Meeting my Mistress - Chapter 23

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Alice speaks softly in Terri's ear as she runs long beautiful nails across his ass and back. Terri, sweetheart, I have known you since you were a young boy. I have always loved you,

I love you even more now. Your trust and submission mean everything to me. We are going to take your virginity today. You will never be the same after today.

Today sex will mean something extremely different to you. I hope you appreciate and enjoy the new view on sex. Please keep an open mind. Just relax and enjoy the experience today.

Terri everyone here has been through exactly what you are about to experience. Do not be ashamed, be proud. The fact you trust in the Coven means everything to us. Shall we begin?

Just nod if you want to begin.

Terri nods.

Ian, Keith will you please prep our girl? Yes Mistress they say in unison. Ian, with some playful action, removes her plug. Sophia inspects her dilation.

Keith, be a dear and hand me the second one from the left.

Yes, Mistress.

Ian, hand me the lube.

Ian hands her the lube with the injection nozzle.

May I Mistress? asks Ian.

Please do. Ian inserts the nozzle and pumps a generous amount in Terri. Terri moans softly in her gag. Terri, you've been injected with a special water-based lubricant. I have added a mild muscle relaxant. This will keep you more comfortable during your indoctrination.

Terri responded to the ball gag.

Sara and I assist the Mistresses with their strap-ons.

Terri is blushing red.

Mistress Alice is first. A moderate size 1 1/2" diameter and 7" long. She's gentle as she inserts her phallus into Terri. His moans increase as Alice begins her ministrations into Terri.

Terri moans into her gag.

Mistress may I? Asks Sara.

Yes, you may. Sara walks to Terri and sits next to his face. She brushes Terri's face. I am so proud of you Terri. You make me so happy honey. She strokes his back and kisses his forehead.

Stay strong, baby, relax, you'll enjoy it. Trust me I know. I cannot thank you enough for submitting to this. You won't regret it. I will make sure of it my love.

All the while Alice is pumping in and out as Terri moans. His penis is leaking precum. Alice speeds up her rhythm. Alice begins moaning as her orgasm builds to climax.

Sara wipes up the precum. She sits in front of Terri and says thank you,, baby. Alice finishes and pulls out.

Sabine is next hers is 8"x 2". As she inserts inside her, Terri's moans increase in volume. Sabine is more powerful in her ministrations of Terri's newfound sex organ. Sara ran her fingers through the ringlet curls she gave her.

Breathe and relax, Terri. Enjoy it; this is a special time for us. My love, Sabine increases her speed, and Terri starts leaking again. Sabine shudders and orgasms. She withdraws and there's a small pop as she exits.

Sophia is next; her phallus is 10" x 2 1/2". She lubes Terri before inserting. Terri's moans are more powerful this time. Initial insertion is a. It is painful for Terri as she bites on the gag.

Relax, baby. Not clench up. Breathe relax, baby. You have to relax sweetheart.

Mmmmffff, uuummm, mmmfff mmfff.

Baby relax. Breathe deep and exhale. Terri concentrates on her breathing. Sophia unstraps her lower back strap. This allows Terri additional motion. This motion allows Terri a change position.

His moans change he's now moaning like he likes it. His leaking increases again. Sophia squeals loudly as she climaxes. She pulls out a louder pop, this time, and a small cry from Terri. The cry was like he missed being filled. It's a cry I know well.

Lisa is last, 11" x 3 1/2" phallus. Sophia injects Terri with a sedative and re-lubes Terri. Terri, I gave you a muscle relaxant to aid in your next 3 rounds. You will need it, sweetheart, trust me. Terri's moans are loud and you can tell there is some pain.

Mistress Alice, may I help?

Of course Bree.

Terri? Babygirl, look at me, honey.

Mmmfff.

You have to breathe, just breathe. The worst part is over. Just relax, I hold her hand.

Sara says Baby, I know the feeling. It will be okay honey. Just think about us, happy together walking in the park, waking up in the same bed. Terri starts breathing, moving her hips to time Lisa.

Terri's moans change to enjoyment as the relaxant takes effect. Terri starts leaking and squirting all over. Sara wipes it up with her fingers and licks it in front of Terri and swallows it.

Lisa starts moaning and orgasms as she bucks wildly. Terri moans loudly and shoots a heavy load.

Ohhhh, Terri, you're a wonderful lover, she says, cumming together is so magical, isn't it? Thank you, baby.

She kisses his cheek.

Ian, you're up. Drop your shorts and show her. Ian drops his shorts.

Terri's eyes widen mmmmffff!

Sara says it's not so bad, honey. I've had him; now you will too. We will share with him forever my love.

Terri, honey, it's going to be great, honey. Don't worry, my niece. I had him many times. He's a magnificent lover. I told her.

Ian re-lubes Terri as a precaution. Ready baby he says. Ian pushes inside Terri. Terri's moans are loud and long. Ian is fully inside Terri now. Terri moans with both pleasure and pain.

Ian says oh my gawd, she's still tight. Ian makes small motions in and out from fully in to out a little then in fully in. Ian is an expert lover. He knows her body needs to adjust.

He feels her beginning to loosen slowly as he makes small but needed motions. Terri's moans are softer now Ian is working his magic. As his strokes increase, so do Terri's soft moans. Slowly, Ian increases to full strokes. Terri is moaning soft and long.

He's great, isn't he, honey asked Sara. Mmmmmmfff.

I know, baby, his cock is incredible. Isn't it great? Your first cock, and mine are the same one, Terri. Isn't this special? It's a wonderful feeling for him to make you so full, so deep, so loved.

Mmmmfff.

I know baby. I know, baby, I know. Breathe honey rellllaaxxx! Ian is full-on penetration now. Terri's hips buck back with every thrust. She loves it now. As she bucks, she moans wildly. Ian says oohhg my gawwdd I am cumming!

He injects his load deep inside Terri. Terri moans as hot cum flows deep inside her. Terri cums again heavier this time. She plops back on the horse.

Limp, exhausted, and very satisfied. She looks at Sara. Mmmmm ooooo.

That's it my love you were fantastic with him said Sara

Mmmm says Terri.

Sophia says, let's give her a little break. Her gag is removed, and she licks her lips.

Terri, my dear, are you alright? I ask her.

Yes, yes, I am okay.

How do you feel, my love asked Sara.

Incredible, horny, loved, used and slightly soar.

Sophia says Terri, honey, are you ready for your last one?

Yes, Mistress.

Are you sure?

Yes, Mistress.

Keith said Alice please show our girl here the grand finale! Keith drops his shorts.

Terri's eyes go wide with fear. Mistress, is that thing real?

Yes, sissy Terri, it is very real. It's a wonderful tool. You will enjoy it, honey.

Mistress Alice, may I do this without the gag?

Can you control your noise, Terri? I promise I will try Mistress Alice. Alexis, Sabine, Lisa, Sophia, what do you say?

I let her try. If she's half the sissy we've seen so far, let her try. Said Sophia,

I agree said Alexis

I, too, said Lisa.

Sabine? Let's give her a chance, see what kind of sissy she is.

Okay, Terri, no gag. But behave or it goes in.

Yes Mistress, thank you Mistress's

Mistress Alice may I have word asks Sara.

Of course my dear. They walk to the corner and whisper back and forth. Sara asks something. Alice smiles and nods; I hear Alice say great idea, honey, go for it.

Terri is relubed. Her gape is prominent and still soaked with cum and lube.

Sara says I never had one this big. You have to relax and breathe. If you feel like screaming, open your mouth wide, but don't scream.

Yes, Sara.

Keith slides his massive tool up and down her crack. He pushes slowly. Terri moans and ah quietly. Keith pushes deeper then backs off. Terri tries to relax, bucking against the shoulder strap.

Ian points at the strap Mistress may I release it.

Yes, Ian. He unstraps Terri. Terri is now free to lift off the horse. Keith pushes the head of his cock, and it pops in ooooo, Terri cries softly. Deeper he probes inside her. Terri moans softly, half pain, half pleasure.

Her eyes roll back mouth opens wide. Sara kisses her as the moans start getting louder. Terris is moaning loudly but the constant kiss quiets them. Terri moans a bit louder Sara lifts her skirt drops her panties and shoves her clitty in

Terri's mouth. Terri starts sucking on pure instinct. Terri bucking back and forth between Keith and Sara. Terri's riding the spit roast like a pro moaning on Sara's clitty.

Keith is now balls deep. He holds for a minute allowing her body to adjust to his massive tool. Terri uses her newfound freedom to wiggle on it as she slides back and forth.

Sara pumps in rhythm as Terri attempts to adjust the position for comfort and pleasure. Terri slid a little more with each motion. Keith times her movement with her own and Sara's.

Soon they are locked in time and tune like impassioned lovers.

Alexis smiles, she is proud of her man's participation in the ritual.

Alice is so proud of Sara.

Alexis glows knowing that she is the one receiving that tool regularly. Terri is now moving and humping, sucking like a true sissy slut.

Everyone is smiling Terri's moans are all pleasure now. Terri continues to leak cum everywhere. Alice collects it in her hand. She feeds it to Terri he cleans her hand and continues to suck on Sara.

Keith is thrusting furiously. Terri is in time with them. Breathing heavily, Terri cums again, jetting her hot seed on the horse again. Alice collects and feeds him again.

Just as she finishes licking her hand clean. Keith starts to grunt. Terri feels his cock swell, and his hot seed jets inside. Keith pushes fully in ensuring all his cum stays inside her.

He softens slowly, Sara building to orgasm. Sara swells as Terri's oral service gets more passionate. Sara pumps in and out. Terri is desperate to get Sara to cum. Sara shudders and cums.

Terri's throat fills with Sara's hot cum. Terri cleans her clitty with her tongue. Sara smiles and kisses Terri's cum filled mouth. They snowball their kiss. Terri's well-used boipussy slowly pushes him out.

Terri's body and little hole quiver from being empty. Terri is exhausted and sore and very satisfied in a way she never imagined possible.

Release our newest sissy, boys. Ian and Keith release her.

Sophia says, don't get up just yet, Terri. Just relax for a minute.

The boys prepare the table. Terri just relax said Lisa. Lisa replaces her plug. Stay still, sweetie.

Keith and Ian finish the table prep. Boys, thank you. We can take the rest from here.

Yes, Mistress, they say. They slide their shorts on and exit the dungeon.

Terri, we are almost finished. Bree and Sara assist Terri to the table. Without a word, we stand her up.

Walk her to the table laying her down face up. A mirror above shows her well-used reflection; Terri actually smiles slightly, proud of what she's accomplished this afternoon. She should be. I would be I think to myself.

We lock her in. Lisa speaks. As your Sponsor, I am required to give you a special gift for your training. This gift is custom-made and special for coven members only. Are you ready to receive your gift?

Yes, Mistress.

Very well, Sabine and Alexis, would you please do the honors? Opening a cabinet in the corner, they bring out a stainless steel chastity. They bring out the chastity and several rings. They try rings until they find the correct size.

Sabine secures the ring in place. Alexis brings out a small tube. She removes the ball from his frenum and attaches the tube. The steel pulls out the jewelry, pulling the tube through the piercing. She trims both ends and very carefully, she slides the chastity over the softened penis.

They secure the tube to the ring. Alexis uses a fingernail to line up the piercing with an elongated slot at the bottom of the chastity. Sabine reinserts the stud and screws the ball on tightly with padded pliers.

Terri, Sophia starts, this is a very special chastity cage. I designed it myself. Its design allows partial erections. It should be comfortable enough for long-term wear. Your frenum piercing allows the wearer's erection growth but also the security that the soft penis can't escape. There is also a slot made for Prince Albert as well.

You, my sweet girl, have both. While it is not permanent chastity, it will be very difficult to remove without us detecting tapering with the piercings. The locks you could cut off, but again, we'd know. If you decide to remove it, the penalty will be no more Sara, no more Coven, and you will be out.

Do you agree with these terms, my sweet niece?

Yes, Mistress Sophia, I agree and understand.

That's my girl.

Sabine would call The boys and girls back downstairs.

Yes Sophia

Thank you, Sabine.

Keith and Ian open the double doors to the dungeon, and Carol and Becky walk in. The boys follow, closing the doors. Still bound to the table in a crucified fashion. Sophia makes a motion to Ian.

Ian hits a button. There's the whine of an electric motor, and the table starts tilting up. Once the table is standing upright. Becky and Carol inspect the newest coven member.

Sabine says welcome to the Coven sweet sissygirl. Do you wish for release?

Yes, Mistress Sabine.

What is your name?

Terri hesitates and thinks for a moment.

Sissy Terri. Terri says.

Very good. Sabine says.

Ian, Keith, please release sissy Terri.

First, her ankles are released. Ian says Terri, you are not going to be able to stand right away. When we release your arms you must grab on to Keith and myself.

Yes, Ian, and thank you both.

Ian releases the cuff, and Terri wraps her arm around one shoulder. Keith releases the other; she does the same and starts to fall. The boys embrace her and steady her.

Bree, Sara removed her boots, said Alice. We remove her boots.

Bree, Sara Becky says, take sissy Terri to my Room, shower her up first, and then a nice soak for you three in my tub. The bath is prepped and ready. You'll have 90 minutes. To put yourselves back together. No time extension. Get going!

The Mistress and I will use your room to clean up. Grab clothes, and whatever else you'll need for the three of you to be dressed for dinner. Dress is casual, but we want you girls dressed similarly and sexy. Yes, Mistress.

The leash is handed to me by Lisa. Go on girls, put her back together, relax a bit. We're making dinner. You three relax. You have earned it.

Thank you, Mistress Lisa, I said.

Great work girls said Sabine.

Everyone is smiling as we walk Terri upstairs. We go to my room again,.

Bree, can you start the shower? I'll my gear, then get her washed for the tub, then you get what you'll need. Sounds good Sara, I said

I steady Terri as I start the shower and the steam cycle. It heats up quickly. Sara walks in with 2 bags and her large purse. I put a shower cap on Terri.

Are you okay, baby? Sara asks Terri.

Still weak but I'm coming around.

Well, honey, in 90 minutes, you'll be right as rain and very pretty.

I start combing through my closet. I want casual, but I want sex tonight, too. I choose my pink latex jeans, a white camp shirt, and my VS pink lace bra and thong panty set. I add my black 5" Mary Jane heels.

I grab my makeup and enter my wife's bedroom. Sara is washing up Terri. Terri can stand but is still very weak. I drop my towel and step in.

I wash Sara's back and grope her cute little ass. She's wearing a crystal jewel stainless steel butt plug. I tap it a couple times.

She purrs Oh, baby, Sara turns, and we kiss. Mmm, that was nice, Bree.

Allow me to return the favor; I spin; she washes my back, gropes my ass, spins me around, and plays with my plug; then she drops to her knees and untapped me, and starts sucking me off right in front of Terri.

Terri's clitty grows inside her cage. The cage has room but not enough for a fully erect 9" penis. As Sara services me orally she reaches between Terri's legs and plays with his plug.

Terri cooos just like a girl. I shoot my load very quickly; Sara is very talented, Sara finishes washing up Terri as we show up, and we walk out together.

Come on, girls, the tubs await, I say.

Sara and I help Terri in the tub. At 5'9" tall Terri is 160 lbs. She isn't large or heavy, but for two sissies on HRT, it took some effort. We sit here in the middle of the tub.

Scented rose water fills our noses. The jets turned to maximum. Sara sits at the head, and I sit on the opposite side at her feet. Sara and I massage Terri's body.

The water is warm, and the jets feel great. Terri is responding, coming back to life slowly but steadily. I finish rubbing Terri's feet and start on her lower legs.

Sara, meanwhile, rubs her neck, shoulders, and upper back. She massages her chest and torso. I start on her thighs. I stay away from her crotch. As intimate as it is, there are some things that I will not do.

I ask Sara to rotate. She kisses Terri, and we stand up. We kiss, then rotate. Sara and my hair is washed and wet while Terri is still in curls and shower caps.

Terri, how do you feel, honey? Sara asks.

Much better still a bit sore but a lot better. Good, enjoy the water, honey. Bree and I need to get ready then we'll fix you up again.

Again? Terri asks

Of course honey, you're a sissy now. Sissiess are sissies 24/7 unless otherwise instructed. Which reminds me. You will need to start learning makeup and hair. We'll be back soon, baby girl. Relax and enjoy.

Bree, check this out for Terri! Mistress Alice and I picked it out. It's a pink padded bra and padded panty set, a white spandex half shirt, low riser denim skirt, and black 3" Mary Jane heels with ruffled anklet socks.

You do have pink makeup yes?

Girl, please... if it's pink or purple and MAC makes it, I have it. Bree, you are the best!

So are you Sara.

I have a feeling we are going to be good friends.

I hope so Bree.

Promise me one thing, Sara. Sure, Bree, anything.

Don't hurt Terri. I have seen her with girls before, and seen her heart broken. I dare say she loves you completely. After what she went through today I'd say she proved that.

My question now is what are you prepared to walk through whatever they throw your way?

I heard Alice talk about me pulling a train; another Idea I heard was being passed around the coven for a week; another was being the dungeon hostess for a week, maybe two. If that's what it takes, Bree, I will do it.

What are you wearing Sara?

This! It's a tennis outfit, a white, very short white skirt, a sheer pink half T-shirt with a white bra and pink thong. Pink 4" Mary Jane with ankle ruffle socks.

Sara teaches me how to get a high ponytail with my ringlets.

Oh, Bree, your hair is so nice to work with.

Thanks, Sara. Sara showed me how to do a subtle smokey with my pink.

Sure Bree! Can you show me how to do Ombre lips?

Sure honey, sit down; I do mine next to her in the mirror, okay now, you. The second time she tried it was perfect.

Okay, girlfriend,, we got 45 minutes to put Terri together. We walk in. Terri is sleeping in the tub, running full blast. I shut off the jets and splashed cold water on her face.

Up, sissy, time to move.

Hunn what? Bree, I had the strangest dream.

Check between your legs it's not a dream.

Oh my god, what is this?

What you asked for! Come on, the clock is ticking! .

.

We pad Terri dry. Just as I finish drying Terri. We have treat her piercings. I grab a wash cloth and dry them. Sarah comes in with a spray bottle of Bactine.

We tell Terri to pay attention because from now on, you will have to care for them. We adjust the piercings, clean them,, and treat them. Terri looks stunned.

Terri, are you alright, I ask?

I'm so confused. I thought it was a dream.

Sara asks did you like the dream?

Well, yes, it was my best dream ever.

Well, my love, now you get to live it. Let's get you ready, honey says Sara; she kisses Terri long, hard, and deep. She feels him up and down. She plays with his plug.

Terri baby I want to be with you. Do you want to be with me?

Yes, Sara,, I do. I just never realized how badly, until now. Sara, I need you. I pray you need me too.

I do need you, Terri my heart has been aching for a man like you. Sweet, gentle, kind.

Alright, Sara, let's get this sissy ready. Let's make our Coven proud.

What are my stepdad and brothers gonna say?

Terri, you need to learn one thing above everything else.

What's that?

Eff what anyone else thinks. As long as you are happy, that's all that matters.

You're right Bree! Mom and the Coven have my back; that's all we need!

That's the spirit, my new niece. Let's do this!

Leaving the shower cap on we start dressing her. Terri is back to full strength, with a can-do attitude. His new cage allows for a semi-tuck. With padded panties, there's no bulge. To aid in her tuck, there is an elastic waist strap in the bag with a band attached that holds the cage tucked. I hook Terri up.

Is it comfortable, I ask?

It's not bad, she says. Terri slides on the panties.

Now, the bra, can you clasp it, Terri?

Let me try, Terri has trouble.

Try this said Sara. Hook in front then spin it around. Now arm through. Perfect, Terri, she kisses him.

Terri I wish you had Breast said Sara.

Me too she says. Terri said I don't know where that came from.

It's okay. We are sissies; sissies keep each other's secrets, right Bree?

Yes, we do.

We slide the half-shirt over his head.

Isn't it a bit short? Terri asks

No longer or shorter than ours, honey Sara says as she spins like a runway model.

Terri sees the skirt; it, too, is short.

Baby said Sara, you're a sissy now. This is how we dress every day. Your gonna love it trust me.

Bree?? Terri says nervously.

Yes, Terri.

Is that true?

Yes, it is. Terri my sweet niece. You've known me my whole life, have ever seen me happier?

No, I can say I have.

Exactly! Who knows, maybe you'll want to be a full-time sissy or just learn to be a far more cultured person. Either way, you always have a choice, honey.

Be a sissy, be a full woman or a Pre‐op TG woman, or go back to being a man. The doors for you are open to do what you want to do. Let your heart guide you.

She slides on the skirt the waist just below her hip dermals.

I got an idea, Sara; keep going; I'll be right back. I knocked on my bedroom door.

Who is it?

It's Bree Mistress.

Come in honey. I close the door and curtsey.

Excuse me, my Ladies, I need some jewelry. I grab my necklace and locket, along with 3 stainless steel collars, all bangles, and some dangled body jewelry. Sara has a heart dangle so I grab my heart dangle and cute butterfly for Terri.

Thank you, M'Ladies. Spin and exit.

I return in no time Sara is talking Terri through makeup. She already finished his base foundation. She talks about contouring the foundation.

Was I gone that long?

No, not all, but now I know exactly what's required. It goes quickly. By The way, Bree, I am sold on this MAC makeup of yours. It's great stuff.

It's all I wear. That and a little Channel; they have great lipstick, too.

What did you get?

I got my heart dangle for my bellybutton and for Terri my favorite Pink rhinestone butterfly dangle.

It's adorable Bree! Terri said.

Thanks, the devil is in the details, sisters.

Yes it is girlfriend says Sara. We smile and giggle.

Do you like it,, Terri?

Yes, it's adorable.

Adorable?

Yes, adorable. I love it.

Can I put it on you?

Please, Bree, please, oh please. Its so pretty.

Terri's voice is getting higher and softer. She's giddy about the butterfly.

Okay, let Sara finish your face, and oh, I got another idea, Sara.

What she needs is a tramp stamp!

Oh, great Idea. Do we have time? Asked Sara.

We have 25 minutes. Mistress Becky keeps a few on hand for herself. Let me ask, okay?

Do you know how to put them on?

Of course, Sara, who do you think puts them on her? We giggle!

Terri says tramp stamp?

Really?

I'll Be right back.

Knock knock, it's Bree.

Come in sweetie. Closing the door I curtsey. Mistress, may we use one of your temporary Tattoos?

Of course. For Terri?

Yes, Mistress.

Use my large roses and thorns. There's a small kit for tiny tattoos; use a few. Make her sexy.

Yes, Mistress, Thank you. I curtsey and leave.

We are a go for tattoos.

Tattoos more than one?

Yes, Terri. If this works you will wear lots of temporary tattoos shortly.

Play your cards right; ink might be in your future, too! Here's the first one. It's 18" inches wide and 6" tall in the center, with 7 roses, with the largest in the center. It's red, green, and black.

I find the small kit. It has butterflies and hearts. I wipe her back with alcohol. Wet it down line it up carefully. Smoothing out gently.

Where do we put the others, Bree?

Behind and below her ears. The butterfly above her naval.

They come off easy, right? Asked Terri.

In a about week or two if you are careful. It takes a couple of days if you wash it daily. Mistress only buys the highest quality ones.

Do it, girls; make me look adorable.

There's that word again. If I didn"t know better I'd say she loves being a sissy. It can be addicting. Being a sissy isn't for everyone. It takes a special kind of person to be a sissy.

Terri is a special person. Smart, sweet, funny, open-minded. He's always been close to his mom. Terri always could hug people when they needed it the most. It's the kind of hug that boosts your spirits and fills your soul with love when it's needed most. Terri can still do it too. I called it a superpower. When Terri hugged me I felt it again. I am almost convinced they are soulmates. Time will tell.