The feminine crossdresser

Chucky open’s his eyes as he awakes, looking around at his familiar surroundings in his bedroom. Band posters, comic books and video games all over the floor.

His parents always gave him crap about the things he liked and tell him the typical “you’re too old to be into thoses kinda things!” He didn’t care though. He stepped out of his bed in his black t-shirt and grey track pant’s that he wear’s to bed and walks over to the window to look out as he yawned and stretch out his arms.

Look’s like the first day of spring break would be a beautiful day, though he could care less because As far as he was concerned he had a date with his PS4 today!

Among other things…. He was definitely a weird kid as far as his parents were concerned, couldn’t disagree with them though….leaving his room and heading down the hall to his sister’s room who had left for college and would be spending her break in Miami. She left a lot of clothes behind…..Oh did he mention…he likes to dress up like a girl..

He smile’s as he opened his sister Amy’s closet, she owned so many clothes that it would have been impossible to take them all with her to college. Her loss his gain as far as he was concerned, his sister was pretty small as was he as well. She was 5″7 117 lbs, had larger B cup breasts and a bit of a bubble butt.

He hadn’t had a growth spurt since middle school. He was 5″6 about 120 lbs maybe so her and he were about the same size…butt included… Chucky had a rather large bubble butt for a guy and my hips were a little wide for some reason. He pulls out a black tank top and then reach down to a little dresser that was also in the closet. Pulling out a cute pair of his sisters denim short short’s.

Dressing like a girl was pretty easy for him not only because his sister and himself
were damn near the same size (including butt size) but because he had shoulder length blonde hair and feminine features and also kept his legs shaved because he loved the way they felt and always wore pants around other people so no one would notice.

Sliding the black t-shirt off and putting the black tank top on. Looking down at his flat chest in the B cup bra and frowning “wish I would have been blessed with your boobs too some times Amy” laughing a little to himself, trying not to be too loud because he had to listen and make sure that one of his buzzkill parents didn’t come home for a lunch break.

Sliding his track pants off and open’s the top dresser drawer, this was where Amy kept her bras and panties. Shuffling through the colorful assortment of panties. Some dull, some slutty, clearly I’m going for a slutty pair! He laughed to himself as he pulled out a red lace pair of panties and slide them up his legs and up to his butt. They are a size too small and the bottom of my cheeks stick out a bit. His soft small penis up front is pushed upward a bit but it’s not uncomfortable, having a small penis came in hand for his…let’s call it a hobby

Sitting down on his sister’s bed in her tank top and panties, remembering the first time he’d ever put on her clothing, Chucky was young the first time and not even in high school yet and here he was now at 18 still doing it.
Always envied that his sister was able to wear such cute outfits and I started looking at other girls as well. The more rvealing clothes that girls wore tight, something about them that just turned me on….but not by them wearing it no….I wondered what it felt like to feel sexy and to be wanted by men like these females knew.

Remembering watching porn years ago and seeing a young sexy female getting pounded by a stud with a huge cock….most guys would wish they were the guy. Not him though, he wished he was the girl! But he was too chicken shit to ever try being with a man, especially dressed as a female…scared of the criticism that he’d no doubt recieve…

He’s brought back to reality when he hear’s his phone ringing from my room down the hall. Quickly sit’s up in the tank top and red lace panties and speed walks down the hallway upstairs to his bedroom. Seeing his dad’s name on my screen and swipe my thumb across the screen to answer ” hey dad what’s up?” Imet by his dad’s angry voice that he has always had ” Chucky I need you to stick around the house for a few hours” he should have already known that Chucky had no intentions of leaving the houe. Rolling his eyes ” sure dad but why? Chucky twirls his long hair in his finger ( he even acted like a girl when he was dressed!) ” your uncle Laughing Ferret is coming by to drop off some papers for me so just let him in and grab them”. He get’s a little angry because he would have to put normal clothes back on ” yeah sure dad no problem” they both said goodbye and hung up.

The two of them had never had much of a relationship, his dad always gave him crap about being different, never having a girlfriend, not having many friends and being more interested in comics, music, anime and comics. Oh if only you really knew what I liked dad, he laughs to himself and walks back to Amy’s room and outs the tank top and panties away as he puts his pajamas back on. He sighs as he closes his sisters bedroom door behind him.

About a half an hour passes and Chucky is nose deep in a Batman comic when he hears the doorbell ring. He quickly stands up and head’s downstairs, the tile floor leading to the front door is cold to his barefeet as he walks faster. Opening the door to the big smiling Uncle Laughing Ferret, ” what’s up kid?” as he steps in ” hey not shit Uncle Laughing Ferret just enjoying the peace and quiet”.

Laughing Ferret smiles and walks into the kitchen where he puts a stack of paers down, he wasn’t really Chucky’s uncle but he grew up always seeing him because of his dad and Laughing Ferret being such good friends. The big man smiles again ” oh I bet, must be nice not having the buzzkill parents around for a bit” he smiles. Chucky’s dad and Laughing Ferret were starting their own auto garage and were finalizing the deal, the paperwork he left on the counter no doubt would seal the deal.

The two talk for a bit, Chucky always enjoyed talking to Laughing Ferret, he was a gentle giant probably close to 6″6 thick beard and short brown hair and in pretty damn good shape for 50. Chucky hated to admit it but he thought Laughing Ferret was pretty hot….” well kid I won’t keep you anymore”. Looking at the tall man, feeling sorry for him, he lost his wife a few years back and his kids were all grown up and moved out. Only having Chucky’s father to speak to had to suck! Walking Laughing Ferret over to the door ” hey no worries Uncle Laughing Ferret you can come hang any time you want. They both smile at each other as he leaves.

Watching him through the window as he hops into his big red F150 and leaves. A big smile across Chucky’s face now as he darts up the stairs back to his sisters room. Practically dancing as he goes to the closet ” fuck it im going big today!” Opening the closet and grabbing a red dress that his sister wore to impress a guy she liked. It was tight on her and just barely covered her ass….smiling to himself ” let’s see if I can pull it off”

Grabbing a cute pair of red apple bottom heels that Amy had bought to match the dress, reaches for the red lace panties again….”naa” grabs a black and red thong instead and a red bra that he would stuff the best he could. Stripping down to fully nude as he pulls the thong up and put’s the much too big bra on first, then slides the dress on that clings tightly to his skin, his smooth shaved legs looking good, the bottom of the dress just like when his sister wore it was just barely covering his ass.

Walks over to a small vanity table in his sisters room and decides it’s a nail painting and makeup kind of day. He grabs a bottle of red fingernail polish to match the dress and heels and shakes it, he had gotten really good at doing his nails over the years. The only thing that sucked was that he had to immediately remove the polish. Doing his toes first, he only wore a size 8 in mens and had pretty small feet, after finishing his ties he starrs on his fingernails and waves his hands back and fourth for them to dry after finishing. Then sits down and takes a deep breath as he begin’s to put on eyeliner….mascara and a nice shade of darker red lipstick.

The final touch…he straightens his hair up real nice and straight with his sister’s old hair straightener. Smiling at himself in the mirror….he could pass for a female easily with makeup on he felt. He stands up and puts the heels on, he’s probably about 5″9 now with them on. He leaves his sisters room and starts heading back to his. Heel’s clicking on the wood floor as he does, he could probably walk in heels better than most women could at this point of his life!

Grabbing his phone and pushing his fingers through his soft long blonde hair as he walks over to a big mirror on his wall where he’ll be able to take full body self shots. It was his favorite thing to do dressed up, he had a folder on his laptop full of them. Taking sexy pics was good for boosting his confidence up.

He smiles as he stands sideways with a hand on his hip, sticking his butt out a little and snaps the first pic of what he can only describe as the best he’s ever looked. Chucky had checked out at this point….he had become someone else…someone that he always referred to as… “Sadi”. Takes a few more sideway pics before walking over to his dresser and grabbing a kleenex box and he starts shoving them down into his bra.

Trying his best to make it look like he had bust, from a sideway view it was pretty convincing. He walks over to the mirror and pulls his hair back as he makes a duck face and snaps a few more pics….he must have forgot to lock the front door after Laughing Ferret left… “hey i forgot to leave these with the rest of the….uhhhh cody?”

The voice….he feels his world end as he turns and see’s the tall man standing in his door way in disbelief. Chucky takes a step back ” I…..Laughing Ferret…” The big man steps in and look’s Chucky up and down, Chucky likes the way Laughing Ferret is looking at him but knows that the jig is up…he was going to now be known as a freak. Laughing Ferret finally speaks up ” how long has this been going on for…?” Shame on his face as he responds ” It’s been going on for a while Laughing Ferret… looking down but then looks up when he feels the footsteps approaching him and see’s that Laughing Ferret is now in front of him.

Even in heels Laughing Ferret still hulked over him, ” you wouldn’ want anyone to find out about this would ya….?” No please Laughing Ferret! I’ll do anything! Laughing Ferret starts to rub up and down Chucky’s hips ” anything huh?” then he leans down and plants a soft kiss on his lips….Chuckys first kiss awkwardly Chucky kisses back and they continue to kiss, mixing their tongues in as they do Chucky reaching up and putting his hands on Laughing Ferrets chest area. He feels big hands squeeze his butt a little as the dress lifts a bit in the back.

The kiss breaks as Laughing Ferret keeps squeezing ” mmmmm now how did you end up with a butt like that kid!? Mmmmm bend over the dresser and let me get a good look at it!” Chucky blushes but does as he is told and puts his hands on top of his dresser and bends over a bit. He feels the big hand on his ass again and then feels a smack followed by a squeeze he hates to admit it but he is loving this.

Another smack ” goddamn Chucky you have a nicer ass than most girls do!” Chucky smiles and looks back ” th….thank you” he get’s his ass fondled a little big longer before Laughing Ferret backs off ” come undo my belt for me sweety” Chucky smiles from being called sweety….this is it…he has wanted to feel like a girl forever and now he finally was and he felt wanted! He really feels wanted after he see’s how hard he has made Laughing Ferret….slowly undoing his belt and unzipping his pants. The pant’s drop around his ankles and Chucky gasps.

It had to have been 10 inches long atleast! THe big man backs up and sits down at the edge of the bed. Stroking his python slowly ” get on all fours and crawl to me cutie” Smiling and biting his lower lip at being called cutie he does as he is told and gets down on his knees, the wood floor hurts his knees as he crawls over to Laughing Ferret, trying to look as sexy as possible.

He finally reaches inbetween his legs and rubs the mans thighs as he looks at the cock mesmerized. Laughing Ferret smiles and softly smacks the big cock on his face “whatchya thinking about Chucky?” Chucky doesn’t like that he was called by his name and frowns. He then tries to sound as femine as possible ” it’s Sadi….and i’m thinking about sucking this big cock..” Laughing Ferret’s eyes get big and wide…”ooohhhh fuck….nice to meet you Sadi….but a little less talk and more sucking” he winks.

Finally the truly born Sadi persona takes the large cock in both hands and strokes it softly to Laughing Ferrets approval. This was it…..leaning upwards a little he takes his tongue and runs it up and down the shaft. Oooooooooh Sadi….he moans as she continues to lick and then finally the moment of truth she takes the head of his penis into her mouth and starts to suck him “ooooohhhhhh good girl….yeah suck that dick baby” She has never felt so alive. Only able to get about 4 inches of the large cock into her mouth, she continues to suck him, siwrling her tongue around his shaft as it’s in her mouth.

This goes on for about five more minutes before he stops her ” that was great baby but I don’t wanna blow my load just yet….I have better plans… get up her on the bed on all fours and spread your legs Sadi” she does as she is told and stands up, feeling relieved not to have her knees on the hard wooden floor now.

Getting on the edge of the bed on all fours, his erect cock that was not maybe 5 inches was sticking the side of the the thong up front, he had never been so turned on before. Laughing Ferret kicks his boots off and then his pants completley off, then steps up and slides the dress up a little bit revealing Sadi’s nice bubble butt.

He begins to smack it again and squeeze it before taking a step back ” fuck….you don’t mind if I snap a few pictures for later do you?” She looks back and smiles ” you didn’t even have to ask Laughing Ferret” A big smile on his face now as he pulls out his HTC and takes some pics of her ass, stroking his cock as he does.

He had taken enough for a nice fap sessions later apparently because the next thing she knows the thong is being pushed over a bit and her cheeks spread as she feels a tongue enter her hole. Grabbing the sheets tightly “OH MY FUCKING GOD! Holy shit yessss eat my ass Laughing Ferret!” She didn’t know such sensation existed, she is sad when he stops and stands back up.

Laughing Ferret spits in his hand and rubs it on his dick…stroking it slowly ” ready to get your cherry popped Sadi girl?” Looking back a little nervous but she doesnt think she could ever tell this man no. Smiling ” mhm….I want you to be my first Laughing Ferret….I trust you..” He smiles and grabs her ass cheek with one hand and starts to slowly push his head into her tight hole “oooohhhhh…..” her mouth wide open as she begins to feel pain instantly.

The head has barely even went in ” fuck…..god you’re huge!” Laughing Ferret has her hips tightly now as he has about 3 inches in.

Getting to about 6 inches now he can see that she may not be able to completly take him in as there is really no more room in her anus for him to push. He starts to slide in and out slowly, she softly moans and breathes heavy as he keeps going in and out of her tight hole.

Sweat trickles down his forehead as he softly pumps into her. She wishes that she could take more in but it was painful enough with the 6 inches in. Her eyes closed and face sideways on the bed she continues to softly moan and breathe heavy. Her eyes still closed as she bites her lip ” oooh fuck me Laughing Ferret! Don’t stop!

He pulls out and Sadi looks back kinda sad ” what’d wrong? He smiles and leans down kissing her lower back ” lay on your back for me Sadi so I can see your pretty face ” she smiles and quickly turns over onto her back and slides up the bed a little more so he can get on the bed with her.

He get’ s in between her legs and lays his massive frame against her much smaller frame. Planting a kiss on her as she grabs his face and passionately returns the favor. She felt so safe and wanted by the mature man as she shared a passionate kiss with him.

He breaks the kiss and gets up on his knees lifting her legs up as he does and grabbing the back of her thighs as he pushes them down to her chest area ” I need to be inside of you again sweety. The large head of his cock back at her hole, this time however it slides right in.

Grabbing the sheets tightly with her red painted nails ” oooohhhhh Laughing Ferret fuck me faster please…” he does as he’s asked and picks up speed. Still not quite taking him fully in but then he slows down and looks at her. Looking back at him when suddenly ” Ughhhhhh nook fuck Laughing Ferret it’s too big!

Laughing Ferret quickly slid his full 10 inches in and was holding a wild look on his face from pleasure. He slides in and out at full length ” oooooohhhh my fucking god! Fuck my tight ass ooooooohhhhhh!” He pumps with a little more force and is met with a loud moan of pleasure. Her tiny semi erect cock moving back and fourth each time he thrusts.

He pulls out again “whew! Ok sweety get back on all fours” she quickly flips back over to all fours and he grabs her hips tightly. This time though he doesn’t hold back. Her ass jiggles as he pumps into her fast and wild now. Her little penis swaying around wildly as he fucks her. Jerking her head back as her hair goes back.

His hand reaches to her throat and turns her head back as he slides his tongue into her mouth. Sadi’s eyes practically in the back of her head now ” oooooohhh Laughing Ferret yesssss fuck me hard!” She moans ad their tongues explore one another. He let’s go of her throat and grabs her hips extremely tight her head jerks back down and she smiles and giggles, he pumps into her fast and hard.

She enjoys his large hands tightly grabbing her hips however though as he continues to wildly pump into her for another 10 minutes before finally ” god….im gonna cum baby” she feels the cock slide out of her and he squeees her ass as he strokes quickly with his hand.

Letting out a big grunt as Sadi feels his hot seed land all over her ass. Laughing Ferret breathes heavy as he finishes and then lays down on the bed next to her, she rests her head on his chest and they begin to softly kiss each other for a few minutes before she breaks the kiss ” you’re not going to tell on me are you…?”

He looks at her and smiles ” no i’m not going to I promise…..but can we maybe do this more…?” Looking up at him and smiling ” I’d love too” he kisses her forehead and stands up. grabbing his pants up off the floor and sliding them back on. Sadi sits up and ironically enough pulls some tissue out of her bra to clean the cum up on her backside.

Laughing Ferret laughs ” if you just had a pair of breasts no one would ever think you’re a boy….god i’m looking at you now and don’t even recognize you….you look amazing Co…I mean Sadi” He winks and smiles and she smiles back at him ” wanna walk me out?” Sadi gets up and straightens the dress out and extends her tiny hand to him with a smile as the big man extends his and tightly grabs a hold of hers.

They reach the front door and he puts his hands on her hips and gives her a kiss, his beard tickles her a little bit each time he does ” you know…..I’m totally not doing anything tomorrow night…just planned on sitting at home and watching movies. Maybe you could lie to your parents and say you’re going over to a friends house for the night….you could come over and dress up for the entire night!” She smiles at the idea ” I would love that….let’s do that.” she smiles.

They give each other one more goodbye kiss before Laughing Ferret leaves. He closes the door behind him and smiles, lookinbg forward to tomorrow night as he realizes that it’s time to go back to being boring Chucky since his parents would be home soon. But smiles again at the thought of spending the night at Laughing Ferrets house tomorrow! Life was going to start changing for the better he felt!

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