Cross Dresser sex story – Sex with boss

Cross Dresser sex story

I was recently promoted to the post of Team Leader after 1 year of joining this Company. My boss, a very handsome man of 40 years old called me into his cabin one day. He told me during lunch in his cabin “Now, we are buddies, you know, my wife is going out of the town for a day. Dude, do you know any woman who is deprived of sex? I am bored with my wife, I want to enjoy with other women. Do you know any? I can pay.”

I told “Well, sir, I know few women but first of all you have to get along with them. They can’t come directly to sleep with you.”

Then he said “Ok, to tell you my secrets, I really like Sexy curvacious women and beautiful Cross dressers also. Can you arrange some one for the night? You have many contacts in this city.”

Then I said “Ok, let me try, I will ask someone to directly come at your flat.”

He told “Who? Woman or Crossdresser?”

I smiled and said “That is for you to find out.”

He smiled back and I went to my work desk for continuing my work. When I returned to my flat I was really excited about this idea. I myself am a Cross dresser and my regular readers know my story. For those visitors who have visited this site for the first time, let me tell you that I stay alone in a flat because of my Cross dressing hobby.

Whenever I am alone, I remain cross dressed. I have every stuff which a cross dresser or a lady could imagine in her wardrobe. I have breast forms, wigs, jewellery, accessories and all types of clothes. My height is 5’8 inches, I am a bit healthy and I undergo laser treatment for removal of body and facial hair. I don’t have a single trace of body hair and my skin is very smooth and shiny.

I decided to give my boss a surprise in the evening by visiting him as a Cross dresser. No one can make out that I am actually male, in fact everyone thinks that I am a Hot woman because I look so real.

I wanted to wear something sexy tonite. I went to the bathroom and started having shower. I really like to bath in the form of a woman. It gives me a very sexy feeling. My wig’s hair also gets wet but I like to dry them up like women do.
I came out of the bathroom wearing a gown. Then I wore the breast forms which I ordered from the internet. These breasts forms had U shaped breasts which were 36 in size and had dark brown nipples. The breasts matched my skin color so no one could make out that these are fake.

I went to the wardrobe area and took out a set of bra and panty. The panty was black in color and had laces. I wore the silk panty which made me feel like a young vibrant outgoing girl. I tied the panty which had laces on the sides.
Then I started wearing the bra. I carefully placed my breasts in the cups on the black bra. This bra had colorless straps. I hooked it from behind. I was so happy behaving in this way because I know how I have developed as a cross dresser.

Then I took out a blue saree with blue blouse and peticoat. I wore the petticoat first. When the petticoat’s soft silk material touched my legs and thighs, it felt great.
I tied the petticoat under my belly. Then I wore the blouse which had half arms and was a bit tight to let me show my sexy and hot clevage which any man would like to suck.It was a modern blouse and it had short sleeves. It had deep neck and back cuts.and was also a bit tight in the armpit area to make my boobs look hot.
Finally I wore the saree and made a pallu which was just enough to hide my sexy cleavage.

I didn’t wear much jewellery but applied some make up. I don’t have facial hair as I do gold facial every week. I wore blue heels sandal and carried a blue bag with me.

I called up the cab with the same driver with whom I had sex a week back. That is other part of a story, but still if you are interested then click here to read How this driver had fucked me.

I entered the cab and the driver was very happy to see me. He complimented my new avatar. Finally he drove me to the mentioned address.

I went to the 4th floor and rang the doorbell. My boss opened the door and welcomed me inside. I could speak in a feminine voice as I had been practising for the last 8 years. He couldn’t recognize that it was me. I introduced myself as Rani. His eyes had great lust in them and I could see that he was clearly deprived of sex from his wife.

We sat and had Vodka based drinks. We chatted about ourselves and he couldn’t guess whether I was a Lady or a Cross dresser. I know many of you also cannot guess. There is a photo of mine on the left and let me know how I look after dressing up.
I know you all have misunderstood me as a housewife. Same was the case with my boss. We had already taken considerable amount of Vodka.

Now both of us had started getting horny. I was so attracted to him that I started kissing him. He also responded smoothly and kissed me back. He removed his T-shirt and jeans and hugged me in his arms. We went to the bedroom and I removed my pallu of the saree. He also undraped my saree from the petticoat. We kissed again and he pressed his chest on my boobs. I removed his underwear and took out his 9 inch long dick. I started licking it from top to bottom.

I started sucking the head of his penis and tasted his pre-cum. Then I started licking his whole rod with my tongue. Slowly I took the whole dick in my mouth and started sucking it. I was rubbing his balls while sucking his penis. Just then I took his penis out of my mouth and he started fucking my mouth by taking his penis in and out of my mouth. He removed my tight blouse which had become wet from underarms. He he removed my bra and my hot 36 inch boobs sprang out towards him.

I was sucking his penis deep in my mouth. Then I took his hard rod in between my big breasts and he started fucking my breasts. Then I stood up he hugged me and kissed me.

He opened the knot of my peticoat and made it to fall to the ground. Then he asked me to sit on the bed like a bitch. I sat on the bed like my master ordered. He then removed my panty from behind. My ass was exposed to him and my hard penis also came out. Then he started rubbing my asshole from the tip of his hard penis. I was feeling like a slut waiting to be fucked. Then he started inserting his penis into my asshole and grabbed my big breasts from behind. It was painfully exciting. He slowly entered his full dick inside my ass and grabbed my breasts tight in his hands. He slowly started fucking me and I held my hard penis in one of my hands.

I was feeling great like having sex in such a hardcore manner.
He fully inserted his dick in my ass and started fucking me as hard as he could while hugging me from behind and smelling the ladies perfume from my underarm.

He fucked me hard and while he was fucking me I took my hard dick in my hand and started masturbating. Both of us were in pleasure. Just then he was about to cum, I also increased my speed of masturbation. HE cummed in my ass while fucking me, I was in pleasure as I had also taken out all my sperms from my dick. He had filled my asshole completely with his hot sperms.

Then we had sex in every possible position and we fucked for the whole night. It was such a wonderful experience that I cannot forget for the rest of my youth.