Caught Crossdressing by Aunt Sharon
- 3 years ago
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Hi readers, this is Sarfaraz Khan back with another story. Hope you remember me. If you haven’t read , you are missing many things, kindly give a read. I’m a 23-year-old male from a South Indian city. I love sex, which is smooth and seductive, never forced. So coming straight to the story
It is about my slutty elementary school teacher. Her name was Sharon. Let me describe her here. Back in school days, she was a darling of everyone’s eyes and a sure eye candy for all staff, including peons, chaprasis, and male teachers. There were rumors of her having some chakkar with our Math sir, Raheem.
But those were all rumors among us. She was very similar in dressing and style like actress Sushmita Sen in ‘Main Hoon Na’. She had the perfect hourglass figure a perfect 34-26-34 if I’m right, like a model. Aged about 27-28 at that time married to a moron older uncle who by no means could have satisfied her.
So coming to the incident. I was in a mall at the billing queue when I saw a familiar face in the front. I immediately remembered her as my teacher Sharon. She hadn’t changed a bit in 10-12 years. My gosh! I think she hadn’t put on a single extra kilo.
Her dressing sense, too, hadn’t changed with the usual stringed blouse and saree below the waist, showing her deep white navel. My dick actually flicked a bit, seeing her. She was alone, and I greeted her from behind.
Me: Hi mam, I hope you remember your student.
Sharon: Hey Sarfaraz, how can I forget my most naughty yet smarty student. How are you?
I invited her to a nearby coffee house to talk for a while. She told her husband is working in the States for the last 7 years. Her son, too, is studying in Delhi, and she is living with her mother in the same city.
I saw this as a chance to get close to her and maybe bang my crush too. I was sitting opposite her on the table, sipping coffee. I shared her about my job and everything. When I told her that I’m single, she gave a thoughtful glance.
Sharon: Sarfaraz, when are you planning to get married?
Me: Mam, why? Do I look old?
Sharon: Not like that, but a beautiful dream girl must be waiting for you.
Me: Mam, I don’t believe in all these dream girls and all. Whatever comes, let’s enjoy life. And mam, since this is a perfect one to meet, one thing I’ll say now if you don’t mind.
I said looking at her directly in her kajal eyes
Me: You were my biggest crush back in school. Not only mine, but you were also everybody’s crush.
Sharon: Ahem Ahem. Do you fantasize about your school teacher?
Me: What’s the harm mam if she’s hot?
This time I glanced at her open, inviting cleavage with a thin silver chain hanging between the valley. She caught me and covered her cleavage but giving a naughty smile. I continued flirting with her.
It was almost 2 hours, and we lost track of time. Finally, I asked her out for dinner, saying there’s an offer for couples in so and so restaurant.
Sharon: So we are couples now? Huh?
Me: What’s wrong in assuming, mam? A young guy and a sexy lady can’t be couples?
Sharon: Ahem ahem, I think you are crossing the limit.
Me: Mam, what’s the harm in it?
She finally agreed. We drove straight to the hotel. It was more of a resort-type with outdoor dining. We introduced ourselves to the manager as a couple, and he smiled at us. We were given a table near the wall with full privacy.
Food arrived, and she was shy like a bride every time the waiter told us to enjoy while keeping the dishes. Finally, after dinner, she wanted wine. I ordered for her, and soon she was 4 pegs down.
She was getting bolder and bolder now, holding my hands looking at my abs and praising my body. (You know this property of wine). Finally, I took up courage and asked can I book a room for tonight. She nodded shyly. She called up her mom and told some reason.
I called the manager and told him we needed a private room. He arranged and gave us the key. As soon as we entered, she hugged me from behind while closing the door. I turned around and directly went for her lips – what a juicy pair of lips they were.
We began sucking each other’s tongue for about 15 minutes until we became breathless. Sharon now slid down her pallu. Her lacy blouse was barely sufficient and showed almost 40% of her upper boobs. I wasted no time and began biting and licking the cleavage of my teacher.
She held me by my head, pressing more onto her. I made red marks with my teeth on her flawless white skin. Now I began opening her blouse and red lacy bra, and soon her treasure was out in the open. What a perfect pair of tits.
If anyone looks at the pic of her boobs, they will confuse it for a 19-20-year-old girl. Her nipples were still light brown, and her boobs not at all saggy. I began sucking her nipples like chocolate and bit her nipple in between.
She began putting her hand inside my zipper now and started playing with my 7.5-inch length while we continued kissing. Now she pushed me into bed and began undressing her remaining clothes. Her matching red lacy panty already had a wet patch of cum.
Her pussy was an absolute wonder. I mean, it was more beautiful than a young girl. Clean shaved and the perfect thickness of lips. She came on top of me like a hungry tigress and began unbuttoning my shirt. She began kissing my abs and biting my nipples while I played with her smooth ass.
We now shifted to 69 position. She was an excellent sucker and was undisturbed by her pussy, leaving out juices. I licked her as deep as my tongue went more focussed on her clitoris and making her squirt. She gave out a huge amount of juices, and I licked it clean.
My cock was rock hard now, ready to enter my teacher. She guided me holding my circumcised smooth cock to her pink pussy. As soon as I entered, I was on cloud nine. Her pussy was so tightly engulfing my cock like someone giving a perfect blowjob.
Her moist pussy and my stone-hard cock made the fuck like a knife enters butter. I was holding her waist, and she was holding my bums for support. I began banging Sharon like a now.
“Ahhh Sarfaraz, fuck me. Fuck your teacher like nobody before. Make me your slut.”
She widened herself as far as possible while her nails dug into my back with ecstasy. Soon I was reaching orgasm. I increased my pace while my thighs were hitting hers and making a noise. Soon my balls began boiling and close to cum. I withdrew my dick and splashed all my cum on her boobs.
My teacher was looking all sexy with the cum, naked. We slept hugging each other. We had another couple of sessions. She revealed that her husband hasn’t cared to fuck her for the last 8 years. I told her I’ll always be there for her. We dressed up and left in the morning
So girls and guys. Hope you enjoyed reading it. Show your support by your likes and also mail me with your comments, opinion, and experience. Genuine girls from India interested in any help about sex can mail me without hesitation. Goodbye, all.
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Hey, everyone, this is Rahul from kerala.I’ve been a regular reader of Indian Sex Stories since my school days.As I didn’t have any interesting experience, I couldn’t write any sex story here. But recently I had an encounter that made me think of sharing the experience on this platform.This is an absolutely real life experience and there is no drama here unlike other stories. First of all, I would like to describe myself.I am 19 years old and is 5.10″ and having an athletic body, not too slim...
I woke up the next morning still dressed in all my clothes. Had a boner in my pantyhose so i took care of that first. The sun was shining thru the window, and onto my hosed legs. Loved how the sun was warming my pantyhose legs. I loved how they looked. I wanked while i arched my feet in the air. Didn't take long for me to cum. Thinking back on the last few days. Mmmm felt so good. I heard a knock on the door. I hide my cock away and pulled my dress down and sat on the edge of my bed. “Come in”...
Hello readers, this is Sammy again. I would like to start by thanking you all for the amazing and loving feedback that I have received from my previous stories. Also, I love the amazing chats filled with kinks from my female readers. This incident happened to me in October 2020. I was shopping in one of the big supermarkets in the mall when I saw a lady from behind. I loved how she was swaying her bigger-than-average ass while going through the stuff in the aisle. As she was calling the little...
Hi, this is Praveer, from coastal Karnataka, Udupi. I am 6 ft in height and have a muscular body. I’m 20 year old, have good sized dick enough to satisfy any woman. The heroine of this story is my high school teacher. Her name is Shobha (name changed), her height is around 5.5,her body measurement which she told me later was 38-34-40. She was around 45 year old and she almost looks like porn star Anastasia Lux, having the same kind of body. Now coming to the story, one day I went to town to...
Hello friends this is a story received from my dear friend from Mumbai with a request to publish it on ISS with his name and his mother’s name changed. Let me tell you the story is true with name changed to protect the real identity. My friend’s name is Kapil Sagar and his mom’s name is Prema Manjula. if you liked it please send your comments to or or or to encourage me to write the further story. Hello friends I am Kapil Sagar from Navi mumbai. I am 20 yrs old now and studying in...
IncestWhen I think back and recall all the trouble I went through to seduce and take Sharon, my neighbor Jerry’s wife, to bed, I shake my head and wonder how blind I was not to see the big picture. Not that I did not enjoy making love to Sharon. I still do, in spite of everything that happened since that first time and the whole scene, blurred in the beginning, came into focus with a bang, literally, one sunny afternoon. But I must first write about the seduction, of which I am quite proud of before...
It is Saturday afternoon and you are just finishing your neighbor's lawn. My dad says since I am 18 that I have to pull my own weight so I mow the lawn of my 40 year old neighbor Sharon. Sharon is of great interest to me becuas she is about 5'10, about 135lbs, 32c breasts, a perfectly slim and trim body, with brunette hair. But even better is her daughter Kim, the object of most of my fantasies. Kim is 20 years old, but decided to put off college for a few years and live at home with a basic...
THE STORY OF SHARON CANE.................. I AM SHARON CANE, A 18YR OLD TRANSVESTITE SCHOOLGIRL WHO DUE TO MY BAD BEHAVIOUR HAVE BEEN SENT TO MANY REFORM SCHOOLS, OF WHICH EVEN WITH FREQUENT FIRM DISCIPLINE HAVE BEEN EXPELLED FROM MOST OF THEM FOR MY DIRTY WANKING HABIT. MOST OF THE SCHOOLS I ATTENDED WERE BOARDING SCHOOLS WHERE I MET OTHER TRANSVESTITE GIRLS & WAS INTRODUCED TO FULL TRANSVESTITE SEX BY OLDER GIRSLS. WHAT USED TO MAKE ME WANK SO MUCH?... JUST THE SHEER JOY OF BEING DRESSED...
Mistress Sharon Director Christian Feminization Academy [address redacted] [address redacted] [address redacted] Dear Mistress Sharon, My name is not important, but I want only to be Stephie. Please consider me for a position in your next intake into the Christian Feminization Academy. I have not been a good Christian up until now, in fact I have really not been a Christian at all, but I promise you that I will be the very best Christian woman that I can be if you will show...