tagTranssexuals & CrossdressersHis Own Personal Ladyboy Ch. 01

His Own Personal Ladyboy Ch. 01

bywalterio©

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."

Report Story

bywalterio© 5 comments/ 39148 views/ 14 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel