Archive for the ‘Crossdressing Phone Sex’ Category

Desperation Lead to Transformation

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Desperate Times Call for Desperate Measures

He has been unemployed for a while now. He had been a Professor of Woman’s Studies at a small university. Because of budget cuts, they had eliminated his job. He was popular with the ladies. The young, hot women in town found him sensitive and sensual, a man who really understood women and knew how to please them.

It’s hard to feel like a man when a beautiful lady at the bar asks what he does for a living. The ladies lost interest in him and he had not had a date in months. Also, his bank account was dwindling down to nothing. He was losing everything he worked for all these years. 

He learned of a teaching position at an elite all-girls college on the east coast. There was one problem, they had very few men on the faculty, and he knew his chances to get hired were not in his favor.  

Instead of wallowing and feeling defeated, he contacted me. I oversaw his full transformation to becoming a woman. I gave him a head-t0-toe makeover. He had always enjoyed wearing panties and thigh highs, but only for me in private. I coached him about hair, makeup, and lingerie. Although he found it all humiliating at first, he got the job.  With my help and counsel, he nailed the interview.

Feminization is possible, so let’s have some fun. 

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BrynnaWritten By: Brynna
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Rainy Days Get Cozy and Kinky with Mommy

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You and your sweet Mommy Morgan are enjoying a  fun summer. The weather in the Midwest, at the start of summer, was cold and rainy, but July was beautiful. There are only a few weeks left of summer before you have to return to school. Mommy has been shopping and running errands to get you ready for a new school year.

Today, you woke up late. The sun in your eyes did not wake you up this morning. The sun is hidden behind the clouds today. It is a rainy day. At first, you mope around the house complaining about being bored and having nothing to do. Mommy tempts with you movies, books, a jigsaw puzzle. You roll your eyes at her and pout as you continue to play your video games. Even that gets boring.

You look around the house until you find Mommy painting her fingernails and toenails a pretty shade of pink. She looks pretty sitting there in her shorts and tight sexy top. You lay your head on her leg. She asks you to finish painting her toes. You admire your work. They look beautiful, and you blow on them to dry them.

Mommy rubs her fingers through your hair and whispers something naughty in your ear. “How about since you are so bored that Mommy paints your fingers and toes with this pretty shade of nail polish?”

You are horrified at the thought. That is for girls, only girls, but Mommy has a way of convincing you that it would be a super fun and silly thing to do on a rainy day. You agree to let Mommy do your nails, and you are surprised at how much you like them. Then she suggests panties and bra. What? Has Mommy lost her mind! You remind her over and over that you are a BOY, not a GIRL!

By the time that Mommy gets done with you, you are wearing pink panties, pink bra, tall white socks, black heels, plaid skirt, and white top. Your hair is in pigtails, and you have lip gloss on your lips. You look like a little slutty schoolgirl! Now it is time for Mommy to show you how girls play together!

In need of a wonderful forced feminization session with Mommy Morgan?

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Mommy MorganWritten By: Mommy Morgan
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Lingerie Princess

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     I love lingerie so much! Even if I have the odd night where I am alone, I still wear sexy lingerie. Red and black lingerie is my absolute favorite. I am very picky too. I have every little baby doll, teddy, and slip on scented padded hangers. 

That is how I caught you!

You were doing some tech work for me, and I came home for lunch to bring you some sushi. I took off my heels, so I imagine you didn’t hear me at first. I called your name, and then you frantically began to put my lingerie back on hangers. In your haste, you forgot the panties that were tossed from the hamper.

     I always suspected it was you. You seemed to be way too interested in my lingerie even with it not on my banging body. Don’t be embarrassed. I always wanted a dress-up doll. Let’s see, I think pastels work best for you. Don’t be shy, I have always wanted a Lingerie Princess to play with. 

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DaphneWritten By: Dirty Daphne
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Lady Rayne Severely Punishes Slave

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You arrive late which makes me more than just a little annoyed with you. A close friend was in town for the day, and I promised her a hot and nasty session with two of my slaves. “You are late faggot, and you have embarrassed me”. I yelled at him. He began to beg because he knew his punishment would be without mercy. I know exactly what my bitches secretly like, and really fucking hate.

I grabbed him by his collar, and dragged him to my guest bathroom with my friend following close behind. He dropped to his knees looking up at me and pleading. “Please, not the enema Lady Rayne”.  He actually had tears in his eyes, and promised to do anything. That was laughable as he is my fucking slave. My friend got the enema ready. We made him bend over and spread his ass cheeks. He pleaded even more now for me to let him release the dirty liquid.

We went out for a few hours leaving him filled and in pain from holding it in. We returned in good spirits, and ready to let him release. When I checked on him he apparently had an accident, and was desperately trying to clean things up. That just called for even more severe punishment. He is a bit of a “priss”, and always begs for the GQ type of men to suck off. Not tonight, faggot! You are going out, and sucking off dirty, small, useless dicks. That is the other thing you hate with a passion!

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Lady RayneWritten By: Lady Rayne
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Sissy Boi Phone Sex

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    malaya   I see the way you look at me, but it isn’t that you want to fuck me, you want to be me! Trust me little sissy bitch, you couldn’t handle being me. You are way to girly and giggly to be me. To be me, you must have ice water running through your veins and have no mercy with fools like you. 

Go to the garage and get ready for your company fag face. I have your pretty pink clothes hanging on the rack. I want to see your makeup perfect like I have taught you and that wig better be on fucking straight. Make sure it is pinned on so when you’re getting your face fucked it doesn’t come off. Who the fuck wants to see a bitch without her hair?

The men are on their way over and I plan on you making me a lot of cash. I did pay for your clothes, makeup and hair sissy slut. Don’t forget my cruel streak. Disappoint me and your night terrors are minimal compared to what I will do to your ass.

  Deviant Malaya Max

 

MalayaWritten By: Malaya Maxxx
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Say “Yes” to the Dress

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Dani 1We should have the Ultimate Girls Day together!

You are dressed today in a pretty blouse, a navy skirt, pumps, and stockings.

First, some lingerie and shoe shopping. That is the best way to start any day. Then, a light lunch, possibly salads and a couple of glasses of wine. We love our girl talk and gossip over lunch.

On our way home, I talk you into stepping into a bridal salon. Trying on wedding dresses, what could be more girly or more fun?

The staff is giggling at you, but find several wedding dresses for you try on. 

Once we pick the perfect long white dress, I am going to ravish you in it while the ladies watch us fuck each other. 

 

 

DaniWritten By: Shemale Dani
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 Email- shemaledani@aol.com

 

There Is Nothing Like The Real Thing

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rayneSlave, you have such a hard time saying what you really want and need. We both know a big, thick hard cock is preferable to a dildo. Sometimes when I am pounding you hard you beg for my cock. You plead for my thick, hot load of cum.

I feel it is time to cut you off till you can admit it really is a cock you crave.  You dress like a sissy slut, want to devour the cum running down my leg, so admit your needs to Lady Rayne. I won’t tell, but I will bring in a sexy man, with a huge cock to take care of both our needs.  I know what my bitch boi needs!

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Lady RayneWritten By:  Lady Rayne
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Let’s Do The Timewarp Again!

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caidynI love Halloween and all the parties and fun. There is one tradition my friends and I have and that is going to the Rocky Horror Show. I am always Magenta. I love how sexy she is in her maid outfit and lingerie. After the show, there is always an after hours party with the cast. This year there was a new Count Frankenfurter and OMFG he was beautiful. If I didn’t know better, I would have thought he was a chick. I asked around but know one seemed to know him.

It was around 2 am and no one was feeling any pain from hitting the well stocked bar. People were kissing in various corners, a few couples fucking. They were threesomes, foursomes and just a whole lot of fucking. I noticed Count Frankfurter having a drink sitting by the fireplace just crossing and uncrossing a pair of beautiful legs. He motioned for me to come sit with him. OMFG, I will say it again, he was beautiful and his huge dick was unmistakably hard.

We began to kiss, and he took my hand and lead me to a huge cheesy looking bedroom. It was rather girly looking for a man, a round bed with red velvet comforter? Okay then! He slowly undressed as I watched mesmerized. When his corset came off, I saw those breasts were real, and I just wanted to lick his hard nipples. Ohhhhhh, he isn’t exactly a he! I was about to fuck my first tranny and there is no way I wouldn’t let my boyfriend in on this. I texted him and we all jumped on the big, round bed and began to play.

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CaidynWritten By: Caidyn Cross
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Bree’s Pantyboy Playhouse

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Sexy BreeTuck your little dick inside your sweet little pink panties. All my girlfriends are coming over for a sexy lingerie party. You can hang with us girls today because you possess more girly traits than masculine ones. For starters, your cock is just so tiny that it is more like a clit. Also, your ass has a round curve which is why you look so cute in panties! You are soft and small, petite and sweet, not big and strong like our boyfriends. We tease you and embarrass you, but you love humiliation. 

You are one of the girls. We tell you our secrets, we let you go shopping with us, you borrow our clothes, and we put makeup on your face. We tease you about being a girl, and you love it!

Be a good girl and you can cum in your panties.

Bratty Bree

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Bree

Written By: Bree
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Kinky Lingerie Shopping Trip

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BrynnaYou and I take a middle of the week shopping trip. We stop for lunch at a little bistro. The handsome waiter talks the two of us into sharing a bottle of wine, instead of just getting a glass. Something about red wine makes me horny. After lunch, we are both very relaxed and feeling a little naughty.  We continue our shopping. The next store we enter is an expensive upscale lingerie boutique. I find a La Perla bra and panty set to try on, so I step into the dressing room. You find a Chantelle bra and pair of panties in my size, so you bring it to me while I am trying on the first set. I like the lingerie you picked out of me, but we are both feeling sexy, silly, and a little kinky, and I talk you into putting on the lingerie. I help you out of your jeans. I rub your cock to get you very turned-on, then I watch you put on the bra and panties. We start making out. Your cock is dripping precum into those panties. Our giggles turn to moans. We are going to go for it and fuck right there, but we hear someone approaching. The manager kicks us out of the store. She demands payment for the lingerie that we are wearing. We give her some cash and don’t wait for the change. We throw our clothes on and run out of the store red-faced and laughing.

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We feel like a couple of naughty kids. I see a big bulge in your pants, and my pussy is throbbing. We need to fuck, and fuck now! I get a very kinky idea. We head to Dillards. You think we are going for more lingerie, but I pull you into the men’s suit department. There is a very hot guy always working there. I talk him into a sexy threesome in the big dressing room. He loves that we both are wearing our new lingerie. I talk you into sucking his cock after he makes me cum. You take his cock into your mouth and suck him. We end up fucking and cumming all over each other.

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BrynnaWritten By: Brynna
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Old Lingerie in Trunk in Attic

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BrynnaYou have an unfavorable task to complete this weekend. The family is getting together to go through your Aunt’s big old house. It is something that you have been dreading. There are so many things that you would rather be doing on your weekends.

Your oldest sister has taken charge, and she has assigned you to the attic. There is a lot of old junk up there. Most of it will be thrown out or donated. It is going to take a while. You don’t have the sentimentality for keepsakes that your sisters have.

You have made your way through most of the items in the attic. There is a heavy old trunk in the corner. You open it. You find a wedding dress and underneath some very sexy black vintage lingerie. Maybe this was lingerie worn on her honeymoon. You cock tingles. You hold it up to and imagine what this sexy lingerie from the early 60’s would feel like on your body. Auntie had a naughty side. Who knew? Auntie always seemed rather conservative, but we all have a secret side, don’t we? 

brynna 16You put the lingerie in a box and put that box in your car. Your sisters are arguing over some dishes and a clock. This is your opportunity to get away and head for home. You are thrilled by what you found in the trunk. 

As soon as you get home, you take a shower. You style your hair and put on some gorgeous red lipstick. Carefully, you pull on the fragile, silk black foundation garment. You attach your own black Woolford stockings. You slip into your classic black pumps.

Wow, you absolutely look stunning. You have never felt so girly in your life! The transformation is incredible. You are very sexy! You stand in front of the mirror admiring your curves. You run your fingers over the silky fabric. You are very sexy! 

BrynnaWritten By: Brynna
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Panty Boy Shopping Spree

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gingerOne of my favorite panty sluts is having a birthday soon and I know the perfect present… a shopping spree! Every once in a while, he’ll decide to be a man and take me, so sex could be good, but I know him better than he knows himself. He would be so much happier with the panties.

He always enjoys when I dress him up and turn him into a sexy little whore. We’ll pick out all sorts of panties together and then he can come home and model them for me. When he’s in his tall sexy heels, he struts around like a high priced call girl. Since he’s such an obedient little slut, I’ll throw in some stockings and garters too. It won’t take much prancing around out of him before I have him on his hands and needs with my fingers inside his “cunt”. It will be the best birthday present he ever had!

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GingerWritten By: Ginger
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Cuckolding My Pantyboy

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Bratty Bree

I ask you to party. You think you are my date! That is hilarious! You are small! Well, yeah you are tall, but you are small where it really counts! It is so humiliating for you when you realize that you are not my date, but rather the panty boy cuckold for the party! College girls like me need a good laugh as much as we need a real man to fuck us.  

I have cute pink frilly panties for you to wear. All the girls are gorgeous. You can look but not touch.  You are just too small. You are relieved that your tiny cock is tucked in your panties. All of us girls are talking about all the guys we fucked over the summer break. Every single girl is talking about the size of the guy’s dick. Yeah, silly, of course, size matters! 

Finally, the highlight of the night! A real man joins the party. You are forced to your knees and made to suck his cock. All the beautiful college girls are teasing you, calling you naughty names, embarrassing you. Your eyes are watering. You are gagging on his cock, but secretly the more humiliating, the harder your own little dick gets. Humiliation makes you hard!

I pity you.  Little panty boy cocksucker, play with your tiny dick and cum in your pink panties!

Bratty Bree

Bree

Written By: Bree
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Wearing Mommy’s Bikini

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MorganYou have always had a fascination with Mommy Morgan’s lingerie.  This summer, Mommy has been rocking sexy bikinis. There is an old pink one that is one of your favorites. You love pink because it is fun and girly! While Mommy is out shopping, you find her pink bikini hanging in the pool room. You are so curious that you pick it up and run into her bedroom. Quickly, you take off your clothes. Standing naked in front of the mirror, you hold up the top and then the bottom next to you. Mommy walks in. You are both speechless for the moment. You look to the floor, naked and ashamed.  

Mommy understands. She ties the bikini top around your neck and chest. She slips you into the pink bikini bottom. After many hugs and kisses, the two of you hit the backyard pool, two hot girls in their bikinis. See how fun it is to be a girl! 

Love you, Baby! 

Mommy Morgan

Mommy MorganWritten By: Mommy Morgan
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Humiliation in the Red Light District

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BrynnaHumiliation is the name of the game for you. The more humiliated you are, the more excited you become. Being put on display in very embarrassing situations is thrilling for you, and entertaining for me. 

You work for me in the red light district. There are clubs for every erotic desire lined up on both sides of the street. I own one of the best clubs, and you are my star. Every night, you perform up on a stage in front of a large audience.  Before the show, you and I stand on the street, wearing only our lingerie to lure people into my club. Yes, you wear whatever slutty little outfit that I select for you: corsets, bustiers, bras, thongs, stockings, pantyhose, chemises, bodysuits. You have to stand on the street enticing the crowd to purchase a ticket for the show. You must stand there and endure all the name calling, whistling, and illicit touching until every seat is full, then the real show can start. 

Every night there is something different. Always new tantalizing treats for my voyeurs to enjoy. Sometimes on stage, you are dressed like a slutty little whore, and sometimes you are completely naked. I instruct you to perform for the crowd. One night you might put on a masturbation show. Occasionally, I use my strap-on and fuck you which is a real crowd pleaser. You service the ladies on Ladies Night. When I want to push the envelope, there are water sports for you. Every Friday night, you become a cock loving, cum drinking whore. I bring men up from the audience. Either one at a time or a group of men with very large cocks. They can use your mouth and then your ass to put on a fucking fantastic sex show. 

It is humiliating to be used in this manner, but you, my naughty exhibitionist, love it! 

Mistress Brynna

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BrynnaWritten By: Brynna
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Sissy Slave Must Learn The Rules

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Rayne

There is always the one disobedient sissy slave that doesn’t seem to understand his place. He loves dressing up but needs to be forced to properly suck and take a magnificent cock. My newest seems to think he is a cross-dresser that gets to fuck his Lady Rayne.  Pathetic, is it not? I found it rather amusing when he belonged to another Mistress, but as mine it is becoming annoying.

He came to my den for his nightly inspection.  His legs were smooth, his makeup perfect, his wig crooked and I won’t even begin to to tell you how he walked in his heels. As usual, he got things partially right.  When he saw my displeasure he dropped to his knees and began to beg. I slapped his face as his makeup was beginning to smear from his useless tears.

The door opened and three huge men appeared. I sat back in my chair, smoked a relaxing Djarum as they began to tear off his frilly pink undergarments. His cries were hilariously pathetic.  Was it wrong for me to laugh? He will learn his place after tonight.

Lady RayneWritten By: Lady Rayne
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AIM- deviantladyrayne

My Slutty Pantyboy

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gabrielle

Hey, Pantyboy!

Now that I have your attention, I want to tease and humiliate you about your panty fetish. You stole a pair of panties when you were young, maybe mom’s or sister’s panties. You sniffed. You were instantly hooked. The panties were soft, and you put them on. Soon you tried on her other pieces of lingerie. Now you are happiest and feel sexy as a girl. 

You wonder if that lady at Victoria Secrets knew those little pink panties were for you. You are a true sissy. You crave the “girl experience.” You have a hidden collection of lingerie. You need your nails and hair done. I have the perfect shade of pink lipstick for summer. You desire to be a girl, hot and promiscuous. A call with me is a great way to be a sissy and be slutty.

 

 

GabrielleWritten By: Gabrielle
1-866-677-6709
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Sale At Victoria Secrets

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Bad lil Bree

I was working my part time job at Victoria Secrets. It has been crazy due to our big sale, but it is always so much fun helping the panty boys buy new lingerie.

Yesterday there was a “manly” looking man in the store, but he didn’t fool me.  I knew he was a sissy. He asked where the Body by Victoria thong panties are located. He wanted pink.  He said that the panties were for his wife, but I didn’t believe him.  I knew the panties were for him. I can always tell. It has to do with the guy’s body language. When a panty boy gets close to panties, there is a twinkle in his eyes. His skin is flushed.  He is imagining the soft and silky panties touching his cock and balls.

While I was ringing up the pink thong, I invited him to the storeroom to see the new panties that had just arrived. He got very excited and graciously accepted my offer. I took him in the back, confronted him about being a panty boy, and made me admit that he is a panty wearer. I made him strip, and the other girls and I got him all dolled up! Panties, matching bra, black thigh highs! We put lipstick on his lips. I pulled out my dildo from my purse and made him suck it. Then the girls and I took turns calling him names, teasing about being a panty boy and fucking his “pussy” with that wet dildo. It was so funny when we made him cum in his new panties. He was so humiliated and embarrassed, but I can’t stop laughing or sharing this story with all my girlfriends. 

BreeWritten By: Bree
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Want To Be A Sexy Girl, Like Me?

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DaniLike wearing panties?

Why not take it to that next level?

Let me completely transform you into a girl. We will get your hair, nails, and make-up done. We will make a shopping trip to Victoria Secrets and get some new lingerie for you. Maybe you need some thongs and new black thigh highs. You can go through my closet to find a slutty little outfit that is just perfect for you. A dress that is tight on your ass. I have a necklace that will draw attention to your tits.

I will take you to a club where we can dance and flirt the night away.  We tease the boys as we put our hands on each other, and do some dirty dancing, grinding our hot bodies together in very sexy club dresses. I will take you into the VIP Lounge area, and we will get down and dirty. Some very sexy girl on girl action! Very passionate kisses, tender caresses, licking each other between our legs and fucking each other!  Spending time with me, your favorite shemale, is way more intense and sexy than just simply jacking off into a pair of panties.

Join me is a very erotic sexual adventure!

XOXO 

DaniWritten By: Dani
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AIM- shemaledani

 

Princess Time with Paris

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parisYour such a cross dressing slut. I know that underneath your manly physique is a sissy slut just aching to cum out. You dream of a princess like me taking you by the hand to guide you through feminzation.

Gather your girly items and get to your room and let’s have some princess time. We’ll make it an intense sissy slut training session. First, I’ll start with a little humiliation, I love being amused. Your small dick will never serve any purpose to me. You’ll be trained to dress like a slut and take cock like a slut.

I’ll then order you to draw a fabulous bubble bath for yourself. We’ll start by shaving that disgusting man hair off your body. You have so much work to do. After you’re nice and smooth, you’ll find a sexy outfit laid out for you. White lace panties with a padded bra, a short hot pink dress with a pair of 6 inch stilettos. Get that cute butt moving and let’s see how you look.

ParisWritten By: Paris
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