Chris becomes Christy

"C'mon you owe me, Chris." Renee pleads with me.

I just stare ahead at the tv blankly trying to ignore her.

"Chris!"

"What?!" I shoot back annoyed now.

"You owe me!"

"But this is ridiculous." I say.

Renee is my girlfriend and she's a cute little auburn haired girl with big green eyes and pale skin dotted with freckles. We've been dating for about six months.

"I do everything you ask me to do for you. You can give me this." She pleads.

"Why can't I go as Superman and you as Lois Lane?"

"Because it was set up like this by my boss. All the employees significant others are swapping roles."

"Like who?"

"Denise's husband is going as cat woman to Batman. Jennifer is going as Dezi Arnez and her boyfriend is going as Lucy. That's all I know."

I sighed, "but this?" I say waving at the outfit she has laid out on the couch next to me.

"Yes, it's all I have on hand and we're about the same size."

My crux I carried all my life, I'm not a big guy at all. I'm barely five feet five and thin.

I look at the outfit, a black skirt and white blouse with black lace panties and white bra and pantyhose finished off with shiny black open toe four inch pumps.

"It'll never work." I say thinking that will work.

"It won't if you don't try."

"This sucks." I say.

"Chris, I'm trying to make a name for myself with this company. If we go there and don't do as Mr. Davenport wanted it'll look bad on me. Please Chris." She says sitting next to me.

"Fine." I say defeated.

"Yay!" She squealed happily. "Come on, you have to get ready."

She leads me to my bedroom and tells me to shower and use a hair remover for my legs. Then shave whatever doesn't come off. When I'm done she'll do my makeup before I change into my costume.

While I'm in the shower I ask her why do I have to shave my legs just for tonight.

"It's for the party Chris and the hair will grow back. Speaking of hair, you won't need a wig with that beautiful head of hair of yours. I'll just style it better than your usual ponytail."

"Great." I mumble.

"What?"

"Nothing."

"Don't be such a baby, Chris."

Since I was shaving I did shave the stubble around cock and balls as I always do anyway. I liked that feel and she appreciated it too.

After my shower she sat me down on the toilet and began doing makeup after washing my face.

When she finished she stepped back and her eyes widen which freaked me out. I asked what was wrong and she says, "nothing Chris. You just look like Jennifer. Holy shit."

Jen is my older sister and she just so happens to be very pretty. That can't be what I look like.

"Let me see." I demand.

"Not yet, get dressed first." She says taking me back into the bedroom.

She walks me past the mirror and into my walk in closet and hands me the panties first. I pull these up my legs and the satiny fabric gives me a hard on right away.

"That's not going to work." Renee says pointing at my stiff little cock.

"Well?"

"Well what?" She asks indignantly.

"C'mon." I say nodding my head down towards my wood.

She sighs, "fine. But you best be the hottest Lois Lane ever."

A moment later Renee is on her knees sucking my dick until I explode all in her sweet mouth. It didn't take long.

"Now finish getting dressed."

"Why aren't you dressed yet?" I ask.

"Because it's a one piece suit and I can do that before we walk out."

Next I had to put on the bra and it was a little tricky but we got it on and she filled the cups with C size breast forms. Next came the hose, thigh high pantyhose with elastic bands up high on my thigh. I really have nice legs I thought to myself.

"Put the blouse on first this way you can tuck in your junk and the blouse."

I pull the blouse on and button it up and it's rather tight around my faux bosom. Then I tuck my junk and it hides away nicely. It also feels a little sexy.

Next is the skirt and it's so short you can almost see the bands of the thigh high hose but only when I'm bent over.

Last came the shoes then Renee brushed out my hair adding a white beret giving the illusion of bangs. She gave me hoop earrings and bracelets and I put those in replacing my simple small silver studs I already had in my ears lobes.

"Oh shit." Renee says in a low tone.

"What?!" I panicked.

"Wow, I'd fuck you. Your really hot Chris."

"I am?"

"Yes. And you don't look like Jennifer. You look better."

"Not possible."

"Really? Go look." She moves out of the way and I walk across my room to the mirror on the wall and stand there stunned, I resemble Jen but she's right, I'm hot. From my legs all the way up. Like a sexy business lady in a tight suit. I have nice girly hips, a great little bubble butt and amazing legs.

"Put the heels on babe, you need to practice walking around and use a softer femme voice from now on." I gave a her a confused look and she said, "you have to play the part. C'mon let's do a shot."

I slip the heels on and stand up cautiously before taking a step gingerly. What happened next surprised both of us, I walked in them like I had always been walking in heels. And I'm finally taller than her.

We do our shot of whiskey and order an Uber and while we wait she gets her costume ready. When the Uber is less than five minutes away she pulls it on and we head out to the car.

It's a fifteen minute drive to her boss's house and I'm seriously nervous. Renee keeps telling me to relax, there are other guys dressed up too. Maybe not as hot as me, she adds with a wink.

Then she whispered in my ear, and when we get back to my apartment we will have lesbian sex.

Now I was excited all over again.

Her boss's house is pretty normal in an above average suburban neighborhood. There are several cars parked on the street and the driveway is packed.

We get out and she keeps telling me to remember to be as ladylike as possible. She said I was doing very well so far so keep up the image.

The party was freaking amazing and Renee was spot on with her descriptions of her coworkers and their significant others whether it was a guy or girl the other went as the opposite sex.

I can't even begin to tell how many times I was hit on by men and women and the attention was wonderful. And the hands, my ass was felt up so many times that at one point I stopped fighting them off. I actually began to enjoy it.

The only person at the party that didn't mix it up was her boss Paul Davenport but I could see why, he's older and the majority of people here are our age, mid twenties to early thirties. He's easily in his fifties and he's divorced so he didn't have anyone to switch with.

He's a tall lanky guy with dark brown slightly grey hair and matching goatee. He wears glasses over his deep blue eyes and has a very nice smile.

All night he checks on the party goers making sure everyone is having fun. I spoke to him briefly at one point but it was kind of in passing. I was spending most of my time with the guys and as it turns out, not one of them knew Renee even had a boyfriend.

That was odd.

It was getting late and I was fairly buzzed and couldn't find Renee anywhere.

My charade as a girl should be over but I kept up the act because she said her boss would announce a winner at the end of the night. And I wanted to win after going through all this but it was past midnight and a lot of people had already left.

I went looking for Renee outside on the back deck and side deck and she was not there. I went upstairs and to every room and she was nowhere to be found.

The last place to look was the basement again and as I went down there I heard moaning and grunting.

My heart began to pound harder and harder hoping beyond hope that the moaning wasn't from her.

I turn the corner from the stairwell and into the main room and walk down past the bar down a small hallway to the movie room.

There on her hands and knees is Renee being fucked hard from behind while sucking a big cock. She's moaning while the two guys are grunting and panting railing her from both ends.

I quietly step away and turn to leave when I see Mr. Davenport standing at the end of the bar. We see each other and he gives me an empathetic look as I rush past him and back upstairs.

I find a quiet room and try getting an Uber but the closest one is half an hour away but I keep trying.

It was then the sting of tears hit my eyes and I was suddenly crying. Not because I loved her or was jealous that she was getting pounded by two guys but because of the humiliation I felt. Dressed as a girl at a party full of people I didn't know I felt all alone.

"Are you okay?" I heard a man ask me from behind.

Okay so I wasn't physically alone.

"Yes I'm fine." I say staring out the window.

I hear the man walk closer and I'm too embarrassed to let him see me crying.

"It's Christy, right?" His voice is low and soothing. It sounds like Mr. Davenport.

I've been calling myself Christy all night after Renee introduced me like that. "Chris actually."

"I prefer Christy, is that okay?"

"I guess." He's so much closer now I can hear him breathing.

"Is Renee your girlfriend?"

"I thought she was."

"I'm sorry. That's incredibly inconsiderate of her."

"She can do whatever she wants." I almost hiss.

"So can you."

"I could never land two girls."

"I didn't mean that. I meant you are free now to be...Christy."

I stood there staring out the window not totally sure what he meant but I had an idea.

"You're are the sexiest person here, Christy." I can feel his breath on the back of my neck, he's that close now. "There isn't a man or woman here that wouldn't want to be in your company tonight."

I stood so still feeling a twinge of excitement in my loins. But why?

"Alone with you." He says as I feel his hand on the small of my back.

"Do you even know how hot you are?" He asks me.

"No."

His hand slides down over my ass and the chills race up and down my body.

"You're an incredibly hot girl and I want you, Christy."

"But I'm not gay." I say pathetically.

"You don't have to be." His hand is groping all over my panty clad ass and I like it.

"I'll make you feel like the beautiful girl you really are." He says just before he kisses the back of my neck. Those chills went right down my back and my body betrays me and pushes back against his hand.

"That's right Christy, just enjoy the moment." He says as he places little kisses all around my neck and behind my ear raising the hairs on my neck tingling my groin area even more.

"You're so sexy, Christy." He says as his arm wraps around belly from behind as he keeps kissing my neck all over.

I tilted my head to the side allowing him more access to my neck as he moves my hair away and kisses all over. He reaches up to my chin and turns my face to him.

I'm looking up over my right shoulder as he leans down and kisses me right on the lips. At first my eyes are wide open as I couldn't believe he just did that.

His whiskers tickle the sides of my mouth yet his lips are soft as he gently kisses me.

With his hand still holding my chin I feel his other hand caressing my smooth thigh and then his tongue forces it's way between my lips and we're really kissing now. I give in and close my eyes to this wonderful feeling.

Why is my body betraying me so much?! I kiss him back passionately and turn to face him putting my arms up resting my hands on his shoulders as our kiss deepens.

His hands are gripping my ass firmly as he pulls me closer and I feel his manhood on my belly. I feel so tiny in his arms yet so safe and comfortable. And I couldn't believe I'm kissing this man like I've never kissed anyone in my life. Our tongues twirling and dancing, intertwined in each other's mouth.

A soft moan escapes me as one of his hands lifts my skirt and goes between my ass cheeks.

He breaks our kiss and takes my hand leading me out of the room as I take little steps careful not to trip in these heels. He stops in the living room, thankfully it was empty so we weren't seen, just to grab a bottle of whiskey and then we go upstairs.

I'm still being led as he holds my hand leading the way down the hall and into a bedroom which is obviously the master bedroom. Once I'm inside he closes the door and locks it.

The bed is huge and I can't stop looking at it. There's a giant flat screen on the wall next to me, three very large dressers and a desk on one side.

He leads me over to the bed and we stand beside it as he opens the bottle and drinks from it then hands it to me. I take it with both hands and sip the strong whiskey.

He takes the bottle and sits it on the nightstand and pulls me back into his arms and our kiss resumes. I'm able to wrap my arms up over his shoulders now as we're so close and again I feel his cock on my belly.

Why did I want this more than anything I've ever wanted before? Why am I allowing him to feel me up like I really am a girl? All the racing thoughts in my head had me reeling.

I break our kiss, "I don't know what to do." I say quietly.

"Don't worry baby, I do. Just let your inner girl out and go with it."

I just nod looking up into his deep blue eyes.

We kiss again briefly before he turns me facing the bed so my back is once again to him.

His hands are on my shoulders and slowly slide down my arms until he reaches my hips.

I stay still as he reaches my butt and lifts my skirt.

"You have a beautiful ass, Christy."

"Really?"

"Yes baby." His hand runs over one cheek and down the back of my thigh, "and these legs, mmmm." His hand comes back up this time going between my cheeks up my crack causing my back to arch from the amazing sensation and chills.

Then he's down on one knee behind me! What is he doing? His hands hold my hips as he places gentle kisses on my butt, on the back of my thighs and the bare skin between hose and panties.

His hands run down my legs and it feels so sensual having those large hands run slowly up and down my legs and between my thighs.

I'm breathing harder as I feel his fingers reach between my legs near my hard little cock. They run over my dick and glide up my ass again to the waistband of the panties and before I knew it he pulled them halfway down my legs.

I gasp in surprise standing there half naked with him behind me.

The he started placing kisses on my ass cheeks all over. Another new amazing sensation ran all throughout my body.

"Ohhh," I moan a little.

I struggle with my balance and lean forward on the bed holding myself up with one hand.

What he did next shook me to the core. His hands spread my ass cheeks and he ran his tongue right up my crack causing me to really moan aloud.

His tongue ran right over my hole and I whimper as my ass wiggled a little wanting more.

"Oh yeah baby, you like your pussy eaten, don't you?"

I just continue to moan when his face went right back to my ass. I'm bent over the bed now breathing hard letting out little gasps of pleasure as his tongue twirls around my hole.

Then I let out a long "ohhhh" as his tongue goes inside me and it's more than I can take. My little cock twitches and begins to drip cum.

My breathing is rapid, my hand reaches back over his head as his assault on my ass gets even more intense.

I can't stop moaning as he kept this up for some time before stopping long enough to get something out of the nightstand drawer.

Then that wonderful tongue dove back in my ass again.

He stands up behind me as I'm bent over the bed and I'm about to stand too but he holds me in place.

I hear a snap of some kind and then feel a cool liquid being applied to my hole. His finger rubs it close to my hole and all around it before he pushes his finger inside me and I cry out in pain.

"Easy Christy, easy," he says soothingly, stopping momentarily.

The pain was searing hot but has subsided as he kept his finger still.

Then he pushes it in even further and my back arches, one leg quivers and I moan again in pain.

He leans over me with his finger still inside me and whispers in my ear, "I'm going to make you a lady now. But I have to warm your tight pussy up first since your a virgin."

I just nod gripping the beds comforter tightly.

"You want this Christy?"

Breathing hard I say without hesitation, "yes."

His finger is going in and out of me as I lay there listening to him whispering in my ear calling me 'sweet' and 'sexy' and 'little girl' telling me I have a nice tight pussy.

Then he slips another finger inside me and my leg bends up, my back arches again as the pain is back. He's slowly pushing in and out until at last the burn begins to subside. He has two fingers inside my ass and I'm reeling with lust.

While he's still leaning over me whispering to me his other hand comes up to my face gently caressing my cheek as if to soothe me.

With my mouth slightly open I take his hand with both of mine and begin to kiss and suck his index finger wishing it was his cock instead.

The woman in me is screaming to come out and she's really enjoying this!

"Oh that's hot baby and we will do that too but tonight, I'm taking your virginity."

He keeps sliding his fingers deep inside me and out stretching my hole preparing me for his rod.

When he finally removes his fingers my boy pussy misses them immediately. Then I feel the head of his cock at my hole followed by the gel being generously applied dripping down between my thighs.

He holds his shaft at my entrance then slowly pushes in gaping me as I moan even louder with this new bigger intrusion.

The burning pain has returned but not entirely too bad. He's taking his time pushing in me as the head keeps my anus spread wide.

I'm panting and moaning wishing he'd just fuck me now but he knows what he's doing. He pushes in a little more and my back arches and I let out a long soft moan.

He's slowly inching his way in spreading my ass wide. I'm in pain but I won't cry out. I grip the bed tightly and let out soft little moans.

I can feel his cock on the walls of my boy pussy, the bumps and ridges, the veins and that fat head as he slides in deeper and deeper.

"Are you all the way in?" I ask timidly.

"No baby, a little bit at a time." He says as he begins to pull out.

He repeats himself as he pushes in again then out each time filling my tight ass deeper.

He's holding my hips as he glides in and out pushing in further. With every thrust an 'uhh uhh' escapes me getting louder and louder.

He lifts my left left leg up onto the bed spreading my ass wider and starts sliding in and out faster. I'm holding onto the bed as I'm being rocked back and forth.

I'm panting as I moan feeling another orgasm about to happen. This is more than I can take and I think I'm taking his whole cock now and I'm loving it.

The sensations of first being filled with his cock is erotic especially when he hits a special spot deep inside me. It's when he hits that spot my ass responds by grinding back. Then as he pulls out it feels so delicious like a wonderful release and know he's going to slide it back in.

He's really breathing hard now and grunting a little as his hands grip my hips tighter. He's not crushing me but he is going deep with every thrust at a nice pace.

I feel his cock deep inside me begin to feel different, like it's pulsing causing me to have another orgasm. He's pushing in hard keeping his dick all the way in and it's still pulsing.

He's filling me with his cum! I can feel him shooting his load deep inside my boypussy and it's the most wonderful sensation yet!

He pushes in so hard he lifts me off the bed and holds it there fast.

I hear him catching his breath as I'm doing the same then that big cock begins to slide back out and I miss it as soon as he pulls out.

"C'mon baby, let's take a shower."