Samantha Dominates Pt. 03

This is a part of a series and is best enjoyed in order, but can stand alone.

Content warning: this story is between a cis woman and trans man. if that is not your thing please move on

This is a work of fiction and all characters are over 18

Sam figured that James wasn't quite ready to have her watch him wipe yet so she decided to let him do that alone. She set about getting the bedroom ready for the rest of their evening. She got out her strapon and set her favorite dildo so it would go into her and one of her larger dildos so she could destroy James’ boy pussy. She also got out her stretching dildos so that she could see James’ asshole gape for her.

James stumbled out of the bedroom wondering what else would be in store for him tonight. Mistress Sam guided him to the edge of the bed and bent him over it. She attached the spreader bar to his ankles to keep his legs wide and open for her to access.

Sam rubbed her hands over James’ ass. James spent a few hours a day in the gym to keep his body nice and toned. His ass was so nice and she could not wait to take advantage of the cleaning he had just had. Sam lubed up her fingers and started fucking his ass. Soon she had four fingers in him and he was panting. Sam smiled to herself happy that she had found such a slutty, submissive boyfriend. Sam's hands were pretty small but she was still surprised at how quickly James’ ass opened up and she was able to rather easily slide her thumb in and make a fist in his ass.

James felt Mistress Sam add fingers to his ass and when she slipped her fist in he was ecstatic. She fucked him deeper and harder than he had ever been fucked before.

Sam slipped her other hand down to his dick and started playing with it. She continued fisting his ass and playing with his dick until he was close to orgasm. Then she stopped and pulled her hand out.

James felt an emptiness in his ass that he had not known before. He had gone from being so happy and full to being so sad and empty,

“Please Mistress” James groaned

“Please what slave. You have to be specific.”

“Please fill my ass again Mistress. My ass is so empty and hungry for you to fill it”

“Because you asked so nicely I will.”

Sam grabbed her biggest butt plug, lubed it up, and slowly slid it into James’ ass. She kept it at the widest part for a few seconds before allowing the thinnest part to sit at his sphincter.

James let out a low groan. He loved the feeling of having his ass filled and relished in being under the control of his mistress.

“Roll over”

James complied and rolled onto his back. Mistress Sam straddled his face.

“Make me cum Slave”

James immediately went to work. He alternated between tongue fucking her pussy vigorously and sucking her clit with a dedication that he had not shown before.

Sam knew that James was talented at oral but she was surprised at his enthusiasm this time and came very quickly.

Sam got off of James and put on her strap on, sliding her dildo into her pussy. She ordered James to kneel in front of her.

“Suck my dick slave”

James immediately started sucking on her very realistic looking dick. It was one of the largest dicks that he had ever tried to suck (real or fake). He could only get about 4 inches of it in his mouth before he started to gag.

Sam pulled out slightly disappointed.

“We will have to work on you dick sucking abilities before I introduce you to some of my friends. If I introduced you now they would laugh at me.”

James bowed his head ashamed that he had displeased his mistress. All he wanted to do was please her and he had failed.

“Lie on the bed on your back with your ass at the edge”

James complied quickly not wanting to disappoint his mistress again. Mistress Sam pushed his legs apart and up towards his chest giving her full access. James grunted as she slid her dick into his boy pussy all the way to the hilt in one smooth motion. James was in heaven. His ass was filled with a plug and his boy pussy was filled with his mistress’s dick. He looked down and could see the outline of his mistress’s dick in his stomach. He smiled up at her in pure heaven. She smiled back and he thought he saw love in her eyes.

Then she started pounding him. Her pace was fast and she was fucking hard. He could feel her fake balls slapping against the plug that was in his ass. The dick was hitting him in all of the right places. He was in absolute heaven.

Sam knew that she wasn't going to last long and she wanted to cum at the same time as james. She grabbed the vibrator she had on the bed and turned it up to the highest level and pressed it against his dick.

This pushed James into new levels of pleasure.

“Mistress can I cum?”

“Yes slave you can cum”

James and Sam reached their climaxes at the same time. Both in pure ecstasy. Sam did not stop fucking through her orgasm making both of them cum harder. Finally Sam came to a rest with her dick buried deep in James’ boy pussy.

When she regained her strength she slowly pulled out of him. Then she slowly tugged the butt plug out of him. She pulled off her strap-on. James rolled into the middle of the bed and Sam lay down next to him. They drifted off to sleep in their post orgasmic haze of pleasure.