


His Own Personal Ladyboy

by walterio



Category: Transsexuals & Crossdressers
Published: 2012-10-15
Updated: 2014-11-19
Packaged: 2017-04-22 01:58:34
Chapters: 3
Publisher: literotica.com
Story URL: https://www.literotica.com/s/his-own-personal-ladyboy-ch-01
Author URL:
https://www.literotica.com/stories/memberpage.php?uid=429765&page=submissions
Summary: <p>1. Cliff acquires a ladyboy after meeting his uncle's
ladyboys.</p>
<p>2. Cliff and Jodie settle in and then they visit Uncle Jack.</p>
<p>3. After some shocking news Cliff settles in with the ladyboys.</p>
Erotica Tags: Anal Sex, Bisex, Gay Sex, Group Sex, Ladyboys, Massive Cum
Shots, Oral Sex, Surprise Seduction, Thai Kathoey, Transexuals, Transsexuals &
Crossdressers
Average Rating: 4.53





TABLE OF CONTENTS


His Own Personal Ladyboy Ch. 01

His Own Personal Ladyboy Ch. 02

His Own Personal Ladyboy Ch. 03




        His Own Personal Ladyboy Ch. 01


PRELUDE  
  
Cliff was driving back to his condominium with his recently acquired Kathoey
when he noticed Jeidee looking at him with interest. Cliff smiled and asked if
there was anything wrong. Jeidee replied, "No I was just wondering how big
your cock is and how it might feel in my ass later."  
  
"Why don't you find out for yourself? We still have nearly an hour before we
get home," Cliff suggested.  
  
Jeidee leaned over toward him and unzipped the fly of Cliff's pants. He fished
around inside Cliff's underwear and grasped the stiffening shaft. By the time
Jeidee had the cock out of Cliff's pants it was rock hard.  
  
"I like this, big but not too big," Jeidee said sexily.  
  
Jeidee's tongue licked around the shaft before it disappeared into Jeidee's
mouth. Cliff tried to concentrate on his driving as he received one of the
best blow jobs ever. Cliff was already turned on by the prospect of fucking
Jeidee later so it did not take long for him to cum in Jeidee's mouth. Cliff
had one hand on Jeidee's head running it through the shiny long black hair as
Jeidee sucked his cock. When Cliff ejaculated, Jeidee stayed glued to the big
dick and swallowed every drop.  
  
Once Cliff was sucked dry, Jeidee put Cliff's cock back in his pants. "That
was marvelous, you are a very good cocksucker," Cliff said with a sigh of
relief.  
  
"Do you know what to expect from now on?" Cliff asked.  
  
"Yes, I will serve as your house ladyboy and you are going to help me become a
girl," Jeidee replied.  
  
"That's right. You are off to a good start since you have been taking female
hormones. Your breasts are starting to develop and you hair is long and silky.
You can pass for a girl now but we will still make improvements. Any worries?"  
  
"No, Lei Lin said that you are a very kind man and that I have nothing to
fear. I am glad that I wasn't sold to someone who abuses their ladyboys,"
Jeidee responded.  
  
"I never get that. Why does a guy have to abuse a woman or any lover for that
matter," Cliff stated and then said, "I have always liked the name Jodie and
since your Thai name is so close to that, from now on you will be known as
Jodie."  
  
"Jodie, I like that," Jeidee agreed.  
  
"Tomorrow I will take you shopping so that you can select some sexy women's
clothes. I know that you already have a couple of dresses but we will set you
up with a complete wardrobe. We need to get you a bikini swimsuit too," Cliff
offered.  
  
Just then the car pulled into the condo complex and Cliff parked in his
assigned garage. Jodie took his bag from the car and followed Cliff into the
condo. Jodie would start a new life together as Cliff's servant. Jodie had
learned that Cliff still dated girls but that he was drawn to pretty ladyboys
too. Jodie would respect Cliff's bisexual lifestyle and serve him as expected.  
  
CLIFF'S FIRST LADYBOY EXPERIENCE  
  
Cliff was a successful management consultant who worked for a virtual office
company. That meant that Cliff's office was his home when he wasn't at client
sites. He had purchased a three bedroom condo in Orange County, California.
Cliff used one of the bedrooms as his office and the other as a guest bedroom.
He traveled often and he liked his lifestyle. Cliff had met a number of flight
attendants who he dated and slept with which fit their traveling lifestyles.  
  
Cliff was a handsome young man of 28 years and he was very fit. He loved to
surf, SCUBA dive and play tennis. At 6'2" he weighed a fit 185 pounds. He had
light brown hair with hazel eyes and an engaging personality. The condo
complex had a fitness center and a swimming pool both of which Cliff used
often. His sex life was satisfactory and he never thought about sex other than
with a woman. However one weekend at his uncle's home changed that.  
  
On a Friday evening Cliff drove to the exclusive suburbs where his uncle Jack
lived. It was his first time he had been invited to his uncle's home and as
Cliff turned into the gated community he admired the entrance. The guard had
Cliff's name on the guest list and he gave Cliff directions to his uncle's
house. Cliff drove slowly and took in the mansions and estate like homes. One
was bigger and more stunning than the next. Then he located Uncle Jack's house
and pulled in the large circular driveway. Cliff was impressed with the house
and thought that some day he might live like this.  
  
Cliff made his way up the walk to the front door and he rang the bell. The
delightful chimes echoed through the house and within seconds the front door
was opened. Cliff was greeted by a beautiful Asian girl wearing a jade color
silk dress. The dress had a high collar on it and it covered her neck. The
girl's hair was jet black and it was pulled back and tied into a long
ponytail. Cliff stared at her in all her beauty before stepping into the
foyer.  
  
"Master is expecting you, please you follow me," the girl said in a soft
voice.  
  
Cliff followed her into the main part of the house. He noticed that her jade
dress was cut up the side of both legs all the way to the thigh. The dress
emphasized her shape as it hugged her small breasts and her perfect round ass.
Cliff watched her walk in front of him and he focused on her ass as it
undulated beneath the tight fitting dress. Cliff felt his loins stir just from
looking at her.  
  
Cliff was led into the den where Uncle Jack was nursing a scotch. "Hey it's
great to see you. Shit what has it been two years? I'm glad you moved to
California. I see you have met my housekeeper Kulap. You will meet my other
housekeeper in a few minutes. Kulap, please bring Cliff a drink," Jack
directed.  
  
Kulap made a slight bow and then left the room. When she returned with Cliff's
drink the other housekeeper walked in with a tray of snacks. Cliff looked at
the other girl and she looked almost identical to Kulap except that her dress
was gold.  
  
"Cliff this is Mali," Casey said introducing her.  
  
"Pleased to meet you," Cliff said.  
  
The two girls bowed slightly and then left the room. Cliff watched as an ample
amount of leg peaked on the sides of both dresses and their cute round asses
rolled with each step. Cliff couldn't believe how beautiful they both were.
Mali and Kulap looked like two porcelain dolls, they were that fine. Cliff
immediately wondered if Uncle Jack was fucking both of them.  
  
"They have great asses, don't they?" Jack said as if he was reading Cliff's
mind.  
  
"They're beautiful!" was all Cliff could say in reply.  
  
"Hey, cheers!" Jack said raising his glass to Cliff.  
  
Cliff returned the toast, "Cheers!" and he lifted his glass to Jack.  
  
"Come on bring your drink and I'll show you the place while Mali and Kulap get
dinner ready," Jack offered and added, "I hope you like Thai food."  
  
Cliff picked up his drink and followed Jack around the house. Cliff was
impressed with the house and décor. Jack showed him the first floor and lower
level as there were only bedrooms and baths on the second level. On the main
floor was the living room, dining room, library, den, kitchen, breakfast area,
a gathering area and two bathrooms. The lower level was really interesting
where there was an exercise area, bar, game room, two more bathrooms and a
room Jack called the relaxation room. The relaxation room had several lounges,
a massage table and a large Jacuzzi.  
  
"I have a lot of fun in this room with Mali and Kulap," he remarked to Cliff.  
  
Cliff felt his cock swell just from the thought of being naked in the
relaxation room with Mali and Kulap. He imagined his uncle in the Jacuzzi
naked with his two housekeepers and then getting a massage from them. He
wondered if his uncle ended up fucking the two of them. Jack told Cliff that
outside there was a swimming pool and another Jacuzzi, a cabana and plenty of
lounge chairs and that it was very private and that he often swam in the nude
outside. Then Jack took Cliff back upstairs to check on dinner.  
  
Kulap told them that dinner was ready to be served so Jack and Cliff took
their seats at the dining table. Mali opened a bottle of wine and Jack gave
his approval after tasting it. Mali and Kulap then brought the food out from
the kitchen and served Cliff and Jack. Cliff could not take his eyes of Mali
and Kulap as they moved around the table and made several trips to the
kitchen. He constantly caught glimpses of their bare legs through the slits in
their skirts but it was their shapely asses that he salivated over.  
  
Cliff was surprised but pleased when Mali and Kulap sat down at the table to
dine with them. The meal was fantastic and Cliff enjoyed everything that was
prepared. Mali and Kulap guided Cliff through the Thai dishes and explained
what sauces and spices to use. Jack cautioned him on one spice.  
  
"Cliff, be careful with that one. It will burn the skin in your throat and
scald the hairs in your nose," Jack said with a boisterous laugh.  
  
Kulap told Cliff that it was very hot and to try just a tiny bit. She moved
over to Cliff and took a speck and placed it on Cliff's plate. As she did she
pressed her breast against his arm then she smiled at him as she moved back to
her seat. Cliff tasted the spice as directed by Kulap and Jack was right. Just
that little speck set his mouth on fire. He quickly slugged down some wine as
the three of them laughed.  
  
After dinner Jack and Cliff adjourned to the den and Jack poured them after
dinner drinks. They chatted some more while Mali and Kulap cleaned up the
dishes. Jack had taken a liking to his nephew Cliff and it was obvious. Jack
refreshed their drinks just as Mali and Kulap came into the den. They stood
there as if waiting for their next assignment.  
  
Jack looked over at Cliff and asked, "Cliff, are you in the mood for a blow
job?"  
  
Cliff couldn't believe what he heard and stammered his response, "Did I hear
you right, a blow job?"  
  
"Yes you heard correctly. Mali and Kulap give wonderful blowjobs and I know
that they think you are very handsome," Jack told him.  
  
Cliff blushed but replied, "How could I refuse an offer like that?"  
  
Mali and Kulap smiled and they walked over and knelt on either side of Cliff.
He slid forward in the chair as they unbuckled his belt and unfastened his
trousers. Cliff then lifted his hips as they tugged his pants and underwear
down past his knees. Cliff was already hard when his cock came into view. It
sprung up when his underwear cleared his pubes and he heard gasps from Mali
and Kulap.  
  
"They like your big cock Cliff. This will be a real treat for them as well,"
Casey said.  
  
"What about you Jack, aren't you going to get one too?" Cliff asked.  
  
"No not tonight. I'm not young anymore like you. So I want to save myself for
when I fuck them later," Jack replied.  
  
Cliff watched as the two delicate mouths moved up and down on the side of his
shaft with their lips pressed together. The slit skirts spread out and Cliff
could see an ample amount of leg flesh showing. He was really turned on and he
knew that it would take everything he had to control an early ejaculation.
Kulap wrapped her hand around the base of Cliff's cock. She held his balls and
cock in one hand with his balls resting on her thumb. She held him snugly and
as a result his ball sac was stretched tight.  
  
Kulap then began to lick his tight ball sac and at the same time Mali lowered
her mouth to engulf his cock. Cliff wanted to reach down and grab both pony
tails as they worked on his cock but he thought better of it. Instead he just
watched as the two beauties worked over his cock as they took turns sucking
it. Cliff then felt his balls really tighten as his orgasm built in his loins.
Kulap seemed to sense his pending ejaculation and she covered his cock with
her mouth.  
  
Cliff groaned as he came and filled Kulap's mouth with cum. Kulap took the
first two streams in her mouth and then she passed the cock to Mali so that
she could receive the next burst of cum. Mali took a couple a shots and then
passed it back to Kulap. The two of them passed Cliff's cock back and forth
until he was drained of every drop of cum. Mali and Kulap were extremely
efficient as not a single drop of semen was missed. Cliff just leaned back in
the chair and groaned.  
  
"Well done Mali, well done Kulap," Jack complimented them and then he said,
"Come on Cliff, tidy yourself up, grab your drink and we'll head downstairs."  
  
Cliff pulled his pants back up and followed Jack to the lower level. Cliff's
head was spinning as he couldn't believe the incredible blow job that he just
received from the two beauties. He had forgotten all about his uncle sitting
in the den watching them. It was the first time that two people sucked his
cock at the same time and the first time someone watched him get sucked off.
It had been wild.  
  
"I thought we would hit the Jacuzzi and then get a massage from Mali and
Kulap. Are you up for that?" Casey asked.  
  
"Sure that sounds great," Cliff babbled.  
  
"Good you can put your clothes over there. Bring your drink with you," Casey
instructed.  
  
Cliff knew he didn't have to ask about a bathing suit as it was obvious they
would go in the Jacuzzi naked. Cliff wondered if Mali and Kulap were going to
join them in the Jacuzzi and he soon had his answer. Cliff and Jack were
already in the water when Mali and Kulap entered the room. They were both
wearing silk kimono robes and Cliff hoped that they were naked underneath.
Cliff stared at them as they turned their backs to him and dropped their
robes. They were naked as Cliff had hoped and their beautiful shapely bodies
were on display.  
  
Cliff took in their beauty from head to toe. He admired their slender shapely
legs as his eyes traveled upward to their buttocks. He stared at their
incredible curvy asses which looked perfect, their waists were narrow and
their skin was flawless. Mali and Kulap released their ponytails and their
silky black hair draped over their shoulders. Cliff's cock was rock hard by
now.  
  
Then Mali and Kulap turned around and faced Cliff and Jack. Cliff looked at
their pretty faces and small but perfect tits briefly. Then his eyes dropped
and looked at their pussies. However they didn't have pussies they had dicks.
Mali and Kulap were boys and they had cocks, small cocks but they were
definitely cocks.  
  
"Aren't they something?" Cliff heard Jack say and then, "Cliff I would have
never shared this with you if I didn't like you and know that you would be
discreet. I thought you would really like Mali and Kulap. Wait until you fuck
them in the ass, you already know what good cock suckers they are."  
  
Cliff kept staring at the pretty boys somewhat in disbelief but at the same
time in admiration of their incredible effeminate bodies. Mali and Kulap then
walked toward Cliff and they entered the Jacuzzi. The little cocks hardened
and Cliff noticed that they were very small, maybe just a couple of inches
when hard if that. Uncle Jack was also hard now and Cliff noticed that he had
an average cock. Mali and Kulap stood close to Cliff and ran their hands over
his body. They lifted his balls and stroked his cock as they pressed their
small firm tits into his body. Then Kulap moved over to Jack and she began to
stroke him as well.  
  
They stayed in the Jacuzzi for several minutes engaging in foreplay until Jack
announced it was time for a massage. Cliff and Jack got out of the water and
Mali and Kulap dried them with large fluffy towels. Cliff and Jack then
stretched out on massage tables as Mali and Kulap retrieved the body oils.
Mali massaged Cliff as Kulap massaged Jack. Jack and Cliff were face down as
Mali and Kulap worked the oil into them, first the shoulders, then the back,
buttocks and legs. Jack and Cliff then turned over and their erections were
sticking up in the air. Mali massaged Cliff's chest, abs and legs skipping his
pubes. Then she returned to is pubes and she lovingly stroked his cock. Cliff
knew he would cum if she kept it up. Just then Jack spoke.  
  
"Okay, let's go to the lounges. Cliff I'm going to fuck both asses first and
loosen them up for your bigger cock," Jack stated.  
  
Mali and Kulap took up the subservient doggy-style position on the lounges as
Jack lubricated both assholes. Even though Cliff had never fucked a male ass
before he was suddenly dying to get his cock into one of their asses as he
watched Jack prepare them for anal sex. Mali and Kulap had their heads down
turned toward each other. They reached out and held hands as Jack worked on
their asses. Then Jack moved behind Mali and eased his cock into the shapely
ass. Mali groaned with the anal penetration and squeezed Kulap's hand tightly.
Jack didn't fuck Mali for very long and then he moved over to Kulap and began
fucking him.  
  
"Mali is ready for you now Cliff, but take it easy with that ass buster of
yours," Jack told Cliff.  
  
Cliff moved quickly behind Mali and lined up his cock with Mali's asshole. He
pushed in and found the fit to be very snug but his cock steadily entered
Mali's ass. Mali grunted as he felt the large cock make its way into his ass.
Mali placed a hand on Cliff's thigh as a reminder to go slow.  
  
"Oh Kulap, he so big but feel so good!" gasped Mali.  
  
Cliff began to fuck Mali slowly and each time he moved forward his cock went a
little deeper. Mali moaned and groaned each time the cock went deeper and
touched new areas in his rectum. Soon Cliff had his 7+ inches buried in Mali's
ass. Cliff loved the way Mali looked on all fours. Mali looked submissive and
delicate as Cliff's big thick cock reamed his ass. Cliff was close now and he
knew that he was going to shoot an enormous load in Mali's ass. Cliff thrust
all the way in and groaned out loud as he came in Mali's ass. Jets of cum shot
into Mali's ass and quickly filled his rectum to overflowing. As Cliff resumed
fucking Mali, cum ran out of Mali's ass and down over his balls. Mali's anal
muscles were working furiously milking Cliff's cock.  
  
Cliff pulled his cock from Mali's ass and watched as cum oozed out and ran
down between Mali's buttocks and over his balls. Cliff had forgotten all about
Jack and Kulap next to him. Jack had finished fucking Kulap but Jack did not
cum as he was saving himself for later. Mali and Kulap collapsed on the mat,
cuddled and kissed. Then Kulap rotated his body and Kulap and Mali sucked each
other's cock. Cliff was still hard and Jack marveled at his nephew's stamina.  
  
"Ah to be young again, it looks like your still up for another round. Take
Kulap's ass this time," Casey directed.  
  
Cliff got behind Kulap at the same time that Jack got behind Mali. Cliff
fucked Kulap's ass at the same time that Jack fucked Mali's ass while Mali and
Kulap sucked each other's cock. It was Cliff's first ever bisexual and group
sex and it was incredible. It took Cliff longer to cum this time but when he
did he flooded Kulap's ass just as he had with Mali. Jack also came this time
and dumped his load in Mali's ass. Cliff removed his cock from Kulap's ass and
Jack pulled out of Mali's ass. Kulap and Mali stayed in the 69 position and
continued to suck each other's cock until they both ejaculated.  
  
Jack and Cliff moved over to the lounge chairs at Jack's direction and they
watched Mali and Kulap pleasure each other. Cliff was still amazed how much
they looked like girls and beautiful girls at that. After Mali and Kulap
separated they returned to the Jacuzzi and allowed the jets to cleanse their
bodies. Then they dried off and put their robes back on. Jack told them to
refresh the drinks and they left the room.  
  
"So Cliff what do you think of my ladyboys?" Casey asked.  
  
"Is that what you call them, ladyboys?" Cliff asked.  
  
"Yeah actually kathoeys that's a term they use in Thailand for ladyboys where
they are trained."  
  
"They are trained to do this?"  
  
"Yeah there are a number of them in the states and in Western Europe. I found
out about them through a business associate."  
  
"Wow, but why train boys, why not Thai girls?"  
  
"Oh they train girls too but the boys seem to be more plentiful. I could have
waited for girls to become available but there was a long waiting list and I
wanted two of them. Besides I prefer anal sex and the ladyboys suit me just
fine."  

"I can't believe how much they look like girls though."  
  
"Yeah I know. They both take female hormones, which is why their breasts are
developing and their bodies are so shapely," then Jack asked, "Cliff why don't
you stay the night?"  
  
"Really, I'd love to."  
  
"Sure I have plenty of room and I know that Mali and Kulap would like more of
your cock."  
  
"Sounds good to me," Cliff exclaimed.  
  
Just then Mali and Kulap returned with the drinks. They served Jack and Cliff
and then left the room. Cliff and Jack were still naked and they sat around
drinking and talking as it was the most natural thing in the world. Cliff was
thrilled to be in his uncle's company and Jack really liked his young
adventurous nephew Cliff. They finished there drinks and Cliff went to pick up
his clothes.  
  
"Cliff leave them, the boys will take care of them. Come on I'll show you to
your room," Jack told him.  
  
They both walked upstairs naked to the bedrooms and Jack showed Cliff the
guest room. Cliff was surprised to see that the guest room had its own bath.  
  
I'll send the boys in and they will turn down the bed and get you anything you
need," Jack told him and then said, "Goodnight, I hope you sleep well."  
  
Jack left the room and then Mali and Kulap entered. They turned down the bed
covers and Cliff watched them closely. As Kulap was leaning over the bed Cliff
ran his hand over Kulap's ass. Kulap looked over his shoulder and smiled then
he dropped his robe and continued working on the bed. Cliff got the message
and he played with Kulap's ass. Cliff fondled the pretty buttocks and fingered
the tight anus. Cliff felt his cock harden and he rubbed it over Kulap's
buttocks. Mali then dropped his robe and got in bed on all fours.  
  
"We all fuck one more time, okay?" Kulap said.  
  
"Okay," Cliff gasped.  
  
Kulap got behind Mali and slid his cock into Mali's ass. Then Cliff got on the
bed behind Kulap and put his cock in Kulap's ass. Kulap did all the work as he
thrust into Mali's ass and impaled his ass on Cliff's cock. Kulap picked up
the pace in search of his own orgasm and as he did he drove Cliff toward
another one as well. Cliff stiffened and came for the fourth time that night
and he knew that he was done. His cock slipped from Kulap's ass as he went
soft faster this time. Kulap came in Mali's ass and then Mali turned around
and sucked both Kulap's cock and Cliff's cock dry.  
  
Mali was now hard so he fucked Kulap's ass. Cliff watched the two of them fuck
right next to him in the same bed. After Mali came, Kulap turned around and
sucked Mali's cock. Cliff was in awe of how beautiful the two of them looked
together. Mali and Kulap then got out of the bed and put their robes back on.
They said goodnight to Cliff and bowed slightly as they left the room. Cliff
lay in bed thinking that he could get used to having a ladyboy around. He
thought it would be cool to have a Thai housekeeper. Cliff then dozed off in
one of the most comfortable beds he had ever slept in.  
  
SATURDAY AT UNCLE JACK'S  
  
Cliff woke up early with his bladder about ready to burst. He went into the
bathroom took his morning piss and then he returned to bed. He had no trouble
falling back asleep and within minutes he was in a deep sleep. Cliff had a
wonderful dream that he was surrounded by pretty Thai ladyboys and they
couldn't get enough of his cock. In the dream his cock seemed to stay hard
forever as he fucked countless mouths and assholes. Cliff slowly woke up to
find Mali and Kulap naked in bed with him sharing his cock.  
  
Just as they had done in the den last night they took turns sucking his cock.
When Mali sucked his cock, Kulap licked his balls. Then Mali passed off
Cliff's cock to Kulap who took it as deep as she could. Mali ran her fingers
over Cliff's scrotum and lightly scratched his perineum. Cliff blew his load
without warning and Kulap calmly swallowed the first several discharges. Kulap
then passed the cock to Mali who received the next series of cum shots and
then she passed it back to Kulap. Kulap sucked some more and then the cock
went back to Mali. Cliff was beside himself with the eroticism of the moment.
Finally with his cock sucked dry, Kulap and Mali kissed as they had done the
last time. Cliff lay back in bed and watched as the two beauties kissed and
shared cum between them. Then they broke the kiss and smiled at Cliff.  
  
"Master say you get up now for breakfast. We fuck later," Mali told him as
Kulap nodded, smiled and said, here clothes."  
  
Then Mali and Kulap left the room. Cliff got out of bed and took a quick
shower and then dressed for breakfast. He noticed that his clothes had been
cleaned and pressed. Cliff made his way down to the breakfast area where Uncle
Jack was already there reading the morning newspaper.  
  
"Good morning, how did you sleep?" Jack asked.  
  
"Like a rock it was the best night's sleep I had in a long time," Cliff told
him.  
  
"Good, how was your wake-up call?" Jack asked with a snicker.  
  
"The best," Cliff replied with a laugh and then said, "You know hotels could
do very well offering a service like that."  
  
Jack laughed and said, "Have some coffee," as he pushed part of the newspaper
toward Cliff.  
  
After breakfast Jack and Cliff put on a couple of terry robes and went out to
the swimming pool area. They were both naked under the robes and sat in the
lounge chairs drinking coffee and discussing Mali and Kulap. Cliff learned
that Jack paid a large sum of money to the organization that trained and
placed the ladyboys. He also gave Mali and Kulap and allowance of a thousand
dollars a month in addition to free housing and food. Jack also took care of
all their medical expenses when they arose.  
  
Mali and Kulap then joined them at the pool and they too were just wearing
robes now and Cliff knew that they would be naked under them. Shortly
thereafter, Mali and Kulap shed their robes and then applied suntan lotion to
each other's body. Cliff watched as they took turns covering every inch of the
other one's body. Cliff got an erection and he put his hand inside his robe to
stroke it. Jack noticed this and spoke to Cliff.  
  
"Go ahead and fuck one of them if you want," Jack told Cliff.  
  
Mali and Kulap looked over at Cliff and smiled. "You come and fuck Kulap
first," Mali said.  
  
Cliff stood up and dropped his robe on the lounge. He walked over to the two
ladyboys with his erect cock sticking straight out. Kulap got on all fours on
the lounge chair and Mali lubricated Kulap's asshole in preparation for
Cliff's cock. The Mali lubricated Cliff's cock and lined it up with Kulap's
asshole. Mali held onto Cliff's cock so he wouldn't go too deep as he pushed
forward. As soon as Mali felt that Kulap's ass had loosened up sufficiently
she let go of Cliff's cock. Cliff then went deeper into Kulap's ass and fucked
him with long steady strokes.  
  
"You pull out this time," Mali said indicating that he didn't want Cliff to
cum in Kulap's ass.  
  
Mali played with Kulap's tits and Kulap's cock as Cliff fucked Kulap. Then
Cliff felt his release build up in his scrotum and pulled his cock from
Kulap's ass. Mali took a hold of his cock and jerked it as Cliff fired streams
of cum onto Kulap's body. The first shot hit Kulap in the head and left a
trail from his hair down to his lower back. The next couple of shots covered
Kulap's shoulders and back. The final couple of shots landed on Kulap's ass.
Mali continued to jerk Cliff's cock and move it around on Kulap's ass. Mali
used Cliff's cock to spread cum all over Kulap's buttocks and then Mali pushed
Cliff's cock back into Kulap's asshole. Kulap then used his anal muscles to
milk Cliff's cock dry.  
  
"Wow that was some show!" Jack exclaimed as he stroked his cock and then
called to Mali, "Come here Mali I need your mouth."  
  
Mali went over to Jack and sucked Jack's cock until he came in Mali's mouth.
Then Mali and Kulap went into the swimming pool with Jack and Cliff who
relaxed in the water as Mali and Kulap played with each other. At one point
Kulap sat on the side of the pool while Mali sucked Kulap's cock. Then they
changed positions and it was Kulap's turn to suck Mali's cock. This got Cliff
hard again and he wanted to fuck Mali this time.  
  
Cliff put a rubber raft in the pool and he had Mali lay flat on it face down.
Cliff pulled the raft into the swallow end where he could stand with his cock
out of the water. Cliff then had Kulap lube Mali's ass with lotion as Cliff
applied the lotion to his cock. Cliff moved closer to Mali and eased his cock
into Mali's ass. Cliff fucked Mali slowly and used the raft to push and pull
Mali back and forth. It was an erotic scene and it caused Cliff to cum quicker
then he normally would have under the circumstances.  
  
Kulap realized that Cliff was close to cumming so he pulled Cliff cock from
Mali's ass and held it under water. Kulap felt Cliff's cock throb and pulse as
he ejaculated into the pool. Jets of semen flew out of Cliff's cock and formed
into milky cloud under the water. It was incredibly erotic to see cum shooting
under water. Kulap used his fingers to play with the milky cum in the water
and giggled as he tried to pick it up. Kulap continued to jerk Cliff's cock
and then he leaned over and took Cliff's cook in this mouth. Kulap sucked
Cliff's cock dry and Cliff knew he was done for the day. Cliff got out of the
pool, dried off and then sat naked in the lounge chair. Jack, Mali and Kulap
also got out of the pool and sat naked in the lounge chairs. Cliff excused
himself to go get dressed as he knew it was time for him to leave.  
  
Cliff returned to the pool and thanked Uncle Jack for a wonderful weekend.
Mali and Kulap smiled and waved goodbye as if they were two little nymphs.
Cliff left the property and then drove home. He made up his mind to
investigate buying a ladyboy.  
  
CLIFF DECIDES TO BUY JEIDEE  
  
For days Cliff pondered the question, "Should he buy a ladyboy?" It was a big
commitment but the more he thought about it the more he leaned toward it. He
had enough money saved up based on what his uncle told him they cost. Cliff
decided he would contact Lei Lin and tell him of his interest.  
  
When Cliff spoke with Lei Lin the man was pleased to learn of Cliff's
interest. Lei Lin was also pleased because he knew Cliff's uncle. "I have a
very special Kathoey available right away. His name is Jeidee but he looks so
much like a young girl that you have to see him to believe it," Lei Lin told
him.  
  
"When can I meet him?" Cliff asked with excitement in his voice.  
  
"When can you come to Los Angeles?"  
  
"I can be there in two days. I have an appointment there on Wednesday," Cliff
answered.  
  
"Wonderful, I will look forward to seeing you then," Lei Lin concluded.  
  
Cliff hung up the phone and then called his uncle to tell him. Uncle Jack was
thrilled to hear of Cliff's decision and he agreed to meet him in L.A. and
introduce him to Lei Lin. Things were shaping up nicely for Cliff. That
Wednesday Cliff met Jack for lunch and afterward jack took Cliff to meet Lei
Lin and check out the ladyboy. Jack and Lei Lin greeted each other like long
time friends and then Lei Lin shook Cliff's hand. "You will be please with
what I have to show you," he said.  
  
Jack and Cliff went into a room and Lei Lin served them a drink. Jeidee was
called out and Cliff was stunned with the ladyboy's beauty. Jeidee was wearing
a long red silk gown that was slit up the side and showed off ample beautiful
legs. Jeidee turned around several times and then let the dress dropped to the
floor. Jeidee had a beautiful body, great legs, small firm tits, and a
wonderful ass. Jeidee also had the smallest penis that Cliff had ever seen.  
  
"Jeidee would like to be a woman some day. I know someone who can perform that
operation when you are ready. That is if you still want Jeidee," Lei Lin
offered.  
  
"Yes, I do. She, I mean he is beautiful," Cliff replied.  
  
Both Lei Lin and Jack laughed and Lei Lin said, "Jeidee would prefer she and
you should get used to treating Jeidee like a woman."  
  
"Now, because Jeidee is so beautiful and so close to becoming a woman she is
more expensive," Lei Lin stated.  
  
"How much more?" Cliff asked nervously.  
  
"Ten thousand dollars," Lei Lin told him.  
  
"I don't have that much money," Cliff admitted and he was obviously
disappointed.  
  
"I'll give you the extra cash. You just have to promise to bring Jeidee over
to the house once in awhile," Jack offered.  
  
"Really Uncle Jack, that is great. I will definitely bring her to you house,"
Cliff accepted excitedly as he already envisioned the three ladyboys together.  
  
"Wonderful, then we have a deal," Lei Lin announced.  
  
"We have a deal," Cliff confirmed.  
  
Jeidee picked up the dress and left the room to get dressed. Cliff and Jack
concluded the transaction. Jack headed back to his home and Cliff took Jeidee
to his condo. Cliff's life would be very different from that day on and he was
excited about the possibilities. He was anxious to get Jeidee home and fuck
that beautiful ass. Along the way home Cliff learned how skilled Jeidee, now
Jodie was in oral sex.  
  
NEXT CHAPTER  
  
Cliff and Jodie get to know each other intimately. A visit to his uncle's home
proves to be the erotic weekend of Cliff's life.




        His Own Personal Ladyboy Ch. 02


_Author's Note: The story is about transsexuals and all reference to them will
be feminine. That is the ladyboy will be referred to as she or her and not he
or him. _  
  
*  
  
On the drive home Cliff had learned how skilled his ladyboy Jodie was in oral
sex. Now he was anxious to get Jodie in bed and fuck her lovely ass. Cliff
parked in his garage and escorted Jodie into the condo. Jodie was thrilled to
owned by Cliff and she would do everything she could to please him.  
  
"Jodie we will sleep in my bed tonight. I will get you set up in your room
tomorrow," Cliff announced.  
  
Jodie walked into Cliff's bedroom and without waiting to be told took off her
clothes and got in bed. Knowing that Cliff was anxious to fuck her Jodie got
on all fours and displayed her lovely ass to him. Cliff was hard before he
undressed and his stiff cock leaped out as his underwear was removed. He
stared at Jodie's lovely petite body in bed. He thought that he would first
like to massage Jodie and play with her lovely body but he was too anxious to
fuck her. He would have plenty of time to play with Jodie's body as he now
owned the beauty.  
  
Cliff retrieved the lubricant from his night table where he kept it handy. He
knelt behind Jodie and applied the lube generously to her snug aperture. Jodie
cooed with pleasure as first one and then two fingers entered her anus. Cliff
felt the tightness and he knew that he would need plenty of lube. As anxious
as he was to get his cock in that hot looking ass, he enjoyed the anal
foreplay as did Jodie. Cliff took his time fingering and playing with Jodie's
sweet ass and as he did, he wondered if he could ever bring himself to rim her
lovely hole. Cliff had rimmed the two flight attendants he was fucking but
this was different.  
  
Finally Cliff could wait no longer and he eased his cock into the Thai
beauty's ass. The fit was tight and Cliff had to feed his cock to Jodie a
little at a time. Little by little his cock entered Jodie and eventually
filled her rectum taking Jodie's breath away. Cliff stopped moving and allowed
Jodie to adjust to the longest and thickest cock that had ever been in her
ass. Cliff began to move slowly and he watched his cock as it slid in and out
of Jodie's shapely ass. He knew he was not going to last much longer. Jodie's
ass was so beautiful and the sight of his cock going in and out was so erotic.
Besides it was a very tight fit and he was as charged up as ever.  
  
Cliff felt his release build in his scrotum and travel through his shaft. He
stopped moving and leaned over Jodie hugging her as he filled her rectum with
a huge load. Cliff felt Jodie's hand reach between their legs and cup his taut
ball sac as he ejaculated. It seemed as if he had an endless supply of semen
as shot after shot filled Jodie's passage. They both remained still and Cliff
remained hard in her sheath. As he recovered from his massive ejaculation,
Cliff resumed fucking Jodie ever so slowly. He wanted to stay in her ass and
cum as many times as he could until he had nothing left.  
  
Jodie never complained about the pain if she felt any but she did request to
lie on their sides if he was going to keep fucking her. Cliff and Jodie with
incredible flexibility moved to their sides with Cliff's cock still in her
ass. They were on their left sides in a spoon position when Cliff resumed
fucking her. His right hand instinctively cupped Jodie's small breast. He
loved the firmness of her tit and he felt the nipple harden and press into his
palm. Cliff rocked back and forth slowly and he savored every minute he was in
Jodie's super fine ass.  
  
They had not spoken a word since they got in the bedroom and there was really
nothing to be said. They were enjoying each other and Jodie was being the
perfect lover. Cliff lost track of the time but he was sure that they had been
fucking for hours before he came a third and final time that night. He hugged
Jodie to him as he came in her ass a second time. Cliff stayed in Jodie's ass
and continued to fondle the firm little tit as Jodie played with her little
cock. Cliff noticed that Jodie was jerking off using just her thumb and two
fingers. The little erection was cute as it was no bigger than Cliff's pinky
finger. Cliff felt Jodie stiffen as she orgasmed and her sphincter tightened
around Cliff's softening cock.  
  
They remained in the spoon position and Cliff's cock eventually went soft and
slipped from Jodie's ass. A trial of semen followed the cock as if her anus
had been unplugged. Jodie expelled more semen from her rectum and Cliff felt
the wetness. Still they remained in the same position and actually dozed off
together. Cliff loved the feel of Jodie's soft smooth flesh against his own.
Sometime during the early morning hours Cliff got another erection and
subconsciously pushed it back in Jodie's receptive ass. He fucked her slowly
but he didn't cum again. Instead 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 Jodie's buttocks.  
  
DAY TWO WITH HIS NEW TREASURE  
  
The next morning Cliff woke up first and he looked over at his ladyboy. Jodie
was still naked in bed and her curvy ass was on display as she lay on her
stomach. Cliff decided to take a shower so he quietly left the bedroom. Cliff
relaxed under the hot water as he thought of Jodie and how good it was to fuck
her ass. Cliff loved watching his cock slide in and out of the shapely ass.
Cliff convinced himself that it was no different being with a ladyboy then
with a girl when it came to getting a blow job or butt fucking. Cliff felt his
loins stir again just thinking of Jodie's ass. After the soothing shower,
Cliff dried himself off and walked back into the bedroom. To his surprise
Jodie was in bed on all fours with her curvy bubble butt stuck up in the air.
Cliff felt his cock twinge as he looked at Jodie's hot ass. Jodie's body was
delicate, hairless and flawless. Her tiny cock and balls were hidden from
sight and she really did look like a girl in that position.  
  
"Cliff, I would like you to fuck me again," she said in a sultry voice. "You
would like to fuck me again wouldn't you?" she asked teasingly.  
  
Cliff's cock hardened as he approached the bed. He knelt behind Jodie and
began to caress Jodie's beautiful ass. Jodie handed Cliff the lotion and asked
Cliff to get her ass ready. Cliff put an ample amount of lotion in his hands
and rubbed it all around Jodie's bung hole. Then Cliff inserted first one
finger then two fingers preparing Jodie's ass for another ass fuck. Cliff
sawed his fingers in and out of Jodie's anus and Cliff was turned on by the
thought of burying his cock in Jodie's shapely ass again that morning. Cliff
moved closer to Jodie and lined up the head of his cock with Jodie's anal
opening. Cliff eased his big dick into Jodie's ass.  
  
Jodie reminded Cliff, "Go slow and not too deep at first, then deeper."  
  
Cliff spat on his hand and rubbed his saliva all over his cock which made it
very slick when combined with the lotion. Cliff's cock head cleared the
sphincter and he fed it to Jodie a little at a time. Jodie's ass chute was
warm and tight as Cliff went deeper and deeper into her. Soon he was all the
way in Jodie's ass and he started a slow fucking motion. Cliff continued to
pump Jodie's ass with deep, long, deliberate thrusts. Cliff caressed Jodie's
smooth round ass as he fucked it.  
  
Jodie asked Cliff to fuck her harder and quicker. So Cliff picked up the pace
and he pounded Jodie's ass faster and faster. Jodie moaned with each thrust of
Cliff's cock. Cliff could feel his climax building and he knew that any moment
he would shoot his seed in Jodie's ass. Cliff tried to make it last as long as
possible but once Jodie contracted her anal muscles Cliff lost it.  
  
Cliff fired a barrage of cum in Jodie's ass filling it to overflowing. Cliff
couldn't remember when he came so much. As Cliff continued to fuck, his cum
backed up in Jodie's rectum and oozed out. Jodie used her talented sphincter
muscle to milk Cliff's cock and drained it dry. Jodie's milking action
weakened Cliff and sent tingles through his body. Cliff pulled out of Jodie
and collapsed on the bed next to her.  
  
Jodie rolled over on her back and jerked off once again. Cliff watched as
Jodie stroked her tiny erect cock with her two fingers and thumb. Jodie
ejaculated and the semen landed on her abs and pooled around her pubes. Cliff
reached over and tweaked Jodie's rock hard nipples.  
  
"Jodie let's get up now and get cleaned up. I have many things to show you
today and we are also going shopping," Cliff stated.  
  
They showered separately as Cliff did not want to prolong the morning sex. He
knew if he was in the shower with Jodie that he would fuck her again. After
showering and dressing, Cliff made breakfast and showed Jodie where everything
was kept in the kitchen. Cliff then stripped his bed of the cum-stained sheets
and put them in the washer. Cliff taught Jodie how to use the washer and
dryer. After getting Jodie set up in what would be her room they had lunch and
then went shopping to get clothes for her.  
  
Cliff took Jodie to the shopping mall and they spent all afternoon picking out
clothes, lingerie and bathing suits. Jodie was thrilled with all of the nice
things that Cliff had bought for her. Jodie was also excited about going to
the beach in her new bikini. By the time they got back to the condo Jodie was
ready to be fucked and Cliff was more than ready. As soon as they were inside
and had put the clothes in Jodie's room they sprung into action. Jodie dropped
to her knees to undress Cliff.  
  
Jodie undressed Cliff ever so slowly and by the time his underwear was peeled
down his legs, Cliff was rock hard. Jodie stared at the 8" cock in front of
her and then lowered her mouth onto the shaft and began to slowly sucked
Cliff's dick. As Jodie sucked Cliff's cock, she was anxious to feel it in her
ass again. Cliff was incredibly turned on and without warning he ejaculated
into Jodie's mouth. Jodie was caught off guard this time by the volume and
force of Cliff's ejaculation but she recovered quickly and managed to swallow
Cliff's entire load.  
  
Jodie stood up and patted Cliff gently on his balls. Jodie licked her lips and
then said, "Now I want you to fuck me."  
  
Jodie got the lubricant and applied it to Cliff's cock. Cliff stayed hard the
entire time as Jodie stroked the impressive shaft. "I like playing with your
cock but I need you to fuck me now," Jodie cooed.  
  
Then Jodie got on the bed on all fours and handed the lube to Cliff. "Get my
ass ready for your big cock," Jodie whispered.  
  
Cliff took the lube and squirted a gob right on Jodie's anus and then pushed
it in. Cliff worked first one finger and then a second In Jodie's asshole.
Jodie put her head down on the bed and arched her back further emphasizing the
shape of her curvy ass. Cliff was still amazed how much Jodie resembled a girl
and it served to turn him on even more. Cliff caressed Jodie's lovely ass as
he lubricated her asshole. Cliff then left his fingers drift over Jodie's
scrotum and tickled the firm flesh of her perineum. Jodie's little cock
twitched when Cliff's finger ran over the perineum and again when Cliff
caressed the tight ball sac. Satisfied that Jodie's ass was slick, Cliff knelt
behind her and eased his cock into Jodie's ass.  
  
Jodie placed his hand on Cliff thigh as if to guide the penetration. "Nice and
slow," Jodie gasped as her ass was spread wide again.  
  
"God you are really tight," Cliff echoed.  
  
Cliff took his time slowly feeding his cock into Jodie's ass and then
withdrawing it slightly. Each time Cliff would go a little deeper and then
stop to allow Jodie to adjust. Then Jodie felt Cliff's pubic hairs tickle her
buttocks and she knew that Cliff was buried to the hilt. Cliff began a slow
methodical fucking of Jodie's ass and he relished every second he was in the
beautiful derriere. Cliff reached around Jodie as he leaned over and his hands
brushed against Jodie's small firm tits. Cliff had momentarily forgotten that
Jodie had tits but now he held the cute tits and caressed them teasing the
nipples as well. Once again Cliff truly felt like he was fucking a girl in the
ass.  
  
Cliff that felt that familiar twinge and he pushed his cock all the way into
Jodie's ass and held it there as he fired a barrage of cum into Jodie's
rectum. "Oh I feel it, I feel it!" Jodie exclaimed as round after round was
released from Cliff's cock.  
  
Cliff placed his hands on the smooth curvy ass cheeks and caressed them as he
filled her ass with his seed. Cliff stayed hard and continued to fuck Jodie
slowly until Jodie begged him to move to their sides as they had done before.
Keeping his cock deep in Jodie's ass Cliff guided them on their sides and then
he resumed fucking Jodie. Cliff had his left arm wrapped around Jodie's waist
and he was holding a firm tit in his left hand. Cliff right hand
subconsciously sought out Jodie's stiff 2" cock and played with it as he
fucked her. "Oh that's it play with my clit," Jodie moaned.  
  
Jodie came twice before Cliff came a third time. Cliff felt Jodie's cum travel
through the tiny cock and dribble onto the bed sheets. Cliff then placed both
hands on Jodie's tits and held them firmly as he drilled Jodie's ass until he
came again. The two of them then lay in bed perspiring and breathing hard from
their sexual marathon.  
  
"Come with me and I will wash your body," Cliff whispered.  
  
Cliff took Jodie into the shower with him. Cliff could not keep his hands off
of Jodie's shapely body and he loved washing Jodie's tits and ass. Cliff got
hard again and he had to fuck Jodie one more time. He slipped his soapy cock
into Jodie's ass again and they fucked until Cliff ejaculated one more time.
Then they finished their shower and went back to bed but this time to their
own rooms as they were finished having sex. Cliff needed to get a good night's
sleep and it was the perfect time to let Jodie sleep in her own bed.  
  
SETTLING IN  
  
On Monday morning Cliff went to Jodie's room and fucked her before the day
started. After the sex, they showered, dressed and ate breakfast. Jodie
cleaned up afterward and Cliff went into his office at home to begin his work
day. Jodie went about the chores that Cliff had listed for her as he conducted
business in the privacy of his office. Several hours passed and Cliff decided
to take a break. He went out into the kitchen to get a cup of coffee.  
  
Jodie was working at the kitchen sink and she was wearing one of the matching
jockey bra and sleep shorts that Cliff had bought for her. He watched her work
for several minutes and his cock got hard from watching her ass in the tight
shorts. Cliff freed his cock from his pants and walked up behind Jodie. He put
his arms around her and kissed her on the neck. It was the first time that he
had ever kissed a ladyboy anywhere. He let his hands slip down into the jockey
shorts and cup her lovely buttocks. Jodie moaned softly and wiggled her ass in
response.  
  
Cliff lowered the shorts to just below Jodie's buttocks with the shorts still
covering her little dick. Seeing some butter on the kitchen counter he scooped
up some in his fingers and used to lubricate Jodie's asshole. Once he was
satisfied that Jodie was well greased he eased his cock into her ass. Jodie
leaned over the sink and arched her back, further emphasizing the shape of her
curvy ass. Cliff caressed her lovely bottom as he fucked her slowly. Jodie was
overcome with the lust of the moment.  
  
Cliff feeling his imminent ejaculation leaned into Jodie and wrapped his arms
around her. He pushed up the bra and cupped her small tits and felt the hard
nipples in the palms of his hands. At that moment Cliff felt that life didn't
get any better. His body stiffened and he shot a good size load into Jodie's
rectum. Jodie as always used her sphincter to milk Cliff's cock and squeeze
the seed from it. Cliff eased his cock out and wiped it clean with a paper
towel. Then he used another paper towel to wipe the semen from Jodie's asshole
as it oozed out. Jodie giggled and held the paper towel against her anus as
she headed for the bathroom.  
  
Cliff made a cup of coffee and sat at the kitchen table. Jodie returned with a
smile on her face and said, "That was very exciting. I liked that."  
  
"I did too. We will have to have more spontaneous sex like that," Cliff agreed
and added, "It was the first time that I have ever taken a sex break during
the business day."  
  
Jodie returned to her chores and Cliff took his coffee back to his office.
They both kept working until lunch time and Jodie prepared lunch for both of
them. Jodie told Cliff that lunch was ready so as soon as he wrapped up his
phone call, he joined her. After lunch Cliff went back to work and Jodie did
the dishes and straightened up the kitchen. There wasn't any more sex between
them that day until after dinner. Jodie made dinner, served Cliff and cleaned
up afterward as Cliff enjoyed an after dinner drink on the condo outside deck.
It was a pleasant evening and as Cliff sipped his drink he thought about how
good things were with Jodie around.  
  
Jodie came out on the deck and asked, "Can I get you anything else?"  
  
"Sure, freshen my drink and then join me out here," Cliff requested.  
  
Jodie freshened up Cliff's drink and then joined him on the deck. She brought
out a cup of tea for herself. Jodie had changed into one of the new lounge
outfits that Cliff had bought for her. It was a jade green velour outfit that
clung to her every curve. Cliff liked the look and it had an effect on him
when he watched her ass undulate under the fabric. Jodie finished her tea and
Cliff told her to stand by him. He ran his hands over the soft material and he
liked the feel of it. He caressed Jodie's ass and it turned him on again.
Cliff decided that it was time to fuck Jodie again.  
  
They went to Jodie's room and got in her bed. Once again Cliff prepared
Jodie's ass for his cock and fucked her doggy style. Jodie, as she had done
before, reached between their legs and fondled Cliff's testicles as he fucked
her. After Cliff ejaculated in her ass they rolled to their sides and Cliff
kept fucking her. His left arm was under her body with his hand on her firm
breast while his right hand rubbed her tiny cock. This was Jodie's favorite
position and she was pleased that Cliff would play with her cock until she
came. Jodie knew that Cliff would never suck her little cock but she was glad
that he would touch it. Jodie came several times before Cliff was done fucking
her and each time Cliff would rub the semen into her skin. When Cliff was
finished he returned to his own bed to get a good night's sleep.  
  
The rest of the week followed a similar pattern each day. Cliff would fuck
Jodie in the morning in Jodie's bed or in the shower. They would have either
oral or anal sex during the day when Cliff took a break from work. In the
evening Cliff always fucked Jodie in her bed before retiring to his own room.
Jodie took care of all the chores and preparing all the meals. She catered to
Cliff's every need and she behaved liked a loyal servant. Jodie liked Cliff as
he proved to be a caring master.  
  
That Friday Cliff took Jodie to the beach. The beach was always a zoo on
Saturdays and Sundays so Cliff usually went on Fridays as long as he didn't
have a work commitment. He would always catch up with his administrative items
on Saturday and Sunday mornings. Jodie was thrilled that she was going to the
beach. Cliff picked out the bikini for her to wear and what shorts and top to
wear over it. Cliff packed the beach bag since it was Jodie's first time but
she paid close attention to what he packed.  
  
They arrived at the beach about 10:00 AM and found a good spot to set up their
towels and beach chairs. The beach wasn't crowded but it would be by 2:00 PM
as people would start arriving around noon. Cliff put sun block on Jodie's
back and shoulders and had her do the same for him. At first they laid on
their stomachs soaking up the rays. They would take dips in the ocean whenever
their bodies got too hot. Each time they walked to and from the water heads
turned to take in Jodie's petite beautiful body. Cliff smiled to himself and
thought, "If they only knew what was in those bikini bottoms."  

There were plenty of good looking and shapely women on the beach but there was
something about the Thai beauty that was intriguing. They had packed
sandwiches and water for lunch and after lunch Cliff set up the beach chairs.
They covered the front of their bodies with sun block and sat in the chairs
facing the ocean. Cliff loved the beach and he enjoyed the people watching.
They stayed at the beach until about 3:00 PM and then headed home. Jodie had
enjoyed the day immensely and looked forward to more beach days.  
  
When they arrived home they stripped naked and headed for the bathroom. Cliff
decided to take a bath instead of a shower. He told Jodie that he would wash
her body first and then she could do him. He had a brief flashback to the
weekend at his uncle's house when he was washed by Mali and Kulap. Once the
tub was filled Jodie sank her lovely body into the warm water. Cliff used a
bath sponge to wash off the lotion and he used his bare hands when he washed
her tits.  
  
Cliff then had Jodie lie face down in the tub so he could wash her super fine
ass. He ran the sponge all over her body first and then he played with her
buttocks. Jodie began to move her bottom up and down in a very sensual manner
and Cliff responded. He caressed her ass each time the buttocks broke the
surface of the water. He loved watching her sweet bubble butt move up and down
as it glistened with its wetness. He began to finger her anus and finally he
could take no more. He had to fuck her.  
  
Cliff got in the tub with Jodie, soaped up his rock hard cock and eased it
into her hot ass. They fucked slowly so as not to splash too much water but
Cliff was so turned on that he came very quickly. He was not interested in
prolonging his ejaculation this time but instead of cumming in her ass he
pulled out and shot his load on her buttocks. Cliff stroked his cock and aimed
his release at Jodie's anus and buttocks. It was one of the most erotic sights
he ever witnessed as he seed splashed against her anus and trickled down
between the buttocks. Cliff then pushed his cock back in Jodie's ass and let
her massage it with her sphincter.  
  
Cliff stayed hard but he decided to take Jodie to bed instead of fucking her
again in the tub. They got out and dried their bodies. Cliff then followed
Jodie to her room where she got in bed on all fours. Cliff was still hard when
he joined her in the bed and after lubing her ass he fucked her hard and fast.
Cliff was incredibly turned on that day and it showed. After he came in her
ass this time he pulled out and flopped down on her bed. Jodie rolled over and
jerked off and orgasmed quickly. They rested a short time and then Cliff
showered by himself.  
  
Minutes later they were both wearing short terry robes and Jodie looked
alluring in hers with her shapely legs on display. Her bottom was outlined by
the robe clinging to her. Jodie made dinner and afterward cleaned up the
kitchen while Cliff nursed his drink. They sat on the deck together in their
robes, Cliff with his drink and Jodie with his tea. Jodie cuddled up to Cliff
who put his arm around her. He stroked her silky black hair and sneaked his
hand in her robe to find her breast. He loved the way her nipples hardened in
the palm of his hand. Jodie slipped her hand into Cliff's robe and located his
cock. It was in a soft state but not for long as Jodie stroked it lovingly.
They remained on the deck fondling each other in foreplay for several minutes
before Cliff took Jodie inside and fucked her again.  
  
Jodie requested the spoon position on their sides and Cliff agreed. He
actually liked this position when he was a little tired. He fondled Jodie's
breasts and little dick as he fucked her ever so slowly. Cliff liked having
his hard cock in her ass and he was in no hurry to cum this time. They fucked
for over an hour with Jodie cumming several times before Cliff's final
ejaculation. That night Cliff stayed in Jodie's bed.  
  
A VISIT TO UNCLE JACK'S  
  
On Saturday morning Cliff eased his body out of Jodie's bed. He looked back at
the Thai beauty that was still in a deep sleep. He decided to let her sleep
and he quietly left the room. He had some work to do so he made coffee and
worked in his office. It was nearly 11:00 AM when Jodie woke up. Jodie
apologized for sleeping so late and that she was not up to get Cliff his
coffee and breakfast. Cliff smiled and told her, "It's not a problem. I had
things to do and I still know how to make the coffee."  
  
"Can we go to the beach again today?" Jodie asked.  
  
"No, the beach is really crowded on Saturday and Sunday. I never go on those
days."  
  
"Can we go to the pool then?" Jodie asked obviously wanting to be by water
that day.  
  
"Not today," Cliff replied as he was not yet ready to expose Jodie to the
other condo owners. Then he thought of an idea and proposed it to Jodie.
"Obviously you want to be in your bikini by the water again. I will call my
uncle and see if we can go there and sit by his pool. Do you remember my Uncle
Jack?"  
  
"Yes, he is the one who has two Kathoeys."  
  
"Right, they are Mali and Kulap."  
  
"If we go there will I be able to have sex with Mali and Kulap?" Jodie asked
shyly.  
  
"Yes, in fact I'm sure that it will be expected."  
  
Cliff then called his Uncle Jack who was glad to hear from him. Jack was
thrilled that Cliff wanted to visit him and he was looking forward to seeing
Jodie. Cliff thanked him and told him they would be there in a couple of
hours. "Plan to stay overnight," Jack told him.  
  
Cliff told Jodie it was a go and they got ready to visit his uncle. Jodie was
excited about meeting Mali and Kulap and the possibility of having sex with
them. It had been so long since anyone had sucked Jodie's cock and she was
already hard with anticipation. The drive seemed to take forever but when they
arrived Jodie was overwhelmed with Jack's home. Cliff parked the car and they
went up to the front door. Cliff rang the bell and within seconds they were
greeted by Mali at the door.  
  
"Please come in, master is excited that you are here. This must be Jodie,"
Mali held out her hand and said, "I am Mali."  
  
Jodie shook the beautiful ladyboy's hand and replied, "So very nice to finally
meet you."  
  
The two ladyboys stared at each other in admiration of each other's beauty.
Then Mali took Jodie by the hand and said, "Come I will introduce you to my
master and Kulap."  
  
Cliff already had an erection just from watching the two ladyboys and
anticipating what the next two days would bring. He followed Mali and Jodie
into the gathering room where Jack and Kulap were seated. Jack smiled and
stood up when he saw them, "Cliff my boy, how the hell have you been? Getting
laid much?" Jack ribbed him.  
  
"Yeah a little," Cliff jabbed back.  
  
The two men hugged and then Jack looked at Jodie and held out his hand. "It's
good to see you. You're looking well."  
  
"Thank you! Cliff takes good care of me," Jodie replied.  
  
"I bet he does," Jack said with a sinister chuckle.  
  
Mali and Kulap giggled and covered their mouths with their delicate hands.
"Hey let's go out to the pool. That's why you're here. The girls will get
drinks for us," Jack announced and then added, "Cliff you can leave your
clothes in here."  
  
Cliff and jack took off their clothes and handed them to Kulap whose eyes
traveled to Cliff's impressive cock. Mali also gazed at the meat that had
previously been in all her holes. Jodie blushed since it was the first time
she had seen Cliff naked in front of other people.  
  
"Yeah they missed your cock and they have been looking forward to your
return," Jack said and then he turned to leave the room.  
  
Cliff followed his naked uncle out to the pool and they sat side by side in
lounges. "So how is it going with your ladyboy? Is it what you expected?" Jack
inquired.  
  
"It has exceeded my expectations. The sex has been great and Jodie has already
taken over all of the household duties," Cliff reported.  
  
"That's great! So do you miss pussy?" Jack asked.  
  
"I haven't thought much about it but when and if I do I know where to get it,"
Cliff replied with a chuckle.  
  
"I bet you do. A little word of advice, remember that Jodie is a servant. You
have to continue to treat your ladyboy as a servant or Jodie will lose respect
for you. Remain in control at all times and remember this is a better life
than they would have anywhere else," Jack offered.  
  
"I'll remember that," Cliff agreed.  
  
Just then they three ladyboys arrived with the drinks. They were all naked and
Jodie was blushing. They set the drinks down and took their seats in other
lounges. "Thank you girls, now if you want to play, go right ahead. Cliff and
I could use a little entertainment," Jack announced.  
  
Mali and Kulap stood up and Cliff admired their beauty all over again. They
put lounge cushions on the pool deck and guided Jodie to a kneeling position.
Mali knelt in front of Jodi's face and offered her cock to Jodie's mouth.
Kulap got behind Jodie and pushed a well lubed dick into Jodie's ass. In
didn't take long for Mali and Kulap to cum as they had been horny all day
thinking about the sex. They were glad to have someone to fuck and suck their
dicks.  
  
Jodie was dying to cum so Kulap sick Jodie's cock as Mali pushed her cock into
Jodie's ass. Jodie ejaculated within minutes of Kulap's cock sucking as she
too was very turned on. Kulap then moved behind Mali to fuck her. Cliff and
Jack watched the exotic beauties fuck and suck each other. They were in no
hurry to join the three Thai beauties as they had all night. Jodie with her
tiny dick even got to fuck both Mali and Kulap. Jodie was ecstatic that she
got to fuck the other ladyboys.  
  
Mali, Kulap and Jodie had cum multiple times enjoying each other. Now they
would only pleasure their two masters for the remainder of the day. Jodie lay
on her back with a glow on her face as she had just had incredible sex. Mali
and Kulap lay on either side of Jodie and caressed her firm tits. Jodie's tits
were slightly bigger than those of Mali and Kulap. Cliff was stroking his hard
cock when his uncle spoke.  
  
"Cliff, I want to see you fuck Jodie," Jack told him.  
  
Cliff was surprised as he expected his uncle to want to fuck Jodie first.
Cliff moved his body to the cushions where the three ladyboys were stretched
out. Mali and Kulap smiled and they took a hold of Cliff's cock. Passing it
back and forth they both sucked on it until Mali guided it into Jodie's ass.
Jodie raised her legs providing easier access and Mali pushed the cock into
her. It was the first time that Cliff had ever fucked Jodie in the missionary
position. Mali and Kulap returned to sucking Jodie's tits as she was fucked by
Cliff.  
  
Jack then joined the foursome and began to fuck Mali from behind. Jodie turned
her head when she saw that Kulap had another erection and she took Kulap's
cock in her mouth. Kulap's cock was maybe an inch bigger than Jodie's but not
much more. Cliff was in another world with the eroticism of the orgy. He
fucked his Thai ladyboy with slow steady strokes allowing his cock to nearly
come out of Jodie's ass before pushing it all the way back in. He was so
involved in the activities around him that his release snuck up on him.  
  
Cliff closed his eyes as he prepared to ejaculate into Jodie's rectum. Sensing
that he was close to cumming Mali pulled Cliff's cock out and jerked him off.
The force and volume of Cliff's ejaculation was amazing as he fired at least
seven ropes of semen in the air. Jodie was cum-covered and both Mali and Kulap
had some in the hair and on their faces. Jodie had his seed from her head to
her pubes. Mali and Kulap then began to lick the milky substance from Jodie's
body.  
  
Jack was stunned and impressed, "Geez, did you see that? It was like a fucking
volcano."  
  
Jack continued to fuck Mali as she licked Jodie's body until he too came. Jack
also pulled out and shot a single stream on Mali's shapely ass. "Christ, I
need a drink after that," Jack announced.  
  
Jack and Cliff returned to their lounges leaving the ladyboys to clean
themselves up. "This has to be the hottest thing that I have ever done in my
life," Cliff sighed.  
  
"Yeah, its fun though, isn't it?" Jack remarked and the said, "Let's take it
easy the rest of the afternoon. We'll have some more fun after dinner."  
  
Cliff nodded and took a sip of his drink. He watched as the three ladyboy
beauties entered the pool and waded in the water. He wondered what the evening
would bring and what the sleeping arrangements would be. He still expected his
uncle to fuck Jodie but he wasn't sure when that would happen. Cliff also knew
that Mali and Kulap were both anxious to feel his big dock in their asses
again. He had been great afternoon and it was shaping up to be a wild rest of
the weekend.  
  
_NEXT CHAPTER  
  
The wild erotic weekend continues at Uncle Jack's place. Cliff then learns
that he will be out of town for a week and he has to decide what to do with
Jodie. Cliff's business trip proves to be very provocative._




        His Own Personal Ladyboy Ch. 03


_AUTHORS NOTE: This is the final submission for this story. I have received
requests from readers to write final chapters to some of the stories and I
will focus on doing just that._  
  
*****  
  
A SHOCKER  
  
Cliff was seated across from his Uncle Jack's attorney. "I can't believe this
happened. Uncle Jack was never sick a day in his life."  
  
"It caught us all by surprise Cliff. However you uncle was always a man who
planned ahead and his Estate Plan is an example of that."  
  
"Was there anything that triggered this or caused it, a previous injury?"  
  
"No, a brain aneurysm is impossible to detect. At least it was over quickly
and he didn't suffer."  
  
"I still can't believe it. I was just at his home last weekend."  
  
"Well it's your home now; he left everything to you including possession of
Mali and Kulap. I'll arrange for all the title transfers to your name. You can
move into the house anytime you want to. If you wish I can be your attorney
going forward."  
  
"Yes, I would like that. You've been a great help. Thank you!"  
  
Cliff shook hands with the attorney and left his office. He had many things to
settle up over the next several weeks. He would sell his condo and his car as
he would not need them going forward. He didn't need all his furnishings
either, so he would sell or donate them as well. Jodie was back at the condo
getting it cleaned and presentable. He would pick her up and bring her to the
house to keep Mali and Kulap company.  
  
He thought about the two beauties that had served his uncle so well and now
they would be his. He would have three very pretty ladyboys to take care of
the house and him. Cliff always enjoyed being with Mali and Kulap and he loved
having sex with them. He decided to swing by the house and check on them
before he returned to the condo. He decided that he would bring Jodie over to
the house tomorrow.  
  
SETTLING IN  
  
Cliff moved into his former uncle's house which was now his home. He moved his
office into what used to be his uncle's office. Jodie was setup in one of the
spare bedrooms. Cliff's condo had sold quickly as it was in a desirable
location. He was able to sell his car which he didn't need since taking title
to his uncle's luxury car. Cliff used a reseller to dispose of his furnishings
and personal property that he no longer needed. In a week's time he was
settled in and working out of his new home.  
  
It was an adjustment having the three beautiful lady boys as servants but he
quickly adapted to the situation. Each night he would take a different one to
bed with him. Some days they would have group sex by the pool or in the
Jacuzzi. All three lady boys loved his impressive cock and they enjoyed sex
with each other. Mali and Kulap were initially sad over the loss of their
Master Jack but that soon passed. Now they were thrilled that they had a new
Master Cliff and he was such a good lover. They were also pleased that Jodie
was now living with them.  
  
It was beautiful weather wise one Saturday and Cliff decided to spend the day
by the pool. It started with breakfast poolside. The four of them wore skimpy
swimwear. Cliff wore a snug bikini Speedo that showed off his impressive
package. Mali wore a shocking pink string bikini. Kulap and Jodie also wore
string bikinis, jade green and white respectively. The bikinis had thong
bottoms and their cute asses were prominently displayed.  
  
It didn't take long before Cliff had a raging hard-on from watching the lithe
brown bodies move around the pool deck. Mali spotted Cliff's condition first
and she went over to his lounge. Mali rubbed Cliff's erection through his
Speedo with her petite hand. She leaned over and mouthed the length of the
shaft driving Cliff mad with desire. Kulap and Jodie then joined Mali and the
three of them played with Cliff's impressive cock before finally releasing it
from the confines of his swimsuit.  
  
The huge stiff dick stood proudly away from Cliff's pubes and three delicate
hands stroked it lovingly. Mali and Kulap were on either side of Cliff
mouthing the length of his shaft. As they did their lips joined in a kiss.
Jodie knelt in front of his master and took the large mushroom head in her
mouth. It was the first time ever that Cliff had three mouths on his cock at
the same time. The feeling of it and the sight of it was incredibly erotic.  
  
The three of them stayed glued to his cock until he announced that he was
cumming. Jodie took the first stream in her mouth and quickly passed the
spurting rod to Mali. She took the second stream of his discharge and then
passed the cock along to Kulap who received the third jet in her mouth. The
three ladyboys continued sucking and passing the cock around until it was
drained of Cliff's seed.  
  
"That was absolutely incredible, the most erotic thing I have ever
experienced," Cliff sighed as he reclined in the lounge. "Have some fun now,
while I recover."  
  
The three Thai beauties slipped off their bikinis and their delicate naked
bodies came together. They spread out lounge cushions on the pool deck and
began their three way sexual performance. Kulap got on her back and Jodie got
between her legs and eased her cock into the receptive ass. Mali straddled
Kulap's face and Jodie took Mali's cock in her mouth. Kulap caressed Mali's
buttocks and rimmed her nether hole. Cliff stroked his cock and watched the
threesome for as long as he could. It didn't take long before he was ready to
fuck Jodie.  
  
Cliff moved off the lounge and lubed his cock with lotion and saliva. Kneeling
behind Jodie he steadily pushed his big dick into her tight cute bottom. Jodie
stopped moving and stopped sucking until Cliff began to fuck her. Jodie loved
what was happening to her. She loved fucking Kulap while she had a cock in her
mouth and a big one in her ass. Jodie was very turned on and her body took
over for her. Jodie was rapidly fucking Kulap and in the process she was
thrusting back on Cliff's cock. Cliff did not have to move as Jodie's actions
did all the work.  
  
Jodie was the first to cum and she shot her load into Kulap's rectum. Jodie
stopped moving as she ejaculated so Cliff picked up the pace again and reamed
her lovely bottom. Mali wanted to fuck Kulap next so she changed positions
with Jodie. Now Mali was getting fucked by Cliff as she fucked Kulap and
sucked on Jodie's cock. It didn't take long for Mali to cum and she added her
load to Jodie's in Kulap's rectum. Cliff felt Mali's sphincter tighten around
his shaft with each pulsating cum shot.  
  
It was Kulap's turn to get fucked by Cliff so Jodie got on her back and
welcomed Kulap's cock into her ass. Mali fed her cock to Kulap's mouth just as
she was getting Cliff's cock in her ass. It was a repeat performance except
this time Cliff ejaculated flooding Kulap's anal passage and Mali came in
Kulap's mouth. Kulap filled Jodie's ass with a substantial load and at the
same time received Mali's discharge in her mouth.  
  
The four of them cooled off in the pool and rinsed the semen from their
bodies. The rest of that morning they remained naked and took in the sun's
rays as they relaxed and recovered from the orgy. Cliff looked over the three
lady boys and he was pleased with their appearance. They all had lovely petite
bodies with sweet asses and cute titties. Even their little cocks looked cute
on their shapely bodies. They wouldn't have sex again until after lunch and it
would be in the house as it had gotten too hot by the pool.  
  
Following lunch they went to the lower level for massages. Cliff was first to
receive his massage and he loved the three sets of hands touching his muscular
body. After his massage he insisted on massaging each of the ladyboys one at a
time. He loved fondling their pert breasts and tweaking their stiff nipples.
Most of all he loved massaging their alluring bottoms and fingering their
nether holes. By the time the massages were completed they were all ready for
more sex.  
  
Jodie wanted to take Mali's and Kulap's cocks in her ass at the same time.
Since Jodie handled Cliff's thick dick with ease she knew she could take the
two smaller cocks together. Kulap lay on her back and Jodie lowered her ass
onto Kulap's cock. Mali then got behind Jodie and eased her cock in along side
of Kulap's. The feeling was incredible for all three of them. Mali and Kulap
began to move in Jodie's ass. Cliff was so excited by the scene he had to join
them.  
  
Cliff presented his cock for Jodie to suck as she was getting fucked. Kulap
reached up and played with Jodie's cute titties as she handled the three cocks
in her body. Mali reached around and stroked Jodie's cock and the four of them
raced toward another orgasm. Kulap came first and Mali felt the warm semen on
her cock as she continued to fuck Jodie. Cliff came next filling Jodie's mouth
and then Jodie shot her load onto Kulap's belly. Mali was the last to cum
adding her load to Kulap's in Jodie's rectum.  
  
The four of them remained motionless for several minutes and then one by one
they separated. They entered the wading pool and the three ladyboys bathed
each other cleansing their bodies of semen. Mali and Kulap said that they
would like to try two cocks as Jodie had done. They agreed that it would have
to wait for another day as they were all sexually sated and drained. The four
of them donned silk bathrobes and returned to the main level. Cliff sat in the
family room and Mali brought him a drink. He relaxed as the lady boys got
dressed and then made dinner. Mali checked on him often and refreshed his
drink as needed.  
  
LIFE IS GOOD  
  
It was over a month since Cliff moved into the house he inherited from his
uncle Jack. He was very comfortable with his new life and the sex with the
ladyboys was fantastic. Cliff had not dated in quite sometime and he really
didn't need to and he didn't miss it. At first he thought that he might miss
the company of a woman in bed but that never happened. He was content with the
ladyboys for now and he had no plans to change it.  
  
During the week one of the ladyboys; Mali, Kulap or Jodie would spend the
night in Cliff's bed. Each night would start out with foreplay and oral sex.
The ladyboy would stroke and play with Cliff's impressive cock in a manner of
worshipping it. Eventually Cliff couldn't hold back any longer and he would
cum in a receptive mouth. The ladyboy would swallow every drop of his seed and
continue to suck his shaft keeping him hard.  
  
When Cliff was ready he would position the ladyboy on all fours and fuck her
in the ass. He loved watching his cock slide in and out of the cute shapely
bottom. He would caress the smooth flawless buttocks as he fucked the ladyboy
slowly. It always took him longer to cum the second time but that was the plan
as he wanted to stay in the lovely ass for as long as possible. Sometimes it
took an hour for Cliff to cum again but when he did he filled the rectum with
a substantial load. He would stay in the beautiful bottom until his cock
softened and slipped out. A trail of his seed would follow and run between the
buttocks and over the tiny testicles.  
  
The ladyboy would remain in Cliff's bed and they would cuddle up in the spoon
position. Cliff's cock would be nestled in the buttocks and his hands would
fondle the cute pert titties. They would fall asleep in that position and most
times wake up in the same position. In the morning Cliff would fuck the
ladyboy in the spoon position until he ejaculated into the snug rectum. They
would both be on their sides with Cliff's cock buried deep in her ass. One arm
would be under her with his hand on a breast while the other hand played with
the tiny cock. Cliff had become accustomed to giving the ladyboys a reach
around and jerking off their small cocks as he fucked them.  
  
Saturdays and Sundays were reserved for group sex and impromptu sex. Sometimes
Cliff would watch one of the cute asses in silk pajamas and he just had to
have it at that instant. One morning he walked in the kitchen and saw Mali
making coffee. She had her back to him and he studied the movements of her
buttocks under the pajamas and he got an erection. Cliff walked up behind Mali
and wrapped his arms around her pressing his cock into her bottom.  
  
Cliff lowered his sleep shorts and pulled Mali's pajama bottoms down just
below her buttocks. She looked so sexy with just her bottom showing. He
greased up his cock with butter that was on the counter and eased it into her
snug receptive ass. Cliff fucked her slowly and moved his hands under the
pajama top to cup her naked breasts. He was very turned on by the eroticism of
the moment that he ejaculated quickly and flooded Mali's rectum.  
  
He remained in Mali's ass until she had drained his cock using her talented
sphincter muscle. Cliff stepped back and took some paper towels from the
holder and handed them to Mali. She giggled as she covered her bottom and
shuffled off to the bathroom. Cliff wiped his cock clean and pulled up his
sleep shorts. Next he poured a cup of coffee and went out into the sun room
where the morning paper was waiting on his chair. He sipped his coffee and
read the paper while breakfast was being prepared. He didn't have any plans
for the weekend and he liked it that way.  
  
Cliff decided that after breakfast he would workout for awhile and swim laps
in the pool. Later he would have sex with the ladyboys but he wasn't sure
where that would happen. It could be by the swimming pool, in the Jacuzzi, in
the massage room or bathing pool. Wherever it took place it would include all
three ladyboys and it would be great sex as always.  
  
GETTING CREATIVE  
  
One day Cliff was walking back to his car after a meeting with a client. The
client office was adjacent to Chinatown and Cliff spotted a group of
schoolgirls in uniform. He studied the Chinese girls in their school uniforms
with the short skirts cut above their knees. Some skirts were shorter than
others and exposed more skin above the white knee high socks. Cliff found the
schoolgirls to be very alluring and that's when he got the idea to have his
ladyboys dress up in similar school uniforms. That evening he told his
ladyboys what he had in mind and they loved the idea of playing dress up.
Cliff went on-line, located a supplier and ordered three schoolgirl uniforms.  
  
A week later the uniforms arrived and everyone was excited. The ladyboys
hemmed the uniform skirts so that they were very short just covering their
lovely bottoms. The effect was seductive as when they bent over from the waist
Cliff could see the lower part of their buttocks in the cotton panties.
Following breakfast on Saturday morning Cliff had them dress in their school
girl uniforms. Kulap suggested that they fix their hair in pigtails and Cliff
nearly creamed his drawers when he saw them.  
  
They played a game whereby they imagined that the schoolgirls were taking a
sex education course and Cliff was the instructor. First he would teach them
about oral sex and he had each of them take turns playing with his cock and
then sucking it. Mali went first and she knelt in front of Cliff and lowered
the zipper on his trousers. She fished the big cock out through his fly and
stroked it for a few minutes in her petite hand. Mali acted as it was the
first time she had ever seen a cock.  
  
Cliff was turned on by her appearance but even more so by her play acting.
Mali handled the stiff penis as if she was inspecting it and learning about
it. She teased the pee slit with her tongue and took just the soft mushroom
head in her mouth. She giggled as she role-played that of a virgin schoolgirl.
Mali got more daring with the big dick and sucked on it taking more if it in
her mouth. She called out to her fake classmates to come over and take a look
at the ominous looking cock.  
  
Giggling Kulap and Jodie knelt along side of Mali to get a look at the male
organ. They too acted as if it was their first time and emulated the actions
of Mali. The three ladyboys were really into the role-playing now and they
passed Cliff's cock back and forth between them. They took turns sucking it
and stroking it and fondling his testicles. Cliff looked at their angelic
faces as they worked him over and he knew that he would cum at any moment.  
  
Mali sensed he was close so she took his cock in her mouth and sucked on it
until he ejaculated. As soon as the first stream entered her mouth she passed
the cock onto Kulap to receive the next burst of semen. Kulap then passed it
onto Jodie who welcomed another jet in her mouth. The cock went back to Kulap
and then back to Mali who sucked it dry. The three ladyboys had not let a drop
of Cliff's seed escape their mouths. Cliff looked at them still clothed in the
school uniforms with their hair in pigtails appearing so innocent.  
  
Cliff rested and instructed the ladyboys to act as if two of them were
seducing the other one. He would pretend as if he caught them in the act and
decided what to do when he was ready. They decided that Mali would be the one
seduced. Kulap and Jodie started playing with Mali kissing and fondling her.
They soon had Mali's blouse open and the small bra unhooked. Mali tiny pert
breasts poked through the open blouse into the hands of Kulap and Jodie. Cliff
watched intently as Kulap and Jodie began sucking on Mali's breasts and ran
their hands along Mali's thighs under the plaid skirt.  
  
Mali squirmed as if she was trying to avoid being seduced causing the uniform
skirt to ride up her lovely legs. Cliff saw the cotton panties peeking out and
he was getting turned on again. He stroked his cock as he watched the
threesome. Kulap moved behind Mali and held the aroused titties in her hands.
Jodie slowly pulled Mali's cotton panties down and off her legs. Cliff saw
Mali's little erection pop out as the panties were removed.  
  
"Oh look at your clit, you are so excited. I knew you would like this," Jodie
said sexily as the game went on.  
  
Jodie leaned in and sucked Mali's cock as Kulap continued to fondle Mali's
tits. As Jodi knelt down and bent over her skirt rose up and Cliff saw her
cute ass encased in the cotton panties. He was ready to join the action. He
dropped his pants and underwear to his knees and moved in behind Jodie. He
caressed Jodie's shapely bottom through the cotton panties for several
minutes. Unable to resist the eroticism of the moment he pulled Jodie's
panties down to just below her buttocks. Jodie looked incredibly sexy with the
uniform skirt tossed up on her back with her panties below her bottom. Cliff
moved in closer and eased his throbbing cock into Jodie's sweet ass.  
  
Cliff held Jodie by her hips as he slowly fucked her. Mali was moaning with
the dual stimulation of Kulap playing with her titties and Jodie sucking her
cock. Needing to cum Kulap stood up and pushed her cotton panties down to her
knees. She held her plaid uniform skirt up and offered her cock to Mali who
gulped it down. Everyone was still dressed for the most part and Cliff
imagined that they were actually in a school room having sex.  
  
Sensing that Jodie was the only one not having her cock attended to, Cliff
gave her a reach around and stroked the small pecker. Mali was the first to
cum and Jodie swallowed very drop. Kulap came next and juiced in Mali's mouth.
Cliff was still banging away at Jodie's ass when Kulap knelt down and took
Jodie's cock away from Cliff. Kulap sucked Jodie bringing her off quickly and
Cliff followed flooding Jodie's rectum. Cliff remained in Jodie's ass and
caressed her lovely buttocks until his cock softened and slipped out.  
  
The four of them redressed with the ladyboys staying in their school uniforms.
They had lunch and took a break from the sex. They all agreed that it was very
erotic to dress up like schoolgirls and role play. After lunch Cliff had one
more request and that was to fuck each of them in the ass. They knelt down
side by side with their uniform skirts flipped up and their panties pulled
down to their knees.  

Cliff moved behind them and spent several minutes fondling and fingering each
ass. He lubed them thoroughly and pushed his stiff cock in them. He would fuck
one and fondle another. He moved from ass to ass fucking all three of them one
at a time. He loved the scene before him as it really looked like he was butt
fucking three schoolgirls. He came in Kulap's ass first and moved quickly to
shoot in Mali's ass before finishing up in Jodie's ass. Cliff was done and he
moved to a chair to watch the ladyboys as they pleasured each other.  
  
Later they all relaxed by the pool until dinner time. The ladyboys had changed
out of their school uniforms and put on their bikinis. Cliff thought it was
odd that looked sexier in the school clothes. Normally he liked the ladyboys
in their thong bikinis but that day he kept picturing them in the uniforms.
Cliff suggested just having appetizers and drinks by the pool instead of
dinner. The four of them relaxed until it was dark and time to turn in. There
would be no more sex that day as they were all drained. Cliff reminded the
ladyboys that he was having a few people from the office over tomorrow.  
  
SUNDAY SOCIAL  
  
Sunday morning after breakfast found the ladyboys busy preparing appetizers
for Cliff's guests. Cliff verified that there was plenty of wine and beer and
he had Mali make a batch of bloody marys and mimosas. His guests began
arriving about noon and they were greeted by the three ladyboys who looked
stunning as usual. Mali, Kulap and Jodie all wore silk outfits with silts on
both sides of their legs up to mid thigh. Their jet black hair was tied up in
a bun and they looked mysterious and exotic. Mali wore a red dress; Kulap wore
jade green and Jodie a silver dress.  
  
The ladyboys served the guests drinks and as they moved around the eyes
followed them everywhere. The men from the office kept checking them out and
catching glimpses of the shapely legs that appeared through the slits in their
skirts. Even the women from the office found the ladyboys to be alluring. Of
course they all thought that Cliff had female servants and never suspected
otherwise.  
  
The appetizers were served and Cliff told his guests that they were about to
experience some Thai food. "I had the girls prepare some special Thai
appetizers for you." Be assured that they are not too hot. The girls will
explain the sauces and their uses to you."  
  
Mali, Kulap and Jodie served the appetizers and explained the sauces, which
ones were mild and which ones were medium spicy. The guests loved the food and
they were grateful that the sauces were easy on the palate.  
  
"I thought that all Thai food was very hot," one girl stated.  
  
"Believe me these girls could prepare sauces that would burn a hole in your
throat. I asked them to dial it back for all of you," Cliff explained.  
  
"Thank God, this is plenty hot for me," another guest offered.  
  
"Can we see the house?" a pretty blonde guest named Jill asked.  
  
"Sure, bring your drinks and I'll show you around," Cliff agreed.  
  
As they toured the house the guests murmured comments to each other. They were
impressed with the house but they were also still in awe of Mali, Kulap and
Jodie. A couple of the guys wondered among themselves if Cliff was banging the
three servants. Cliff heard the whispers a few times and smiled to himself.  
  
"Do you think he is banging these chicks?"  
  
"What do you think? They're fucking gorgeous. You know he has to be banging
them."  
  
"Oh man, can you imagine being in bed with all three of those beauties?"  
  
Even the girls from the office were curious and suspicious. Jill the pretty
blonde with a gorgeous figure was convinced that Cliff was fucking his
servants. He never hit on her at the office so had had to be getting plenty of
pussy at home.  
  
In one room as everyone walked out the door Jill was the last one. She turned
back toward Cliff who was trailing the group and whispered to him. "If you
ever get bored with that Asian pussy and want some blonde stuff, let me know."
She patted him on his crotch and then turned to leave the room and catch up
with the others.  
  
Cliff told the servants to refresh the guest's drinks and then he took them
out by the pool. One guest whistled when he saw the setup out side. Jill
noticed it was totally private and she pictured Cliff and his servants naked
by the pool. The final stop was on the lower level and everyone's imagination
took off when they saw the massage tables and bathing pool.  
  
One guest whispered to his colleague, "I'm getting a woody thinking about what
goes on down here."  
  
The other guest nodded as he too pictured Cliff getting a massage from the
three servants and bathing in the pool with them. Jill had the same image and
she was already thinking about joining Cliff some day. She would love to be in
the same room naked with Cliff and the servants. Jill pictured the two of them
getting a massage and then being bathed in the pool by the Asian girls.  
  
By evening everyone had had enough to drink and they were all horny from their
erotic thoughts. If Cliff wanted to have an office orgy he was sure that
everyone would have agreed. He looked at Jill again and she was indeed a
beauty. There was a trip coming up where he and Jill would be together and
that would present an opportunity to test the water with her. Cliff made up
his mind to find out if she would back up her offer.  
  
The guest lefts and thanked Cliff for an enjoyable afternoon. Mali, Kulap and
Jodie all bowed politely as each guest left and the men took one final look at
the beauties. They sensed that not long after they were gone that Cliff and
his servants would be naked and having sex. The guests were right and as soon
as everything was cleaned up and put away the four of them were naked in
Cliff's king sized bed.  
  
Cliff fucked each of them as they took turns sucking each other's cocks. As he
fucked each ladyboy, Cliff thought about the people from the office and mused,
if they could see him now. Of course they would be surprised that the Thai
beauties had little cocks instead of pussies. After Cliff came a third time,
the ladyboys left his room and went to their room to continue their sexual
activities.  
  
Cliff lay in bed looking at the ceiling and thinking about his life. He knew
in time that he would return to the heterosexual lifestyle. He might even find
the right girl to marry and have a family. For now though, he was content with
his situation. He really didn't miss pussy and he had all the sex he could
handle. He was well off financially due to his uncle's inheritance. He had a
great setup at his home and he was having the best oral and anal sex one could
want. Cliff could see himself living like this for years to come. Life was
good!




End file.

