Meeting My Mistress Chapter 38

Come on time to clean you up and out. Ian says now pay attention, Terri, you need to learn to give yourself enemas twice a day. Once in the morning and once at night.

Ian brought out a medical stand, the enema bag, the nozzle kit, and the lube. He showed me how to use it. The different nozzle and how to use it. He gave me a 2-quart soap enema and then a 4-quart water enema.

He then gave me a 1-quart rosewater enema so I'd smell fresh and pretty. He then showered with me. He unlocked my chastity and washed me thoroughly then locked me back up. As he finished me he had me wash him up.

I saved his manhood for last. After I rinsed it he grasped my head both hands and guided my head to his erect shaft. I let my instincts guide me and proceeded to service him with a new passion.

He was moaning and pushing in and out of my lips. I must have been doing it correctly because I felt him swell up and I swallowed his warm juices down my throat. I was very happy with the ability to make him cum as quickly as I did.

Ian toweled me off and showed me how to tie the towel around my ample breast. He looked at me and said,

No pressure meant, but I think you'll be a terrific woman, Terri.

Thank you was all I could say.

Time for you to get ready, honey. You have a long day ahead.

Yes, I do I said. I started by deciding what to wear. I pulled out my red pencil skirt suit with the white silk blouse and matching chemise and white panties. I put on my white garter belt with nude stockings and 4" red heels.

I did my makeup in a light red smokey eye and winged black eyeliner with red lipstick. I marched downstairs, and Ian had my breakfast ready.

A small fruit salad topped with vanilla yogurt. Instead of my coffee, I had Ice water. I had an extra bag with me. Mom and Aunt Becky were sipping coffee when I came into the kitchen.

What's the extra bag for? Asked Aunt Becky.

Change of work clothes, server rooms are dusty and dirty.

Makes sense said, Mom. I am going to head in early, there's much to get done today.

Mind If I ride with you asked Mom.

Sure honey. Carol smiled.

We grab our stuff and head out. I kiss both Ian and Aunt Becky on the cheek, and Mom and I are on our way. I open the door for Mom. After we get on the road, Mom starts talking.

Terri dear how are you doing?

I am okay.

Honey. Please talk to me. What's running through your pretty head. You can talk to me, honey. My love for you won't diminish.

Mom. Yes, sweetheart?

I am scared!

Of what honey?

Scared that I really love being a girl, but I am a boy.

Sweetie, you're a good person, said Mom. Just because you have a penis doesn't mean you are a boy or a man.

You are who you are, gentiles don't define you.

I know that Mom, but I can't escape the thought of it, either. I've been a boy my whole life. I never imagined any of this, now look at me!

You don't like it?

That's the problem, Mom. I love it!

You and Ian sounded like you had a great time?

We did, he's amazing! Omg Mom, did I just say that?

Yes, you did, my Terribear!

I love it when you call me Terribear.

I know sweetie.

Terri, do you enjoy being a girl? Are you enjoying your breasts?

Yes, and Yes.

Mom?

Yes, sweetie.

Can Aunt Sophia shape my nose just like yours?

I am sure she can, why do you ask?

Well, whether or not I remain a girl, I'd love to look more like you.

Ahhh honey that's very sweet of you to think so.

I love you, Mom.

I love you, Terri! Are you sure you're okay with the trac shave?

Yes, I hate my Adam's apple. I love to, at the very least, full facial laser hair removal; I hate shaving.

I will set it up with Alice for weekly appointments, I take care of everything. If you need more, just ask and send me the bills, okay?

Thanks, Mom.

After work we need to go shopping you need a Sunday dress.

Mom, can I get Aunt Sophia to enhance my breasts on Saturday before the event?

I want to be my feminine best for Papa.

I'll see what we can do.

Thanks, Mom. Mom? Do you think Nana and Papa would accept me if I were to become a girl?

Terri, your Aunt Bree, and I know them better than anyone; we think they will. Besides, they have to accept Aunt Bree. There's no going back to being a man for her.

You, on the other hand, are at a crossroads. Whichever way you choose, I will always be "On Your Left," as Captain America says!

We giggle.

You're a Coven member now for life. The Coven has your back.

Now tell me Terri, did you enjoy your time with Ian?

MOM!!!!!

Come on, honey, a daughter shares these things with her mother.

As you must know, it was fantastic. It was the best sex I ever had. He was firm and controlling but not abusive. He made me want to please him without forcing me. I found myself submitting without force. The more I submitted the more freedom I felt. It was like my body knew what to do without me thinking about it.

Ian is a magical lover, Terri. I know firsthand.

MOM!!!!!

Terri, my dear, you are a Coven member now. Coven members talk openly with each other about our lives, especially our sex lives. We are mother and daughter, but when discussing sex we are Coven members first.

Mom, do you want me to be your daughter?

When I asked her I had a tear forming. This conversation is an emotional one for me. My mom knows I am on edge. The truth is what I need. I've asked this question a dozen times.

Carol/Mom hesitates before answering.

Terri, when I was pregnant with you the doctor said you were a girl. When you were born you were a boy. I was just as happy. When your dad and brother weren't around I used to dress you as my little girl.

Your dad was livid with me the day I came home with you with your ears pierced. Yes, I wanted a girl; yes, I wanted you to be my daughter. More than anything I want you to have a happy life.

I want you to be my daughter. But I love you as my son or daughter.

Mom I love you. But If I stay as a girl what is going to happen to me?

Nothing you do want, Terri. Terri, being a girl has advantages and disadvantages. In my opinion, the advantages far outweigh the disadvantages.

Look at Matt for example. He's smart, handsome, macho, brave, and protective. Under all that he's still a little boy. Watch closely when we're together.

He's my bitch! We lead a normal life outside, but behind that door, I'm in charge. Why do you think he never questions me! In return for his trust and submission, I allow him the freedom to be himself outside with limits!

He knows I won't hesitate a second to lock him in chastity. I love Matt with my whole heart. I own him. He loves me endlessly. All this is built on trust. He's happy and so am I. We are both honest with one another. He's much happier as my submissive, ask him.

Moments later we arrive at the firm. It isn't even 8 am yet when I drive into the parking garage, and I pass Judy's new Audi. The nameplate for the space has already been changed to her name.

I mention it to Mom.

Judy's a real asset, Terri. She's already settled or in the process of closing most of Jason's old cases. Becky and I have big plans for her, you keep that to yourself.

Yes Ma'am.

Mom, would it be okay to change into my casuals in Aunt Becky's office?

Sure sweetheart, we wouldn't want you messing up your office clothes. Thanks, Mom.

I start my work at Bree's desk. As I clack away very carefully with my new nails Judy walks up.

Morning Terri! In her musical voice.

Morning Judy I smile radiantly.

Stand up, honey. Let me look at you.

I comply, and she waves her finger to spin. I step out from the desk and spin.

You look... Wow! Don't say it. Okay, hair, nails, and makeup are perfect; I love hair color. What's different, she locks on my breasts.

Terri, you have breasts!

Yes, I blush red! Oh, girl, they are so you! Are those real!

Not realizing I was showing some cleavage. Yes all me!

How?

Aunt Sophia gave me saline injections. This way I could try out real breasts.

Well, they suit you!

Thanks, Judy.

No, I really mean it. Their perfect!

I smile widely at her approval.

Is Becky in?

No, but Carol is.

Can you buzz me?

Sure. Ms. Elgin Judy needs a minute?

Send her in. Nice seeing you Terri.

You too and thanks.

Terri, if you're up to it, we should do a girl's day soon, you, me, Bree, and anyone else that wants to come.

I'd love that thanks.

Judy enters the office as I continue my work. Just before 8 am Cathy marches in.

She smiles at me and settles in.

Morning Cathy.

Morning Bree, wait..

Terri?

Yes

Terri. My gosh, girl, look at you! Don't take this the wrong way. I thought you were pretty yesterday, but Wow, you are a beautiful young woman!

Thank you as I blush again. I adore that skirt suit.

Thank you I said.

What's your work plan Terri?

All network IT stuff today. I have to patch up the security on our network. Check your email. Everyone needs to change their passwords today.

Aunt Bree and I have a lot of work ahead of us. Everyone here is going to be flexible with things over the next few weeks, and all cell phone users will be getting new phones in the next few weeks.

Everyone will be sent emails on the new protocols Bree and I are setting up. So spread the word and back up everything. Server accounts will be set up for everyone.

Sounds like a big project. It is, but by the time we're done, it will be as secure as the NSA networks.

So you won't be taking calls at all.

Not if I can help it.

We giggle and get to work.

After I set things up and sent out the emails. I change into my jeans and Pink T-shirt and head to the server room. All the equipment is still in one piece minus the equipment the CSI people pulled out, which gave me an Idea!

I ran my diagnostics and patched everything. I then ran test after test. I found a couple of things that needed attention and made the repairs. I left 10 pages of notes and instructions for Bree on what was needed.

It would have to be done after hours and on the weekend. She should need more than a few hours to run it on Sunday night.

4 pm arrives Mom comes out. Come on, girl, we have places to be. We head into Macy's and start our Sunday dress shopping. We ended up with two dresses.

Pink lace and white lace dresses with matching lace gloves. They hung at knee length. Mom selected white Mary Jane with 5" heels and Pink T-bar heels and 5" heels. She said if you're going to be a young woman you need to dress the part! Yes Ma'am.

Bree and Mary

Mary and I arrive at the Spa just before 8 am on Friday morning. We have one week left to rehearse. She's dressed in her full-length black catsuit with opera-length gloves, red and black goth pattern corset, and 7" spiked platform black ankle boots.

I have a hot pink latex tank dress with pink thigh-high 6" platform spike heels and a full-sleeve white fishnet bodysuit. Under it is a very tight waist clincher. No bra. My piercings are very obvious in the dress.

My solid stainless steel collar is very obvious. We both wear long black patent leather trench coats to hide our outfits. As we walk in Sophia greets us.

Good morning girls.

Good morning, Mistress Sophia, We say.

How is your charge doing so far Mary?

She's extremely compliant Mistress said Mary.

Really?

Yes Ma'am. She really knows how to wake up her Mistress in the morning.

How so?

Orally, She gave me multiple orgasms already.

Really Mary?

6 Mistress Sophia. Hmmm, I may have to try that soon.

It would be my honor, Mistress Sophia.

I will hold you to that Bree.

Yes Ma'am.

The dungeon is all yours girls. Mary, do you have your keys? Yes, Mistress Sophia. Good, lock up when you leave. There's no one on the schedule so you two should have complete privacy from now until next Saturday.

Bree, I expect nothing except complete obedience!

Yes, Mistress.

Mary, I expect a flawless performance next Saturday night. We are all very excited.

Thank you, Mistress Sophia.

Mary locks me in the St Croix cross as she prepares the ropes. It looks like she is prepping me for Shibari. Mary says nothing as I watch her get everything ready. In the dungeon, I know the golden rule: no talking unless spoken to.

She lays out a pink ball gag. I hate those things, however they are sometimes necessary. She also lays out a hood with blinders, a riding crop, a flogger, and a cane.

I begin to sweat from fear. As I sweat my clitty tightens in its chastity. I know it's only a matter of time before I am fitted with a rope skirt, full rope dress, or a very tight multi-knot rope harness.

She then organizes a series of strap-on dildos and anal ball dildos in various sizes. The last things she sets out are lengthy rubber gloves and a large bottle of lube.

Mary smiles at me and says are you ready Bree?

I think, gosh, no, no way! I smile and nod and say Yes Mistress Mary.

Excellent let's begin.

She released me from the cross. I drop to my knees and kiss her phallus! And we begin.

Putting a gentle kiss on the phallus head has sealed my fate.

Beg me to bind you, Bree; beg to be violated, roped, and dominated!

I beg, plead with her to bind and violate me. To bound shibari style.

She smiles, looks into my eyes, and says, as you wish, my pet.

She gives me her hand signal and I undress. Thinking to myself let the games begin.

My hands are bound with rope and raised above my head. Mary made a loop between my hands and hooked me to an overhead hook that was winched up, stretching my body out.

I am barely able to stand on my tippy toes. She starts with a breast bra all rope and loops it through my collar loop pulling my breast up a bit.

Using medical tape she covers my belly jewelry and proceeds to rope me just below my ribs all the way to my ankles.

Comfy my pet?

I nod in silence as she smiles wide. She lowers me so my feet are flat and proceeds to kiss me.

My sweet sissy you've no idea how hard this is for me. You gave me the most mind-boggling orgasms I ever had, man or woman. She kisses me deeply and then proceeds to attach bells to my nipples.

Next is the spike wheel, she runs it across my breasts. She canes my roped body. The ropes soften the sting, but more than one blow finds my soft skin. I begin to tear up. My chastity tightens.

I am in pain, it stings awful. But as much as it hurts it's a rush of eroticism. I am both in a rush of pain and turned on by torture. I try to keep myself silent to avoid the gag.

Mmmpppffff in goes the ball gag. Yes, we're in the second-floor subbasement, but discretion is paramount.

A quick note it wasn't until months later I found out our dungeon rehearsals were all recorded. Not for blackmail but for in-house Coven training and entertainment.

After what had to be almost 2 hours of Shibari bondage, hanging, and caning. I was lowered, the bottom half of my rope skirt was removed and I was allowed to stand on my own.

This was short-lived. My ankles were shackled, then the rest of the rope dress was removed. A 4-foot-long spreader bar was locked between my legs.

Mary attended to my caning wounds with a lotion. She rubbed it in gently.

Whispering my ears how I was her good little sissy and pet. She told me my limits were to be tested today. She wrapped my crotch In another Shibari harness style, spreading my ass cheeks wide.

My plug was removed, and a long multi-ball dildo was lubed up, and she slowly inserted it in a very loving manner. 5 balls in all each bigger than the last. My ass was stretched to its limit or so I thought.

She played with my balls keeping me stiff and confined. She ran the spike wheel gently across my scrotum. It was ecstasy and a bit uncomfortable.

She then started squeezing the blub attached to the tube. I felt my ass begin expanding. It also seems to push deeper within me. The ball dildo was over 18 inches long, and now it is both wider and deeper.

My facial expressions couldn't mask my feelings as The size grew within me. I started leaking precum so much that Mary put a condom on my cage to collect it all.

How are you feeling my pet?

Violated and dominated, Mistress!

Perfect! Mary says. When we're done, you should feel violated, used, abused,, and loved. One step shy of rape without the hate or violence associated with it.

Remember I love you, Bree. This is our special time, I own you! This is our time. We will be bound by this forever.

Yes Mistress I said.

She smiles and says you're my first special bitch, now and forever.

The bindings were removed after what seemed hours. My filled condom was removed. My balled dildo remained deep within me. I was showered, cleaned, and given a robe to wear for a light lunch of bottled water, and yogurt. I was allowed to use the bathroom. She led to the saw horse. It was black latex and very heavily padded. I didn't fear the horse as much. I've been taken on the horse before. I mounted myself on the horse as instructed. I positioned myself to easily be shackled.

Mary was impressed with my position. The horse height was adjusted for Mary. She began teasing my hole in a firm but loving manner. I was softly cooing with her attention.

It's not your first time on the horse, I see.

No Mistress.

Well, I hope you're up for your first dungeon fisting.

Yes, Mistress. I really wasn't but it's not like I had a choice in the matter.

Bree, honey, I need you to relax completely. This will be extremely intense; contracting, tightening, or stiffening up will make it worse. Trust me, stay relaxed, and you'll love it! I promise to be careful.

I love being fisted. I said.

If you're good maybe when we get home I'll let you fist me. Good sissies need to learn to fist one another.

Sissies are not allowed to have strap‐on sex very often. Maybe one day you'll earn the right to get a vagina; for now, you're a sissy bitch. Sissy bitch's are sex toys. Your mine, bitch.

Mirrors were positioned so I could see her actions. She must have stroked that ball dildo at least two dozen times before she pulled it out. I was gaped; I could feel cool air inside my hole, which was different. Mary commanded me to pucker my hole. She called it blowing kisses. I blew many kisses. She mounted me with a larger strap-on. As if the first one wasn't large enough.
She was initially gentle and slow allowing my freshly lubed hole to adjust. The faces I made showed the intense nature and stress my body was experiencing.

Once all the way inserted she gave my body a minute to adjust. She'd whisper, breathe my sweet slave, relax, and breathe. Enjoy this, imagine being on a beach, making sweet love to your wife. Give in, submit, and breathe. I did as I was told. I relaxed and tried to breathe. Once I was relaxed she began thrusting, slow at first. She sped up to a rhythm she liked and rode me to town.

A fresh condom was collecting my precum. I was leaking something terrible. I had no control. I was bound all over unable to move. I was just her hole to play with. I kept my moans quiet as I could to avoid the gag. I could feel her body slapping mine. I watched as my hole was assaulted over and over. I watched as the lube leaked out from me, almost like cum.

I was so turned on I couldn't get enough. I wanted more; I wanted to move with my lover, but I couldn't. I felt open, stretched, violated, and loved. It was then I knew there was nothing I wouldn't submit to now. I want to eat her sweet pussy. Savior her wet juices, and make her smile from my tongue.

I started to cum, but Mary recognized my moan change and slowed way down, then sped up, then down, keeping me on my edge. Over and over, I knew better than to ask to cum. She's in charge and it's all about her.

I figured if she's happy I am good with it. I am willing to suffer to provide her pleasure. The shibari ropes are beginning to get very wet as sweat pours out of my skin. My skin is on fire. She continues to pound my hole repeatedly.
I'm bound tightly and my body is limp. My mind is foggy my body is purely exhausted from the onslaught of constant thrusting and pounding.
She slows and inserts the bigger dildo in deep and my anal ring locks it in on the base's narrow ring. Mary releases me. I almost fell off the horse.

Awwww baby I am so sorry. You okay?

Ye ye I am f f finne. I look up, Mary?

Yes I, I, might need a minute. Uhh, and I pass out.

I awake in a jacuzzi tub running full blast. Sophia is standing over me.

Welcome back! Sophia said.

It's then I notice no ropes or dildos in me.

Come back, Bree. She lightly snaps her fingers, come back to me, Bree.

My grogginess begins to fade and come into focus.

My precious Bree, there you are.

Whaa, What happened?

You passed out sweetie.

I'm so sorry Mistress Sophia.

It's okay! Sweetheart, you're alright.

Mistress Mary, I am really sorry.

Don't be honey, said Mary.

That was a very intense session. You passed out with flying colors! The Mistress giggled as I became more awake. It's time for massage sessions.

Every Coven member, woman, man, and sissy is required to have intimate skills in Massage both therapeutic and exotic. Massage is one of the very few times a submissive can take command of their domme, with limits of course! The limits are determined between them and they can always change. This is especially important to sissies because it's a very personal and intimate action between the two that only they share. The knowledge of body and hand touch communication.

Today, Bree, you will receive your massage from Mary. Then you will massage her. If time allows, You will give me a massage today.

Yes, Mistress Sophia.

The mistresses lifted me from the tub, pat me dry with towels, and wrapped me in only a towel above my breasts. They help me put on white 4" mule heels, and place fresh a condom on my chastity. They each take a hand and arm and lead me to the massage room. They take my towel and lay me face down at the massage table. The table is heated and warm.

Bree honey, do we need to shackle you, or will you behave?

I will behave, Mistress Sophia.

Good, I will try to be back in a few hours.

Thank you, Mistress Sophia. Said, Mary

You girls enjoy it!