Chapter 59
by
Mr Nice Guy
What's next?
Taking Care of the Big Guy
Riley hit the bed giggling, the plush comforter catching him in a soft heap. A heartbeat later, Chase landed beside him with a thud, both of them breathless from laughter and too many failed attempts to sneak quietly up the stairs.
"Shhh!" Riley whispered, hiccuping mid-giggle as he slapped a hand over Chase's mouth. "We're gonna wake Isa."
Chase grinned, pulled the hand away, and kissed Riley's fingertips. "I don't care."
Neither did Riley.
He didn't even remember getting from the club to the house. It was a blur of streetlights and whispered things in the back of a car. The memory of Chase's hand on his waist hadn't left him since they stepped off the dance floor, the memory of Chase's lips on his own threatened to drown him in a swirl of emotion. And now they were here.
In his room.
Alone.
Together.
Riley looked up at the ceiling, heart thudding. The hem of his dress had slid up when Chase carried him up the stairs, his legs and panties on fully display for his audience of one. The lipstick that he had painstakingly applied had long since smudged off, the scent of Chase's cologne sunk deep into his skin. He felt floaty, like the whole night was still playing in slow motion.
Chase turned toward him, propping himself on one elbow, eyes soft. "You were incredible tonight."
Riley smiled without thinking. "You were the star, big guy. I was just there to make you look good."
Chase leaned in and kissed him, and the moment their lips met, something inside Riley twisted. Warm. Dizzying. Frightening in the best way.
He could still feel Chase's arousal pressed against him from when they'd danced. Riley's brain, marinated in **** and fuzzy, had worried about his boyfriend. The poor man needed to relax, needed to meditate. Yes, he'd won the game, but he had a whole season ahead of him. And there he was, dancing at a club, needing to unwind, with his big, beautiful cock threatening to derail all the joy his victory should have gotten him.
It was a good thing Chase had a girlfriend like Riley.
Without taking his lips from Chase's, Riley slid his hand down his boyfriend's torso and began to massage the big man's big cock through his jeans.
That did the trick. Chase's kissing intensified, giving Riley the indication that he was on the right track, that he was really understanding his boyfriend's needs. Lately, he was finding himself loving Chase staring at him, much more than usual. Riley was starting to think of himself as a bit of a detective. He had a mystery to solve, the mystery of his man. Chase obviously loved Riley's body, why else would he want to spend so much time with him, but what parts did he love best? He'd been showing off as much as possible, teasing here, revealing there, but there was really only one way to get to the bottom of it.
With great willpower, Riley let his lips leave Chase's, a line of spittle connecting them for a moment as he sat up. He instantly felt empty, disconnected, craving his boyfriend's touch, but Riley knew that sacrifices had to be made for the greater good. Then, letting go of Chase's cock, he slid his hands behind him and unzipped his dress. With a grin as he watched Chase's eyes go wide, Riley pulled the dress off and tossed it, unceremoniously, across the room.
"Do you like that, big guy?" Riley giggled, reaching down and pulling Chase's big, meaty hands to his chest, encouraging his boyfriend to squeeze his girls. "It's all for you, you know. All my content, all my cheering, this body, it's all for you."
As Chase enjoyed touching Riley, Riley thought he'd return the favour. He reached down and unfastened his boyfriend's belt, then his button, then slowly pulled down his zipper. Now that he had secured the enviable position of Riley's girlfriend, he knew that it was his responsibility to take care of the football star's needs. To please him. And if it was going to do that, if he was going to be in Chase's life long-term, he would have to be creative. Using his hands, using his mouth, even using his girls, those were great, but Riley had an entire body to use. Were there other ways to please his man? Would Chase like it if he used his feet? How about his hair? Then there was all the work he'd put in at the gym on his ass...
Riley slid his boyfriend's jeans down his legs, followed by the boxer shorts that were hidden beneath. His boyfriend's clothes then joined the pile of Riley's own discarded attire. Then, in a moment of decisive action that Riley was sure Isabelle would be proud of, he swung one leg over Chase's body, straddling the almost naked man.
And then, with the wonderful feeling of Chase's hard cock pressed up against Riley's rear end, through his panties Riley lay down and kissed his boyfriend again. This time it was soft, loving, and generous. Remembering his success on the dance floor, he ground his rear end into Chase's penis, not only making his boyfriend moan in pleasure, but giving Riley a true sense of closeness to his man.
This is how you take care of your boyfriend's needs, he thought as he felt Chase's hands reach around and squeeze Riley's ass.
"You're so fucking hot," Chase said, his lips leaving Riley's to take a breath, "I can't believe I'm with you. I want to fuck you so hard you won't be able to see straight."
Fuck.
Riley had used that word before, but not like that. Fuck. What was Chase talking about? There was something, bubbling just below the surface, a flicker of a memory that didn't seem to belong. It was elusive, and despite his attempt to nail it down, Riley was unable. But it meant something, something important, something he thought he should know.
The question would have to be answered a different day. He could always ask Isabelle. She seemed to know so much more about the world, about relationships, than Riley did. For now he had a boyfriend with some serious needs, and since Riley was an expert at meditation, he decided it was time to take care of things.
Deciding that convenience was the best way to go, Riley took one hand, licked it from top to bottom, then reached behind him and slid his wet hand up and down Chase's cock. There was a slippery liquid escaping from the tip that added to the lubricating effect of his hand. Then, using the tip of his boyfriend's erection to slide his tiny panties aside, Riley positioned the penis up against his anus, something he'd never done before, but in that moment made perfect sense.
If he had a hole, why wouldn't he use it to please Chase?
Then, lips back on his boyfriend's, Riley pushed backward, shivering as he did.
It was something he'd never experienced before, penetration from a big man. Of course, Riley had never had a boyfriend before, so it was to be expected that he would be experiencing novelties as their relationship blossomed. Slowly, carefully, he moved up and down on Chase's erection, using the muscles he had expertly worked at the gym to hold his ass tight, squeezing and moaning as he did. Chase began to match his rhythm, a good sign that he was on the right track to being a more efficient girlfriend, learning to use all the tools at his disposal.
Chase's hands moved up to Riley's hips, squeezing, forcing himself deeper into Riley. It wasn't unpleasant exactly, but it was unfamiliar. That didn't matter. Riley's own pleasure was secondary. Chase's needs being met was his only concern. What he wanted, what Riley needed, was to have his boyfriend be taken care of, to know that Riley would be there for him, would be whatever Chase wanted him to be, whenever he wanted him to be it. That was the role of a girlfriend, after all.
Imagining what GirleyRiley would do on screen in this situation, Riley moaned deeply and loudly, one hand reaching behind him to massage Chase's testicles, the other softly touching his face, his elbow sharing the load of holding him up with his chest. Not wanting to be outdone, Riley increased his grinding, working Chase's erection, teaching him to meditate with much more intensity and purpose.
Chase began to shake. His eyes squeezed shut as his breathing became raspy. Seeing this as a clue, Riley stopped kissing, his pillowy lips just brushing his boyfriend's, but didn't stop his gyrations. He watched the reaction of the big man, his big guy, as his face grew redder and redder.
And then...
Blammo.
Like a gunshot, Chase's cock began to erupt. All the tension, all the worry, all the fear of the future, of football, of the world, filled Riley's rear end as Chase groaned loudly, shaking as he did. He could feel it, leaking out of him, filling his panties, dripping onto his smooth thighs. Riley couldn't be prouder. He had done it. Something he'd never done before. Riley had been creative, had thought of a new way to take care of Chase's needs.
A moment later Chase had stopped his spasming. Knowing his cue, Riley inched forward, allowing for his boyfriend's cock to slip out of him, leaving him feeling empty, missing it instantly. He lay down on the big man's chest, looking up and gently kissing his neck.
"How did I get so lucky?" Chase breathed when he finally could find the words.
"I'm the lucky one," Riley said sweetly, Chase's heartbeat in his ear, "I'm the luckiest girl in the world. Taking care of you is like... it's like... better than..."
Riley didn't get to finish. Chase's lips had once again found his own. This time it was less hungry and more loving. He didn't just feel it on his lips, but also in his heart. He had found his man, his purpose. All Riley had to do was make sure he kept pleasing him, taking care of his needs, and his life would continue to be the dream that it had become lately. He couldn't imagine his life going any other way.
What's next?
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Crossdressing Stories
A collection of separate stories that all involve guys ending up in dresses
A collection of separate stories that all involve guys ending up in a dresses
Updated on Feb 22, 2026
by Dayeandknight
Created on Feb 1, 2018
by Dayeandknight
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