Confession

Hello Everyone,

This all started when I was 18 years old. Just like any other 18 years old boy I was browsing through the porn website for some porn to watch when I came across a crossdressing video in which the man was forced to wear female clothes, accessories and makeup and then treated as slave to do household chores and then fucked in ass by strapon.

Hi, my name is Suraj, who is 21 years old and have a fantasy of being a crossdresser. I used to masturbate by thinking scenarios of that. Few time when I was home alone I managed to try my mother's undergarment and got aroused quickly and unloaded my cum on the floor of the bathroom. This didn't went long as I have to move to hostel for my studies and nothing was possible their by masturbation continued.

When after completing my 3 years of education I visited home for holidays something great happened which changed my life. While at home I was asked to accompany my elder cousin sister to Mumbai for her interview and help her in settling for a job. As her job was final and that interview was just the formality, so I was asked to be with her for about 2 weeks as the company would provide the hotel to stay in till we make her living arrangement in the city. Company provided us with a good 3 star hotel and we stayed there of about 12 days.

We reached Mumbai on 3 Dec as it was Sunday and the formalities and interview was on next day we decided to take rest and planned to roam around in the evening but none of us was feeling tired so we started talking. We both were in the same room as we grew up in a joint family in the same house so we didn't had a problem, we started talking about life and then relationships, we both were single at that time, she used to have a bf back in our hometown but she dumped him and I have been single whole my life till then and she asked why I haven't got into the relationship being a good and nice guy so I said that I was never able to find the girl that I liked and once when I did she friend-zoned me and after listening to that she started laughing and out of no where I just got the courage to ask her if I can confess something to which she agreed.

I told her about the porn I watched and all the crossdressing stuff I know and she was shocked and she sat quietly in opposite corner of the room and she started using her phone to which I got scared and said don't tell anyone, to which she agreed and asked me to come close to her and I went.

She:- Have you ever tried to be completely dressed as a women/girl?

Me:- No.

She:- So do you wanna try.

Me:- Yes.

She:- Come with me.

She took me to the bathroom and asked me to strip all me clothes and get in the tub for the bath, she told me good girls take bath before they get ready. I did as she said.

She:- Okay from now on till you are with me you will do as I say and wear only girls clothes in the room and we will figure out about going out.

Me:- okay sister.

She:- From now on I am your mistress and you better call me that or you will suffer.

Me:- Yes mistress.

She:- Good.

Now she asked to dry myself and wear the clothes she has taken out for me. The clothes consist of a red pair of matching panty and bra, with a green legging with black and white top, she asked me to wear the bra and panty and while I was doing that she saw me in trouble and helped me by telling me how to position my dick within the panty and then stuffing the bra with some cotton, and then she made me wear the legging and the top. After making me dress she made me sit and did my makeup starting from nails, on which she applied a pink nail polish on hand and toes, after the nails she applied foundation over my face to make it even tone and then took a eye shadow and applied on my eye lids and after that she went on with my eye makeup using eyeliner and kohl(i.e. kajal). After the eyes were done she did some of my other makeup making my cheeks look pink and then she went on to lipstick of matte red shade, which I kinda like. Once my makeup was done she made me look myself in the mirror and for once I was stunned to look at myself as a beautiful girl..

After my makeup was complete and I was fully dressed, she said that she have something in mind and will arrange for the things while coming back from the interview tomorrow, by the time she made me ready it was evening and we both were hungry so she asked me to order the food and after the food arrived we both ate, while having food she asked me to take care of the makeup as it must not get ruined.

I tried my level best to hold on to the lipstick and was successful upto great extent, after the dinner:

She:- Do you want to change in nighty or want to sleep in those?

Me:- As you say mistress.

She:- Okay so you sleep like this but before than remove your makeup.

Me:- okay ma'am.

I did as she said and she was glad, that night before sleeping I thanked her for not freaking out and understanding me.

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I would appreciate the suggestions and comments over my first story.