One Friday Night Ch. 02

"Don't take all day honey. Alisha and Keron want to see them."

As soon as they had boarded the charter cat in Prickly Bay, they'd dropped the mooring and set sail. Captain Keron was at the helm. His mate, Alisha, was mixing a big pitcher of rum punch in the galley. James and Helen went to their separate cabins to change out of the clothes they worn on the flight down to Grenada.

Helen changed to a bright pink bikini, who's top would soon be discarded. Lipstick (pink) and sunblock were the makeup of choice for both of them.

James changed into a stubby tight cock cage, a tropical print micro mini skirt, and a white string bikini top that displayed his boobs that were really responding to the hormones Helen had been administrating. He put on his new long blond wig, and for the rest of the week, he'll be Jill the Bimbo.

Alisha's sunshine yellow sundress looked inviting with her big brown nipples poking excitedly at the thin material. She gave Jill as slow appraisal and licked her full lips. She spread her arms. "Come here you shy white tramp and give yo island mamma a big wet kiss!" Jill's extreme cage suddenly was deliciously tight.

"Here, get a glass of rum punch and take a beer up to Keron. Helen and I've got some catching up to do while I fix some snacks. She smacked Jill's butt.

"Glad you booked with us again, Jill."

She blushed. They sipped their drinks as they rounded Point Saline. Once the new course was set and the sails trimmed Keron set the autopilot. He slid an arm over Jill's shoulder and pulled her to a kiss as his other hand began molesting her boobs.

"They've grown since last summer at your place. A good handful."

"Thank you." Jill blushed.

Keron stood for a moment and slipped out of his shorts. Jill smiled and reached for his beautiful black pole. So big and velvety hard. She lowered her lips to it's knob and gently kissed. She adoringly licked up and down. Helen's collection of dildos and strapons just were not the same as the real thing. She wrapped her lips around the black wonder and swallowed. "Mm, mm." So big. So yummy. She fondled his big hairy balls. "Mm." The sensation, a big mouthful of warm black cock. "Mm." She felt the tug as the strap of her top coming undone. "Mm." She wondered if the tourists on Grand Anse Beach could see what she was doing. The idea excited her. "Mm, mm." His big hand stroked her pale white back. "Mm."

Then he exploded. Cum in her mouth. Cum down her throat. Cum dribbling down her chin. Hot thick yummy cum. Lots of cum.

Keron's laugh was warm and deep. "You've got some real talent there, baby. I can see we're going to have a great week together."

The St.Georges anchorage is a big shallow bay. They were anchored a short distance from the nearest yacht. As soon as the anchor was set they were all in the water. Without her cock cage (didn't want salt water to seize the lock) Jill's bikini bottom had an inviting sissy bulge.

More drinks and laughter. Supper, washed down with wine, was a salad featuring mango and star fruit, and lambi (conch) rotis. Soon they carried the bean bag chairs to the front trampoline.

As the sun set anchor lights began winking on around them. The new moon was just a sliver. Soon the milky way was thrown across the sky. Talk quietened. Hands slid across. Four naked bodies were soon on the mesh kissing and caressing. The dirty snow and slush of the city a billion miles away. Jill wasn't a CEO, she was a sissy bimbo.

"I think it's bedtime, we've had a long day. Had to be at Pearson at five. Like Uncle Willy said, ' flying's fun if you've got the time', eh."

Jill reached for Alisha's hand. She kissed Jill's cheek. "No baby. Helen and I are sleeping together. You're Captain Keron's bitch this week." Joy and fear ran through Jill's mind for a nano second.

Keron's hand slid down Jill's arm and gently took her hand. He led her down one side of the cabin trunk as Helen and Alisha went along the other. In the cockpit he said quietly, "We don't have to rush." He wrapped Jill in his arms for a deep sweet kiss. They sat on the cockpit bench seat and kissed between admiring the black sea and the star filled sky.

"This is a first for me too, I mean, sleeping with a ah,"

"Sissy boy?"

"Um, yes."

"Mm, let's go inside."

Keron pointed to the woven frond basket on the bedside table. "Pick your favorite color."

The basket had a selection of condoms. Jill picked one. "Let me put it on you?"

"Sure, baby."

Jill's hands had a slight tremble as she rolled it down his magnificent black pole. Suddenly it was happening. The excitement had been building since they booked the charter. Helen had been giving Jill regular bonings to prepare her girly boy cunt hole. Now it was time for the real thing.

"How do you want to do this? I mean, um?"

Jill bent over the edge of the bed and spread her legs. "Start slow dear."

Keron dribbled some lube down Jill's crack and worked it in with his finger.

"Mm, nice." Then the spreading as he slowly pushed his helmet through her sphincter. "Ah!" A little pain as it spread her sissy cunt hole. "Huuh!" He was in. Slowly he filled her up. Really filled her. Really deep.

"Good girl. Nice and tight. Mm." He began long slow strokes.

Jill let out a little gasp with each deep slide into her ass.. "Uh. Uh. Uh." The sensation of it all. Those big hands firmly holding her shoulders, his thighs hitting her butt and the back of her legs with each plunge, Her hard clitty cock sliding over the sheets with each ram.

"Faster. Please. Please. Umph!" Keron responded with hard fast rams. Ram. Ram. Ram. She felt her clitty staring to let go. She squired onto the sheets as Keron rammed and rammed. Then he came with a satisfied grunt.

His arms held her. A week of sunny days and star filled night. A week of beach walks, beach bars, and local restaurants. But mostly a week of Keron's cock in her hand, mouth or her cunt hole any time she wanted it. Jill pulled his hand to her lips and kissed it.