PRELUDE

Jay woke up to the gentle movement of the cruise ship through the Atlantic. His bladder needed relief so he eased out of bed and quietly used the bathroom in the stateroom. Once he had taken his morning piss, he washed his hands and cock before crawling back in bed. As he approached the bed he admired the Spanish beauty lying there with her back to him. His cock started to harden again as he admired the lovely figure with the absolute marvelous ass.

Locating the lubricating gel that he had used the night before, he applied it liberally to his stiffening cock. By the time he got back in bed his 7" cock was rock hard and he eased it into Caridad's ass. She had been half asleep but the penetration awakened her and she moaned softly. Jay slid his left arm under her delicate body and reached around and cupped one of her 34B breasts. With his right hand, he reached down and took a hold of her small slender cock which was already hard.

Just as he had the previous times he moved slowly in and out of her clenching ass. Her long light brown hair with blonde accents glittered in the morning light peeking in through the port hole. Jay fondled her breast, tweaked the hard nipple and stroked the little dick. It was a very different feeling than holding his own larger cock but it was also the first cock other than his own he jerked off.

Caridad tilted her head back toward him and reached up with her right hand to pull his face close to hers. They kissed as if they were man and woman. Other that Caridad had a cock, one would think that she was a beautiful young Spanish woman. Jay at first had resisted her kisses but then he had come around. Her lips were soft like a woman's and besides who else would ever know that he kissed a ladyboy.

Jay's ejaculation snuck up on him and just as he had the nine other times, he came in Caridad's ass. The force of his release into her rectum set her off and she came coating Jay's hand. They remained still for a few minutes savoring the delight of their orgasms. Caridad then lifted Jay's hand to her mouth and licked it clean. As they lay in bed, he thought about the first night they were together.

He had spotted her in the club that evening and introduced himself. They drank, danced and even kissed on the dance floor. She had even taken him into the W.C. and gave him a mind-blowing blow job. She had been reluctant to come back to his stateroom but he had been insistent. It was then he learned that she was a ladyboy. He was stunned, embarrassed but still in awe of her body and beauty. When she offered him her ass, he could not refuse.

Jay had never fucked a gay or a transsexual in his life but Caridad's ass was just too desirable. Once she had her back to him and teasing him with that magnificent bottom, he was hooked and he fucked his first ladyboy. That was three nights ago and they had been together every night since.

THREE DAYS EARLIER

Barcelona was one of Jay's favorite cities in Europe so when he had the opportunity to travel there on a cruise ship, he jumped at it. His good friend Nevin and his wife had planned to go but she got ill just before the trip. There would be no refund so Nevin offered Jay their stateroom for 25% of what he paid. Jay jumped at the chance and willingly paid Nevin.

Jay had been on cruises before but short ones and this time he was looking forward to crossing the Atlantic and visiting Barcelona for a few days. Of course, he was hoping to meet some sweet young thing and get laid on the way to Spain. Jay was a good looking fit guy of 28 years. He was 6'1" and weighed a fit 185 pounds. He was a skier, tennis player and all around outdoor type. His hair was light brown and he had hazel eyes that the girls loved. Jay did not have a steady girlfriend as he liked his independence and variety of ladies.

On the first night of the cruise after the orientation and dinner, he went to the lounge where a band was playing. Standing at the bar he spotted a drop dead gorgeous girl at the other end. She looked to be Spanish and he was right. He stared at her for a few minutes admiring her. She looked to be a slender 5'6" with a very curvy figure and absolute killer ass. Her hair was light brown with blonde accents. She was wearing a mini dress with the skirt cut well above the knee showing off her lovely legs. She was wearing dangling earrings and several necklaces. She was absolutely stunning.

A slow song came on and Jay walked over to her and asked her to dance. She smiled at him and accepted. His eyes dropped to her legs as she slid off the stool. Following her out to the dance floor he admired her ass and felt his loins stirring. They danced together and chatted getting acquainted. Jay learned that she lived in Barcelona and was traveling home after visiting relatives in the states. She didn't like to fly.

As they danced to more songs they became enamored with each other and danced closer and closer. Jay got a boner but Caridad seemed to like it pressing against her thigh and she moved purposely against it. Jay was so drawn to her that when she lifted her face to be kissed his lips met hers. They were soft and delicate just as he liked them. They danced close and kissed often before finally leaving the dance floor to return to the bar.

After another drink, she took him by the hand and led into one of the water closets. Inside she dropped to her knees and fished his stiff dick out through the fly opening in his pants. She gave him an incredible blow job and he was so turned on that he came quickly. He was thoughtful to warn her but she went right on sucking his cock and swallowed his load. They straightened up quickly and then stepped out of the W.C. Jay asked her to his stateroom but she was reluctant at first but then finally agreed.

They walked through the passageway toward Jay's stateroom with their arms around their waists. When the passageway was clear of other people, Jay let his hand drop to her ass and fondled the firm buttocks. Once in the stateroom they sat on the sofa and he leaned in to kiss her. Caridad met his kiss and shoved her tongue in his mouth. Jay felt his cock surge as he kissed her deeply. His hands went to her covered breasts. The feel of her lovely round breasts covered in the soft material of her dress felt wonderful and he gave them a loving squeeze to show his appreciation of her beauty.

Caridad threw her head back, emitting a throaty moan, and gave him a perfect opportunity to bare her breasts. He unzipped the back of her dress as his tongue and lips caressed her neck. He tasted her warm soft skin losing himself in the wonderful scent. He lowered the top of her dress to her lap and unfastened the bra. He slid the bra down her arms to expose the lovely orbs to his now eager mouth. He could feel Caridad's enjoyment as her hands held his head firmly to her breasts. As he started his kiss trail down her chest in search of his next objective, she stopped him.

"Let's get undressed. I want to undress you," she whispered.

Without waiting for his response, she removed his suit jacket, shirt and tie. Next she dropped to her knees in front of him, undid his belt and slid his pants off letting them drop to the floor. She then pulled down his briefs and let them catch his rock-hard cock. She slid them to the floor and watched as his erection caught in the waistband and sprung out. Caridad kissed her way up Jay's legs and took his stiff penis into her mouth just as she had earlier in the W.C. Jay had had plenty of blowjobs in the past but he had never felt what Caridad made him feel.

There was something about her movements as she employed just the right amount of teasing and nibbling. He knew he was in for another ejaculation of monumental proportions. Jay felt her hands grab his ass cheeks behind him and he was impressed with her strength for such a petite girl. She spread the cheeks of his ass and he could feel her fingers moving toward his anal portal. She lubricated her finger with the mixture of her saliva and his pre-cum and slipped the moistened finger into his tight ass.

The sensation of this was almost too much for him to bear. Caridad seemed to sense his condition and she held still for just a moment letting him adjust. Her finger moved with urgency now as she finger fucked him in the ass to the same tempo that her mouth sucked his cock. She found his prostate and she sucked him all the way into her mouth and caused a volcanic eruption. Jay held onto her shoulders as his toes curled and he flooded her mouth with his second massive load of the evening. He pushed into her and balanced himself by holding onto to her shoulders as the ejaculation drained his energy.

Caridad hungrily and insatiably drank down all his cum again but this time she stood up and kissed him to let him taste himself in her mouth. Jay was not repulsed by the taste of his own cum as women had done this before. He then guided her onto the bed. It was his turn to undress her. Caridad's bra was long gone but she still had on her dress.

He pulled the dress off her lovely body leaving her in just her thigh high hose and panties. He kissed her naked thighs above the hose as he worked his way back up. He engulfed himself in her musky scent as his face hovered over her black silk panties. Jay was thrilled as he anticipated eating Caridad's sweet pussy and then fucking her. Secretly he still hoped that he would get to fuck her in the ass. As his hands removed her panties and slid them down they seemed to snag on something. Before Jay could figure out why the panties were caught, her cock moved free and sprung out. Jay was now staring at a small slender erection. It was small but it was definitely a cock.

He sat up and drew back in disbelief. How could anyone so beautiful be a guy? Transsexual was the description that came to mind. He had been hoodwinked and but good. The entire evening, she had behaved like a sensuous woman and he went along with it. They had danced, kissed and had oral sex. He sat in shock staring at the lovely woman with a dick.

"How could you?" he managed to say

"I'm sorry, I should have told you. I wasn't going to come to your room but you were so insistent and I love your cock."

"I kissed you."

"Yes and was that so bad. You really didn't know that I was a Spanish ladyboy. My lips are as soft as any woman's. I know that you like my ass and I bet you were hoping to fuck me there."

"Yes, I have to admit that I was but that was before I knew that you are a ladyboy. Is that what you call yourself?"

"Yes, I like that name the best. Now I want you to fuck me in the ass. Would you like to fuck me now?"

Lost for words Jay watched as Caridad rose from the bed and walked seductively to her purse. She retrieved a tube of gel and then returned to the bed. She poured some in her hand and then she stroked his raging hard-on getting it very slick.

"Now get my ass ready for your cock."

Jay needed no further instruction when it came to preparing an ass for a fucking. As Caridad crawled onto the bed on all fours, he was enticed with the incredible ass. He poured some of the fragrant gel onto his hands and then placed a copious amount on her beautifully rounded bottom. He knew that the ass was there for his taking if he could get passed her being a ladyboy. Jay loved watching the slow circles of Caridad's derriere as she teased him unmercifully. He let his slippery fingers travel lightly all around the lovely buttocks. He heard a sharp gasp escape her mouth when his fingers first reached the crack between her cheeks. He started at the top of her ass and moved ever so slowly down until one fingertip reached the puckered opening. Caridad sighed deeply with pleasure in anticipation.

"I am very clean. I douched my ass thoroughly earlier this evening," she whispered excitedly.

Jay did not penetrate the now anxious hole but instead he separated the lovely butt cheeks, exposing her anal opening. As if in a trance, he moved his head down and dipped his tongue between the shapely cheeks. Caridad's movements became frantic with desire and he loved it. He was no stranger to rimming a sweet ass but this was a first with a ladyboy. His tongue probed at the well-lubricated anal opening and then he surprised himself when he pulled the cheeks apart and jammed his tongue in as deeply as he could. She bucked back at him trying to get more of his tongue inside the receptive hole. He probed in and out with his tongue as he prepared the lovely ass to be fucked. The sensation was overwhelming for Caridad but there was a desire for more in there than his tongue.

"Please, please, now! Jay, I need your hard cock in my ass."

Jay pulled his tongue away from her ass and got up on his knees behind the beauty. He moved his cock close to her anus and positioned the head at her rubbery opening. Overcome with desire at this point, he held nothing back as he eased his cock as far into her ass as he could.

"Yes, that's it, oh yes," she encouraged.

His hands held the sides of her shapely hips as he fulfilled his desire to fuck the beautiful shapely ass. By then he forgot about her little cock as it was not visible and in his mind, he was fucking a beautiful young Spanish woman in the ass. Caridad met and matched each thrust from Jay. He pounded her ass and his pelvis slapped into the ass cheeks causing them to jiggle each time. He was going wild with passion and he knew that he would not hold out too much longer. As much as he wanted to prolong fucking her incredible ass, he could feel that familiar sensation building again.

"Jay cum in me, I want to feel you cum in my ass."

He made one final push and held himself tight against her ass cheeks as spurt after spurt shot in to the rectum. He groaned aloud as he filled her ass with hot cum. Caridad groaned too feeling the hot seed shoot in and fill the anal passage. They stayed coupled tightly together as she used her talented sphincter muscle to milk every drop from his shaft. He loved the sensation of the clenching gripping movement as he filled her chamber.

"Oh that was wonderful! I am so glad that you could cum so much again. I love it when my ass is full of cum."

Jay leaned over her keeping his cock deep in her ass and grabbed the firm breasts. He played with the rock-hard nipples as he massaged them. He too was thrilled with his capacity to cum so much a third time. Her ass was like an aphrodisiac. They stayed like that for several minutes and then his cock softened and slipped from Caridad's ass. They both sighed and then collapsed forward on the bed. They cuddled together as lovers should after incredible sex.

It seemed like they dozed but when Jay woke up, Caridad was gone. He rolled over on his back and stared at the ceiling. He was still in disbelief that he had behaved in suck a way with transsexual, ladyboy. Caridad was as beautiful as any woman he had ever fucked but she was still not a woman. He tried to convince himself that it was only once and it wouldn't happen again. There were six more days and nights before they reached Barcelona. Would he resist Caridad's charm, talented mouth and incredible ass for the remainder of the journey? He had to admit that he wasn't sure he could or if he wanted to.