Susan's Holiday

"Mistress, please, I'll, I'll never disobey again."

"Shh darling. I didn't give my sissy slut permission to speak." I keep my voice soft and sweet. This is my first face to face with this thing.

I got into my hobby in a round about way. I took hairdressing and cosmetics in community college. One of the very classy clients at the salon I worked at suggested I take a night school course in elocution and grammar. Said my low class accent and speech was keeping me back. She was right. When I started saying 'yes' instead of 'ya' or 'yup' and 'thank you' instead of 'OK', or "how can I help you today' instead of 'whadda ya want this time' my tips improved, and even more important, Margaret, the owner noticed and offered me the receptionist/ cashier's job at the up scale spa she opened.

That's where I met Linda. She's a nails artist, came from another of Margaret's salons. The two of us hit it off right away. Once or twice a month we'd go out clubbing and dancing.

Well, one of her clients told her about a club out on the east end. Said it wasn't much for dance music but lots of interesting people watching. We were both off the following Wednesday and Thursday, so we went straight from work Tuesday.

The food was OK, the music so so, and the bar tender generous with the shots. Some of the guys and gals looked like they were looking to pick up some work on their backs or knees. Lots of fun.

So, this man comes in. Middle age. Dressed like a successful business man on the prowl. He heads towards the bar, looking around at the meat available.

Then the oddest thing happens. He looks our way and literally turns white and shrinks. He comes over to us with his eyes downcast. He kisses Linda's hand. "Mistress Sabrina, hello."

"Leave here, do not return tonight, bitch."

"Mistress Sabrina, yes right away Mistress. Thank You Mistress."

He literally scooted out the door without even a glance back.

"Mistress Sabrina?"

"Well Sues, guess it's time to tell you about my paying hobby."

Now it's my hobby too. Gentlemen meet me online and pay me, 'Mistress Caroline', to train and discipline them. if they are interesting I let them worship me in person. I allow them to buy me gifts, if they are obedient.

Let's call this one 'Bobby'. It's age, early sixties, divorced, no children (adult or child) and retired from the military. He's a closet sissy. Five six, trim build. Wears pretty clothes and makeup well. Craves discipline.

For the next four days I will allow him to serve and worship me aboard the charter catamaran he's rented in the British Virgins. He/She even sent business class tickets. Good slut. First a flight to San Juan, then a commuter flight to Tortola.

When I came out the arrivals gate at Beef Island Airport there she was, dressed as instructed. Three inch spiked heels, skirt at least four inched above her knees, bare midriff blouse, and slut pink lip gloss with a bit too much purple eye shadow.. Yum.

I pointed to my checked bag and handed her my carryon. If anyone noticed they probably thought the elegant lady with the pink fur jacket over her arm was kissing her girlfriend's cheek as I whispered "Lead me to the limo, slut."

And that's why she's being disciplined.

"Mistress, we're anchored in Trellis Bay. It's just across the road. Come, we'll have a 'welcome to the islands' rum punch, then dinghy out to the boat."

We had to take off our heels to walk on the sand. The rum punch was good.

First thing I did when we got to the boat was change into my bikini and dive into the water. I toweled off, then went to my cabin for some toys.

"You did remember the Champaign?"

"Yes Mistress Caroline."

"Well?"

"Coming right up Mistress."

She must wear heels quite a bit. Nice wiggle. We'll see about that.

"You brought two flutes. Am I expecting company?"

"Um. Sorry Mistress. Er, may I serve you Mistress?"

"You may."

It was good quality Champaign. Bobby nervously eyed the toys I'd arrayed on the cockpit table.

"Take off your skirt and blouse dear."

"Yes Mistress."

"Bra and panties too."

"Yes Mistress Caroline."

"Mm, your clitty cage is much too big. Change into that one and bring me back the key." I pointed to the steel bar one I brought for her, it's cage not much bigger than a mushroom top. She was gone for a while.

"Key."

"Yes Mistress Caroline."

"Refill."

"Yes Mistress." She topped up my glass.

I snapped my fingers and pointed at the other end of the settee. "Sit."

"Yes Mistress."

"Feet."

"Yes Mistress."

I strapped the satin lined black leather cuffs with the nine inch chain between them to Bobby's ankles. That should make things entertaining.

"On your knees."

"Yes Mistress Caroline."

"Well, my little sissy slut. Let's start with a little discipline so my bitch knows what her week will be like. Eyes on the deck.

"Where will we start? Last month you did not check in for twenty four hours."

"Mistress, I explained, I was.."

"Quiet darling. You did not ask permission to speak." I kept my voice low and sweet. Things have to know they are not worth my having to raise my voice for their useless selves.

"You did not send me a birthday card. Finally, I specifically said you were to supply limousine service from the airport." I reached for my riding crop.

"Mistress, please. I'll, I'll never disobey again."

"Shh darling. I didn't give my sissy permission to speak. I guess my slut forgot rule five. Tell me sissy, what is rule five?"

"Rule five? Um,um. Rule five, yes!. A slave must never refer to itself in the first person. A slave is a thing that belongs to it's Mistress."

"I think ten will be sufficient for my brainless fuck toy to remember. Open up."

I deliberately snugged the ball gag just a bit too tight. "Stand up slut."

That was fun. Watching her struggle to her feet in heels and hobbled. Oh look, drool is already dripping down her chin.

The driver's seat is up a step so the driver can see over the cabin. "Reach up and grip the driver's seat back ."

I love this part. Awakening my slaves to the reality of punishment on their virgin voyage to 'in person' BDSM. Bobby slut has a beautiful scream, even gagged. Cute whimper.

"OK. Put your bra, skirt and top back on."

While she was doing that I went to the kitchen and got a bowl. I put some ice cubes and water into it.

"Refill my glass." I set the bowl on the deck.

"Mmg Mnnght."

I removed the gag. "Down and drink."

Her long blond wig dipped some ends into the water as she lapped. I lifted the hem of her skirt and rubbed her white tush. "I brought my big black girl cock. Guess where it's going? My slave sluts tight little ass cunt." Did I detect a whimper? "Of course we'll work up to it. I also brought my pink nine incher, and my purple foot long. We'll have lots of fun."

I gave her a sharp slap on the ass. I sat back and finished my drink. I took my time. Then I allowed her to get off her hands and knees.

"Go make supper. You may eat with me tonight slave."

"Thank you Mistress Caroline."

My sissy is a good cook. A salad with avocado slices. Tuna steaks with rice and peas, and a white wine. As we ate I explained how her week would be. I explained she would be used for my pleasure. I explained her clitty would stay caged. If she came, it would be from anal stimulation. Excitement, fear and disappointment alternated in her eyes.

Bobby took bean bag chairs up front to the trampoline for me, then did the dishes.

"Mistress Caroline, the dishes are done and put away. How may I serve You?"

I stood and unwrapped the silk sarong I wore at supper, just enough to slide off my bikini bottom. I sat back down and spread my legs. "You have been a very good slave. Come and get your reward." I pointed down.

Bobby's cunt eating was adequate. Good, but could use some coaching. But that's OK, we've got all week.

After a nice orgasm I let her up.

"Your Mistress has had a long day. Go to your room. In the morning wake me at eight. Wear the cute pink baby doll with the satin trim you wore in that picture."

"Thank You Mistress Caroline. Good night."

Such a nice sight. Bobby's clitty was bulging out the bars if it's cage. I fondled those nice hairless balls. Sweet whimper. "Off you go. Have the coffee ready when you wake me."

I was half awake at eight.

"Good morning Mistress Caroline."

What a pretty sissy slave. Face made up. Sweet little nightie. Still hobbled, wearing pink two inch heel sandals.

The yearning in my slave's eyes as I tossed the top sheet aside and languorously stretched, letting her have a good look at my naked body spread out on the mattress.

"My robe slave."

"Yes Mistress Caroline."

She held my ankle length puff sleeve black robe of gossamer thin material. I love it's soft feel and that it hides nothing. I do have a beautiful desirable body, if I do say so myself. One of the joys of being served in person is knowing my subs will be constantly aroused and frustrated by my unobtainable perfection.

I allowed Bobby to join me for breakfast. I didn't dress for breakfast. I'm such a tease at times.

"Bobby."

"Yes Mistress?"

"I want to go for a sail today. Right after you clean up the breakfast dishes."

"Yes Mistress. May this slave ask a question Mistress?"

"Go ahead, ask."

"Mistress, do you have any sailing experience?"

"No, why?"

"Mistress, let me explain. A sailboat has some things that can hurt you if you don't know what is going on. As captain I want you to be safe, so, if I say 'do this' or 'don't do that', when the boat is underway, do as I say. If you don't understand why, do as I say first, THEN ask why. As captain I'm responsible for the ship and all aboard her."

"Slave, I understand. Now bring me a wide leather belt."

"Mistress, pardon?"

"You heard me. A belt."

She fetched me a nice two inch wide brown leather one. I put the buckle in the palm of my hand and wrapped the leather once around my fist. "Hand and knees on the deck." I lifted that sweet little nightie up onto her back, then pulled her panties down.

Five on that white tush satisfied me for the time being. pretty red ass.

"Rule twelve. Speak."

"Mistress, thank you for correcting Your slave."

"Go get dressed and lets go sailing, bitch."

"Yes (whimper) Mistress Caroline."

My sub wore deck shoes, but a very cute powder blue sun dress with an impressive set of tits, and a short brunette wig.

We sailed around Sir Francis Drake Channel. Bobby pointed out the different islands. There were lots of other boats, sail and power out on the water. The sun was shining, the temperature in the high twenties(C), the breeze refreshing.

"Mistress, may this slave treat You to lunch at the Cooper Island Beach Club?"

"Why Bobby, that sounds wonderful."

It was fascinating. Bobby showed me how to help 'pick up a mooring'. Which was a round float with a line on it we tied our catamaran to, then we dinghied ashore.

"Very well done Mistress. This thing is now your slave again."

The resort was nice. We were seated and the waitress took our orders. I ordered a rum punch to start. Bobby an ice tea.

At the next table were three ladies and two men. I noticed a cute little red head looking at us, but averting her eyes when I looked her way. Their table had several extra chairs. What the hell?

"Hi, I'm Caroline, this is Bobby. Could a couple of gals joint the party?"

"Sure. The more the merrier. I'm Sylvia, this is Tom. They're Brad and Vicki, and that's Maureen."

I sat next to Maureen.

"I'm just going to be rude, "said Sylvia, "but this is the modern age. Are you two just friends, or like, um, more than friends?"

"Sylvia!"

"It's OK Maureen. Actually, I'm a 'dom' and Bobby is my 'sub'. Bobby belongs to me. Isn't that right Bobby?"

Blush. "Yes Mistress Caroline."

Just then the waitresses brought the food order.

There was a minute of silence as everyone studied their plates.

"Well, Cheers everyone. Here's to a wonderful vacation, and new friends!"

That broke the ice.

"So, like, how's that work?"

"Simple, I tell Bobby what to wear, what to do, and how to serve me, and she obeys."

"Um," said Brad, "are you a guy in drag?"

"Answer the man, dear."

"Yes. I'm a cross dresser, sir."

"And Caroline's," finger quotes, "sub."

"Yes sir."

They asked a lot of questions. Some too personal to answer. As we talked I lay my hand on Maureen's thigh. She blushed and lay her hand on top of mine.

I was soon time to go. No doubt they'll have some wild stories to tell their friends back home about the strange couple they met. They insisted on buying our lunch. What nice folks.

We sailed away. Later we anchored in Virgin Gorda's North Sound near Prickly Pear Island. After Bobby dove to see that anchor was set, he taught me to snorkel.

We just were toweling off when a little inflatable like ours came over from a boat the same as ours anchored just over there.

"Hi, remember us?"

It was Maureen, Sylvia and Vicki. We all laughed.

"Sure, come aboard, Bobby was just about to open a bottle of bubbly."

"Great! We were just coming over to invite you to our boat for supper."

We had a few drinks. Maureen sat across the table from me. her foot slid up my leg. Shy smile, then she blushed and looked down.

They finished their drinks. "Come over about six."

"I'll stay here and ride back with Caroline and Bobby, if that's OK with them."

"Tired of us old married fogies so soon Mo?" They laughed. We saw them off.

"Bobby, another refill."

"Yes Mistress Caroline."

"Come Maureen, sit with me."

"Thank you Caroline."

"So, I take it you have more questions?"

"Well, um, like, how do you get, like, subs?"

"Thank you Bobby. You may join us."

"Thank you Mistress."

"Now that depends what you're asking. Do you want to become a dom? Or are you interested in serving?"

"Serving, um, Mistress Caroline. But er, I don't know exactly what that entails."

"Bobby, dear, do you have a set of printed out rules with you?"

"Yes Mistress."

"Go fetch them for Maureen to read, slut."

Her one piece pink and white wide vertical striped swim suited her fair complexion. I've never had a female one. Wonder what her scream will sound like? Oo, look at that sweet blush. Wonder if she knows what I'm thinking? I slip the tip of my tongue between my lips. Oh yes. She knows.

We took Maureen and a couple of bottles of wine over to their boat. It was a fun evening, but by the time we got back to our boat I was in the mood for some lovin'.

"Slut, put those bean bag chairs out front, then go change into a pretty nightie for me."

"Yes Mistress Caroline."

I changed into my purple satin teddy, and brought my strapon harness and my nine inch cock.

I pointed to the other bean bag. "Sit down slut. Relax."

"Thank you Mistress."

I stood up. "You've been a very obedient slave today."

"Thank you Mistress."

I sat across Bobby's lap. "A very good girl." I kissed her. Mm good kisser.

"Those were nice people weren't they?"

"Yes Mistress."

"And now I know you only live an hour's drive from me. If you were telling the truth when they asked where we lived."

"Mistress that's the truth."

"So I could come to your home and use you just about any time I wanted."

"Mistress, your slave would love you to come and use it any time."

I picked up Bobby's free hand and held it to my left tit. I kissed her, deep and hard.

"Know what I'd like slut?"

"No Mistress, what can your slut get you?"

"I'd like you to bone me doggy style right here in the trampoline under the stars." kiss. "Would you do that for me, slut?"

"Yes. Yes of course Mistress. Anything to please you."

I got off his lap and picked up my strapon. Bobby looked confused, then it dawned on him as I handed it to him.

I got down. Bobby slipped the pink rubber pecker into me. Mm. Nice slow strokes. His hands gripping my hips. "Harder faster bitch! Drill me slut!" Did he ever.

Then he used his own imagination. A hand slipped down. A finger found my clit as he drilled. Oh My God! But he didn't finish there.

"I love you Mistress Caroline." Then he scooped me up and carried me to my cabin. He gently lay me down and ate me to another big O.

"Mm, sweet bitch. Get up here and cuddle me." Bobby was a good cuddlier too.I offered her the privilege of sleeping with me "Yes please Mistress Caroline."

"OK slut, go use the bathroom. I don't want my sleep disturbed."

When she got back I bound her wrists with the cuffs, their long chain behind her neck, so her hands couldn't go below her belly, then pushed her on her side and snuggled up to her.

The light was just turning the sky through the overhead hatch grey when I woke. I felt mellow and rested. Bobby was laying on her back gently snoring. I fondled those shaved balls and watched her clitty try and squeeze between the bars of her cage. "Slut? Bitch? Are you awake slave?"

"Mgh, mm, hah. Oh, Mistress Caroline. Oh, Good morning Mistress."

"Good morning my pretty." I un-clipped her wrist cuffs. "Go use the bathroom, start the coffee, then come back here and hold my robe."

"Yes Mistress, right away."

"Mistress Caroline," we were just finishing breakfast, "may I ask you a question?"

"Go ahead."

"Mistress, do you like lobster?"

"Yes, of course. Why?"

"Well, we could sail to Anagada and have a lobster dinner tonight."

"That sounds nice. Now. Over the bench"

After a good morning spanking with the wooden spoon from the galley to remind Bobby she was my slut, not my girlfriend, and of course, because I enjoyed it, we got underway.

We left North Sound and sailed towards, well, nothing. An empty ocean. No island in sight.

I wore a long sleeve pink coverup over my bikini. My slut, her blue sundress. I pulled her arm over my shoulder as we sat together at the helm. My bitch gave me an affectionate little hug. I could get used to this.

After a while she said, "Mistress, see that dark streak ahead just on the horizon? That's Anagada." It was a bit of a tease as it seemed to take a long time to get there. We eventually picked up a mooring.

"My sweet Mistress will be a sailor yet. You grabbed the buoy like an expert,"

We went ashore and Bobby rented a cute little jeep thing called a 'Moke'. Then we went to a restaurant and made a dinner reservation for seven.

The rest of the day we puttered around the small, flat, sandy, island, from beach bar to beach bar. We had lunch at an up-scale resort on the Atlantic side.

As I enjoyed my conch salad and white wine I reminded my slut, "you know what I still haven't done Bobby?"

"Mistress?"

"I still haven't taken my bitch in her ass cunt. We'll do that tonight. You can wear your sexy little baby doll, your long blond wig, spike heels and some nice slutty makeup."

"Mistress, anything to please you. Losing my virginity to my Goddess will be an honor."

Bobby actually looked like she meant it.

We had a romantic dinner as the sun set across the harbor. Then back to the boat.

I wore my long chiffon robe and my nine inch cock. Bobby looked so sweet in her pink baby doll, heels and slutty makeup. Cheap little whore. Yum.

"Fetch me a rum punch, slut."

"Yes Mistress Caroline."

"Kneel." I pointed to the trampoline in front of my bean bag chair.

"Yes Mistress."

I sipped my night cap in my right hand as I stroked my girl cock with my left. Bobby knelt, back straight, eyes down. Silent. Perfect. I took my time. Wish she had real hair. That long blond hair does look slutty enough though. Mm.

"Like a taste of my rum punch, slut?"

"Yes Mistress Caroline."

I dipped my finger into my glass. "Come, suck it." I held my finger towards my bitch.

What a pretty sight. So obedient. I dribbled some on my girl cock.