Crossdressers First Sexual Experience

It's a Fictional story --

4 yrs back when I was a 20 year old boy I will tell about a true story which I have kept a secret for all these years now. I don't know how it all started but I am very fond of crossdressing since I was 18 years old. I enjoyed the feeling of wearing soft female garments and the feminist which stand me feels in them.. I started with my moms nighties and eventually moved on to wearing sarees (Indian Traditional Wear), with bra, and blouse,panty, bindi, bangles, lipstick and last but not the least a female wig which I had bought from a drama school that has wigs available from one of their shows.. All this I did, of-course when I was all alone as I had no guts to dress in public.

As soon as my mom and dad left for office I used to dress up elaborately and admire myself in mirror. I always had this feeling I was a female trapped inside my male body.

To give you a small outline of my looks. I am 5"7 ht just 55 kgs and waist of 28in. I am very fair and have delicate features.

I also mastered the art of cooking eventually and used to feel pleasure cooking food and snacks for myself basically it was the thrill of standing in kitchen and doing all feminine work. But I admit I never felt of having sex with a male all these years. I was very happy in my secret world enjoying the dressing all by myself. That was all about to change after my graduation exams as my elder sister who is married and settled in another city, invited me to spend my vacations with them. I was thrilled as it meant lots of privacy to dress up as my sister and brother-in-law are both working and are out of house for whole day.

I immediately told mom and dad that I am going to my sisters place for spending my vacation to which they readily agreed. I packed my bags but took care to carry only bra, panty and the long hair wig which I hid in my last rack of the bag. I reached Jaipur after a full day journey and was greeted by my brother-in-law and sister at the station. When I reached home I came to know that my sister's father-in-law was also staying at their place which made me bit nervous as to my crossdressing plans. Her father-in-law was a 55 year old man and a retired m professor from another city, who used to stay 3 months which each of his 3 sons since his wife died 10 yrs back. I greeted him and my didi, who showed me to my room and I had a quick wash and joined all for a dinner. My sister told me that her father-in-law was a jovial man and asked me to be comfortable staying with him that too in one room as he was not typical fussy man.

Next day was Monday and my sister and brother-in-law left for office. I got up late as usual and had my breakfast. Babuji as everybody referred to my sister's brother-in-law was reading a news paper. I went to him and offered him coffee which he said tasted very good and asked where I learnt to make such a good coffee.

I obviously could not tell me about my acquired culinary skills. He had the habit of going to town library at 10 am to refer research papers as he still liked to keep in touch with his scholarly side.

After he left. I decided to grab this opportunity to dress my self as soon as he left. He left after having his coffee and said he will be back for a lunch by 2 pm.

I immediately went to my sister's wardrobe and picked up a grey chiffon saree and a pink petticoat, and white blouse as I had already brought a black bra. I went to the dressing table and put on the bra which was padded and my pink satin panty, and tied my petticoat then I wore the blouse and tied the long hair wig and started draping the saree, put on a light shade pink lipstick and some foundation and didi's bangles and bindi. I looked into the mirror and there I was looking stunning as usual in my fem avatar, I did a small walk in front of mirror like ladies do by swaying my hips while walking which I had mastered by now and adjusting my saree pallu to hide my cleavage. I went to kitchen and started making aloo fritters, the very feeling of standing in saree in the kitchen and cooking was giving me goose bumps.

I happily went to the bathroom and lifted my saree and petticoat and sat down to pee as I felt dressing is incomplete without this feminine ritual. I then changed my self into my male dress as it was time for Babuji to return from the library. I hid my clothes and my sister's which I kept back in her wardrobe and washed my face well to remove any make up marks.

Babuji returned by 2 pm we had lunch and I served him those pakodas for which he praised me again for my culinary skills. He was a jovial man indeed. In the Evening Babuji and me went for a walk in the Jaipur city which Babuji explained to me about its historical significance however my eyes were on those lovely embroidered ghagra cholis in those lavish markets.

Next day again as soon Babuji left to the library I dressed my self up and sat in front of mirror admiring my curves. I started reading news paper in that dress and completely forgot the time and at around 1.30 pm I heard the opening of the gate and I came back to my senses I had to peep from the balcony to see Babuji entering the house so I ran to my room and started changing into menswear which I did in quick time but I was totally panic stricken as Babuji entered the house but thankfully I had managed to wear shorts and t shirt. When Babuji saw me he kept staring at me and I was totally nervous thinking as to why is he staring at me when I have changed. He came up to me and I asked him "Are u not feeling well Babuji?l

And my Babuji replied, beta go and see in the mirror. I went to my room and saw to my shock I had bindi and lipstick still on my face. I was shivering with fear when he entered my room and I started crying pleading him not to tell any anyone. He gave me a glass of water and made me comfortable and asked me what it was all about to which I confessed my weakness of crossdressing. He was grim at first and seeing his grimness II begged him not to disclose this secret to anyone and I promised to stop this habit once and for all.

He said "Beta I will not say anything to anyone but only on one condition. Show me by wearing the saree once in front of me."

I was shocked at this. I asked him again to not tell about this to anyone and he again agreed but I had to wear the saree once for him before that. I had no option so I told him to go to another room and wait for some time. I again dressed my self up with all the make up and saree and wig and the bangles.. I went to the drawing room and he was astonished at what he was seeing. To my amazement he smiled and said that I was looking beautiful to which I did not know whether to feel happy or not. He then asked me to sit next to him and told me its ok for me to dress like that and can do so when I am with him and when others are not there. I was thrilled by this unexpected encouragement. He then asked me to serve him lunch dressed in saree which I did and after lunch we started talking. While talking he was constantly staring at my figure and chest area in particular.

Finally he asked me how do I have breasts ... I was feeling awkward at this question to which I said it's a padded bra Babuji to which he replied "plz let me see beta" to which I did not reply. Babuji then touched my padded bra and cuddled them and he put his hands inside the blouse to feel them. First time I was touched by a man this way and I felt pleasure and the essence of being a female. Then he asked me to walk in front of him which I did but I was still shy to which he said "beta please sit next to me.." so I sat next to him he put a hand on my waist and praised my beauty. Hearing this from him I shyly replied thanks Babuji.. He was cuddling my back and feeling my bra strap when he asked since when I started cross-dressing and I said since 5 years.

He said "I can see that you have practiced this a lot." He again praised my beauty and kissed my cheeks.

When he kissed my cheeks I asked him "Babuji oh.. what are you doing..?"

He said "Don't worry darling it's my pleasure and then he started touching my boobs and I repeated "Babuji what are you doing?"

Babuji said "Nothing, I'm just caressing you a bit, don't you like it?" he asked me and I said "But Babuji .............. to which he said "Dear now that u have started wearing female dresses you are acting like a female too.. you want a man to do something sensual but still putting on a act of shyness.. Come and sit on my lap beta." He made me sit on his lap.He removed his kurta and hugged me pressing my boobs on his chest. I was getting hot now slowly and I said "Babuji what if somebody will come here?"

He said "Hey, your sister and my son will come in the evening, so don't worry, plus I will call you Nandini from today onwards and that will be your female name.

I sat on his lap and he started removing my blouse and I asked again "Babuji, what are you doing???

He replied "Beta please tell me, how are your delicate breasts?"

He started pressing my boobs on bra and I was getting hotter I said ahhhh Babuji its paining me..". He kept playing with my chest and with my waist.. I was also getting turned on by his touches.. In the heat of the moment I started cuddling him and he held my face and he planted a deep kiss on my lips biting them nicely. I responded by sucking his tongue during the kiss. Ufffffff.

Then he said "Nandini, uffff u look so beautiful. Will you let me enjoy your juicy body?"

I said "But but Babuji till today I have never done anything like this."

He said "oh dear, with me do it for the first time and experience my love."

He then unbuttoned his pyjama and released his 8 inch giant cock and I was shocked by the size. Babuji said "please hold it in ur soft hands dear." I held his thick cock and started caressing it.

Babuji said "You are caressing my cock so sensually.. ufff I am enjoying it so much" ...

I said "Babuji even at this age your cock is so big and thick.. uffff..."

He said "Oh dear it's made out of eating food with lots of desi ghee not the biscuits and whatever youth of today eat ..."

He the. pressed my head down on his cock and said "Suck my cock my darling."

. I said "Babuji i cant suck your entire cock as you have a very big cock."

.He said "No problems dear do as u like.."

I then started licking his cock head with my tongue to which he gave out a moan and then I licked his shaft and then the tip of this cock and sucked his balls.

He said "ahhhhhh Nandini you are giving me the feeling of heaven with this blowjob..".

I gulped half his cock in my mouth and started sucking his cock like a lollipop. He was moaning with pleasure and then he pushed the whole of his cock in my mouth which started gagging me. I wanted to withdraw his cock from my mouth but he was holding my wig tightly. So then I adjusted to his thick cock and started moving my tongue on his cock.

He said "Nandini ur my darling, my princess ..."

Babuji was about to cum and now I really wanted to withdraw his cock from my mouth but he did not let me go and he started ejaculating his cum in my mouth and I had to swallow his entire load.

I climbed in his lap again and asked "Babuji how did it feel and he said that it was a very good and hot blowjob.. he felt very good and he hugged me very tightly and I enjoyed being squeezed in his manly arms..

In the bedroom I lay on the bed and invited him to come on top of me. Babuji lovingly came on top of me and started kissing me madly to which I was responding affirmatively. he then took my bra off and sucked my nipples and pressing them intermittently in his mouth.

I was moaning loudly " ahhhh ohhh mmmm Babuji, please wait and your darling is in pain.

He said that "My dear Nandini on pressing them they will get bigger and u will get more n more pleasure.. for now just feel some pain."

I cooed obediently "Achha Babuji, please press my boobs, I will not let say anything ..."

Babuji's cock was again erect by the foreplay and he asked me to sit in doggy position which I did and he said "Nandini, Now be careful, I am about to fuck your ass."

I was shocked at the language of this gentleman, "ufff Babuji, I will not be able to bear such a big cock of yours"

He said "oh Nandini darling don't worry it's not my first rodeo.." and he coated his thumb with his saliva and inserted his thumb in my ass hole and I moaned in pleasure and said Babuji uff what is this mmmmm..."

He said "Your enjoying it na darling"... and started moving finger back and forth and pressing my boobs with other hand. I was enjoying the finger fuck and going crazy in lust ... he did this for 5 mins and then he wiped my ass hole with a wet cloth and started licking it like bar of ice-cream.

I was moaning " ahhhhh ohhhh Babuji I am enjoying it a lot ... and after 5 more mins of finger fuck I said "Babuji Fuck me please.. please Babuji ..."

He removed his finger and applied a wad of oil on his lund and held my ass cheeks and placed his cock in the against my ass hole and said "Darling are u ready for my cock..."

I said "Babuji mmm sure but be gentle please ..."

But he was not gentle and he shoved half of his big and thick cock in my ass and I screamed "Oh godddd Babuji it's paining me ahhhh ohhh ahhhhh please take ur cock out of my ass..." and I moved forward but his iron like grip held me back and he said "Just relax Nandini darling ... soon it will be more pleasurable.." and he pushed his thick cock further in my ass, like a bull and I almost had tears in my eyes.

" ahhhhhhhhhhhhhhhhhh Babuji its really to big.. its paining a lot.. take your cock out of my ass.. please.., I can't bear the pain.

He was in no mood to listen and he kept me aligned to the bed rest and started moving his cock in and out of my ass ... I was also moaning in a bit more pleasure now but still in pain I said " ohhh ahhh Babuji please mmm ... please ufff.. please stop ... please go slow.. ahhh mmmm yess ..."

After some time my ass muscles adjusted to his giant cock and I was feeling more and more pleasure, which he noticed and said "So Nandini darling.. its not paining now ... ur enjoying it na.."

I said "it's paining Babuji but less and less now.. ahhh ufff mmmm.

He said "uffff ur ass is so nice ... ur hole so tight.. uffff such a bubble butt u have" and he continued to ram his bulldozer like cock in my virgin ass.

Now I asked him to increase the speed and he said "uff Nandini darling u didn't say you have been itching to have your virgin ass fucked hard... uffff"

. I said that I had never known before that a scholar like you could give so much pleasure.."

He said "now u know how good I am in fucking na Darling ...

II said "yes Babuji now I understood ahhhh.."

He said "I am about to ejaculate my Nandini darling ..."

I said "Yesss cum inside my ass Babuji and make me a complete woman now ..." and soon enough Babuji started cumming deep in my ass.. this thick cum kept ejaculating for around a minute or two..

He then slumped on me and now I took him in my arms and kissed his mouth lovingly and said "Babuji u have taken my virginity today mmmmm."

He said "Oh darling you have made me young again ...I have fucked you for the first time but after today, I will fuck you every day and night. I will fuck as I make you my mistress, you will cook hot food for me and also warm my bed at night... understood my darling and he again gave me a deep kiss.. it was a deep smooch and very hot..

I said "Babuji I will do things your late wife never allowed you to do... I am yours and fully yours to enjoy.. I love you Babuji... my body is yours and only yours from today onwards..."

My asshole by now had become sore by his sordid and I told Babuji that my ass is hurting me.. he laughed and said ... "Nandini Darling.. well your walk will also change. If you do feel in pain after your ass fucking, then apply a cream on your ass hole every day twice a day and you will get relief.

When my Sister came home in the evening.. he requested my sister to let me sleep in his room every night as he might need assistance to go to toilet in the middle of night, to which my sister readily agreed as she had no clue what was the real reason for her Sasur ji insistence on that.. I too on my part insisted to my parents to let me stay another month as Babuji had decided to help me with my studies in college.

So with that permission for the two months I was at my sister's place, Babuji fucked my ass like his newly wedded wife and during afternoons I used to dress up and serve him like his dutiful wife.