Neighborhood Training

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Closet crossdresser gets caught by neighbor.
1.6k words
4.21
40.3k
18

Part 1 of the 2 part series

Updated 06/16/2023
Created 10/04/2022
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Jenny2603
Jenny2603
19 Followers

Hey everyone, This is the first story I'm writing, not just on literotica, but ever.So please enjoy and excuse my English for I'm not a Native speaker. Also leave a comment if you would like to see something in the story in future. Thanks.

This story starts when I at the age of 19 had to go stay at my neighbour's house for a month as my parents were going on vacation.

Let me tell you something about my neighbours. They were a rich family comprising of Vijay and his gorgeous wife Archana. Vijay was a businessman and was home rarely as he used to travel often. But his house was not scarce in servants who were responsible for taking care of the house in his absence.Archana herself was a boutique owner and used to design costumes.

I was very excited at the prospect of spending a month in the company of Archana but my reasons were different from what you would assume. You see, ever since I was a kid I had been intrigued by feminine clothing and accessories. It started when i was just a kid of 11 and I tried out my Sister's frock and panties. Ever since that day I hadn't stopped dressing up whenever I got the chance.

Now I had seen the types of dresses, jewellery, heels etc Archana used to wear and Oh! i could die happily if i got to try even some on.So when my mom announced that I was going to spend a month under her surveillance, my happiness knew no bounds.

Soon the day arrived. I bid farewell to my parents and with the slight packing I did, arrived at Archana's house. I knocked on the door expecting some servant to open it.

However, it was answered by some other girl who was even more beautiful than Archana. She was wearing a Crop-top and a mini-skirt and her hair was tied in a high ponytail. She smiled at me and said

"You must be Adi. We've been waiting for u. Come in"

I was still awestruck by her and only could muster up a small "Ok".

As i took some steps inside, Archana arrived, "I see you met my sister Pooja.She just graduated from her college and will be staying with me for a while.I hope you guys become friends."

Turning to Pooja she said "Pooja, Show Adi his room please while I go see if Lunch is ready."

"Ok sis" Pooja replied and asked me to follow her. By now my happiness knew no bounds as i could not only try out Archana's dresses but Pooja's as well. I truly was in a dream that i didn't want to wake up from. While i was following Pooja all that was going through my mind was how I would look in the outfit she was wearing once i got thee chance to try it.

"Here we are. This is your room and right next door is mine. I'm going to rest for a while.Lemme know if you need something.

"Thanks" I said and began dragging my sole bag into the room. It smelled flowery and sweet which i liked quite a bit.

"Oh Yeah! I forgot to tell. I was using this room before and havent cleaned out the wardrobe yet. I hope you can manage for now. I will get it cleaned out by someone as soon as possible.

It couldn't have gotten any more ideal for me. Suppressing my smile i said"No problem. I haven't brought a ton of clothes myself as my house is nearby."

She smiled and went into her room.

Till now i was hard and dripping wet and i hadn't even seen what was inside the wardrobe. I locked the door from inside and pounced upon it.

Inside it were dresses, tops, skirts, pajamas, ethnic suits and whatnot. A separate drawer had multiple items of lingerie from lace bras to padded bras and from satin panties to thongs. It also had multiple items of jewellery and make-up kits. In the bottom drawer was footwear- from Sandals to 6" high heels. She was a shoe-size Eu 39 which was 1 less than me but I knew I was definitely gonna squeeze into them. I was so excited that I felt like i was going to cream my pants.

Suddenly a knock at my door made me jolt back to my senses. "Adi, come to the dining hall. Lunch is about to be served." Archana said. I shut the wardrobe door with caution and replied" I'll be there in a minute"

I made my way towards the dining hall. Pooja was already there. The three of us had our meal together and then we returned to our rooms.

I being the horny sissy i was, couldn't wait a second before opening the wardrobe again. I decided to wear blue lingerie that looked something like this (https://bit.ly/3fA3k5B) and a white top with blue skirt (https://bit.ly/3M1tZ7a). My cock was so hard it could burst. I decided to watch some lustomic porn and jerk off before taking a nap. However i happened to fall asleep while watching porn itself. When i woke up, it was evening already. I felt wet and sticky around my croth and realized i had a wet dream.

"Great! Now I'll have to wash the panties carefully before Pooja comes back to get them.", I thought to myself. As i got up from my bed and tried to get adjusted to the dim light in the room, I was greeted by a voice "Hello beautiful. I see you slept well" followed by a flashing light and then another. It was Pooja. I was scared out of my mind and so astonished that i couldn't speak or move. She continued taking pictures as she said " I suppose you like wearing femininine clothing."

I stayed silent.

"Reply when you are asked something Adi....... or should i call you Ananya" she giggled.

I simply nodded.

"Yes.. what? You like wearing feminine clothing or I should call you Ananya or.....both?"

"I like dressing up as a girl sometimes.But please don't tell anyone about this. Not even my parents know.I'm really sorry about your clothes.It will never happen again"

"Oh nooo. On the contrary, I think you look rather cute.So cute that I'm compelled to show you to the world. That's why i have taken pics you see. Of my beautiful princess Ananya."

"No please...don't reveal my pics anywhere. I beg you."

"You beg me? I don't see any begging. Beg properly if you want me to listen. Come down here, kiss my feet and beg properly slut"

I was shocked.More shocked than when I had found out her wardrobe. More shocked than when she had caught me probably.

"Did I tell you to do something slut?"

I immediatepy got down on all fours and proceeded to kiss her feet.

"Please Pooja don't show my pics..."

"Mistress... that's what you'll address me as. Got it slut?"

i nodded.

"Please mistress don't show my pics to anyone." I kissed her feet again

She smiled and said" Alright I'll keep your secret for now. But you will be my personal slave for as long as I'm here. Or else...."

"Yes mistress. Whatever you say" I responded.All this time I was scared but not once had my cock gone soft. It was hard as a rock and leaking continuously from excitement.

"Good Girl", Pooja replied. " Now strip for mistress, Ananya"

I looked at her in surprise.

"Quick! I don't have all day" she ordered

I started to shed my or rather her clothes one by one.

"Oh my! You even wore my bra and panties. Bad girl" she said as she spanked me. "Clothes are fine but you will have your own underwear. I don't wanna catch you in my or my sister's underwear again. You understand?

I nodded.

"SAY IT" she yelled

"Yes mistress. I won't use your or Archana's underwear again."

"Good. Now strip off the underwear too."

As i lowered my panties my 4.5" dripping cock sprung out.

"OMG What's that? Its so cute" Pooja chuckled.

A gorgeous girl in her 20s was laughing at my cock. I felt humiliated but even so my cock was still excited.

"Do you like me making fun of your cock?" Pooja asked.

I lowered my head in shame.

She picked up a 6" inch heel from her wardrobe and brought it up to my cock.

"Oh god! I have walked on heels that are higher than your cock.""With that small a cock, no wonder you like dressing girly.No worries though, it's perfect for panties. From now on you will refer to it as your clit. Got it?"

"Yes mistress." I said.

"Put the underwear back on. I see you have soiled them, so you can keep them.""Also wear the top and skirt until its dinner time and NO, you may not clean yourself. Even during dinner you will wear the bra and panties. I have a lot of things planned for tomorrow so I'm going to make some preparations. Until then, goodbye slut"

she said and put her foot towards me.

I realized what I had to do and proceeded to plant a few kisses on them.

"You learn quickly slut" she said before dashing out.

I stayed there on the floor in disbelief for some time contemplating about how I was going to get her to delete my pictures. I decided to wait for an opportune moment and proceeded to watch some more porn.

Before dinner, I got changed leaving the underwear on as Mistress ordered. Pooja wasn't at the table during dinner. Upon enquiry, I found out that she was eating in her room.

After dinner i decided to sleep in just my lingerie. Thinking about what Pooja had planned for tomorrow i drifted off to sleep.

Jenny2603
Jenny2603
19 Followers
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7 Comments
AnonymousAnonymousover 1 year ago

You have us hooked

I dream of this and becoming a lesbian slave as I have no desire for cock other than a strapon getting pegged

JentvcdJentvcdover 1 year ago

Good start so far so wishes something

like this would happen to me.

JoannePareJoannePareover 1 year ago

Dear Jenny,

Lovely beginning I am very surious and eager to see what happens next , please continue and keep us interested.

Joanne

💋

AnonymousAnonymousover 1 year ago

Sounds like the beginning of some really good times, I'm bi and turned a friend gay one day at my place.

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