Ladyboy Literotica

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Ladyboy Literotica
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My last evening in Cebu and I meet Doris.
After a frantic afternoons sex, we relax over dinner.
Trans lesbian amazons suck and fuck ladyboy twins.
Areeya has been kidnapped and Jamie has to find her.
Aki tries to get Scarlett to shoot Jandaeng.
Scarlett shares a bath with Aki and prepares for the party.
Jamie finds trouble looking for whoever trashed the room.
Itsthe aftermath of the ambush, James gets a party invite.
James is drawn deeper into trouble.
James has to go to Bangkok and pao is still in hospital.
Pao had just been stabbed at Cockatoo. Its pandemonium.
James stays as Scarlett with Shane and Alex on the boat.
Jamie meets Shane again and becomes Scarlett.
Jamie comes face to face with Jandaeng in the ladyboy bar.
Jamie ends up in a Bangkok ladyboy bar.
Jamie runs into trouble on the way to Bangkok.
James becomes Jamie and heads to Bangkok.
James is confronted by the policeman about Kritsada.
James confronts Sam over her links to the journalist.
The confrontation with the blackmailing journalist.
James gets his punishment from Alex.
James and Alex have to deal with being business partners.
James finally decides where his future lays.
James goes to Bangkok after the fight with Alex.
James is back in Bangkok and feeling sorry for himself.
James gets some bad news and has a row with Alex.
Alex returns from Bangkok and reunites with James.
James gets some news from the UK and a present from Alex.
Alex goes to Bangkok and Samantha meets Areeya.
James meets Areeya's father. Something new happens with Alex.
James gets to do something new with Alex and Areeya.
James meets Areeeya's father and goes much farther with Alex.
Alex Areeya and James go for a boat trip.
Naive Englishman in Thailand falls in love with old friend.
Naive Englishman Bangkok meets old friend and gets shock.
Naive Englishman goes to Bangkok to get over his divorce.
Celine is a shemale, has been sold to the sex mistress Rachel.
Life in Thailand with a beautiful Ladyboy.
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He's captured and mind-fucked into becoming gay.
A seductive ladyboy changes a married man's life.
Girly boy is found out by his Black neighbor.
Businesman gets a surprise in a Thai bar.
Young man gets fucked by horny shemales.
I enjoy watching my Thai wife have sex with a ladyboy.
A man takes home the waitress from his favorite steak house.
Looking for something new I meet with a my first ladyboy.
Daniel, a straight man discovers that he's a transsexual.
Online chat with mysterious lady leads to unexpected desire.
Sexy Thai gf agrees to share her Ladyboy lover with hubby .
My first time encounter with a ladyboy.
A man's first TS encounter at a massage parlor.
Ladyboy Mistress shares submissive with other shemale Doms.
Clint picks up a hot shemale from the local club.
A filthy rich family full of incest and intrigue.
Local asian crossdresser taken behind the supermarket.
Lonely man in Vegas hooks up with a fine looking "lady".
An encounter when I was a stripper.
A drag queen submits to her boyfriend's perverted urges.
Story on how I found myself helpless against two Asian ladyboys.
Jake searches Craigslist and finds a ladyboy Mistress.
Ash takes dick in the ass from nerds and spin instructor.
Jake and Candy get ready and experience their next encounter.
A ladyboy scouted and recruited to service men in the army.
Best friend makes me his personal Ladyboy.
That unforgettable night, when he first met her...
An evil crime and extreme retribution for tranny fans.
She used to be a boy but she's all woman now.
One man in Bangkok, and his ladyboy prisoners.
Marie needs to be punished for what she is.
They thought they were just going to watch...
Dallas and Eve put on a live performance at a ladyboy bar.
Lady-boy Susan confesses her top fantasy.
A trip to Thailand for some forbidden fun.
John blossoms into Jenny...against his own will...
After a fight with the wife, a man helps a college girl/boy.
Banker seduced by ladyboy customer.
How my ladyboy girlfriend turned me into a Sissy.
Sissy boi makes the ultimate sacrifice for feminization.
Who cares what she's working with - bring it on!
A cishet man finds joy in being a trans woman's bottom bitch.
Local Asian crossdresser gets invited to the neighborhood.
In a world divided unfairly, the victims find love.
A bottom bitch experiences joy servicing his dominant top.
How a massage opened more than my mind.
Tammy's adventures with a ladyboy and two men.
A soldier comes home to meet a new friend.
Leslie takes control and lets me feel all of her.
Danika experiences a Japanese Encounter.
Multiple surprises for a couple during a Thai massage.
He discovers hidden talents through an accidental kiss.
Man has a suprise at the Thai massage.
Straight alpha male falls for a sexy Filipino ladyboy.
My next amazing adventure with a ladyboy.
The journey continues, now it is time for the cage.
Naive Englishman gets more involved with old friend.
What begins as an affair becomes so much more.
A new pair of lovers in a broken world.
An aunt with a special gift comes to visit.
Krissy relaxes with a massage with an unexpected ending.
A young guy meets a hot Asian ladyboy.
A sissy excursion leads to an unexpected meeting.
A man possesses the body of a "woman".
My journey continues with first humilation and more.
Amethyst finds he's - err, she's leading an ideal life.
Lisa helps out a newbie with a little secret.
Final chapter of a wild trip gets wilder.
A little experimenting never hurt anyone.
The weekend with aunt Chiharu continues.
Shopping continues and I have my first anal orgasm.
Pon and I joined as one in pleasure.
James returns from Bangkok with news for Alex and Areeya.
Our shopping spree continues and more.
Amelia goes to work with her new friend!
The shopping spree begins and humiliation continues.
The first week of my vacation with my transgender girlfriend.
An interesting dinner and my first threesome.
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A seductive ladyboy changes a married man's life.
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'Hi,' she said, her voice sultry. 'I'm the new maid. Lisa.'
The new maid had turned up at the house of Mark and Susan Reynolds. Mark had answered the door, and he was impressed.
Lisa was around thirty, with large brown eyes and wide red ruby lips. Her exotic features made Mark think that she was from somewhere near Persia. She was about 5'6" in black high-heeled shoes, long-legged, with dark hair that ran in curls down to her shoulders. She wore a white open-necked shirt that strained against her large firm breasts, and a gold locket rested against her open, tanned cleavage. But the thing that most impressed Mark was the pair of tight blue jeans she was wearing which showed off her shapely legs. He thought she had a slightly dirty look.
She was holding out a slender hand for him to shake.
Mark took her hand which felt warm to the touch and, for a moment, forgot to speak. Lisa put her other hand over her mouth and let out a giggle.
'He's Mark,' a woman's voice said. 'And I'm Susan, his wife.'
Mark was relieved to see that Susan hadn't taken his stumbling over the new maid badly. She could get very jealous at times – not that there was any reason to. Mark had been faithful to her throughout their entire marriage. Ever since they'd got together at school, he'd never even so much as kissed another girl. Now, fifteen years later, they had built a perfect life together, a good house, a good car and up until a week beforehand, a good maid. That was until Susan had accused the girl of stealing, and Mark had sat back as the fireworks flew. Now they had the replacement, this exotic looking beauty called Lisa.
They went through to the lounge, where Susan and Mark sat on the sofa and Lisa sat opposite them. As the new maid crossed her arms in front of her chest, Mark couldn't help but note what large breasts she had. Certainly bigger than Susan's. She was maybe more interesting looking as well. Susan would never have dreamed of wearing what Lisa had on – she was always bad-mouthing women who dressed 'like sluts'. The way Mark saw it, Lisa had some amazing attributes and was just making the most of it. He realised, as he gazed along Lisa's long legs, that he had a growing erection. Lisa raised an eyebrow at him and gave a slight smile.
Susan started talking about the tasks that Lisa would be doing round the house, a topic that Mark paid no interest in until it came onto dress-code.
'Clearly, what you are wearing is inappropriate,' Susan said.
Lisa was annoyed. 'What do you mean?'
'I can't have you wearing high heels to clean the house. Don't you have anything more suitable?'
'These are feminine clothes,' Lisa said. 'What a women should wear.'
'But you're my housemaid,' Susan said.
'Well,' Lisa said, placing one of her slender hands on her thigh. 'I do have a maid's outfit.'
'Fine. You can wear that next week. For today, you'll just have to see how you get on. Why don't you start with cleaning our bedroom?'
She got up and Mark once again drank in the spectacle of her looks, the never-ending legs and the tight jeans. This time he was given a view of her arse, the shapely buttocks that wobbled slightly as she walked. He watched her large breasts in profile, then had one last look at her sultry red mouth as she turned to smile at him.
'Will Mr. Reynolds show me round?' she said.
'No,' Susan said. 'I think I'll do that.'
Watching Susan stand up next to Lisa, Mark was surprised at how plain his wife looked. The lack of make-up might have made her more natural, but the smoky looks of Lisa intrigued him. Then there was Lisa's glamorous hair, compared to Susan's ponytail, and the height of the other woman, a good few inches taller than Susan. The new woman in his house was almost imposing.
That was enough of thinking about that, Mark decided. He wasn't going to go down that road.
Later, after Lisa had gone, Susan asked Mark what he'd thought of her.
'She seemed ok,' he said. Best not to sound too enthusiastic.
'Do you want to know why I hired her?' Susan was grinning now, pleased with herself over something.
'Well, when I was looking for a new maid, I started getting jealous. I didn't want you having any temptation. I even thought I might not get one at all. Then my friend Angela told me about a company that she'd used. Don't you remember that dinner at Angela's? You saw the girl when we were round there a couple of months ago.'
Mark knew who Susan was talking about. The maid had been introduced to him by Angela's husband, Tony. She was only small, just over five foot, a pretty little Thai girl called Janjira.
'Yes,' Susan said, still grinning, pleased with herself. 'Ladyboy Maids. Hired to keep your house clean and your husband true.'
She gave him a tap on the shoulder to prove how clever she'd been. Mark, though, was thinking back to when he'd gone round to Tony and Angela's house the previous week and stumbled across something he shouldn't have seen. Tony standing in his lounge as that pretty little Thai girl, her clothes stripped down to the waist to show off her petite breasts, lovingly sucked on his cock. Mark had seen enough to know Tony had come in that girl's mouth. The knowledge that the Thai girl was a ladyboy put a whole new spin on it.
Susan was still going on. 'I phoned up the agency and they sent us Lisa.'
Mark tried once more to make sense of it. He thought back to their new maid, and ran the image of her beautiful face and gorgeous body through his head. The black high heels and that little smile she'd given him on a couple of occasions. One of them when she'd caught him admiring her long legs. One when she'd caught a glimpse of his erection.
He tried to imagine her with a cock. Hidden away in the crotch of those tight jeans.
He shook his head a few times to clear the image away.
Susan let out a laugh. 'Don't worry, hubby. She'll be the perfect maid.'
That evening, Mark couldn't sleep. Ignoring the protestations of Lisa, and only telling her he was going out for a walk, he went out into the streets. He wandered around, not sure of where he was planning to go, until he found himself at Angela and Tony's house. The bedroom light was on. He was sure Susan had mentioned something about Angela being away visiting her mother.
Mark thought over his guilt. He'd remained silent over everything he'd seen a week beforehand, watching as the Thai girl gulped down Tony's cum. Tony stroking her hair like she was an obedient slut. Could that same girl be a ladyboy? He decided it was time to find out the truth.
He rang the doorbell. From beyond the door he heard the sound of a woman's light footsteps coming down the stairs. Maybe Susan had been wrong about Angela being away. Which was going make explaining his late arrival difficult.
But it wasn't Angela who answered the door. It was the Thai housemaid. She was as pretty as he remembered, young looking with an open smile and dark dreamy eyes. She was wearing a white silk kimono which contrasted with her brown skin. The kimono was flapping slightly open, and Mark caught sight of the naked outline of her small breasts.
'Mr. Reynolds, sir.' She leapt forward and embraced him. Mark wasn't quite sure what to do, but found himself hugging her back. She gripped him tightly and squeezed him, leant back and smiled. Her kimono was still open, and she saw him looking at her bare chest. 'Naughty,' she said, pulling it shut.
Tony arrived behind her. He was wearing just a t-shirt and shorts, surprisingly out of breath for a man of thirty. Mark thought that must have been the results of some exertion.
'Janjira,' Tony said. 'Leave Mark alone.'
She pouted at him as he pulled her back by the arm and turned her round. He slapped her backside and pushed her inside, then shut the door of his house.
'You have to forgive Janjira,' Tony said. 'She's very friendly.'
'I told you she's very friendly. Besides, you've only really met her once.'
The image flashed back in his head of his friend dominating the small Thai girl. 'I need to talk to you about that second time.'
Tony frowned. 'You're not going to say anything to Angela are you?'
'It doesn't look like you've quit the habit though.'
Tony shrugged. 'You wouldn't either if you had Janjira. She's incredible, Mark, the things she can do to your cock. When she's sucking it. When she's riding it. Man, when she's riding it, that's the best. She's only small, but the things she can do. I've never cum like it.'
Mark held up a hand. 'Christ, I don't need the details.' Then he thought of what he had come for. 'Well, one, maybe.'
For a brief moment, Tony was offended. Then he smiled. 'Yes' he said, 'It's true. How did you know?'
'My wife is using the same housemaid company as Angela.'
Tony laughed. 'So what does your one look like?'
Mark described Lisa. He tried not to go into too much detail, but he explained the long legs and the large breasts and the knowing smile.
'Shit,' Tony said, rubbing the back of his neck. 'You're in for a real treat.'
'But you should be,' Tony said. 'Do you want to try out Janjira? See what it's like to have the little ladyboy slut riding you?'
Tony shrugged again. 'So what? I'm having the time of my life.'
For the next week, Mark tried not to think of his friend's adultery. Even when Susan mentioned that Angela would be coming back early from the trip to her mother's. Mark made no mention of what might be waiting for her. Nor did he say anything to Tony. None of it was his business. He was best out of the whole mess.
That was what he was thinking as he answered the door to Lisa. She gave him a wide smile when she saw him. She looked so feminine that he still couldn't believe she was a ladyboy. He also couldn't believe what she was wearing. A skimpy maid's outfit, with her breasts pushed up and a frilly skirt that barely made it four inches past her crotch. Her long tanned legs were on full display and she was wearing a dark red lipstick that accentuated her lips and made them look wet and soft. How could this not be a woman?
'Morning, Mark,' she said, kissing him on the cheek as she came inside.
He watched her go straight upstairs and found himself admiring her legs as she went. He told himself to snap out of it. Then he heard her calling to him from the bedroom. He followed after her.
He walked into the room and he couldn't see her. The bed was already made – not of course by Lisa but by Susan. It had been her parent's bed, before Mark and Susan had taken it for their house. It had been the bed they'd used when they'd made love for the first time, and it had been their bed for their wedding night. It held a special significance in Susan's heart. Next to that was the photograph from their wedding five years before. Susan had been in her element that day, controlling everything, bossing the bridesmaids and the ushers. She had looked beautiful though.
He turned round to try and spot Lisa. He caught a sight of himself in the full-size mirror that reflected back onto the bed, then two hands were covering his eyes. He caught a scent of jasmine.
'Sneaking into a girl's bedroom is very bad,' a sultry voice said.
'But this isn't your bedroom,' Mark said. He lowered her hands.
Lisa stepped to the side and he found himself again looking at the top of her breasts which were trying to burst out of her top. The idea of this ladyboy in his bedroom, dressed in a sexy maid's outfit and calling herself a girl, was unsettling.
'So, do you want me here?' she said.
'Do you want me here?' Then she playfully pushed him in the chest, digging her long red fingernails into him. He told himself again that this was a ladyboy standing in front of him. It wasn't a normal girl wearing this slutty maid costume, but a chick with a dick.
'Yes, start here,' was all he managed to say.
But instead, she walked over to photograph of Mark and Susan.
'It was always my dream to get married,' Lisa said, drawing one of her slender fingers down the picture and smiling at Mark. 'I always wanted to find a man who would buy me a beautiful white wedding dress, a man who would look after me and make love to me whenever I wanted.'
Mark gulped. It had been a while since himself and Susan had done anything like that. He realised his gaze had drifted down to Lisa's crotch.
Then there was the sound of coughing. Susan had appeared at the door. 'We make a good couple, don't we?' she said.
Lisa's smile grew wider. 'A very good couple.'
'Back to work Lisa, like a good girl.'
Mark couldn't help note the sarcastic way Susan said the last word.
Later in the afternoon, he found Lisa struggling to pull down the ladder to the attic. Mark had to walk round her back to help steady the weight, and for a moment was pressing his body into hers. He could smell the flowery shampoo she'd used in her hair as they lowered the ladder. She almost let the ladder fall and he had to run his hand past her arm to stop, and he felt her smooth soft skin under his touch.
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