Hey guys, I’m Shrey, and this is the story of my friend Jai from Grindr and his experience as the waitress. I am bisexual but not a crossdresser. But he is a crossdresser and occasionally likes to dress up as a female.
He is bottom by nature. He is kinda girlish too. He has fair skin, with very little hair on his body. He has a puffy and soft chest due to fat accumulation, which can be pressed like the boobs of a girl.
Once he met a man on a gay site who was a restaurant owner. He had some weird fantasy. He liked to masturbate on taboo sex happening in front of him rather than with him. So they met at a hotel room fucked, and had fun. But later, he asked him something weird.
Man: I own a small restaurant. It’s more like a diner for cheap food. I don’t offer all kinds of fancy food, just some local stuff for local people who can’t cook by themselves at home. Mostly my customers are factory workers, rickshaw pullers, street hawkers, etc. I want you to work there as a waitress for few days.
Jai: What, but why?
Man: I want you to become a slutty waitress. They are the people who don’t get to see girls normally. I want you to tease them by your hot looks and finally watching them give in to their inner lust and fuck you hard.
Jai: Oh, but I don’t want to work as a waiter. Even if I do, what will I get?
Man: Don’t worry, you won’t have to work much. Just push some plates, that’s it. And I will pay you more than a waiter gets. And after they fuck you, I’ll pay even more.
Jai liked the whole idea and also a means of earning something, so he agreed to become that man’s slut. He told Jai what and how to dress up, and Jai went to prepare for that. He adorned a really sexy attire. Waxed his legs, worn a push-up padded bra that really made his chest look like boobs. Put a lot of make-up, eyeliner, etc.
He wore a really short skirt that ended just above his ass. He wore a white-colored thong that didn’t even cover his ass. It was just a narrow string that went deep in his ass crack at the back. So there was nothing that could cover his ass.
Above the waist, he wore a translucent red top from which his bra’s outlines were clearly visible. He really looked like a whore. He went to the diner in the morning, and customers started coming. The owner introduced his customers to his new waitress Rangeela.
They were dazed by him. They had not seen such beauty in real life in person. They ate less and stared more at him. Jai and the owner were enjoying this. They even ordered more food and ate slowly to extend their stay in the diner.
She smiled sluttily at everyone. Then he gave everyone a show of his ass. He bent down to pick up the fallen pen, and his skirt rose up completely, till the waist! His whole ass was visible, and that too uncovered. It was a different kind of turn-on to everyone.
They just stopped in between, their eyes glued at his clean, smooth ass. Most of them adjusted their crotch with their hands. Many got hard-ons. He even took more time to rise up and gave a complete show of his ass.
When he rose up and went to one table to take the order. While he turned to go, one hand gently brushed his bare ass by his hands. And he didn’t mind it at all. It seemed as if he didn’t even notice.
So the people’s daring increased. They began touching his ass, rubbing their fingers over it. A few even pushed their fingers inside his ass crack, and he didn’t mind. The owner enjoyed the whole show.
The next day, the owner gave him a butt-plug to put in his ass while waitressing. He did that. The next time when he bent over, his bare ass was there in front of everyone’s eyes with a butt-plug head coming out of his asshole.
People began to whisper, “What a total slut she is. She must have fucked someone yesterday, and that too, very hard. She enjoys butt-plug in her ass. I’m sure she will enjoy our cocks in her ass too.”
One time he fell directly into the lap of one customer. He could feel his dick poking in his ass. He gave a smile, adjusted his ass to put the customer’s cock in his ass crack. The customer felt too great during those few seconds.
The next day when Jai bent down to show his ass, one person rose. He walked behind him, rubbed his crotch on his bare ass through his pants for few seconds, and stayed there. When he rose up, Jai asked, “What are you doing?” He replied, “Sorry, I bumped into you.”
When Jai went to the washroom (ladies). There was a common area of the washroom that separated men’s and women’s entrances. That same man was standing there. As Jai came out, he pulled Jai inside men’s and closed the door.
He: How much more will you torture us by your hotness and sluttiness? Why not give it to me now?
He took his hand to Jai’s ass, moved it between his ass crack, and came across the butt plug.
He: Why do you use this lifeless thing for your ass? Use my cock.
And he pulled out his hard cock. Made him turn around, pushed him on the urinal, pulled out the butt-plug from his asshole, pulled aside the string of his thong, and pushed his cock in his ass. Since the only lubrication source was the precum oozing from his ass, the cock was quite rough and painful.
Jai started to scream, but the man covered his mouth with his hands and kept on giving thrusts in his ass. He said, “You have teased me for quite a bit. I’ll take all of it back by fucking you hard.”
With every 2 words, he gave a thrust, and his voice also became tensed. After 3 minutes, he cummed in his ass. Cum flew down from hole to floor. He was panting after the fuck session. After all, he was a 50s man. In the last bits of fucking, Jai’s pain had gone, and he also enjoyed the fucking.
The man turned around Jai again to face him, went down, raised his skirt from front, and pulled down his thong. He was shocked to find a cock there! He looked at Jai, “What the fuck is this? You are not a woman. Are you a trans?”
Jai: No, I’m a boy, regular boy, just on make-up. Sorry to disappoint you, but I never said I was a girl. (And smiled)
The man rose up, lowered down his cock, and found there were only padded bra and other stuff to make up for his boobs, no real boobs. His expression of shock was really funny.
Jai: Why are you disappointed. Didn’t you have fun fucking my ass? Be it a man’s ass, but you had real fun and orgasm.
His expression changed to somewhat confusion. He opened the door and went out. Jai put the butt-plug in, adjusted his dress, and went out. There was another man who saw Jai coming out of the men’s room after that previous man. He understood what would have happened.
He went to Jai and said, “I also want you. If you gave him, you have to give me also, and he held his arm and started taking Jai to the washroom.
The man who had fucked him earlier told the next man that he was a boy dressed as a girl. When the next man heard this, he became a bit furious, pushed Jai inside, and closed the door.
He made Jai sit on the floor and took out his cock for sucking. Jai took it in his mouth and started sucking it. As it grew harder, the man began to roughly fuck his mouth by holding his head against the wall.
Jai began to choke, and saliva started dribbling from his mouth. After he almost choked Jai, he took out his cock, and Jai took a huge sigh of relief. He made Jai stand up and turned him around to face the wall.
He made him bent down on the urinal, which was stinky and dirty. Jai had not thought this would be the consequence of his little foul play. He had to endure the smell and dirtiness till this fucker was satisfied.
He raised his skirt, took out the butt-plug, and pushed his cock in his asshole, lubricated by the previous cum. He fucked his hole with full power. But in the end, Jai also began enjoying the rough fuck. At the end of his fucking the man got so excited that he tore Jai’s skirt and top.
By this time, people started to bang the door, “We also want him. Give his ass to us also.”
H replied, “Wait, I’m cumming out in few seconds,” and he cummed in his ass with a huge orgasm.
He opened the door and went out. Outside, people were standing that watched the whole scene in which Jai fell on the ground. His asshole leaking cum, and his hole sore and red. He lay with his back towards the door. So his cock was not visible, so people still didn’t know about his secret.
The man called everyone away from the washroom and announced in front of everyone Jai’s secret. Everyone was shocked! Then they went to the washroom, dragged Jai out in the open
He said, “So until now, you were fooling us with your sexy girlish ways. You must pay for it. You made everyone hard, so now you have to take and relieve each and everyone here.”
One man bolted the door from inside so no interruption could occur. A total of 11 men were about to ravish Jai’s youth with their cocks. They all opened the string of their pajamas and removed them.
One came to Jai, made him stand, and tore apart his skirt and pulled out the string of the thing from his ass crack and tore it. Another tore his top and bra. Within minutes he was completely nude with his cock hanging down.
One took out his cock and put it in his mouth, and started fucking his mouth. Another came to take his ass. Both his holes were filled. As the mouth man cummed in his mouth, Jai was forced to swallow every drop.
The next one came then to replace the earlier one. After the ass man cummed in his ass, he was replaced by another man. And like this, every one of the 11 took turns in fucking both his holes.
He had swallowed a lot in that 2-hour session. His ass hole had become too sore, red, and was gaping fast. It was filled with mixed multiple cums of everyone. While fucking him, some of them spanked his ass very tightly so that it turned almost red.
During that fuck session, Jai also had cummed multiple times. He could barely stand after that session. The restaurant owner, while watching his fantasy getting fulfilled, enjoyed all this show and masturbated heavily.
“So now you understood what’s the consequence of someone pretending to be a hot slut and tease men,” one of them said.
Jai swore never to pretend to be a hot slut again.