James' First Grindr Hookup

This story takes place before Sam and James meet.

All characters are fictional and over the age of 18.

This story is between a trans man and a cis man

Some "female" terms are used to describe the trans man's genitals. There is no misgendering.

James needed it bad. It had been months since he and his girlfriend broke up and even longer since they had had sex. Being on testosterone made him horny all the time. He had been looking for a girlfriend but was having no luck. James had been bicurous for a while but he had never had sex with a man. Eventually horny and desperate, he turned to Grindr and made an account. He wanted to keep it anonymous so none of his pictures included his face. His bio read "Horny trans guy looking to get pounded. All holes open for use. Anon preferred" and he started. He was lucky enough to live in a large city and there were many guys to look at. James sent some guys messages and got some replies.

One message stood out from the others. From HornyDaddy69

"I want to walk in and find you bent over, completely nude and waiting for my dick. I want to pound your pussy and ass and make you scream. I want to cum balls deep in you"

James was instantly wet and horny. Then came the pictures.

A man's torso with a soft cock hanging in front of him.

A close up of a hard cock next to a ruler showing it measured 10 inches and looked thick.

A video of the cock being jerked off and squirting ropes and ropes of cum.

James immediately replied "I want that so bad. I am so horny right now"

"Any pics of what im gonna be fucking?"

James immediately sent back some pictures of his hole and his ass hole, as well as a few of him fucking himself with a dildo

HornyDaddy69 liked the pictures and said "when can i pound you"

James was immediately concerned. He wanted to get fucked but this was moving a little too fast for him. He messaged asking for STI testing and got back pictures of negative tests from about 2 weeks ago as well as a surgical report of a vasectomy. James was relieved knowing that there was no chance that he could get pregnant (testosterone isn't 100% effective as birth control).

He summoned up all his courage and messaged back "I'm free now"

The next message was the man's location.

"How far away are you?"

With shaking hands James put the address into his GPS.

"About 20 minutes"

"Good. Put a plug in your ass right now. I you to be ready for me. I'll leave the outside light on and the door open. You will enter and go into the second door on the right (the only room with a light on). Take off all of your clothes and bend over the bed. Message me when you are ready."

"I want to clean myself out first so it might take a little longer to get there"

HornyDaddy69 replied "Good boy. Wanting to please your daddy. Message me when you leave so I can be ready"

James took a deep breath. He could still back out. His mind was racing. The logical part knew that this could be dangerous. Having sex with a man that he had never met in that guy's house. This could be the stupidest thing that he had ever done. Then the horny part of his brain took over and he replied

"Yes daddy"

James started to get ready before he thought about it too much. He stripped, grabbed a fleet enema out of his closet, lubed up the end and slid it into his asshole, then pushed the liquid in. It was empty in about 2 minutes. James held it for about 5 and then expelled. He then grabbed the biggest plug that he had, about 4 inches long and 2 inches thick at the largest point. He lubed up his fingers and started to work his asshole open. When he felt it was ready he lubed up the plug and slid it into his ass. He held it with the widest part holding his hole open before he let it in all the way and his asshole relaxed around the tapered part. This all took about 10 minutes.

Before he lost the nerve, he threw on some clothes he didn't really care about and left his apartment.

He opened Grindr and messaged HornyDaddy60

"I am on my way now. Be there in 20"

In response he got a picture of a hard dick accompanied by "I can't wait ????"

As he got on the bus James was acutely aware of the plug in his ass and the control that this stranger had over him. His mind was racing. He wasn't at the point of no return yet. He could still back out. Then he felt his small testosterone dick brush up against the seam of his shorts and his breath caught for a second. He was so horny and needed a release. He was going to go through with this.

He got off the bus in a surprisingly nice neighborhood and walked a few blocks to the address he was given.

James messaged HornyDaddy69 "I am here"

The porch light was on. James took a deep breath and walked up the few stairs and found the door was unlocked. James entered the house and went to the second door on the right. He found a pretty small bedroom but it was well kept.

His phone buzzed with the reply "Good. I can't wait. Let me know when you are ready. Leave the plug in"

James quickly took off all his clothes and put them in a small pile on the floor. He reached down and felt that he was dripping wet. He quickly sent a message saying that he was ready. Then tossed his phone on top of his clothes and bent over the bed.

It felt like he was there for an eternity. James could feel his heart beat in his ears. Eventually he heard what he thought was the front door locking. Then he heard distinct footsteps approaching the room.

He felt a hand on his lower back. And then it slid down to his ass.

"You are even better in person. I cannot wait for this"

"I can't either," James replied.

The man's hand slid between his legs and found the end of the plug in his ass. He turned it and then pulled it slightly. James groaned as the large part stretched his ass.

"Such a good boy for daddy. Knows how to follow directions and owns a decent sized plug." he whispered.

"Thank you daddy," James said.

Then his hand slid further down to the entrance of his pussy.

"Oooh, baby is wet for daddy. Can't wait to be pounded can you?"

"Please daddy. I am so horny."

Daddy started to finger James very slowly. James moaned at the mans thick fingers.

"How many cocks have been in this pussy before boy?"

James took a deep breath before replying "None"

Daddy let out a small laugh. Then James felt a weight on his back and the man whispered in his ear "So I get to take your real penis virginity. Lucky me. I will fuck you real good and leave you wanting more."

The man stood up.

"Spread your legs more. Daddy gets full access."

James moved his feet further apart. He felt daddy spread his pussy lips apart and felt the head of daddys dick at the entrance to his hole. Daddys dick felt huge, bigger than it looked in the pictures. James was worried that he would be able to take it. James could take a pretty big dildo but he wasn't able to tell if daddys dick was bigger than that.

His question was quickly answered when daddy slid his entire cock into his pussy in one movement. James let out a long loud groan "daddyyyyyy" His dick was bigger and was stretching James in such a nice way.

"Mmm yeah that's a good boy. Taking daddy's dick so nicely. Im going to fuck you so good"

James moaned. He was so ready to be fucked. For daddy to use his holes.

Daddy started fucking him. Slow long strokes that felt so good. James could feel daddy's dick pushing up against the plug that was in his asshole.

Daddy started to pick up speed. The strokes were still long but now coming faster and faster. James could feel daddy's balls slapping up against his dick. Every slap pushing James closer and closer to orgasm.

"Be a good boy for daddy and take his cum"

James moaned and felt daddys dick twitch inside of him. Then he felt spurts of cum shoot into him. Daddys orgasm seemed to last forever and the cum just kept coming. James felt like such a slut and relished in it. Taking daddy's cum made James even hornier but he still hasn't cum.

Daddys orgasm ended and he stayed inside James' pussy and slowly started humping him.

"Just wait a second for daddy to get hard again and then im going to fuck that ass."

"Thank you daddy"

"Can I blindfold you? I want to see the look on your face when i fuck you>"

James nodded and closed his eyes. He loved sensory deprivation and was a natural submissive. This felt like a dream.

With daddy's dick still in him, James felt something soft over his eyes. When he opened them everything was dark. Daddy slowly pulled his dick out and to James' surprise he felt something slide in.

"I had a dildo made based off of my cock. This way I can fuck both of your holes at the same time. Now roll over."

James was so happy. He loved having both of his holes stuffed at the same time.

Once he was on his back, daddy pushed his knees up towards his chest and turned his but plug and gently pulled it out. James could feel his ass hole winking, wanting to be full again. James felt daddy squirt some lube into his ass and rub it around a little. Then he felt the head of daddys dick at his asshole. It was much thicker than the plug.

Daddy's head stretched his ass and then popped in. Daddy worked his dick slowly into James' ass. James felt every inch slide into him. His ass felt more full than it ever had before. And his pussy was still full of daddy's dildo. James was breathing hard and focused on all of the sensations trying to get his brain to comprehend what was happening.

Eventually daddy whispered "that's all of it boy. You took all of me. Good job."

James blushed at the praise. "Thank you daddy"

Daddy stayed still and let him get used to the size for a bit. James felt daddy fiddling with the dildo but could not figure out what he was doing.

"Here we go boy"

Then he started fucking him, fast and hard. The dildo moved at the same rate that his dick did. James' pussy and ass were emptied and filled rapidly and in unison. James felt his eyes roll back into his head. The sensation was unbelievable. Daddys cum was leaking out his pussy and onto daddy's dick in ass, keeping everything lubed up and moving smoothly.

James could feel an orgasm building. Daddy continued to fuck him relentlessly. Both of James' holes were incredibly sensitive.

"That's it boy. Take daddy in your holes. Mmmm yeah. You like it when daddy takes control and uses your holes don't you? Daddys gonna make his boy cum."

The part of his brain that made words wasnt working so all James could do was moan in response.

James was so close to an orgasm. Then he felt a vibrator on his t-dick. That sent him over the edge. His t-dick spasmed and daddy turned up the vibrator. Waves of pleasure washed over him. Daddy kept fucking him through his orgasm, hard and fast. Daddy grunted and James felt ropes of cum shoot into his ass. James felt more waves of pleasure come over him knowing that daddy had now cum in his pussy and ass.

Daddy could tell that James' orgasm was ending and bottomed out in his ass and pussy and stayed there. He slowly turned the vibrator down and eventually off.

"Good job boy. Not many people can take me in their pussy and ass."

Daddy slowly pulled his dick out of James' ass and his dildo out of James' pussy. James was surprised when he felt daddy pressing the butt plug back into him.

"There is a towel next to you to clean up a bit. Keep the plug in until you get home. Sluts like you keep my cum in their asses on their way home. Reminds you how much of a slut you are for letting a total stranger use you to their hearts desire."

James heard daddy's footsteps walk away. He took a few deep breaths and took the blindfold off. He found the towel and wiped away as much cum as he could. He got dressed and made his way out of the house. James felt like everyone on the bus knew what he had just done and tried to act innocent the way home, but every time the bus hit a bump he was reminded of the plug in his ass and how much of a slut he really was.