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Allie sits in front of the vanity mirror, thinking about how she wants to make up her face for tonight's date with Alex. Now that Carla's totally supportive of her being a prostitute, she likes to ask about the guys she dates.

When Allie told her about Alex's thing for little sissies, she braided her hair in pigtails and painted her nails red before she went to work. She told her to wear her oversized, pink-rimmed glasses and offered some makeup suggestions to make herself look like an innocent schoolgirl.

Following Carla's advice, Allie goes with pinkish eye shadows and gives herself rosy cheeks to match the cute little red bows Carla tied on the ends of her pigtails. Her lipstick is a darker shade of red than she usually uses, but it matches her red fingernails a little better.

She found a cute pleated skirt and blouse outfit on sale a while back, and she bought it especially with Alex in mind. After pulling a pair of cotton pink-and-white striped thigh socks over her knees, she can't wait to put on her short skirt.

She loves the way it looks, with just the right amount of bare leg showing between her socks and the plaid-patterned skirt. It looks even better when she puts on the blouse. Her pink sneakers are the perfect finishing touch to the sissy-girl look she knows will turn Alex on.

"How do I look?" she asks Jill, who's sitting at the kitchen table, writing in her diary.

"Like a cute little sissy slut," Jill chuckles.

"It's not too slutty, is it? I have to be seen in public when we're at dinner."

"Naw, you'll pass in public just fine. I like how you did your makeup. You're getting really good at it."

"Carla gave me a few suggestions before they went to work. It's so nice having her and Rosy around."

"It sure is. I don't even want to think about where we'd be without them."

~~~~~~~~~~~~~~~~~~~~~~~~~

It's a bitter-cold, January day in Iowa, and she's glad to have the warm socks protecting her legs when she gets out of her car and walks to the hotel lobby. Alex doesn't seem to have arrived yet, and she gets a little self-conscious about the way she's dressed. Luckily, there aren't too many people around, and her winter coat covers up most of her schoolgirl outfit.

Not wanting to be noticed, she's standing by a window, staring at the white, wintery landscape, when she feels a tap on her shoulder. "Is that you?" a familiar man's voice says.

She turns around, and there's Alex. "It's me, daddy!" she giggles.

"Well look at that... my little sissy's in pigtails. I like it."

"I did my hair just for you, daddy."

"You look real cute in pigtails. Is my little sissy-girl hungry?"

"Yes, daddy. I'm ready for dinner. I can't wait for my dessert!"

As they walk through the dining area, some of the customers give her funny looks. She wonders how ridiculous they must think she looks. She's more concerned about embarrassing Alex than she is about herself being embarrassed. She's relieved when the hostess takes them to a table in a semi-secluded area, where she doesn't feel too embarrassed taking off her coat to reveal the rest of her sissy outfit.

Alex cuts the sissy talk once they sit down; they both know it's just a game they'll be playing later when they're alone in their room. They've actually grown quite fond of each other, always enjoying a pleasant conversation whenever they have dinner together.

"I like the way you dressed up for me tonight, Allie," he compliments.

"Thank you. My wife Carla helped me out with it."

"If I had a daughter, I'd like her to look just like you. I gotta tell you... I nearly fell out when you told me you got married over Christmas. I wasn't expecting that at all. I'm so used to seeing you and Jill as girls."

"The girls we married are really special. They've always seen us as girls, and they've helped us out so much to get where we are. The only reason me and Jill can dress up as good as we do is because they taught us how. We weren't really planning to get married. It just kinda came up on us real fast-like, and we all knew it was the right thing to do."

"You look really happy. I can see it all over your face. So... tell me about the house you bought."

"Well, I told you it's in the country, on fifteen acres. It's a nice house, but it needs a lot of work. The lady who lived there before didn't keep it up after her husband died a few years back. We know it needs a new roof, and it's gonna have to be painted. The inside is old and depressing. It'll all have to be remodeled."

"Sounds like it. Do you have enough money to take care of all this?"

"We have plenty of money, but most of it's in cash. Gary told us we can't put too much in the bank because of the way we make our money. We have to watch out for the IRS. We like to pay cash 'under the table' as much as we can, if you know what I mean."

"I know exactly what you mean. We all do it whenever we can. I can use my contractor crews to do the work. You can pay me in cash, and I'll pay them with company checks."

"You won't get in trouble doing that, will you?"

"Nah... we do over ten million in sales every year. I can run a remodel project like this through my books as miscellaneous expenses. It won't be a problem at all. I can write it all off and pocket the cash. It'll work out good for both of us. When do you close escrow?"

"In about two weeks, I think. How soon can you start working on it?"

"Right away. Work is real slow this time of year, and my crews are hungry for work. They'll get right on it."

Allie's glad to hear that. She's excited talking about it over dinner, as Alex tells her about all the different options they'll have. She didn't really like her dates with Alex much at first, but she's gotten to know him a lot better since they've been dating. She now knows him as a nice man with a kind heart, and a fetish that needs to be satisfied.

Alex has three sons, but never got the daughter he always wanted. He's a family man, and his love for his wife and kids keeps him from ever considering having an affair with a female or picking up a whore off the street. Going on safe dates with Allie helps him fill a void in his heart for the daughter he never had, and it explains why he has such a fetish for sissies. Allie felt weird calling him daddy at first, but she's gotten used to it. She kinda likes playing his little game. She doesn't mind being his sissy.

She puts her arms around him the moment they close the door to their room. It's sissy time again.

"Is daddy ready to play?" she teases.

"Yes, I am, you little sissy-slut. Do you remember what daddy likes first?"

"Yes, daddy, can I taste your lollipop again?"

"Do you remember where I keep it?"

"Yes, daddy."

Sometimes she can barely keep herself from laughing at how ridiculous this is, even though she has fun doing it. Like the professional whore she is, she knows how to become the fantasy sissy-slut Alex wants her to be. He pays her good money to do it, and she can always count on $300 from him every single month. Sometimes he even calls twice a month, that's how much he likes Allie.

Like a good little whore, she gets on her knees, unzips his trowsers, and puts her hand inside. "Oooo... daddy! I can feel it!" she goes into her act.

"Don't just feel it, you little sissy," he says in a firm voice, "take it out and taste your dessert."

She pulls out his cock and licks the head. "Thank you for dessert, daddy. You taste so good."

"Eat it up, sissy! You know you love it!" his mood turns abusive.

"I do, daddy, I do love it."

"Then shut up and suck! Show daddy how much you love it."

Allie's used to his abusive talk. He does this every time she dates him. He gets off on it, and it's Allie's job to get him off. She's at work being his personal whore, and she knows she'll be back home when it's all over.

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She undoes his belt and helps him out of his pants. He grabs her head and forces his cock down her throat. His cock isn't all that big, and Allie has no problem deep-throating him. She pretends to choke and gag on it, though, because she knows how much it turns him on.

She opens her mouth wide for him, obediently looking up into his eyes as he fucks her face. He loves the feeling he gets from it, his sissy on her knees, willingly playing out his sexual fantasies, while he stands over her as her master.

She sucks him quite a while, he likes blow jobs the best. Like she does every time she blows him, she stuffs his balls into her mouth and lets him slap her on the face. Most girls would feel degraded being treated like this, but to Allie, it's just another date. And besides, no one else knows about it, besides him and her.

"I think you've had enough dessert, sissy," he tells her. "It's time for my dessert. You know what to do. Don't you...? Sissy?"

"Yes daddy, I'm a good sissy, and I know what to do."

Like she's done so many times before, Allie gets up on her feet and turns her back to him. He salivates as she seductively runs her hands up and down thighs, just to turn him on. Her hands disappear under her skirt, only to reappear again between her skin and the elastic waistband of her panties as she slowly slides them down her sissy legs.

"That'll be fine, sissy," he sternly says.

From the tone of his voice, she knows to leave her skirt and blouse on, Alex rarely wants her naked. On this night, her panties are the only article of clothing she'll be removing. He comes up behind her and whispers in her ear. "Has my little sissy been naughty since the last time?"

She knows what words he wants to hear next, "Yes, daddy. I was naughty sometimes."

"You know what happens when you've been naughty, don't you?"

"Yes, daddy."

She lifts her skirt above her waist to expose her bare ass. "I need to be taught a lesson."

"Yes you do," he says and swats her ass.

"Thank you, daddy," his sissy whore says.

He spanks her again and again, while she pretends to cry. She whimpers, "I'm sorry, daddy. I won't do it again."

He's very careful about how hard he hits her. He's thankful he's found someone to play his game and doesn't want her harmed in any way. When he feels like he's spanked her enough, he asks, "Have you learned your lesson, you naughty little sissy?"

"Yes, daddy. I won't be bad anymore. May I serve you your dessert now?"

"Yes, little sissy. Daddy's ready to be served."

Alex always wants a rubber, so she goes to her purse and gets the lube and a condom. His cock has gone down like it always does, so she sucks him again until he's hard. He's in his late fifties and can't hold a hard-on too long anymore. His urge to be abusive always gets released after he's spanked her, and now he's just another horny old guy, wanting to fuck someone.

She lubricates his shaft and rolls the condom down his prick. She squirts some in her hand and rubs it over her ass and lubricates her hole. She stands up, kisses his cheek, and announces, "Dessert is ready to be served, daddy."

She turns around holding her skirt and bends over for him. He likes fucking in this position; they hardly ever fuck on the bed. She lifts her skirt above her waist, he puts his hands on her hips. She guides his cock to the entrance of her hole and waits for him to enter. "C'mon, daddy," she teases, "gimme what every sissy wants."

"I'll give it to you, you sexy little sissy slut!"

He shoves it in all at once, but Allie feels no pain. She's been fucked so many times and can barely feel the below-average size of his cock. But she always squeals for him and acts like it's hurting her; it makes him feel like such a man.

"Oh, daddy, you're so big! Fuck me, daddy, this is what I've wanted all night."

This is Allie's favorite part of the date. All she's really wanted all night is his $300, and she knows he can't fuck very long. While he grunts and groans behind her, thinking he's the world's greatest stud, Allie works her ass to milk him of his load.

Alex breathes hard and fast as Allie milks her date; she's ready for it to be over. "C'mon, daddy," she coaxes, "gimme what I need."

He takes his hands off her hips and grabs onto her pigtails, pulling her head back and fucking as hard as he can.

"Oh, god-damn!" he grunts. "Get ready, sissy, here it comes!"

She knows he's cumming when he pulls her butt close to him, keeping his cock buried in her ass until he spurts his last drop.

"Was that good, daddy...? Was I good enough for you?"

"Oh, darling... it was more than good," he says as he pulls out a bare cock. He doesn't care that the condom is still up her butt. He pays her good money, and she can get the rubber out of her ass herself.

She turns around and gives him a kiss. Sissy time is over.

"I'm glad you liked it, baby."

"Shit, Allie," he tries to catch his breath, "you're so god-damned fun to be with. You know I didn't really mean all that sissy stuff I was telling you, don't you?"

"Of course I do, sweetheart. I like playing your game. I'll be your sissy any time you want."

"It's nice to have a secret playmate," he tells her.

"Your secret is always safe with me."

She takes him in the bathroom to clean him up and sucks his cock a little more before he goes. He can't get it up again, but it makes him think about wanting another date. Allie wants him to remember what she can do with her mouth.

After getting dressed, he pulls an envelope containing her money out of his suit pocket. "Here's a little something to say thanks, darling."

"Thanks, baby. Remember, you can call me anytime you want to play," she gives him a kiss.

Alex doesn't want to be seen leaving the hotel with his whore, so he gives her a hug and says, "Thanks again, sweetstuff. Call me when you close escrow. I'll get your house ready to move in as fast as I can."

With that, they kiss goodbye and Allie's all alone in the room. She gets a joint from her purse and lights it up. Lying on the bed, getting stoned, she thinks back to a year ago and remembers how shitty she always felt after a date, before she met Jill.

She'd lie there feeling all alone and get depressed, sometimes she even cried. All she had to go home to a year ago was her lonely apartment, so empty-feeling and always filthy-dirty because she never ever cleaned it.

She has a smile on her face tonight. She knows Jill's at home waiting for her, and their two wives will be home later. She's happy and stoned when she gets up off the bed.

She sits on the toilet to wipe all the lube off her butt and pulls the used condom out of her ass. She looks at her pigtails in the mirror and thinks of the fun she had when Carla braided her hair. 'I'm so lucky to have a wife like Carla,' she thinks to herself.

She's not all that fond of the way she looks with pigtails, but Alex sure loved them. It's all part of a whore's life, being the girl your john wants you to be. It only took her about an hour from the time they got into the room until she got him off and sent him on his way. Allie's a good whore, and Alex is easy money to a whore like Allie.

She gets her hairbrush and brushes out the pigtails. As her hair gets back to how she likes it, she can't help but notice how pretty she's becoming. A year ago, the mirror showed her a lost and lonely person with tears in her eyes.

Tonight, she sees a beautiful woman smiling back at her, and that beautiful woman is her true self. She almost comes to tears thinking about how beautiful her life has become.

Published 
Written by Jilluvscox
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