Boots

Six

• Extremely graphic content •

"Holy shit." Matthew gaped as he entered the room. This guy had probably every sexual device Matthew had ever heard of and likely every one known to man.
Everything was black and leather and chains. Matthew was nervous but he was even more nervous about what would happen if he backed down. He was stubborn, if anything.
"Now's your last chance to say no. Once I close this door, were different people."
"I'm fine..." Matthew insisted.
"Gut." Gilbert slammed the door, locking it behind him. "Take your clothes off."
"What? Already?"
"There's no foreplay for you. Take your clothes off, mutt." Gilbert's voice was harsh now, low and intimidating. Matthew swallowed, slowly unbuttoning his shirt and folding it over a chair.
"Faster!" Gilbert commanded, arms crossed over his chest.
"Okay..." Matthew sighed.
"Don't sass me."
"Sorry."
"Sorry, sir."
"Sir?"
"Sir."
Matthew nodded, fumbling with his pants until they were off on the floor along with his socks and shoes.
He wanted to turn around to take his underwear off, but he knew Gilbert would yell at him. He wanted to please his master.
Wait?
What?
"On your hands and knees. Now!"
"Yes sir." Why did it feel so good to say that? Why was his groin stiffening at those commands?
He lowered himself to the floor. Gilbert attached a leather collar and leash to his neck.
"Look at you...you're hard all ready. Disgusting." Gilbert scowled. Matthew lowered his head in shame.
"I'll let you off easy since it's your first time. But just know that I don't tolerate coming early, hear me?"
"Yes sir."
"Good. Now, pick your size," Gilbert gestured to a cabinet where a bunch of dildos in various shapes and forms were on display. Matthew swallowed, pointing at one that looked small enough to handle but not so small that he looked like a weakling.
Gilbert nodded and reached into the cabinet. But the dildo he pulled out wasn't the one Matthew had pointed to. It was two full sizes larger and covered in lifelike veins. Matthew swallowed nervously.
"This is going to be the only Dick you get until you prove to me that you're worthy."
"I...I'm..." Matthew took a deep breath, "yes sir."
"I'm glad we're on the same page. Now come over here."
Matthew crawled on his hands and knees to Gilbert who pushed him so that he was even lower than he had been before, right down to the cold ceramic tile of the floor.
"I'm going to lube it up for your weak, pathetic ass, so don't get too nervous."
"Thank you." Matthew muttered.
"Are you grateful?"
"Yes. I'm very grateful, sir."
"Good. Now get your ass in the air."
Matthew tilted his hips up, bracing himself for what was about to come. He was afraid, but also curious. The most he had ever inserted into his butt was a single finger out of curiosity when he was younger. He hadn't liked it very much, but he also hadn't done much more than put it in.
"I'm gonna tell you when." Gilbert said. Matthew felt the warm tip of the dildo touch his entrance. He bit his lip.
"When."
It hurt. It was thick and hard and way bigger than that one finger all those years ago. He let out a soft whine as the tool began to move in and out slowly. He tried to grasp onto something but there was only the slick floor beneath him. He settled with biting down on his knuckles.
"Hey, don't do that." The Prussian knocked Matthew's hand out of his mouth and replaced it with his own arm. "Bite on this."
"Mmph?"
"Shhh. Did I say you could talk?"
Matthew would have replied but his mouth was full of arm and his rear was full of artificial dick. It had started to feel good at this point. He moaned through the fabric of Gilbert's sleeve.
"Louder!"
"Mmmmhh!!"
Gilbert chuckled softly in his ear, the sound making him warm all over. He could feel the pressure building and he tried to hold it back as much as possible but he found himself coming in no time.
"Look at the mess you made." Gilbert groaned. "What did o say about people who come too early?"
"Uh..."
"Clean it up."
"With what?"
Gilbert pulled on the leash, choking Matthew slightly. "Don't back talk me. Clean it up with your mouth."
Matthew swallowed. "Yes sir." He felt the dildo exiting his ass as he started to lick the floor. It was disgusting and salty but he managed to choke it all down. When he looked up he was met with a head, and not the one on Gilbert's neck.
"Wh-" a warm liquid splattered across his face. Did Gilbert just...jack off on him?
"You get to taste it after you please me twice."
"Twice more or..."
"Once more."
"Thank you..."
"I'll help you to bed." Gilbert tucked his dick back in his pants and held out his hands.
"N-no thanks I have it..." Matthew tried to stand but felt a sharp pain shoot through his back.
"Careful!"
"I didn't think it would hurt so much."
"What do you mean? You have had sex before, haven't you?" Gilbert helped Matthew into his arms.
"Well no..."
"Not even with a chick?"
"No..."
"You're a Virgin? Fuck!" Gilbert lowered him into the soft velvet sheets of the bed. "If I knew that I totally wouldn't have suggested this..."
"It's okay...I liked it...in a strange way."
"And you weren't uncomfortable at all? How old are you, anyway?"
"Twenty five."
"Shit. That's old for a virgin. Not that that's a bad thing. It really is just a personal choice." Gilbert actually looked awkward now. "I'm sorry."
"It's okay." Matthew assured him. He nestled his head into the pillow. "What do we do now?"
"Sleep. I'll be right here beside you." Gilbert pulled the covers over Matthew's worn body. "You did good, by the way. Better than any other first timer."
"You say that to everybody."
"I really don't." Gilbert took off his shirt and pants, leaving his underwear on. "I'll give you my number when you wake up so you can call if you want to do this again."
"Thanks."
"Now get some sleep." Gilbert tucked himself in next to Matthew, his pale, bear chest against Matthew's naked back. He was warm. So warm. "You're gonna need it."

Gilbert's song in this is Boots by Kesha and Matthew's is take your clothes off by Ria Mae