Sissified Ch. 01

It was some weeks after my 18th birthday I came home from school, nothing out of the ordinary. I used my key to unlock the front door, my mom was standing there with an angry look on her face. Let me tell you more about me and my family first, my name is Ron, I was a skinny kid from childhood and got constantly bullied, not good at sports and even worse in studies, due to these I didn't have any luck with girls and was still a virgin. I had somehow managed to get to high school, but this year it was getting pretty difficult for me to pass. Esme, My mother on the other hand was The CEO of a law firm and made quite a good amount of money, she was very beautiful with a good figure due to her regular exercises and healthy eating, she managed to raise me and make a good career after my father walked out on us when I was a year old, So I didn't give her much trouble growing up as she already faced a hard time.

Now back to my story, when I saw her angry, I asked what was wrong, she replied "Ron, how were your grades the last test". I remembered I had failed so I had hidden them "Did she find the" I thought to myself.

"What test, Mom?"

"Don't lie Ron, I know you failed your, teacher Ms. Robin called she said you had failed every test this year."

"Shit, Ms. Robin called."

"Yes, and she wants to meet us tomorrow be ready at 8."

Rest of the evening passed with I had dinner and went to my room thinking what was going to happen tomorrow, I got into my bed and tried to sleep but the suspense was not letting me sleep, so I got up and started browsing for porn on my computer, due to the stress of meeting Ms. Robin tomorrow nothing turned me on, after 30 mins or so I found a category called "Sissy", I had never seen those videos and got curious. I clicked on it and played a the first video, There was a small skinny man who gets called into his boss's office, the boss, a beautiful lady, tells him he has caused a massive loss to the company and has been fired and also has to pay a massive amount of money as fine, the man says he will do anything to get out of the situation , his boss asks him to strip then applies make up on him, makes him wear a wig ,then a bra ,panty and a cute dress ,then gives her heels .He looks like a real woman now ,then she starts fingering his ass ,stretches it ,the she wears a strap on dildo and starts pegging her. By this I was rock hard, even though at full length my penis was about 3.5 inches, I was stroking hard and had an orgasm, the best one of my life.

"Is it gay to be turned on by a cross-dresser?" I thought to myself as I drifted into sleep.

I woke up early next morning, showered then got dressed. Went down to have breakfast which mother had already prepared, as I ate beside my mother, I could sense she was still disappointed with me.

"Sorry mom I was scared so I hid it from you."

"You have nothing to be scared of, I asked to tell me any problem you have without hesitation."

"Sorry mom I will honest with you from now on."

"Good now get in the car, let's go meet your teacher."

We went to my school. As I entered the classroom, I saw my teacher sitting in the room alone. She was around 30, single and hot as hell. She had been my fantasy for some time now.

"Good morning Ms. Robin." I said.

"Good morning Ron this must be your mother, nice to meet you"

"Nice to meet you too Ms. Robin" Mom said with a smile.

"Now as you know Ron has been failing all his papers this year, if he continues to do this for the rest of the year, he will be failing the class."

My mom shot an angry look on me.

"Is there any way to get him to pass?" Mom asked.

"Well if he manages to get at least 80% on rest of his papers he could still pass but it's very difficult as the new chapters require good knowledge of the previous chapters, and by judging his marks I am sure Ron is good at them."

"Can you help him learn them?" Mom inquired.

"I'm very busy as I have other classes and I don't have much free time; besides it is a lot of chapters to cover, and it's impossible to cover them in such short time." Ms. Robin replied.

"Please Ms. Robin I really want to pass, I will study really hard, Please." I begged.

"As I said, I don't have free time at school but I Could help you if I had some extra time after school."

"You mean private tutoring?" Mom asked.

"Yes, if that's okay with you." Ms. Robin said.

"Yes please." Mom replied.

"Ok then, I will come by your house this evening and we can discuss further there."

"Thank you." Mom and I said as we left the classroom.

I thought about it on the way home me and Ms. Robin in my room, it started to look like one of my fantasies.

I got home cleaned my room and waited for Ms. Robin to arrive, she arrived around 7 P.M, I greeted her at the door, I called my Mom.

"Ok Ron, I will help you but you have to agree to do all the things I tell you." Ms. Robin said.

"He will don't worry." replied my mother.

I nodded in approval.

"Ok then let's go to your room and get started" Ms. Robin said.

We went to my room she started teaching me from the scratch, I listened to her attentively and understood the topic completely, then she gave me homework and left.

After she left I went down to get Dinner, after that I went to bed but couldn't sleep, I went back to my computer and searched "Sissy" browsed some more videos and masturbated, then went to sleep.

It became my daily routine wake up, go to school, come home, do Ms. Robin's homework, wait till the evening study with her, masturbate to "Sissy" porn and sleep. After a month or so I was browsing through Sissy porn and saw a video titled "Sissification pt.1", I clicked on it, it was a 5-part series, it said use it with a headphone, as it started playing, I got into a trance and continued staring into it, when the video ended, I had already jerked and it had been 2 hours. When I went to sleep that night, I had a weird dream, I saw I was wearing a panty and a bra and sucking a cock, I looked very girly in that dream. I woke up I realized I had cummed in my sleep. It was around 4 A.M, mom usually woke up at 7 A.M. so I was safe, I went to the bathroom put my underwear in laundry, there I saw a pink frilly panty in the basket, it was mom's. I turned to leave but something inside me told to take the panty, I tried to resist but I gave in and took them to my room, I smelled it and got horny and started jerking off, but couldn't get hard. Then I had a thought of wearing them, I got naked and slipped them on, they were so soft, I really enjoyed wearing them I fitted quite nicely in them, slowly my penis started getting hard I masturbated imagining the sissy porn I had seen and then I had the most powerful orgasm I ever had. I climbed into my bed fell asleep instantly.

I woke up the next morning and remembered what had happened, but I couldn't forget the soft feeling of the panties and wanted to try them on again, I put the pink panties in laundry. Summer break began today. Mom had already left for work. I completed the homework Ms. Robin had given me but I couldn't concentrate as the panty never left my mind. I still had around 4 hours before Ms. Robin came. So, I went to my room and searched for "Sissification pt.2" and played it while wearing headphones. Again, I went into a trance, half way through the video it asked me to wear a panty if I wanted to completely enjoy the video. So, I went to Mom's room picked up a black panty from a drawer in which she kept her old clothes which she didn't wear, came back to my room stripped and wore the black lacy panty and continued the video, after the video ended, I took off my headphones and I heard a loud banging on the door, I quickly got dressed and ran to open it, Ms. Robin was standing there she had been there for 15 min, I made an excuse that I was in the bathroom. We went to my room she entered first, when got in I saw her looking into my computer I went near then I realized I had forgotten to close the browser, she looked at the video then went into my browsing history she saw all the videos I had watched over the past few days. Then she turned to me and said, "I didn't know you were into these."

I was scared I couldn't talk, "I don't k-know about th-these." I said.

"Oh, you can be honest with me I have no problem with you watching these as long as they don't affect your studies and don't worry, I won't tell about this to your mom, now tell me." She said.

I felt relieved, "Well I been seeing them for quite some time now and I really like them."

"What do you like exactly?" she asked.

"Well, I like seeing then dress up, get make up, look girls and stuff like that." I replied.

"Wow, ok then let's get to studying."

She asked for the home work, I gave her the notebook she checked them and looked up angrily.

"I think this has started affecting your studies, all your answers are wrong. I think I have to talk about this with your mother, and I will be telling her everything." she said angrily pointing towards the computer.

"No, Ms. Robin please no, don't tell my mother about this." I begged.

"Well, we can handle it within ourselves."

"I will do anything." I said crying.

"As you know to if someone wants to eat healthy, he is forced to eat junk till the moment he vomits on the sight of those, similarly to stop you from watching these videos we have to first make you embrace them completely to the point you start hating them." She explained.

I couldn't understand anything she said but decided to comply to her instructions.

"Ok Ms. Robin."

"Great." She said happily," now I will give you some tasks to do everyday for the rest of the summer break, and I want you to do them all, if you miss even one of the tasks your mother will know about everything."

"Yes Ms. Robin."

"Oh, a sissy like you must be treated accordingly I want you to call me Mistress from now on"

"I am not a sissy Ms. Robin." I replied.

She slapped me hard across my face. "You are a sissy and call me Mistress." She said angrily.

"Yes Mistress." I replied.

"Now let's begin"

She taught me a new chapter. At the end of the class she said, "From tomorrow you will start wearing panties everyday at all times, I might call you at any time to check, Ok."

I nodded my head.

"Good I will see you tomorrow."

She starts leaving, then she stopped.

"I almost forgot as I'm your mistress you will be kissing my shoes as good bye."

I stood there still. She darted towards me pushed me to my knees.

"Kiss!" she ordered.

I gave up and kissed them.

"Good, don't you dare disobey me next time."

She left.

I stood there wondering what was going to happen next.

To be continued…