I Like Dressing Up

Printer-friendly version

Rachael looks at her collection of women clothing she has. Most of them she designed herself and have worn at one time or another. She has never confined herself to one gender. If she felt like dressing as a girl, she dresses as a girl. If she felt like dressing gender neutral, she dressed gender neutral. She loved designing and modeling clothes.

She looks at her reflection in the mirror to see how the newest cosmetic surgery she had was coming along. She was having her face changed to look like Renée Felice Smith. She was born on the same day the actress was, but two years later. She is as talented as her character on NCIS L.A. and stands an inch shorter than the actress herself does.

Her breasts were slowly coming in. She was taking estrogen pills and extremely strong doses of progestogens and androgens. So, far her breast hasn’t become too big yet. She wants the same size as her favorite person. She sweeps her long dark brown hair aside. Her hair and hazel eyes matched Renee Smiths.

She gets dressed in a pair of leggings and an oversized dark red t-shirt. She slips on the necklace a close friend gave her and her shoes. She was scheduled to work today. She grabs her purse, after checking her looks one more time and headed to work.

The used bookstore she worked at didn’t pay much, but it supplemented what she made doing custom tailor jobs for people. She had a client that was heavy into Star Trek and was part of a LARP group. She was supposed to come by sometime this week for her to make a costume for his members in the group. They were going to the Sci-Fi con coming in a few weeks. She had constructed a few costumes to sell. She had already paid to be a vendor there.

A few teenagers come into the store. They try to steal some books from the adult section, but Racheal stops them from walking out the door with the books. She watches the customers as they browse and when it comes time to close. She closes and counts the till for her register.

There was a gay and lesbian bar down from the bookstore called Star Shine. The owner named the place from the song Good Morning Starshine. She heads down there to get a drink and spend some time with a few friends of her. Tonight, they were having a Drag Queen contest.

Some of them she knew personally because she has constructed unique costumes for them. She walks in and heads towards the bar. She notices Beverly was working too.

“Hey sugar, watch you drinking tonight?” Beverly spotted Racheal as she walked up to the bar.

Racheal looks at the older woman and smiles. Beverly was a nice woman and was in a serious relationship with a cute black woman from
Florida. Her wife didn’t mind her flirting with the customers.

“Rum and coke please, Beverly.” Racheal takes a seat at the bar.

“Coming up.” Racheal glances around to see if there were anyone else she knew at the bar tonight.

“Here you go sugar.” Beverly sets the drink down in front of her.

“Thanks, Beverly.” She picks it up and takes a sip of it.

“Any time, sugar. So, what brings you in here tonight?” Beverly knew Racheal normally didn’t show up on a Thursday night.

“I’m bored. I have no projects to work on and I didn’t feel like going home alone. So, I thought I would come in to find someone to play with.” Racheal takes another sip of her drink.

“Well, good hunting.” Beverly goes to service another customer.

Beverly does come back to check on her to see if she wants a refill. She orders a refill and a plate of hot wings and potato logs. While she is eating and drinking, she watches the drag show. One performer catches her interest. There was a bright flash from an explosion and smoke covered the area.

A woman with long bright red hair steps out of it, singing the song that was playing. She was dancing to the music and using little stage magic tricks to enhance her performance. Racheal notices the crowd was glued to her as she sung and dance. Racheal has never seen anyone dance as well as she did.

When she was done, there was a loud applause as she disappeared, like she entered. The money that had been on the floor, was gone.

“Hey Beverly, who was that performer?” Racheal turns to look at Beverly.

“That was Blazed. She’s new to the drag community.” Beverly had heard rumors about a new up and coming drag queen that combine illusions
and magic tricks with her act.

“Well, I wouldn’t mind getting to know her.” Racheal was curious about her and wanted to meet her.

“She doesn’t stick around after she performs. The best time to catch her is before she performs or just after before she leaves.” Beverly knew several people who have tried to see her, but she was gone by the time she finishes her performance.

“I wonder why she leaves right away?” That got Racheal’s curiosity up.

Racheal has a few more drinks and ends up going home with a bear couple she knew. They didn’t care she was transgender. All they cared about was how good she was in bed. Plus, she has been their little girl off and on. She made sure they used rubbers when they took her.

She loved getting double teamed by them. She loved the length and size of Dwayne’s cock inside of her and when she switches up to be loved by his partner, Edward. He was as big as Dwayne. She falls asleep sandwich between them.

In the morning time, she wakes to the smell of freshly brewed coffee. She goes to the bathroom first to relieve her bladder and then stumbles into the kitchen.

“Morning sleepy head.” Dwayne and Edward spot their little girl walking into the kitchen.

Racheal just waves to them, while she walks over and brews herself a cup of coffee. She notices that Edward had made black walnut bread.
She cuts herself a slice and spread some honey butter on it.

“Mmmm, this is so good.” As Racheal takes another bite of the bread.

Her coffee was finish brewing. She adds three teaspoons of sugar and some cream.

“Didn’t you get enough cream last night, little girl?” Edward had a smirk on his face.

Racheal walks over to the table and sits on Dwayne’s knee. She looks at Edward “a girl can never get enough cream.” As she licks her lips and drinks her coffee.

Dwayne just laughs at her comment. He wraps his arm around her slim waist.

“Are you going to stay here and be our little girl today, or do you want us to drop you off at your place?”

“Mmmm, I think I can stay here and be your little girl today. I don’t have anything planned today.”

“After you finish breakfast, I want you to come to the playroom, so we can dress you properly.”

“Yes, daddy.” Racheal response back in her cutest baby voice.

Before Dwayne and Edward leave. They have sex with her and then dress her in a pink onesie while wearing a diaper and rubber pants. They make up several baby bottles for her to drink from during the day.

“Be a good girl till your daddies come home.” As Edward kisses her cheek before leaving.

“Bye, bye daddies.” Racheal waves to them as they leave.

Racheal watches them leave for work. She heads into the living room and pull a few Walt Disney movies out of their collections and watches them throughout the day. She had a blanket spread out on the floor, along with a pillow. Around noon time, she takes a few hours nap.

When she wakes up after a good four-hour nap. She takes her cell phone and sees if she can find out who this Blaze person is. She finds several pictures and video people had taken of her performance, but nothing saying who she really is. Which is very weird. She watches the
first video someone took of her and notices in the crowd, a person leaving at the same time as Blaze finished her performance.

She couldn’t get a facial shot of the person, but when she passed under some lights. She notices the person that left had long red hair. She wishes she could get a clearer image of her, but none of the video that had been taken.

She glances at the time and realizes that Dwayne will be home soon. A smile appears on her face as she waits, before peeing in her diaper. She knows he’s going to check her when he comes in.

She hates the squishy wet feeling of her diaper. She hears Dwayne’s motorcycle pulls up in the driveway. She hears the keys in the lock and
as the door open.

“Daddy!” As she rushes over towards him and hugs him.

Dwayne was surprised when Racheal yelled daddy and then when she tackled him. He looks down at her. She was a foot shorter then he was and eleven inches shorter than Edward.

“Were you a good girl today?” As he picks her up off the floor.

Racheal wraps her legs around his waist “I was a very good girl, daddy.”

Dwayne carries her to the playroom and checks her. He looks down at her cute face “it seems you had an accident.”

“Sorry, daddy.” Racheal giggles as she feels Dwayne clean her and put her back into a diaper.

Instead of putting her in a onesie, he puts her in a baby doll dress she made. He makes her wear the rubber pants and tights. Her hair was long enough that he could put her in pigtails.

“There, now you look a little older. What would you like for dinner?” Dwayne helps Racheal up off the bed.

“Mmmm, I don’t know. What does daddy want?” Racheal had no idea what she wanted for dinner.

Dwayne really didn’t feel like cooking. So, he pulls his cell phone out and call Edward and ask him to pick up some Chinese food. They already
knew what Racheal liked.

Racheal listened as Dwayne as Edward to pick-up Chinese food for them. She walks over to the fridge and grabs a baby bottle. She starts sucking on it. While they are waiting for Edward to come home. She watches as Dwayne changes out of his work clothes.

“Racheal, do you mind me asking you a personal question?” Dwayne looks at her.

“I don’t mind. What’s your question?” Racheal looks at Dwayne and wonders what he was going to ask her.

“Why do you act and dress like a woman?” Dwayne has known Racheal for a few years, but he never asked her this question before.

“Because I should have been born a girl, instead of a boy. I feel that mother nature made a mistake giving me a male’s body but feeling as a girl.” Racheal knew that’s all she ever wanted to be.

“If that is the case, why do you hang around with me and Edward and pretend to be our little girl?” Dwayne didn’t mind that she did, but he was curious.

“Well,” as she sits Indian style in the middle of the bed.

“First, you and Edward both have big cocks and I love how you guys feel inside of me. Secondly, the two of you are nice men and I enjoy
staying here with you. Thirdly, I know you guys like me being your little girl. I also know the two of you care for me.” Racheal gets up and kisses Dwayne.

Dwayne wraps his arms around her petite body “you know if you wanted to stay our little girl all the time. We wouldn’t mind it. If nothing else, we might be able to pay for your surgery.”

“But then, you will never have sex with me.” Racheal knew how most Bears were.

“That’s not true. Edward and I talked about it and we would still treat you like we always do. All we asked of you, is to stay as our little girl.” He places a fatherly kiss on her forehead.

“Can I think about it and can I keep my business?” Racheal has worked hard to establish a name for herself as a costume designer.

“Yes, you may think about it and you may keep your business as well. If nothing else, we can build you a workshop in the backyard.” Dwayne and Edward had 10 acres of land. At least 6 acres have been clear already.

“I’ll think about it.” Racheal gets off the bed and walks into the living room.

She had no problem living here with Dwayne and Edward. The two of them were nice men and would look after her. As for paying for her surgery, as much as she wants it. She didn’t want it to be something they could hold over her head or make them feel she only went along for the surgery.

She hears Edward pulling up next to Dwayne’s motorcycle. When he walks into the house. She noticed his hands were full.

“Hi, daddy.” She gets up and runs over and hug him.

“Hello, darling. Here, why don’t you take the food.” Edward hands the Chinese food to Racheal.

“Okay, daddy.” Racheal skips towards the dining room.

She sets the food out and grabs some plates from the kitchen along with silverware. Once the table was set. They sit down and eat dinner. The guys talk about work. All Racheal does is listens to their conversation.

She spends the night again with them. She lets them have their way with her. When the two of them have sex, she teases them. Soon, they drag her back into their sex acts. By one in the morning, she was passed out.

Edward wakes her up the next day and gives her a lift back to her studio apartment. There was a letter from her landlord, taped to her door. She grabs it and reads it when she enters her place.

The management company that ran the apartment building for the owner was increasing her rent by $80.00 dollars. She was barely making it as is. Her costume business was doing alright, but it didn’t leave her much money after she paid for the supplies.

She had put on one of the little girls dress she keeps over at Dwayne and Edwards place. Her client that was coming over for a fitting, was used to her wearing weird clothes. She had worn a pair of panties made for a little girl.

Noon Time:
Danny Wilson shows up at the address he had been given by the person who he ordered his outfit from. The building looked to be old, but the inside was clean. The person he was looking for, lived on the fourth floor. He heads up to the fourth floor and finds the apartment.

He knocks on the door and after a few minutes, it opens. Standing on the other side is a little girl dress in a light blue dress that was sort of short on her.

“Hi, I’m here to see Racheal Diaz. Is she around?” Danny had to admit, the young woman standing in front of him was cute.

She had shoulder length brown hair and her face looked like the actress who played Nell Jones on NCIS LA.

“I’m here. Please come in.” Racheal steps aside to let Danny walk in.

Racheal shuts the door behind her. She turns around to face her client. Racheal looks at the young man standing before her. She figures he must be in his mid-twenties and had sandy blonde hair. He stood a good foot or more over her. He had hazy eyes.

“What can I do for you?” Racheal just watches him.

“Well, I would like a custom dress made for me. I heard you are pretty good.” Danny had spoken with a few drag queens down at the club he worked at.

“Well let me get your measurements and we can look at a few examples of past dresses I have done so you can get an idea.” Racheal reaches for her tape measurer, but accidentally knock it to the floor.

When she bends down to pick it up. She accidentally flashes her panties at Danny.

Danny saw the little girl panties Racheal had on “cute panties.”

“Thanks, I like them.” Racheal knew she flashed Danny.

She knew her dress was short. She knew if she bends over, they would expose her panties. She designed the dress that way. So, when she wore diapers over at Dwayne’s and Edward’s place they could see she had them on.

“Take your clothes off please, so I can get your measurements.” Racheal looks for her pad.

Danny just does what Racheal says. When he is done, he stands there naked in the middle of her place.

“Okay, I’m ready.”

Racheal turns around to face him. He was nicely built “dam, you’re cute.” As she goes about measuring him.

“Thanks, but I’m not into girls.” As he feels Racheal measure his inseam.

“Who said I was a girl?” Racheal looks up at him as she measures his waist.

“You look and move like a girl.” Danny was watching Racheal.

“Actually, I’m transgender and I do want to be a girl.” Racheal writes the last measurement on her pad.

“Okay, you can get dress now.” Racheal takes one more look at Danny, before bringing up a few dresses she has done for past clients.

“Why would you want to be a girl?” Danny was confused. He was happy being gay and having a stiff cock occasionally.

“Because it’s how I feel inside. Just as you like having a stiff cock or get excited looking at a well-built guy. I feel mother nature played a rude trick on me. I like soft pretty clothing and dream of a man taking me like a woman should be taken. I hate having an ugly piece of flesh between my legs.” Racheal has always hated being a male.

She hated growing up and being told to be manlier and boys don’t play with dolls or wear dresses. She could recall how many times she had been punished for stealing her mother clothes and got caught wearing them.

“So, what’s with you dressing like a little girl then?” Danny wanted to know more about Racheal.

“I like wearing different outfits and there are two people I like that I am thinking about becoming their little girl.” Racheal has been thinking about accepting Dwayne and Edwards offer.

“So, do you see anything you like?” As Racheal show the pictures of dresses she has done in the past.

“Yea, you have several I would like.” Danny points them out to Racheal.

She makes notes on her legal pad of them. The ones he points out are some of her most expensive designs.

“If you had to choose just one, which one would you choose?” Racheal was curious which one he would choose.

“This one is the one I want. It’s exactly what I am looking for.” Danny loved the dress. It was classy and would show off his figure nicely.

“Ah! That one is at least six hundred dollars. I’ll need to do a few fittings to get it right on you and you’ll need to be in full drag for it.” The dress
was one that Racheal designed when she was in High school.

It had also been the one she designed to wear to the prom, but she never did. As soon as she turned 18yrs old. Her father tossed her out of the house and told her not to come back. She was lucky that her friend Suzanne took her in and let her stay with her, until she got the apartment she has now.

“It will take me about three weeks to make this dress for you. I’m also thinking about moving. I’ll try to get it done before I move.” Racheal looks around her place. She didn’t have much to pack.

“Are you moving far away?” Danny looks down at Racheal.

“Nope, the place I’m moving too is about fifteen minutes from here.” Racheal writes down some notes about the dress.

Danny looks at the dress “can I see what the dress would look like in a different color?”

“Sure.” Racheal brings up a program of hers and put the dress image in it and starts changing the color of it.

“That one. I want it in silver and a blue one as well.” Danny liked how both looked.

Racheal breathes in “now you're looking at $1,200.00 dollars.” Racheal looks at Danny.

“I’m good for it. I have another job besides doing drag.” Danny worked at Walmart in their electronics department.

“I’m going to need half up front in order to buy the material I need.” Racheal was going to have to special order the material.

She couldn’t buy what she needed from Joann fabric and craft supply or Walmart. Most of the stuff she needs for normal dresses she could get there, but not the material for the dress.

“No problem.” Danny pulls out six hundred dollars in cash and hands it to her.

Racheal writes a receipt for the money “here you go. I should have something by next week for you to try on.”

“See you next week then.” Danny turns to leave.

“I’ll be here.” Racheal escorts Danny out and walks back over to her work desk and order the material.

Racheal pulls her cell phone out and dials Dwayne’s number. She wonders if he is home or still at work.

“Hello Racheal, what can I do for you?” Dwayne was walking out to his motorcycle when his cell buzzed.

“Can you come and get me, daddy?” Racheal decided to use her little girl voice.

“Alright, I’ll be there in twenty minutes.” Dwayne figure with traffic it would take him that long.

“Okay, Daddy.” Racheal ends the call.

Racheal puts her hair back in pigtails. She doesn’t care if people see her little girl panties she has on. She packs an overnight bag and heads downstairs to wait for Dwayne.

Dwayne shows up and picks her up. When they get back to his place, she gets a piggy back ride from him.

“Dwayne, does your and Edward offer still stand?” As Racheal looks over his shoulder as he opens the door to the house.

“Yes, it still stands. Why what’s up?” He carries Racheal into the house.

“My landlord is raising my rent. As it stands now, I can barely cover my rent.” Racheal slides off Dwayne’s back onto the sofa.

“Well, like I said before. You are welcome to stay here as our full-time baby. You know there will be some conditions.” Dwayne and Edward talked about it.

“I know, you want me to dress as a little girl all the time and sometimes you’ll let me wear my little girl panties.” She lifts her dress up to show her little girl panties.

“Yes. That’s the deal.” Dwayne knew that was what Edward wanted as well.

“Okay, daddy.” She jumps up off the sofa and latches onto him, so he would have to support her butt.

One Month Later:
Racheal waddles out of the playroom. She was wearing her little girl swimsuit and was heading towards the backyard. Dwayne and Edward were throwing a party and all the men that were in the Bear club were at the house. She walks outside and over to Dwayne and Edward. They were in the pool.

“Come on Racheal, you can get in.” Edward held his arms out for her.

“Okay, daddy.” Racheal jumps out to him.

Racheal has been enjoying living with her friends.

He catches her. He holds onto her as they stand there in the pool. She didn’t mind wearing the swim diaper under her swimsuit.

“You put on the proper diaper, I see.” Edward felt the diaper under Racheal’s swimsuit.

Racheal looks at Edwards face “yes sir.”

Some of the other men in the Bear group look at Racheal. She was cute, and they knew she was trans.

“Too bad you want to be a girl, Racheal. It would be nice having a cub around.” George smiles at Racheal.

“I can’t help how I feel. I was never meant to be a boy. I have always known I should had been a girl.” Racheal knew the Bears could knew
understand what it meant to her.

“Well, I hope one day you get what you want.” George goes to enjoy the water game that just started.

183 users have voted.
If you liked this post, you can leave a comment and/or a kudos! Click the "Thumbs Up!" button above to leave a Kudos


Am I weird for finding Racheal's situation so appealing?

laika's picture

Some stories I wish I could comment on anonymously, because I'm going to wind up sharing stuff about myself that's nobody's bizness; but if I sent this as a PM i'd feel like a coward... and that would be worse for my self esteem than a bit of embarrassment over outing myself as the weird bitch most folks here know I am anyway...

I love the age regression aspect and the idea of sharing a bed and a life with these two Daddies who would be gay for each other yet essentially hetero for me. I'm glad that while this story gave a pretty clear idea of what their threesomely sex life was like, it didn't turn into some tediously explicit porn story. (The diaper stuff didn't totally wreck the story for me---a reader can't reasonably expect a story to conform 100% to her own likes and dislikes---but I have an aversion to that kind of thing, and even in fantasy want to be at least old enough to not have to put up with soiling myself...)

I also like the friends Racheal meets along the way in this, her town supporting a vibrant LGBT community; and that it sounds like she's going to be able to balance her age regresion role-play relationship with the more adult side of her personality, and her artistic and business pursuits.
~hugs, Veronica (that weird mermaid chick)