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.

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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.