Chapter Fourteen

“Hi, I’m here for your 8AM appointment!  You must be Leslie!”

Leslie’s mouth opened and closed wordlessly as a very attractive young woman smiled at him and gently pushed her way through the door and into his apartment.

Leslie tried to hide further behind the door, hiding the feminine lavender workout clothes he was wearing.  Words were not forming and the woman was already inside the room with him.

“Um, there must be uh, right you see, there was a mis…”

“Look at you!  I love that outfit! So cute!”

Her smile went all the way into her eyes and Leslie felt himself blush ten shades of pink as his hands moved to cover the slight bulge that his chastity cage made in his leggings.

“I’m Amy.  I hope you are excited!  I think we can do some great things.”

Leslie tried to shake his head which turned into a nod which turned into a shake again.  The woman was talking so fast and had so much bubbly energy.  Leslie was having a hard time keeping up.  All his panicking brain could think about was how he was dressed.  The tight leggings hugging his legs and ass, the sports bra pushing his fake breasts together, and, of course, the ever-present chastity cage that while tucked away was still prominent through the thin pant material all felt very much on display and exposed.

The woman held up the small pink bag she was holding.

“So… where do we want to do this?  Over here?”

She was already moving into his apartment, looking around.  The pink bag ended up on the counter next to the pile of embarrassing female items that he had still not put away.  He saw her eyes dart to them and then over to his bedroom where the outfit from the previous evening still lay discarded on the floor.

“Can I just say, I think it is just great that you are ready for this next step.  It is very brave and please know I am going to do everything I can to make sure you are happy.”

Oh my god… she’s a prostitute…

The thought suddenly cascaded into his bewildered brain like a tidal wave.

Oh god… this is illegal.  I’m not going to… I can’t…

“Um… I’m not sure what you…”  He was stammering, the words not coming out quickly or correctly.

The woman was already moving towards him, her hand gently grabbing his and leading him towards the middle of the room.

“Don’t worry about anything, sweetie.  You’re not my first, you know.  Here, have a seat.”

She pulled one of the bar stools to the center of the room and before he knew it, Leslie was seated on it.  She circled him even as he tried again to protest.

“Listen, I do not think…”

“You are already super cute, so I think this is going to be easy.  You are going to love this..  It looks like you already showered and washed, so we can just get right to it.

She turned to the counter and rummaged in her pink bag, pulling out a large black piece of plastic.   She swung it in an arc, and Leslie found it drifting down to surround him.  She fastened it around his neck with a piece of velcro before moving back to the counter.

Relief flooded into Leslie to at least have his outfit covered, even as fear and anxiety filled him.

Not a prostitute.  She’s a hairdresser.  Mistress scheduled a hair appointment in my own apartment!

He had to stop this.  He had to…

“So let’s see… what was it you had scheduled?”

His brain had caught up and it was time to put an end to this before things went any further.  The AI Mistress had not said anything since the woman had entered.  Perhaps he was safe to…

Leslie started to stand up.

“Listen…Ms… Ms. Amy… listen… I think…”

Remain seated.  One hour has been added to your time-safe lock.

The voice filled the room coming from the Assistant device, his computer, his phone and his watch.  His eyes flew up to meet the woman who glanced at him with what looked like a smirk.

“What was that?”

He felt all the blood run from his face.  How could he even begin to explain what was happening here.  He felt heat on his cheeks replacing his pallor with a blush, as he sank back into the bar stool.

“Um… I have one of those virtual assistants…”

She laughed, pulling tools out of her bag and setting them along the counter.

“So I gathered.  And a time-lock safe apparently…”

He nodded for lack of a better thing to do.  Her smirk grew bigger and crept up into her eyes.  He looked away, unable to maintain eye contact with the woman.

She knows.  She knows what’s in the safe.  She knows that I’m in chastity.  She must have seen it.  How could she not have these stupid tight leggings?  She probably thinks I’m a pervert.

“Too cute…” she said softly, moving towards him.  Her hand went to the sides of his head, her fingers running through his hair, evaluating and exploring his wet, tangly locks.   Despite himself, he shivered, the pleasure of the touch turning his already over-stimulated body to mush.

“Were you afraid you were going to chicken out and send me away?” she laughed, walking behind him.  Her hands teased the back of his long hair, her nails grazing his neck and sending shivers up his spine.

Leslie always loved haircuts, and always sought out the more attractive and playful hairdressers.  There was something so erotic and also comforting about having feminine hands running through your hair.  This, combined with his overstimulated and caged arousal, was quickly activating his submissiveness.  He did not want her to stop touching him, despite his embarrassment and anxiety over this sudden situation.

“I think that’s really cute.” she said, now using both hands to run through his hair on either side, detangling and pulling it free from the black plastic covering around his neck.  “I think you are very brave for doing this.  I have all the details you requested… and I promise we are going to make you look fabulous, ok?   Trust me.”

Details he requested?  Fabulous?

The words sent a five alarm fire into his brain.  He didn’t want to look fabulous?  What had his Mistress scheduled for him?

“Just relax.  You are very tense.  Would you like to put on some music?  Something relaxing?”

As if on cue, a soft coffee-house guitar music began to play from his TV.  Amy laughed and pointed.

“Good choice.  Looks like you have your whole house under your control.  Must be nice.”

He laughed half-heartedly with a ‘yeah’.

Under my control?  If she only knew…

She was attacking his hair with a comb now, pulling it through and straightening the tangles, her hand periodically grazing his neck and scalp.  It made him all tingly.

“I wish I could get some of that stuff for my house.  My partner is just useless with those things and I just don’t have the patience for the setup.   Did you set it all up yourself, or did you have some help?”

His mind flashed back to his MIstress dictating every step of the automated assistant setup.  He felt himself grow smaller and more timid from the memory.

“I, um… I had some help.”

“Makes sense.  Everything is so complicated these days.  These tech things have a mind of their own.”

Her combing became more aggressive as she worked out the rat nest of long, tangled hair that he seldom brushed out.

“So… is there a big occasion tonight?  Most people don’t get the full package without a reason.  Hot date?”

Full package?  Date?

Beneath the plastic, inside his tightly packaged leggings and cage, he felt his panties dampen.

He needed to stop this.  He was about to get his hair styled and there was no doubt in his mind that it was going to be something feminine and impossible to hide… but his submissive arousal was making it very difficult to actually protest.  He had always fantasized about getting a more feminine hair style, hence why he kept his hair long, but his hair was still a messy man style and not something that looked overly attractive.

How much damage can she do?  I already have long hair, and if she does some kind of layered shit or something I’ll just cut it shorter.

He knew he was rationalizing his aroused desire to have the woman actually do what she was planning.  He might have been able to put a stop to it even, except she was now running her hands through his hair again, as she spritzed water back into his already damp hair.  Her touch caused another squirt into his cage.

“You can close your eyes and relax if you want.  This first part will take a little time.  Looks like eight AM is a little early for you, am I right?”

If she only knew… up past two AM typing punishment lines and then doing an endless beauty routine, only to be jolted awake at 6:30.

He was tired.  He let his eyes close, enjoying her gentle touch and the smell of the perfumed water she was spraying into his hair.

“You have such nice hair.  Just wait until we give it a little TLC.  I think you are going to be amazed at just how…”

Her soft, bubbly voice carried on around him and despite the worry, the anxiety and the aching arousal deep inside of him, he let himself relax and enjoy.