A sissy's first time

I love it when people make requests. I like meeting new people, and I love when I get to build friendships based on those meetings.

I really hope that the person who requested this continues to be as kind as she has so far. And I hope that she likes it, and that you like it. I really hope the pain killers I'm on because of some dental work (the kind of torture you have to pay for but don't enjoy) didn't hurt my writing as much as it hurt my jaw. (I made that dirty. Please feel free to do so yourself).

A Sissy's First Time

Hailey took a careful step, putting her weight very slowly onto her toes. It wasn't impossible to walk in ballet boots, but it required very careful steps. They were just like any other heels. Enough training, and even the pain of wearing them wasn't all that bad.

She dusted the top of the entertainment center and smiled to herself, proud that she could walk so well after only a few weeks of practice. It was the last task she'd had to perform before her mistress would let her out of the cock cage and give her an orgasm. Her first in months. Hailey was looking forward to it, but didn't really think about her cock much anymore. Aside from the fact that it belonged to her mistress rather than to her anymore, Hailey just didn't like being reminded that it was still there. She didn't like being reminded that she had grown up named Harry. She preferred thinking about how shapely her legs were getting wearing those boots. And how soft her skin was. And how nice it was to be hairless. And how important it was that the house be clean.

Mistress would be home in a few minutes. Hailey had to be sure the flat was spotless. She'd mopped, she'd scrubbed on hands and knees, she'd vacuumed, dusted, and swept. All day long, she'd been cleaning every inch, not even breaking to eat. Everything had to be perfect. Mistress deserved nothing less.

Mistress pressed the buzzer when she arrived at home. Not to be let in; she had her own key. She pressed the buzzer to give Hailey the time to toe her way to the front door and take the time to get down on her knees. Hailey adjusted her uniform, wanting to make sure everything was perfect. She checked her hair to make sure that not a strand was out of place, then put her hands behind her back and gripped her heels, pushing out what little chest she had.

The door opened. Hailey watched her mistress take the first steps into their flat. Hailey looked at the soft leather of mistress's boots as the hugged the curves of her leg up and just barely over her knees. Hailey let her eyes travel up the thigh high stockings under the boots, but stopped as soon as she hit skin. She knew better.

Her mistress stood in the entryway, one foot pointed at Hailey, the other off to the side. She tapped her foot, clearly impatient for something. Hailey risked a look up at the disapproving face of her wonderful mistress.

“Did you make it dirtier in here, you stupid cow?”

Hailey shook her head, but didn't say a word.

“It looks atrocious.” Her mistress took out a white glove and slid it onto her hand. “Stay where you are,” she said. “Just like that.”

Hailey waited, listening to the sound of her mistress inspecting the flat. It was spotless. Hailey knew that. But she also knew that her mistress would find even the smallest bit of dust and would insist that Hailey had failed. That she was as useless as a woman as she had been when she was pretending to be a man. Then she'd punish Hailey.

And only later, when her duties for the day were complete and it was time for her to go to bed unsatisfied yet again, would mistress tell her that she had done well.

A few minutes passed, and her mistress came to a stop behind her.

“I don't know how you did it,” she said. “But somehow you managed to not disappoint me. For once.” Then she put something around Hailey's eyes, blocking off her sight. “Good job.”

“Thank you mistress.”

Her mistress helped Hailey up to her feet, then guided her into the den. Put her in a chair.

“My slave is coming over,” her mistress said. “Did I tell you about my slave?”

“Yes mistress.”

She hadn't though. Hailey knew that mistress had a slave, and that she and the slave had drifted apart before mistress met Hailey. She knew that the slave and her mistress had started talking again. But that's all she knew. Mistress always called the slave it, and never spoke of any kind of personality. All she would tell Hailey was that the slave did everything it was told. Always.

“Hands behind the chair.”

Hailey put her hands behind the chair, felt mistress lock the cuffs in place.

“Open your legs, sissy.”

Hailey spread her legs, and mistress tied the heels of Hailey's boots to the legs of the chair. Her legs ached from the ballet boots, but she didn't make a noise. She was not permitted.

The bell rang again, and Hailey heard her mistress walk to the front door and let the slave in. Then Hailey felt her mistress unlock the chastity cage and pull her little boy-clit free. The sound of her mistress walking away, the click of the boots against the floor, instantly had her erect.

Mistress laughed at her.

There was a knock at the door. Hailey heard her mistress open the door. Then she heard the familiar sound of skin hitting skin.

“Don't speak to me, you filthy shit,” her mistress said. “You should be on your knees and already naked. Why are you still dressed, you disgusting waste of life?”

There was another slap, harder this time. Then Hailey heard clothing hitting the floor. Her mistress slapped the slave several more times, imploring the slave to strip faster, to try to remember what it was like to obey. To learn its place.

Hailey pulled against the handcuffs when she heard her mistress say “No, get to boot licking, you slut.”

Those boots mistress wore were not meant for the tongue of just any slave. Those boots were there for Hailey to worship, for Hailey to use as a demonstration of her devotion to her mistress. She almost said something, almost complained.

Then she felt pressure on her foot. It was gentle, moving up her leg. It took Hailey a few moments to realize what was going on. Mistress hadn't ordered the slave to lick her boots. The slave was licking Hailey's boots.

Hailey, tied to the chair, was getting her boots serviced by a nameless slave.

She tilted her head back, trying to see out under the blindfold, but there was no gap. She tried to listen to the slave, see what she could figure out that way. But there was nothing. There was just the slight pressure of the slave's tongue as it moved up and down her feet, of the lips kissing her boots.

Hailey whimpered and groaned, uncomfortable with how turned on she was getting.

There was another slapping sound, and Hailey flinched out of habit. But she hadn't been hit. “That's enough with the boots, slave.” The pressure of the tongue suddenly stopped. Then Hailey heard mistress snap her fingers, and the tongue came back.

Quite a bit farther up.

The slave's tongue slide along the length of Hailey's already straining cock. The soft, warm, wet feeling dragged a moan out of Hailey's mouth. She let her head fall back as the slave's lips wrapped around the tip of her cock, and let out a very long, very satisfied groan as she felt the slave's mouth slide down around her aching, neglected cock.

Her eyes were closed when her mistress pulled the blindfold off. Hailey was too busy trying to enjoy the blow job, her first in what seemed like ages. She pulled against the handcuffs, wanting to grab the slave by her hair, wanting to run her hands over the slave's scalp.

She bit her lip, moaned, and opened her eyes.

The slave looked up at her with wide eyes.

 

He looked up at her.

Hailey flinched and tried to pull away. The slave instantly stopped, looking up and over Hailey's shoulder, at her mistress. The slave looked up, but did not take his lips off Hailey's cock. He just knelt there wearing suspenders and stockings, his own erection pushing against the frilly panties he was wearing. He knelt there, Hailey's cock in his mouth, and waited.

Mistress put her hand on Hailey's shoulder.

“It's up to you, darling,” she said. “You know that the slave is a good cock sucker. He's got a lot of practice. If you let him, he will suck you to the best orgasm you've ever had.” Her voice then grew cold. “And if it's not the best orgasm you've ever had, then you will get to join me in turning the slave's skin into one massive bruise.” The slave nodded at the threat, but did not go back to sucking.

“Mistress, I-- I don't know if I can do this.”

Hailey felt her mistress's hands on her shoulders. “It's okay, doll,” she said. “If you don't want him to finish, just tell him to stop. Tell him to take his lips off your cock. Tell him you're not a faggot, and that if he is so desperate to suck cock, he needs to go elsewhere. Just say that, and he'll stop. He'll even apologize to you.”

Hailey opened her mouth, then closed it. She looked up at her mistress. “And then what?”

Her mistress shrugged. “Then nothing. You just stay there, just like that, in the chair. I use my slave to my satisfaction, then he goes home.” She bent low to whisper in Hailey's ear. “And I put the cage back on.” She kissed Hailey's ear. “Maybe I'll give the key to the slave here, so you have to ask him for it.”

Hailey whimpered, more so when her mistress giggled. Hailey knew that giggle. It wasn't an idle threat. And it wouldn't be just a matter of a phone call to get the key.

Hailey looked down. She was still hard, and his lips were still warm and soft against her cock. He flicked his tongue against the head of her cock and looked up at her with mischief in his eyes. Hailey bit her lip.

“And if I can do it?”

“Then just tell him to do it,” she said. “Tell a man to suck your cock. Make sure he knows exactly what he's supposed to do.”

“Will I have to return the favor?”

Her mistress laughed. “Would you like that, my little sissy?”

Hailey didn't answer. But then, she didn't really have to.

Her mistress laughed again. “Tell him to suck,” she said. “Tell the slave to take your cock into his throat, to suck you to orgasm, and to make you cum. Tell that man down there between your legs to slurp on your cock and give you the best orgasm you've ever had.”

Hailey bit her lip. The slave flicked his tongue again.

She let out a soft moan.

“Do it,” her mistress said. “If you didn't want to do it, you wouldn't still be hard. Tell him to serve you. Tell the slave to suck your cock.”

Hailey took a deep breath, closed her eyes for a moment, and then opened them to lock gazes with the slave.

“Go,” she said.

Her mistress laughed.

“That's not good enough, Hailey. Tell him exactly what to do.”

Hailey nodded and gathered her courage. “Suck my cock,” she said. She cleared her throat and put more force into her words. “Suck my cock you cum guzzling slave whore.”

Her mistress applauded. The slave went back to sucking.

Hailey moaned and closed her eyes. Her mistress whispered in her ear. “I'm very proud of you,” she said. “And we're just getting started.”