tagTransgender & CrossdressersHer Crewcut and Masculinization

Her Crewcut and Masculinization


It had to stop. She was spending far too much money on her hair with frosting and tints. The bill for her nails was ridiculous. It was as if she picked the most expensive place in town. And lingerie! For what she spent, we could have bought an entire Victoria's Secret. It was always spend spend spend, yet, she never once lifted a pretty finger to even try to get a job of her own.

She came home from shopping one day and I greeted her with a frosty stare. She shrugged her shoulders and headed to our bedroom. I followed behind her as she entered the bedroom and found all the credit card bills placed on the bed along with a garbage bag filled with all of her panties and bras and makeup. She rushed over to her chest of drawers and pulled them open only to find nothing but men's tighty-whites and beaters. No bras -- no panties! Next to her new men's underwear -- She found a silicone cock, a packer to place in her new tighty-whities. Next, she flung open the closet door and found only men's shirts and jeans

Then she sees me standing at the door. She started yelling about her missing clothes, but I calmly assert THAT these are her clothes. She says that they are men's clothes, and I counter, well -- she isn't a man -- but she is a boy -- a cute twinky cock sucking twinky boy. I order her to get out of those sissy clothes she has on because she is going for a hair cut -- the most boyish hair cut I get for her. She starts for the door and I push her on the bed as I pull her clothes off and forcibly begin to pull a pair of men's underwear up her legs. I order her to stuff the fake cock down into her new boy's underwear. Then I hand her an ace bandage to wrap around her chest to flatten and bind her tits.

Pushing her to her knees, I drop my jeans and pull my cock out of the side of my jockstrap. As I run my hand through my crew cut I tell her that she get her a crew cut just like this. I order her to pull her cock out through the fly of her briefs and stroke it like a man as she sucks me off. As she sucks I tell her "You wish you had a cock just like mine, don't you, twink!"

I spurt cum all over her face, and then smear it with my hand, ruining her makeup completely. I then hand her the tightest pair of jeans in the closet to show off her bulge. Slapping her ass, I order her to get ready -- we have a haircut appointment at a barbershop in the gay part of town.

As we drove to the barbershop, I see her place her hand on the bulge in her jeans, as if she still doesn't believe that she has a cock between her legs. We pulled up at a barbershop. She stepped out onto the sidewalk and sees her reflection in the windows of the shop. The bulge in her jeans must have seemed conspicuously huge, because she moved her hand to cover it, as if in shame for walking around with a hard on. Several crew cut, leather clad men stood around near the entrance, and their eyes seem to burn right through her.

I lean over and whisper to her "I bet a fag boy like you would love to have one of those leather pigs stuff his cock in your ass." She feels her anal sphincter spasm, but doesn't answer.

"Answer me, boy," I demand,

She whimper out a 'Yes"

"Yes what" I bark --- "From now on, her will refer to me as SIR"

"Yes, Sir" she answers.

"That doesn't sound convincing" I remark. "Maybe I should tell them that you need a good ass fucking after your hair cut"

I push you toward them. "Tell them, boy!"

"I should get a good ass fuck after my haircut"

The two leather men laugh -- "We'll wait here!"

I push her into the barbershop.

"Joe -- my son's been acting like a sissy girl. I need you to get rid of this mop and give him a proper fag haircut"

Joe smiles a wicked smile and pushes her into the chair. "C'mon boy"

Joe pulls the blinds shut and flips his sign to 'CLOSED"

He snaps the cloth cape and it cracks like lightening bolt, as she feels sweat roll down her neck. She feels a wetness develop between her legs. As Joe fastens it, he reaches to pull the cape around front. He grabs her cock and gives it a squeeze.

"He's not very big. Are her sure he's not a girl?" he says before laughing a fiendish laugh.

Joe clicks on the Wahl electric trimmers and the whirr sound feels the air. Then when she didn't expect it, she feel the cold steel against the back of her neck and hears the buzz as that pixie cut fades into a crew cut with each upward swipe. One, two, three swipes. With each one she feels a tension mounting inside her. Her clit asserts itself against her fake cock and her pussy lips swell as the she seeks some sort of sexual release.

"Yeah -- like that" I say. "Nothing on the back and sides and no more than a 1/3 inch on top."

Zip zip the hair goes falling her shudder with each buzz.

Joe reaches for the mirror and I stop him -- "Wait! Little fag's been shaving her legs and underarms too I think she needs to know how a real man shaves"

Joe snorts a laugh and touches her cheeks. "Yeah, lets lather her up"

He places a wet towel on her face and then uses a brush and mug to whip up some shave cream. Taking the towel away, he spreads it on her cheeks and neck with the brush. As she sits there, she hears the slap slap sound as Joe sharpens the straight razor on the belt. The she feels the razor on her cheek.

She can't take it any more, and covertly unzips the fly of her jeans. Her hand enters the zippered opening and she feels for her fake cock. She swears it feels erect like a real cock. She swears that she can feel the sensation of her balls tightening with every stroke of the blade on her face.

Just as Joe goes to shave the back of her neck he nods to me to look and notice what he thinks she is doing. He makes the last stroke and then grabs the cape and flings it off with one hand, leaving her sitting there with her cock in her hand.

We both howl with laughter -- "fag boy got turned on my his hair cut. Didn't he?" I ask as I run my fingers through her new crew cut hairstyle.

"Yes, sir," she answers

I nod to Joe and point to the backroom. "What do you think, Joe, should we make her pay for her new haircut?"

Joe nods in agreement.

"Well, boy? Get ready to pay for you crew cut"

"Yes Sir" she answers

I grab her by the arm, but Joe stops me. He grabs her shirt and undoes it. He then pushes her down in the barber chair, and yanks off her running shoes before I undo her belt and pull down her pants.

"Stand up " I order "Show us what you got."

She stands up and sees herself in mirror -- totally changed from feminine to masculine. She sees herself in tube socks, tighty whitey briefs with a cock bulge, the tip of which is poking out of the fly, and a white beater undershirt covering her flat chest, flattened by the ace bandage compressing her tits.

Joe pushes her to the back room. A dirty cum stained mattress is in the middle of the room. I push down her on it and then Joe and I slip down to our jockstraps.

We kneel down next her and pull our dicks out of the side of the pouch of our jockstraps. They hover just inches above her face.

"Do you want a jockstrap like Joe and me?" I ask.

"Yes, sir" she replies in fear

"Then beg for it as you stroke your cock" Joe demands.

"Yes, Sir! I want to wear a jockstrap just like you" she replies.

"Why do you want to wear a jockstrap?" I ask.

"Because I'm a cock sucking fag boy. Sir" she replies.

Both Joe and I stick our hard cocks in her mouth. I hold up her crew cut head with my hand, and caress its bristles.

"Jack that cock, fag boy, as you suck us off" Joe demands.

I pull out of her mouth and Joe straddles her face as he stuffs his dick deep past her lips. I move down between her legs and grab her hand. I place it on my cock and start her jacking me off as I begin stroking her fake dick.

"You like that, boy?" I ask.

I can just barely make out saying "Yes, sir" as Joe fucks her face.

Just as Joe's cum splashes against the back of her throat, I cum and it goes flying all over her fake cock. Joe rolls to one side and laughs.

"It looks like fag boy came" he jokes

"Yeah. -- Here fag boy, taste your cum" I bark as I scoop some of the cum off the fake cock with her fingers and thrust them into her mouth.

As I get up I toss I towel at her-- "clean this mess up" I yell, "The leather pigs are waiting for ass"

As she finishes wiping the cum off her chest and stomach, there's a knock to the door of the backroom at Joe's. It was the leather men.

"He's all yours, guys," I said as I motioned toward her.

They both grunted as they eyed her up.

One of the leather men walk up to her and run his hand over the bristles of her crew cut

"It'll do," he said emotionlessly.

The other one tosses a jockstrap at her. It lands on the floor at her feet. "Put it on" he barks.

The first leather man grabs at her tighty-whities and pulls them down. Her fake cock drops to the floor and bounces like a rubber ball.

"Fuck -- is he small! No wonder he needed that" the leather man laughs.

As they both strip down to their jockstraps, she pulls her jockstrap up her legs. The leather men help her adjust and she sees her reflection in the mirror as she stands next to them, flat across her crotch -- a bulge in theirs:

One of leather men pushes her down on a trunk on the floor in the backroom. She ends up on all fours like a dog.

The other leather man comes around to the front of her. He pulls his cock out the side of the pouch and stuffs it into her mouth.

"Suck that cock you crew cut fag boy!" he orders as he rubs her head.

Just as she begins to suck she feels the tongue of the other leather man running along her inner leg. His smooth shaved head slips along her inner thigh and then he rubs it hard against her pussy through the pouch of her jockstrap. She feels her clit begin to swell. It's never felt like that before -- she could swear it was a cock. Then in one quick move he stuffs his dick in her ass.

She can't take it anymore and she put her hand in side her jockstrap. Her clit feels enormous. She can actually take it between her thumb and forefinger and stroke it!

"Stroke that cock. Fag boy", the leather men order.

An aroma of her aftershave mixed with sweat and cum fills the air as they pound her at both ends. Beads of sweat trickle along the short coarse hair of her crew cut.

She feels the leather men start to cum, pumping their jism into her. Just then it happens -- ejaculate spurts out of her pussy and drenches the pouch of her jockstrap.

As she collapses, she knows inside what she wants -- she wants a big cock-like clit -- she wants her head shaved like the leather man who reamed her ass. -- she wants a flat muscular male chest. Can this be her future?

Report Story

byTrapper_Jock_Mcintyre© 5 comments/ 40410 views/ 10 favorites
1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartep274308, langdofx and 8 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (5 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (5)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: