


Transsexual Journey

by walterio



Category: Transsexuals & Crossdressers
Published: 2016-11-20
Updated: 2016-11-25
Packaged: 2017-04-19 18:33:12
Chapters: 3
Publisher: literotica.com
Story URL: https://www.literotica.com/s/transsexual-journey-01
Author URL:
https://www.literotica.com/stories/memberpage.php?uid=429765&page=submissions
Summary: <p>1. Single stud meets a lady boy on a Trans Atlantic cruise.</p>
<p>2. Jay's transatlantic cruise and transsexual journey continues.</p>
<p>3. Jay and Caridad wrap up their erotic cruise.</p>
Erotica Tags: Anal Foreplay, Anal Sex, Beautiful Ladyboy, First Time With A
Trannie, Incredible Ass, Insatibale, Large Thick Cock, Oral Sex, Transsexual
Sex, Transsexuals & Crossdressers, Voluminous Ejaculations
Average Rating: 4.47





TABLE OF CONTENTS


Transsexual Journey 01

Transsexual Journey 02

Transsexual Journey 03




        Transsexual Journey 01


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.




        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.  

The sight of semen bubbling out of the gaping anus was obscenely erotic and
Jay stared at it. The slick rubbery nether hole remained open, stretched out
of proportion by the long fat cock that had been inside it for nearly an hour.
The edges were smeared with white dollops of cum that were slowly trickling
down to her ball sac. If Jay had anything left at the moment, he would have
gotten another raging erection just looking at the well-fucked ass.  
  
He watched as her anus returned to its normal tiny size and its cute little
rosebud appearance. It still looked inviting so he scooped up some semen and
rubbed gently around the abused pucker soothing it with his seed. As he stared
at it and played with it, he was amazed that he had been able to get his big
cock in that seemingly tiny entrance.  
  
"I have to tell you Jay that was the best fuck of my life."  
  
"Mine too."  
  
"Really, am I as good as any woman?"  
  
"Absolutely, I'm looking forward to more of your sweet ass, but that will have
to wait until tonight. You wore me out and I have nothing left."  
  
"Let's get cleaned up and hang out by the pool today if we can find a spot."  
  
"Okay, do you wear a swim suit?"  
  
"Of course I do. If you are worried about my little cock showing, don't. I
have been doing this for a while."  
  
They showered separately and donned their swimwear. They briefly admired each
other's body again before leaving the stateroom and heading to the swimming
pool. It was close to lunch time and they were fortunate to find a spot around
the crowded pool as some people were just leaving. They spent the day by the
pool and then went back to their own rooms to get ready for dinner.  
  
After dinner that night they stopped in the cocktail lounge for a drink.
Caridad excused herself to use the bathroom and Pedro the bartender admired
her as she walked out of the lounge. He turned to Jay and spoke.  
  
"You are a very lucky man to find such a beauty on this cruise."  
  
"Yes I am Pedro; she is really something. I never expected to run into anyone
quite like her."  
  
"Are you going to the show tonight. It is a comedian and he is very funny."  
  
"Yes we plan to, thank you!"  
  
Caridad returned and they finished their drinks. Jay tipped Pedro generously
as he always did and then they went to the show room to see the comedian.
Pedro was right the guy was hilarious and had everyone laughing out loud.
After the show, they had a night cap before returning to Jay's stateroom. As
she had done before, Caridad stopped in her room to pick up a change of
clothes. While waiting for her, Jay thought of his life changing event and how
it started with his friend having to cancel the trip. He would have never met
Caridad and he was certain that he would have never met a ladyboy in his life.




        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.  

"That was quite a wakeup call," Caridad sighed, "However, I have to get going.
I have a hair appointment at 11:00 AM"  
  
"Okay I'll see you later then."  
  
"No Jay, this is goodbye for us. I will be meeting my boyfriend later at the
terminal after the ship docks. I cannot have him suspicious of us. Please do
not acknowledge me again after I leave your room."  
  
Jay was a bit put out but he also understood what Caridad was asking, "Of
course, I understand. I have to say though that this week was a very special
one."  
  
"Yes Jay, one I will remember for a long time."  
  
With that brief exchange, Caridad gathered up her thing and returned to her
own stateroom. There she would shower, pack and lay out her clothes for
departure. She would first grab a quick bite and then go to the spa to get her
hair done. Jay showered, dressed and made his way to the brunch. While he ate,
he re-played the events of the week in his mind. Caridad had proved to be an
accomplished lover and one he would not soon forget.  
  
After the brunch, all the passengers had packed their belongings and had
proceeded to the main terminal where the customs check-in was located. Jay was
in a different line as Caridad was a resident of Spain. Still later he saw her
claim her luggage and then greet a very handsome Spaniard. He watched the two
of them embrace and kiss before turning his attention back to his own entry
into Spain.  
  
Once he cleared customs he retrieved his luggage and proceeded to the taxi
stand. He was tired and sexually sated. When the driver offered to take him
somewhere that evening he declined. He told the taxi driver to pick him up the
next night and he would go clubbing. Jay was ready to get back to some pussy
but not his first night in Barcelona after a week with Caridad.




End file.

