You stare at Henry. There were dozens of different condoms in that box, and it could take weeks to figure out which one would be the right one. But three.. you could work through those in a day and be back to your normal self in no time. But sex with your younger brother? True, you'd be Jay, but still it felt off. After a moment, you nod. "Fine. Lead the way."
Henry grins like he just won a prize and leads you to his car. With a bit of trouble you get your bike into his back seat then climb in the passenger side. The trip back to his apartment is in silence, and by the time you finally walk up the stairs and into the place you're almost ready to burst.
You've never been in your brother's apartment before, but you only glance around for a moment before holding out your hand. "I need the warming sensations one." Henry opens the box and rifles through it until he finally finds the one you want and drops it into your waiting hand. "Bathroom?" He points it out and you walk in and close the door.
You strip naked, folding your clothes up and setting them aside on the counter next to the sink. The condom is just how you remember it last time as you unwrap it an roll it over your cock, way too loose. But as you start to stroke you already feel the familiar sensation of warmth flooding through you as the condom becomes tight around your suddenly enlarged member.
Jay and Scott are so different, that the changes feel like they happen within a few strokes. You have to adjust your stance as you suddenly shoot up over a foot in height, grabbing the sink for support as your entire center of gravity changes. Swelling leg muscles push your stance further apart, and you have to adjust your grip on your cock as your arms thicken and swell. You almost feel like a balloon as you watch your pectorals pop outwards in a matter of seconds, hair growing up your abs and across your chest in a blink of an eye. Your skin tans and your hair darkens. As you watch your face in the mirror you can see the years piling on as you pass through young adult hood and into middle age. There's Jay's face staring right back at you. The week as Scott letting you see the family relation in the features more clearly.
You grit your teeth as you cum into the condom, taking a moment to get your bearings before you slide it off and toss it in the trash. You pluck at your clothes, noticing they changes along with you to jeans and a tank top sized just right for Jay, but you decide to leave them be. You want this deal with Henry done and you'd just have to strip again anyway.
Scarily, thinking about Henry and sex has your cock suddenly plumping up again. Even in his forties Jay is some sort of sex beast. It makes you wonder about how often Scott's parents must.. You push that thought away. Stepping out of the bathroom you see only the empty apartment. "Henry?" God, it feels so weird to be so big and have such a deep voice. A week as Scott really threw your perceptions off.
"Bedroom."
You follow the voice to the bedroom where Henry is already unbuttoning his shirt. He looks you up and down, eyes lit up excitedly. "Woof. You're even better naked." He takes off his shirt and tosses it aside. It had been so long since you had actually hung out with your brother you still pictured him in your head as a scrawny teen. But with his body exposed you can tell he's been putting in work. He's got a lean build, and he's either naturally smooth or keeps himself that way. He's even got abs you notice with a bit of shock and a twitch of your cock, which he notices.
"Like what you see?" He turns around and drops his jeans, exposing a smooth, round rear. You're getting turned on.. by Henry!
You try to suppress your thoughts as, well, yourself and let the thoughts in your mind that are Jay just kind of lead the way. Doing what he would do. You step up behind your brother, wrapping your arms around him, your dick pressed up against his back, and one of your hands seeking his cock, to give the hard shaft a few teasing jerks, pre leaking down across your fingers.
He turns around in your grip and your mouths meet, tongues eagerly exploring, cocks pressed up against each other. This isn't your brother, you think, just some guy Jay is having a fling with. You push him into the bed, then fall on it next to him. He turns once more so his back is to you, has ass pressed up against your cock. Legs tangling together, you finally line your cock up with his puckered hole, pushing the fat head of your cock inside of him, the two of you moaning in echo.
He wanted a strong, powerful dilf, and you're going to give him that. You grab his cock in your hand, stroking him off in time to your thrusts. You're rough, you're insistent, and he seems to be loving every moment of it, moaning louder and louder with each thrust. With a bit of satisfaction on your part, he comes before you, tensing up around your cock as his cum splashes over the sheets. You get a few more good thrusts in before you hilt yourself in him, finally unloading those huge balls of yours inside of him.
"Fuuuck." Henry says once he regains his breath. You just pull out of him and roll onto your back.
He rolls onto his side and cuddles up against you, but you just sit up and put out your hand. "Condoms."
"Just like that?" Henry actually sounds hurt.
"You coerced me into this, it's not some fucking date. You got what you wanted, now give me what you promised." Jay is a lot more intimidating than Scott, and you use every once of it as you glare at your brother. He sighs and sits up, grabbing the box off the night stand and fishing through it. Eventually he pulls out three condoms and drops them into your waiting hand.
You give your cock and experimental squeeze. It's a little tender, but even coming twice in the span of less than thirty minutes you feel like you might be ready for another run with the condoms. You stand without another word to your brother and head into the bathroom, looking through the three options he gave you.