Trip Of A Lifetime Or Was It?

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Much better, look match now and no show bra"

Maria looked and saw herself in the mirror, which had appeared from somewhere. The top barely covered her, her cleavage showed more than she had ever showed before and the sides were cut low too, giving views of her tits, she thought she could see her nipples at one point.

"You buy and wear now ok" Siri asked handing Maria another drink. Maria again downed it in one, she was on holiday she thought to herself so why not enjoy herself. She didn't know anyone here so it didn't matter what she wore did it.

Siri said something to the girl and she went and got a bag into which she put a white skirt, a red skirt and tops to match. Maria's skirt was left on the table, but she didn't notice that.

Siri took Maria's arm and guided her out of the tent; Maria paid the girl for the clothes 2000 baht around £25 -30

Now they wandered around the rest of the stalls, Siri picked out several things from an underwear store, all had designer labels. All were really tiny and held together with very thin strips of material. She even got some suspender belts and stockings, Maria paid for these too.

She took Maria to bar next, ordered more vodka and then suggested a trip to the toilets. She held Maria and guided her to the back of the bar. She had the bags of clothes with her. Having been for a pee Siri waited for Maria to finish. When she heard door unlock she said "let's try these other things on now shall we." Maria was too light-headed to object. Siri Lifted her skirt, not that it was very long anyway and pulled her thong down, Maria automatically lifted her feet to slip them off. Then Siri took one of the new thongs from the bag and slipped them Mari's legs. It was black, see through and so small it only just covered her pussy. Then a suspender belt was pulled from the bag and fitted around Maria's waist and Black stockings slid up her thighs and attached to the suspenders. Siri then took another suspender belt from the bag and wrapped it around her own waist attaching identical stockings to it.

"Now we party and enjoy ourselves" she said to Maria.

Looking in the mirror Maria saw herself, all in black. Her tits showing at the front and sides. Her legs covered in nylon and she could see the darker coloured tops of the stockings showing under her new skirt. She felt strange, as if she didn't know the person looking back at her in the mirror. Before she could say anything Siri had grabbed her arm and pulled her back into the bar, which was now filling up. At least it was cooler in here.

"What is the stage for Siri? "

"Wait and see My Maria"

The stage was about 20 feet long and had several silver poles running from the floor to the ceiling. Music started and several Thai girls walked up the steps leading to the stage. They were all dressed in just Bras and thongs, some in stockings and all wearing very high platform soled shoes.

They danced around the poles. Looking quite miserable Maria thought to herself. The girls used the poles to rub their crotches on, grinding themselves against them.

Siri took Maria to a seat in a booth near the stage; she slid in first leaving Maria on the outside of the booth. When she sat down her skirt was so tight that it rode up and uncovered her stocking tops and if she sat with her legs uncrossed her thong covered pussy was visible. She tried several times without luck to adjust the skirt.

"Just leave it Maria, you are fine and no one will notice you amongst the other girls. They are real girls too Maria just like you."

They sat and watched the dancers grinding against the poles, then they turned and faced one another and started to gyrate their hips together, soon they were grinding hips against each other too. Maria was watching and it was turning her on. Siri had ordered yet more drinks and when they arrived she said "you like the dancing Maria?"

"Yes it's very good"

Maria then felt Siri's hand on her leg, rubbing up and down. "Look at the way they thrust at each other, very sexy isn't it?"

Maria couldn't take her eyes from the dancers, they were making her very horny, she noticed that a couple of them had removed their bras now and were openly touching themselves and one another. Several mean sat on stools around the stage were cheering and yelling as the girls all removed their bras. As she watched siri's hand was between her legs gently pulling them apart, spreading them, her skirt ride up even higher.

She didn't care anymore she was feeling light-headed and horny. The hand on her thigh stroking so lightly, going higher and higher.

Another hand slipped inside her top and was starting to rub her tit and then her nipple, she sighed and half closed her eyes.

The hand between her legs was inside the thong now at her pussy lips, probing her slipping in to her wet hole.

"Lovely cunt. Say it for me tell, me you have a lovely cunt Maria."

"MMMmmmmm that feels so good, I have a lovely cunt, it likes to be felt"

She was gone now, past the point of no return, in a bar/club in Thailand with a shemale who was fingering her. She no longer cared.

The hand squeezing her nipple was removed and it grabbed her hand and placed it between Siri's legs, then she felt the hardness of a cock in her hand, with her other hand she touched Siri's tits, they felt real. A girl with a cock.

"Ohhhh I love cocks" she heard herself say to Siri.

"Good because I want you to play with it, suck it and then let me put it up inside your cunt while we play with each others tits."

Maria was stroking the cock she found up and down, it felt quite big and it was certainly hard, all the time she was stroking her cunt was being invaded by Siri's fingers. On stage the girls were still dancing and now were removing their thongs, the guys were really cheering now. All eyes were on the stage. Maria felt herself cumming and she started to moan loudly. She came and came on that hand. The cock in her hand felt so good. She wanted to see it. Looking down she saw it poking out from under Siri's skirt. It was darker than any she had seen before and it looked about 8 inches long. The head was dark purple and looked huge, veins enlarged all down the shaft. Before she knew what was happening Siri had guided her head down and the head was inches from her mouth. She stuck her hand out and licked the head and then slowly took it into her mouth and began to suck. Using her tongue as she sucked she began to bob up and down on it. Faster, faster, sucking harder, with each up and down motion. Then she felt the cock start to jerk and her mouth was being filled with cum, thick and salty. She swallowed hard as the juice continued to squirt into her mouth. She drank it all.

Maria lifted her head up realising she was in a public place she looked round. No one had seen as far as she could tell. She picked up her glass and drank the vodka. Looking at Siri, who had a smile on her face.

"You like Siri cock Maria?"

Maria blushed but nodded her head and said "Yes I do"

Maria looked down and saw her skirt was so high she could see her pussy and the thong covering it was all wet, coated in her juices. She tried to pull the skirt down a little but Siri stopped her and said "leave it its ok where it is"

Some of the dancers were now naked and had left the stage and were dancing with guys, whose hands were wandering all over their bodies.

Maria was watching. Even through her drunken eyes she knew she had never seen anything like this before and didn't believe it.

"Want to come back here sometime? I think you like."

"Yes I'd like that Siri, I have never been anywhere like this."

"Come on, we go now. Siri take you to hotel, you need rest."

"Yes I need to sleep.

They left the place and got a Tuk-Tuk back to the hotel. The receptionist handed Maria her key.

"500 Baht for your guest" she said. Maria handed over the note, blushing as the receptionist smiled a knowing smile at her and Siri.

They walked to her room and entered. Siri went straight to the mini bar and got them both a drink. Maria didn't really want any more but drank it anyway.

Siri started to touch her again feeling her tits and stroking her legs, she was squeezing her nipples. Maria had very sensitive nipples and she was soon moaning. Siri stripped her, leaving just the suspender belt and stocking. She was soon between Maria's legs sucking and licking at her pussy, Maria felt her legs buckle and she fell back on to the bed. Siri didn't stop. She bit her clit and started to tongue fuck her. She was soon cumming again harder this time, pushing her hips into Siri's face. Maria lay there a moment and then felt Siri climb on top of her. She looked down and saw a huge pair of tits, with very large brown nipples. She reached for them and they were firm but warm and felt good in her hands. As she rubbed them Siri moved up her body and the cock was entering Maria, entering her pussy.

"Siri, fuck Maria, fuck her cunt with this cock. You like cock, like Siri cock."

"Ohhhh yes fuck me please fuck me hard"

Siri rammed her cock in and out harder and harder, biting Maria's neck while Maria squeezed her tits. This woman was the best yet Siri thought to herself.

She was fucking her very hard and Maria was screaming "Fuck me. Yes fuck me"

They both came together, Siri collapsing on top of Maria, kissing her mouth and feeling Maria kiss her back.

They went to sleep in each others arms, waking up in the early hours and fucking again.

When Maria woke later she saw it was almost midday and there was no sign of Siri. She got out of bed and showered. Then fixed her self a coffee and saw a note on the table. All it said was 'See you later. Siri'

Maria decided to go and check out the swimming pool. There were 4 at the resort and she chose one near the reception. It was bright and sunny and very hot. She put on a new black string bikini and a sarong and went to the pool.

She found a lounger and got a towel from the pool attendant. Rubbing sun cream in to her body before she went for a swim. She was really feeling good now but kept thinking about the previous night. Had she really done those things and let a shemale fuck her.

"Oh god there wasn't a condom used either" she said. Looking round she saw a Japanese girl looking at her. Maria just smiled at hr and hoped she didn't understand English.

She got out of the pool and lay down on her sun bed and promptly went to sleep. She woke feeling hot and hoped her back wasn't burnt, luckily the pool attendant had seen her asleep and moved an umbrella over her.

There were a few guests around the pool, mostly couples and they weren't English. Most seemed to be oriental.

Maria spent the rest of the day around the pool, even having meal at the poolside café. No alcohol she decided. She had drunk enough last night after all.

The day slipped by and as the sun began to get lower in the sky Maria went back to her room. The red light on the phone was flashing. She pressed the button and found a message from Siri. "Meet me outside the Andaman Queen at 8.30. and wear new clothes"

Maria wondered what the night held in store and could she really go out in those clothes she had bought at the market.

She showered again and went and had a pizza in the Italian restaurant. She returned to her room and found the clothes had been hung in the wardrobe. She chose the red skirt and top, both were the same as the black she had worn the night before. She wondered if she should wear stockings. Looking in the drawers she found a red suspender belt and another pair of black nylon stockings. They felt very soft and smooth and she decided to wear them. She pulled on a red thong which just covered her bald pussy.

"God I look like a slut" she said as she looked in the full length mirror on the wardrobe. The skirt was short again showing the darker tops of her stockings. The top was skimpy too showing her tits at the front and side again. She could see her nipples if she moved her arms!

She couldn't decide if she was going to wear these or not. She had taken another skirt and top out of the wardrobe. she thought she would leave them on a while and then decide. She applied her make up and perfume and got her red shoes from the rack. She looked in the mirror again and decided she would wear these clothes after all.

Leaving the hotel at 8.20 she got a Tuk-Tuk and asked to go to Bangla road. On turning into the road there were again so many people around. Music again blared from all directions. She looked out for a sign saying' Andaman Queen' she saw it on the left and realised it was where she had met Siri the night before. She asked the driver to stop and paid him.

Feeling very conscious of her dress she walked quickly into the bar area and saw Siri sat on a stool. She was wearing a bright blue dress, showing her tits and legs which were also covered in black nylon. Several other Ladyboys were sat there too and they were all dressed in a similar fashion.

"Hello Maria. I wonder if you come to see me again"

"Why did you think that?"

"I wonder if you really happy to go with Katoey last night"

Maria felt herself blush "Yes it was certainly a first for me"

"You wear clothes we buy at market I see, you must like, yes?"

"I'm not sure. They are a lot different to what I would normally wear on holiday."

"You wear short skirt and top last night so they not a lot different just shorter that's all. Here I got you drink, large Vodka and coke right?"

"Thanks."

"These are my friends" she indicated the 'girls' sat around her. Maria said "Hello" and they all replied in Thai. Maria didn't understand any of what they said. They all laughed and then said hello in English. The drink was strong but helped Maria relax a bit. No sooner had she finished one another was put in front of her.

"Trying to get me drunk again, Siri?"

"Just relax Maria you are on holiday enjoy, we are your new friends and want to look after you"

"ok, you are right I am on holiday and I do need to relax and unwind."

"Why no man with you?"

Maria explained what had happened between her and Glenn and told her all about Jason. Siri appeared to understand and made sympathetic noises in the right places.

"What you want do tonight?"

"I don't know, I am in your hands, I don't know anywhere here."

"Ok you want dance, see show or what?"

"what sort of show?"

"Katoey show if you like, in building at back here." She pointed back down the rows of bars to a building with bright pink and red lights outside. "It free to go in if you with me"

"Ok let's go and see then."

They walked down between the rows of bars, several girls trying to grab Maria as they passed them. They wanted her to buy them drinks, some even offered her sex.

They entered the theatre that was how the building looked inside. A stage with curtains and lights but with tables and chairs instead of rows of seats. There were several scantily clad Ladyboys stood chatting.

"Show start in a few minutes" Siri said and she ordered more vodka and coke.

The lights dimmed and the curtains opened. There on stage were about 10 Katoey, all dressed in stage girl costumes. They did several dances and the curtains closed. When they re-opened there were 3 on stage dressed in bra, thong and heels. The thongs barely covering their crotches. Siri explained that a lot of the performers had been for operations and were now complete women with pussies. She said she would eventually have hers removed when she had enough money.

The dancers did a slow strip and showed off their pussies with pride. After the music finished they got off the stage and one came over and joined Siri and Maria. She introduced her self as Upa. She was naked and Maria could see everything. Her tits were obviously implants as they hardly moved and her pussy had a tiny strip of hair above the lips, but it looked exactly like hers. Siri and Upa talked quickly in Thai and Upa kept looking at Maria and smiling. She said "Hello you like dance, you like Upa?"

"Yes very good, it's the first time I have seen anything like this and the first time I have met anyone who has had a sex change. You look very good"

"Thank you, you are very good , very good heart Upa can tell. You like to go club go dancing later?"

"Yes id like that." Maria said smiling. She hadn't been dancing for a long time and had seen several disco clubs in Patong.

"We go Shark club later good place, good music and it let anyone in."

"What do you mean?" Maria asked.

"They let Katoey in."

"Oh I understand now."

"Ok Upa, have to do 2 more show and then we go ok."

Maria and Siri went back to the bar at the front near the street and had a few drinks. They chatted about her life in Thailand and why she had decided to change her life and become a woman.

"It seems that if you are a woman you can get work easier than if you are a man is that right?"

"Yes women can get job entertaining in bars and clubs better than man. I come from Chiang Mai which is 14 hours on bus from here. I come here get work and earn money for operation. This is a place where all Katoey in Phuket come to work. Get paid for attracting tourists in and more if they buy drinks and food."

They were still sat chatting when Upa came and joined them. She was shorter than Siri and had an Asian complexion. Her dress was black and short and also showed her tits, which she was obviously proud of. She wore black platform soled shoes with 4 or 5 inch heels which made her a lot taller.

Siri said "I cannot leave here yet or I get no pay maybe I see you in the shark later."

"You sure you don't want us to stay with you?" Maria said.

"Yes you go, see you later, if not come back tomorrow and see me"

Upa and Maria left the Andaman Queen and walked up Bangla road. Upa wasn't like Siri she was more dainty and smaller. Even her hands were tiny. She looked just like a real woman. Maria had to remind her self that she had been born a man. Upa pointed out several clubs and bars that were good for tourists and several restaurants to avoid. She showed Maria the best places to eat and they were outside behind the Tiger Disco and Thai boxing hall.

"Upa take Maria to eat tomorrow, good food, cheap."

"Thanks I will look forward to that."

They walked passed Rock-Hard Go-Go bar. Music blaring from the outside speakers.

"Girls do pole dance there and then get men buy drinks maybe spend night with them for fucky fucky

"Oooo we would call them hookers in England.".

"What that?"

"Prostitutes I mean."

"Upa understand that word. Maria not hooker?"

"No! I'm not a hooker." She replied almost angrily. But she was dressed like one wasn't she. Maybe that's why Upa said that. She passed it off.

"Sorry I didn't mean to answer like that Upa."

"Its ok Maria I like you and it ok."

They walked up the steps into the Shark club and a draught of cool air hit Maria and she shivered.

"That's good, air-conditioned. I was getting very sticky out there. This is nice."

"Yes good for Farang" Upa replied.

"Farang, what is that?"

"Mean foreigner in Thai"

"Ok I understand."

The inside was dimly lit and there were already a lot of people in there, mostly Thai girls and European looking guys. The dance floor was already crowded.

They found their way to the bar and got drinks. Maria again being given a vodka and coke. She wasn't feeling so drunk tonight. There were stools at the bar and they found 2 empty ones and sat down.

"Maybe we find men, dance with us and buy drinks"

"Maybe, it's so long since I was in a place like this, I hope I can remember how to dance." She laughed as she said it.

"Its ok I not dance well either."

They weren't sat there long before a couple of guys came over and offered to buy them drinks, which they accepted. Maria had another Vodka and coke and Upa a breezer. The guys were Dutch and they were black.