Turned into a Sissy Pt. 10

Hi,

here comes part 10! (yay, a special celebration should be done)

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.

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We were back to normal working days and short weekends after the birthday party. My girlfriend had to work again 6 days per week, sometimes even 7, to jump in for other colleagues.

During that time nothing too exciting happened, normal relationship stuff, you could say, including everything that's related to it. Apart from me fucking her, of course. I never got to do that so far.

The strange thing was, that on one hand I really desperately wanted to fuck her, but on the other hand, I felt a similar excitement, when I could suck her, feel her cock in my ass, or taste and swallow her cum. I just loved her taste. And in addition, I started to realise more and more that I was most happy, when she was happy. Be it with my serving, cooking, or my oral skills.

After she called me a Sissy for the first time, she rarely used it. It was some time later that this came up again, as you will read later on, and in the next parts.

During that period I was also a few times on business trips abroad and she unlocked me for those and took my promise that I do not touch myself, when the cage is off and that I especially do not cum.

Although my balls were really full, since I did not cum very often, I always stayed strong. Or it is more precise to say, it was actually not a problem for me. When I was away and unlocked, I did not even think about my little one, and I was rather embarrassed when I got a morning wood in the hotel and jumped right under the cold shower. It felt strangely wrong, to have a hard little one.

On those business trips, she only allowed me to take suit, dress shirt and shoes, all other clothes had to be feminine. At the beginning I really feared that anyone will notice. But it never happened.

And I also realised, would you actually recognise, if someone during a biz meeting wears stockings under the trouser? Or in a restaurant? Usually that's nothing anyone is focusing on. And once you see it like that, it is much more relaxed to wear feminine underwear. And that housekeeping in the hotels saw my satin pyjamas? I did not mind. So also biz trips became different than before, but normal, just in a new way.

And whenever I returned from biz trip, my girlfriend immediately put my cage back on. Sometimes she even picked me up at the airport when she had time and handed the cage to me there, asking me to put it on in the restroom.

So a few weeks passed fast, most with less exciting things to tell. Hence, I fast forward a bit. If you like to read more about everyday life together, please let me know.

At some point she introduced one new habit to our routine, which related to my full balls. One morning she noticed not for the first time that I leaked a lot in my cage at night, because my balls were just too full.

"Baby, I don't want that in my bed. Lick it up immediately and then change the sheets."

Of course I did as she requested. Once I returned, she sat at the side of the bed and asked me next to her.

"We need to find a way to avoid that you leak so often."

"Sorry", I lowered my head, "but I am still a man and really need to empty my balls sometimes."

Suddenly she slapped me in the face.

"I don't care about your supposedly manly desperate needs. You knew that from the beginning. And I cannot feel that you are too much of a man, actually. That's why I love you."

I gasped and was really confused.

"I tell you what we do, meet me tonight after work in front of the hidden closet. I will text you at what time. Now get ready and wear a pink garter belt and stockings today under your suit as well as a pink panty. And pack a pair of high heel pumps, jeans shorts and a top."

For those who don't know, The Hidden Closet is one of the few sexshops in Bangkok, where you can buy toys, fetish gear and all kinds of stuff.

So we got both ready for work, but as you can imagine, I was a bit distracted by what she was planning. Some time in the afternoon I received a text, but she said only, that she needs to stay a bit longer and she asked a friend to go and meet me there. After those weeks being together with her, there was not a lot that surprised me anymore.

So I waited for the next text that told me at what time I should meet her friend.

While in the taxi, she sent another text, telling me to change the shoes already. Since I wore high heels quite often when we were outside together in the evenings, that was not surprising. I took out the high heels from the bag, changed my black business leather shoes to those. I packed a silver pair with about 10cm heel, so still quite comfortable.

Once we arrived, I paid the driver and saw her friend already, it was the shop assistant we had my first shopping trip with. The one of my first threesome. She smiled and hugged me, kissed me on the cheek.

"Let's go upstairs, I have some instructions for you." She said, but since her English was not very good and she was not too comfortable speaking it, she mostly said nothing, but showed me notes, which my girlfriend sent her.

The shop is on the second floor of the building, hiding in a barber shop. Once we were inside, she showed me the first note.

'Go to the changing room. Afterwards give your work clothes to my friend.'

Of course I knew what to do and actually felt happy. I went to the changing room, took of suit and shirt and put on the jeans shorts and the top I brought.

Then I packed everything and gave my bag to the girl.

She took some makeup from her bag and just lightly added some blush and lipstick to my face, while I was still sitting in the changing toom. She smiled, took a photo and most likely sent it to my girlfriend. Then she grabbed my notebook bag from work, just took out my phone and handed it to me, smiled, turned around and left.

Now, that was something new. I did not know what to do, just sat there. I did not dare to write a text to my girlfriend, I knew she would not like that. I took my courage, stood up and walked around the shop. The shop assistant did not notice or did not care. Most likely the latter. I looked through frilly clothes, looked at toya and plugs, latex dresses and skirts, many, many pretty things. They also had masks and gags, I browsed around, noticing that I was always thinking how she would like it, if I wore the things I saw. One corner had some cos play outfits and while I was browsing through the dresses there, I suddenly felt a hug around my waist and a kiss on my neck.

"I knew you will like it, baby."

I turned around and kissed her.

"But now we need to get to Business. We are here not for fun, but to find a solution. Let me ask."

She went to the counter and said something to the guy. He came over and looked at me then lead us to the area with butt plugs and other analy toys.

"What do you need."

Before I could say anything my girlfriend jumped in.

"She needs a toy that helps to milk her. She wants to be a Sissy, but still thinks too much with her little cock."

I blushed as I probably never had in my life and never will do again, so guess. I was embarrassed to a level that I cannot describe. I turned around, but she grabbed my hand, kissed me and whispered.

"You know it is true."

The guy however, did not care. He has probably already seen everything here. He just grabbed something, a dildo or plug with a strong curve and pointy end, then explained something in Thai and my girlfriend just nodded.

"This will do, now we just need also a larger plug for you. Your favourite one is too small."

She grabbed one made of steel, like my current one, just larger diameter. She went to the washroom to clean it and returned, took my hand and lead me to the changing room.

"Bent over."

She pulled down my shorts and panty, spat on my hole and the plug, then slowly pushed it in. I tried to relax, but it felt much bigger than the old one. She pushed forward until it was firmly in place.

"OK, let's go."

We went to the counter, where she put the empty box on the table, and I paid for both toys.

"Babe can we return here? I found quite a few clothes I would like to try."

"We definitely should do that with more time to spent here."

We got in the cab back home. The plug felt uncomfortable, but I knew, I had to get used to it.

Once at home she told me to unpack and wash the new toy and to undress apart from stockings, garter belt and high heels.

A few minutes later I returned to the living room and she looked very serious.

"Sit down, we need to talk now."

I sat on the sofa opposite from her.

"Now listen, I understand that your balls are full most of the time, because it is hard to get an anal orgasm."

After the first one, I actually rarely reached one, when she fucked me. Only on very few occasions, but it was always the same sensational feeling. But really only very seldom.

"I will help you with that, but I don't want that you get any special feelings. Once a week, I will milk you. Let's try if the toy works, which we just bought. And you will clean up of course. If necessary, we do it more often. But this should be a technical procedure, we schedule it and we do it. You won't get my cock at that time or any other pleasure is that clear? I just don't want that you leak that much."

"Yes, babe, let's try."

What else could I say. I had no chance to change it anyways.

"Good, get on the floor on all four."

I did, then she pulled out the plug and added a lot of lube, before she slowly inserted the new toy. It was a strange feeling, once it was in. I could feel how it reached my prostate, there was immediately a feeling of pressure.

She started to twist the toy a bit, moving it slowly, she clearly learned what she should do. It was such a strange feeling, I was there, on all four, getting my ass toyed, but somehow it had nothing erotic to it. But still I could feel, how the pressure increased and after not very long time, I could not do anything, but cum leaked from my little clit. My girlfriend stopped.

"Good girl. Just once more for today."

So she continued. The same strange feeling of pressure building up. And again after a few minutes, I came again.

But both times were very different to my few anal orgasms or a normal orgasm, since I did not feel anything, only some relief, but no pleasure. I did not like it, but she approved.

"That works better than I thought. Now lick it up. Then prepare dinner for us."

She stood up as if nothing happened and walked outside on the balcony.

This really became a weekly routine now. I have to admit, I hated it. Every single time she did that, I hated it, because it was really like bringing your car to the inspection. She purposely did it always in the most unerotic moment. The only goal was to empty my balls, nothing else.

It was just a small additional routine, but another step on my way to being a Sissy.

But of course, not everything we did was that surprising or extreme in some way. In the next chapter I will write how we planned a weekend, where we had the whole Sunday to spend for ourselves. My girlfriend suggested that we visit Ayutthaya, the old capital, with its ancient ruins. There is also a small floating market and other things to do.

We had a great time there and afterwards at home.

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So this is to be continued in the next chapter. Hope you liked it, please let me know below in the comments.