My name is Tanuj or Tanisha as they now call me. I’m a boy in my late teens 5’6” thin but not skinny, pretty much hairless (totally now). It all started about a couple of weeks ago. I always had a cross-dressing fetish but I was not sure if I was gay. My cousin Anisha who is a few years older t to me (we called her Ani) had come to town, she lived in a different city and was here for just a couple of days and then I was I going to go to stay with her, at her place for a week. She said she is getting bored so she was going out with few friends she had in the city.

After about 2 hours she left, I sneaked into her room and started going through her luggage and then I found her used clothes I took out the panties and started smelling them, it was sweet and sour smell. I had an erection within seconds. I took off all my clothes and wore her used bra took out a new pair of panties wore it and kept inhaling the sweet smell of her pussy from the used ones and started rubbing my dick.

In all this I failed to notice the sound of foot steps, suddenly the door opened, it was my sister, Ani di (di means sister in hindi). She was back home before I had expected. She screamed in shock and I froze for a couple of seconds then took my clothes and ran back to my room . After 10-15 minutes I heard a knock I ignored it, I knew it was her, then she started shouting and told me to open the door she said if I did not open it, she would tell my mother. I got scared and opened the door.

When I opened the door she slapped me hard right across my face then stormed inside and told to sit on the bed. I was still in a little shock and just stood there and then she shouted “SIT DOWN YOU SLUT”. I quickly sat on the bed. She threw a bag at me and said “Wear these”. I looked inside and there was a bra, panties, a t-shirt and a very short skirt. I looked at her with a surprised look on my face. She said “What ? You want to be a girl right ? Go on wear them.”

I stood up and started to go towards the washroom, she said “Where the fuck do you think you are going bitch ? Change right here”. I was even more shocked and said “But, di in front of you?”. She said “Why not ? if you can jack off in my panties while smelling the other I do not think it would a problem for you to change in front of me?” I stood there frozen and she shouted “STRIP YOU SISSY SLUT”. I started removing my clothes, as I got down to me boxers I looked at her, She said “Go on.” with a evil grin on her face. I took it off and she started giggling and said “No surprise you want to be a girl, you can never satisfy one with that tiny clitty-cock of yours, so you rather be a girl.” she kept giggling.

I started putting on the panties then the bra I noticed she had started taking picture of me and close up of my ass; she still had that grin on her face. I was getting scared this had gone to far, as I put on the t-shirt she told me to wait then she stuffed a couple of socks in my bra to make them a little more real. After I put on the t-shirt she took many pictures of me like that. I felt embarrassed and humiliated but oddly I was a little turned on by all this too. After a while I asked “Ani di can I please change now ? I’ve learned my lesson, I’m sorry.”. She said “ No way, I have a lot more planned for you my little sissy slut. Plus, judging by that little bulge in your skirt I’m pretty sure you are having a lot of fun too.”

I quickly hid my erection, she kept her camera aside and came closer and started sliding her hands and towards my dick I was yet more shocked and gasped and said

“Di this is wrong.”

She squeezed my dick and said “You are my bitch now, you will let me do whatever I want to do to you or else not only will I show those pictures to your family but post them on the net. Got it ?”

I had no choice so I nodded lightly. Her grin just became wider and it sent chills through my body.

Slowly her other hand moved to my ass she pulled my skirt and put her hand inside the panties, she started caressing my ass rubbing it, grabbing it, pinching it and the other hand just kept rubbing my dick. She went behind me and told me to bend over. Slowly she slid my panties down, and started rubbing her wet finger all over my anus, I just presumed it was her saliva. She came close to my ear and whispered “Do you like it when I play with your ass-pussy like that slut ?” looking away I said in a very low voice “No”, I lied, “Your clitty little cock says otherwise.” she said while rubbing my hard cock. She certainly getting a lot of pleasure in harassing me, but, I even I was turned on.

She whispered again “If you like me rubbing your ass-pussy, then how about this.” she suddenly pushed one of her fingers in my ass, and without wanting I let out a lowish moan, she giggled and went deeper, my lips had made an ‘O’ I certainly liked it. Slowly she started playing with my ass, circling her fingers inside moving it in and out, and all I did was lie there and kept moaning like a whore being fingered, she found my prostate and whenever she rubbed I let out a very shrill moan, my eyes were closed, and my moaning had become louder, she came closer and whispered “You just love this don’t you slut ?” I just moaned in response. She added a finger and she slid her other hand inside my t-shirt slid, inside the bra and started playing with my nipples.

My moaning was a lot louder now she started giggling now. She kept fingering me and playing with my body, at times playing with my nipples or my cock, she slapped my ass every once in a while and slowly added a third finger. In the midst of it, I never noticed when she had taken her own pants off and was now wearing a 7 inch long strap-on dildo. I didn’t notice until she pulled her fingers out and came towards my face. I was totally taken aback seeing her rubbing that huge purple latex dick. I was really scared my hardon was gone, and I kept staring at it.

She said “Go on slut, suck this cock.” I looked at her but did not respond suddenly she slapped my and pulled by my hair and shoved it inside my mouth and said “I SAID SUCK.”

I started sucking all over it. “Thats like a good little sissy slut.” she said. After a while, out of the blue she pulled out and pushed me down on the floor. Before I could react she pulled my waist up and put the dildo’s head on my anal opening. I shouted “ NO PLEASE!! NOT THA… AAAHH” she did not listen and pushed the head inside I started groaning in pain. She did not stop and kept pushing in, it was just a few inches and it felt like a foot and suddenly it rubbed over my prostate, now I was moaning in pleasure.

Slowly it was all inside my ass, she kept it like that, I stopped moaning but again had the ‘O’ shaped lips. She came closer and whispered “You like a cock up your ass-pussy?” I didn’t say anything, I was in too much pleasure, she said “Ok then I guess I should pull out.” and suddenly I shouted “NO!!”. She started laughing “Do you want it ? Do you want me to fuck your ass-pussy?” I said “Yes” in a very low voice. “Say it slut” she said. “Oh please, fuck me!” I said loudly now, “Fuck you where slut ? I want to hear you say it.” she replied, “Fuck me, fuck me hard in my ass-pussy”. She did exactly that she fucked my ass, hard, doggy-style, about a couple of minutes she flipped me over pushed my legs up in the air and apart and fucked me missionary she fucked my ass like that for about 10 minutes. All I could do was moan like a slut in heat getting the best fuck of her life.

Then without pulling out she pushed me in front of a mirror of the dressing table, I put my hands on the table. She said “Look at yourself you sissy little slut, look at your darkest fantasy come true, look at your clitty cock bouncing around”. I opened my eyes a look at myself, I was blank about how I looked, I couldn’t think about anything other than that rubber cock fucking my ass moving over my prostate, touching places I never knew existed, making me feel things I never knew I could feel.

It had been about half an hour since my sister was fucking me now, I could feel she was getting tired, I knew this was about to end, but, she had one last trick up her sleeve. I heard a click and the dildo started to vibrate in me, that sent me off the edge, I moaned out loud and started cumming, I came a lot, but even after spurting my semen I kept having dry orgasms, little shivers keep going through all over my body starting from my anal sphincter. I kept moaning. That continued to what seemed like eternity. Now my sister switched off the vibrator and pulled the dildo out of my ass. As she let me go I fell in the puddle of my own cum.

She came near my face and said “Clean this cock slut, suck the cock which went up your asspussy.” I was too weak to respond, she forced me up and pushed it down my throat. I licked it clean. She pulled out and let go off me. I fell back down. She walked away I kept lying there I realised that not even once I tried to push her off. Maybe I was a slut, maybe wanted a good fucking, right in my ass-pussy.

Since after that my sister fucked me with that dildo 5-6 times, made me cum just by getting fucked at least 5-6 times, I was a slut now, within 2 days she had made me a sissy little slut who likes sucking dick and getting fucked in her ass-pussy, and even cums by just that.The night before leaving she told me that I was going to go with her to her town for a week, she said she had talked to my mother. That night she fucked my ass-pussy and in the end told that I was going to have the best week of my life.

The next morning, when I came out of the washroom after taking a shower, I found Ani di waiting for me with a butt plug in her hand, I looked at her questioningly, she said nothing and came near me took of my towel and told me to bend over, she “plugged my ass”, the butt plug wasn’t very big or wide. She told me to dress up and I asked “but di what about the butt plug ?”, she giggled and said “ you’ll have to wear through the day”, I was taken aback, “but it’s a six hours long journey” I said, “so what ? and you aren’t wearing that” she said pointing towards my boxers “I’ve kept my panties, the ones I wore yesterday, put those on under your pants, and don’t you DARE take out that plug slut.”

I was horrified, the panties were fine but the butt plug in my ass, my dick was semi hard nonetheless, my body was defying my mind, finding pleasure from the rubber toy in my anus. The week had not even started and I was already scared of what was to come next, but a part of me was even excited to find out.

Through out the journey I couldn’t sit properly, I was walking funny and the worst part my dick was drooling pre-cum, I went to the washroom and saw that I had a huge wet patch on my panties, pre-cum was oozing out constantly. Every now-and-then when my sister got a chance she rubbed her hands all over my ass, pushing the butt plug further in, whispering in stuff my ears like “having fun slut ?” and “you like having your ass-pussy plugged up don’t you ?”. As humiliating and embarrassing as it was half way through the journey I could feel the wetness in my panties, I was scared that it might come out on to my pants, luckily that didn’t happen. At the end of the most tiring journey of my life, which with a rubber toy up my ass and a pre-cum drooling dick it felt like a lot longer than it was.

As soon as we reached home she told me take off my pants and shirt. The panties were soaked in pre-cum, she laughed seeing at and started rubbing my dick “your cock works like a clit doesn’t it ? makes you wet.” she kept rubbing my dick she slowly took off the panties and started playing with the plug, pushing it in, moving it in and out and all I did was moan like a whore I had become.

After playing like that for awhile, she told me to strip naked and pulled me into the washroom, she started going through stuff in a cabinet, she was taking out a hair removal cream, I knew what was in her mind now, “Di please not my body hair, I barely have any” I pleaded, she looked at me with anger and told me to shut up. She applied the cream all over my body and told me to take a shower and wash up. I did not have a single strand of hair below my head. It felt oddly good to have smooth skin I felt like a baby but my gaping anus reminded me that I was a slut not a baby.

As I came out, I saw a pair of pink bra and matching laced, pink satin soft panties, soft black stockings, a tank top and a very short denim skirt on the bed, there was also a note “wear these and come out and sit on the dressing table and wait for me.” Beneath all the clothes, there was a small funny shaped dildo which a little bent towards the inside, I knew what to do with it after wearing all my clothes I pulled up my skirt pushed my panties down and started putting the dildo in as soon as entered the bent end was touching my prostate I moaned out a sigh of pleasure. It rubbed my prostate with my every move I started to wet my panties again, I couldn’t walk straight, limping/walking I went and sat on the dressing table.

My sister came in dressed similarly to me, she had the evil grin on her face again, she started taking out make up, I got her intentions but didn’t question, I knew it won’t matter to her. She applied makeup on me and to top it all she put a wig on my head. She said “ This must be like a dream come true for you, dressed up like a slutty girl have a dildo up your ass-pussy pressing on your G-spot.” followed by a few giggles.

As I looked in the mirror, I was surprised I really did look like a girl, no one could actually tell I was a crossdressed, my sister had done a fine job. “ So, I guess to complete your transformation, I guess we should give you a girl’s name too… Um.. from today your name is Tanisha” she said while laughing. I was not embarrassed anymore, I had not only gotten used to this but I was now liking it.

After applying her own makeup she said “Ok lets go.” I looked at her questioningly, “Oh I forgot to mention, we are going out” she said, “like this ?” I asked, “Tanisha, nobody would even notice that you are crossdressed slutty boy” she said, her grin had again gotten wider and it again sent chills through my body, this time starting through my prostate.
We hired a cab, my sister said she had the night planned. On the way she taught me how to speak in a girly manner. The cab stopped at the one of the best 5-star hotels in town, we went straight to the bar, it was the first time I was drinking so we decided to keep it light. For about the first hour, we talked pretty much normally, nothing sexual, just how to cousins talk.

But then, out of the blue she came closer to me and in a lowish voice asked “So Tanisha, you liking the toy inside your ass-pussy rubbing all over my G-spot ?”, I blushed and shyly looked away, “you love it don’t you ? is your clitty-cock wetting your panties ?”. I didn’t respond. She took out a remote with a regulator on it and said “ let’s see what happens if I do this”. She switched it on the and the dildo started lightly vibrating. I let out a low moan, and looked at her pleadingly and said “Please di, not here”, “why not ? you like it don’t you ?” she said. I got up to go to the washroom, as soon I took my first step it started vibrating more I almost fell, I kept walking as I could, after a few steps it was vibrating even more, I couldn’t walk I took support of the wall and started moaning unwillingly, a few people around me started noticing,

I was trying to sound girly to keep some pride, the vibration increased again, “oh fuck, my ass” I said, my knees went weak and I fell down, a few more people noticed, my moaning was getting louder I tried crawling to the washroom, now it increased even more, I started moaning loudly, saying things like “oh fuck please stop this… oh my ass-pussy”, I wiggling my ass unwillingly, lying on the floor in the middle of a bar every knew something was wrong, my dick started drooling pre-cum like a faucet which was left open, I couldn’t control my body anymore but somehow my moans were sounding like a girl, like a whore getting fucked. People around me started making video, few gasping, few got grossed out and left, no one came to help.

Suddenly I felt that I was going to cum, I knew it, “oh fuck, please stop.. I’m gonna cum, no no… OH FUCK MY ASS I’M CUMMMING” I said, I started moaning loudly, I came in my panties, I came at least for a whole minute, followed by a another minute of dry orgasms. It stopped. I thanked god, I was sweating like a dog in heat, I could feel the cum flowing down my thighs soaking into my stockings. When I got back to my senses I got up and saw a huge wet stain on my skirt, I’m sure everyone was now sure of what had happened. I saw that my sister had left, I was humiliated beyond explanation, and then I got a sms on my phone from Ani di “Room 248”. Without looking at anyone I went out of the bar and towards the room.