Over the next few days Mistress Andrea continued Sissy Robert's cock sucking training with her strap-on. She wanted him to be ready to suck her new friend when she brought him over after their dinner date Saturday night. Mistress had informed her man that she owned a sissy and would want sissy to get him hard for her. The man, Paul, told her that it would be fine. Mistress ensured during Sissy's training that he fully understood her expectation's, disciplining sissy for the slightest of mistakes, and constantly keeping the threat of a whipping with the single tail if he embarrassed her by not sucking her man properly come Saturday night.

 

When Saturday night came, Mistress Andrea had Sissy Robert dressed in an all pink sissy outfit and had him answer the door when Paul came to pick her up. Paul gave Sissy Robert the once over as he opened the door and while shaking his head chuckled as said "fucking fag." Sissy Robert's face turned red with embarrassment and told Paul that he would tell Mistress that he had arrived. "No need faggot I'm ready," he heard Mistress Andrea say as she walked into the room, looking stunning as always. "We'll be back in a few hours sissy boi, and when we do you had better be prepared to perform as you have been taught or so help you you'll regret it," she said firmly.

 

Sissy Robert was very nervous during the time they were gone, fearful that he would not suck Paul to his and Mistress's satisfaction and be harshly disciplined. As he sat in his room he wanted to practice on a dildo, but Mistress had purposefully locked them away so he could not. He was either ready or not, the consequence of the latter too dreadful to think about, but he could not stop doing so. He had never sucked a real cock before and Mistress Andrea was expecting a night of pleasurable sex, which would only not happen if sissy messed up.

 

When Mistress Andrea and Paul returned, she walked to sissy's room and told him to follow her and Paul to her bedroom. "Kneel by the bed faggot with your head bowed," she ordered.  Sissy Robert did so and could hear the sounds of them kissing and caressing each other.  After a short while, Paul moved in front of Sissy Robert and Mistress Andrea said "time to suck faggot!  Open his pants and get him nice and hard for me." Sissy Robert's face flushed and he gently bit his lip as he nervously unzipped Paul's pants. He hesitated a moment prompting Mistress Andrea to say, "it's not going to come out by itself faggot, take it out and suck it."  Sissy Robert gently took Paul's cock out and slowly began to stoke it.  "Suck it you fucking fag," ordered Mistress Andrea,  and Sissy Robert began to mouth Paul's cock.  As he continued to stroke it, he alternated mouthing the head and licking up and down the shaft as the cock began to grow, sissy started to suck it, gradually taking more of it into his mouth. Paul's cock was getting thick and large and sissy began to relax a little so that he could suck as much of it as possible without gagging. "That's it faggot, suck it until he is completely hard and erect,"  instructed Mistress Andrea, adding  "I want him ready for me, my pussy is getting wet watching you suck him."  Paul's cock grew larger and thicker than the dildos he had been trained on, and he eventually gagged as he tried to take it all down his throat.

 "Enough faggot, he's mine now," ordered Mistress Andrea.  Sissy Robert kept his lip's around the cock as he was releasing the cock from his mouth. "Get the fuck out of here faggot, I'll let you know when it is time to suck again," said Mistress Andrea.  Sissy Robert quickly got up and hurried from the room as Mistress Andrea and Paul embraced began to passionately make love.