Transsexual Journey 03

ONLY TWO DAYS LEFT BEFORE ARRIVING IN BARCELONA

Jay had never in his life that he would have hooked up with a ladyboy. He also never expected that he would enjoy the brief affair as much as he did. He had to admit that Caridad was as beautiful and shapely as any woman he had dated. The fact that only he knew that she was a ladyboy was also a turn-on for him. It was their secret that the other passengers and ship's crew thought she was a Spanish beauty. One couple had asked him if he and his girlfriend wanted to swing with them. Caridad and Jay got a charge out of that. Imagine the surprise for that couple when they found out that she had a dick.

Since they met they had sex as often as they wanted. A typical day would start off with morning sex, then have sex again before dinner. They would dine and take in whatever entertainment was provided and then she would spend the night with Jay. During the day, they took part in activities and did not miss any meals. Somedays they just relaxed in deck chairs or hung out by the pool.

That Thursday had been a typical day so far. They had morning sex when they awoke before showering, dressing and eating breakfast. They relaxed in deck chairs before lunch and afterward sat by the pool deck. Jay was amused by the men checking Caridad out in her tasteful two-piece swimwear. They returned to his room for more sex and then she went to her room to get ready for dinner. Afterward they listened and danced to the band and an excellent tenor sing popular European songs. Following the entertainment, Caridad stopped by her room to change clothes and then joined Jay in his stateroom.

They were naked in bed and she played with his impressive cock stroking it back to hardness. Between sucking it and stroking it Caridad soon had Jay ready to go again.

"Fuck me like a woman this night," Caridad asked as she lay back and spread her legs.

Jay moved between the shapely legs and looked down at Caridad's 3" erect cock. It was much shorter and slimmer than his but it was still a cock. However, he had gotten used to it and didn't mind jerking her off. He eased his bigger and thicker dick into her ass and began to fuck her slowly. He loved her cute firm tits and he fondled them and pinched the nipples lightly. Jay watched his cock slide in and out of her ass as the stiff little pecker cock flop around on her abdomen. He really preferred fucking her doggy style and watching her hot ass jiggle but since Caridad had asked to fuck in this position he obliged.

"Jay, play with my clit please," she cooed.

Caridad liked to call her cock a clit. He took a hold of the erect little cock and began to stroke it as he fucked her. He had come around so that he did not mind giving Caridad a hand job in fact he even liked making her cum. This was the first time they had fucked missionary style when he jerked her off.

"Oh Jay, I am so close," she moaned.

Jay picked up the pace fucking and jerking on her cock. It was a quick one as Caridad cried out and cum shot out of her dick. He worked the cock as he watched cum shoot onto her lovely body. The first few streams landed on her tits, and then the next streams hit her abs before it oozed cum onto her pubes. Jay continued to fuck her and she pulled him down to her. She wrapped her legs around his torso and he felt her damp semen against his body.

Caridad remained hard and Jay felt the stiff pecker against his abdomen as she drilled her hot ass. He was getting close and remarkably so was Caridad as she was incredibly turned on that night. He soon felt his balls tighten and kept his weight off of her and he prepared to cum in her sweet ass.

"Cum on me this time," she whispered.

He pulled his cock from her ass and held it toward her lithe slender body. Two forceful ropes shot out of his dick and landed on the cute tits. Caridad squealed in pleasure as the warm liquid landed on him. Jay jerked his cock and more cum shot out onto her body coating the abs and dripping on the pubes. She was also jerking her cock and cumming again. Jay was actually turned on by cumming on her and watching his seed mix with hers. He rocked back on his haunches and stared at the lovely cum covered body.

"Oh, look at it all," Caridad cooed as she rubbed the comingled ejaculations into her tits and abs.

Jay watched as she rubbed the semen into her skin and then she said, "Let's take a bath together.

The two of them sat in the small tub filled with hot water and let their bodies soak. Caridad leaned back into him and he wrapped his arms around her and fondled her firm tits. They remained in the tub relaxing until the water cooled and they got out and dried off. They dried off and got back in bed and slept in the nude. Cuddling in the spoon position they fell asleep with Jay's semi-hard cock pressed against her curvy bottom.

THE FINAL DAY AT SEA

Caridad had awakened before Jay and she decided to make coffee on the room. She slipped on a pair of panties and donned the short nightie top that she had packed but not worn. As she was making the coffee, Jay woke up and watched her move around. He stared at her ass and eventually decided he couldn't wait any longer to take it. He slipped out of bed still naked and moved behind Caridad who was standing by the counter. Reaching around the lithe body, he grabbed the cute firm braless tits under the nightie top. She groaned and her eyes glazed with intense lust.

Jay ran his hands down and inside the panties cupping the lovely buttocks. He peeled the nightie top off, lowered the panties and she pressed her ass back against his rock-hard cock. Jay ran his cock up and down in the crack of the sweet ass driving them both wild.

He rubbed the head of his cock against the dry puckered hole but then looked for the lubricant. His head turned towards the tube of gel on the night stand and he broke away to retrieve it. He squeezed out a generous amount and proceeded to slick himself, hugging Caridad the whole time. He didn't remember wanting anyone more than he wanted her at that moment. When his slick finger penetrated her hungry hole, she was almost desperate with need. It felt so good she groaned, grunted and whimpered for the anticipated butt fuck.

"Oh God, that feels so good," she moaned helplessly when two thick fingers entered her.

She started to buck against the delicious assault, fucking herself on those fingers until she thought she'd go crazy when the thick fingers brushed over her prostate. Her breath came in ragged gasps, her body sweating as she shamelessly begged Jay with her body to fuck her.

"Please give me your cock. I can't wait any longer."

Jay gave it to her hard. He'd fucked her so good Caridad's entire body quivered with mind-blowing pleasure. She had never felt more dominated than she did that morning. Caridad didn't remember ever enjoying a fuck as much as that one and felt a jolt of pleasure so intense she clamped down on the plunging cock with her sphincter. Jay threw his head back and groaned with pleasure.

Their climax, when it finally hit, was so powerful they'd both cried out with rapturous gratification. It had been so good Caridad had been utterly euphoric afterwards. Caridad returned slowly to a sense of where she was and who she was with, never having experienced anything so wonderful. Her body was still quivering from pleasurable aftershocks. Her eyes actually widened when she saw the load of cum on the floor in front of her. Caridad didn't remember ever spurting that much and neither of them had even touched her cock once. She had never orgasmed that way before just from having a cock inside her.

She gasped when she finally caught her breath. "That was amazing."

"Do you want to go to back to bed now?"

"You may have to carry me."

It was the last day that Jay would be with Caridad before the shipped docked in Barcelona and he wanted to make it special. They stayed in bed for hours and had incredible anal sex. It was well after breakfast time when Jay finally admitted that it would be impossible for him to cum again. They both had had multiple intense orgasms and they were spent for the morning.

Eventually they got out of bed, showered and headed for the dining room to enjoy a leisurely lunch. Being their last day together, after lunch they returned to Jay's stateroom. Caridad was still drained and sated from the morning so Jay offered her a massage to help rejuvenate her. She willing accepted and they both got naked. He had her lay on her back first as he wanted to save her ass for last. Jay took the body lotion and poured and ample amount on her lovely breasts.

Caridad had expected him to fuck her ass but she allowed herself to be turned over and she closed her eyes as Jay's hands rubbed oil all over the front of her body. He began with her shoulders and neck and then descended to her breasts. Her nipples were hard as rocks when he massaged her breasts and rolled the extended nubs in his fingers. Next his hands moved lower to Caridad's thighs skipping her hips and pubes. He massaged each leg separately lifting it to his shoulder and rubbing it all the way to her crotch. His hands would occasionally graze her cock and Caridad would flinch in response. Once again, she was in a state of desire and she felt the need to orgasm.

"Touch me!" she whispered in an obvious state of desire.

"Do you need to cum Caridad?"

Caridad just closed her eyes and nodded yes. He gently rubbed Caridad's abdomen with the massage oil and sought out her erect cock. He pushed two oily fingers into her ass and rubbed her clit, as she liked to call it. Caridad covered her mouth with her arm as an orgasm rocked her pretty body. She kept her eyes shut as her body jerked and her cock ejaculated coating Jay's hand. He removed his fingers from her ass and he was anxious to fuck her.

Jay rolled her over so that she was face down on the bed again and then he returned his attention to her ass. He kneaded her gorgeous ass cheeks and as he massaged her ass, he put an ample amount of oil on her anus. He began to probe her anus first with one and then two fingers. Before long his fingers were moving easily in and out of Caridad's thoroughly lubed asshole. He lifted her up by her hips until her ass was in the air as she rested her head on the bed. He removed his fingers and climbed up on the bed with Caridad. He positioned the head of his cock at the entrance to her ass.

As Jay eased his cock into her ass the head cleared her sphincter and Caridad uttered an audible gasp. The pressure was familiar as the thick cock worked its way deeper and deeper into her receptive ass. Jay continued to ease his cock in and out of her ass feeding her an additional ¼ to ½ inch at a time, each time waiting until she relaxed before going deeper. It seemed to take longer this time before his entire cock was lodged deep in her ass. Jay was so hot that he shot his load immediately when his cock was fully embedded in her ass. Caridad felt the warm cum shoot into her rectum and she loved it. She liked the soothing feel it gave her ravaged rectum. Jay started to fuck her with long deliberate strokes as he admired her beautiful ass accepting his huge cock. Jay stroked her marvelous ass cheeks and told her how good she looked in this position with his dick skewering her luscious ass.

The initial pain had subsided completely and now Caridad felt more of a bloating and cramping sensation. The cramping then stopped and now Caridad only felt somewhat constipated with the cock in her ass. Jay felt his second orgasm start down in his balls and rush up through his cock flooding her rectum again. He came more than he expected and cum soon filled her to overflowing and backed up coating his cock and running down the inside of her thighs. However, he was not done with her and he continued fucking her tight ass even though he was sure that he could not cum again. Her rectum held his cock tightly and Jay felt as if he could stay hard forever in Caridad's beautiful ass.

He watched his cock saw in and out of her beautiful ass. Caridad had her head turned to the side of the bed and she was gripping the bed sheets with both hands as he fondled her shapely buttocks and plowed into her. He kept slowly fucking her ass until his cock started to soften. Her ass involuntarily was milking his cock draining it of all his seed. When his cock finally slipped from her incredible ass with an audible pop, his cum shot out and ran down the back of her legs and over her pussy. It looked like she was cumming out of her anus. She collapsed face down on the bed and Jay stroked her buns lovingly as she lay quietly. He was drained and he knew he had nothing left until later that night.

THEIR LAST NIGHT TOGETHER

As was the norm, they dined and attended the evening entertainment. After a night cap, they went back to Jay's stateroom. Even though they had incredible sex earlier that day they were anxious to be together again. Jay could not get enough of Caridad's ass and she could not get enough of his cock. Once in the room they stripped quickly and got in bed.

Jay retrieved the lubricant from his night table where it was always handy. He knelt behind Caridad and applied the lube generously to her snug aperture. She cooed with pleasure as first one and then two fingers entered her anus. He felt the tightness and he knew that he would need plenty of lube as he always. As anxious as he was to get his cock in that hot looking ass, he enjoyed the anal foreplay as did Caridad. He took his time fingering and playing with her sweet ass and as he did, he decided to rim her lovely hole.

Finally, Jay could wait no longer and he eased his cock into the beauty's ass. The fit was snug even though he had stretched it somewhat during the week. He fed his cock to her a little at a time and he savored the slow penetration. Little by little his cock entered her and eventually filled her rectum taking her breath away. Jay stopped moving and allowed Caridad to adjust yet again to the longest and thickest cock that had ever been in her ass. He began to move slowly and he watched his cock as it slid in and out of her shapely ass. longer. Caridad's ass was so beautiful and the sight of his cock going in and out was so erotic.

Jay felt his release build in his scrotum and travel through his shaft. He stopped moving and leaned over Caridad hugging her as he filled her rectum with a small load as it was his fourth of the day. Jay felt her hand reach between their legs and cup his taut ball sac as he ejaculated. They both remained still and he remained hard in her sheath. As he recovered from his intense ejaculation, he resumed fucking her ever so slowly. He wanted to stay in her ass for the rest of the night.

Caridad requested to lie on their sides if he was going to keep fucking her. With incredible flexibility moved to their sides with his cock still in her ass. They were on their left sides in a spoon position when he resumed fucking her. His right hand instinctively cupped a firm breast. He loved the firmness of her tit and he felt the nipple harden and press into his palm. Jay rocked back and forth slowly and he savored every minute he was in the super fine ass.

They had not spoken a word since they got in the bed and there was really nothing to be said. They were enjoying each other and Caridad was being the perfect lover. He lost track of the time but he was sure that they had been fucking for hours before it felt as if he came final time that night. He hugged Caridad to him as he stayed in her ass and continued to fondle the firm little tit as she played with her little cock. He felt her stiffen as she orgasmed and her sphincter tightened around his softening cock.

They remained in the spoon position and his cock eventually went soft and slipped from her ass. They remained in the same position and dozed off together. Jay loved the feel of Caridad's soft smooth flesh against his own. Sometime during the early morning hours Jay got another erection and subconsciously pushed it back in Caridad's receptive ass. He went back to sleep with his cock in her ass. When he woke up the next morning they were still in the spoon position and his morning erection was nestled between her marvelous buttocks.

THE FINAL MORNING FLING

When Jay woke up in the morning with an erection he was pleased to see Caridad in bed with him. It would be their very last time together. As he lay there and looked at her lovely body he thought back through the week and recalled the great sex they had had together. Caridad was naked lying face down and her lovely ass was once again there for the taking.

As Jay looked at the lovely ass inviting the intrusion of his cock he reflected on his newly adopted bi-sexual life style. If it were not for his passion for anal sex, he knew that it would be unlikely that he would have ever agreed to have sex with a ladyboy. Even with women he was very selective about with whom he had anal sex. He was still enamored the pretty and shapely ladyboy Caridad. His cock stirred as the thoughts ran through his mind and he decided it was time for Caridad's wake up call.

He applied a liberal amount of gel to his throbbing cock and rolled the Spanish beauty onto her stomach. Pushing the shapely legs apart, he eased his slick dick into the receptive rectum. He moved slowly as he wanted to enjoy every second he was in the curvy bottom. He looked down at his lover and watched as his big dick slid in and out of the marvelous ass. It was a sight that he had come to love. His impressive cock would disappear into her shapely ass and then re-appear again. He would pull it out until just the head remained in the gripping ass and then he would drive it back in causing her curvy buttocks to jiggle. Caridad had her head down on the mattress turned to one side so she could watch Jay fuck her. Her back was slightly arched further emphasizing the shape of her incredible ass. Caridad's hand stroked her own cock as Jay drilled her with conviction.

She whispered for him to cum on her that morning. Jay felt his ejaculation building in his loins so he pulled his cock from her ass and stroked it off until he shot his load. He aimed his cock so that the first forceful stream hit her anus. The next two jets, almost as forceful as the first, landed in the crack of her ass and trickled down over her anus between her legs onto her ball sac. Three more ropes of semen landed on the curvy buttocks before he pushed his cock back into her ass. As he re-entered her, he pushed his semen into her rectum and then resumed fucking her. This time Caridad pushed back and moved to her knees.

This had become their favorite position and favorite ways to cum. She loved feeling the warm sperm land on her ass and then feel it pushed back into her anus with the big cock. Jay also loved watching his cock spurt and shoot jets of semen onto her buttocks and anus. He resumed fucking her and she continued jerking off. They were both capable of multiple ejaculations a day which had been the case all week. Jay fucked Caridad until he ejaculated a second time only this time, he remained in her ass and filled her rectum with a substantial load.

Caridad wanted to cum so she rolled over on her back and Jay fucked her missionary style. She shot twice and Jay liked watching her cum all over her chest and abs. When Caridad ejaculated, her sphincter contracted around the thick cock pushing Jay toward another release. He stayed in her ass and shot a little more semen into her rectum. The final position was on their sides in a spoon position as Jay fucked Caridad slowly. In this position, he would reach around her body and jerk her cock until she ejaculated again. Jay had become accustomed to jerking off Caridad while he fucked him. They had had sex that morning for nearly three hours and they rested in bed for another half hour before they got up.