Crossdressing Adventures With Shemale Teacher

I am Abhishek. Since childhood, I have been little feminine in nature, for which I have even been bullied sometimes. I have been blessed with really soft, smooth and fair body, with not a single trace of hair on my body and face. I have a slim and athletic body, and if you saw me from back, you might mistake me for a teenage girl. This incident that I am about to narrate, happened when I was studying in class 12, with my teacher whom I always thought was female until that rainy day in July.

Disha madam was our physics teacher in school, and 5 of us student also use to go to her home for private tuition. We were alll 18 and above at the time. She was in her mid-thirties, a little healthy and curvy figure. Her hips were really wide and boobs real firm, big and round. I have no idea about her boob size but they looked quite big. She was wheatish complexion but her eyes and lips were amazing, and everyone including me just thought of her as a normal female teacher. Some guys from class even had crush on her but I never had any inappropriate thoughts about her. I really liked her for the way she taught in class, always cheerfully addressing everyone.

So it was Monday, in the month of July. I came back from school, and around 7 o clock in evening, got ready and left for the physics tuition with my cycle. But, in the midway heavy rain started falling accompanied by lightning and strong winds.

Due to lack of any shelter I got drenched. Anyhow, I managed to reach disha mam flat and rang the bell. Disha mam wasnt married and lived alone. She opened the door, but she was in another avatar, not the traditional disha mam who always wears sari or salwar kameez. She was wearing green half top, that exposed her belly and a hot pant exposing her smooth chocolatey legs. I noticed she wasnt even wearing a bra, as I could see nipple perking in the top. Disha mam was surprised to see me,

She said ” abishek, why are you here in this heavy rain, no one came and I doubt that anybody is going to come”. Then she looked at me from top to bottom and asked me to come in.

I said “No mam, I better get home then”

She replied, “Are you kidding, in this rain, looks like the sky is about to burst open, get in.”

Without any more debating, I entered in her flat and noticed a glass and an open bottle of whiskey. She has been drinking. She went in another room and came out with a towel. She handed me the towel and asked me to go to the bathroom and get dry. I went inside her bathroom, removed all my wet clothes and started drying myself with the towel.

I was rubbing my wet hairs, with the towel when I noticed a few sets of bra and panties on the floor. They looked really gorgeous and expensive. I picked the bra, it was really smooth and padded and behind it was written 34c. Then I inspected the panties and smelled it, wow. It had a strange aroma, intoxicating and also had white stench mark. I was smelling them when disha madam knocked at the door.

She said ” abishek, are you dry.”

I replied “Yes mam”

She said, “Listen, I dont have anything for you to wear, but I found something that you can wear until the rain stops”. I just slightly opened the door and took the clothes that disha mam handed me. When I saw what she gave me, I was shocked. She gave me a stringed panty, the one that you tie on both ends and a satin sleeveless red colored thigh length gown nighty. A thousand different thoughts ran through my mind about why she gave me such things to wear, but in the end, my innocent young mind at that time though she has no boys dress and that I dont catch a cold she gave me another dress to wear.

So I decided to wear what she gave me. I wore the panty. The silky material was doing a strange thing as my dick started tingling, and I liked it. Then I wore the red night gown. When I wore it, I discovered that it had netted back, which showed my fairy back. As it was just short thigh length nighty, my fair, hairless and smooth legs were all exposed. I tied my shoulder length hair in a ponytail and looked myself in the mirror. I was looking like a girl but without boobs. The red colour was making me look fairer, and the short length of the dress was making me look sexy. And after a lot of dilemmas, I decided to go out. I came in the drawing room, where I found disha man still drinking. She heard my footsteps and looked at me, and from her facial expressions, I can tell she was pleasantly surprised.

Disha mam kept looking at me, as I went and sat near her. She started complimenting on how gorgeous I was looking. I dont know why I was liking the feeling of a girls cloth on my skin, and why I kept blushing on those compliments. Disha mam, kept on adjusting her hot pants, as men do to adjust their cock. Then the talks drifted to whether I had any girlfriend or not, to which I replied no.

The satin silk was so smooth that it kept constantly slipping from my thighs and the panties which I was wearing kept on getting exposed. Disha mams eyes kept going there quite a few times. And then it finally happened, the nighty again slipped, and as I was about to adjust it back, disha mam kept her warm hands on my thighs. I looked at her hand and then at her face, she had a smile on her face. I was nervous, but the calmness and smile on her face assured me. She started caressing my thighs. It really was giving a strange sensation as my cock started twitching in my panties.

She brought her chair closer to me, and put her other hand on my shoulder assuring me with words, saying that its ok and there is nothing to be afraid of. I was feeling like a girl helpless about the situation. She untied the knot of my robe, which fugly exposed my bare chest and the hardon that I was having inside the panties. She twitched my nipples and that was more than enough, my 6 inch cock burst open from the side of panties. Disha mam started giggling on seeing this. I was very embarrassed, but disha mam brought her hand and touched my cock. Electric current ran through my whole body and without any control I started moaning. She started stroking my cock. Maybe she had stroked my cock 5 or 6 times I sputtered cum heavily. My white thick liquid was all over my panty, my chest, even on disha madams hand. Disha madam smiled and she licked the cum that were on her hand very seductively. The rain was still hard and little did I knew the experience was about to get more horny.

Disha madam asked me to call home and tell my mother I was at her house safe and would return when the rain stopped. I did it. She held my hand and took me to her bedroom saying, I needed cleaning. She made me stand in front of the mirror and removed my robe and panty. I was whole nude in front of her. She cleaned me with a towel. I was awestruck, not uttering a single word but just enjoying what was happening with me. She made me sit on a tool in front of the mirror. Mam said, “Abhishek its time to make you more beautiful than a girl, is it ok with you, its going to be our little secret “, to which I just nodded my head.

She took out a hair ironing machine and ironed my straight hair into beautiful curls. Then she took me away from the mirror and started doing makeup. I was not sure what was happening, but after 40 minutes when I again saw myself in the mirror, I was shocked. The reflection in the mirror was of a beautiful teenage girl and not me. Disha mam now opened her wardrobe and took out clothes. I was completely nude all this time. She herself made me wear stocking first then a violet lingerie. She put a small white towel in the padded bra and now no can tell that I was a boy. I was looking like a sweet teen girl, I was blushing seeing myself in the mirror. Disha madam hugged me tightly, and that was the first time, I felt the poke of her dick. I looked at her bewildered.

She said, ” now that you look like a girl, its time to act like one”.
I was still confused, but then she unbuttoned and unzipped her pants and sprang out a cock just like mine. Well, not quite like mine, it was more chocolate colored and bigger than me, way bigger than me. Before that day, I had watched a couple of shemale porn, but never had imagined to be with one. I was still in shock coming to my senses, when disha madam took my hands and guided it to her cock. I was now stroking my shemale physics teacher cock as our lips met for the first time. I was afraid but the pleasure of stroking a cock was just way too much.

When our lips finally after 5 minutes broke the lock, disha mam pushed me down on my knees, and I knew what I had to do. I was afraid, as I had never done this thing, but before I could utter a word, she brought her cock close to my mouth and without any warning just pushed it into my mouth. Initially, I was gagged for breath, but then I dont know how I started doing it naturally, I was loving doing it. I was getting hard on just by sucking her cock. Disha mam even told me that I was natural at it. I was sucking her smooth chocolatey cock and was groping her ass with my hand as mam started moaning now. Occasionally, I was sucking her balls also.

After some time, she made stand up and she took out my cock from the panty, and before I knew we were rubbing our cocks against each other. She removed her top, as I saw her boobs books for the first time. She guided my hands on her boobs and I started caressing it and underneath our cock play continued. After caressing her boobs, I started sucking her nipples with my tongue. I was giving them love bites. Her cock was on top of mine, and we started moving out hips to and fro doing cock fuck.

Then she pushed me on bed. As I lied on the bed, she took out a tube of lube line from one of the drawer and joined me in bed. She turned me, making me sit in doggy position and applied a whole lot of lube on my ass. I was shivering in pleasure. She first inserted a finger in my ass as I let out a soft moan. I was really enjoying my ass getting fingered. Then after couple of minute I felt something more hard and big trying to push in. I looked back and saw disha mam trying to insert her cock inside me.

I told her mam not to do it, but she assured me she will do it slowly and I wont feel pain. She slowly inserted her whole cock in my ass. Omg, I was in a lot of pain, but horniness was just too much to back out. She started slowly doing my ass, my mouth was wide open in pleasure. She held my hips, and was gradually increasing her speed. After some time, I was having no pain and was enjoying getting fucked. Disha mam was also now enjoying more, as she started slapping my ass. After 10 minutes of fucking like that we changed position. This time we reversed our role. I was now fucking her wide open ass. Her asshole was more bigger than me. Next we moved to the sofas, where I sat on disha madams lap, her cock inside me. I was jumping on her lap. We tried a lot of position that whole night as the rain just wont stop that night. I spent the whole night at her house.

When we were done, I realised the pain in my ass, and couldnt even sir properly for 1 week. Needless to say, we had a lot of fun for 1 more year until I left my hometown, for further studies. When I came back, found disha mam married to another guy, and we never had sex again.

The end

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