Archive for the ‘Crossdressing Phone Sex’ Category

Sexy, Sleek Clove Cigarettes

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Having a cig is so satisfying. I love how my lips feel wrapped around a clove cigarette. I feel a tingling as I suck the smoke in deeply. It is so incredibly relaxing.

I can’t help but laugh when I see the look on your face. You aren’t imagining my lips around your worthless cock, but you’re thinking what it would be like to be me. You want to wear my sexy clothes, and have the same effect that I do on men. You can try. You can dress up like me, smoke like me, and even try to be a mistress. You aren’t me, and you never will be like me.

Do not fret, I have other uses for you. I need an ashtray. I so dislike having butts around my lovely loft. So many ashes and so much work. You’ll be down on your knees with your pretty little mouth open, and ready to take all my ashes. Anything that remotely is near my mouth you crave.

There you are in your lovely pink silk panties, patiently waiting for some ashes to fall in your mouth. I look at you, taking a long deep drag. You watch the smoke waft. You touch your little boy clitty as I put the cig out in your mouth. Good Girl!

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Lady RayneWritten By: Lady Rayne
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Valentine’s Day Panties

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 You have been snooping in my bedroom again, haven’t you?  You see the sexy red satin panties on my bed. For a brief moment you think about me in them, but then your thoughts go in a very different fucking direction. You check the time, and know I won’t be home for several hours. You giggle, as you rub them against your face, feeling how soft they are. Checking the clock again, you  slowly strip as you watch yourself in my full length mirror. You put on Bump and Grind, and begin to dance as you slip on my red panties. You run your hands down your body, feeling so sexy.

You hear laughter at the door, and turn around to see me and 2 friends watching you. Don’t you look so adorable?  My girls dance with you for a few, as I pick out sexy lingerie for you. A red clincher, red 6 inch stilettos, red satin bra, cherry red lipstick, and a red wig. You look like a slut! You’re so excited, and begin to dance some more. 

You beg us to take you out for the night with us. We pick the perfect dance club. There is always hot professional men looking for a walk on the wild side. You flirt with the bartender, and you get all our Painkiller cocktails for free. That gives us all an idea. We’re all giggling but you have no idea why. I talk to the bartender and soon men are waiting in line at our table. I take their money and follow you into the restroom. You pull up your dress and take off your panties. A line is forming, and I watch you take 4 cocks at once. Quite impressive, I must say.

Happy Valentine’s Day to all my Sissy Sluts!

 

HarleyWritten By: Harley
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Jade’s Closet

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http://www.smittenkittens.net/Journal/wp-content/uploads/2019/12/jade1.jpgAre you jealous of my naughty schoolgirl outfit? You wish you could wear something like this, don’t you? I bet my hot, little outfit would look so good on you. In fact, I have many outfits in my closet for you to wear. After I pick out the perfect, slutiest outfit, I’ll do your makeup. All my girlfriends want me to do their makeup, so you’re in good hands.

My strap-on will defiantly be coming out and shoved in your slut holes, along with other toys from my collection. Don’t get to use to the rubber though, because soon enough you’ll be experiencing the real thing.

I will make you look and feel really girly. I know you’ve been fantasizing about this for awhile now, and this is the time to make you the perfect sissy you’ve been wanting to become. Once you step into my closet, there’s no going back to your plain ole boring self again.

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Written By: Jade
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Sissy Ends Up In Military School

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A Mom came home from her job. Her co-workers made plans to celebrate the completion of a big project that night at the bar. There had been so many late nights, and Mom felt guilty about leaving her teenage son alone so much. Instead of going out to celebrate, she left an hour early because she wanted to cook him a special dinner and hang out with him. 

She drove home and entered the quiet house. She checked his bedroom and found it empty. Mom goes to her computer and looks up his location through an app on his phone. Shocked to learn that he must be home, but she must be doing something naughty because he is so quiet. Without making a sound, she searches the house, and the last door she opens is her bedroom. She finds her son! 

Mom discovers him wearing her expensive lingerie, sucking on the dildo from her nightstand. WTF? Her son is a Sissy! The Mom falls to her knees and breaks down and bursts into tears. The son stands there ashamed and begs for forgiveness. Mom spends the night researching solutions on how to turn him from a sissy to a real man. She wakes her son at dawn and gives him the news. 

The furious mother informs her son that he needs discipline and needs to be surrounded by alpha men, real men. He needs a mentor, someone who will break him of his sissy ways. Mom has already arranged to send him to military school, a boarding school. Being a single mom, maybe she cannot teach him how to be a real man. She hugs him and says this is the best thing for him. He will leave today. 

On his first night in the dorm, all the boys identify him as a sissy, and they treat him as such. They force the new boy to dress like a sissy, frilly panties, bra, thigh-high stockings, and lipstick. They hold him down and fuck his little sissy boy mouth. The boy loves his new home. His fantasy becomes his reality. Now he can be a cock sucking sissy whore every night! 

 

Sarah JesseWritten By: Sarah Jesse
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Secrets

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  It is our first date. I hadn’t seen you since high school. You look hot as fuck, but there is just something that seems different. I can’t quite figure it out.

After a fun date, I was starting to think the chemistry was off. You are in town for a few days so you stay at The Ritz. You invite me to spend the night. You tell me not to worry because the suite is huge, and I can have my own room. Definitely looking like no chemistry. Of course, once I got a look at your cock while you are changing, I knew there definitely won’t be any fucking.

I fall asleep, and wake up to the sounds of you giggling and trying on my lingerie.  You are posing, smiling in the mirror, and being very girly. Things are starting to make sense. It’s still a bit early, so I excuse myself, and explain I have forgotten a few things. You ask to go with, but I tell you to try on more of my things, and I will be back shortly.

I return wearing something most unexpected. A man’s suit. You lick your lips when you see the bulge in my pants. You crawl to me and unzip my pants. You smile when you see I am in sexy black lingerie. You are in frilly, lacy pink. You beg me to let you suck my strap-on. While you are on your knees sucking my cock, you hear a knock at the suite door. There is 5 very tall, muscled and hot men. I sit back and watch. Commanding you to be a good little girl, and please my friends. This is going to be one hot, dirty, sexy, filthy night.

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TiffanyWritten By: Tiffany
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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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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

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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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