Crossdressing Stories

My Boss Finds Out My Secret

my boss finds out my secret

I work in an outsource management company, with more woman than man and the company has many outlet across the country.Paul is my boss who turn around each outlet every six to twelve months.

Work is very difficult, working under pressure. Paul is very straight forward at work and many staffs have bad times with him. So far, I do my work correctly in time and he appreciates it and even some time he invited me for a drink.

For me going to work was a pleasure, wearing tight jeans, shirts and always my panties with lace.No body is aware of my cross dressing.

I still remember that Friday afternoon, I went to the bathroom and few seconds later Paul came in too. We did pee and then by surprise, with a smile Paul told me to keep well my panty lace well inside my jean and went back to his office. I was really confused of what to do now as my boss just saw what I have been hiding at the office for years. I went back to my desk and told my colleague that am not feeling well and that am going to leave earlier.

Arriving at home with my confusion about what I will tell him now as he already noticed me wearing panties and that he is really harsh at work. I started getting stress and pressure my raising in my head. The office called but I didn’t rely and even on Monday morning I sent a sick message to the office.

I was taking the decision to resign from work as Paul already knows about my cross fact I was aiming for complete transformation in the years to come. But I was at a point where everything is a mess.

So I decided not to go to the office for some days and then send my resignation letter. On the next day still stressed as I am, the house and myself we’re in a mess. I heard the ring bell. I went to open the door with my sexy jean short and with my surprise, Paul my boss was at the door step.

I panicked, took a deep breath and after some minutes, I opened the door. I invited him inside, he was in a causal dress and we sat in the living room. He brought a shopping bag and was asking about my health and even told me to take some more days off. I didn’t know what to say, I went in the kitchen to bring some drinks and there I stared crying as I didn’t want any one to that at my work.

Then Paul, came to me to give me a big man hug and whispered in my ear that he likes me very much and that the bathroom incident was not an issue as he likes to love trans woman. I could understand what was going on and continue to cry in his arm.

Then after a while he brought me on the sofa and told me that he wants to give me a chance to live like I wish to and gave me the shopping bag of a sexy short jean, T shirts, black panty and a bra. He told me that he wish to live with me and to set some goals together.

But for now he wants to bring me out for a ride to relax myself and he is off for some days and kissed me unexpectedly on my lips. I was embarrassed by the move but he reassure me that it’s personal matters and even told me that he will bring me with him to the move and will support my transition as I wish.

I dressed up and he invited for a ride and was amazed looking how sexy I was in woman dress.At the door step he hugged me and gave me a harder kiss on my lips unexpectedly. I was so happy inside to live that moment but very shy from outside.

He made me ride to a remote cliff where we were able to enjoy the summer wind, then on our way back home he stopped to order Take away dinner. We had dinner at my place, he was really handsome, caring and what I really appreciated on that day was the hugs he gave me.

After dinner, we had a long discussion about myself, that I would go for transition and for gender reassignment, I want to live my live as a woman. I appreciated the talks and while sitting on the sofa, he came closely to me gave me a hug kiss , turned me around, caress my neck and continue to drag me until I can resist him.

I felt in his arm while he continue to kiss me everywhere. It was as if my dream coming true. I was roaming, exciting and feeling his body and man order. Then I removed his clothes and things goes harder and stronger.

I couldn’t stopped myself and he as well. I took his name more than a time with pleasure and eventually made him arous-ed more and more. He bent me on the sofa from the back, gently for the first time and penetrated me. Then made me sit in doggy position, shut my mouth from behind and started riding me. I was on another planet with him.

He didn’t give me time to understand, as if he also didn’t had se-x for long. Finally I gave him what he wanted a good Bl## Job and we were set exhausted. I roamed on him and sleepy.

He picked me up from the sofa and bring me to my room in his arm. We slept together..

part 2 to continue..

Story sent by Douce

Facebook Comments


  1. What a lovely story… that would be a fantasy also for me…

  2. Such a wonderful outcome of intimacy. So many reading the story are envious.

  3. Oh, how I wish I could be a loving woman for a sweet, gentle man! I want to dress femininely for him, and be caressed, hugged, and loved by him so much! Oh, YES! I simply need ma good Daddy! Why, even if he wanted me to be his wife, I would just say, “Yes, YES, YES!!!”.
    I would be such a very good Girl for my Daddy, my Man!
    Miss Roxanne

    1. Roxanne I’m your man here ❤️ I will treat you like a queen 😘😘😘😘

  4. So exciting wish for it to happen. to me.

  5. I would be too much of a chicken if my employer found out about my CDing. But I am also a different type of CDer. I don’t do the whole girly girl thing. I just wear ladies wear like a man would. Kinda like a woman who wears men’s clothing

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