Caught in the Act

Caught in the Act

By Jessica C

Home Alone sick from school, Jeff thought it was safe to get into his sister's stuff...
Rachel home early catches Jeff in her clothes and makeup...
Instead of being angry, Rachel helps her young brother to look better as a girl...
Getting caught can sometimes be the best thing that could happen.


I was twelve and would be thirteen come Friday; I was home sick from school. After getting lunch I was bored so I went into my sister’s room checking out her stuff. This is not the first time; I not only like her clothes, but I am fascinated with girls makeup. I intended just to put on one of her blouses, but I didn’t like how I looked just wearing the blouse. I wanted enough to imagine I was a girl. I was soon wearing a pair of her panties, a cute skirt as well as under the blouse I now had on one of her bras. Each step led me a step further. I tried making up my face, but I got carried away there as well. My eyelashes were heavy with mascara and my eyes with eye shadow; I went heavy on the foundation and makeup thinking it was more realistic.

I took great pains to cover my tracks as my sister would probably be very upset if she caught me.

It was 1:30 when I heard a sound like the back door opening. It couldn't be, no one should be home until after 3:00 p.m. My brother 15 and Rachel my sister 17 are at school; dad’s on a three-day trip and mom works until after five, closer to six. I panicked as I heard someone in the house. I tried to race upstairs to my room, but I’m too late. I run past Rachel’s room into the downstairs bathroom. I hurry to close the door, but something blocks the door before I can get it fully closed.

“What are you running for,” its Rachel’s voice?

“Nothing Sis, you just scared me,” I say. I’m still trying to get the door closed.

Sis relaxes, “So quit pushing the door closed and come out. Mom wanted me to check on you when I got home, and before I focus on my college class.” I forgot she has classes at the community college, as part of her high school schedule.

“I’m okay Rachel, just leave me alone. I need to go to the bathroom.”

Rachel says, “I doubt that very much, what are you hiding? Did you get into something you weren’t supposed to?” There seems to be a change in her voice like she might have realized something. “Jeffie, what have you gotten into?

“Nothing,” I yell, “just leave me alone and don’t call me Jeffie!” I am afraid as my sister, almost five years older, is stronger. I push hard but I can’t get the door closed and locked.

Rachel says, “You know you aren’t going to get the door closed on me. If you were into my stuff or something I would disapprove, don't make it worse. You better give up and let me know sooner than later, Jeffie.”

“Sis please leave me alone.” I lie, “It’s nothing, I’m sick; I just want to be left alone. Please, pretty please!”

“Jeff, you need to open the door. I can smell my makeup. You’re not the first, your brother did it four years ago.” I’m surprised by what she said and I relax enough that she forces the opening of the door a little more. She says, “Let the door open if it gets damaged by you trying to force it closed you will be in bigger trouble with Dad!”

I fall back from the door and cuddle into a ball on the floor; I’m ashamed that my sister is going to see me looking like a sissy. She has reached down to take my hand. I can tell she not terribly angry or forcing me up. She says, “I’d rather you weren’t wearing that blouse but please get up and let me see you.”

I look between my fingers covering my face and see Rachel. She’s smirking but she’s neither very happy nor terribly angry. “Please, take your hands away from your face, I already know you're wearing my makeup. I just want to see how well you did.”

She takes a hand, helping me to stand. I’m quickly saying, “I’m sorry, I’m sorry.”

She cuts me off, “Are you sorry that I caught you or sorry you need help in looking more like a cute girl?” I was surprised by what she said and must have stood there staring with my mouth open. "Overdone, but not too bad for a girly-boy."

“I’m not a girl; I don’t want to be a sissy,” I say forcefully!

She says, “Your brother wasn’t either, but he did want to see what he would look like in my stuff. Mom and I helped him once; that was all he needed.”

I tell her, “You’re lying to me, Johnny wouldn’t do that he’s too tough.”

She said, “And you’re no sissy either, but I bet I could make you into a cute looking girl if you give me the chance.”

I respond to her, “But you said you need to go to the college.”

She said, “I only need to send in an assignment, the college is going on a mid-semester break. I can do that on my computer.


Please sit down so I can help remove the makeup to redo your face. Boys always seem to use too much makeup. You must think more makeup is somehow more girly.” She smiles as she has a cloth she uses for taking makeup off. She smiles as she works on my face.

She hands me a washcloth and a cleansing bar, “Go wash your face and dab it with a towel to get the extra moisture off once it's clean.” She hands me a face towel. “Let’s go in my room and close the door.” I am soon sitting on a chair in front of her vanity. She has me turn away from the mirror.

She shows me, “This is a small dab of concealer to help with some blemishes and this is a foundation to help give a uniform complexion.” I am not sure why she is explaining it, but I’m paying attention. “This is the basic makeup, I’m going with light makeup. I think it works with you almost being a teenager and your dark hair and eyes. Oouu that's nice.” She works with my eyes only for a short time. “I’m just using a light amount of pink eye-shadow and just enough mascara on the wand to separate your eyelashes.” I am mesmerized looking into Rachel's face as helps me. Boy, she's pretty.

She asks me, “Please unbutton that blouse and take it off, I have another that goes better with that skirt. ...You might not like hearing this but you have pretty legs, little brother.”

Without thinking I say, “Thanks.” I guess it is a natural reaction to receiving a compliment.

I can tell Rachel is pleased with what she is doing. “Now pout your lips,” I can see the lip gloss is pearl pink. “Let it set a moment,” she says. “A light brush of blush to each cheek.” She then picks up a brush and brushes my hair in different directions. “That helps, now just sit there a moment and don’t peak. I need to do one more thing.” There always seems to be one more thing.

She is quickly back. She places a towel over my shoulders and begins holding a piece of ice on my left earlobe. I speak up, “No, you can’t do that!”

She calmly says, “You know there is usually a consequence for misbehaving, piercing your ears and earrings are it.”

I quip back, “You got to make me up to look like a girl that's enough?”

She smiles and says, “I consider that a treat for you.” Without any more delay, she tells me to hold a hand out and puts in my palm a set of earrings. They do look pretty. She takes away the ice cube and pokes the ear. “Ouch.” One earring is in and the back is quickly in place. She has me hold the ice cube to my right ear. “Please don’t Sis, what will Mom say?”

She smiles, waits and then says, “That's long enough, take your hand down.”

Another poke, “ouch” and the earring is on. Rachel stands me up and turns me to the mirror. It is what I never expected to see but what I had the dream about numerous times. There was a teenage girl standing in front of my sister. A half head shorter than Rachel, not quite as pretty but a pretty enough girl who could be Rachel's sister.

Rachel asks me, “So do you see the pretty girl I do, or do you see some sissy?”

I had to admit, “She could be your younger sister. Not as pretty but prettier than I could ever have hoped for.” Oops, I said too much. “I guess I should say thanks and double thanks for not getting mad with me?”

Sis says, “Sit and let’s see if we can get you into a pair of pantyhose before I let you try a pair of my shoes to complete the look.”

“I don’t want to!”

She says, “I think that's a lie, plus it is not a suggestion, sit!” She rolls up each leg of the pantyhose and starts by getting my toes and feet lined up properly. She is up over my knees when she asks me to stand and she guides them the rest of the way up and then drops the skirt back around them.

She has a pair of blue flats that she has me put on. “Now go walk once around the house on this floor and enjoy,” I grumble to cover up how good I feel, but I do as she says. Walking back into her room I hear the command to smile. I do and there's a click.

I say, “You better not have taken a picture, did you? Hurry and delete it.”

“I am not sending it to anyone, except Mom,” she says. “I am pretty sure I know what her reaction will be. I don’t want her to be surprised and angry with me when she gets home.” Rachel quickly writes her text and has it sent. Five minutes later she gets another message. Truth is my sister gets more messages than I can keep track of.

I finally say, “I need to change and take this makeup off?”

Rachel says, “Mom just responded to my text. You are to stay dressed up until she is home and sees you. She doesn’t want you acting up or she says you’ll be in bigger trouble.”

“Bigger trouble, haven’t I been punished enough?”

Sis says, “Why don’t you sit and read a book or get your tablet and play some games.” I get my tablet and I’m ready to sit down as Sis giggles, “You swept your skirt under you like a good girl as you sat. I'm impressed, you must have practiced that before.”

The second time, I was up and I was checking myself in the mirror. I was not mindful of doing it. Rachel asks, “You’re impressed with how nice you look aren’t you?”

“I’m not sure impressed is right; I guess I’m surprised you did everything so well for a girl. I'm not a girl!”


Sis asks, “What would you think of going to the movies with me and my friend Tiffany this weekend to see Cinderella? I would do it as my gift for your birthday.”

I say, “I don’t think Tiffany wants to go to a movie with you and your little brother.”

Rachel says, “Tiffany could bring her younger sister who is about your age.”

“I’d think her sister would think it strange you brought your brother to see Cinderella.”

“That’s why you should go as my sister and she’d never had to know.”

I stand up and place my hands on my hips, “You don’t think I’d actually consider that?”

She says, “After you thought about it, yes, I think you might be tempted and decide to go. I think since you wanted to see if you could look like a girl. Now you’d like to pass for a normal girl and do something with other girls accepting you. Going at night and being in a movie theater would make it easier for you to pass as my sister. I think that it would be fun having people see you as a girl.”


I didn’t say anything, instead, I just sit down and pick up one of her magazines. Seeing the clock, I ask Rachel, “What am I to do when Rob gets home from school?”

She says, “I suggest you stay in my room. I’ll handle Rob. He will probably be in and out, he’s usually doing something after school.”

Rachel took time to talk to me about the universities and what she's interested in studying. Then she was showing me fashions on the internet and pulling out samples of her clothes from her closet. It was crazy that she thought I would be interested. It was crazier because I found myself following all she said.

Suddenly, there was a knock at her bedroom door and Rob poked his head in. “Sis, do you know where Jeff is? ...Oh, I didn’t know you had a friend with you. ...I picked up two of his assignments from school.” ...Before we could stop him, Rob was further into the room and he could see the both of us.

“Déjà vu,” he lightly laughed, “I think, I’ve been in that chair, but I didn’t look that good.” I was quickly embarrassed and about to cry.

Rachel spoke up with some authority, “Rob, you get out of my room and don’t cause any trouble!”

“Cool it,” Rob said, “I didn’t hassle my little brother. I’m guessing you caught him and did as you did to me that time. I’m surprised and I’m not.” Rob thought and then said, “Does this change what you want for your birthday bro?” He laughed and left the room.

Nervously, I went back to playing a video game on my tablet, while Rachel changed and showered. I didn’t see her without her clothes but I realized she was now a more mature woman. I didn’t think anything inappropriate, except the annoying new thoughts that I wouldn’t mind looking like her. She teased me, “Would you like to look more like your sister now that you know it can be fun? You know you make a cute girl. You like it, don't you?”

I walked out to the kitchen to get a snack when Rob came down from our rooms upstairs. “Hey bro’ what should I call you? It is too upsetting to call you Jeffie when you are looking so pretty.”

Without thinking, I said, “Rachel called me, Jessie.” Having caught myself, I wanted to hurry out of the room, but Rob blocked my exit.

“Don’t go getting all upset or I will tease you. You might as well relax and enjoy it. You probably won’t ever do this again. I say enjoy it.” He got something out to drink and then said, “I hope Rachel didn’t show you pictures of me; I know she and Mom have some. I looked okay dressed up, but you look like a real girl. If I hadn’t been looking for you; I’m not sure I would have recognized you.”

Rob nudged me toward the nook and we both sat down for a visit. I was nervous. Rob said, “You might not believe this, but my time dressed up has helped me in relating to girls. ...And no, Cyndi doesn’t know nor do I want her too. But she and other girls seem to like the fact that I appreciate how they look and kind of understand it takes an effort. They think it’s just because we have a big sister.”

He continued, “Did Rach stare at you intently and smile as she helped you with your makeup? I’ll never forget her doing that to me. Since you’re still dressed, I guess she’s making you wait until Mom sees you. The idea is scarier than the reality. You’re lucky Dad isn’t home tonight. You are older than I was, I suspect he would tease you even more.”

I said, “Dad got angry at you; how did he punish you?”

Rob says, “I said, he would probably tease you. If you lie or do something stupid he can come down hard. Dad is better than a lot of dad’s. If you decided you wanted to do this more, he might not be happy. Even then, I don’t see our Dad losing it or getting mean with you.”

Rachel had come into the kitchen area and had been standing nearby. She asked, “Rob are you staying around and having dinner with us or going someplace?”

He said, “Things got canceled for tonight so I’m home, I guess.”

Rachel asked Rob, “Scoot over or get out, I need to do someone’s fingernails.” Rob scooted over and Rachel sat across from me and started to do my fingernails.

I pleaded, “Please don’t polish my fingernails, I don’t want to look any more like a girl than I already do.”

Rachel said, “Somehow I don’t believe that. You allowed me to begin after all. I think you are still worried each time we do a little more, what someone might say. Actually, you will be better off looking more like Jessie and not showing Jeff at all."


“Mom said, "If Rob’s home for dinner we’re going out to eat.” Rachel saw me turn scared. “Relax Jessie, Mom will fix your hair and quickly no one will see Jeff. Mom said, 'We’ll go over to Highland Park, so no one will have a chance to recognize you.'”

I wanted to get up and run to my room, tare off the clothes and cry. Rachel said I needed to be still as she polished my nails. And then I had to wait for them to dry.

The worse part was after she was done and my nails were dry. I got up and walked around. I needed to go to the bathroom. I had to wait another ten anxious minutes to make sure my nails were really dry.

Rachel stood outside the bathroom instructing me, step by step, how a good girl uses the toilet, “Bring down your hose and panty, make sure the skirt is not in the way. …Sit don’t try standing. Make sure you wipe yourself properly even in front. You don’t want drips running down your pantyhose. …Make sure you do not tuck your skirt into your pantyhose when you get up and then come back out.” When I was finished Rachel came back into the bathroom to make sure my clothes looked proper. and that I cleaned myself, making sure I dried my hands and checked my makeup and hair.

Rachel made me use the mascara brush to spread my eyelashes and handed me the lip gloss to redo my lips. She handed me a small purse to use, ‘yeh and yuck’. Part of me secretly liked the idea, but I was afraid to show it. Part of Jeff was definitely uncomfortable, after all, I’m really a boy. Rachel was very pleased and said so, “You did very well Jessie, you should be proud of yourself.”

It was another hour before Mom was home; hearing her car drive up, sent shivers up and down my spine. Rachael and Rob stood with me, interested in what Mom’s reaction would be. Mom already had a slight smile, but it soon brightened as she saw me. “Rachel said, you make a pretty girl. I did not expect you to look so naturally pretty. Come here please and turn around slowly so I can see all of you.”

Rachel said, “Mom, she already had to go use the toilet. I kind of instructed her from the other side of the door, but she did everything herself. She even checked and fixed her makeup.”

Mom said, “Are you telling me she did all of her makeup and hair?”

I looked down and spoke, “No, Rachel caught me after I had gotten into her stuff after I had tried doing it myself. I think I looked more like a poorly made up streetwalker from what Rachel said.” Mom looked to Rachel who shook her head ‘yes.’

Rachel said, “I came home early from school, to do my college coursework. I surprised Jeffie. He ran to the bathroom to lock himself in and undo everything. But I got there before he could fully close the door and lock it. It’s nice being the big Sis and catching my brothers.”

“After I transformed Jeff into Jessie,” I could see my Mom amused by the name change. "I intended to keep Jessie a secret from Rob. But Rob came searching for Jeff to give him his classwork assignments from school. He knocked on my door and poked his head in and before I could stop him or Jessie could hide.”

Mom said to me, “Well young lady, I think it was meant for you to become visible today.” Mom wasn’t completely composed, but she was better than I imagined. “You can follow me to my room and we’ll have a little talk.”

Mom looked to Rob, “So did it bring back good old memories? Are you jealous of how Jeff looks so much like a girl? He could be your younger sister. This morning he looked more like you. Now he looks like a younger version of your sister.” My Mom took my hand ready to walk away.

Rob said, “Yeah, I was ready to hassle him and then I thought the better of it. He’s about two years older from when I got caught. He’s lucky he hasn’t started to change, he makes a prettier girl this way.”


Mom took me to her room and had me sit on the bed. She grabbed a change of outfits and went into the master bathroom. She took a quick shower and changed there. Once dressed and as she was ready to do her makeup and hair she called me into the bathroom to sit and talk with her.

“Sit up young lady; when you are dressed as such I want you to try to present yourself as a young woman. After I fix your hair and add a few things, there will be no signs of Jeff. If you behave well, you will be safe in public. People will only see... Jessie, is it?”

Whenever Mom looked at me I lowered my gaze until she lifted my head. “If I am comfortable with you dressed and looking as you do; I would appreciate it if you would look at me when we talk. …Do you hear me, young lady?” I looked up and said yes, but she waited for me to smile.

I watched my Mom do her makeup and realized how beautiful she still was and how well she did her makeup. “Usually, I would just retouch my makeup but since we're going out I, I'll do it for evening wear.” I noticed it was more colorful than usual. I observed how little makeup it took for her to achieve the look she wanted. I was actually proud that my Mom made herself look so attractive while letting me watch.

Mom asked me to put out my left-hand palm up; when I did she touched me lightly with a drop of perfume onto my wrist. “Rub it with your other wrist and then lightly touch it your neck below your ears.”

I tell her, “I don’t want to smell all yucky like a girl.”

Mom said, “Yucky, I find that hard to believe. You tried on your own to look like a girl. Then let your sister pretty you up. You’ve been sitting with me paying close attention to whatever I do. I will apologize if you want, but I wouldn't want anyone smelling a boy under that beautiful veneer.” I thought and rubbed both areas with my wrist while saying, “Thanks, Mom.”

“Now stand in front of the mirror and watch the changes I make.” She feathered my hair making it look more delicate, spreading the curls across the top and sides. She had two barrettes that she put in my hair; one to hold hair she swept across my face and then brushed back. I liked the look as I noticed Jeff was gone. I smile and Mom asked, “Does that mean, you approve how Jesse looks or that Jeff is gone?”

I didn’t want to admit anything but Mom waited me out, “Yes both, if we’re going out I am glad Jeff isn’t showing. I’m also surprised you and Rachel have me looking like such a pretty girl. It is embarrassing, I don’t want to be a sissy, but I admit I like how I look.”

“Relax it with throwing around the label of 'sissy'. Girls aren’t sissies and a boy wanting to look like a girl probably has a strong sense of character. It is just different from most boys. You will probably go back to being totally boy like Rob. But you should learn to be patient. You wouldn’t want your own prejudice coming back on you.”

Jeff asked, “What do you mean ‘probably’ go back to being totally a boy? You don’t think, I want to be a girl like Rachel, do you?”

Mom looked at me, thought and then said, “Well, you’re not a boy in the same sense of your brother being more physical and bigger built yet. Nor are you a girl like your sister, nor do I think you’d ever be totally a girl? Truthfully, maybe I shouldn’t say it. I wouldn’t be surprised that today means more to you than what it meant for Rob.”

Mom looked at the clock, “Let’s talk about this later if you want. We should be going to dinner. I want to stop somewhere on the way back.” Mom searched through some jewelry. “Here let me put this necklace around your neck. Here is a bracelet that goes with it and a pinkie ring adds a nice touch. I put on the bracelet and then look at it in the mirror and the ring on my pinkie finger.

“You quickly picked and coordinated that with how I already looked. Thanks, Mom, does that kind of stuff just come normal for girls? ”

“Your sister said, you didn’t look too bad when she found you. You just made the boy mistakes of too much and the outfit was close but not quite right. You’re a pretty neat person, others can help you learn if you’d just ask.”

I joked, “What was I to come out and say? Mom, I want to look like a girl? Could you help me pick the right outfit and help with my makeup?”

Mom pulled me in for a hug, “I suspect that would be hard, but I want you to know you can approach me even when the questions and thoughts aren’t easy. I’ll do what I can to make that question not so hard.” I wasn’t sure what that meant and I didn’t ask. We were now with Rob and Rachel going to the car.


Rob joked, “Why don’t the two sisters ride in the back and I’ll ride up front and help navigate.”

Rachel was playing some of her music, first Mom joined in and then I did, but I try doing so as Jesse. I have sung to myself before as a girl and liked it. I was barely whispering as I sang along or so I thought. Rachel cheerfully said, “Jesse, you have a beautiful voice. Sing out, girl.”

Dinner would have been better if Mom didn’t draw attention to us. She asked the waitress, “Is it too early for my daughter to be recognized for her thirteenth birthday?” That led to people singing along to ‘Happy Birthday’. It allowed Rachel’s friend Tiffany know we were there.

Tiffany came over to say hello with her younger sister in tow. Everyone was introduced. Susan, Tiffany’s sister, thought Rob was cute and noticeably flirted with him. It was when, they were ready to return to their table that Tiffany asked, “So are the four of us going with us to see Cinderella Saturday night? Susan is hoping to go but she won’t go if Jesse doesn’t.”

Rachel turned to me, “It’s Jesse’s decision and she hasn’t decided.” Susan leaned down not quite in my face but gave me her puppy eyes and a cute girly pout.

“That’s not fair, how can I say ‘No’ with her looking like that.”

Susan asked, “So that is a yes?”

“Yes, if it will make you happy.” I looked to Mom to see what she thought. I couldn't tell. I kind of hoped she would rescue me.

Susan gave me a hug and bounced as she went back to their seats. I wasn’t sure if this was a setup, though Rachel swore she did not know that Tiffany and Susan would be there.

I moaned, “Mom, I really don’t want to go. I don’t think I can do this again.”

Rob spoke up, “I think in five years you’ll look back at this as one of your best times in growing up dude. I understand being nervous but look at it this way. You’re going to have a girl moment that few boys will ever have. In ten years, if you tell people what happened they’ll tell you, you’re lying unless you have pictures. Even then, they won’t believe it.”

It was on our way home after dinner, Mom insisted we stop at the mall. She pulled me into a women’s shop insisting, “Jesse, you need to get a cute outfit to wear. You shouldn’t be wearing Rachel’s clothes. And this way if you decided to dress up again you’ll have something of your own to wear. If it comes through the laundry; I will know to return it to your closet.”

Rachel asks, “Do you want a mini-dress or a skirt and blouse outfit?”

I hastily and vehemently said, “No mini-dress!” I was hard to please as some outfits kind of yelled ‘My Mom dressed me’ and others were too revealing or too loud for me. Either way, I didn’t want to stick out.

I feel silly getting a dress, but since I’m getting one. It might as well be something I like and I think is attractive. Mom challenges Rachel and me to quickly choose two dresses or outfits for me. Rachel picked out an off-white handkerchief skirt with a print top, and a dress she insisted was not a mini-dress and Mom agreed.

I found a ruffled blue skirt that was shorter in the front and longer in the back with a shirt that had bold lines of blue, yellow and red going diagonally down over a white background. My second choice was a fitted flare skirt with a colorful print and a colorful blouse. All my skirts and tops were pretty alone, but together didn’t quite work. Instead of putting both outfits back, Rachel found the high-low ruffled skirt in red and it went well with the blouse I chose. She found an attractive peasant blouse with a yellow chemise to wear under it.

I liked the dress but was uncomfortable in saying so. The saleswoman said, “If you get the red ruffled skirt and blouse I would approve of selling you the dress for 40% off.” Mom and Rachel were kind of happy with the offer. I was still embarrassed as they also purchased for me several pairs of panties and a new padded training bra.

I would be glad when the day was over and I got back to being Jeff. It did, however, take added work to take off the makeup and get my hair back to my style. I laid in bed enjoying the memories of the day before falling asleep…

To be continue…

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