CHAPTER 1
Birthday Girl
of that old ass muncher.
A manse in Hanalei, Kauai.
I was looking out through the large glass door that faced the beach.
The ocean has a special beauty at night.
I felt her sudden presence behind me.
Then felt her aged, wrinkled claws up my sides. Then on my breasts.
Felt her hot breath on the back of my neck.
“You are so beautiful,” she said.
“Thank you, ma’am,” I replied.
Her creepy old fingers found my nipples.
Pinched.
“You did well today,” she said.
“Thank you, ma’am.”
“It’s not easy. One’s first time with a dilator back there.”
She pinched again. Said …
“Ankles.”
“Yes, ma’am.”
I pulled the flimsiest, laciest black panties ever made down to my ankles.
Her hands moved back down my sides. Cupped my ass.
The wicked witch of the Pacific.
Kaipo.
She was the woman who had taken Master’s virginity. His first fuck.
She was 59 then. He was a teenager.
She’s 70 now.
And that’s why I’m here in Hawaii with my asshole so sore I could cry.
I’m Master’s birthday gift to the woman who introduced him to the wide world of sex.
Here’s the first words she said to me:
“I was told by [Master’s first name redacted] that I couldn’t destroy your asshole. So I won’t. But just about, dear. Just about.”
Kaipo likes to play anal games.
CHAPTER 2
Night Night
She put me to bed in a small, nearly bare spare bedroom.
The only things in it were a twin-sized bed with black iron head and foot rails and a small wooden nightstand.
After telling me to remove my stilettos, she told me to grasp the foot rail. Then she walked over to the nightstand and opened up the sole drawer.
And took out a nightmare.
I had seen one before in real life. And many times in porn.
And this one my growing horror recognized, was for me.
A lockable solid steel butt plug.
My knees nearly gave way.
If case you’re unfamiliar with them, their key feature is that, unlike regular steel butt plugs, these are mechanical. After anal insertion, they open up like flower petals once a knob is twisted.
That makes them impossible to remove as long as the knob is in the open position.
And here’s the hallmark of that wicked device.
You can use a key to lock the knob in the open position!
No key, no closing the metal petals. No key, no removing the butt plug.
And it got worse.
Out of the drawer also came handcuffs, a length of chain and a padlock.
And that’s how I slept my first night in the Paradise of the Pacific.
Handcuffed on a small, uncomfortable bed in a spartan room, my asshole stuffed with an unremovable steel butt plug that was chained to the bed’s foot rail.
Sweet dreams, everyone.
So, a rough first day and night in the Rainbow State.
But …
Kaipo was true to her word.
She didn’t destroy my asshole.
She distressed it. Loosened it. Sacked, raped and plundered it.
I’d never been so mad at Master.
It was a long week. The only wonderful thing there, besides the weather, was Kaipo’s granddaughter.
Kaleikaumaka.
I’ll have more on her later.
Let’s just say I’d never met anyone who made angry fucking such a point of pride.
CHAPTER 3
Kaleikaumaka
“Open.”
I did.
Her hand slid over my aching ass, which her riding crop recently turned rosy red.
And then between my now spread legs.
I exhaled sharply.
This girl had talent. She just attached a clamp to my clit with one hand and without looking.
A beaded clamp, I later discovered.
“Lift.”
I did.
Using my elbows to raise my upper body.
Her other hand found my right nipple.
Pinched.
Found my left nipple.
Twisted.
I gasped.
“I think I’m going to fuck you,” she said.
Not surprising. I was, after all, lying on a bed in her grandmother’s manse butt naked except for a black leather dog collar and black stilettos.
But apparently it did surprise her.
“I was sure I was just going to hurt you. But not fuck you. I even told my buddy Savannah not to bother coming over because I wasn’t going to fuck you.”
She laughed. Twisted both my nipples.
Punched me hard in the back where a kidney was.
Laughed again.
“And if I wasn’t going to fuck you, she sure wasn’t.”
Her voice became more matter-of-fact.
“But you’re hot. I want to fuck you. Roll over.”
She face fucked me.
For hours.
Pressing that creamy young pussy into my mouth and nose.
Grinding.
Smothering.
Edging.
Screaming with a cooof hard cums.
Kaleikaumaka.
Dear god.
Kaleikaumaka.
She made my stay in Hawaii bearable.
CHAPTER 4
Feeling the fill
All that, and much more, happened on my third day at Kaipo’s manse.
But first, let’s bring order back to the proceedings.
Second day.
After that awful night in metal anal bondage.
It quickly became evident that Kaipo had no interest in fucking me.
She just wanted to play with my shitter.
But I would be well and often fucked that week. By five women and four men.
The second day was mostly spent on what Kaipo call “hold discipline.”
Enemas.
One after another.
Most of the day. Minutes stretched out to millenniums.
Dr. Yoshida was an old crone who worked for Kaipo and may or not have been a retired medical doctor. She said she was. I had my doubts.
She was certainly one of Kaipo’s acolytes and henchwomen.
The bad doctor handled the enemas — and, I gathered — other doubtful medical procedures on Kaipo’s compound.
I had to pay for the privilege of her ministrations by going down on her a couple of days later, eating out both her pussy and her asshole.
It was very steamy. But only because she had me do her in the manse’s steam room.
The reason it was so very unerotic was that Dr. Yoshida proved to be a hallmark for me.
At 83, she’s the oldest man or woman that I’ve fucked.
But enough of her and more of what she did to me.
The space we were in looked a lot like a doctor’s examination room, only about twice as big. While I was being filled I lay on my side on the exam table, a soft ochre blanket between me and that paper doctors use on their tables.
I was on my side because Kaipo wanted to see my face as I was anally humiliated. She was sitting in an antique chair across the room the whole time.
Dr. Yoshida told me the solution she was forcing into my lower bowels was mostly warm milk, with some chemicals to keep me safe.
Kaipo didn’t want danger, she wanted misery.
After Dr. Yoshida filled me, she removed the enema nozzle from my asshole and helped me off the table.
I was then required to walk over and kneel in front of Kaipo. I would kneel there, I was told, until Kaipo was gracious enough to give me permission to void.
The first time, she nodded her head just a couple of minutes after I got on my knees. Breathing a sigh of relief, I scurried over to a corner of the room where a toilet was.
And voided.
Then I was back on the table.
Filled again.
Kneeling again.
Voiding again.
Over and over.
For what was likely between eight and 10 hours.
Kaipo kept changing the amount of time I had to kneel and hold the enema solution inside me. That unknown was maddening.
My body was in rebellion.
Twice, I failed to hold it before Kaipo’s nod of permission. The first time, I jumped up quickly enough to get to the toilet. The second time, I didn’t make it half way.
I was punished, of course.
Kaipo sent a text each time. And each time, a man arrived.
Hawaiian, young, muscular and with a cock nearly as big as Master’s monster.
He held my head in his hands and throat fucked me.
I gagged. I choked. I fought. I constantly struggled to breathe.
I vomited. Repeatedly.
He and Kaipo laughed the whole time.
When he was done, he left and Kaipo sent another text. A maid came in and cleaned up my spittle, and the void I’d left during that second failure.
Then …
Back on the table.
That second day was the one I hated most.
But a better day was just a good sleep away.
Kaleikaumaka.
CHAPTER 5
On That Third Day …
— 2:46 p.m. —
Kaleikaumaka rolls over.
She’s face down on the bed now.
She lifts her ass.
Kneeling behind the girl, I bend forward. Take her ass in my hands and spread her cheeks.
Kaleikaumaka looks back over her shoulder.
“Beg for it.”
I slump back on my heels.
“May I please lick your asshole, Miss Kaleikaumaka? Please, Miss Kaleikaumaka. Please let me service your beautiful, perfect ass, Miss Kaleikaumaka. Please. I beg you, Miss Kaleikaumaka. Please.”
“I want a lot of full tongue.”
“Yes, Miss Kaleikaumaka.”
— 8:18 a.m. —
The first time I saw her I was actually wearing clothes.
On my second night, I slept in a normal bedroom, not that anal prison cell I had been subjected to the night before.
And that morning … another surprise. I was given a dress to wear.
And told to go see Kaipo on the east veranda.
When I got there, she was with a young woman.
Lovely looking, but nerdy.
Lord was I ever wrong.
“This is my granddaughter Kaleikaumaka,” Kaipo said. “She’ll be staying here overseeing the house while I’m gone.”
I was then surprised to learn Kaipo was about to fly to one of the other islands for a two-day meeting with extended family members of her generation.
My poor suffering asshole rejoiced to hear that news.
“Obey my treasure as you would me,” Kaipo said, and then took the girl aside, spoke to her and left.
Kaleikaumaka walked back over to me. That sweet smile was now gone.
Matter of factly, she said, “Every woman I’ve taken to bed has regretted it. And loved it. And never ever forgotten it.”
“Every woman,” I volleyed back with a laugh. “That’s impressive. How about the girls?”
“I don’t fuck girls. Only women.”
Then suddenly, she punched me in the stomach.
A sucker punch, boxers call that.
It was a powerful blow. That and the shock of it sent me to my knees.
She was snarling now.
“Take me to the room tūtū had you stashed in. You can stay down there. Crawl.”
So, on hands and knees, I led her to the bedroom of the night before.
When I heard her close the door, I straightened up to just my knees. A painful blow crashed into my lower back.
A kidney punch, boxers call that.
I gasped and had to fight for breath.
Then a fist crunched the back of my neck.
A rabbit punch, boxers call that.
I slumped face down onto the floor. She kicked me. Then again.
Said …
“Strip down to that collar and whore heels, bitch. I got a different use for my fist.”
Fisting, unfortunate women call that.
— 4:16 pm —
Later, as I’ve described, she decided to face fuck me.
While grinding, she called her friend Savannah about the change of plans.
“And bring your big dick,” she said. “This milf bitch has a cave for a cunt.”
Let me make this clear.
Savannah was an evil piece of shit. Mean, cruel, hateful.
As much as Kaleikaumaka beat me, the most she did to my face was slap it.
Savannah gave me two black eyes.
But …
Some girls and women just know how to work a strap-on.
Savannah was a girl cock artist.
Unlike most women wielding a strap-on, she knew you fucked a month differently than a pussy.
Or asshole.
She did all three of mine,
Wonderfully.
That day with those to hell-spawned creatures was the highlight of my literal butt-hurt trip to the Paradise Isles.
HOW WE SERVE MASTER 