tagTranssexuals & CrossdressersHis Own Personal Ladyboy Ch. 02

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.


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.


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."

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