It all started in 2016 when I was in college. I signed up for a trip to Rajasthan. We went in a bus and during the whole trip, the driver stopped the bus at a roadside dhaba around midnight.
So I, with some other guys, got down from the bus only to find a couple of shemales getting their food packed. I don’t know what happened, but I got an instant hard-on looking at them. I immediately started fantasizing about them taking me away and having their way with me. I subdued my thoughts for the time being and got on the bus, but they still kept popping up till I reached Jaipur.
After the trip, I began watching shemale porn and started reading sex stories about them. In the meantime, an old friend of mine came to meet me, and we started talking about sex. He told me about his experiences with prostitutes and also about a time when he took a pen and inserted it inside his asshole while masturbating. I showed disgust at this but was intrigued to try it myself. So I too started to use a pencil or pen and insert it in my asshole while masturbating, and it did give me a substantial amount of pleasure. I tried some other things like a board marker or a cucumber after that. I also started looking for shemale prostitutes online and used to masturbate thinking about them.
A couple of years went by like this, and eventually, I stopped putting things in my asshole.
Cut to the year 2024. It had been a long time since I tried something anal. I did have straight sex, though, but one night when I returned home drunk from a colleague’s birthday party, I suddenly had the urge to have sex with a shemale. I never had the guts to contact any of them, but that night, in the drunken state, I messaged one of them and fixed a meeting for the next day. The next day, when I woke up, I decided to try this experience anyway. So I went to their place, and the meeting started.
They were very polite, and we had the exchange of money soon. I had only one request: do not wear any makeup, and they were happy to remove it. After that, they told me to undress and undressed themselves. I told them that this is my first time and that I want them to cum in my mouth. They understood and started the session.
We started kissing, and I was quick to get their tongue and start sucking on it like crazy. I started to lick their face and caress their neck. Then I moved to the boobs. They were natural and soft. I sucked hard on the nipples, biting them every few seconds. After some time, I started to go down on them, and there it was. A six-inch cock, shaved and perfectly clean. I kissed it and started sucking it slowly. I increased my speed as I got the hang of it. I sucked it hard and deep. Up and down went my mouth. I even tried some deep-throat stuff. Then they held my cock and started stroking it. Then we came into the 69 position and started sucking each other off, and I must say that they were better at giving a blowjob than any woman I had ever been with.
After a long sucking session, they took out a condom and started wearing it. I understood that it was time to lose my anal virginity. I told them to use some lubrication as it was my first time. They applied some lube and started to enter my asshole. They got me on my back and kept a pillow under me, then thrusted to get half of their penis inside me. I was in another state. A mix of pain and pleasure. Before I could react, they thrusted once more and inserted the rest of it inside me. I was ecstatic.
They raised my legs for better access and increased their speed. My head was banging against the bedside, but it didn’t matter. They kept on thrusting into me. Then they changed the position to doggy, held my hair, and started banging like anything. This continued for the next 10 minutes. I was in both pain and pleasure. After some time, as they grew tired, I asked if I could fuck them now. They instantly got into the doggy position for me and applied some lubrication to their asshole.
It was my first time fucking anyone’s ass. I put on the condom and started fucking. The asshole was pretty tight and gave me immense pleasure. I fucked them for a couple of minutes, but then they got up and started to fuck me again in doggy style. I reminded them to cum in my mouth, so after five minutes of intense fucking, they took out their penis and threw away the condom. Then they started stroking their sick in my face and in a few seconds, inserted the dick in my mouth and started cumming vigorously. All of the semen was shot at the back of my throat, and I happily drank it and started sucking and licking their dick if any remnants. I licked the penis dry.
Now I had still not cum till now, so they started to suck my cock hard to make me cum, but I have a lot of stamina. I don’t cum easily. They kept on sucking and sucking and sucking. As they grew tired, they exclaimed, “Aapka jaldi nahin nikalta hai na,” to which I replied, “Yes.” Then I got them into the 69 position again and started to suck their semi-hard dick again.
As we both were sucking each other’s dicks, I was about to cum after 10 minutes. So I held their hair and started to push their head down at speed.
Soon I came, and I came in huge loads. They graciously took all of it. And when I was finished, they got up and spanked me lightly and went to the washroom to clean up. I got dressed and waited for them. We kissed again, and they gave me a cock squeeze as I went out.
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Hulkwolf