Chapter 3:
Three weeks ago
It had been a week and a half of sneaking around Leah. It was technically not cheating, but it was lying. Lying, the one thing they promised to never do to each other. But Master Vincent was clear, this has to be behind her back.
Juan couldn't think clearly anymore. He had experienced so much pleasure at the hands of Master Vincent that he could no longer stomach it. Anything that man said, he would do. And he was clearly showing that as Master Vincent continued to stretch Juan's asshole with the speculum. In one short week, Juan's hole went from a slightly used sleeve to gaping the size of a golf ball. He was ready, he was more than ready, he needed to feel Master Vincent's cock in his sissy pussy.
The two of them met at the club most of the time, but since James and Master Vincent knew each other they started meeting at James' house a few days ago. It was a beautiful house in the suburbs, about 20 minutes from his current apartment with 4 rooms, 3 baths, huge basement that he was now getting his hole stretched in. The yard was huge as well. Everything he and Leah were looking for. The basement was a long space, separated only by the columns of the foundation. It was decorated from wall to floor with BDSM paraphernalia. Plugs, chains, cuffs, name it. It would've been a dark space if not for the red wall lights decorating the walls.
"Ohhhhhhhhhh Master Vincent thank yoooouuuu..." said Juan and Vincent replaced the speculum with a large plug.
"Two hours, that should be enough to gape you a bit more and get you back home where you can continue to edge Leah." Master Vincent said. He left, leaving Juan tied up in the basement, whimpering over the size of the new plug.
It was filling but unmoving. Juan needed someone, anyone, to rub that plug around his willing bussy. His prostate was crying out for attention, so he started pushing out his anal muscles and then pulling them back in. It was so much effort, it got tiring after a bit, but whenever he stopped his prostate started screaming in his head again.
Once the two hours passed, Master Vincent came to collect the whimpering sissy from his basement. He found the sissy on all fours trying to fuck herself with the plug using only her anal muscles. His resolve was tested yet again, but he knew that he needed to keep his word to the sissy. No sex unless it was with both of them.
Juan noticed Master Vincent standing and said "Sir, Sir please, I have to go hoooome..." he whimpered, making himself dribble out a bit more cum from his flaccid clit.
Master Vincent disrobed himself, making it a show for the sissy, whose mind was a mess. She was drooling over his muscles and cock. She needed it as much as he did. So he thought he should play a game with her. He walked over to the sissy; uncaringly and quickly removed the plug, making her groan in pain and pleasure. Then he kneeled behind her, his cock at the mouth of her gape. "I've taken it out, but I won't untie you yet. We still have more time. I'll kneel here, my cock is right in front of your hole. If you want it, you only have to back up"
Juan was in turmoil. He was soooooooo empty. He had felt full with the plug and it was ripped from him so quickly and harshly. He didn't have time to remember the wonderful feeling of being full. Master Vincent's cock was right at his bussy. He could be full, he could be loved the way a sissy needs to be. His mind didn't even think of Leah at the time, it was fully focused on his hole being empty.
"Oh GOD PLEASE MASTER VINCENT, PLEASE!!" and Juan plunged his ass backwards hoping to feel full again. Instead he found nothing but air. Cruel, unfeeling air as Master Vincent saw the sissy move and stood up quickly.
"Oh darn, look at that, our time for today just ended. Too bad... wait, were you about to cheat on Leah?" Master Vincent cruelly mocked Juan.
Juan took a second to understand what had happened. He needed a second to calm down and then he replied, through tears "
Please Master Vincent, please don't tell her
"
"All she has to do is be a good hole and submit to my cock as well. If she does that, I'll feel enough gratitude from both of you that I can overlook this lapse in judgment." he replied.
They walked upstairs after they cleaned up, Juan never able to once look up, his shame deep.
"Sir about the house..." Juan started.
"It's yours, of course. But if you can't convince Leah to enjoy my cock then the deal stands, I stay here, you break up with her and you move in by yourself. Understood?" Master Vincent grabbed Juan's cheeks and made him look up. James and his wife wouldn't be without a home, they would finally move into Master Vincent's house and become a 24/7 cucked couple after 20 years of playing with Vincent.
"Yes Sir" Juan agreed.
"Did you send out the brochures?" Master Vincent asked, making sure his plan was on track.
"Yes Sir, I put them on the houses of a few people I'm pretty sure will talk to Leah" Juan answered.
"And the dildo?"
"I'll pack up her current one once we start packing, Sir."
"Good. Once the sale is approved you are ordered to fuck Leah. Give her as many orgasms as you can. And then you won't touch her until after I do."
Juan whimpered, "Sir, I'd prefer not to..."
But Master Vincent was already looming over the petite sissy. And she knew she wouldn't be pussy-free until after the sale.
_____
Current Day
Ben and Leah entered the room with drinks in hand. It almost felt like walking into a tiger's den. Ben promised not to say anything to anyone, unless Emil asked. He can't lie to him or he might not see the show his wife and Emil were going to put on tonight.
"So how was the bar?" Emil asked Leah.
"It was nice, not too full, not too empty." Leah replied. She handed Bri her drink while Ben handed Emil and Kara theirs.
"Cuck, what did you talk about?" Emil asked Ben who was already undressing.