A Weekend With Her

Story Info
Sissy is only allowed to watch.
3k words
4.53
13.3k
7
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Edward, this is my slave 'sissy."

"Whoa lady! I don't do none of that gay stuff. I'm not queer."

"Oh, don't you worry about that my love. I invited you up because I want some big black cock. Besides, sissy is my slave, and slaves are not allowed to have sex."

"Oh?"

"May I take your coat, sir?"

As I hang up his black leather jacket Mistress removes Her three quarter grey fox and hands it to me. I chance a quick cuddle of the fur as I carry it to the closet.

"Well, shall we get comfortable? Sissy, did the Champaign come? Lets sit on the couch and get to know each other."

"Shall I serve it Mistress?"

"Yes, sissy. Of course." Aside. "Such a silly sissy."

I've been serving Her one night a week and every third weekend for two years now. My wife knows, and if not actually approving, accepts my need, knowing no sex is involved helps. Besides after every session I come home horny as hell.

I know I'm not Her only slave. One time I watched Her fuck one of Her female slaves with a strapon.

She and Edward are kissing on the couch. She strokes the bulge in his pants. "Cheers." They sip their bubbly.

Soon his cock is out. My God, it must be two inches in diameter and a foot long!

Mistress kisses his knob. She kisses up and down his shaft. "Mm." She puts it into Her mouth. She takes it out of Her mouth. "Beautiful." She smiles up at him.

"Mm, mm, mm." She deep throats. Her eyes swivel to me to make sure I'm paying attention.

My clitty is crushed in it's cage.

Thursday we took the train from Montreal, and now are in a high end Toronto hotel. I used one of my 'floater' days to come and serve.

I put on my sexy maid's dress and cleaned the suite while She was at Her business meeting. Then I stood by ready to serve when She returned in the afternoon.

I held Her towel as She showered and helped her dress.

"I'm going out. You may order from room service. Look pretty when I get back, sissy."

I stand, hands behind my back, against the wall watching.

"Such a big boy." She kisses his knob and swallows. "Mm, mm, mm."

He holds Her down as he cums. "Mghh, ghh,ghh."

He lets Her up.

"Oo, like to play rough?"

After She left on her date I showered. She locked my clitty cage on before we left her condo yesterday and made a point of showing me She left the key on Her makeup table.

I put on my pink lace bra and pantie set. She made sure I packed my wasp waist corset. I love the feel of rolling and stroking nylons smooth, my clitty practically dribbles. So yummy! I slip into my square neckline short sleeve pink mini dress, then do my face.

Pale base, accent for my cheeks, slutty teal eye shadow and fake lashes. Slut pink lip gloss to match my pink nails.

Lastly, my painfully sexy four inch spike heel, pointed toe, shoes.

Mistress licks the dribble of cum from Her lips. "Sissy, go turn back the bed."

"Yes Mistress."

She comes into the bedroom as I sit on the edge of the bed and secure the leather cuffs to my ankles.

"Hands." She straps a set of cuffs to my wrists. The padded ones don't leave embarrassing marks.

"Grab the bar." She points towards the open closet door. She shackles my wrists to the bar. Next She lays the spreader bar at my feet. "Spread 'em," and shackles my ankles to it.

"Edward, you may come in now dear."

Oh my. He's left all his clothes in the other room.

Mistress wastes no time undressing.

"I'll lay crosswise like this so Sissy can see it all, as you nail me good and hard baby."

Edward smiles and climbs onto the bed, then guides his big cock into Her pussy.

"Oh!"

He begins pounding Her.

"Uh. Uh. Uh. Yes, baby. Uh. Uh."

She turns her head towards me.

"See sissy, this is how a REAL man satisfies a lady. Uh. Uh. Uh."

He keeps thrusting as he looks my way and smirks.

I know an inferior sissy like me will never be good enough for Mistress. That's what makes serving Her so wonderful. God my crushed clitty hurts so good in it's tiny cage.

"Stop, stop. Do me from behind."

They move around so Mistress is on her hands and knees facing me. Her beautiful red lips form an 'O' as he plows her pussy. Her eyes roll up. Her mouth opens and She squeals as She cums. God I wish I could satisfy a woman like that.

They catch their breath.

"Would you like to shower before you go, dear?"

"Sure."

"Go on then, I'll join you in a minute."

Without dressing she comes over and releases me from the spreader bar, then unclips my wrist cuffs.

"Take off your dress, leave your bra, panties and corset on, then come to the bathroom."

"Yes Mistress."

I sit as ordered on the toilet seat and watch as he nails Mistress to the shower wall.

"Your money is on the table by the door."

"Thank you, mam."

"Oh, thank you. I'll give you a call next time I'm in town, dear."

After he left She pointed at the hotel's big fluffy white bath towel. "Come, dry me off. Then I'll allow you to brush my hair."

"Thank you Mistress."

It was so exquisitely painful. My clitty was crushed. I patted my Goddess dry with the soft towel, then brushed Her silky silver hair. Beautiful now, in Her twenties She must have been drop dead gorgeous.

"Come."

We went to her bedroom and She selected a knee length puff sleeve white satin nightie with a ruffle of pink satin around the collar and hem.

"Hold it up for me."

"Yes Mistress."

She slid into it.

"Hands at your side."

She took a selection of satin sashes and bond me from my ankles to shoulders.

"On the bed."

"Yes Mistress."

She got into bed, kissed my cheek, "Goodnight sissy." and rolled away from me.

"Good night Mistress.

I lay there in delicious frustration as my Mistress dozed off. Why do I serve, worship and, yes, love Her like this? Who am I kidding? It's because I need Her discipline like a heroin addict needs his horse.

Saturday we had room service bring breakfast. Then I held Her towel as She showered. She let me fasten Her bra for Her. She let me smooth Her nylons up Her gorgeous perfect legs.

I watched as She put on Her maroon mid calf length skirt and fasten it's wide red leather belt. Would Her belt kiss my back tonight? She pulled her cream angora turtle neck sweater over Her head and selected earrings and a necklace. I watched as She did Her face.

I was wearing my sheer purple panties and sissy bra. On my feet my four inch spike heel ankle straps were secured with the shiny little gold padlocks.

"Fetch my switch."

"yes Mistress."

I got to my hands and knees. Then She gave me ten. My morning discipline.

"Speak."

"Thank You Mistress."

"And?"

"Mistress please let me serve you. I promise to do everything in my power to please You."

"Chin up...By accepting My collar you agree so serve me, obey me, and I will in turn use you any way I see fit."

"Yes Mistress. Thank You Mistress."

At Noon. "Sissy, put on your blue print blouse, your blue plaid mini kilt and Lisa wig. We'll go out for lunch."

She wore her oxblood leather trench coat. I wore my slutty pink bomber jacket with the wide pink faux fur collar.

Cosmopolitan city. Nobody paid attention to my collar or padlocked shoes. We took a cab to a mall, ate in an Indian restaurant, then shopped 'till late afternoon. Lady shopping, we didn't actually buy anything.

I hailed a cab for Mistress and She told the driver where we wanted to go.

"UM, lady, you know that's the gay neighborhood? It might not be safe."

"What, a gay fairy might rape me? Please. Just drive."

We walked around until Mistress saw a restaurant/bar she liked the look of. We got a table. When the waiter minced over She ordered a white wine for herself and a tap water for me.

She sipped and discreetly looked around.

"Over at the left end of the bar, sissy. The girl with the purple rat tail? See who I mean?"

"Yes Mistress"

"Go buy her a drink. Go!"

"Um, Hi. How are you? Um, can I buy you a drink?"

"Huh. Sure faggot, why not. If you want more it'll cost you.."

"They call me 'Sissy', what's your name?"

"Poison. Got a problem with that?"

Poison wanted a beer, and I took advantage of my position to get a glass of red wine for myself.

"Cheers."

"Huh, ya cheers."

"Poison is a cool name."

"Did you just say 'cool'? What kind of a geek are you, faggot?"

"Um,ah, um."

"What's your game faggot? Want me to find a cock for you to suck? It'll cost you more than a beer, queer."

"Um, no. Actually, see the lady at that table in the corner? Um, would you like to join us over there."

"Sure, why the fuck not."

We went over.

"Mistress this is 'Poison'."

"Sit down, dear. Like another beer or a glass of wine?"

"Ya, thanks. Wine sounds good."

"Sissy, go get a bottle of this wine, and another glass for my guest."

"Yes Mistress."

"Quite the faggot you've got there lady."

"Yes, she's good obedient girl. So, are you free to join us tonight?"

"Not free lady. A gal's gotta eat."

"Of course dear. We were just about to order dinner. Join us and we'll talk about compensation. And dear, you may call me 'Sandra'."

By the time we'd eaten they had settled on a price for Poison's company."

Back at the hotel we didn't go to Her suit. Instead to the single room Mistress had booked for tonight.

"Sissy. Turn the chair around."

"Yes Mistress."

Mistress took the sashes from Her purse and bound my arms and legs to the chair's arms and legs. "What do you think, Poison? Shall we gag sissy or not?"

"Never seen a real one."

"Here, you do the honors. Get the straps nice and snug."

"Hey? What's that on his dick?"

"Don't touch, dear. Sissy is in chastity. She's denied any pleasure."

"Wicked."

Mistress tells Poison to sit on the edge of the bed. She turns the music on. She sways in a very erotic way as she strips for Poison. My God, Mistress is so beautiful. She's built like the proverbial brick shit house. She moves so fluidly. Was She a dancer? Her hands caress her ivory skin. Poison's cynical expression changes to one of arousal.

My clitty cage is so tight!

Mistress rolls poison's nipples between her thumbs and fore fingers. Poison's no longer the street hardened dyke. She's surrendering to Mistress.

"Uh!"

"You like that, don't you?"

"Mm."

"Are you going to be a good girl and eat me 'till I cum?"

"Yes. Yes Mistress."

Mistress sat beside Poison and spread her legs. She gripped the girl's rat tail and pulled her off the bed. God it was hot!

Poison got right to it. Licking and kissing.

"Good girl, you're doing fine."

My clitty ached so good.

Mistress closes her eyes and lays back on the bed. "Keep going girl." She rubs Poison's shaved head. "Mm, good girl."

God, to be Poison right now.

"Mm, ah!" Mistress cums.

"You deserve a reward. Lay back on the bed."

From Her big purse Mistress takes two satin sashes. She secures Poison's wrists to the headboard. Poison's expression changes to a bit of fear and a bit of curiosity.

With Her beautiful long manicured nails Mistress starts tickling at Poison's feet. Slowly she edges up her legs. Poison writhes and shrieks in pleasure. My clitty is dribbling.

Mistress reaches Poison's mouth. She pokes two fingers at her lips. "Suck, baby. Suck like it's a juicy cock."

Poison licks and sucks. By God my clitty is in pain. Mistress fucks Poison's face with her fingers. "Suck you cheap slut. Suck."

Mistress digs into Her big purse again.

"You deserve reward, my pretty."

She pulls out Her big gnarly purple dildo.

"paying attention sissy?"

"Ghh." I reply.

"Watch closely. This is how you fuck a slut."

She rubs the purple knob along Poison's lips. "Lick it slut. Make it nice and slippery."

Poison licks and sucks the knob. She licks up and down the shaft. Long, tongue licks.

Mistress slides it down past Poison's chin. Along her throat. Down her chest. Round and round her little mouthful size boobs in a figure eight. Down across her tummy. Poison is quivering.

So am I. God it's so erotic. Mistress looks at me and smiles. She licks Her lips.

She rubs the knob along Poison's cunt lips.

"Ah!"

"You want it, don't you slut? You want it deep in your cunt. Beg for it."

"Please, please give it to me."

"Give what to you?'

"Your cock. Please Mistress, fuck me with your cock."

Good girl."

"Aaahh!'

Mistress slowly, slowly, buries the big purple cock in Poison's pussy. Mistress strokes it in and out. Then she fingers as she pumps. She fingers Poison's clit.

"Ah. Ah! Ah! Um! Oh." Then she cums with a squeal.

"See, baby? If you were my slave, I'd reward you for good behavior.

"Don't I reward my slaves sissy?"

"Gh,mgh, gh." Only the female ones. She never rewards me. My clitty dribbles and my balls turn blue, but She never lets me cum.

Mistress releases Poison's wrists and puts the sashes and dildo into Her purse.

"Untie sissy, but leave him gagged."

She pulls my leash from Her purse and snaps it onto my collar. "The room is paid for, dear. Stay the night if you want to. Here's my card. Email me before Wednesday if you want to serve. Come sissy. Carry out coats."

Back in Her suite Mistress had me strip to just my gag, sheer purple panties and spike heels, after hanging our coats up.

"Come, sit with me."

She lays a soft angora wrapped arm over my shoulder. "You've been a good sissy today."

"Gh mg."

Her hand cups my sissy boy breasts. She rolls my nipples. Then she pinches my right nipple. Playfully at first. Then Her nails dig in.

"GH!"

Her pincer grip tightens and she pulls.

"Nice little sissy nips."

"GHH!"

"Oh, sissy," She admonishes. Then she repeats the teasing then pinching and pulling on my other nipple.

"GHH!"

"I do love seeing the longing in your eyes when I'm being pleasured. You'd like to be the one pleasing me wouldn't you? You'd like to be the one kissing my pussy."

"Gh." I whimpered.

She lifted my hand to Her breast. "Isn't angora soft? I bet you'd like to slide your sissy pervert hand up under my sweater and molest me. I bet if I asked you'd drop between my knees and eat me out, sissy."

"Mmg." Would I ever!

"I know what you'd really like. If I got my big purple girl cock, bent you over the edge of the bed and buggered you."

"MMG!" NO!

"What? No,no. No use begging for it, my love. You might enjoy it, and we can't have that. Besides, I promised Laura I'd never let you cum."

Laura? She's talked to my Laura?

"We had a long talk about you sissy. She really does love you. You know how lucky you are? She said as far as she knows you've never had anal. Never been pegged. Is that true?"

"Mm." I nod my head. She talks to Laura? About our love life?

"Laura seemed interested in the idea of having a sissy maid."

Shit.

"Anyway sissy, time for bed. Come."

I follow Her to her bedroom, where She pulls Her soft sweater over her head.

"Un-clip my bra, sissy."

My fingers quiver. She shrugs it off. I lay it by Her suitcase. She lifts Her arms.

"Take off my belt."

I release the buckle and pull it from the loops. She holds out her left hand. I present it to Her.

"Perhaps a bedtime whipping? I just bought this belt last week. Break it in?"

I whimper.

"Maybe before breakfast? Take off my skirt."

As I put Her skirt aside She sits on the edge of the bed.

"You may remove my shoes and stockings. You may caress and kiss my feet."

Oh Goddess! I'm in wonderful excruciating pain as my clitty strains for release and I touch Her beautiful legs.

"Enough! Go prepare my shower."

I hold Her towel as she showers. I must pay attention as She soaps and caresses Her body. She rinses off and I gently towel Her dry. I'm in so much beautiful pain.

"Go put on your nightie and lay out the sashes."

Again She binds me. She cuddles me, gives my balls a little squeeze, then lays back and masturbates until She cums.

"Mm, that was good." She turns out the bedside light and is soon sleeping soundly.

In the morning I help Her dress after Her shower.

"Put on your little pink dress, we'll go down for breakfast."

Before we went back to the suite She arranged for Her bags to be taken to the train. I packed and was all ready when the porter arrived. He followed us to the underground shopping tunnel that leads to the station.

Mistress sent a text when the train arrived back in Montreal.

I gasped as we entered Her building.

"Come up Laura. You've a lot to learn about the care and discipline of your sissy maid."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

Things Happen at Weddings A sultry bridesmaid makes the reception interesting.in Fetish
Game Night Wife takes control in a new game.in Loving Wives
Night Flight A young couple meets a seasoned FLR mistress on a plane.in Fetish
My Wife Found My Chastity Cage Wife makes a discovery.in Fetish
Summer Camp for Naughty Husbands Ch. 01 Steve learns more about his loving family.in Transgender & Crossdressers
More Stories