Charlie

You look down between you as you slowly and gently stroke her hard cock with more conviction. You would not leave her like this.

You take a deep breath. You could bring her off with your hand, you could even just let it be as you were sure she wouldn't complain. But...you wanted to make a statement. Like with the blowjob, you wanted to show her that you loved her and her unique body. You wanted to prove to her that you would be her partner in all things.

Your eyes focused you continue rubbing her.

"Mmmmmm." She hums as she really began feeling the excitement you were stoking within her. "Ohhhh my...mmmmm..."

As you stroked you began thinking of your relationship with her more and more. You knew what you had to do, what you at least had to offer.

She seemed to sense your distraction. She open her eyes and looks up at you, sees you focusing on her throbbing hard dick. Reaching up she strokes your stubbly chin. "What is it?"

You look to her. "I love you Charlie." You were repeating yourself now, but you just couldn't express it enough. The words seemed to fall short somehow.

She smiles. "I know. I love you too."

"Charlie..." You swallow hard. "...when you, when you dreamed about being with a man, um, how did you imagine him taking care of...this." You stop your light strokes and give her a little squeeze down below.

She blushes. "Well, like you did earlier, like you're doing now. What do you mean?"

"Just with his hands and mouth? That's all you ever wanted? That's how you imagined your partner would satisfy these types of needs?"

Her expression gets more serious, though just as loving, as she understands where this was going. "Jonathan, it's okay. I don't want you to do anything you are uncomfortable with. We've got time to figure things out."

You press, ignoring her kindhearted defection. "Was that all you ever wanted?" You ask again. "Tell me Charlie."

"Jonathan..." She looks at you and honestly answers. "...I...I was assuming. You know...I was assuming we'd have each other...um, in every way. Eventually."

"Ask me. Just ask me." You whisper. "Please."

There is a long quiet moment as she strokes your face and stares at you. "Jonathan." She takes a breath. "Jonathan, may I, um, have sex...um, anal..." She falters and blushes as she tries to find the words. You wait patiently.

She finally finds her voice. "Jonathan. May I fuck you in the ass?"

You nod and whisper without hesitation. "Yes."

You share a special little moment as her loving gaze gets even more so if that is possible. She knew what it meant for you to offer this to her.

You had needed to know first that it was what she wanted. If she didn't want it you wouldn't do it. But she did and so you would. You knew you didn't need to and yet you felt you must. You wanted to give yourself too her in any way she desired. You wished to prove your love for her. No lie, you were nervous. Worried. Even a little scared. This was something new and unexpected, yet you felt nothing would stop you.

"I'm...um...really big. Like you." She warns, worried about you.

"I know."

"Are you sure? It's okay if tonight you don't want to." She kisses your chest. "You're sure?"

"I'm sure." You reply. "For you Charlie, only for you. I am sure."

"This night is better than I ever could have imagined. I can't wait to feel you Jonathan." You both embrace and hug each other tight.

You take a breath and then let out a nervous laugh to break the tension. "Okay, first we need lube. Lots of lube!"

She smiles wide and laughs along with you.

***

Untangling yourself from your lover you kiss her and get up to head to the bathroom. Lube...what the hell did you have around to act as lube? There had to be something. As you go you are surprised to feel Charlie following right in behind you, her hands on the small of your back. She is giggling in excitement.

As you reach the washroom you turn and take her in your arms and begin making out with her once more. You really couldn't get enough of one another, it was like an addiction that couldn't be sated. Her straining hardness reminds you why you're here.

You laugh. "God damn Charlie..." You leave the rest unspoken.

Turning you start rummaging around through your things. Soap, toothpaste, hair product...shit. None of that would work. Shaving cream...you now smile in understanding as you see Charlie's unused razor still sitting there untouched, back to the matter...after shave, shampoo...shit, shit, and shit. You needed something good, glancing over at her big hard cock, something really good.

Charlie takes down a tall clear bottle. Aloe Vera gel, for dry skin. She smiles and offers. "I think this will work."

Taking the bottle from her you squirt a little onto your fingers and swirl it around with your thumb. It was slippery enough, and it smelled pretty good too. You nod, confirming your approval. The pair of you head back into the room hand in hand. You didn't want to be apart for even a second.

As you return to your bed she pinches your butt and you start. "Oh!"

"How do you want me to...ya know." She asks.

You stop to consider it. "I'll day down on my stomach and...no wait..." You think some more, you'd like to control things if you could. "I'll be on my hands and knees...no..." You wanted to see her face. She grabs your firm muscled buttock in her hand and begins massaging it, she was getting excited for this. She was pressing into you, kissing your toned muscled back and shoulder, her shaft firmly against your hip.

You finally decide. "I'll be top, you lie down Charlie."

She just nods and follows direction. She lies on her back, legs together, her mighty tool proudly atop her at full mast. She is biting her bottom lip, a smile across her face like a kid on Christmas morning. "Oh my god, I can't wait to feel your ass Jonathan."

You are taking deep breaths as you ramp yourself up for this. "I expect the same from you at some point."

She nods rapidly. "Of course, of course." She waves you toward her. "Come on, come sit on my cock."

You blurt out a guffaw. "Patience, patience! Geez." You were keeping your voices down now that the quiet of the night was starting to settle over the dorm.

He brings her hand up and bites her finger like a guilty naughty girl. "Sorry...I just...I'm pretty excited."

Taking the bottle of gel you begin slathering her long lady schlong with copious amounts of the fresh smelling substance. She giggles. "Oooo! It's cold!" She looks down. "That's a lot."

"Damn right it is." You quip. Holy shit, you were really going through with this.

Setting the bottle on the mattress beside her to keep it hand you crawl up on top of her. Her eyes scan you body with transparent lust. "My god...you are one beautiful man Jonathan. I am so lucky, you are too good for me."

Leaning down you kiss her and shake your head. "Not on your life Charlie. I am all yours and I wouldn't have it any other way."

Looking down under you you see her dick begging for attention. Fuck, you swore it looked bigger each time you looked at it. Best not look at it. You gaze back up at her excited face. She lay there, allowing you to control how you did this, though you could tell she wanted to get going.

You crawl up a bit. Reaching down between your legs you soon find her cool gel coated rod. Without looking you position it and yourself around until...you felt her uncircumcised tip rub between your ass cheeks. Ohhhh boy...almost there now...

Her hands come up to hold you by the sides, by the hips, like you would do to her if she was riding you. You position it a little better, you bend so your cheeks spread, you feel her tip make contact with your tight closed sphincter. You let out a long sighing breath and...relax. As you do this, with surprising steadiness, you simply sit back.

Her fat knob hits resistance, pressing against your anus, and just...stops. Another exhale and you go again, this time more forcefully. Yo

That did the trick! Her super lubed cock presses...presses...presses...then WHOOM, straight up and in!! Way more than you meant to take all at once! Damn near all of it! Both you and Charlie grunt, but for different reasons.

Your back arches and you let out an almost comical sounding. "GAWWW!" You just sort of freeze up as your overwhelmed mind and body comes to grips with this new sensation. Your sphincter tries to tighten and shut but it is stretched by your lover's thick cock. Charlie's eyes roll up into the back of her head as she relishes the sensation.

Jesus Christ! She was fucking big. Not that you had any frame of reference...but you could tell! It takes every ounce of control you had to fight the instinct to leap off of it.

It was interesting...yeah, interesting. It didn't exactly hurt though there was discomfort, more from the totally alien feeling of something penetrating you than anything. You felt...full. So full. With that fullness came a pressure, a...wonderful sort of pressure. Your cock suddenly twitches to life. The most disconcerting part was the depth. She was a good seven inches in and...it just felt...weird.

In for a penny in for a pound. You sit down the rest of the way, taking her all the way in. You feel her fine muff hairs tickle our ass. She groans once more and is absolutely over the moon as her eyes return to you and focus. As she fills you to the brim your cock surges once more, already half erect and growing fast.

"Ohhhhh Jonathan. This feels...ohhhhh I can't even..." She had a silly grin pasted across her happy face. This was definitely living up to expectations. "Oh man, you look so hot up there right now. I can't believe I'm inside you right now." Her hands grip your hips tightly.

She goes to thrust but you stop her, placing the flat of your hand on her soft stomach. "Wait, " You hiss through clenched teeth. "just let me, okay?"

She nods. "Okay Jonathan." She lies still and waits for you.

You just sit there a moment, allowing your body and mind to adjust and adapt. After a few deep breaths you could feel yourself relax, the more you relaxed the better it felt. You pull yourself forward slowly, you felt ever last inch of her as she slid out of you. You push back again, once more you feel her every long inch as it fills you up once more. Fuck, this fullness you were feeling, there was this one spot she was pressing into...god damn that felt good. You groan as you bottom out once more.

"Yessss." Charlie breaths out. "Oh yes. Keep going, please."

Forward...back. Forward...back. Forward...back. You were getting into this, establishing a nice cadence.

Forward...back. Forward...back. Forward...BACK! On the next one you slam down on top of her. You let out a low rumble that shakes your rib cage. Each one was feeling better than the last. If you moved just right, arched your hips in just the right... "Ohhhhhh..." You moan. That pressure, that delightful mind bending pressure. Your cock is almost fully at attention and already leaking precum across her pale stomach.

Charlie is breathing heavy. "Oh sweet Jonathan. Oh my lord, your ass...it is incredible." She looks at your own bliss twisted expression. "Feels good?" She asks.

You just nod and grunt. "Uh huh."

You begin riding her with gusto now. Each backward motion a bit quicker and more vigorous than the last. God she filled you up just perfectly. ANY bigger or thicker and it would have hurt like hell. You ride her hard. She squirms beneath you, enjoying everything you were doing.

This was feeling incredible but...if you tried another angle...it might be even better.

You sit up tall and bring your hands in behind you for support, leaning backward. You bring your knees up in front of you, your feet planted to either side of Charlie's svelte torso.

Charlie reaches up and place her hands on your knees. "Oh wow!" She exclaims. "Oh wow, if you could see how good you look right now. Oh my god!"

The change of angle was simply magical. That pressure from before had now shifted to hit your button full on. Fucking...WOW! A warm burst of energy radiated out from your nether regions.

With all your weight on your hands and feet you begin thrusting yourself up and down on Charlie. From this position you could go much faster.

You begin moving your self up and down. Slowly at first as you found the best angle and tempo for the new position. Soon you found your groove and you bounce your virgin ass on her mighty pole. Both of you are letting out sounds of pleasure, a carnal duet sung just loudly enough for the two participants.

As you really start picking it up your balls and perfectly stiff cock begin flapping up and down to your motions. Your hard on like the handle of an old fashioned water pump, flailing up and down and up and down. Your heavy balls swinging wildly with your movements. Despite having nothing touching them just the motion alone along with Charlie filling your backside was enough to stimulate you. If you kept this up you were pretty confident you could achieve climax.

Charlie is groaning and gasping as you pounded down onto her, you feel her begin to thrust back up at you. Each impact of your contact rattling both your bodies. Her little tits bounce and jiggle. Both of you are still trying to stay as quiet as possible. You both move together as she fucks your ass hard and fast.

An idea strikes your little genius. Grabbing the Aloe gel she squirts a big glob into her hand. Rubbing her hands together she reaches up and takes hold round your near cumming manhood. She just holds firm with both hands and allows your own movements to do the work. You let out low quiet grunt.

As you thrust your hips up and down on top of her you were getting double the pleasure. Your ass being plunged into while simultaneously your slick cock being stroked. When you go up Charlie's lady boner slides out of you and her gripping hands go down round the base of our tool. As you go down you are filled to the limit, that pin point perfect pressure making you see stars, and her hands come up round your swollen knob. It was absolutely overwhelming!

Both of you are close. Both of you groaning and whining and growling as you struggle to keep quiet.

A high pitched whimpering whisper she says to you. "I'm gonna cum baby. I'm gonna cum baby. I'm gonna cum deep in your ass baby. So deep. Ohhhh..."

That was it, you could take no more. On the next downward motion you buck and snort and send a thick creamy white rope of hot cum arching, as if in slow motion, over her writhing body and down onto her face and hair. She closes one eye as it lands across it.

Just a half a beat after you explode so does she. Even as she desperately tries to maintain concentration on milking your exploding cock hers erupts inside of you. She jerks upward and you feel her shaft throb inside of you.

You blast rope after rope of your seed over her face and neck and tits as she pumps load after hot load deep inside your bowels. She milks you with her hands as you do the same with your quivering asshole.

After one of the most intense moments of your life...you finally come back to earth. Both of you let out a long and oh so very satisfied sigh. You pull yourself up off of her, feeling each inch of her spent dick as it slides out of you, followed by a flow of her warm gooey jizm. You gasp at the sudden emptiness of it.

In a daze you crawl back up and collapse beside her. You throw your tired arms around each other, you kiss despite her facial, and you just...relax.

Your bed was wet and sticky, the place smelled like a whore house next to an aloe vera garden. Your ass pulsed and shuddered as it returned to normal, cum leaking from it. Charlie a gooey mess. Your cock still dribbles a few last drips of cum, as does hers.

Unable to do anything else you and Charlie just hold each other and enjoy the moment.

***

You lie together for a time in silence. Eventually the pair of you get up and go to share a shower together, your bodies press together in the small walk in shower. You clean and caress each other's sweaty tired flesh. Heading back to the room clean you go to lie together on Charlie's unsoiled bed. You turn off the light along the way. With the curtain drawn the room is almost perfectly dark. You hadn't left each other's touch for even a moment, together you make your way to her bed.

You were both still nude as you slide under his sheets. The single bed requiring you to lie pressed together, which you would have done in a bigger bed anyways. Her soft smooth clean skin rubbing against yours.

You kiss, you stroke, you caress. An all consuming feeling of peace and contentment settles into you as you hold her close.

It is finally Charlie that broaches the questions you had thus far kept quiet. In a whisper she says. "My family is like this, it's not just me. My mother, my aunts, my sisters and cousins." There were more like Charlie!? She continues. "The family I have down here, them too I am pretty sure. It's...it's our family secret Jonathan. Please don't..."

You hug her tight and kiss her forehead. "I won't say anything if you don't want me too. Although, wouldn't it just be easier if you guys lived out in the open?"

She is quiet for a time. "Yeah, maybe. But it is always what we've done. And...we don't want the attention. It's just always what we've done. A few of us do live openly, sort of. The whole truth never revealed though. I don't know how my American family manages but we've got it pretty locked down back home."

"So there are a whole bunch of Canadian women like you? Huh."

"Not just Canadian. We're starting to spread out. My Grandma had a big family...with multiple partners. It's weird, no one born into our family is normal. Doesn't matter if we're the mother or the father. We are all unique...in one way or another. I think this Dr. Bailey might have some answers." She kisses your chest lightly. "I'm sorry I kept secrets from you Jonathan. It wasn't fair to you. Living with a woman who you thought was a man."

You chuckle. "It explains my attraction anyways, although...it wouldn't have mattered in the end. Charlie, why live as a man?"

She lets out a sigh. "It kind of just grew out of my childhood. Most of us are presented as girls, but sometimes we're made up like boys. The ugly ones I guess."

"Stop that." You hug her tight once more.

"Anyways. Everyone thought I was a boy growing up, and since I ended up with smaller breasts and slimmer hips...I just kept it going. Honestly, it is easier in some ways...harder in others though." You feel her hands run up and down your chest and stomach. "I'm so happy Jonathan. I am so happy to be with you. I would be so proud to be with you...in public I mean. But, you know, if you want to keep us a secret...I'll understand. I'll totally understand. I'll keep quiet if you want me to." She nuzzles her cute button nose into your pec.

"Shit, that reminds me!" You shoot up in bed.

"Huh?" Charlie starts.

You step over your lover and slide out of the covers.

"Jonathan? Where are you going?"

"I'll be right back." You stride for the door. Still naked as the day you were born you stroll casually down the hallway. Five of the guys are in the common room playing cards, Luiz is there of course. They look up at you in surprise. Some groan, some laugh, some turn their heads, some just stare in jealousy.

Walking over to the white board that had been set up you grab a blue dry erase pen and go down the column of 'Most likely NOT to lose their virginity'. You go down the line crossing out Charlie's name over and over again. The stunned men in the room just stare in disbelief. Clapping the cap back on the pen you hold it out and do a classic 'mic drop' with it.

"G'night boys." You say with a grin and a wink. They sit in silence and watch you leave. The others were stunned while Luiz seemed genuinely happy for you.