He showed me my inner sissy

Thoughts and pictures from a sissy

[cherigurlmn]

The Big Day

Daddy sent me to a salon one morning.  He dropped me off outside and told me to ask for Ginger.  When I walked in, I nervously repeated what Daddy made me memorize.  I looked at the pretty woman would be taking care of me for the entire day, knowing that she and Daddy were friends and I had to get it right.  I looked at her near tears from panic, and I said  “Mister Sampson showed me who I really am inside.  Can you please help me look like the pretty girl I need to be?”

Ginger smiled at me.  She touched my hair, already shoulder length and said  “You are already a pretty girl, but I can make you even prettier. But I want to hear you ask me again.  This time with more confidence.”

Inside I was totally panicked because there was no way I could say it louder without other people in the salon hearing it, but I knew that’s what she wanted. I looked at her with pleading eyes and she just nodded.  I said with a louder voice “Mister Sampson showed me who I really am inside." 

She held up a hand and asked me  “And who are you inside?”

I started to stammer, but I calmed myself a little and said  “I’m a pretty girl inside.”

She smiled and asked loudly  “Mister Sampson turned you from a boy to a girl, or were you already a girl?”

Near tears, I answered  “I was already a girl, but I didn’t know it.  Can you please help me?”

Ginger hugged me and said  “Of course I can, princess.  Follow me.”

I glanced over my shoulder and two women were giggling and smiling at me.  One of them said  “I can’t wait to see the results!”  I tried to smile back, and then I turned and followed Ginger.

That day, I got my hair done with highlights, a manicure and pedicure, and a full body wax.  Thankfully I never had much body hair to start with.  The girls were all very kind to me, and kept coming by to tell me I was looking better and better.

Finally, my fingernails and toenails were painted a pretty pink, and two women spent almost two hours going over makeup tips with me.  At the end of the day, Ginger called Daddy and told him I was ready.  I went outside and waited for him, and we finally went home.  Daddy asked me to go to my bedroom and change into a pretty dress.  

When I came upstairs, he had me stand in front of a full length mirror he placed in the middle of the living room and had me look into it.   He asked me “Well, how do you feel?  I imagine that experience made you feel a little transformed.”

I said  “Yes, it did feel like I was really transforming. I feel...very girly.”

He told me to look at the mirror again and say exactly what I was feeling into the mirror.  And I better not hold back.

I looked into the mirror and said  “I feel like I am looking at the real me for the first time. I feel like a girl.”

Daddy smiled and unzipped his pants, pulling out his cock.  “And you look like the real you for the first time, princess.  Come tell me how grateful you are, and then show me.”

I went over to him and knelt down between his legs.  I looked up into his eyes and said “Thank you for helping me feel pretty.  Thank you for making me your girl, Daddy.”

[cherigurlmn]

The First Argument

Daddy handed me some cash and a credit card, and told me to go get some pretty new things.  I smiled, but I was nervous.  This would be my first time out on my own since I became fully femme.  

He looked at me and said “Do NOT buy anything that could be seen as masculine.  No sneakers that aren’t pink.  Nothing male.”  

I nodded and headed to the mall, feeling really...OBVIOUS.  Like, everyone in the world knew I was a boy in girl clothes.  No one said anything that I could hear, but I was freaking out on the inside.  My voice lessons were still pretty new but I talked almost at a whisper, and it seemed to work out.

When I got home, I unpacked my bags, and Daddy instantly didn’t like the jeans I bought.  He even pointed at the tag, showing that they were male jeans.  I argued that no one would know if I wore them with heels and a cute top.  He opened my closet and asked me if I could find anything else that looked even remotely male... and I couldn’t.

He made me put on a very short skirt, and higher heels than I usually walked around in.  He handed me the car keys and told me I was going to return them right now.  I nodded and before I could turn around, he said  “And take off your panties.  Right now.  Leave them on the floor.”

I tried to stop the tears as I complied with him.  He drove me back to the mall, and I tottered into the returns area.  I leaned against the counter when I was returning the jeans, worried that my cock would be visible.   I finished up and Daddy called me.  He said he drove home,  and I was told to go wait at another entrance to the mall.

I walked all the way to the other end of the mall, and a police car pulled up next to me.  The window rolled down and I saw one of Daddy’s friends smiling at me.  He waved me over and told me to hop in.  I thanked him for the ride and he just smiled.   About two blocks from the house, he pulled the car over under some trees and smiled at me one more time.  He reached down and unzipped his pants and said with a smile “I think you know what John promised me for giving you a ride home.”

I nodded and leaned over.  He came in my mouth in only a few minutes, then drove me home and dropped me off.  I went inside the house and Daddy smiled at me, then asked  “You aren’t going to make that mistake again, are you?”  I shook my head and he said  “Because you are ...?”

I looked at him and said  “Because I’m your sissy girl, Daddy.  And I only wear girly clothes.”  He nodded and said  “Next time, you’re going to have to suck your way home from a carload of my friends if you need to be reminded you’re a girl.”

[cherigurlmn]

A Night To Be Tested

Daddy John handed me a cute little dress and the shiny black patent leather Mary Jane heels I had owned since the first day he told me he threw out my boy clothing and told me this was what I had to wear now.

He said  “We are going out tonight with some friends.  You will call me Uncle John around them since several of them have no idea you are my little sissy.”  I got dressed and packed a purse full of girly things then we went to a club.

Daddy got me in the club by telling the door man that I was his niece, and he had me sit at the end of the booth with my legs crossed so everyone could see me sitting pretty in my heels and dress.  

As the night wore on, one of his business friends named Dan that was visiting kept looking at me and smiling.  I shyly smiled back but I was terrified at messing up and not being the best girl possible.  Finally, his friend said he was tired and was going to call a cab back to his hotel.  John said he would be happy to drive him to the hotel and we all piled into John’s car.  Dan looked at me in the backseat, winked,  and told John he sure did have a pretty niece.

John took a deep breath and said thank you but then asked if he could tell Dan a secret.  Dan said sure, and John took another breath and said  “She’s very pretty, but she gets in trouble.  That’s why she is visiting me.  Her mom caught her sucking men off for $20.”

Dan’s eyes got very wide and I turned bright red.  John laughed and said  “I’m the cool uncle.  I don’t judge.  And I told her she should charge $50.”  Dan laughed and John said “She told me she loves doing it, but the men started offering money and she just took it.”

Dan laughed  “So it’s $50 now, huh?”  John laughed with him and said “Yep. Well, $40 for close friends.”  i blushed and looked at the floor.  John said  “Hey Cheri, why don’t you walk Dan up to his room and see if you can make forty bucks.” I looked up in shock and he nodded  “Go on.”  I got out of the car and I heard Dan ask if he was serious.   John replied  “If you want it to be.  I can park here for about 15 minutes.”

Dan chuckled and got out of the car.   I felt his hand gently take mine, and we went into his hotel.  We rode the elevator in silence, and I followed him to his hotel room.  He closed the door as we entered, and said  “I can’t believe I’m doing this, but I’m drunk and you’re hot.”  He reached into his wallet and pulled out to twenty dollar bills, and I felt them get pushed into my purse.  He took my hand and led me to a chair that he sat down in.

I knelt in front of him as he unbuckled his pants, then I reached out and sucked him to completion in around three minutes.  He thanked me and I went back to the car.  John told me  “Good girl.” and we went home.

[cherigurlmn]

Makeup Now and Always

The second day after I admitted that Daddy was right and I’m a sissy, he handed me a pair of pink heels and a pink bikini, then told me to go out back and tan by the pool until he called me in.

I never really had much hair anyway, but it felt so strange rubbing tanning lotion on my totally smooth body.  And wearing nothing but the bikini, even knowing there weren’t any close neighbors...it made me extremely anxious and nervous.

About 3 hours later, I was sitting in some shade drinking water and relaxing when Daddy came outside.  He told me that my surprise was almost done and there was just some clean up to do.  With a smile, he told me that for my last hour while he cleaned up, he only wanted me to wear the bikini top and the heels to remove some tan lines.

Finally, a bit more than an hour later, he came and told me I could come inside.  I walked in the house and we went downstairs.  In my bedroom, against the wall by the bathroom there was now a pink and white vanity with lights around the mirror.  I didn’t know what to say, so I looked at him with a confused look.

He smiled and said  “It’s your makeup vanity.”  He saw the look on my face and smiled, then said  “Because you're going to wear makeup from now on.”  He looked my in eyes and said  “Girls have vanities full of makeup.  And you’re a girl now, whether you accept it right now or not.”  He waved toward the vanity and had me sit down.

I sat slowly and he showed me drawers full of makeup, nail polish, perfume, hair ties , ribbons, and so on.  He said he got advice from some female friends of his, and he stocked me up, but I could organize it any way I wanted to.  As I sat there quietly, he took my face gently in his hands and said  “You are a girl, and girls wear makeup.”  I nodded and he said  “I want to hear you say it.”

Three times, he made me say  “I am a girl and I wear makeup.  This is who I am now.”  By the third time, he pointed out that my cock had been totally erect by the second time I said it openly, so he knew I liked the gift.

[cherigurlmn]

The Sleep Over

My first Daddy, John was a big strong man.  He was easily a foot taller than me, and 100lbs heavier.  He could pick me up without breaking a sweart.  Very rarely in the six years I lived with him did Daddy ever threaten me with anything physical.  The first time was the night he told me I was either going to suck my first cock (his) that night, or he would hold me down and make me do it...one way or another, it was going in my mouth.

One of the other times this happened, he came to me in my bedroom on a Thursday evening.  He sat down and told me that I was going away for a weekend.  One of his female friends had talked to him about her deepest fantasy of having a slutty teenage cheerleader daughter just to see what it was like, and John told her that I would do it for her because he said I would.

Daddy looked at me very sternly and said  “You are going to be her daughter all weekend.  You are just coming home for the weekend from cheerleader camp.  You are staying with your mom just after your boyfriend broke up with you, and you really need some girl time . You will never once break character.  If I find out that you did, I’m going to punish you severely, where it leaves marks and makes you cry for a week every time you sit down.  This is very important to her and I expect you to do your absolute best.”  

With that, he handed me a cheerleader’s outfit and told me to put it on.  We went to the park near the house, and he took pics of me in the costume, then made me email my “mom” pics from camp and ask if I could come home for the weekend since Tommy broke up with me.  She emailed back within five minutes, and told me to have the Uber driver drop me off at the house.

Friday afternoon, Daddy dropped me off with a final warning to be totally and 100% girl, and I went to the door.  I didn’t have to knock because she opened it and waved at Daddy as he drove away.  I said “Hi mom, thanks for letting me come home this weekend.”  With a smile, she let me in the house.  She looked at me and asked if I was OK... I could tell she was asking if I was OK playing her daughter like this, but I replied  “ As good as I can be after Tommy broke up with me, mom.”  She couldn’t hide her smile as she leaned over and gave me a hug.  Daddy was right... she really wanted this fantasy to be perfect.  I was nervous, but determined to do my best for her.

For the next two days, I never felt so much like a girl as I did that weekend.  We went shopping and she bought me a cute dress and heels.  We traded makeup tips, shopped more, went to dinner, and went dancing at a club she liked.  She introduced me as her daughter, and not a single guy we talked to had any clue I wasn’t really her daughter.

Saturday night after the club, we even hung out with two guys for a bit and made out.  She gave them her number and promised we would meet again when I was back in town.  Then we went home and talked about boys and dressed in pretty lingerie and watched porn with hot young guys and giggled about how big some of their cocks were, and if we liked the taste of cum, and how it felt when a man danced close and you could feel it through his pants that he was hard.

At the end of the weekend, she was braiding my hair for me, then she smiled down at me and leaned over.  She hugged me and said I was truly the best daughter ever, and asked if I would do it again.  I smiled and meant ever word when I said  “Any time you want, mom!”

I did it three more times with her, once for a whole week while Daddy was out of town on business, and I adored it completely.

[cherigurlmn]

Even Walking Takes Practice

Once my boy clothes were thrown away, Daddy not only gave me girl clothes, he gave me girl shoes.

One pair of flats.  8 pair of heels.  I remember looking at the heels, then back to Daddy John and not even knowing what to ask.  He smiled and told me “You'll get the hang of them, I promise.”

By the second week, I could stand in them decently, and I could wobble on them as I walked around the house.  One sunny morning, he told me to get on a miniskirt, and sexy top in addition to thigh highs and heels.  I got dressed as he instructed, and presented myself to him.

He asked me if I knew where the mailbox was.  I nodded and said  “Out at the main road.”  He nodded and smiled.  “Good. Get some practice walking in those new shoes.  Go get the mail.”  

My eyes went wide, and I asked “Like THIS?”  He shook his head and said  “No.  Turn around.”  I turned around and he pushed me over the couch.  I felt his hands reach up under the already tiny skirt and I felt the panties being yanked off.   He backed away and smiled, grabbing my arm and leading me out of the front door..  “Much better.  Go get the mail.”

I turned around and he stood in the doorway.  “Go practice walking in your heels.  Shut your sissy mouth.  If you ask me one more question, the skirt comes off too.  Call me when you get to the mailbox.”  Then he shut the door. 

I turned with tears in my eyes, and shaking legs...then started walking down the long drive to the mailbox.  I tried my best to walk casually in the heels, but it was much tougher since I was also worrying about anyone seeing me.  I finally made it, and I called John.  He told me I was a good girl and deserved some rest.  Then he told me to go across the street and sit on a bench in the little neighborhood park, and further instructions would follow soon.

I sat there tying to keep my legs crossed for 20 minutes before a friend of his picked me up and gave me a ride back to the house.

[cherigurlmn]

Prom Prep for Girls

Once Daddy set me up to go to prom with a boy, I realized just how much girls have to do for prom.  I spent an entire day in a spa getting my nails, hair, brows and body waxing done.  And half the day of prom getting my hair done.  

Even before that, there was the dress.  Daddy took me to a store to buy a dress, and immediately told the woman that even though I was a boy, he wanted me to be the prettiest girl possible.  I know she thought it was funny that I was being fitted for a dress, but Daddy paid in cash for the dress and matching heels.

With two solid weeks of daily training with my voice coach to get it as feminine as possible. Sure, I totally missed my own prom because of my shyness, but I never imagined anything like this would happen.   I still had trouble wrapping my head around going to prom as a girl with a football player.   But Daddy borrowed his letterman jacket and made me wear it around the house.   He would say things like  “My little girl got herself a football star boyfriend.  I’m so proud.”

Two of Daddy’s female friends came over and helped me get ready to be a girl in front of other girls.  By prom night, I almost felt like all the ‘boy’ in me was barely there anymore.  When I told Daddy, he smiled and said “Good.  Because you were never a boy anyway.”

[cherigurlmn]

Old Coworker

Daddy told me he wanted me to quit my job and live full time as a girl with him.  I really didn’t want to totally lose my male side and asked if I could just do it part time.

He nodded and said he would think about it.  The next day he came home from work and handed me a new dress and heels.  I put them on for him as he watched and took pictures while I dressed and put on makeup.  When he liked what he saw, he had me kneel in front of the mirror and give him head for just a few minutes.

When I was done, he said that work was all taken care of for me. I asked him how, and he told me he talked to the assistant manager and one of the guys I worked with.  He got their emails and said he would show them why I may have trouble coming into work.

That’s when he showed me that he had an email open and addressed to the guys, with several of the pictures of me dressing, putting on makeup, and sucking his cock.  The body of the email said “As you can see, things have changed a bit.  SHE only wears dresses now, and SHE can come work for you if that’s fine for you.  But as you can see, she sucks cock like a princess. I am making her press SEND, so you know she is aware of this email.”

I clicked SEND, with tears running down my cheek.

A few weeks later, I was eating lunch after shopping for makeup and I saw the old coworker walk by.  He stopped, looked at me as if trying to decide something, then winked and walked away.

[cherigurlmn]

The Dress

Daddy John asked me one night if I went to prom in high school.  I told him that I was too shy to ask anyone, so I didn’t go.  He smiled and nodded.  He told me that since I was only 19 I could fit in easily enough.  I looked at him questioningly, but he just smiled and walked out my room.

A few days later, he came and told me I was going to have a visitor so I needed to put on a pretty dress.  I did as he told me, and as I was finishing my makeup, I heard the doorbell and Daddy let someone in.  He called to me and I went upstairs.

He was sitting on the couch with a young man and Daddy waved a hand at me.  “Look, Jacob.  Just like your dad told you, she looks nothing like a boy at all.”

The boy was pretty quiet and didn’t look at me directly a lot, but I caught him stealing glances.  Daddy broke the silence and told me that Jacob was a senior in high school, but he was closeted and gay.  And as a main member of the football team, he didn’t want his secret to get out and maybe hurt his chances of going to a good college.  

Jacob’s father suggested taking me if he really wanted to hide it, so he called John and asked.  And here we were.

  Daddy had me twirl and be pretty, and he had me show Jacob that the voice lessons I had been taking were paying off.  We all chatted for a bit and Daddy told me that he had already picked out a prom dress for me, and if Jacob was interested, I could go as his date.

My eyes went wide as I realized I was really being set up on a date in PUBLIC with a BOY.  And if I didn’t pull it off, it could be bad for him.  I must have looked panicked because Daddy said in a whisper “You’ll be fine.”  Jacob said he would love to have me go to prom with him, and as we went downstairs to look at my actual prom dress, Daddy said very clearly  “And Cheri...give poor Jacob a nice blowjob as thanks for asking you to prom.”

I could only nod.

[cherigurlmn]

The Realization

About 2 weeks Daddy threw out all my boy clothing and I had been dressing femme every day, he told me we needed to run some errands so I needed to get dressed so we could go.

I looked at him, unable to say a word and he asked me “Did you think you would never leave the house? Go get something pretty on.”

I will never forget how terrified I was as we walked through a grocery store in a dress and heels, with a purse over my shoulder.  I kept expecting someone to point and laugh but it never happened.

When we finally left the supermarket, as we got to the car he looked at me and said  “Look how quick you learn.  It’s very natural for you.  I told you that you were born to be a girl.”  Then he handed me $20 and said  “Oops you forgot to get gold glitter eye shadow and tampons.  You better go back in.  And I want you to wink at the guy who checks you out.”

And I did it.

[karlylynch18]

sissycaption sissification sissy captions

[cherigurlmn]

Since I was Asked

I got a lovely concerned email last night, asking if my posts were true or fantasy.  And she was very concerned that if they were real, was I ok now?

Well, I hope this answers the questions.

Yes, what I’ve written here is true. At first, I was so scared but eventually I realized that where he was pushing me was amazing.  He saw it inside me and brought it out, and I’ve never been happier.

Were some of the adventures I had with him kinky and dark for some people? Yes, I totally acknowledge it and understand how it could be upsetting, but I promise you... I willingly ended up with him for over 3 years, and I loved it all.

To this day, I am always so thrilled at the simple act of putting pretty ribbons in my hair.

[colleeneris]

[littleyoungsissy]

♥ littleyoungsissy​ ♥

[sissyspermdump-deactivated20180]

[gymbunnycandie]

[cherigurlmn]

He waited for the right...person

I moved to a new city with a friend.   Then his relatives  (where we were staying) said we couldn’t both stay... so I found another place...I rented a room from an older guy.  He seemed really excited to have me move in, too.  He asked all kinds of questions, and something inside me said that he was thrilled I didn’t know anyone else in town.

The moment my friend had to move back to California, (about a month after I moved into my new place), it all changed. I came home from work one night, and he asked if I really liked the job. I laughed and said of course not, but it paid bills.  He smiled and said he could get me something else... he insisted I call and quit, so I did.

The next day, I went out to the store and when I got back, he was in my room in the basement and clothes were absolutely everywhere.  But... they weren’t my clothes... they were girl clothes.

I asked what was going on and who the clothes were for.  He didn’t answer, but went up the stairs, and at the top of the stairs, I heard a CLICK.  He came back down and said  “Well, they’re for you...”  I laughed nervously and he said “No, really...I already threw your other clothes in a bag, and once you get out of the clothing you have on, you will only wear what I tell you.”

He held up my mobile phone he had picked up and said “No one is looking for you. No one you need to call.  You are going to do what I tell you.  Take off your clothes.”  He is over a foot taller than me and over 100lbs heavier.  He walked toward me and loomed over me as I tried to figure a way out of this.

He grabbed my Tshirt and pulled it up.  I started crying and he said “It’s ok to cry...”  He pushed me over the bed, and yanked down my shorts and underpants in one go, then took a step back and said “Wow, you are even tinier than I thought.”

He turned and walked out of the room, leaving me naked.  He said he was going to throw all this boy stuff away, and he would be back in 10 mins.  I had better have something picked out and put on by then.

I sat on the bed and cried, terrified and confused.  About 10 mins later, I heard the door open and he called down “You better have something on when I get down there.”

I reached for the nearest thing...and put it on.

[lazygirlguidetomakeup]