Memorable Night With A Shemale

Hello everyone, my name is Ajay Kumar and I am staying in Gachibowli, Hyderabad. A little introduction about me. I became bi-curious under different circumstances. I was later diagnosed with erectile dysfunction which made me more drawn towards the bisexual world.

I have met with guys. But always felt that something was missing which made me more curious about meeting a shemale or couples. But found out that they were next to impossible. I signed up on various websites to search for shemales or couples or females interested in owning a bottom slave.

But most of them were paid and I’m not in a position to pay. I lost all hope of meeting anyone in real time. The following story is a fictional story based on the different situations I faced during my search for people to meet. The story is a little long so bear with me till the end.

One day I was browsing through all the websites I have signed up. As usual, most of them were empty or messages from single males. Just as I was about to close it, a message popped up. It read, “Interesting profile. Ping me back if you’re interested.”

I immediately went through the profile and found that it was from a shemale. I was very happy and excited as hell. I immediately replied to her and we started talking. We shared our personal details, our likes, dislikes and all. I shared my desire to get my first anal sex with a shemale, but there was a problem.

I stay in a hostel so I can’t host and she also doesn’t have a place for a meeting. I was heartbroken by listening to those words. She suggested that if I’m ok with it we can try outdoor sex. I was ready to say yes to anything just to have sex with her. So we fixed a date.

She said she will pick me up from a specific spot from my hostel. The date we fixed to meet was 2 days away. I was literally jumping from inside with excitement. Finally, the day of the meeting came. I was waiting at the place for her to show up.

While I was waiting for her to show up, many thoughts were going on in my mind. What if she was not really a Trans but just a cross-dresser or just a male pretending to be a Trans and so on. I was now nervous about meeting her. Finally, she messaged me that she arrived and shared her car number.

I searched for it and found it parked about 100 meters from me. I was moving at a very slow pace as I was nervous and was scared now to open the door. I gathered all my courage and opened the passenger door and shocked to the core. There sat a beautiful lady in the driver seat.

Anyone would mistake her for a lady. There were no bounds to my happiness. As soon as I sat she hugged me and told me not to be nervous and she will take good care of me. We started our journey towards the outskirts of the city. We were talking to each other and became very comfortable.

We traveled for about 1 and a half hour or 2 hours and the roads were almost deserted. She turned the car into an empty road and stopped at a very secluded place. As soon as she stopped, there was a kind of silence between us. I was too nervous to talk or make a move.

She understood this and placed her hands on my thighs. That sent shivers through my body. She started talking to me and ran her hand on my face, cheeks, lips, and through my hair. All of this has a different effect on me. Slowly, she took my face into her hands and took my face near hers.

A shock ran through my body as soon as our lips met. We kissed like there is no tomorrow. She took my hands and placed them on her breasts. Her breasts were big and very soft. I was crushing her boobs with my hands. She started to kiss me with more passion.

Slowly, she started caressing my back and made her way to my ass cheeks. She was groping my ass over the jeans while kissing me, I was lost in the abyss with her actions. We stayed in that position for a long time. After we broke the kiss and settled down in our seats we were taking heavy breaths like we just ran a marathon.

We looked at each other and burst into laughter. Now, she removed her top in a jiffy. I buried my face between her enormous breasts without wasting a second. I was licking and kissing her cleavage while pressing her boobs. She was moaning and held my head tight against her breasts.

After a few minutes into this, I could sense her hands going down towards my ass and increased my speed. She slid her hand through my jeans and underwear and ran her hands across my bare ass cheeks. After pressing my ass cheeks for a while she slid her hand into my ass crack and started rubbing near my asshole.

That made me stop my licking session. I started to feel different sensations inside me. Unknowingly, I started rubbing myself against her hand. She took my face with her other hand and started to kiss me again. We broke the kiss after some time but she didn’t stop rubbing my asshole.

Now I was in a different trance. Without wasting another second I immediately buried my face in her crotch area. Then for the strangest reason, I started to sniff her there like a dog. She stopped rubbing my asshole, reclined her seat and in a jiffy removed her leggings and panty.

Her cock stood up proud and my mouth was watering looking at it. Even before she could say anything I pounced on her cock as though my life depended on it. I licked her cock from tip to base, kissed it, sucked it, and took her balls in my mouth. I was literally worshiping her cock and balls.

She took my head in her hands and made me go deeper on her cock. I was gagging but I was not willing to stop sucking it. Her pre-cum tasted like the best erotic chocolate in this whole world. I wasn’t gonna let that go to waste. I kept sucking her like that for about 20 or 30 minutes while she was nearing her climax.

I could sense her cock pulsating in my mouth. I increased my speed. Finally, in a minute or so she reached her orgasm. She filled my mouth with her sweet nectar. I never swallow cum but I was completely mesmerized by her.  I swallowed her load without a second thought.

After she recovered from her orgasm, she kissed me on my lips. She said that it’s my turn to be pleasured. She got down from the car and made her way towards the boot. After searching for something in her boot, she came back towards my side of the car.

She opened the door and told me to get into the back seat of the car and lie with my back on the seat. I followed her instructions like a kid and lay on the backseat exactly as she told me to. She removed my jeans and underwear in a single go and asked me to remove my t-shirt.

She poured something from a bottle onto her hands and came towards me. She started to kiss me and put her hand inside my ass crack. I jerked a bit as her hands were cold. She rubbed around my anal hole for a while to make me comfy and slowly started to put her finger inside my asshole.

With great difficulty, she finally put her finger inside my ass. It was a feeling that can never be explained in words. I was being crushed under a beautiful and sexy Trans lady and she has her finger inside my ass. She kept her finger there for some time and started to move it in and out.

I wanted to moan like a little girl but my moans were muffled by her kiss. While finger fucking me like this for a few moments she tried to add another finger into my ass. While she was trying to do that, I could feel a little pain and a burning sensation near my asshole.

I tried to stay as calm as possible. Finally, with some effort, she got her 2 fingers inside my ass. Trust me when I say this, it feels different to have a finger stuck in your ass. But it’s a whole lot different feeling having 2 fingers up your ass (i.e., if you’re a virgin).

She started the finger fuck again and was increasing and decreasing her speed while doing so. After a few moments, she stopped kissing me and exited the car. She made me sleep on the seat in such a way that my ass was on the edge of the seat. Then she told me to put my legs near my chest.

My ass was accessible to her without any obstacle. She took the bottle and poured some liquid on to her hands. This is where I figured that it is a kind of lubricant. She took some applied near my asshole and started finger fucking me again. In each stroke, she was putting her fingers deep in my ass.

While pulling she was twisting her hand. These strokes were making me mad and I was moaning like a street whore with pleasure. While doing so, she put her third finger in. Although it stung a bit, I was so lost in the pleasure I was experiencing that I barely felt it.

She was finger fucking me and I could sense my orgasm building. Within seconds, I reached my orgasm and was jumping all over from my orgasm tremors. I reached my climax without ever touching my cock. I cummed a huge load which fell all over my body.

After I recovered from it, we looked at each other and she came forward to kiss me. Suddenly there was a loud thud on our car which brought us back to reality. I panicked and immediately hid between the space between the front row and second row of seats. She got in and lay on the seat.

We were buck naked and couldn’t even reach for our clothes. Then I heard a female voice asking us to come out if we want to avoid getting into trouble. We had no choice but to exit the vehicle and do as we are told. At first, I thought it was just some lady who lives nearby.

We thought that we will convince her somehow and leave without creating many problems. But, as soon as we exited the car and looked at her, my heart dropped into my stomach. She was no ordinary lady. She was a lady police constable who was on her way home and came in our direction as she heard a cry.

Then I realized the mistake I made by letting out that loud moan when I reached my orgasm. I was standing facing her with my hands covering my cock. My Trans friend stood in such a way that her ass was towards the constable. She immediately started asking us all types of questions like who are we, what are we doing here at that time and so on.

We were answering her and she asked my Trans friend to show her face. With no choice, she turned to face the police constable. As soon as she turned, the constable’s eyes popped out and her jaw dropped watching a cock on a girl. After gaining her composure she asked my Trans friend whether she was OK and why she was crying before.

Then we explained to her clearly what happened exactly. We assured her that it was me who she heard not my Trans friend. She just could not believe what she was looking at and hearing. Then we requested her to let us go and not to make this a scene.

She agreed to let the matter go but she was curious to know what we would do next. So she wanted to watch what happens next and then only she will leave us. Otherwise, she said she will arrest us. I was very excited by the idea of being watched while having my ass fucked. Who wouldn’t?

Then my Trans friend made me suck her cock to make it hard again. It had become soft due to all that’s happening. I started sucking her and the police constable was watching us without blinking her eyes. I was sucking her cock and she was pressing her boobs.

This clearly had an effect on the constable and she started to touch herself. This encouraged us more. Finally, her cock was rock hard and she was ready to assault my asshole. She took a condom from the glove box and wore it. She poured some lube on my asshole just to make it easier.

My Trans friend then made me bend on the backseat and started to put her cock inside my ass. I could feel her cock pushing against my hole. The lube was helping to an extent but not all the way through. She started to apply pressure and slowly her cock head is making its way inside my ass.

I could feel a burning sensation followed by a sharp pain around my ass. The pain gradually increased and I jumped forward to avoid the cock. My Trans friend called the constable for a little help and she happily agreed. She came towards the other end of the backseat and held me there.

Now she started to push her cock inside again. I could feel a lot of pain but I could not escape from it this time. After a lot of effort, she finally got her cock head inside me. Tears were rolling from my eyes and I was asking her to take it out as it was burning me from inside.

She removed it and after some time she tried to enter again. But this time she didn’t go slowly, with one powerful stroke she was completely inside me. I was about to shout but before I could do so the constable lady closed my mouth tightly. My ass was feeling like it has been ripped into two.

I was crying like a little girl. After keeping her cock inside me for a while, she started to fuck me slowly. Now my pain was almost gone and I could feel the pleasure. After a few more strokes, I got used to the pain and started moaning from the ass fuck.

My Trans friend and the lady constable laughed at me and made remarks that I’m a true whore. Then my Trans friend encouraged the police constable to have fun while enjoying the show. She immediately removed her pants and buried my face into her pussy just as if she was waiting for this word.

Her pussy was hairy and smelly. But I had no choice but to lick it as I don’t want to piss this lady constable off. I could taste urine, sweat, and pre-cum from her pussy. She was rubbing my face on her pussy making my face completely drenched in her pre-cum. My Trans friend was also busy pounding my ass.

After about 30 minutes of all this, the constable finally said that she also needs a cock in her pussy and asked my Trans friend to fuck her. My Trans friend was more than happy to do so. She removed her cock from my ass. I felt like somebody removed a body part.

She entered the constable in a single go as it was well lubricated with her pre-cum and my licking. They were fucking and I was standing outside the car with a gaping asshole feeling empty. After fucking for a few minutes, they changed their position.

Now my Trans friend was lying on the seat and the constable was riding her in cowgirl position. Then my Trans friend calls me and asked me to lick the constable’s ass. I was really startled by this and didn’t move as I didn’t want to lick her ass. Then the constable said to do as I’m told or I’ll be in trouble.

With no choice, I bent on my knees on the ground and started licking her ass. Her ass tasted very foul from sweat, but I had to lick her. As she was moving constantly it made it a bigger task to lick her. Finally, she reached her orgasm and got down. My Trans friend was yet to reach her orgasm.

So she called me to ride her in reverse cowgirl position. While I was riding the constable was playing with my nipples, pinching them and so on. With all the fucking and nipple play I was nearing my climax and so did my Trans friend. We both climaxed at the same time.

I fell backward towards her. She hugged me and we stayed in that position for a while. Finally, we got the energy back, came out of the car to find the lady constable all set to leave. She took both our numbers and left on her Moped. We found our clothes, got dressed and left from there.

On the way back we were making plans for the next time. My destination had arrived and I had to leave. She hugged me one final time and kissed me before saying goodbye. I got down the car and went into my hostel had a bath and slept happily thinking about all that’s happened.

So that’s the story of how I met a shemale and how things took an interesting turn. Hope you liked it. Excuse me for the grammatical errors and sorry if the story was a bit lengthy.

Any couples (or) shemales (or) females near Gachibowli, Hyderabad want me as their submissive bottom slave do ping me on Google hangouts at [email protected]. Males, please don’t even message me. I’m not into males and won’t even read your text.