His Sissy Randi – Part 1

Hi, Indian sex stories dot net friends, I am Ayesha, a fat, cross-dressing sissy from Chennai. Please send feedback to [email protected]! The story takes its time to build, so relax :) this is the first part, where I start with my man… The second part will have more juicy stuff ;)

It was a hot, sweaty midsummer night like always in Chennai. No matter how many times I diddled my clitty, no matter how many times I thought of being a girl, I couldn’t cum. I was sexually and mentally frustrated. Putting on a t-shirt, I went out to clear my head. I looked around and observed the faces of the people around me, “This is not my city. I shifted here a month ago. No one knows me, or my parents, or anyone from my life.” it was the perfect recipe to let loose and actually do some things which I had been too afraid to ever do in Delhi.

Somewhere in the middle, I made a decision, and now more surely, walked in one direction. I passed from in front of the shop slowly, pretending to casually look at it. There were poomex, poomer, quill form hoardings in front, and I could see scantily clad women on the boxes displayed in the front of the shop. I stopped after a few steps of overtaking the shop and turned back. I slowly entered and immediately saw the 4-5 customers spread out. There was also an old lady tending to the ladies. I asked the shopkeeper, “Anna, till what time, shop open?” and looked like I was in a hurry. He replied “9 ‘o clock”. I came out, my heart beating. I felt each breath going in and coming out. My eyes darted everywhere, making sure no one was looking at me suspiciously. I swallowed hard and walked back to my room.

At 8:50, I came out of my room again and walked to the shop and looked in. The old woman who tends to the females was just leaving and the shop owner and his boy were wrapping up merchandise. I entered and smilingly asked if he had some underwear for me. Since it was closing time, I knew no one would come in now. I pretended to look at the male underwear boxes while stealing glances at the bras and panties on sale.

I managed to select underwear for myself, and while it was being packed, I asked the shopkeeper, “Anna, bra panty for girlfriend..?” and gave a mischievous smile…

That night, high on my success, I put out an ad on locanto for my “Services” with a few pics in my new pink panties and yellow bra. I got many replies, and 4-5 seemed promising. One of them seemed fine, actually. His Hindi was good, and he seemed dirty-minded enough for me. We talked about spanking, blowjobs, and lipstick on his dick. I felt good with him. He said he had a place free, but only that night. Omg! It was 10 pm. I swallowed. I asked him how far it was from the bus stop and more questions to stall for time, but I knew if I waited, my excitement would go down and anxiety will make me say no. I soon agreed to meet that night itself!

After getting on the wrong bus and getting shouted at by the conductor, I boarded the 95 to tambaram east. He kept messaging me, asking when I’ll come. I had butterflies in my tummy from shyness.
I got down in front of Madras Christian college and was standing there with my bag with toiletries, lingerie, and some books inside in case police caught me for some reason. I could say that I was a student.

Standing there, with young boys and girls freely coming and going, I felt like a real whore for the first time, waiting for my client to come. It was so exciting, standing in the breeze, in front of a bus stand. If only I had a cigarette! I imagined being a real girl, with all the filthy bus drivers and conductors knowing what I was. They would stare at me, make lewd comments, and ask me to come with them. I would pretend to ignore them. Then I would finally give in to one who would take me to the slums and fuck me like the whore I was in the middle of the slum. If only!

My ass was itching, and my clitty was getting excited. I loved the feeling. I started to relax and enjoy the anticipation. My anxiety was under control. He was late by 20 minutes, and I pouted at him cutely. He smiled and said, “Sorry baba..Come now. Let’s go home.” I got on his scooter behind him.

He took me 4-5 kilometers away, through a maze of houses which I would not have remembered. I was totally dependent on him for coming back. Now that thought started to excite me rather than scare me. I imagined him holding my hands above my head on the bed and demanding everything from me, knowing I had no other way out. I would pretend to weakly struggle, and then give in to him, asking him to be gentle…

I snapped out of my fantasy when he slowed down in front of a gate.

We had freshened up and had the take-out Chinese he had ordered in advance. He was shirtless, and I was wearing only my lingerie for his pleasure. He was looking at me like a wolf. I was smiling softly and slowly finishing up my noodles. He switched off the tv and crawled to me on the bed. He took the fork and box out of my hands and kept it on the table. I leaned forward and met his lips in a kiss. His left hand wrapped around me, pulling me to him. The other started pressing my fat boobs through my bra. I moaned like a pornstar, both my hands on his ass, squeezing and pulling him to me. His dick kept getting harder with each press of our crotches.

He moaned when I bit his lower lip, and broke away to frantically break open my bra. I opened it for him and stuck to him again. He came down and bit my nipple, “ah! Baby slowly..I’m going nowhere”
“you’re so hot!”

I pulled his head into my breasts, and he suckled hungrily. He bit, squeezed, massaged, and groped to his heart’s content, so when I sensed him slowing down, I took charge.

I pushed him to his back on the bed and started kissing every inch of his muscled body. I tasted his nipples and felt him spasm under me. Grinning, I repeated it again. Licked, bit, and sucked his nips while caressing his dick slowly over his pajamas. He was getting impatient, so I went south. I kissed his tummy and bit a few times on his navel. Then I looked through my lashes at his face and kept my hands on his thighs. I spread his legs and took his boxers’ band in my teeth. Slowly, I pulled it down, and he lifted his hips to help. His dick sprang out and started swaying. My god! It was thick. Really thick and average length. My mouth watered.

“baby wow! Your dick is huge! Mmmmm”
“isn’t it? Chal ab jaldi choosna shuru kar”
“mmm poori raat chusungi mere raja” I said with a wink

I slowly grabbed the head with my hand, and put my nose on his hairy balls. He sighed. I rubbed his balls all over my smooth face and took out my tongue to give small licks here and there. I slowly started licking up and down his entire shaft, while looking in his eyes. As soon as I reached the head, his eyes closed and he moaned. I put my tongue in his piss hole and started sucking the head. He started writhing and put his legs on my shoulders. I adjusted the angle and took him a little deeper. His breath caught and he encouraged me to go forward. I kept running my tongue around his dick and pinching his nipples.

I started going up and down and slowly taking more and more of him in my mouth each time. His hands found my hair and entangled his fingers in it. He pulled me to him, and I didn’t resist. I tried taking him in my throat, but the gag reflex was too strong, so I just took him to my limit. He kept trying to make me go deeper, but I couldn’t so I started poking his lund into my cheek. Now I took him to the base and he was happy. He shook my head and mouth around his dick and I ran my tongue all over it like the hungry slut that I felt like.

I wanted to try something, so I came on my knees and started applying suction and going up and down. Now he really started to get excited. His moaning reached a peak, and as I took his cock head in my mouth for the last time and applied all my suction, he cried out, “bas chhosti reh randi! Fuck!!” and started cumming. A wave of pleasure ran through me as I received his hot, salty load in my mouth. I swallowed as much as I could and used the rest as lube to continue servicing him. He came down from his high and looked at me and started laughing. I looked down to see my bright pink panties soaking wet. I had soft-cum just from sucking him and hearing abuses!

We got up and he asked for some rest before he got hard again. I said ok and started looking around. His sister’s or mom’s almirah was right there, so I asked him and opened it to find some fake jewellery and make up. I smiled at him and took out the mascara, smiling naughtily. He also looked excited.
“makeup karegi?”
“haan man hai…”
“kya hua?”
“dekho ..Mujhe na..Randi banne ka shauk hai. I mean kabhi bani nhi hun but fantasy hai..Bilkul unke jaise kapde, bolna, aur makeup chahiye. Waisi galiyan sunke excited hoti hun”

His grin said it all. He was in.

This was part 1.Please tell me if you liked it at [email protected]