Urban

Meeting my Mistress Chapter 16

Added 2024-11-19 13:38:45 +0000 UTC

I go back to my data entry. Lunchtime is actually the perfect time to put a dent in it. I only answered one other call until almost 2 p.m. Judy was gone for almost 90 minutes. Rick was told to monitor our surveillance whenever he could, including during lunchtime.

I found out later that Rick started changing cars in parking garages. Clever man.

On the other side of town, Alex is having the time of her life with her new man. Keith was getting the full landscaping treatments. Haircut, full body wax, eyebrow wax, and facial wax. Alexis topped him off with a mani-pedi.

Keith was so taken with her he had his ears pierced twice in each lobe and his belly button pierced. He did say no to tongue and nipples this time.

From all I heard, she gave him a 3-hour massage and moisturizer treatment. According to reports, Keith is 12" with a 5-incheter nightstick. Still, the gentleman was strong enough to say no to Alexis, for now.

This is impressive to us and solidifies our trust in the firm's newest employee. He behaved, but he also never turned down a kiss from her. After his treatments, Alexis took him shopping.

Keith had no clue when it came to the finer points of men's fashion. Alexis gave him a crash course. Versace, Tom Ford, Louis Vuitton, and Prada. Fortunately for Keith, Alexis being a Coven member means tailoring the same day.

By the time they finished with casuals and shoe shopping, six single-breast suits were done red to hide his Glock 40 and look like a high-operative.

Without realizing it, Alexis got her first wish. Keith asked her to dinner that night. She said yes. She took Keith back to her condo. He stayed in a living room while she changed. On Mistress Becky's advice, he took her to Spago's.

She returned him to Mistress Becky's at 9 pm. Keith reported no tails on them. She stayed for a cup of coffee and returned home. As she left, she kissed him goodnight. She melted in his huge arms, and her left leg went up parallel to the floor. She was in love. I am so happy for them.

My day was lots of data entry. We worked until after 6 pm. Judy left at 5 pm. I told her I'd meet her at 7:30 am. I wanted to be first at the mall. We had appointments at the salon at 11 a.m. I am so hungry. I took my vitamins and had iced tea.

While Ian prepared dinner. I was tired and needed my energy for tomorrow. I asked if I could be excused for the night, and Mistress said yes. Ian handed me a sugar-free sports drink and said drink it before you fall asleep. You'll feel and sleep better.

Thank you, Ian. I smile and wink at him. I kiss Mistress and Carol on the cheek. Upstairs, I go through my usual routine: enema, shower, and moisturize. I put on my bright yellow baby doll nightie. It's just after 8:30 when I finish the sports drink. I set the alarm for 5:45 am.

5:44 am and I'm up I click the alarm at the first chime. Enema, shower, moisturizer, and then my door opens. Mistress Becky walks in. She's wearing a sheer pink baby doll nightie that leaves almost nothing hidden. I only had on my hot pink satin thong pants.

She said lay on the bed, sissy. I lay on the bed. She unlocks my chastity and removes my plug.

Mistress?

You're not in trouble, my sweet sissy. You're going to be shopping today on your own for the first time. You need to be comfortable as well as fashionable. The clothes also need to be easy to take on and off.

My curls were almost gone again. Let's get you ready, baby girl. I put on my satin hot pink Hard Cup T-shirt bra. Mistress pulls out my white chemise and T-shirt. My pink leather miniskirt and matching leather mini jacket. I start stripping my nails.

I then do a soft pink and silver/gray smokey eye. I do a hot pink ombre lip color. When I finish, I walk out to my bedroom; my wife has everything ready. White stockings and garter belt, and hot pink leather mini boots with 4" heels.

After I put on my stocking and garter belt, my wife says spin sissy. I spin slowly and curtsey to her. She smiles and says, I am so proud of you. You make me so happy. You make me very happy too, my wife. I love you so much. We blow kisses at one another.

She begins to dress me. She tapes my clitty back while still allowing me to pee. She pulls up my skirt and zips it up. Then I put on my T-shirt and jacket. She then puts my boots on and zips up the back of the boots.

I stand up and spin for her. She smiles that pleasing smile I long for. She stands; we ai and r kiss. Let His hair square away. She Shes the curling iron and adds life to my curls. They put my hair in a high ponytail and fluff it out.

She walks me to my full length. My jaw drops. I look like all the sexy women in the mall I always envied.

You like she asks?

Like? I love it. Thank you, my wife.

She grabs my hot pink purse. We transfer my items. She says wait one minute. She comes back with a Visa gold card and $500 in cash.

Have fun, honey, Spoil Judy today. If you want to get another piercing for yourself, go ahead and enjoy. Judy pays for nothing except any CL clothes. Any office-style formal or cocktail dress is on me, including shoes.

It's important to remember she has to willingly choose the items. The salon is all taken care of. Just tip our girls, but I know you already know that.

Yes, my life, and thank you again for everything. It's a pleasure, my love. Now go! Have fun, be careful, and call me from time to time.

I smile and nod. I walk downstairs, and Ian and Keith are up. Already drinking coffee and talking as men do. As I enter, I hear Ian's wolf whistle.

I blush. Wow! You look great, said Ian, and so adorable when you blush. I spin for them, then curtsey. Keith says you are so cute; I see what you mean now, Ian.

Bree here is an energy drink. It's a 50 mix of coffee and tea. It's iced down. He put it in a tumbler with a straw, so thoughtful.

Thank you. I said it has some sugar for carbs. You can have solid food after 1 pm, but just a little. I have a special dinner planned for tonight.

Thank you, Ian. I gotta run, guys. See you tonight. I jump in my red Audi A-4. Gosh, I love this car. I get to the gate. Pull out, and I'm off. Traffic is light as I head to pick up Judy.

No tail today. It would be hard to follow with so little traffic. As I pull up, Judy is dressed in skin-tight jeans with black 3" heels, a pink T-shirt, and a black leather jacket. She jumps in.

I say, Hey girlfriend!

Hey Bree!

You ready?

Gosh, yes, I am so excited. Where are we going first?

To my mall, honey. I have a plan; you trust me?

Yes, Bree.

Okay girl, let's rock this!.

When we arrive at the mall, I use the valet parking; Steve is working.

Hi Steve!

Bree, right?

Yes, Steve. Good to see you again.

This is my friend Judy.

Hi Steve

Hello.

Will you and your crew keep a close eye on it for me?

You know we will!

How many are in your crew today?

5 with me. Shift change?

Not until 2 pm.

Excellent. Parking is $25; I flip him a $50. Thanks, honey, I say.

Yes, ma'am, with a big smile. I take her to NordsNordstromt. I ask for a private shopper. We get a very classy black woman dressed to the nines in a high-fashion blazer dress" with black heels.

I am Ann. How can I help you, ladies, today?

Hi Ann, I am Bree, and this is Judy. We need some high-fashion business outfits for Judy and some evening dresses, maybe a cocktail dress too. She will also need full accessories to go with it all. By the way, I love your Blazer dress!

Thank you, she says.

Ann walks us over to the Versace section first.

Judy looked at the price and said, Gosh, no, Bree, I can't!

Yes, you can! I am under strict instructions and a new professional look for you.

But, this is too much!

Not from where I stand. You said you'd trust me, yes?

Yes...

Okay then, Ann, will you pick out a couple of blazer dresses similar to yours, a couple of coat dressdressesle breasted, some skirt suits, preferably pencil skirts, and some matching slacks that match the skirts?

Right away Bree.

As Judy and I go through the clothes in front of her, she says,

Bree, what's going on?

What?

I thought we were getting me a dress for tonight.

We are. When I told Ms. Stapleton about taking you shopping for a dress, she decided since she's got you overloaded with this case she thought it would be an opportunity for you to sit in the 3rd seat.

3rd seat?

Well, rumor has it. You just passed the bar. Is it true?

Well, yes, it's true, but I never told anyone.

Did you go to Stanford?

Yes, nights and online. Well, I think your reception career is coming to an end.

How did she find out? She has connections everywhere. Judy, you know this. Consider this a clothing allotment for a promotion that's on the way. Besides, as a new lawyer, you need to look the part.

Bree, you look the part, and you're not a lawyer. I am also married to a lawyer.

Ms Stapleton?

Yes, Judy.

She's gay?

No, she's not gay. I am a pre-op transgender.

How did you meet? Online if you can believe it. It's a long story. Carol is my sister.

Ms Elgin? Yes, so that means Terry...

Yes, Judy is my nephew. Judy, I consider you my friend. So I am trusting you with this information.

Ann returns with two rolling racks. Judy, you're a size 4, yes?

Yes, how', how do you know? You have a special mind. She takes us to the bridal changing room. I thought this would be more comfortable.

Would you ladies like something to drink? Water for me, I say.

Judy? Water for me too, please.

Ann sent for a counter girl to get us our water. Judy started trying on outfits. The first outfit is a Blazer dress. I love the cut. Ann says I do too, but I don't like the way it hangs.

I see it too, I say.

Judy says, but I love it.

Ann says, Wait here, ladies. She picks up the phone at the desk and starts talking; we can't hear everything. We hear thanks, Tina.

Ann takes Judy into the dressing room with a measuring tape. Ann measures Judy. Ann and Judy walk out of the dressing room, and here comes a girl from the lingerie department with an armload of bras.

What's up, Ann? I asked

Judy's bust size is between B and C cups. Bali has some new bras that are comfortable and shape your bust to a full C cup.

Thank you, Tina! Anne said to her.

Bree, will you excuse us while I fit Judy? I just smiled and nodded. Less than 10 minutes go by, and Ann leads out Judy in the same blazer dress. My chin drops, and my eyes widen as I soak up her form.

Well? Judy says, What do you think?

Stunning Judy! OMG girl!

Ann, what did you do? I asked.

Very shapely! She's all women now! Anne said with an approving smile.

She was wearing a Large A Cupra. When I measured her, it confirmed my guess that she was B and C cup. The cup's right bra makes all the difference between her body and those legs; it's a complete transformation.

I'll say! Judy, I'd kill for a figure like yours. So would I say, Ann?

Judy went from a slight slouch and was always a bit trimmed. To a bright-faced, glowing woman. Very statuesque and with a newfound confidence.

All of a sudden, Judy's mild fun turned into excitement. Ann says, Would you be interested in a bikini, Judy?

Yes, please, she said.

Colors?

Pink, yellow, or purple, please; maybe a red?

You girls keep trying on clothes; I will be right back.

We ended up trying on 3 Blazer dresses, and Judy was putting on a coat dress when Ann came back. She had at least a dozen bikini sets with her. All of them had support similar to her new bras.

Ann even thought to bring two sports bras. It's after 9:15 am, and the store traffic is picking up outside the bridal room. We are almost all the way through the racks of clothes Ann brought over to begin with.

Between almost a dozen bras and the dresses and skirt suits. Judy added 4 pairs of slacks to multiple suits and dresses. At 9:30 am, we head over to the shoe department.

Ann has to be one of the best personal shoppers ever. She has proper styles, colors, shoes, boots, and even wedge sandals for the 3 bikinis Judy picked out.

One pair of brown and black knee-high 4heeled boots. Several pairs of high-heeled shoes peep toes, open toes, and pointed. Most with hidden platforms. She tried them all on for size. Ann only had to swap out two pairs out of at least a dozen shoes.

9:45 am We are on the way to cocktail dresses. We searched Nordstrom's, but nothing appealed to her or me. Ann checked us out. I handed her the card from the law firm.

Does Ann say you girls work for Ms. Stapleton?

Yes, we say in unison. As she totals up the purchase, Judy's jaw drops; it's over $5,000, then Ann applies a discount, which comes out to a little over $3000.

There's a tip line; I wrote in for $300. Ann says there's a custom dress shop across from the mall called Calls Formals. She has a great selection and can do the next-day rations.

Thanks, we said.

We still had time before our spa appointment. Ann helps us load up my car. Steve is so sweet he brings it up and helps load everything. Judy is wearing the new bras.

Steve asks Judy, Did you get your hair done?

Clearly, he was checking her form. He was being as casual as he could; it was cute. Judy loved it. She caught him once and winked at Steve. He blushed.

We finished loading up the car. I asked Steve to keep it close, and I winked at him. I asked him quietly about any interest in the car.

He smiled and said not so far.

Thanks, sweetie. I said.

We walk back into the mall. We head to Macy's. You need an LBD and an LRD, Judy. (Little Black Dress, Little Red Dress). Maybe a sheath dress too. I love mine. We walk past all the designers straight to my favorite designer, Donna Karan (DKNY). No personal shoppers this time. I grab an LBD with spaghetti straps and solid red and solid dark gray sheath dresses.

She tried the LBD and the red one; they fit. While she changes, I hit the shower and grab a black garter belt and shimmering black stockings and find black thong satin pants to match.

I keep it concealed from Judy. I pay for it from my own pocket. I want her dressed to the nines when we leave the salon. I slide a note in the bag.

Judy,

I cannot thank you enough for befriending me and for your support at work. It means so much more than you can imagine. Sharing today with you means everything to me. I can only hope you know I trust and respect you. You are my sister now.

With love, Bree

I get them rung up and pay them on our way to the MAC counter. Judy is seated on the stool.

The associate says my name is Tia. How can I help you?

My girl Judy needs a daytime and nighttime look. I said.

Tia, as it turns out, is trans like me. She's very sweet and very pretty. Her dark purple makeup has a slight goth feel but is also perfect for her.

Tia starts a quick color match on Judy. Judy's very fair-skinned with mousey medium brown hair. Tia strips her current makeup and says you apply your makeup well but with the wrong tones for your skin; you really should contour a bit more.

Tones, contour? Said Judy.

Tia says, for everyday makeup, you need 2 or 3 tones or shades for your foundation and 2 or 3 colors for the eyes. Tia shows her the tones she uses and how to use them and her blending technique.

Next Tia says eyes have the most effect besides lips. With your hazel eyes, we have many daytime options. Greens, browns, even a mix of soft pinks with earth tones.

Judy says I want a daytime power look without being heavy. Tia gets to work with a smokey mix of browns with a slightly heavy but not overstated eyeliner.

Tia gave her slightly long, thin eyeliner wings similar to my tattoo double-wing eyeliner.

Tia turns to me. I love your double wing liner; is it permanent makeup, Bree?

Yes, it is, and thank you. I said.

Judy says I wish I had permanent eyeliner similar to yours, Bree! It would save me so much time in the morning.

We can look into it today if you want Judy. Please, Bree. My pleasure, Judy. I settled up with Tia. Almost $300. I tip Tia $50. She just smiles,

I whisper that we T-Werls have to stick together. She hugs me. She hands me her card. Call me, she says. I smile.

10:40 am. We are in the car on our way to the salon. We arrive at 10:55 am. Walking in, we are greeted by Sabine and Alexis.

I say, Ms. Sabine and Alexis. This is Ms. Stapleton's assistant, Judy. Judy, these are my friends Ms. Sabine and Ms. Alexis.

Judy, it's a pleasure. We are glad you are early; we have a full day, so let's get to it. Said Alexis.

We have mud baths set for you two. Then we have separate services for you two. We strip and shower in separate stalls. We step out at the same time. My towel was tied above my ever-growing C-cup breasts.

I'm not trying to be rude, Bree, but can I see it?

My tape fell off in the shower. She's checking out my whole body now. Your tattoos are so beautiful. I love your body jewelry. I would have never guessed.

They did most of my body jewelry here too, I said.

Really? I always wanted to try some body piercings but am so afraid of what others would say or think.

Don't be Judy! Body art is just another form of self-acceptance and expression.

Can I touch you, Bree?

Yes Judy you may.

She cups my breasts gently, slightly kneading my breasts, caressing my nipple rings and small shields. She runs her soft hands down my stomach to my double-pierced belly button.

I let out a soft moan and gently grabbed her shoulder. She may be shy, but she has a very erotic and loving touch. Oh, I say. I pant just a bit. My split tongue sticks out just a bit.

Ohhhh Bree! Your tongue!

Oops! Sorry, I say.

Oh, let me see it, please?

I stick it out, clap my tongue, and flip each side up and down separately. That's both very sexy and freaky, she says. I say very softly, See anything you like.

Well, to be honest? Judy hesitated.

Yes, Judy, be honest!

We are friends. The tongue is a bit much for me. It is super sexy. Not sure I could do it. The nipple rings and the double belly button I adore.

If you want them done, say the word; we can do it today, I said, my treat.

Really!

Yes really!

Oh, what about Rick?

Rick will love it. All men do.

Bree, I noticed girls' names on your back; who are they?

I forgot about that tattoo. They were my daughters.

Were?

Yes, they died over a year ago in a car accident along with my late wife.

I'm so very sorry.

It's okay, I said.

Judy hugs me tightly as friends do, then kisses my lips softly. I really am sorry.

It's okay, Judy, really! Let's go back to our day, honey. I wink, and she sand miles.

Alexis walks in. Ms. Alexis, Judy is interested in the nipple and naval piercings today! Not a problem, girls. Oh, maybe a small nose stud like mine on the left side.

We can do that. Bree, do you want anything pierced today? I was thinking about a helix piercing like your left ear.

How about both? Alexis asks.

Alright, you talked me into it, Ms. Alexis.

Judy, what kinds of piercings would you like today?

I would like my nipples to be double naval like you and Bree have, and I would like 2 more in each earlobe and a left nose stud.

Wow! Said Alexis. Swinging for the fences? Any tattoos today?

Well, now that you mention it, I would love permanent eyeliner with wings—thin, sharp wings if possible.

We can do that, said Alexis.

For now, Judy, Sabine will take you to our waxing room for full-body waxing. Bree, you are with me for the same. Follow me, ladies.

Alexis whispers in my ear, Does she know?

Yes, I told her.

Okay, good, she's cool with it?