Hotel Encounter Pt. 01

Jay was a 5 foot 10 Indian boy, he has longish hair and he is a little chubby. And this is the story about how he lost his virginity.

He was sitting at home browsing through the gay apps. His hand slowly rubbing his dick. Just enjoying the erection. When suddenly he received a message from an older white man. Jay had always fantasied about being with an older man. However, he had only been with guys his age. And that was only for oral. Jay begins to browse his profile. He was called Kyle. He was overweight, if not obese and in his 50s he looked like a proper daddy. They began to message, a bit flirty at first, but a connection was growing. Jay was weary about being catfished, but after exchanging more photos including dick pics, they were both sure they were real. But Jay was from Derby, and Kyle from London, it would be hard to meet on an instant as there is miles of distance between them.

Over the coming weeks they would message each other several times about, with a couple of days they would tell each other that they loved the other. Obviously, this wasn't real but they both loved the thought. Then the conversation turned a bit kinky, once they ran out of things to talk about. They started to talk about kinks, and Kyle discovered that Jay was into crossdressing, and loved wearing dresses and panties, and wanted to be submissive even though he lacked experience in that department. So, Kyle began to call Jay slut and Jay was to call Kyle Daddy, as he learnt that Kyle was dominant. Jay figured it was a good time to let Kyle know he was a virgin. Kyle was excited by the thought.

A few days later Jay became free for the night and he told his Daddy. They agreed to meet on Friday night, Kyle suggests they meet at a restaurant however Jay prefers they meet in the hotel bar for discretion. His Daddy asks his slut what he shall wear, but as Jay in nervous and not out he says he will get changed fully once there. Jay chooses an orange and black dress, that goes down to knee length. Some black panties, that struggled to hide his bulge, and black pantyhose. He puts on the pantyhose and panties, putting the dress in his back as well as boots that he bought. He then began to shave his body from the neck down wanting to impress his daddy. They were to meet at 6.

Jay leaves his house at 5, and begins to head to the hotel, bag in tow. His dick was semi hard. But he was excited. This was the first time in public he had worn his panties. They meet at the bar, for the first time in person both nervous. Kyle waves to Jay he was wearing a suit. A proper Daddy. Neither lied about the way that they look. They begin to have small talk and have a couple drinks, they are both so horny, the conversation doesn't matter as they are both just thinking about sex.

Kyle asks Jay "You know when we go to the bedroom, I'm going to have to call you a girl's name."

Jay responds smiling at his daddy "What do you want to call me?"

"How about Jaya?"

Jaya smiles she likes that name and is lead to Kyle's room. As they enter they don't speak as Jaya heads straight to the bedroom to put on her dress. She was nervous. This was the first time anyone would see her dressed, but she was happy it would be her daddy. Her clit was harder than it had ever been as she leaves the bathroom.

Kyle stares at her "Holy shit, you're stunning".

"Thank you".

Kyle puts his hands on Jaya's face as they kiss for first time. They melt into each other. Moaning and groaning. Kyle moves his hand down to Jaya's ass feeling her up as Jaya begins to grope her daddy's cock. They are both hard and both begging for each other. They move to the bed still tongues entwined with each other. They roll on the bed together, Jaya takes of Kyle's Jacket and shoes, as Kyle undoes Jaya's boots. Kissing her legs and feet as he goes. They lie in bed together pulling the covers up still passionately kissing. They Kyle grabs her clit, and Jaya massages his cock, it must be at least 8 inches she thought. They both free their tools. Before they begin to thrust their tools against each other the groans were loud, but they didn't care if anyone heard them. They were both incredibly hard and horny. Kyle then asks Jaya if she's ready. She whispers yes. Kyle kisses her before pulling of the covers and getting her ready in doggy style. Kyle then rips her pantyhose and lifts her dress up as he removes the last of clothes. He gets some lubes and rubs it on her ass before slowly pushing against her. "Relax" he says stroking her back before he enters her. At first Jaya feels uncomfortable but as Kyle being to thrust it turns to please.

"Yes, please Daddy." She says like the slut she is. Kyle reaches around as they both cum. Jaya can feel Kyle's dick pumping in her, as she splatters the bed. Neither of them cares. Jaya takes of her dress and ripped pantyhose and lies with her daddy. Both nude. Her daddy the big spoon her the little. They fall asleep both horny for tomorrow morning.