#trans robby

[laceoddity]

Thinking about Dennis being afraid of Jack getting turned off from seeing his bottom growth, only for the older man to pull out his own, significantly bigger t-dick.

He steps closer to inspect the boys cock before aligning their bodies so their crotches rub against each other.

The sight of their cocks squished together makes Dennis let out a loud keen.

It's obscene how Jack's dwarfs his, and all his insecure thoughts are replace by a need to suck the man off. He tries to say as such, but in his excitement only a string of gurgles and groans comes out.

Jack scoffs at how needy the boy is " Well, Whitaker, you have a lot of growing to do. It's a pretty little thing-" he puncuates it with a sharp thrust before continuing, "just like its owner. But maybe once you're older you'll have a nice manly cock just like me-"

He grinds down harder, emphasizing just how miniscule the boy's dick looks in comparision to his own.

Dennis is mesmerized by it, letting out a stream of incomprehensible noises through his open mouth.

Jack grins, amused by how quickly the resident fell apart. "Shit, puppy. If you think my cock is big, you should see Robby's"

The way Dennis' dick twitches lets him know just how much the boy likes that idea.

"You did what?!"

"You better be grateful Brother, I'm bringing your favourite boy straight to your bed. Or couch, seems like he might be too desperate to wait that long."

[darlinghearted]

Old trans bear Robby who doesn’t think he’s desirable anymore and cis Dennis who literally cannot get enough of him.

“Fuck, Daddy, y’re so good, taste so good.” Dennis babbles, face buried in Robby’s cunt. He’s near tears, all his dreams in life coming true at once.

Robby hasn’t experienced this type of pleasure in years. Dennis’s mouth forms a beautiful suction around his tdick, hot and wet and utterly addicting. He buries his hands in Dennis’s curls, keeping him right where he wants him.

“Good boy, good fucking boy. You’re such an eager puppy, huh?” Dennis moans and bucks his hips into the mattress, and if he had a tail it would be wagging nonstop. Robby just chuckles at him. “My puppy.”

Dennis doesn’t stop eating him out, he couldn’t if he tried. He loves making Robby feel good, more than he likes feeling good himself. He could stare at Robby forever and never once get tired. The amount of times he’d jerked off to pictures of his Daddy was innumerable, Dennis couldn’t picture a hotter man. A good amount of meat on his bones, a big, soft, hairy belly. Pecs that were large and soft even after surgery. A thick beard and wrinkles that showed a full life.

“You’e humping the bed like a dog, huh?” Robby said gruffly. Dennis whined.

“‘M Daddy’s puppy. Daddy’s so hot, I want, I want it.” Dennis’s head feels fuzzy and full of cotton, his only goal in life being to find out how to live off of Robby’s cunt alone.

It was a strange learning curve for the older man, since he had grown so used to being passed over by young pretty boys like Dennis. Many a time he had bought a boy a drink only to have their faces scrunch up upon learning that not only is he trans, but he never got a phalloplasty. He had expected the same from Dennis, maybe even the “I’m not into women.” talk he had heard before. It didn’t make him dysphoric anymore, thankfully, but it did send a spark of anger through him. What he did not expect was for Dennis to cum in his pants as soon as he saw Robby’s naked body.

[unfetteredautism]

feeling bold time to post some bullshit i already mentioned in my discord server

needy sub (cis) dennis who's inexperienced and shy and soft dom trans daddy robby who teaches dennis how to fuck him but dennis is just sooooooo sensitive he keeps cumming so fast :( and he's so sad and upset about it because he wants to make daddy cum :( he wants to be a good boy and last long enough for daddy :( but he just can't it just feels too good he can't help it :(

and robby coos and tells him it's okay while he's sniffling and crying in his arms apologizing for finishing too quick again like "don't be sad baby, you're getting better. you held on longer than last time didn't you? you'll be fucking daddy real good in no time sweetheart."

but yeah dennis is sooooooooo fucking easy

like when he eats robby out his boxers (or panties hehehe) are wrecked in like 90 seconds cuz he's so turned on he's just leaking cum the whole time he's sucking and licking at daddy's cunt <3

and he's not strictly a top so when robby pulls out the strap dennis is going ham on that thing

he'll suck it and whimper on it or ride it like he's trying to obliterate his own pelvis and robby praises him for taking it so well and he knows dennis doesn't need or want a break between orgasms so he just keeps pounding until he tires himself out and that's when dennis starts begging for more and robby has to use his firm voice to tell his baby they both need to let their bodies rest

and dennis begging to fuck daddy's pussy all the time always promising he can hold out for more than a few minutes this time and they both know damn well that's not true but robby doesn't mind cuz he loves feeling his baby boy's pretty little cock thrusting deep inside him, the warm gush when dennis inevitably lets loose early, and the sticky fluid leaking out of him that dennis will lap up like candy after he finishes crying

and the aftercare is robby's favorite part when he gets to take care of his baby boy and kiss him and tell him how good he did and they snuggle up

it's during one of these aftercare cuddle sessions that they first tell each other i love you

[emrysmerlinambrose]

Give me old trans man Robby. Robby who transitioned in the 90s.

Robby who started going by Robby cause 1) it was masculine 2) it eased the name change and 3) he was already pressured to shorten Robinavitch might as well make it useful.

Robby who had shit transition healthcare (as was very common at the time) and is only alive cause he was in med school. Who, like a lot of people, ended up on unsafe forms of hormones cause they didn't know the safety at the time (like pills). Who nearly was chronically overdosed on T cause there were next to no docs who knew how to competently treat a trans patient. Robby who had to do so much endocrinology research to help himself and later the other trans people around him.

Robby who's push to being an ER doc was cause he had to help his trans community since no one wanted to treat them. Who saw how much he could help when he was on his ER rotation. Who saw how his friends were treated and decided to have all of them come to him instead no matter how busy he was.

Robby who had to work through the height of the AIDS crisis and watch as his community was failed by everyone around him. Robby who saw how the other doctors and nurses talked about and treated trans and especially trans HIV patients but had no standing to combat it at the time. Robby who ended up being requested by queer and HIV patients cause even if they didn't know he was queer they did know he was safe.

Robby who has been out so long he still idenfies as transexual. Robby with phaloplasty. Robby who got top surgery prior to chest masculinization really being an option. Robby with fucked up ribs cause chest binders didn't exist yet so your option was only unsafe binding.

Robby who is stealth at work cause he's so used to having to hide that part of himself for saftey. Robby who still has to hide that part of himself for saftey even now and hates that the world hasn't changed since the 90s.

Robby who sees Whitaker just starting his transition and makes sure he never has to deal with any of the bullshit he did. Robby also being with Trinity in lowkey (lovingly) flaming him for choosing to be named Dennis.

Just elder trans Robby.

[deadintro]

I love t4t hucklerobby because all I can imagine is younger trans man Dennis seeing Robby for the first time and all he can think is "we can get that old?"

[actually-andrew-cody]

Something something trans Robby who was identifying as a butch lesbian for a long time during the late eighties early nineties and then as transsexual vecause that was the more popular term. Robby who started going by Robby because people got weird when he was openly a Jewish man with a Jewish last name. Robby who got top surgery in the early 2000s and doesn’t have nipples. Robby who didn’t date men for a long time becsuse he was afraid of being invalidated as a trans man. Robby who had to use unsafe means of getting testosterone until he was in his late 30s. Robby who resisted a relationship with Jack for a really long time becsuse he was jealous but also aware that Jack was like the pinnacle of masculinity in his mind. And then he fucked Jack within an inch of his life and got fucked the same night. Robby who didn’t change his name legally until 2017 and his sex marker.

I love old trans men.

[lassie-farce]

robby taking off his pullover and everyone freaking out that something is happening because he only does that when all hell comes loose

meanwhile robby getting hot flashes because menopause and he knows he’s getting older but why’s everyone being so weird about it

[gremlinkat1992]

Hucklerobby:

Dennis wants his boss, Robby wants Dennis. A Dennis that hunts that old man, everyone thinks they need to be worried about him like he's some simpering child but Dennis who is rocking Robby's world. A Robby who warns him that because he's been on T so long he probably can't come or needs help. A Dennis who realizes Robby has been talked down to and not taken care. A Dennis who fucking becomes feral and makes it his mission to not only eat Robby out but make him come until he's a blubbering mess.

Robby who didn't know that was possible. Robby who is a squirming mess, he's wet, his thighs have bites all over them and he's come four times already. Robby who's sobbing before Dennis even managed to fuck him. Dennis who manages to grin like a cat that won a prize after having eaten Robby out for hours before fucking him. A feral and confident Dennis that decides Robby is now his because no one else obviously knows how to take care of him so he will. And if sometime later Robby ends up pregnant when he didn't think that was possible...oh well.