• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Charlie
  • /
  • Page ⁨4⁩

Charlie

The companionship is easy and pleasant. Now that you knew of some of his sensitives and oddities and he knew of your lack of subtlety and energetic exuberance the pair of you got on extremely well. You don't talk all that much, learning more about each other bit by tiny bit. The conversation might have been a bit sparse but you enjoy each other's company regardless. He was just nice to be around.

At the ponds you stay for a long time, watching the frogs and water fowl do their thing. At one point you stand watching him as he follows a frog along the edge of the pond. You think about Sam's comments. You had to forgive her for what she'd said. She just didn't know Charlie. She didn't understand. She was just being protective and supportive of you after your nonsensical ranting. Once she met him she'd see how great he was.

The day whisks by in no time at all. The pair of you barely make it back in time for your hair appointment.

You say. "If you want to head home..."

He smiles. "I'll wait. I don't mind."

You look at him for a spell. Outside of Sam, your Mom and maybe your sister you didn't know anyone else who would just wait around for you to get a haircut. It weirded you out on some level, but Charlie was Charlie. Weird is what he did. You nod.

You head in and quickly start looking through one of the hair style books they had, you hadn't had time to really think about it. You had not expected your whole day to flash by like it had with your new friend. You smile. Yeah, he was a friend wasn't he? Not just a roomie, but a friend. You snap back to reality as the hair stylist walks up. "Jon? Your turn."

Shit, you hadn't chosen yet. You give the woman a vague description of what you wanted, fade along the sides but with some length up top, and let her work her magic. You'd seen a lot of guys in soccer with that style, you thought you'd give it a try. You sit and watch in amazement as your long locks fall to the ground. You'd worn your hair like this since...you couldn't remember when. Well, not anymore!

When she is done you sit and stare in the mirror. Oh wow, you looked so different. Good, but different. The top still had a decent amount of length, still plenty long enough to run your fingers through it. You still had maybe a half inch long hair as far down as mid way, after that though it got gradually got short. Real short...to the point of non-existence around the base. You run your hands along the side of your head...so short! It felt funny, sensitive, ticklish. Your hairdresser seemed very pleased with the results as she looked you over. You definitely didn't look 'small town' now. You thank her and pay her and you were on your way. You walk out and soon find your new friend sitting on a nearby bench. He looks up and gives you a huge bright grin.

"Nice!" He says.

You chuckle. "Yeah, not bad huh?" You run your fingers along the side of your head, feeling the super short hairs against your sensitive scalp. "Feels weird though."

He stands and reaches up to feel for himself. You were not expecting this! You go to recoil...but you don't. His slender fingers brushing slowly and gently along the side and around the back of your newly shorn head, his eyes focused on the new style. His finger tips rub and stroke the tender skin. Tracing lightly around your newly exposed ear. Time...almost seems to slow down.

Without meaning to you shift yourself forward, moving into his space, moving right up close to him, almost enveloping him with your larger frame, looking down at him as he looks up at you and lightly strokes your head. You stood so close you could smell him. He slowly moves his gaze, those chestnut brown eyes, to look into your eyes...

Whoa! You blink and take a sudden step back, pulling yourself away from his touch. "Uh...yeah. Feels weird dude. I'm so used to longer hair."

He is still gazing at you intently. This time it was your turn to look away, to break eye contact. "I think it looks good." He assures you in his soft voice.

"Sure, thanks. I hope Sam likes it." You say. You then repeat again for no reason. "Yeah, I sure hope Samantha like it."

"I'm sure she will." He replies solemnly.

Together you grab an early supper then head back toward the dorm. You were starting to notice more and more students arriving now. The front of your hall far more busy than what it had been even just this morning. You see two more guys with suitcases and backpacks making their way into the hall.

A few of the new arrivals were out on a lawn tossing a Frisbee around. One of them waves at you. "Hey, wanna join?" They were fellow freshman, like you they looking to make new friends in this new environment.

"Sure!" You call out. Turning to Charlie you say. "Join me?"

He is hesitant for a moment, but he finally smiles and nods. The pair of you jog forward and join the toss about. There were about eight of you tossing the disk and chatting, making introductions, posturing, the usual stuff. Very casual. Charlie is quiet but keeps the rhythm of the game going easily, no one pays him much mind.

At one point the Frisbee is tossed just a bit too far and too high. Your eyes focused skyward you run for it. You run, you leap, you reach. One of the other guys calls out. "Look out!"

CRUNCH!

You feel something, someone actually, collide with your shoulder and side. Being an athlete you keep your concentration and nab the Frisbee from out of the air and land on your feet. You hear a meaty thud as someone lands hard onto the ground beside you. The others howl with laughter and cries of "Ohhhh!"

Looking down at your feet you see little Charlie crumpled on his side. He groans and rolls in pain. The pair of you had been going for the same throw and hadn't seen each other. He definitely got the worst of it. You toss the Frisbee back to the others and hold your hand up to indicate you were done. They wave back and continue their play. You look down and smile. You'd taken more than your fair share of falls like this, you were pretty sure he wasn't too injured.

Kneeling down over him you roll him over to his back. He looks up at you, the pain fading from his expression as he gazes up you. You bend down over him and look him in the face. He seemed okay. As he gazes he goes to reach up in an attempt to touch your face.

You push his hand away. Weird enough him stroking your hair in public. "You okay?" You ask.

He gives you a cringing smile. "Yeah, sure." He just lay there looking up at you, not attempting to move. Just looking. Seeming to enjoy this moment despite the pain.

You laugh. Grabbing his hand you say. "Get up dude. You're okay."

You easily power him up off the ground, he was as light as he looked. You dust him off.

"Gonna kiss his boo boo?" One of the guys call.

You laugh and flip the guy the bird, this elicits more laughter from the others.

Charlie was holding his shoulder and limping. The right side of his body had taken the brunt of both the collision and the landing. "Oooo, that hurts. I'm...I'm just going to go in." He moans.

You follow along. "Lucky for you you are roommate is with a Sports Medicine guy huh? Treatment and rehab is right up my alley." You hold out your 'healing hands' in demonstration.

Charlie is laughing through his pain. "You literally haven't even taken one single class yet."

You just grin as you help him up the short couple of stairs to the main doors. "Don't worry. I'm a natural."

***

Inside the hall you see a lot more people now. The place must have been half full now. The huge roly-poly form of Mama Rose, in a fashion disaster black dress with a bright pink rose pattern splayed across it, was rushing this way and that trying to help all the new young men get settled in. She was in the center of a whirlwind of activity, and she seemed happy as a clam.

Seeing Charlie holding his shoulder and limping she rushes up. "Oh, what happened sweet thing?"

"I fell." Charlie says quietly.

You chuckle. "Sweet thing? Am I a sweet thing too Mama Rose?"

She gives you an exaggerated 'hubba hubba' sort of look up and down your rugged physique. "Honey, if Mama Rose was thirty years younger I'd show you what a sweet thing you were." She growls like a hungry tiger.

You burst out laughing as she smiles and heads off to help some other hapless freshman. The way you heard Colleges were she could probably get in trouble just for saying that, she didn't seem to care. Among her boys she was in her element.

"Oh my god, she's awesome." You say.

Charlie giggles. "She pinched my cheeks when I moved in." Both of you laugh as you continue on your way.

You help Charlie up the three flights of stairs. Your strong hands holding him by his shoulder and left elbow. He accepts your help gladly, leaning into you whenever he needed to. You were really starting to worry about his knee, it might be worse than you initially thought.

"Do you want to see a doctor? I could drive you, I have truck." You offer.

He shakes his head and grunts. "No, I just want to rest."

"Well...let me look at it at least."

You might not have taken classes yet but you'd done some reading as it was a genuine interest of yours, plus you'd been on the receiving end of treatment various times over the years. You walk through the common room where three guys were chilling out. You notice Luiz sitting in the exact spot from yesterday and you give him a nod of acknowledgment He gives a little two finger wave back.

You get into the room and help your roommate onto his bed. He sits on the edge of his bed gripping the edge of the mattress slouched forward, his legs hanging over the side. "Thanks." He says.

You look at him with concern. "Charlie, I was serious. Would you let me look at your knee? I'd just like to check a few things. It could be a serious injury."

He looks up at you and is quiet.

You say in your most disarming tone. "Um...I know, your privacy. Uh, do you have any shorts you could wear or maybe your bath robe? In your jeans I can't..."

He says in his soft voice. "You're worried about me."

You weren't sure if that was a question or a statement. Leave it to Charlie to make an awkward situation even more so. "Well, kinda. I mean I feel kind of responsible. And, this is what I'm going to be studying. I swear, I'll be gentle. I just need to see the knee, that's all."

He nods. "Okay Jonathan...okay..." He sits a long moment without moving, as if he was turning something over in his mind.

"Would you like me to leave? While you get changed?"

He shakes his head. He starts to undo his jeans, unfastening each button of his button fly slowly and deliberately. As if each button was a separate monumental decision he had to make. It is quiet in the room, every second felt like a minute. This was a big deal for Charlie, you felt for the poor guy.

You grab your desk chair and position it between the beds facing Charlie's bed. You then go and lock the door as you try to lighten the mood. "There, no one will walk in. Don't worry Charlie, like I said when I met you. I've seen it all. You ever notice those gross old men that hang out in change rooms? Fuck, they're always naked."

He lets out a little halfhearted laugh, appreciating your attempt.

He stands and turns away from you and grabs the waist of his pants...and stops. He just stops.

You let out a sympathetic sigh. "Hey, you know what. It's okay. We don't have to do this buddy. I just wanted to make sure it wasn't anything serious."

"No...I want you to. I want to." He says in a voice you could barely hear. "It's just...it's only my second day and...I'm not allowed...I'm not allowed to..." He trails off.

You cock your head. What the hell? "Not allowed? Not allowed what?"

"Um...I'm not supposed to..." Nothing more was forthcoming.

"Listen, I don't know what you're talking about. I know you said you had a medical thing. But...you're your own man Charlie. We're out on our own now. No more parent's rules."

"No more parent's rules..." He repeats to himself.

You couldn't help wonder why you were trying so hard to get this man's pants off. Sure you were worried about him, but...that wasn't it. You soften your tone. "It's okay Charlie."

In a whisper he says. "Okay Jonathan."

The trust he was showing you, a man he just met 24 hours ago, touched your heart. This couldn't be easy for him.

He lets go of the waistband of his loose fit jeans and allows them to fall to his ankles. He steps out of them and kicks them off to the side. He stood still as he worked up his nerve. His back was still turned to you...and you were mesmerized.

You didn't mean to, you really didn't mean to, but you couldn't help but stare. You had told the truth, over the years you'd seen it all in the various change rooms and locker rooms...but you hadn't seen this. His butt it...it wasn't... You were so confused. You KNEW he was a guy, you'd seen the bulge, but from behind...from behind he did not look like a guy at all, at least from the waist down. He had a curve to his hips, his smooth pale legs had a shapeliness to them, his ass was...it was beautiful! It was fucking beautiful! He wore tight men's briefs which only acted to highlight the differences from what he was supposed to look like. His cute bubble butt was rounder, wider than it should be...it was the ass of a woman. And a fine woman's ass at that! It wasn't as big and pronounced as Samantha's but it had a cute attraction all its own.

You consciously had to remind yourself who this was in front of you. Your unconscious brain though...it liked what it saw!

He turns back toward you, his head was down and you could see that furious blush through his bangs. Looking back down you see...yeah, he was a guy all right, no doubt about it. Fuck...and what a guy!

You can't help but let out a guffaw. Now that you had a closer look, wow! His prodigious bulge was outlined pretty well through his tight underwear. Hell, it likely rivaled your own, and you were the biggest guy you knew.

"Jesus Christ Charlie! You are hung my man!"

He shifts uncomfortably and looks down toward his pants. You throw up your hands. "Sorry, sorry! I shouldn't have said that." You smile at his blushing face. "It was a compliment. I mean, it's not the axe but how you swing it but...it helps to have a big axe." You laugh. "Dude, you are going to be a hit with the girls. I am telling you."

You pat the bed. "Okay, sit down." You interlink your fingers and stretch them out as you take your seat. "The doctor is in."

***

Charlie takes his seat in front of you. You were face to face, Charlie on his bed and you on your chair. He was up a bit higher than you. Carefully you take his leg and rest it on your thigh. You could already see an ugly looking bruise forming around his knee.

Non-consciously your eyes run up and down his shapely leg, it took everything you had not to run your hands over them. They were pale, a creamy white. There was hair but just a fine light wisp, soft to the touch.

Not like the thick coarse hairs of your legs. With your large strong tanned hands you gingerly begin feeling and probing around his injured knee. He flinches at first then forces himself to relax. You feel the front, around the kneecap, you run your hand along the sensitive underside. You get him to flex it, bend it, turn it. Your steady fingers feeling around at the tendons and joints and muscles. You were pretty confident nothing was really damaged, just a nasty bruise.

You don't say anything however.

You continue to feel his soft supple flesh. Gripping just a little higher up the thigh, running just a little lower down the slender calf. You begin to give him a light massage. No words were spoken, no words were needed. You rub and knead his lithe limb. As you go you begin exploring out from the knee more and more, you oh so slowly start to rub your outstretched hand up his inner thigh...stopping three quarters of the way up. You hear a soft sigh escape his lips. He sat perfectly still, watching you work his flesh in your large steady hands.

Your eyes were locked on his shapely leg, you freeze as you stare.

Fuck. Fuck. Fuck no. No! This isn't happening right now.

You sit still. He sits still. Both of you knowing damn well what was happening but not acknowledging it. You could just make out his crotch peeking out from under his layered shirts. He was getting hard. Fuck...you were getting hard! You also notice a dark patch of wetness beneath his balls, probably sweat from the Frisbee...but you hadn't noticed it before. You grit your teeth. NO!

You push your chair back and too abruptly set his leg back onto the ground. He lets out a little yelp.

You say brusquely. "It's fine. It's all fine. Just a bruise." You tear your eyes off of him, you were furious with yourself. Fuck you wanted him right then. You fucking wanted him!

He sits still. In his soft voice. "Okay Jonathan. Thank you."

"Why don't you call me Jon?" You snap. "Everyone calls me Jon. Jon! Everyone. Why are you so fucking..." You cut yourself off.

"Oh...um...oh...I'm sorry..."

You sigh as you grip your forehead. "Sorry. Christ, sorry Charlie. I don't know what's gotten into me. You can call me Jonathan if you want to." You wanted him to call you Jonathan, it was different, it was special. In that moment of caring you become a slave to your desires once more.

You look back up at him. You see in his wide brown eyes he was just as confused as you were. He didn't know what to do or say. But like you he didn't want it to end.

"How's...how's your shoulder?" You move to sit beside him on the bed. He doesn't answer you, he just stares at you with those eyes...those incredible eyes.

Without hesitation you reach out and brush his hair back from his face. You hand resting gently on his smooth slender neck. Your gaze was locked in his. "Your shoulder okay Charlie?" You whisper as you begin to rub the back of his neck gently, his thick soft hair caressing the back of your hand. "It's okay?"

He gives you a slow barely perceptible little nod yes. He was lost in the moment. His breath picking up, that adorable flush brightening his face, his mouth slightly parted. He didn't move a muscle. He wasn't resisting you in the slightest.

You weren't thinking about his shoulder anymore. You start to run your fingers through his thick rich raven black hair, it was so different from Samantha's straight thin blonde locks. You reach up with your other hand and, after a brief pause, so very lightly begin tracing your index and middle finger around the edges of his full plump kissable lips. His breathing picks up more. You trace and feel those full pink lips. He...he kisses the tip of your middle finger...and again...he opens his lips and...sucks...sucks so lightly on the tip of your finger. You watch mesmerized as he tenderly licks and sucks the sensitive tip of your middle finger, his beautiful eyes locked on yours.

Reaching back around you cup his head with both hands, your fingers running through his hair, your inner wrists touching his dainty jawline. You pull him toward you, reaching out to him with your lips. He closes his eyes and lets out a long hot breath, parting his lips for you. You pull him closer...closer... Your nose brushes softly against his... Closer...

BAM! BAM! BAM! BAM!

A loud hammering knock on the door drums through the room shattering the fragile intimate moment.

Thank God!

You shake your head, shaking off his bewitching effect on you. You stand abruptly, actually pushing roughly off of him. Forcing him back onto his bed. You spring away from him as if he was red hot. You hurry to move toward the door. "Put your pants on. Put your fucking pants on!" You order your roommate in a hushed but brisk rude tone.

You instantly regret your harsh tone. Deeply deeply regret it. You wanted to apologize, you wanted to scream at him, you wanted to jump out the window, you wanted to jump on him and ravish him. You didn't know what you wanted! Your head was a dizzying confused jumble.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Charlie
  • /
  • Page ⁨4⁩

All contents © Copyright 1996-2024. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+1f1b862.6126173⁩

We are testing a new version of this page. It was made in 20 milliseconds