Losing my virginity

I'm a 21 year old attractive crossdresser from Mumbai, India. I am sharing a true story of how my
roommate turned into a permanent fuck buddy!
I've been crossdressing for 10 yrs now and have my own collection of all kinds of stuff you can think
of. I moved into the city 2 years back and rented an apartment with a guy called Vishal who I didn't
know at the time.
The first few days went in unpacking and setting up my room and trying to build a decent rapport with
Vishal, have some drinks once a while etc. The guy was around 6 ft high and well built and pretty
good looking. I used to go weak in my knees whenever he used to touch me.
Im 5'7, very slim for a guy and I wax my whole body all the time, so it's easy for me to get into my girly
personality called 'Riya' whenever I want. After a couple of weeks of moving in, I finally got the time to
become Riya when my roomie was out for a couple of days. So, on a bright Saturday morning, I woke
up, spread out all my girly stuff and chose the best outfit for the weekend. I went lacy black on the
lingerie, with a 34D very slutty bra and a black lacy hipster near my love hole.
I then put on short waist length sleeveless velvetty blue top and and a white flowy miniskirt. Since I
used to always wax my body once a while, my body was looking silky as ever, especially my legs, so
I took out my anklet and wore it on both the legs. I also accessorized myself with some traditional
Indian bangles and necklaces to make me feel really feminine.
Finally I wore long blue earrings under my sporty-looking wig and did some basic makeup with
special attention to my eyes! I looked at myself in the mirror and I couldn't stop smiling ! I had a hard
on looking at myself!
The day went by normally, I spent most of the time in front of the webcam, helping some horny boys
jerk off online. Many of them were desperate to meet me, but I was still a virgin and scared of meeting
a guy in real, although the thought of being someones bitch in bed was very very arousing. Finallyaround 10 pm, I switched off the lights and went to sleep in the same outfit with my room's door open.
It's around 11.30 pm and someone is stroking my legs in the dark. I suddenly open my eyes and
notice a well built guy caressing my legs all over with his hand and massaging his manhood through
his pants.
I am aroused but scared. The moment I get thoughts of someone raping me, I get more aroused than
scared.
I finally gather the courage to get up. The guy holds me tight and asks me to not move.
He whispers into my ears "You are my bitch tonight, whether you like it or not!"
"Vishal, is that you?" I reply in a trembling voice.
"Yes sweety, I knew you would dress up real nice for me," he said.
"What? You knew that I dress up like girls?"
"Yes, honey. I just wanted to take you by surprise, I was right in the next building all day, waiting for
my slut to finish her day and start mine!" he said, leaving me shocked.
Before I could say or do anything, he pushed me into the bed and came on top, holding my hands
behind my head and planting his wet tongue into my mouth.
My heart was racing, my feminine instincts had completely taken over me and I could do nothing but
be the slut I am, I kissed the guy back with the same passion (It was the first time I ever kissed a guy,
I was still a virgin at the time). My wet mouth was turning him on so much, I could notice his bulge
digging deep into my thighs through his pants.
He continued exploring my wet mouth for a few more minutes before he got up, threw off his shirt and
pants, looked at me like an animal for a few seconds and went back to kissing his bitch. This time one
of his hands was squeezing my ass cheeks,occasionallycaressing my love hole. I was completely
taken over and was enjoying being dominated by a rough guy like this.
I had two questions on my mind - 1. What if he forces me to suck his cock? I have never done it
before, wonder how that would be? and 2. What if he wants to fuck me? Whoa, what if his cock his
huge? Im a fucking virgin!
The kissing and fondling went on and my neck, hands and thighs were already covered with hissweat. He suddenly got up and removed his underwear and there it was! It was nothing less than an
8 incher! I was so scared I felt like running away from the room.
"Do you want to smell it baby?" he said.
"Umm... listen Vishal, I'm just a crossdresser, I've never done all this. Can we please stop here?"
"Haha, you're funny, come on, don't waste time."
"No seriously, I'm a virgin, I've never even kissed a guy before, and now you're asking me to ... you
know."
"Shut up you bitch."
He held my head and forced his rod into my mouth and I started immediately gagging.
"Take it bitch."
I somehow decided that the best way to not get manhandled is to do what he says. So I gathered
myself and started licking the tip of his cock. It was salty and I could smell all the precum and again,
being the girl that I am, it turned me on.
For the next 15 minutess, I was sucking him like a professional porn star. Infact, I was trying to
prolong the blowjob because I had no intention of taking the 8 incher into my hole tonight! So, I just
wanted him to cum as soon as possible.
But no, this guy was a monster, the 15 minute blowjob was just an appetizer. He wanted to fuck me
alright! And fuck me hard!
He took his gigantic cock out of my mouth and asked me to lie down with my legs wide open. My
heart was racing, I had no energy to refuse as I knew he would rape me anyway! I closed my eyes,
he applied some warm lube on my hole and came on top.
He started kissing me, it was feeling good until he started penetrating into my hole. The first thrust
was the most painful. I screamed out of pain and that turned him on!
He took 4-5 more thrusts to enter me properly and I couldn't stop moaning out of pain and he loved
hearing me scream! Once he was completely in, he fucked me so hard! He fucked me for the next 20
minutes. For the first 10 minutes, I was moaning out of pain, while the next 10 minutes, I was
moaning our of pleasure.Here I was, lying on my bed, dressed in a slutty outfit, with my legs spread wide open for a huge guy
with a huge cock thrusting me hard for 20 minutes while he held my hands behind my head. The pain
and the pleasure was too much for me, I was constantly very loud and noisy. I started biting my
hands, sometimes biting the pillow to control my noise.
And finally he came.
He came inside me.
He came inside this hot bitch he had conquered tonight and did he come a lot or what. I felt so
pregnant when he came so much inside me!
This was one night to remember. And as expected, this was not the only night.

My Mistake

Hi all back with a story after a long time,
This Hemanth who became Hema.
Am a boy aged 26 working in a software company. Am very lean, smooth body, no hair at all, looks like a girl if I wear girls dress. I don't know it is luck or bad luck to posses the features of a girl.
One day I was supposed to go to my flat where I stay alone. On that night I was totally drunken. So by mistake I entered D-Block instead of B-Block. Because all the flats and blocks are designed similarly. I just went to the flat and tried to opened it. It was opened. No one locked it. As I was drunken I went straight to the bedroom. There I saw a beautiful in her 20's changing her dress. She was so beautiful. I became harden. I want to sex with her. I called her, hey baby looking sexy. She quickly ran to the front door and locked it. She again ran to the dining table and arranged drinks and came to me hugged me. I was so excited. I kept my hand at the place of her vagina and i found a cock there. I was shock. She was only wearing towel. She is having good boobs but don't know why this cock. I slapped her for trying to do such a sex. She said am sorry. Please at least give a company for drink. I said OK. She wore a T-shirt and a denim short. We sat for drink. We started drinking much and much until I fell unconscious. I woke up by 11 AM. I saw her sitting in front of me wearing my clothes. I asked why are you wearing my clothes. She gave a silly answer because you are wearing my clothes.

I just stood up and ran to the mirror. I was wearing a blue coloured silk saree, 3/4 sleeve blouse, and its back open added only two threads. She added some ear rings, she placed a nice wig which make me look girls with the addition of the makeup and all. She placed a watch on my right hand.
I got lots of angry and went to her to beat. Suddenly she took her mobile and shown me some pics of me which I never expect. I was in shock and she started saying what have happen last night.
After heavy drunk she took me to the bathroom and did a nice bath for me by applying turmeric powder and brought me to the bedroom and put in a bra and panty on me and she inserted her cock in my mouth. I don't know I sucked it. She is having those pics and she even fucked me. She is have those too. She at last spouted her sperm on my face and later took a bath again and she dressed me in this saree and left me for sleep.

I begged her to delete those pics. She said some conditions. She said me to go out in this saree and all to buy some vegetables & fruits, and some staff from the supermarket. I was tensed. She gave her scooty keys and pushed me out from the flat with a handbag.
Now am starting for shopping. Actually am feeling very happy to show my inside girl to this outer world. But if I feel happy infront of her she will punish me more. So I just behaved like that.
It's 1PM, lets go out and have some in this city and kill the heart of some guys............

Akash to Asha

My name is akash, and she to some reasons I changed my name to ASHA.
Let explain.
I was an orphan. No father, no mother, no brother, no any relation. Am alone in this world. My schooling and education took part in a orphanage school. There is a request from our school that those who completed their studies and got a job they have to contribute some amount of money to the school, so that the orphans can have everything without any problem in the school.
In my childhood am not good at studies. And am a mischievous boy and my behavior likes to be a girl because I think I was having the suspects of my mom. One day I saw a girl in our school wearing a frock, its very nice, I stolen it and went to the terrace at night time and worn it and felt like I should wear only girls dresses. But I thought no one will accept me for that. So I kept myself calm. But from that I never tried to cut my hair and even I used to apply turmeric powder on my body while bathing. So I won't get any hair to grow on my body.
At the age of 24 I found that our school is not getting enough funs for the kids to have food even. So I thought of it. But am still studying because of lack of knowledge.
Let me describe about me at the age of 24, am very chubby, looking cute, fat, strong and long hair upto my hip. Even I pierced my ears. If I wore some female dress I will look like a hot aunt because I have flesh at my chest which will look like boobs.
I decided to help them because the school is the only thing I have on the earth for me. So I thought to do something. My mind ran I many directions for earning money. Suddenly one day I saw a beautiful women standing beside the road. I was observing her keenly. After sometime two boys and gave het RS 10000 and took her on the bike. I followed them and I saw they are doing sex with her. Suddenly I felt into shock that the beautiful girl is a boy. I ran to the internet centre and searched about it and came to know many things. So I decided to do sex like that and earn money for them. So I asked a teacher in our school that I want to talk with her for some help. We went to the library and sat beside her and asked her can I have some clothes of yours. She asked the reason. I took a deep breath and said those are for me. She was shocked and asked the reason. I explained her everything.
She asked me to come her house this Sunday so that she can give a good chance for me and the problem of these school also can be solved.
I asked her to tell now, she said wait upto Sunday.
I waited for the day and Sunday came. I went to her home. She invited me inside and asked me to sit. I was bit nervous. She brought tea and we had. She took me to the bed room and asked me to have a bath. I had a warm bath and came out. She asked me to stay nude. I said her I can't. She dragged the towel which I wore and saw me from top to bottom and considered that am ready for the transformation.
She gave a pink panty and a pink bra and helped me wearing it. Later she gave me a pink coloured petticoat and I wore the blouse and she wrapped me a pink saree. She added some jewellery on me and ear rings as my ears are pierced. She comb my hair and made it a single pleat and added a light make up with lipstick and bindi and kajal.
She took me infront of the big mirror in the hall and I saw some beautiful girl there. I was shocked to look at my beauty. I was looking like a hot bitch ready for getting fucked.
Then we sat on the sofa and she started explaining me. She said that she know a rich guy in his 35's and he like crossdressers very much. He was very rich and willing to maintain a crossy as his partner. I asked the reason for why he was thinking to get a sissy rather than a girl. She said it is true that you sissy guys looks after the partner with lots of love rather than us. I was in a questioned state.
I asked her what is the plan. She said we will go to his house. What you have to do is just attract him with your beauty. He will give how much money you want. So that you can help our school. I said OK and started to his house. We reached the house. She asked to stay me back in the garden. Mean while she will bring him here and will introduce to me. I said OK.
I was with full of tension. After some 5 mins they came. She came to me and took to him and introduced me to him as ASHA and she left. He was seeing at me with a puzzle. He asked me are you sissy or female. I said sissy in a husky voice. He caught my hand I ran to a tree. He came there running. We played some hide and seek game for some time. After I got tired and took up my saree and petticoat and wrapped it like a lungi. He again fan to me. I bend down due to thirsty. He saw my hot boobs. He fell in me. I was tensed. Then after he started doing sex with me. We laid on the grass there and he lowered his pant and removes his T-shirt. Oh my got he is having six pack and his cock his nearly 10 inches. I became so horny. I said him I was so thirsty. He smiled and took my mouth near to his cock and inserted his cock into my mouth. He slowly removed my saree. Then he made sit in a doggy style and lowered my petticoat and started to fuck my ass. I felt hell as he is fucking hard. He caught my hair from the back and fucking me like a hell. I shouted with pain. He ever pressed my boobs harder in the mean time. I was running out of control as its paining hard. But I want to satisfy him. After an hour of hard fucking, he took me into his hands and taken me into the house and asked me to have a bath. I had my bath and wrapped a towel upto my boobs and a towel to cover my long hair. He gave me a transparent frock to wear. He was wearing a underwear and a T-shirt. I was running into fear. He sat beside me and took me on his lap and rubbing my lips and pressing boobs, and took my hand to his cock and am pumping it. He started asking me what do you want, am ready to give anything for you. I said the problem. He said we will adopt it and you can be the care taker, But I wanted you to be with me like this the whole life. I thought for a while and said OK. He said that's my baby, now get rigid of your thirsty. I just kneeled and took his cock into my mouth and sucked it for 10 mins. He spouted out hot sperm. I drank it. I said am too thirsty. So he pissed on me and I even drank his piss.

He felt very happy of me and gave me lots of money and got a flat, car and all girl clothes. I started looking after the school. And in the evening after my rich husband.
At last people forget my real name and all started calling me as ASHA.
I was very thankful to the teacher. So we both started staying in the same flat. I sometimes makes sex with her as a girl and later with my husband.
Enjoying both sexual life parallel.
Don't know what my future will. But thinking this is my destiny to do good for them and sacrifice my life for that good..

Deepa

This is the incident which was happened in my life. This is due to the disaster or sad. But this made me changed my mind set happy.
This is yours Dileep, the real and true name of DEEPA. Let me tell you what happened in my life to get addicted to Crossdressing.
When am studying my BSc I fell in love with a girl. Her name is Rohini. She is very beautiful. She is of 5.7 height and strong. Am of 5.8 height, strong and fair. I felt for her in my first sight. They way she talks made me crazy. We became good friends just in a little time. But I was unable to propose her. In the mean while one day I saw her with a boy who is my senior. They are kissing each other. I felt very sad and went on crying. I went to her for convening that he is not perfect match for her as he was a flirty guy. But she doesn't listen at my words. So I left her on her way. After finishing my BSc I joined MBA. There I found a girl Anusha. I again felt in love. But this I didn't took it serious. We just maintained as friends. In our second year of my MBA I got a message from Rohini that she is going to marry another person and she pleased me to attend the marriage. I saw the same message in Anusha'S inbox. I was shocked. I asked her how you know Rohini. She said they are friends since childhood. I said all the things happened in BSc. She felt pity on me. I went out with sad and thought to drink alcohol. Anusha came along with me, but I haven't observed her. I took two full bottles of vodka. Anusha came to me and said return those bottles, its not good for you. I said I can't, I want to drink. Then Anu said its OK you can drink but not in your flat, drink my flat, so that I can feel you are safe. I thought for a while and said OK. We went to her flat. I said her not to disturb me and asked her to sleep in the bedroom and don't come to the hall. She said OK. I started drinking. Usually when I drink inside I used to be nude. So I did the same thing here. I removed all my clothes and sat on the dining table and started drinking. By midnight I finished the two bottles and tried to get something to eat from the fridge. In the mean time I was collapsed. I was in unconscious stage. By the morning when I woke up I was on the bed and I saw Anusha did her bath and getting ready. She is combing her hair. Anu having very long and thick hair which beats her buts. Actually I like such hair. I went to Anusha and asked her can I help you in combing your hair. She was surprised and even laughing. I didn't think of that. She gave me the comb and I started combing her hair and tied in a single pleat with a puf falling on her face. She praised me for making her look beautiful. Then she said to have a brush we can have Tea. I said OK. She went with a crazy smile. I went to the wash room for fresh up. I took the brush and started to clean my teeth. After brushing am cleaning my lips, some red colour is coming from my lips. I saw into the mirror and shocked. I was wearing a sleeveless nity of Anu. Even I was having earrings, bangles, bindi, lipstick and my face is shaved so clean. Am just looking like a girl with short hair. I ran to her and asked why you did this to me. She said first have the Tea and take bath, become fresh, we will sit and talk on this.
I took my tea and had bath and came back by wearing a towel. She came to me and gave me a patiyala salwar to wear. I said her I want my clothes back as am not comfortable in this clothes. But ANU said I promise you will become happy please wear this. I accepted her and wore it.
The whole day I was in the same dress and in the night I wanted went to the cupboard and took a satin frock which is a nity and wore it and came to ANU, this was not excepted by her. She jump with joy and said we will try something else more on this. I felt excited about the future what going to be happen. She took me to the dressing table & applied light makeup and added some bangles, payal. Later she brought a wig of hair with a length which touches my hips. She placed it on my head and and adjusted it very fine. I was just looking like a girl. No one can mistake me for a boy. So we tried to test on my attire. So we planned to go out for dinner by wearing this. So I drove the Scotty and went to a restaurant where all people mistaken me for girl. We got confidence.
The next day she explained me the plan. She said we will be attending the marriage. But you should be as a girl. So that you can attract the bridegroom and can stop the marriage. I accepted it, because ROHINI was still trying to make me cry, so lets make her cry.
We went to the marriage. The day before the marriage there was a sangeeth. So we planned to attract the bridegroom. So we got full heavy work sarees. ANU took the blue one and she gave a pink one and said pink suits for girls to attract boys. She made me wear the saree. All went on casual. This time again I wore the bangles, the same wig, ear rings, payal, chain, bindi, lipstick, and all other makeup. This made me look beautiful and hot. We went to the sangeeth. ANU took me to ROHINI and introduced me as DEEPA. And said am dumb. At the same time she gave a kind look and the bridegroom gave a lust look. So we got confidence that our plan will work. The music started, all are dancing. I went close to the bridegroom(RAJ). I started dancing with him. He suddenly placed his hand in my hips. I just slowly ran from there. He came on my back up to a room which was back side of the house and no one was there. Actually it is a store room. He pushed me into the room and locked the door from inside. He tan to me like a hungry lion and he begged me to fuck him. I was shocked by listening at his words. He explained everything that he was a gay and he is getting this marriage on the force of his parents and he never like girls. I gave signals then why u are on my back. Then he said I know you are a boy and you are here to stop the marriage. I was shocked. I just took him into my arms and felt pity of him but happy at the situation to ROHINI. So I said him I can't fuck you but I can help you later. Then he expressions changed. He became angry and said, OK but you are a girl as of now and am a guy.. We are @ a closed area. So lets do this. I was in a shock. He dragged my hair and thrown me onto the ground. He removed all his clothes. His cock was so long with 9 inch. I was shocked. He started slapping me. He gave me a deep lipkiss. I was unable to breath even. He removed my pallu and squeezed the flesh @ my Breast. He slowly made me nude, removed all my clothes and started beating me. He made me kneel down and tied my hands and legs with ropes and kept his 9 inch cock in my mouth and fucked it for 10 minutes. And then he started slapping on my ass. Suddenly he inserted in my ass hole and fucked very harder even blood came from it. He raped me for nearly 1 hour. And at last he raised a word, loads of thanks DEEPA. I was in a confusion, he said from now am not willing to get fucked am ready to fuck. Because the forced sex which I did to you made me more horny than the gay sex I did. I was shocked and felt unconscious. When I woke up I was in a hospital which ANU took me and appointed me. She felt very bad of that and pleased me for the things happen. I just said her nothing will happen as we expected.
I get relieved from the hospital after a month. Then the same day ANU made the proposal for marriage with her and she asked to be dressed as a girl whenever @ home and can have a happy life with no egos and quarrels.
So I accepted her and now we are having a happy life with no barriers.......
Thanks to my life.
Guys some are true but I added some ingredients to make the story spicy........����������

MIL

i was engaged in crossdressing from the age of 11 and always wanted to wear saree .my friend aakash's mother wore very good saree. so i made a plan for wearing that,i made a fake id and started saying her that it will be benificial for her children.i said that take one of your son's friend also for crossdressing Finally the day came there was 1 month holiday and my family and aakash family except his mother were out of the station.And i was with he and his mother in their big house. At the first day she said that you should do something new in this holiday and for that i will have an idea .she waxed our bodies told us how to put makeup and wearing saree after doing that she said that now u both are my bahus till i want. She kept my name mamta and aakash name aakanshi then told us how to be like a housewife i was engoying cery much in her saree and doing the household work and reacting like bahus. The next day morning we woke up at 5 am .i touched her feet and she said "sada suhagan raho" u always be married i became shy then she said who is your suhag (husband ) jokingly i too said your son and she said aakash to remove his saree .bra and everything to wear his male clothes and a beautiful sherwani then she took me to a separate room and gave me a beautiful red bridal lehnga and matching acessories and said me to wear that.then she took us both in the hall.we were dressed like dulha dulhan (bridegroom ) than her mother gave her mangalsutra and sindoor and said to tie mangalsutra on my neck and put sindoor on my forehead he was shocked to listen this but her mother said it will be fun to have a wife who will swrve you all time and also you can take revenge from her (me) for any fight and will get to romance a beautiful girl i became shy. He then do this and then i touched his feet than her mother left me in a separate room and said me this is my suhaagraat and i sat on the bed like that only after some time aakash came but he romanced with me for some time and he was stunned with my beauty and said i love u mamta than the whole day we were romancing .next day i woke up early did all the work till that time aakash g and sasuma were woke up i made tea for us .then her mother said to aakash that u arr now married and should know ypur responsibility and will go to one of your father's shop for work.after he went i prepared the lunch and did other works than one of his employ came to take his lunch i then serve sasu maa she was happy with me and said it would have been so good if you woyld be my bahu afterwards also ,i said i also want to this she understood what i was trying to say and said you will only be my bahu and i will make you a real girl after you complete your studies i thanked her we chatted for some time than aakash g came and we went for dinner he romanced with me there i said i am a boy but he didn't stop .the same routine was thwre everyday and i was very happy in those sarees living my dream of becoming housewife .at the second last of day of this routine at night he said me that i am in love with you and want to spend my life with u i also said that i too want to do so then he had sex with me in the night at the last day i wore her best saree and was looking like going to a party she gave me her kangan which her MIL gave her .after that i went to my home we were than boyfriend girlfriend and spent our time together some time we had sex also .after my studies complete i requested my parents to make me a girl by surgery and after some problems they agreed than my parents kept proposal of the marriage of me and aakash g for which his family (except his mother )agreed after some time finally our marriage day came i wore the same red.lehnga anf he wore the same sherwani we were very happy he tied me same long mangalsutra and put sindoor on my forehead than we took seven rounds around fire .than on the day of suhaagraat he fucked me the whole night. In the morning i was there in the kitchen with my mil and her two devrani i was the eldest bahu of the family but the youngest there we all four married ladies (me,my MIL,and aakash g' two chachi)engoy very much and share our sarees i now had better collection of sarrlees than my MIL now i have a big family or sasural (me and aakash g my MIL AND FIL two chacha and chachi ,2 SIL nanand ) and i happily