Transsexual Journey 02

DAY TWO OF THE CRUISE TO BARCELONA

Jay woke up leisurely on Sunday morning and lay in bed for a while thinking about his encounter with Caridad the night before. He was still somewhat shaken by his willingness to have sex with a transsexual but more so, that he had enjoyed it so much. She was so damn pretty and shapely that it had been way too easy. Her body was lovely, hairless and smooth. Eventually he got up and made his way to the bathroom to clean up.

Sunday was a laid-back day with limited activities starting with a buffet brunch. He put on his tropical pants and short sleeve shirt before making his way to the dining area for a late breakfast. The food was plentiful and very fresh. He decided on an omelet and fruit. Helping himself he filled his plate and then located a place to sit. Minutes later he heard a sweet recognizable voice.

"Good morning Jay, did you sleep well?"

He looked up and saw the beautiful Caridad standing near him holding a plate of food. She was tastefully dressed in short tight shorts, sandals and a halter top. It appeared that she had gone without a bra.

"May I join you?" she went on.

"Yes, of course, please sit down. I slept quite well thank you."

"I'm glad. What do you have planned for today?"

"I haven't looked over the activities list yet but I was just thinking about sitting on the deck and relaxing after brunch."

"I was thinking to do the same thing. There is a cabaret singer later this evening in the lounge who may be fun to listen to."

"Caridad, about last night."

"Yes, I enjoyed myself immensely, did you?"

"I have never done anything like that before."

"But you have had oral sex and anal sex with a woman, no?"

"Yes, I have."

"Did you really find it so different? Was I not a good lover?"

"That's what is driving me crazy. You are a very good lover and I liked being with you. I liked having sex with you."

"Well then, that's settled. I'm glad you like being with me. After we eat let's meet in your stateroom before we sit on the deck."

After brunch they went to his room and Caridad reminded him that she had douched her ass again. They both undressed ever so slowly as he stared at the lovely ladyboy and by the time his underwear was peeled down his legs, he was rock hard. Caridad stared at the 7" cock and then lowered her mouth on the shaft and began to slowly suck it. As she sucked his cock, she got anxious to feel it in her ass again. It was the thickest cock that she ever had in her ass and the prospect of it excited her again. Caridad took out a tube of gel and applied it to Jay's cock. He stayed hard the entire time as she stroked the impressive shaft.

"I like playing with your cock. You know that I could do this all day but I do want you to fuck me again."

She got on all fours and handed the lube to him. "Get my ass ready for your big cock."

Jay took the gel and squirted a gob right on Caridad's anus and then pushed it in. He worked first one finger and then a second in the snug hole. Caridad put her head down on the bed and arched her back further emphasizing the shape of her curvy ass. Jay was still amazed how much she resembled a beautiful young woman and it served to turn him on even more. He caressed Caridad's lovely ass as he lubricated the anus. Satisfied that her ass was ready; he knelt behind her and eased his cock into the lovely curvy ass.

Caridad placed her hand on Jay's thigh as if to guide the penetration. "Nice and easy, I really know that I have someone in me when you're there," she gasped.

"You really feel tight today."

Jay took his time slowly feeding his cock into Caridad's ass and then withdrawing it slightly. Each time he would go a little deeper and then stop to allow her to adjust. Caridad felt the pubic hairs tickle her buttocks and she knew that the cock was buried to the hilt. Jay began a slow methodical fucking of the receptive ass and he relished every second he was in the beautiful derriere. He reached around as he leaned over and his hands brushed against the firm tits. He held them and caressed them teasing the nipples as well. At that moment, he truly felt like he was fucking a girl in the ass. He felt that familiar twinge and he pushed his cock all the way into her ass and held it there as he fired a barrage of cum into the rectum.

"Oh I feel it, I feel it!" she exclaimed as round after round was released from the spurting cock.

Jay placed his hands on the smooth curvy ass cheeks and caressed them as he filled the lovely ass with his seed. He stayed hard and continued to fuck her slowly until she begged him to move to their sides. Keeping his cock deep in the shapely ass, he guided them on their sides and then he resumed fucking her. He had his left arm wrapped around the slim waist and he was holding a breast in his left hand. She guided his free hand to her stiff 3" cock and Jay jerked her off as he fucked her.

"Oh that's it, play with me. Make me cum too. Oh, fuck!" Caridad gasped as she felt fingers wrap around her small erect cock, jerking her with sure strokes.

"Let it go," Jay whispered as he rocked his lower body, plunging into her sweet ass faster, deeper and harder, the thrusts growing more frantic. "Cum for me," he said really getting into it and wanting to make her cum.

Raspy whimpers spilled from Caridad as her entire body stiffened with that moment of exquisite tautness that always came before her release. She felt the warm tightening inside her chest, a feeling so overwhelmingly intense it rendered her breathless. Ropes of thick cum exploded from Caridad's cock onto her belly in long hard spurts, some going above her head to land on the pillow. Her mouth opened in a silent scream as her body convulsed violently on the bed. She couldn't remember the last time she ever came so hard.

"Oh my God," Caridad gasped as she tried to take deep breaths. Her cock was still spurting onto her stomach and coating Jay's hand.

Looking down at the ladyboy lost in so much pleasure, Jay was in awe. Caridad was something to behold when she ejaculated. He wished he could hold off his own impending orgasm and keep his cock within the twitching tissue of the anal channel for a while longer. But he didn't stand a chance against those sweet contractions around his cock. He felt his orgasm start in his lower back, travel up and then down his spine, race into his balls, and then explode through his cock.

"Fuck." He roared as he gave in to his own urgent release, filling the rectum with his hot cum. When the last spasm faded, he held Caridad tightly to him.

He then placed both hands on her tits and held them firmly. The two of them then lay in bed perspiring and breathing hard from their sexual encounter. Checking the time, they realized that they had been having sex for over an hour. Caridad suggested a shower before they dressed and headed to the ship's deck.

They would have sex again before dinner and then following the evening entertainment. That night Caridad stayed in Jay's stateroom but she had thought to bring a change of clothes for the morning.

ANOTHER MORNING ENCORE

The following morning, they were naked and in bed together. She initially sucked his cock which helped cool his jets when he shot his first load quickly in Caridad's mouth. She was then ready to fuck as Jay would be able to last longer before he shot his second load. She knelt on the side of the bed and wiggled her bottom at him inviting him to play with her lovely ass.

Jay was rock hard and his meaty 7" dick looked obscenely big lined up with Caridad's tiny pink rosebud. She had never had a cock as large as Jay's but she was confident and trusted him not to hurt her. Grabbing the buttocks in his hands, he pulled the rubbery edges of the sphincter apart with his thumbs. Using the tube of gel that Caridad had handed him, Jay made sure that the anus was well greased for action. He pushed his cockhead against the snug aperture that always resisted him at first. However, he calmly persisted and nudged his thick tip against the taut pucker. He kept pressing into the backdoor until the elastic ring yielded, dilated and allowed his hardness to slip inside. They both gasped aloud as he slowly penetrated the tight slippery orifice, his cockhead disappeared into her butthole as if sucked in by the hungry anus.

"Oh Jay, I can feel you sliding in me! You're so big, oh my God!" she panted ass he felt her snug little hole stretching out around the rock-hard girth.

Jay's cock suddenly felt impossibly huge as it opened up the tiniest, most delicate, most private of gateways to her body. In spite of the intense pressure in her ass, Caridad had a boner. She took it in her hand and stroked it as the thick cock moved past the sphincter. She stroked faster while she attempted to keep from cramping. It worked and her sphincter stopped clenching around Jay's embedded muscle and the discomfort of being stretched out again diminished. It still felt strange, but in a good, arousing way. Jay's patience and his gentle caresses on the sensuous ass soothed Caridad. The sense of naughty pleasure radiated from her dilated anus and his pulsing cock.

"Are you okay?"

"Yeah, much better, I think you can give me more now. I'm ready for more cock, Jay, give it to me."

Grabbing the tube and squirting more gel right over his dick and the stretched sphincter, Jay started feeding more of his meat into Caridad's tight ass. He went in as slowly as possible, pressing into her anus with shallow gentle strokes and then stopping, waiting, adding more lube and finally retreating a bit before restarting that gradual anal penetration all over again. Jay pushed himself a little bit further into her taut rectum. He basked in the unique, irreplaceable sensation of fucking a beautiful ladyboy ass. It was a glorious, indescribable feeling, one that he had experienced for the first time just a few days ago. Caridad was so tight that she seemed like an anal virgin. That made Jay delirious with desire as he sank more and more of his thick shaft inside the marvelous ass. He knew he'd be eternally grateful to his pretty lover for allowing him to penetrate the magnificent bottom again and again.

By the time he had managed to wedge his entire length inside the cock hugging rectum, he was on the verge of cumming. The look of the oily distended anus wrapped around the base of his dick and framed by those gorgeous splayed ass cheeks was incredibly erotic. However, it was nothing compared to the feel of being buried to the hilt inside Caridad's beautiful perfectly shaped ass. Not in his wildest imagination would Jay have ever thought that fucking a gay ass would bring him so much pleasure. He had crossed the line and he loved every second of it. He knew then that he would have to have Caridad again and again before they arrived in Barcelona.

The virginal like tightness of Caridad's passage was exquisite. The slippery, velvety warmth of her anal walls snugly enveloped the aching boner from tip to base. As he enjoyed the clenching spasms of Caridad's anus, Jay gritted his teeth and tried his best not to cum too soon. He savored the delicious pressure of the spongy rectum holding firmly onto his dick, milking him and keeping his throbbing shaft cozily trapped in the anal depths.

"I'm all the way inside your ass! Your ass feels incredible, absolutely incredible! You were right; it is as good as any girl's ass, even better."

Caridad was speechless, overpowered by the intense sensations that radiated from her stimulated anal nerve endings and prostate. Without even noticing the transition from pressure to delight, she had started to enjoy getting anally penetrated, actually reveling in the feel of absolute fullness that made her rectum pulse with ecstasy. For Caridad, it was a revelation to have her ass stuffed so full of cock.

Her lover Carlos was not a thick as Jay. Then she thought of her lover who would be picking her up at the terminal when the ship docked. She would have to tell Jay before then and have him swear to secrecy. There was still time for that and for right now she wanted to enjoy the marvelous butt fuck.

"Jay, this is awesome to have so much cock in my ass. You are so deep in me, so hard and big in my ass!"

"You're fantastic, Caridad! Your ass is so hot and so fucking tight! You can't believe how good you look with my big dick in your beautiful bottom."

Just before Jay picked up the pace, Caridad instinctively wiggled her lovely bottom back against him. At first she gently moved her dick stuffed ass but soon she began rocking rhythmically back and forth, butt fucking herself while Jay held still.

"This feels so good!" she moaned as she slid her stretched anus along Jay's tool in slow shallow strokes. She resumed stroking her own cock and cried out, "I love your big hard cock stretching me!"

Jay let Caridad follow her instincts and just watched as she worked her sweet round ass on the thick cock. The shapely frame shivered in delight as she sodomized herself with longer and deeper self-fucking strokes, Jay grabbed the gel and added more of the slick fluid to the portion of his boner that Caridad let glide out of her ass each time she rocked forward.

"You're truly amazing Caridad!" Jay exclaimed as he started to gently hump into the perfect bubble butt. "I mean it, you're so fucking hot!"

"Jay, fuck my ass," she panted, looking back at Jay with a look of desire on her beautiful face. "Really fuck my ass now, I need it!"

Jay let out a contented sigh and started moving inside the warm oily ass. He sodomized her slowly, gently, savoring Caridad's heavenly tightness and losing himself in the spectacle of her dilated anus. Jay withdrew and then gradually pushed himself all the way back inside the smooth welcoming sheath of the slick rectum. As Jay made love to the ass in a calm fluid rhythm, Caridad felt light-headed with pleasure and she could barely find the energy to moan out her cry of ecstasy.

Unable to speak and groaning incoherently, she managed to make her wanton desires clear by pushing her round tush back into the skewering shaft. She urged him to cram his dick harder and faster into her slick anal tunnel. He grabbed the firm round bubble butt in his hands and began driving his stiff meat into the clingy anus with gusto. Caridad and Jay fucked like animals, grunting and gasping together. He loved the rubbery grip that her snug rectum had on his shaft, and he was glad he had used so much lube and took such a long time letting her get used to his girth.

Caridad responded and Jay began ramming his pole into her gripping channel with longer and faster thrusts. He was amazed by the way she kept up with his vigorous rhythm, pushing her curvy bottom back to meet every lustful plunge. Jay picked up his pace even more and started to really pound her, burying himself as deep as he could inside the steamy rectum each time. She just moaned louder and slammed back more frantically, making her perfectly shaped tush slap against Jay's groin. She stroked her erect cock ever more desperately as he reamed her surrendered ass, she yelped and whimpered in unrestrained pleasure, an indication how much she loved every passionate second of the butt stretching sodomy. Jay found it immensely erotic to see how aggressively Caridad was participating in their anal coupling, his clear appreciation of their ass fuck fueled his ravenous desire to mount the beautiful bottom again and again and again. He didn't want this cruise to end.

As time flew by, the two new lovers got totally consumed by their shared anal lust. Caridad suddenly started yelling out and thrashing as if she was having a fit. She rapidly stroked her cock and cried out as she spewed semen all over the bed covers. "Oh God, Jay, I'm cumming." Caridad's anal orgasm was unlike anything she had ever felt. It felt like her whole body was cumming. It was unbelievably, unbearably good.

Looking over her shoulder, Jay watched as five or six streams of semen shot out of his lover's cock. Her sphincter clamped firmly around him and the taut rectum milked his cock in deep suctioning squeezes, He fought to ride out his monumental climax bucking his hips harder to keep driving his pole in and out of the contracting snug anus. He grabbed onto her round buttocks and jammed himself forcefully inside her ass over and over again. Jay was now desperate to cum with her.

Lost in her mind-blowing orgasm, Caridad was so far gone that she couldn't even hold herself up on her knees. Her legs buckled as Jay pillaged her twitching ass, butt fucking her with all he had. When Caridad fell forward, Jay went down with her. Holding onto her curvy rump, he plowed the enveloping anus with abandon, pressing himself onto her sweat slick back. Spreading her legs wide as she lay on her belly was all she could do while Jay's huge cock glided in and out of her clenching rectum at a furious pace.

Lying on top of Caridad, pumping his raging boner wildly into the tight slippery ass as he rushed to his climax, Jay went rigid and unleashed a savage flurry of butt drilling strokes. As his balls drew up and his cock started to flex erratically in the depths of the conquered ass, he rested his head in the hollow of her shoulder and nuzzled her neck. Nearing what he knew would be a massive ejaculation, he whispered into her ear.

"I'm going to cum, Caridad, in your tight beautiful ass, here it cums, ah so good!"

"Yes! Ugh, cum in my ass! Oh, fuck me harder, faster deeper oh Jay!"

With one final powerful thrust, he buried his cock balls-deep inside the amazing ass and came like a geyser, crying out with the pleasure of his release. The feel of hot cum flooding the rectum in a deluge of thick jetting spurts sent Caridad over the edge once more. She groaned as her cock, pressed into the bed, spurted underneath her while Jay's huge pulsating cock shot rope after rope of creamy sperm into her bowels, filling her anal tunnel with a massive load.

Caridad was high on the sensation of Jay's ejaculating shaft throbbing crazily inside her spasming hole. Jay's cock felt even bigger and harder as he kept spraying a torrent of warm semen deep in her ass, taking her breath away. At the same time, the powerful contractions of the anal walls amplified Jay's pleasure beyond anything he had ever felt. As she milked his thick pole from tip to root within her clenching rectum, Jay basked in the incredible sensation of the already snug rectum tightening rhythmically around his spurting dick.

Only after Jay was done pumping the ass full of cum did Caridad's slender frame finally stop writhing in delight. For a while, the sated lovers could merely lie as they were on the bed in a drained heap, breathing raggedly. Motionless, they enjoyed the afterglow in silence, their minds floating away as the thin layer of perspiration between his chest and her back glued their bodies together.

When Jay stirred from his momentary absence, he realized that he was still on top of Caridad with his cock sheathed to the hilt inside her snug, cum-flooded ass. He had lost his aching rock-hardness but he was still pretty stiff, thanks to the rush of pure anal lust still coursing through his veins, not to mention the awesome tightness of the sperm-coated rectum and the delicious clamping grip of her anus wrapped firmly around the root of his dick. Not wanting to crush his petite lover, he rolled to his side pulling her with him and keeping his cock in the warm poop chute.

Spent, the lovers stayed spooned tightly for long lazy minutes, basking in their shared intimacy. The quiet joy of their afterglow started fading only when his wilting cock finally plopped out of her ravaged bottom with a lewd squishy sound. The sudden sense of emptiness in her gaping anus made her groan sensuously. Caridad could feel the warm cum oozing out of her unplugged rectum and trickling out of her body in thick gooey rivulets. Wiggling free of Jay's bear hug, she rolled on her belly with a look of determination on his delicate face. Her hands were holding her curvy ass wide open with lust glinting in her eyes as she looked over her shoulder at Jay who was fixated on the dilated anus.