Turned into a Sissy Pt. 01

Story Info
How my ladyboy girlfriend turned me into a Sissy.
1.2k words
4.4
97.2k
102

Part 1 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
195 Followers

Prologue

A bit of background, I am a crossdresser since a long time and over the years had quite a journey, from closed cd to being a good sissy. And I thought, some might be interested to hear about my journey, so I decided to share it.

Hope you enjoy my journey, please leave comments to let me know, how you like it.

So here comes

Part 1:

Well before corona times I was sent for a bit more than a year to work in Thailand. I stayed at a serviced apartment near Sukhumvit Road in Bangkok on a high floor, enjoying great views of the city.

I was already crossdressing before for a long time, so being in this city with ladyboys being accepted and a normal sight, was heaven for me. However, at that time I did not yet explore my sub side too much, did not realise that I am actually quite a sissy slut. But that was about to change and here is how.

One day I met a cute girl at a hairdresser in a large shopping mall, she cut my hair and we chatted a lot, had a good chemistry. It became clear that she was not born as a girl. I took my courage and asked her out for a coffee after work. We chatted all evening and met again the next evenings after work. Everyone who thinks, girls are easy to get in Thailand, well, no. Especially not, if they are not working in certain bar areas, I guess.

When we met, I was always coming from work wearing a suit. At our fourth or fifth date, I told her about my crossdressing and showed her some photos. She told me she really liked it. She was also very open and told me, she had her boobs made but kept her extra, because she loves to be active. Of course, I told her that I sometimes like to be topped, but did not do often (yep, this was before my other stories happened, which i posted). After having dinner and a few drinks at this date, we went dancing in a club. This was when we first kissed and then actually kissed a lot on the dance floor and at our table, she made me extremely horny, I have to say, she danced in a very sexy way. But later, she left again, left me there with my hard little cock in my trouser.

Next day was a weekend and we met for lunch, went for shopping and did a tour on the river (btw for all who haven't been there, Bangkok is a great city, so many sights, friendly people, great food). She was wearing a very short dress and really made me crazy. We kissed and held hands, but that was it. In the evening, after dinner on Sukhumvit Road and a few drinks, I asked her, if she would like to come for a drink to my apartment and she finally agreed. Me and my hard little one were very excited.

We went to my apartment, fell immediately on the sofa and made out. When I wanted to undress her, she stopped me and said, "i told you before I am active, but I actually am quite dominant as well, is that fine for you? Otherwise it won't work with us." You know, what I did. Of course I told her it is fine. I just wanted her. (looking back, this was the best decision in my life. But little did I know at that time.)

She smiled, kissed me and said "That's great, but let's take it slow." which of course did not match my hopes. That night, we sat on the balcony and chatted and drank a lot and later both fell dead asleep on my bed. Again no sex, I was a bit disappointed of course. Disappointed and totally drunk.

The next morning I got us some breakfast from a coffee shop downstairs and brought it her to the bed. We lay there and suddenly she said "we should go to the hospital today and take a health check, we don't know each other for long, but we both want more." Of course I happily agreed, and we went to the Bumrungrad hospital together. I thought that finally I can fuck her that day, having my male self thoughts. Again, little did I know.

The whole process took actually quite some time, and result was both of us had no stds, so all was fine.

With the result in hand, when we were still in the hospital, she whispered in my ear "I want you." We took a cab to my place, closed the door, but before I could even kiss her, she went to the living room, stood there, lifted her dress and said "suck me." I wanted to kiss her, but she just pushed me down. I knew what to do, I pulled her panty down and saw her mid size, perfectly shaped and yummy looking cock. She was already hard.

I kissed it, then started to lick her shaft, her balls and took her in my mouth, starting to suck her and slowly take more of her in my mouth. She moaned, seems she liked my blowjob skills. After a while she pulled me upwards, kissed me, we both undressed each other, kissing and caressing every inch of our bodies. But she did not touch my hard little one at all, she looked at it, looked then in my eyes and just ignored it. When I asked, if she would like to taste me, she just said "no hurry, we have plenty of time".

So we made out more, she again directed me to her cock and I continued to suck her, while we both lay on the sofa. Suddenly she held my head on both sides firmly, pushing me down on her, so my nose touched her belly. I just loved this feeling, and she tasted and smelled really good. After she released me, she came closer, kissed me and asked, "are you ready?" I just nodded and asked her to be gentle, because I have not been fucked for quite some time. Then I turned around, head down ass up, she spit on my hole and positioned herself, before slowly entering. She slowly but steadily pushed inside me, until she was all the way in. It felt great. She leaned down, kissed my neck and whispered "will you be my bitch?" of course I said yes. (from that moment she started calling me her bitch, sometimes even in front of her friends, which made me feel really humiliated, but I somehow liked it.)

And then she started to fuck me, first slow, then getting faster and faster. Suddenly she pulled out very quick, told me to turn around and came immediately on my face with big loads.

Afterwards she kissed me, my face still full of her cum, my cock still hard, but she did not care. She said that next time, it will take longer, she was just too fully loaded. Then we cuddled a bit, got a drink and sat on the balcony, still naked (benefit of high floor apartment with no opposite building) and with her juice drying on my face. She asked me to show her some of my female clothes, she wanted to see, how I look in them in reality and not in photos.

But that's for the next part.

Hope you liked this, I would really appreciate your feedback. And apologies, not too much sex this time, but bear with me, next part will be different. Also apologies for my English, I am not a native speaker.

cd_luna
cd_luna
195 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
20 Comments
AnonymousAnonymous3 months ago
Neighbors Sissy

My firet time getting fully made up and dressed as a sissy woman was different .My neighbor a nice black man caught me made up.I now am sex slave to him and his friends.My first time i got fucked and made to suck all thrie cocks.I got fucked so many times i could not walk.So they made me suck their cocks again and again .

MichaelfantasiesMichaelfantasiesover 1 year ago

Very arousing story! I haven't really got into the Dominant trans-girl idea, but this story kept my interest! Would I let a pretty, dom gurl top me, or make me suck HER cock? WOW! Probably, as I AM submissive!

Royse69Royse69over 1 year ago

I have read this twice, I want to hit up Thialand so bad

Loveit01Loveit01over 1 year ago

Love the beginning, it would be great if he being her bitch was trained and told to hang out with all the other sub bitche shemales as girlfriends of her other dominant friends. Story so far is coming along nicely.

AnonymousAnonymousover 1 year ago
Older Sissy

I have been a cross dresser sissy for many years now.I have changed my body in to a full on woman.Hairless body slim waist 38d breast long hair with long nails.I have no trouble passing as a woman in public.But now in am off to cress off one thing on my list of things to do.I have had three some with two men and two women and a women and man.But now a full on gang bang but not sure how many or with men or mixed.I slipped in to a shinny body stocking no bra no panties high waist 8 strap garter belt black ff stockings and 6'' red stripper heels with a red short slip dress.Hair and make done and red lip stick .Once in the motel room there were 8 men 4 women some with some clothes on and some with no clothes on.My dress was removed and a big hard black cock was pushed in to my ass.I was made to suck all their cock and eat all their pussy and ass.Every one fucked me many times that night.I swallowed so much cum my belly hurt and cum ran out of my ass.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Sissified Ch. 01 Young boy is helped by his hot tutor in his transformation.in Transgender & Crossdressers
Hypnosissy 01: Becoming a Cocksucker Straight guy watches porn tapes that are not what they seem.in Fetish
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
Trapped and Trained Ch. 01 Man is drugged, then dressed up and trained to be a slut.in Transgender & Crossdressers
More Stories