Meeting My Mistress Chapter 33

Written by Brianna Demonet

Mary helps me organize my clothes and gear for tomorrow. Bree, get yourself cleaned up inside and out and ready for bed and meet me in my room.

Yes, Ms. Mary!!!

I see Ms Mary packed my white babydoll nightie. Being our first night together I decided it would be the most appropriate. I shower and give myself two enemas, first with water and second with rose water.

I kept my makeup very light. Mascara, a little eyebrow pencil,, and a glossy pale pink lipstick shade. Being our first time together, I arranged my ringlets into pigtails. I was going for a virginal look. I think I pulled it off.

I slid my white babydoll, white garter belt with sheer white stockings and french cut lace panties, and white 4-inch heeled mules. Her door was closed. I knocked once, kneeled, and waited. It seemed like forever before she opened the door, it was about 30 seconds.

She opened the door and my head bowed to the floor. She touched my chin and said, rise my slave. I stood up as slowly and as gracefully as I could.

Mary was gothed out to the max! Black wig with red streaks, her skin creamy white, eyes with heavy eyeliner, and black and red eyeshadow. Black leather corset, thigh hi boots with 8" platform heels, black opera-length rubber gloves, and dark red lips.

Oh my, my, look at you, my sweet sissy. You look like a virgin ready for deflowering!

I was still wearing my stainless steel collar from earlier. She attaches the leash and says come in slave. I follow her lead as she tugs the leash. At the foot of her bed, a bondage bed. It was equipped with stocks, chains, and a suspension winch.

The bed was made up of latex sheets and bedding with red and black lace and leather trim on the canopy. She gave only hand signals. Kneel, I kneeled. Kiss my boots!

I began kissing her boots. She bent down after a minute and gave me the eyes up-hand signal. I looked into her beautiful Green eyes.

She spoke. Bree, you realize for the immediate time I own you! You are here because I need you and you need me! We are a team. You are not going to enjoy everything we do together, some things will be painful.

It's through pain we find our higher purpose. You owe me a debt which I will make certain you have paid in full by next Saturday night. I am the one being judged but your performance will speak volumes for your status in our Coven.

Do you still wish to be mine for the next 10 days? Nod once for yes.

I nod then look up and smile.

Good girl, sissy.

For the purpose of our practice, you will address me as Mistress.

Do you wish to be deflowered by your Mistress?

I nod.

Good, will you obey my every wish?

I nod. Have you ever experienced bondage?

I nod.

Heavy bondage?

I shake my head no.

Are you willing to submit to heavy bondage?

I nod.

Good girl sissy. Crawl on your hands and knees and put your head and hands in the stocks on my bed. I crawl and climb onto the bed. She lifts the stock and I take my position.

Bree, you are to be deflowered now. But first, all sissies need to know their place. I will place you in chastity and flog you first. She pulls off my panties. She attaches bells to my nipple rings.

Then I feel her place me in chastity. Bree, we can't have a sissy that's not locked up. Don't worry, I was informed that there is no penis or ball torture for you; they will be safe.

Your ass isn't going to be as fortunate. With that said she locked a spreader bar between my ankles. It must have been 4 feet wide. She dangled the flogger over my face, arms, and ass.

She brushed my ass gently. Then I no longer feel it. Not 2 seconds later, crack, crack, crack as each blow landed I fought the urge to cry in pain.

Tears started flowing from my eyes. I began to whimper as blows kept meeting my ass. After about 20 or 30 I lost count. I'm crying quietly in pain...

She locked a ball gag in my mouth and continued. I did my best to take it. My body betrayed my free will, and I collapsed from the pain. I must have passed out.

Mary was wiping my face with a cold washcloth as I came too.

Bree sweetie you alright?

Realizing my ball gag was removed, I answered,

Yes, Mistress.

Are you ready to continue?

Yes, Mistress Mary. Good girl!

I felt something rubbing against my leg as she wiped my face. I didn't think anything of it at the time. I felt Mistress lube me up. I knew what was coming. Soon I felt the pressure as she slowly pushed inside me.

I started breathing and relaxing as she entered me. It's a good size Strap-on but Ian is bigger. I begin to push back to her now in a really nice rhythm.

We seem to be in tune together. She smacks my sore ass, telling me what a good sissy I am. She slows down, pulls halfway out then attaches a new phallus. She pulls the old one out, and before I know it, she pushes in, and I feel the stretching of my sweet hole.

I am exhaling hard, trying to relax as she slowly pushes inside me. As she bottoms out, she holds it in, waiting for my body to adjust to the monster inside me. What do you think of this my sweet little sissy?

It's a huge Mistress.

Does it hurt?

A little I just need a minute, please, Mistress.

Of course Bree.

Bree, try moving yourself on it just a little side to side, up and down, and back and forth.

I do as Mistress suggests, back and forth is very difficult locked in stocks. I can't arch up like I love to do.

Turning my head to kiss my lover, is out. Submission is my only choice. I do try all she suggested it's feeling a little better. All of a sudden I feel a cool fluid running inside me.

This will help sissy She says.

Do you feel it yet?

Yes, Mistress. That is simulated cum lube. This is an ejaculation phallus. She starts to pump my hole slowly back and forth. There's less pain now and the pleasure starts racing through my whole body.

Every stroke is longer, every thrust deeper. I moan like never before. I keep my mouth closed just trying to enjoy it. My body strains from its immobilized position. I am locked in my chastity and it is tight and leaking pre cum. I try to maintain a rhythm with Mistress.

I hear Mistress cumming. All of a sudden another jet of cum lubes jets inside me. I feel it running outside me dripping on the back of my balls. She slows and pulls out. With her gloved hand, she inspects my newly gaped hole.

Ohhh, Bree, you are one hot sissy. If you weren't married to Becky I'd take you for my own. Are you ready for round 3?

Thinking to myself, It's not like I have a choice.

I say yes Mistress.

I feel 4 fingers inside me then a stretching and a small pop. She has her entire hand in me!!!!

Ohhhhh, I said as quietly as I could.

Next thing I know I feel her wrist bone and her hand deep inside my body. I feel her arm move in more and more. My head is spinning my body is pulsating.

My hole is constantly expanding and contracting. I have no control over my body's responses, I can hardly move. I can't push back, I can't fight it. I attempt to keep breathing.

My body begins to spasm uncontrollably. I try to focus. I am lost in an erotic state of pure pleasure. My chastised clitty is leaking like a faucet. She continues, knowing I am about to pass out again. Mary doesn't stop as I feel my body goes limp again. I feel a wave of cum exit my clitty and everything goes Black.

I wake up in her Jacuzzi tub with warm water jets on high. She's sitting next to me. Washing my body. My hair is in a shower cap. I can barely move.

Hi, sleepy head.

Hi Mistress.

You were fantastic Bree.

Thank you, Mistress.

Bree I want you to know you're a great lover. I've never seen endurance like that.

What endurance, Mistress, I passed out again. Yes, you did, after 30 minutes.

That long?

Yes!

It felt like 5 minutes.

Bree, my sweet sissy, you have been very well trained.

Thank you, Mistress.

Who trained you in the bedroom?

Mistress Alexis.

She did a fantastic job. How are you feeling?

I'm okay, Mistress. My butt is still sore, and my hole is a little sore too; not too bad, though.

After our bath, you will be sleeping with me tonight; you earned it. I expect oral service in the morning, I have been told it's the only way to wake up in the morning.

Mistress Mary, I planned on waking you up that way already, provided I wasn't tied up. Keep up your great behavior, and being bound at night will be one thing you won't have to worry about.

I promise Mistress.

We wash each other in the tub. Mary is one built woman. She's very toned; she has an almost bodybuilder physique, only slightly smaller. Her D‐cup breasts are natural and firm. Her skin is silky; her nipple rings are gold, her flat washboard stomach is very firm, and her Naval has 4 piercings, over and under and one on each side.

Her body, like mine, is completely devoid of hair anywhere. She has a tattoo of Roses and vines all the way around starting at her pubic area and framing the top of her gorgeous round ass.

I wash her body in the same loving manner as if she were my wife. Mary says nothing, only moving to adjust as I wash her. As I wash her I notice my collar has been removed.

Mary says, let's get showered up sissy girl. We have a big day tomorrow. She starts the shower and we begin washing one another. She washes me first. Her touch is very caressing and caring. She massages my sore ass. She massages my hole, I moan softly.

When it's my turn, I wash her golden brown hair, massaging her scalp, my fingers combing her beautiful mane of hair. I wash her back in a circular motion lightly dragging my fingernails across her skin.

She lets out soft moans of approval. I work my way down to her feet. She turns to face me, I begin working my way in the same manner. I wash her love button and slit. I rinse it well.

As my hands continue up I start my shower worship. I put every ounce of passion and skill into pleasing her, just like my wife. Her hands lovingly stroke my shower cap.

She moans with approval. I feel her legs tremble I speed up my tongue activity. Her moans increase, and I feel the first wave beginning. I slow just a little, then increase my service area.

Then speed up a bit and penetrate a bit deeper with my tongue. Looking straight up, her eyes are closed, her head cocked up just a bit, her mouth open.

As I speed up she peaks and sings in an orgasmic moan. I smile while buried between her legs. I slow for a couple of seconds as she shakes. As her shaking slows, I go right back at it.

Her body responds and the wave returns. I am in command of her body now. She's now at my mercy. I start flipping my tongue over her clit and hood.

I lovingly suck her labia and brush it with my tongue. I must have hit the right spot because she screams with pleasure, and her body shakes even more. I continue my worship as She orgasms 3 more times very quickly.

It was much faster than I anticipated. I feel her begin to wobble, I wrap my arms around her waist. I Kiss her love nest and wait for her to regain her balance.

Ohhhhh Bree!!!!!!! What was that? Where did you learn to do that?

Mistress Rebecca, Mistress! I have had a lot of practice.

I can see that. She's still panting as she talks. Do you do this every morning and night?

Just about Mistress. Just wait until morning, It's better than coffee! At least that's what my wife says.

So you're saying Becky is missing out on your services for the next 10 days?

Yes, Mistress!

Oh, Bree, I am going to owe her big time!

Perhaps Mistress, but the Coven is about sacrifice for everyone's advancements, isn't it?

Yes, Bree, it is. You are a very generous person.

Thank you, Mistress.

We towel one another off. She places a larger-than-normal plug inside me. I know this is larger than you normally wear but I need you gapped and ready for Saturday night.

She dresses me back in my sheer white babydoll nightie. We climb in bed, and she spoons up behind me, kisses my neck goodnight, sissy girl.

Goodnight Mistress.

Even without an alarm, I wake up at 5 am. I shower, enema, put on some light perfume,, and make my way back to Mary's bed. She is still in deep sleep.

I position a pillow for her lower back and ass. As with my wife, I gently roll her on the pillow, slightly elevated. She isn't wearing any panties. She must have been thinking ahead.

I slowly, gently spread her legs. I begin lightly licking, sucking, and kissing her beautifully pierced nest of love. I softly pull, lick and suck her jewelry.

I slowly bury my tongue deep inside her. Her body shakes with surprise. She's up now! She begins to speak, I put a finger on her lips to be quiet.

She responds by tapping my finger and understanding as I continue. Sub/superior relationships are different for everyone, it's the highest form of trust that people can share.

I love beginning a sissy and sub. I love living in an FLR relationship. When I service my superior like this, I become the dom of sorts.

I am in command of their body, their reactions, their pleasure, their orgasms, and even the sounds they make. As long as I am between their legs, man or woman I have the power!

It's a power rush like no other. Knowing that my partner is in my control even for a short time, it's a terrific feeling to control someone who controls you 23 1/2 hours a day. The biggest charge of it all is the trust we share.

I continue my ministrations as she builds up for the first wave, I hold her there a bit longer than the shower. She's dying to cum and I know it. I let her surf the edge denying her orgasm.

As I listen, she moans. When I hear her relax just a little, I speed up. Her body tenses up, her legs tighten, and she explodes in a violent rapture.

As she comes down I build her up quickly, never letting up. She is at the edge again. This time, I work through the wave, let them ride it for a minute, then speed my tongue and, use my fingers, make her cum as hard as the first.

But this time I made her cum longer and longer. She surfs a 5 minute constant orgasm. She's panting, moaning, and grasping my head. She says nothing.

I love this control. I don't think she realizes she's lost control. I let her start to come down a little then start over again. I lifted her legs changing my head position to the side and starting again.

She builds up the wave again. This time I pushed straight through, getting her to explode once more. I continued at it again. She's shaking with a strong orgasm. I held it there for 6, maybe 7 minutes. She begins to dry up.

I hear her Say, Breeeee!!!!!!! She goes limp. She passed out on me! That's a first!

I check her. She's alright, just out. I wash myself up and get her a cold wet washcloth like she did for me. I wipe her face and forehead. She begins to come back.

I kiss her lips and smile. Good morning, Mistress. Sleep well? My smile is wide with pride. I know my wife will be proud of me.

Oh my gosh, Bree,, you are a very talented girl, thank you.

My pleasure Mistress.

How long was I out?

For about 15 minutes, I took the liberty to clean myself up and let you recover a bit before waking you.

Bree, you're magnificent. That is without a doubt, the best oral sex I've ever had.

Thank you, Mistress, still smiling with pride.

Does Becky get that every morning?

Yes, Mistress. No wonder she's been so happy these last six months.

I love her completely, Mistress. She, you, the Coven, and saved my life.

I am dedicated to her and the Coven forever. I will always be here to serve.

I can see why you earned your special tattoo so early. A few sissies are very upset with you cutting in front of them.

I was a bit upset about that too. Now I know why. You truly have earned your ring.

Thank you, Mistress.

One question.

Yes Mistress

Were you dominating me just then?

Yes, Mistress, I was. Where did you learn that, how did you know it was acceptable?

Mistress Alexis, Becky, and Lisa. I learned that as long as I am in service mode and you're on a pleasure wave I can control your body to my will.

I like to think it always benefits my partners if they can let go and let me take the wheel of pleasure for a drive.

Well, Bree, I gotta say it works!

Thank you, Mistress Mary. It makes me happy that you are pleased and satisfied.

Very satisfied Bree.

Come! It's time to get ready. We need to be at the spa at 8 am. We are going full goth for the next few days. For you today, your black and red latex skater dress, and for me, a black catsuit with a red corset.

Don't worry, Sissy, we will be walking in the private entrance in the back. Very few clients know about the spa dungeon. While it isn't illegal to have a dungeon or offer its services, Dr Channel prefers to keep it private.

Terri's new Adventure

As I wave goodbye to Aunt Bree, I realize I am alone as my feminine self. Keith says his goodbyes and will see Ms Becky at work in the morning.

Alexis said she and Keith were going to her place for the night.

Aunt Becky says we may have a busy day tomorrow we can all use the sleep.

We head inside, mom says Terri! Come with me.

I walk with her to her room she pats the bed beside her.

How are you doing Terri?

Scared mommy.

Really?

Yes, Mom. I was all about this sissy girl thing when Aunt Bree was here, but she's gone and I'm not so sure now.

Bree will only be gone a few days honey.

I know, but between being alone as my sissy self and after talking to Aunt Lisa, I'm not so sure anymore.

Talk to me Terri, just let it all out.

Well, it all started with Sara and the salon. Sara fascinates me; so girly, warm, and open. She's more of a woman than any woman I ever dated.

She makes me feel free, happy, and loved. I feel like a complete person with her, there's no effort or thought to it.

Being a sissy is exciting, and Aunt Bree is so inspiring and happy, happier than I've ever seen her. I want to be that happy. So I thought this might be my path. Terri says.

I know you always looked up to Bree, honey. That's no surprise there. Terri, you need to know your Aunt Bree was conflicted with gender dysphoria for a long time. Said Carol

Bree also suffers from PTSD as well. It was only after his family's tragedy that he decided to embrace his true self. That took an extreme amount of courage on its own. Then coming out here on his own.

Well, that took guts I don't think I have. You need to know before Aunt Becky reached out to him that he is at rock bottom, ready to end his life.

Becky, my Dad, and Mom had him to get out and visit us. I knew about Becky and him and their internet chats. I suggested she invite him.

This was the right choice for Brianna! That doesn't mean it's right for you.

What do I do, Mom?

First thing, keep your visits with Lisa. She will not force you into anything you don't want. Second, just be honest with us. If this isn't for you then that's okay too.

Terri my love, I want you to be happy. How you choose to get there is up to you. I will back you up, that you can count on.

Thanks, Mom.

You're welcome, sweetheart.

After talking with Mom, I feel a bit better. I go to the dresser and put on my old Nirvana concert shirt I used to wear to bed. It seems so scratchy now.

I see the pink satin babydoll nightie and panties and try it on. It feels much more comfortable. I slide under the satin sheets and I'm out.

Mom wakes me up. Come on, Terri, we have to go to work today.

Mom, what do I wear?

Where what do you want to wear? Just remember, it's a law firm that needs to be professional. That really didn't answer my question. I go to my closet, and all my male clothes are still in my bags at the hotel, unwashed and wrinkled.

It was just then that I realized the breasts were still attached to my chest. They aren't coming off. I lay out a light blue blazer dress and find white heels that match the silk blouse.

I grab the short white slip and white garter belt and stockings. I found the white waist cincher. I get my white bra and panty set.

I shower and shave my face closely. My facial hair is sparse, to begin with. I get my bra, panties, garter, and stockings on. Normally I would be upset to be dressing this way, but I love the clothes.

I never enjoyed clothes like this before. I love the feel of everything, even the heels. I just finished my makeup and mom walks in.

Ohhhh Terribear!!!! You look lovely.

Mom's approval just reinforces my new style. Just then, Aunt Becky walks in. They notice the nightie lying on the bed.

Terri, did you sleep in this? Asked Becky.

Yes, I replied sheepishly. It's more comfortable than my scratchy old T-shirt.    

That's why we wear them, honey! Your makeup looks lovely.

Would you like help with your hair?

Yes, Mommy.

Next thing I know both Becky and Mom are brushing and shaping my hair. It has lost most of its curl. They tie it in a high ponytail and fluff it out. Mom helps pack my purse. I didn't know I had a white purse. It's white leather with a white leather strap and gold chain.

Honey you need Jewelry said Becky, I'll be right back. She comes back with 3" gold hoops for my bottom holes and a herringbone necklace and gold bangles for my right wrist and mom grabs the gold watch she bought for me. I button up my Blazerdress and look in the mirror. All I see is Terrigirl, no trace of Terry the boy.