his hesitation of acceptance and stiff movements, but after some training, and the warm satisfaction he feels from me scritching behind his ears as a reward, he gains the confidence to work harder and harder for the “good boy” i’ll coo at him each time. bonus points and extra lovings if he learns to enjoy the burning embarrassment, and just owns up to being a freak for me.

[fruitfulendeavour]

I can't believe I was writing porn when the Pope died. God have mercy on my soul

[gh0stbelly]

Lil updated header after a 20kg+ gain <3 Do you think I look much bigger? :3

[lardchitect]

The Pilloried Pig

The pillory closes around your head and hands and you immediately feel the fear and thrill of being locked in. "Ah, this looks great on you, piggy." You feel my hand grip a handful of fat hanging from your exposed flank. You try to turn your head to watch what's happening behind you but the holes in the wooden clamp don't allow for much movement, so your only choice is to accept being groped like a piece of meat and as you anxiously wonder what will happen next. I pinch and play with the fat of your exposed rear.

"I'm going to enjoy this," I say as I caress the sagging fat rolls spilling over your back and hanging off your sides. Your body jiggles a lot as I manhandle it and I can tell you're nervous and horny. So good. I walk around to face you, enjoying seeing the nervousness and naked arousal written across your face. It's an exciting situation. Your body is exposed and restrained, totally at my disposal. I'm practically salivating. "I hope you're hungry, pig. I have quite a feast prepared for you." You nod in agreement, grunting lightly-- like a pig. Of course you are, you always are.

I can see that being locked up like an animal is exciting you and you're already starting to pant lightly, your soft, plump body beginning to heat up and quiver in anticipation of the forcefeeding that's soon to begin. Your mouth waters. Your soft flesh quivers with anticipation and desire. You know what's coming next, and you need it desperately.

We don't wait long for you to begin your meal. I bring slices of pie and shove each into your mouth. The apple-cinnamon taste washes slides fills your mouth and soon you feel the weight and pressure of the sticky, sugary treat as it fills you and settles heavily in your belly, adding to the burden of its hanging mass. Its soft flesh stretches as I stuff more and more into you, every bite making you increasingly horny. Next is cheesecake. Bite after bite. Slice after slice. Your pussy more and more excited with every morsel I shove into you. You moan and gasp, as your fat tummy has stretches painfully and wonderfully with more and more and more and MORE fattening dessert is forced into your stomach.

I continue with no regard for how your body feels about the strain, and it's driving you wild. I can hear the little grunts you make every time I force more and more of it down your throat. Your stomach feels so swollen, the skin so tight, but I still force an entire tub of cake frosting in. It's so much, and it's so good. Finally I stop for a moment and a pathetic whimper escapes your lips as the massive amount of food settles heavily in your overburdened belly. The pain in your distended belly is incredible but that does little to slow the ache between your thighs.

I grab your growing lovehandles and jiggle them for a moment, enjoying how the movement of your soft flesh travels from your exposed rear to your flanks. The sound of slapping meat is absurdly erotic as I fondle the rolls and flab on your helpless, bound form, your face turning red and your moaning turning breathless and desperate. Your belly looks so deliciously bloated… My hand comes to a rest, caressing it as my gaze slides along your body.

Your eyes are glazed, unfocused, and your mind unable to focus on anything beyond the desire burning between your legs and the wonderful pain of your aching, engorged belly. I watch, amused at the little squirming motions of your bulk and your labored breaths. After a few moments of allowing you to suffer through the intense sensations washing over your fat, overindulgent form, you groan in anticipation of more to come and begin to hump the air. I slap your fat ass. "Slut! Have some patience!" I scold mockingly as I grab a handful of belly or thigh or back. The pathetic, muffled squeal sends shivers down my spine and hardens my cock. I walk back out of your sight, and when I return I am carrying a large bag full of some heavy liquid with a tube attached, which I stick into your mouth. I watch in satisfaction as you begin slurping on the weight gain fluid, powering through your painfully overstuffed belly. Your cheeks are bright red. The bag empties itself slowly, while you just continue to drink. Your breathing has become so labored. Every exhale sounds like an agonized moan of pleasure. Really, it's driving me wild too. But it's no fun if I show it.

As you are preoccupied with slurping down the thick concoction, I walk out of your field of view and then you feel my hands grip the thick love handles on your flanks. You squirm, your rolls and handles jiggling, as I begin fucking your restrained body. With every thrust I rock you against the stockade and make you slurp down more and more of that thick weight gain formula. I grab the pillory's top board to use it for leverage. Your fat body shakes as I fuck you from behind as you desperately suck down more fluid into your belly. The feeling is exquisite, your overfull gut jiggling, your body clenching and gripping. The pain of being overfull only heightens the experience.

It doesn't take long for you to cum with all the sensation I have been forcing upon you, your moaning muffled by the hose forced between your lips, but your body betrays you as you shake and quake beneath me. Even after, you continue sucking on the hose. Greedy. I love it. Really though, I'm not far behind you in orgasm, especially after you finished. The sensation is heavenly as I fill you, your fat, restrained body shaking. I let you stand there slurping on the gainer shake as I leave to prepare the second course.

[fruitfulendeavour]

A Prisoner

He's stripped -- absolutely and wholly naked -- in his cell. A cloth gag in his mouth, hands bound to a hook above his head, legs spread wide open with a bar between them. Cock soft and on show for any who decide to come see him, yet cast in shadow for the candlelight and his thighs' attempt to hide that soft part of him.

It's humid down here, he's been sweating for hours and hours; hot and humid, and every drop of moisture on his skin sticks to him, makes him brighter when I come to see him. The hair on his forehead is damp, even I can see that in the meagre light. His eyes are bright, cheeks ruddy, and a flush stretches all down his neck to his chest in response to the heat. Even yet he's still lounging like a tiger, like something that could eat me, rather than the other way around. He's panting from the temperature, the lack of water. Loud.

He's lucky that in one hand I hold a candle, the other a cup of water. No whip or flogger yet. But it all depends on how he behaves.

I nod to a nameless, faceless figure; the gaoler unlocks the cell so that I may step in, and then locks it behind me. I walk forth, kneel by the prisoner, place the candle down. Up close his skin glitters with sweat, I can see the track-marks it's left behind.

I pull the gag down, raise the cup to his lips, and he drinks. Trusting that it's not poison, for why would I poison so helpless a prisoner? He drinks voraciously and the water drips down his chin, spills on his chest -- he shivers for a moment, gooseflesh raising about his arms. With my free hand I wipe those sweaty hairs away from his forehead, making a show of checking for fever, leaning in just enough to catch even stronger a smell of his sweat. Musky, rich, tinted with that sweetness of fear from his capture and keeping. The hair under his arms is dark and thick, so thick I can barely see the skin underneath. I hold back the urge to lean in further, and instead take the cup back. He leans forward in chase, but is restrained by the immobility of his shoulders.

"You'll have to earn it if you want more," I say, and he looks at me with gleaming dark eyes, "You do want more, don't you?"

The false concern in my voice must've displeased him, for those pretty eyes narrow. He doesn't speak, so I reaffix the gag and make a show of getting up and leaving. That, he responds to. A thready little whimper, a creak from his vocal chords that I doubt even he knew he could make. I smile and move to stand in front of his outstretched, spread legs.

I once again drop to my knees and crawl forward, cup forgotten beside the candle, and I lift that spreader bar -- and therefore my captive's legs -- above my head, allowing it to drop down on my shoulders and eventually slide down my spine as I progress forth. I'm now solidly between this man's legs, and I allow my mouth to lead me down to his flaccid cock.

It smells too, just as strong as his underarms. The hair here is thick, a solid bush on his pubic bone, and it has thoroughly conquered the insides of his thighs, his soft sack, and what I can see of his arse from this angle. Despite the heavy scent and likelihood he hasn't bathed in at least a day, he's rather clean. His groin smells of sweat (heavy), piss (less so), and the overwhelming reek of testosterone (heavenly).

Licking his cock is gifted with a jump of the thing. Average sized, uncut, the head probably pink, but obscured in shadow. He groans low in his throat, so I lick it again, savour the taste of him. I don't take him into his mouth, but rather press open-mouthed kisses to his cock, sack, and thighs. I breathe through my nose, close my eyes. I know precisely what face he's making, a face many of my conquests make. The noises that build in his throat are familiar yet completely unique. I get faster, mouthier, the louder he becomes, training him to respond to my touch. But as he starts to leak, cock stiff like it wants to pierce me, I pull away. He makes a shallow noise. I make a mocking one back and lean forward to chase his belly hairs all the way up to his navel, pressing a kiss there and wriggling my tongue inside to taste all of the sweat that has gathered in that spot. That gets me a queer noise, a shudder, a gasp, and I innocently blink up to see his face; surprise, wide eyes, a patchy brightness across his cheeks and nose. I pay more attention to the spot and he wriggles as much as he can, clearly unused to the attention.

I move my tongue further up, up to his chest, his nipples, which are already peaked from the attention on his cock. I rub it with my hand, my other hand coming up to steady myself on his shoulder. I feel a pulse of precome leak over my fingers, and I lean into his throat, nipping gently, harder when he responds positively with a whine. He groans when I suck a bruise next to the fruit in his throat, tips his head backwards to permit me more room. I hum and kiss his jaw, but not his mouth. He hasn't earned that just yet. I spread my kisses to his shoulders, his chest, even manage to sneak my nose into his armpits several times, massaging his cock slowly all the while. He's trying to buck into my grasp, now, but I loosen the fist around him whenever he does so. His pleasure comes only as I allow it to. I bite his chest more viciously than his throat, don't want him to panic with my teeth so closely to his pulse. Each bite makes him throb in my hand, so I bite harder and more often, until I'm forced to take my breaths with my nose pressed up against his hairy, sweaty chest. A particular yelp makes me stop, survey the damage I've done around his nipple. It's hard to see in the dark, so I lick it better, and press a reassuring kiss to the side of his jaw.

He blinks down at me, and that becomes blinking up at me as I stand between his legs. I step out from between them as delicately as I can manage, already working at the buttons on my shirt, and then my breeches. I push them down my thighs, allow my captive to stare, step out of them as attractively as one can manage -- which is, honestly, not much. I present myself and ask:

"Am I to your satisfaction, sir?"

I can't keep the cheekiness out of my voice, but all I get in return is a slow nod, which picks up quite swiftly into a faster nod. A desperate nod.

"Well then," I say, "press your thighs as tight together as you can, if you please."

He does please, very much in fact. Despite the bar keeping his ankles apart, he makes a very good show of pressing his thighs together, enough that I can see the muscles shifting and straining even in the dim light. He even shifts his hips as far forward as he can for me, the darling thing. I straddle him, sink down onto his lap. My thighs burn with the distance I have to spread them to sink down onto him, but they've had to stretch further before. I guide his cock into place, press it against my cunt -- I'm already soaked, and he's positively slick with his own precome. He slots in without any real resistance at all, and we shudder as one as our hips meet.

I place my hands onto his shoulders, the sides of my thumbs brushing the proud column of his neck. He looks at me with something unidentifiable in his eyes, and his arms twitch as if his hands want to come down and hold me or strangle me or pin me down against the hard floor and take control. I laugh and roll my hips, can't restrain the noise that leaves me, nor can he control his own voice, which makes a very clear "Oh!" even through the gag.

I move faster, confident enough in my position to let one of my hands come down and touch myself. My movements become jerky when I do so, more focused on my own pleasure than that awarded to the prisoner, but he doesn't seem to mind so much, already panting and gasping like he's trying to stop himself from having a short fuse. I grind down onto his lap, feeling oh so full, and continue that sharp grinding as I near my own peak, thighs burning so much with my riding that it was ultimately distracting me from my pleasure. I start making quiet noises as my hand movements grow faster and he responds positively to that, his own noises rising louder to encourage me on. Or perhaps he was just so caught up in the moment he forgot to check his voice. Either way, I rock my hips viciously, chasing my orgasm, and he groans low and loud, and his cock pulses, once, twice, thrice, and vaguely I wish I had come first, pulled off and brought him to paradise with my hand, but mainly I just rub myself and come as well, situated firmly on his cock.

We're both sweaty, both panting, and I lift my slick hand to his gag, pull it off his mouth to allow him to breathe easier. I kiss him, on the mouth, but he's so slack jawed I doubt he even noticed me do so.

I push my head into his sweaty collarbone, feeling him still solidly inside me, feeling his head dip to press into mine. He hums in contentment, and I hold back the urge to do the same.

I'll get up later. I deserve a quick little rest.

[ddeaddogg]

Frotting has such a hold on me. Like... grinding my tdick on his cock while he tells me mine is so tiny and we're both panting and groaning and desperately pressing closer and he's whispering "Fuck, you're getting so wet. Look at how easy they slide against each other now" and I'm sooo embarrassed by how sensitive I get and how much bigger he is than me while my cunt gets us all messy and eventually he pins me down so he can grind harder

[frigateslutredux]

my xaoptaun censored for meeee

[strayfvggot]

the inherent eroticism of slipping a pristine halter over a stallions nose. tightening the throat strap. tucking his ears under the top band. gently pulling his forelock from underneath it. the satisfying click of the lead rope hooking into it and tugging him along. heavy, satisfying hoofbeats as his muscles ripple, ears flicking, tail swishing, picking his head up when he smells a mare, cock twitching. this big, strong stud completely docile and patient and obedient even though he’s aching to mount, to breed. neck arching, pawing at the concrete, huffing. getting brushed and patted and praised after spilling his load inside half a dozen fillies that day. sigh.

[puzzledpony]

ATTENTION PONIES OF TUMBLR!!!! Tell me what breed you identify most with and/or tell me about your ponyself :))) Hearing about other ponies makes me so happy

I’ll start! I consider my ponyself a fjord horse and am typically pretty mild tempered and willing to please. I like to work hard and consider myself a work horse although sometimes I feel like a fancy show pony or breeding mare! I like to please everyone around me and will push my limits just for a smile from my owner. I like harsh training with praise mixed in there <3

As a trainer, I like the wild ones ;)

[fruitfulendeavour]

hiiiiiii im druuunk

Hello darling~

What are you thinking of doing with your state of intoxication? Getting more drunk? Touching yourself, God forbid?

[frigateslutredux]

maybe booooooth :p

[fruitfulendeavour]

How scandalous! Will there be photos taken, or will it be left to the imagination, you whore?

[fruitfulendeavour]

The Captain is officially back. He has, amongst other things:

Broken his wrist

Applied for his dream job and been rejected

Just not been that horny

But that all changes today. His posting will return.

[fruitfulendeavour]

hiiiiiii im druuunk

Hello darling~

What are you thinking of doing with your state of intoxication? Getting more drunk? Touching yourself, God forbid?

[ftmbigbro]

(contains: light cn*c, dehumanisation)

How To Guide: Get your brand new tboy ready for use!

Please notice: when he arrives at your door he will likely be very shy and may mostly be looking down at his feet. This is completely normal and actually indicates that your boy will be obedient and easy to use.

Although there are many ways to break in a new tboy, we generally recommend the following method:

Bend your tboy over a piece of furniture. Dining table or most desks will do just fine.

Make sure he is positioned correctly. He should he laying flat on his tummy, legs spread nice and wide and with his hands on his back. (Hands can be either bound or cuffed for maximal restriction). If you've got a smaller model, his feet might dangle above the ground. That should not be an issue.

Pull down his trousers and underwear. You can either take it completely off or just let it hang by his feet while he is in use. If he protests or squirms, give him a hard smack on the ass. (If wiggling or protesting continues, see the section two of the manual: How to: Fix a bratty tboy)

Now you should be able to get a good view of his cunt and hole. Most likely it will already be dripping wet, however if it is not, massage or tease it gently for a couple minutes.

When you first push into his hole, it might be quite tight. Apply as much force as needed to penetrate him. Moaning, whimpering, sniffling, crying and light screaming from the boy might occur at first use. Stuff his mouth if this continues or see section two of the manual.

Congratulations, now your tboy is devirginised and ready for use!