Meeting My Mistress Chapter 49

9:10 am, the elevator opens, and in walks Shane. His septum piercing is tucked in his nose. he removed his earrings . He's clean-shaven. He's wearing cheap single-breasted 3-button black suit with a blue tie, not a clip-on. Points for him on that.

Dress shoes are also cheap but shined to mirror finish. He has a briefcase. I am actually impressed. I pick up the phone he's here, I say.

Thank you, said Becky, and the phone clicked.

Morning Shane, you early!

My father always said if you're not 15 minutes early you're late.

Can I get you a coffee?

No, thank you, Brianna. I am fine. He stands up.

The bathroom is the third door on the right. I said.

Thanks, he said.

I see he's nervous. He's back in under 5 minutes.

Bree if I may ask? Anything I should know before going in? I really need this job.

Since you asked. Address her as Ms Stapleton, Ma'am for short yes or no answers. Don't slouch standing or sitting. Wait to be invited to have a seat. When summoned to go in, knock twice, no more, no less. Above all do not lie! She's an attorney. You're only here because she checked you out thoroughly and she liked what she read about you. Keep your answers short and on point.

Yes Ma'am he says.

I am rooting for you Shane. The rest is up to you now.

Thanks, Brianna. He must read my nameplate. Smart kid I think to myself.

9:30 am on the dot buzz

Yes, Ms Stapleton?

Let's have him she said.

Right away Ma'am.

You're on, Shane. Good luck!

Thank you, Ma'am. Knock, knock.

Come in! Shane, nice to see you close the door, please.

Who's he asked Terri?

Hopefully, the person that will take your phone duties.

A male receptionist?

Why not? We have male nurses and waiters, so why not?

Okay, just always thought she'd hire a woman.

She did! You and I! We laughed softly.

30 minutes go by, then 45 minutes, then an hour. They walk out together all smiles.

Bree, Terri, this Shane is going to be my new assistant.

Bree, would you please give Shane a brief tour? Terri, please Check on Cathy. Make sure she has everything she needs. If she needs anything please let me know.

Ms Stapleton. She needs a new chair, I said. Really?.

Yes, I saw the shape it was in. Do you have anything else?

An extra bookshelf I noticed the office was missing one.

Okay! Ladies! Get to it!

Yes, Ma'am, Terri and I say in unison.

Shane, follow me, I said.

Yes Ma'am he said. I smiled.

Bree?

Yes, Shane?

Thank you. I did everything you said. She really knows everything doesn't she?

Yes, she does. She's very ethical Shane. Honesty and loyalty are priority one, to her. If you need something talk to her. Someone approaches you and asks too many questions. Stay quiet and let her know. Our work here is to defend our clients.
It isn't anyone's business except the client and attorney, not even ours.

I understand Bree.

As an assistant/receptionist, our job is to keep her in communication with clients, attorneys, staff, and other resources.

Here's the kitchen. Make sure you mark your lunch and food. If you want to eat out there is a sandwich shop across the street. The coffee shop next store makes a great cappuccino.

Have you ever answered phones, taken messages, or done research?

A little in college, I was my instructor's student aid.

As an assistant, we arrive early and don't leave until she does unless she sends you somewhere.

Any more advice Bree?

Clothes, you have to get some better clothes. Until then make sure you keep your current stuff cleaned and pressed. Don't wear the same thing twice.

Got it! Said Shane.

How are your computer skills, Shane? Pretty good, I am Comp TIA A+ certified and am Certified in Microsoft Office365.

That's great, how's your typing?

40-50 words a minute. That's a solid number. Everything here is handled electronically and is backed up daily, and also printed and filed.

Any incoming papers, receipts, and reports are all filed, scanned, and backed up as well. Whenever there is a lull in calls, start scanning, file, and back things up.

You do not want to fall behind on it or you'll be coming in early just to catch up. Ms Stapleton hates large piles. If it piles up quickly, ask Terri or myself, and we'll cover phones for you.

Thank you, Bree.

Bree, will I meet everyone here?

In time right now I want you to meet two of our junior partners. They answer directly to Ms Stapleton.

Judy, this is Shane Weaver Ms Stapleton's new assistant.

Nice to meet you, Shane. It's very nice to meet you.

Judy, can you call Cathy over?

Sure Bree.

Cathy, can you come to my office for a minute? Okay, thanks.

She's coming.

Yes Judy?

Come in. Cathy, this is Shane Weaver Ms Stapleton's new assistant.

Welcome, Shane; Cathy extends a limp hand, and Shane shakes it softly.

Nice t, to meet you, Cathy. Shane stutters a bit Greeting Cathy.

You have soft hands, Shane.

Thank you.

Your nails would benefit from a good manicure.

Thank you, Cathy.

Judy and Cathy here both answer directly to Ms. Stapleton or when Ms. Elgin is on-site as well. You will be seeing them often so I thought it best to introduce you officially.

Cathy, are you settling in okay?

Yes, Bree, Terri has my desktop almost set up already, and the printer is next. He said my laptop will be ready tomorrow. My smartphone next week. That's great.

Terri is fast said, Cathy.

Yes, she is. Terri is off next week and the following week, so if you need something tech-related, just ask me.

Will do Bree, said Cathy.

I have tech support experience too said Shane.

Impressive I said. Ladies thank you for your time,
Shane and I need to finish his orientation.

Thank you, Bree, Shane they say in unison. I see Shane blushing a bit.

Shane you alright?

Yes, I'm just a bit overwhelmed, is all. I understand honey.

What does that mean, Bree?

Shane! If you haven't guessed it by now, I'm trans. Which means I understand and see more than 90% of other people.

Two successful, beautiful women in positions of leadership and power. They greet you with friendship, kindness,, and a bit of respect.

You were intimidated. It's okay to feel that way; I get it and understand it, too.

How could you possibly know what I'm thinking?

Shane, I read people, it's what I do.

What am I thinking now? You're thinking you still want this job to grow your future, but you're scared it may be too much. You want this future, but you're scared of all the paths you have to travel down or what you may have to sacrifice.

Bree, are you psychic?

No, like I said I read people.

Shane, I can read you like a book!

Bree are you really Trans?

Yes, and Ms Stapleton is my spouse. Terri is at the beginning of her transition and is my niece. The other senior partner is Carol Elgin, she's my sister and Terri's mother.

Like I said before this is a very ethical law firm. We defend veterans, first responders, police, abused spouses, divorce, as well as selected criminal defense.

We aren't defending corporations or organized crime here. We defend a lot of little people and some big ones. The big case helps us to help us with the little cases. Stay honest, stay loyal, do as you're told and the benefits will allow your dreams to come true.

My dreams?

Yes, your dreams!

I doubt that, said Shane.

Try me I said. You'll fire me if I tell you.

Unless you concealed a criminal past I won't have you fired.

Okay, here it is, oh my gosh, I can't believe I'm saying this; I hardly know you. I'm bisexual and a crossdresser. There I said It.

Oh my gosh! Shane starts breathing hard!

Easy, sweetheart, relax. I stroke the side of his face with the back of my fingers, like a mother to a child. It's alright, Sharon, relax, you're safe with us.

We will protect and nurture you. Sharon, are you alright?

How did you know Brianna? Seriously, how did you do all this? Were you stalking me?

No! Of course not. Sweetie I've been crossdressing for over 30 years.

As they say, it takes one to know one. Now here's a question. How far do you want to go?

I don't know, honestly; I love wearing women's clothes more than men. Well, if you want to dress like a woman, you'll need to look the part.

Are you into men or women?

I like a powerful woman, a dominant woman with a loving touch.

Would you be willing to become her sissy?

Yes, oh gosh, Shane tears up. You think I'm a freak now.

No, sweetie, I think you're perfect.

What? What's that mean?

Remember meeting Becky and I for the first time?

Sure, when you two smiled at me, it felt like my heart came alive.

I read you then. Ms Stapleton didn't believe me at first. But I tested you then, and you passed. We checked you out, you passed, you were interviewed and you passed again. It was by pure chance we found you.

Now here you are. Are you ready for your dreams to come true?

Yes, but I'm scared. Don't be, you will be tested over and over. You can quit anytime you want. No one here will blackmail you. You have free will. I have to warn you. This sissy lifestyle is erotic, fun, and is more addictive than any drug.

It's also hard work and discipline. You must submit to it by your own free will. No one will force things on you. You must agree to everything to move forward.

How will I live, where? I can't stay at my apartment.

Worry about living conditions later.

Bree, I don't know, it's, I mean, my head, it's all so much so fast!

I know baby! I know, trust me I was in your shoes 8 months ago. Terri only 3 weeks!

Terri, three weeks?

Yes, Terri took to it like a duck to water.

What will Ms Stapleton think?

She'll love you as Sharon! How do you know that name?

I guessed, but being a fellow crossdresser, it wasn't hard.

You really can read me?

Yes, I can. This is why I know you're thinking you have no women's work attire and need a serious shopping trip and makeover. And you're seriously broke and need to figure out how to pay for it.

Are you sure you're not psychic?

Pretty sure. Leave the rest to me, provided you still want to work here and submit to dressing as a woman daily, that 365, 24/7.

Yes, Bree, I want to try.

Do or do not there is no try!

Yes, Master Yoda! said Shane.

We giggled.

You have a sense of humor and a Star Wars fan! I knew I liked you! Let's get to work. I said.

I spent the next hour going over the phone and computer system. Shane picked up on things quickly. He used Microsoft Word pad for phone messages and would forward them through our in-house TEAMS to me and Ms Stapleton.

By 11:30 am he was smiling as he answered phones with music in his voice. I watched as he worked with diligence and care. He had a can-do attitude.

Treating this job as a new career, a second chance. I gotta say it was much more than I had hoped for. I just hope he and Mary hit it off.

I just hope Becky is on board for a shopping, and makeover trip. I called Alice as a precursor to see if she and Sara would be available for a Sunday makeover off hours.

I told Alice everything. She said it sounded fun and great practice for Sara. I told her I had to get permission first and call back...

Terri left before noon with Cathy's new car. Cathy and Becky went to the DA office together.

I started calling Shane and Sharon more often. We were having fun giggling and working. When no one was around we ate lunch at our desks.

My Cell buzzed; there was a picture of Cathy, Becky, and Judy standing in front of Cathy's new A-4.

Terri texted me, She's In!

It was almost 2:30 pm when they came back. All three ladies are smiling.

Ms Stapleton, may I have a minute?

Of course Bree.

Hold down the fort Shane. I'll be right back. I walk into her office and close the door.

How's our prodigy?

Sharon is doing well check your email and team accounts. Very nice, you teach her that? No, she did it on her own.

Wait a second, you said Sharon, and she!

Yes, Ma'am,, I did. Are you telling me you were right about him/her?

Yes Ma'am.

Okay Bree, lay it out?

She's broke, she wants to dress as a professional woman here at work!

And?

Judy and Cathy took a shine to her. Cathy said she has soft hands and needs a manicure.

Go on?

She's a submissive sissy crossdresser. I think she'll be perfect for Mary.

Have you said anything to her?

I told her about us and Terri and I. I mentioned that if she wanted this, it was going to be 24/7, and she had to consent of her own free will.

I told her Carol was my sister and Terri's mother. She wants this job badly. She is afraid of dressing like a girl where she currently lives.

Well, moving with Mary will solve that.

Yes Ma'am. I told her to stay honest and loyal to the firm, and we'll protect her.

How'd you get her to open up so quickly?

I read her and told her. She never denied any of it.

Really?

Yes Ma'am.

She opened up to me. Sharon is bisexual but prefers dominant women.

Gee, I wonder who that sounds like, Becky said.

We giggled.

Okay, Bree, I'll roll the dice on her.

No car for her. Mary will have to supply her with a car and play wardrobe.

I'll fund the usual Salon services and office attire.

What about chastity?

That's Mary's department. A PA piercing is mandatory.

After Terri heals up, I want Sharon's tongue double frog eye pierced amongst the usual. Double naval is also mandatory.

What makeup and breast forms?

Yes, those, too!

Corsets?

Mandatory at work. She wants this, I'll foot the bill but it's my way or highway?

Tattoo makeup?

Yes, on the first visit to the salon. If she wants to start down this path, it's forever.

I expect a return on my investment. If she says no she's out!

I will let her know. When should I start her on the path?

Tomorrow 9 am at the salon. She needs to be ready for work on Monday.

Carol and I need to be at the spa for Terri.

Sharon will be yours to tutor at the start. I expect her to be fully feminine when you introduce her to Mary.

Yes Ma'am.

Oh, and Bree, I don't mind her getting high-end clothes and the like, but stay away from the expensive shoes for her for now, two nice pairs.

What about makeup. Take her to Tia. I want Sharon ultra-convincing. Yes Ma'am.

Did you explain free will?

Yes, Ma'am,, she understands.
Good, I expect total commitment nothing less.

Understood Mistress!

Good girl. Now get Terri to cover phones and take Sharon for a coffee across the street and inform the new our plan.

Yes Ma'am.

Terri, yes, can you come to my desk? Be there in ten minutes she said.

Thanks.

Sharon?

Yes, Bree?

Terri is gonna take the phones for a bit. Let's go across the street. I'll buy you coffee.

Yes Ma'am.

Thanks for covering us. No problem, Aunt Bree.

How was Lunch?

We had a great time. Good, I'm glad to hear it.

We'll be back in an hour. We haven't had lunch yet.

Sounds good, I got it.

Be back soon.

Shane and I ride down the elevator.

Shane, it's okay. You're going to be fine, trust me. I hold his hand as we walk through the parking garage to the coffee shop. I get a reduced-cal frozen mocha with a triple shot of espresso,

Shane gets frozen caramel with triple espresso.

It's hot out here he says.

Yes, it.

Bree, will I become as pretty as you?

Darling, you're a lot younger. Yes, you'll be much prettier than me.

I can speak freely?

Please, Shane, share away.
I want to look similar to you. That coat dress is sexy, powerful, and just plain neck-breaking hot!

Thank you I said.

Shane, I talked to Ms Stapleton just now. She will support the beginning of your transition provided some conditions.

You must quit any other job you currently have. A 10-year commitment to the firm. If you're fired for cause you have to pay everything back. You will be employed full-time, benefits package the works.

Committing today means a bump in pay as well to $ 800 a week, not including overtime, which is almost always. Tomorrow I will pick you up and take you to our Salon. You will be waxed, pierced, and tattooed on makeup as required by my Mistress.

Your hair will be cut, colored, and styled as feminine as possible. Full set of gel nails and pedicure to match. Then on to Nordstroms for clothes and shoes.

We will stop at the foundation store, and while there, you'll be fitted with glued-on breasts and fitted with several corsets. Another stop at Victoria's Secret for undergarments and panties.

From tomorrow on, male clothes will no longer be an option for you. Is this something you really want to do?

Bree, can I have a minute? Please!

Shane gets up and heads to the bathroom. He's in there for almost 10 minutes. He comes out.

I know this is a lot to grasp Shane. But it's a one-time offer to embrace your dreams.

Bree, I know my family will hate me for this, but I'm so miserable in my current life. Bree are you happy?

Yes very happy and much healthier than I've been. I probably shouldn't tell you this. But without details, my sex life is outstanding.

Will I be as happy?

That's up to you Shane. You must say yes to commit, here, now.

I can promise I will help in any way I can.

Will I be serving a Mistress?

Yes, Mistress Mary, we will meet her soon. If all goes well you'll be moving in with her.

Is she pretty?

Very pretty, and sexy. She will enslave and train you to be her sissy when not at work. You'll be her maid live-in sex toy, and lover. She will care for you as you will her.

A Mistress/sissy relationship is a deep bond of trust and commitment, Shane. Far deeper than marriage. It's a loving relationship on an entirely new level.

I know you were drawn in by Ms Stapleton's powerful presence.

Yes, I was.

Good, Mary is just as powerful. I think she'll love you.

You do?

Yes, Shane, I do! Mary wants a committed relationship with a sissy. Spoil her with loyalty and obedience and your rewards will be endless.

One more thing, how do you feel about chastity?

What's chastity?

Oh, you sweet, sweet boy. Chastity is where your penis is secured by a cage locked around the back of your balls.

You mean?

Yes, your cock will be locked up.

After a year on HRT, it will be limp, and your balls will shrink.

Really?

Yes.

Are you in chastity?

I was. Now I tuck. My penis is off-limits to me.

How do you have sex?

Anal, oral. I am very good at oral.

Really?

Yes! I want to show you something, don't freak out. I stick out my split tongue, pierced stud on each side. I clap my tongue and move my tongue over and under with it.

Shane gasps quietly, Bre that's so so

Freaky? I ask?

No, sexy I want one.

You need to know what you're getting into Shane. No one will force you.

But once you say yes, you sign papers for legal consent. We will be bound together. Do you have any girl clothes, Shane?

Jeans, a couple of skirts, blouses, and some lingerie.

Can I have another minute? Shane asks.

Sure but we have to go back in 20 minutes. Shane goes to the men's room again. 5 minutes later. He sits down.

Bree, I gotta ask. This is a real offer, no bullshit. I am not gonna be shipped off somewhere?

No hell no! None of that! You'll meet many of my friends tomorrow, including Sara. Maybe even my friend Amber. They're both full-time sissies.

They have jobs they work and have a life. You will too. The only thing different is you'll be feminized and live a far different domestic life than the vanilla crowd.

Okay, Bree, I'm in on one condition.

What's that? To maintain contact with my Aunt my mother's sister. She's really the only family I have left.

Of course. I still maintain full contact with mine.

Good, I'm in. Let's do this said Shane, smiling.