Turned into a Sissy Pt. 15

Story Info
A Weekend in Pattaya - the first evening.
2.7k words
4.67
7.1k
5

Part 15 of the 18 part series

Updated 12/25/2023
Created 02/20/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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
cd_luna
cd_luna
194 Followers

Hi,

here comes part 15!

Still writing about my experience in Bangkok, when my girlfriend (with an extra), slowly turned me into a sissy.

Hope you like this one as well.

I would love to hear your feedback below in the comments. Let me know, if I should continue to tell my story.

---

As mentioned in the previous chapter, my girlfriend and I were sitting one evening on the balcony, having a sip of red wine and discussing our first short vacation together.

My girlfriend had only very few vacation days, so every day was precious. We wanted to go somewhere seaside, but avoid long travelling hours or flights.

"How about we go to Pattaya.", she said, "It is only a two hours drive and you would definitely love it there."

She leaned towards me and kissed me, but had a somewhat evil-ish smile.

"What do you mean? I have not been there but heard that there are probably lots of ladyboy bars. But we don't need to go there, I got the best already."

"I have some ideas already and I think you will like it. Leave the planning with me."

The plan was to go there on a Friday evening after work and return on Monday evening. She moved some of her shifts, so that she had a weekend off without taking leave and only Monday was an additional day off.

"Don't we need to start packing, when we want to leave tomorrow after work? And should I organise a driver?"

I asked on Thursday evening, the day before we wanted to start.

"No need, I already booked a car. And we can pack tomorrow, no worries. Just send a message, when you leave work, so I can be home on time as well."

Friday was just a normal day at the office. I sent a message to her that I will be back a bit earlier to allow more time to pack.

'Be home at 5pm sharp.', was her reply.

I was surprised, but of course did what she demanded. When I arrived at the building, she was already waiting next to a car. I stopped, because she looked just gorgeous. She wore a very tight and short black leather minidress as well as black leather pumps combined with some golden rings, earrings and a golden necklace.

She hinted to the car.

"Just get in already and don't stand there staring like silly, baby."

I didn't ask anything, just got in the car and immediately the driver headed off.

"Baby, I prepared a perfect weekend for the two of us. Hope you will like it. Enjoy the ride and relax after a long week at work."

She handed me a glass of champagne, I saw that there was a cooling box in the car.

We took a sip and kissed.

"Thanks babe, you look incredible today, just like a queen. I cannot wait to arrive."

"Our bags are in the back, I packed for you since we anyways don't need too much for the short period. And here are some clothes to get more comfortable on the way."

She handed me a bag and then leaned to the driver and said something in Thai.

"I asked him to stop at the next rest area so you can change."

"Can I have a look at what you chose for me?"

"Of course you can."

And her evil-ish smile was back. I opened the bag. There were only a few items, a white crop top, bright pink hotpants and a string tanga. I looked at the top, it was white, very short and had a pink shiny print on the chest.

SISSY.

I looked at her, looked at the top. I knew I could not say no to it.

"Don't worry, we will not stay at a large tourist hotel, so you can relax. We will have a perfect weekend together and I thought, you should embrace your feminine side a bit more."

The car stopped and she told me to get changed. Before I got out of the car she handed me a pair of white Adidas sneakers, the three stripes in pink, of course.

I went to the restroom, closed the cabin and took shirt and trousers off as well as my panty and stockings. The cabin was not very clean, so it was a balancing act, not to let anything touch the floor.

I put on the tanga she gave me and then the hot pants. They did not cover my butt fully, it was really short. It was also so tight that the cage was obvious to be seen.

Then I put on the crop top. It actually felt good, it ended right above my navel and it fit me perfectly. Finally I wore the sneakers, put the other stuff in the bag and rushed to the car, hoping no one will see me.

But the car was gone. I spotted it at the other end of the car park.

Damn, I thought, she really knows how to get me. What were my choices. I walked across the car park. Fast, but not too fast, I did not want it to look like I am running.

I opened the door, got in the car, kissed her.

"Babe, thanks so much, I love the top and the sneakers, just the hot pants are a bit tight."

"I think it looks perfect on you and we will make a good looking couple."

A while later we arrived at the hotel. At the front door it said *Penthouse Hotel*.

(author's note: unfortunately it is closed nowadays, but in hindsight it was the best place to stay there. Rooms with special amenities, a LB Bar on the groundfloor and an indoor pool area, everything very nice, everything at a good price.)

We went inside and checked in, went upstairs to our room. It was huge, and special. There was a dancing pole in the room, a hot tub, a massive bed with mirrors all around. I was stunned, it looked really good.

I got all our luggage inside and before I could unpack our bags, she said

"We can do that later, no time now. We have an appointment in 15 minutes outside around the corner, so not much time left."

She lifted her dress and pulled her panty aside, her cock popped out and was already hard and wet.

"But there is always time for this."

She smiled and I got down on my knees, kissed the tip of her cock and licked her shaft all the way to her balls, sucked and licked them.

She suddenly grabbed me head and held it firm.

"Not that much time!", she laughed and then started to fuck my throat deep. She pushed her cock inside my mouth until my nose was touching her belly, I gagged. She pulled out and pushed back in, faster and faster, I gagged, spit was dripping from my chin on the floor, she continued to fuck my face hard, throwing her head back, she clearly was already close to the egde. It did not take long, before she shot her load in my mouth, she pumped one stream after the other and I swallowed all of it.

"Baby, I so needed that. But what did you do to your hotpants. Go and dry them."

I looked down and saw a dark spot, my little one must have leaked heavily in the cage. I cleaned the floor then went to the bathroom, cleaned my pants and dried them with the hair drier.

"Ok, let's go!"

I followed her downstairs and saw that there were gogo bars in the ground floor. It was only around 7:30pm, so it was rather quiet, but quite a few girls were already there.

We went not far, just 50m down the street. The shop was a beauty parlour.

"Just relax, you will enjoy it."

She talked to the lady at the entrance, it seemed that everything was arranged. They did not say anything to my look. They brought us to a couple room in the back.

Two girls came in and greeted us.

"Thank you for visiting. You have ordered full body scrub, a facial treatment as well as manicure and pedicure for two, is this correct?"

"Yes, correct.", my girlfriend answered. So they started and I did not say anything, just let it happen.

I always had my body waxed, but after the full body scrub, it really felt even smoother. They also gave a moisturising treatment.

The facial treatment was a long procedure with different masks, serums, cleanings in between.

And while that was ongoing, more staff entered and started to work on hand and feet. I could feel all kinds of cleaning, cutting, scrubbing.

I relaxed.

It felt good.

I heard long deep breaths from my girlfriend, she fell asleep already.

I also just concentrated on the music in the background and also fell in a light sleep, it was super comfortable, I loved it.

My girlfriend woke me up, she stood next to me.

"You look gorgeous, baby."

I slowly got up from the massage table. Looked at my hands and saw that my nails really looked different.

"They gave you a clear top coat. It is only a bit shiny, but protects your nails and makes them look better. And at work no one will really notice. As long as you keep your shoes on."

She giggled.

I looked at my feet and saw that my toe nails were bright pink with a silver sparkling effect. I was not even shocked or surprised, I loved it.

"Thanks babe, that colour looks great, I really love it!"

She leaned down and whispered in my ear:

"You truly are a real Sissy. My lovely little Sissy. Have look in the mirror, there is more to see."

I saw that they applied a light makeup, nothing very bold, it looked really good. I liked especially the light pink blush and matching lip gloss.

I felt good and she looked happy as well. Her nails were also freshly done and her makeup resembled mine, just a bit bolder.

While walking out of the shop, she said

"Today is your evening and I reserved a table at a really good restaurant. But we should change first not to be underdressed."

We rushed back and undressed, took a really quick shower and then opened the suitcases.

She asked me not to look, but to wait.

"Turn around."

There she was, wearing a black satin, knee long tight evening dress with open back and sleeveless. She wore a small golden belt, golden choker, earrings and bracelets as well as golden high heel sandals.

"Wow!"

I did not know what to say, felt that my little one in her cage tried to get hard.

"You look gorgeous, again like a Queen. My Queen!"

"Baby, tonight we will both be that. Here are your clothes. Hope they fit, I just bought them new for you."

And she pointed towards a dress she laid out on the bed.

It was the same as hers, but in golden shiny satin. And there were black high heels, a thin black belt, choker, bracelets and rings, even black clip-on earrings.

She hugged me tight.

"Baby, tonight we will both be queens. Let me show you something."

She showed me the black choker, it was soft, made of satin, and had a small golden embroidery saying 'HERS'. Nothing more. I loved it.

Once I was dressed as well, we went downstairs and asked someone at the reception to take a photo of us and then got in a cab to the restaurant. In the cab we had a look at the photo, it looked really like two Queens, my makeup was good enough to hide my male face and since my girlfriend used lots of hairspray to get my hair in a feminine short haircut style, it was so not too obvious.

We drove to the 'Cafe des Amis', which was and still is one of the best restaurants in Thailand. Not cheap (well, still cheap compared to fine dining in Germany), but very, very good.

And I was like in a dream, when we walked through the restaurant to a quiet corner table, it felt like everyone turned there had when we passed by. It did not feel strange, it just felt good.

We sat very close at the table, held hands, like a couple fresh in love, giggled the whole evening and just had a great time with great food. And we finished a bottle of wine after having a cocktail before dinner. So both of us were a bit tipsy.

Once we finished, we paid the bill and took a cab back to the hotel.

"Baby, I want to go dancing, let's dance."

I looked at her.

"Where do you store your energy, babe? After a working day, travelling, pampering at the beauty parlour and great dinner and drinks, I could just fall asleep immediately."

"Not yet, it is just 11pm, the night just starts, baby. I have an idea and it will be fun."

Once we arrived at the hotel, she headed straight to the ladyboy bar on the ground floor. It was low season and hence, not very crowded, but many ladyboys dancing between tables and on the stage. Some of them sat around obviously bored.

But I soon learned that my girlfriend was definitely a party animal, she chatted with most of them and got us more drinks.

I was totally drunk. So drunk that she managed to pull me on the stage and danced with me.

All the time she made compliments, how good I look and that she wants me. At some point she whispered in my ear, "Tonight my queen, do you want to take me?"

Before I realised what she asked, she was gone again and came back with another drink.

We made out at the table, I felt happy, horny, drunk and tired at the same time.

I don't know, at what time we went to our room. Or better she went and dragged me, I could not walk. Her drinking capacity was astonishing.

Once in the room, we made out, I kissed her deep and took her dress off, kissed her everywhere, every inch of her body. Then she did the same with me, it felt hot, I was horny, wanted to have her.

Suddenly she sat on top of me and showed the key, slowly opened the lock of the cage and took it off.

My little one was leaking heavily. And it was soft.

She took it in her hand and massaged it, massaged my balls, it felt incredibly good. But I did not get hard. She massaged a bit longer, sucked it a bit and sat on it to let her hole touch it. But it was limp, I was close to crying.

"Don't worry and don't feel bad. I don't like to be taken, I would have done it for you. But it looks like you also prefer it the other way round."

She kissed me deeply.

Then she took the cage and locked my clit again.

"Do you feel better again? No need to feel embarrassed, because now it is clear who is in charge?"

I nodded.

She cuddled close.

"Baby, I love you just the way you are. You don't need to prove me anything."

"But I am still a man."

She looked at me and took out her phone, showed a few photos we took tonight.

"You are not the most manly of all men, are you?"

She giggled.

Naked as we were, we got another whiskey from the minibar and chatted some more before falling asleep.

At some point she asked, "did you like your day?"

"It was perfect, thanks Babe. I really felt like we were two Queens tonight. And it was also fun dancing at the bar downstairs, although I was really drunk already."

"Tomorrow will be different. Today was for the Queens, tomorrow, there will be only one Queen. But I think you will also like it."

Then we fell asleep.

To be continued in the next chapter.

Hope you liked it and sorry for the length and not a lot of sex involved this time. But I try to remember everything as accurate as possible.

cd_luna
cd_luna
194 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
MilllMilll5 months ago

why little one?? its a clit

AnonymousAnonymousabout 1 year ago

Such great memories of soi 7 and the crazy nightlife.

private_loginprivate_loginabout 1 year ago

Waiting impatiently for what will happen the next day.

AnonymousAnonymousabout 1 year ago

Wow you are so lucky. I wish I were in your place.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Bottom Bunk Bitch Ch. 01 Brendan enters prison and finds himself becoming Brenda.in Transgender & Crossdressers
Neighbors Sissy Son Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
Prison Sissy Ch. 01 First day at prison.in Transgender & Crossdressers
The Sissy Exchange Program Ch. 01 Mistress Kristy finds her mark.in Transgender & Crossdressers
Feminizing First Step Ch. 01 A mother begins to feminize her son. First, a new swimsuit.in Transgender & Crossdressers
More Stories