I was staying at a hotel in India. It was not a very posh hotel, not a very cheap one though. Like a 3 star.
So I was supposed be there for a week because of official work and it was my last day. I had the whole day to myself and no work. Was packing all my stuff and then went down for a stroll.
There was a local market nearby where you could get fruits, groceries and clothes for cheap.
I got to a stall where they were selling women’s lingerie at very low cost. The sissy in me thought that a few rupees will not hurt my pocket and I could wear it in my room for rest of the day and feel feminine.
I bought a sexy bra, a netted thong and a mini skirt for just rs.600.
Went to my room and tried it, it fit me very well, I loved my round ass visible in the mini skirt.
After like half an hour I felt hungry and ordered a pizza.
When the bell rang , I thought I should wear a bathrobe but I thought of taking the risk and showing up at the door in lingerie because I was supposed to leave that night.
I knew it was risky but had to try it.
I opened the door and the pizza delivery guy was shocked to see a man in women’s lingerie.
I took the pizza and then turned to get money. I knew he was looking at me constantly and my ass.
When I gave him the money, he asked me why am i wearing this? I told him that I liked how it feels wearing women’s lingerie and asked him to tell me genuinely how do I look and then turned for him a few times. He smiled and said that he has never seen a guy dressed like that, and that my ass looks better than his wife’s.
I smiled and told him he can grab it if he likes it that much. I closed the door and he grabbed my ass 2-3 times and I could see how excited he was getting.
I told him if he wants to jerk off putting his dick on my ass then i wouldn’t mind. He got so excited that he started opening his belt and in excitement was taking long.
Then I told him to relax, got on my knees , kissed his bulge over his pants , opened his belt, removed his trousers slowly and exposed his brown veiny dick leaking pre cum. Then I bent for him to rub it on my ass.
But to my surprise, he just said please can I and then slided off my panties and started licking my ass. Fuck that felt amazing and then after a few seconds I felt a finger fucking my ass. I started moaning and then he said now I will jerk off but in your ass. And then entered his cock, in and out in and out. A few thrusts later I felt warm cum in my ass.
Then he turned me around and said he had always wanted to fuck a guy and he finally got to fuck one dressed as a girl. Before going out he asked me if he can shake my dick because now he wanted to see how it feels holding another man’s dick.
And let me tell you, this guy was very naughty, he stroked my dick over the pizza I had ordered and made me cum over it. And later took a bite from that pizza as well.
When he went , I just hoped he didnt come back with somebody so I just finished packing and checked out of the hotel within one hour and took a taxi 6 hrs earlier to the airport.
The whole flight, I was wearing the bra and thong underneath my men’s clothes with the pizza guy’s cum in my ass.
Source: reddit.com/r/gonewildstories/comments/10fx0sr/pizza_delivery_guy_fucked_indian_sissy_cd_m25_mm
We need more MM on the sub!