First Time With A Shemale – Sexy Roop

Hi guys, I am Fayaz, from Mumbai. I am a young bisexual guy who prefers females to shemales.

Basically, I am not into guys, but chicks with dicks. I am 25 years old, with a slim body and a full beard, hairy legs but very little hair on my upper body. My circumcised dick measures a nice 8 inches and is always clean shaved. My dick curves to the left side when erect.

Anyway, enough about me. Let’s get to the story of how I fucked and got fucked by a shemale for the very first time in my life.

Well, I was always into females, but for a very long time, I had been watching shemale porn and always got excited about trying it once in my life. But after my first time, it never stopped.

It all started from a porn video I once saw when I was going through porn websites. I came across a site when I mistyped female as semale, so I just casually browsed the website. When I saw the content there, I got really hard and jerked myself off.

Pretty soon, I watched it regularly and would cum watching guys eating shemales’ cum or getting fucked and fucking them.

This went on for about two or three months, and then I decided to find a shemale to try it for myself. During my search, I came across a dating website where I found many shemale escorts in Mumbai. I browsed each and every profile and called up every profile. Everyone was charging between 2k to 6k for just two hours.

Then, I found a very safe profile under the name Roop Dutta. She was from Thane. I fixed the rate at 1.5k and decided to meet her. Which is where my journey of fun with shemales begins.

I decided to meet her on the day of Eid, 2014. On that day, I got up, prayed, and finished all my chores, and got free around one in the afternoon. Then, I called her up and arranged a fun time with her at 3 pm on the same day. I got ready and left at around 2 pm for Thane in an auto and reached the given address by 3 pm.

When I reached her address, I called her up and she guided me to her room. I won’t lie, it was a baithi chawl type area, but I felt safe because her house was at the extreme end of the chawl. When I reached her door, I went straight inside as she had left the door open for me.

It was very dark in her room as she had switched off all of the lights except one small bulb. Nothing was clearly visible. But after latching the doors, she switched on the lights and there she was, standing in front of me – a bulky, chubby lady with cute looks and a Punjabi dress on her body.

She looked the same as she did in her photo on the dating profile.  The only difference was that in the photo, her body looked very curvy, but in reality, it was not as much curvy as it was a little chubby. Anyway, she was looking very sexy.

She offered me a glass of water. I had it and sat there on her bed as she went back to the kitchen to return the glass. When she came back, she sat beside me and asked me about what I would like to do, etc.

When I told her that it was my first time, she just kept her finger on my lips and told me you want to try it for the first time, so let me do my thing, and if you don’t like it, then just stop me. I said ok and she switched on a dim bulb and came back to the bed and made me sit in between her legs and started kissing my neck.

With that first touch, I got aroused and closed my eyes. I surrendered myself to her as she was kissing me on my neck. I was caressing her thighs, and it was an amazing feeling. Her breath smelled amazing when she kissed me and her hands went inside my shirts on to my nipples.

She began pinching my nipples and playing with them. Then she slowly removed her right hand from my shirt and grabbed my face and planted a soft kiss on my lips. And then, we started kissing like we were madly in love. After about five minutes, she asked me to remove all of my clothes and she removed all of her clothes.

That was one of the most amazing things I had ever seen in my life. Her milky white body with big boobs(silicon) hanging in her purple bra. She kept her bra and panties on and asked me to keep my undies on as well. Then she pushed me onto the bed and came upon me and we started kissing again.

Slowly she went down on my nipples and started sucking them like she was a newborn. It was a heavenly feeling and then I was even more amazed at the feeling of her tight dick inside me. I could feel it very nicely and slowly as her dick just shrunk and came out of me.

Fuck, guys! That feeling was so unique and different. It felt like I was shitting and her dick automatically slid out. Then she got up and cleaned herself, and came near me again. She started kissing me, then slowly moved on to my chest and then straight on to my dick.

Fuck! What a pro sucker she was! I have never had such a blowjob again in my life. I was back in the heavens with my dick deep inside her mouth and her hands pinching my nipples. Wow, guys! I was feeling so lucky to be with her. She went on for about five minutes and then she got up.

She went and got a condom and asked me to wear it. In the meanwhile, she applied jelly inside her ass and then directly went on the bed in doggy style and asked me to fuck her.

It was difficult for me in the beginning, but she guided me. Her asshole was very tight. I went in slowly because it was hurting her due to the curvy nature of my huge eight-inch dick.

After I was fully inside, she asked me to wait for 10 seconds. Then she asked me to start it slowly. I started it at a very slow pace. Once she started moaning, I held her back and started fucking her like she was my bitch, with no mercy, as she had done to me. I did this for about five minutes and came.

I lied down on her without removing my prick. My cock came out slowly by itself after two or so minutes. She got up and cleaned herself. I did the same, then I paid her, and I left.

After this fun time, I went on to try many other shemales in Mumbai. I fucked them, and I got fucked by them. I ate their jizz.

So, if you want to read my other real-life experiences then please do like this story. I will upload my other experiences later. Love you guys!

If any shemale loved this, then just ping me at my email, [email protected]