The Sexy Painter

Miss Victoria walked away and starting rummaging through a cabinet that was in the middle of the crowded room. She was behind Tommy, who was trapped a foot or so out from the shelf, facing the wall. He twisted his head from side to side, trying to see what she was doing to no avail.

"Ah, yes. Here it is." Miss Victoria said, taking hold of something and walking back to Tommy. Try as he might, he couldn't see what it was as she approached. "My Wednesday boy uses something bigger, but I think this one is good for you. At least to start with.`"

It wasn't until she was within an arm's reach of him that she held it out so he could see it. It was a short, finger width phallus with a round base.. His eyes widened, suddenly very concerned about where she planned to put that. His fears were realized when she traced a path down his back with it. Sliding it down, between his cheeks and rubbing it against his anus.

"No, Miss Victoria," he begged, "Please don't use that."

"Oh, do you not need it after all?" she asked, reaching around and taking hold of his dick once more, "Are you able to have another good cum for me?"

"I'm sorry Miss Victoria, I can't." He told her.

"Can't or won't?" She asked, holding his flaccid penis.

"Can't. I swear, if I could, I would. But I just can't." He explained.

She began rubbing a gooey mixture on the small phallus. "The thing is Tommy. I've known a lot of boys over the years that thought they couldn't provide me with the supplies I needed but..." She stood behind him and placed the phallus between his butt cheeks, "they all could. Every single one of them."

"Wait. What are you..." he started the panic.

"Shhh, it's okay. This is just a little aid, so we can empty out those testicles of yours." She told him, as she rubbed the phallus up and down his anus, spreading the lube liberally.

"No. I'm empty. I swear. You don't need to..." he tried to move but the restraints stopped him from much movement. Before he could twist his body away from her she was pushing the tip of the phallus against his anus. "Oh, fuck!"

His objections were largely based on insecurity, things going into bottoms seemed "homosexual" and as a straight virgin, he was scared about what this would say about him. Miss Victoria didn't care though. She knew how much pleasure massaging a prostate could be for a man, and how it would enable her to fully drain him. And draining his balls was exactly what she needed to do. For her art.

"Tommy, if you relax, I promise this will be enjoyable," she assured him, "quite enjoyable, I've been told."

She pulled the phallus away from him and applied more lube. He felt the tip of it as she placed it against his anus once more, and then some pressure as she pushed gently.

"Relax, it's okay." She told him, but his body tightened up.

"Tommy. I'm very disappointed with you. You're not being a good boy." She told him crossly. She pushed a bit more. Tommy took a deep breath and forced himself to relax. The tip found his opening and slid inside him.

She began rocking it back and forth, never taking it completely out and slowly going deeper, working it way inside his posterior. "That's it," she encouraged him, as she slid it back a little once more, "Let it fill your bottom." She pushed it in deeper still until it's wide base rested against his cheeks.

"Oh. My." Tommy uttered, as she penetrated him fully. He hadn't ever considered sticking something up his butt, it just wasn't a thought that had occurred to him. He regretted that as he was learning it was something that actually felt quite nice.

"This will help get every last drop out of you." She assured him. "How does it feel Tommy?"

Tommy was still feeling a bit insecure. It felt wonderful, but he was ashamed to admit it. "It's...okay, I guess."

"Just okay?" She laughed. "Your penis her says otherwise." She told him as she took hold of his erection. He was, once more, rock hard.

"Oh. God." He moaned as she stroked him again.

"There we go. Your bottom is all full and you're ready for another milking," She hummed. "Did you know the male g-spot is located on the prostate?"

He didn't, but the combination of her hand on his dick and whatever was in his butt felt so good, he believed her. "All nice and hard," She cooed, still stroking his cock, "like a good boy."

Victoria began using both hands, one in front of him, the other behind. She matched her movements so that as the hand on his penis reached his tip, the hand holding the phallus had it completely inside him. When it was nearly out of his backside, her other hand hit the base of his cock, the moment looked a little bit like she was sawing a tree.

The steady rhythm had poor Tommy moaning and groaning as she had her way with him. His hands were bound so he was unable to stop her, though he was enjoying himself enough he probably would not have.

"You're doing such a nice job, Tommy. I've very happy with you," she praised him, "How would you like to be my assistant, hmm? Do you think you can do this for me every Tuesday?"

Her hand continued to stroke his cock, though she shifted the tempo so now the phallus was nearly out of him as her other hand circled his crown, then she plunged it back in as she had shot down his shaft. "Oh, fuck," he groaned. The thought of a woman having her way with him was incredible. That it was happening and she was offering to do it every week was unbelievable. "Fuck, yes. YES!"

"Oh goody!" she said happily, "I do think you're going to make an excellent Tuesday boy. We just need to do one more thing. Do you know what that is Tommy?"

Her hands were a blur as she pumped with one hand and using the phallus to fuck him with the other. "I need...to give you... a good cum!"

"Very good Tommy! Very good indeed!" She seemed genuinely ecstatic, "Do you think you can? Can you give me another good cum? Not just a cum mind you, I need a good cum from you." She emphasized the word good as if he had any control in regards to whatever it was she thought made a good one.

Tommy, of course, agreed, as he would have to anything that would me we would get to orgasm again. "I promise to give you big boy spurts."

Miss Victoria gave the phallus one last push, twisting as she did, as though she was screwing it into place. She may as well have, as she left it there and reached for another of her special globes. He moaned, the twisting massaging his prostate in an unexpected and delightful way.

"Fantastic!" She told him, holding the container in front of his cock. She pumped his shaft, milking his cock, waiting for his final release, "You really are doing a marvellous job. I bet Nancy would agree if she were here."

He moaned at the thought of Nancy standing beside Miss Victoria, nodding in agreement, watching his cock being milked. The imaginary wind lifting her dress and flashing her panties again.

"I think you're going to be a very good Tuesday boy, do you?" She asked.

"Yes, Miss Victoria." He agreed, his orgasm beginning to rise.

"And you're confident you can do this every week from now on?" She asked as her hand pumped him faster and faster.

"Yes, Miss Victoria." He agreed, an edge in his voice making it clear he wasn't going to last much longer.

"And you'll be okay refraining from touching yourself between sessions?" She asked, "There can be no masturbating, you understand?"

"YES MISS VICTORIA!" He cried out.

"No ejaculations of any kind." she clarified. It was too much, all this talk about masturbating and ejaculating while something pressed against his prostate and her hand milked his cock. He couldn't hold back, screaming "PLEASE MAY I...AAAAHHHH "

Miss Victoria's hand continued to milk him as he shot a third load. The volume of what he felt come out was surprising, he would have sworn that he had nothing left. Yet this container was filled more than the first one had been as he continued to squirt. Miss Victoria wasn't surprised. Young men had vast resources and she had long ago figured out how to tap into those resources.

She was a bit startled by the force by which he had ejaculated, but pleasantly so. It was nice to see how each of her boys had their own unique characteristics, each had their own way of doing things. Tommy was clearly going to be very helpful with her more bold, provocative pieces. Though he was going to need to learn a few things.

"What a good cum Tommy!" She told him as she milked the last of the semen from his shaft. "A very good cum indeed. Unfortunately, you didn't ask before you ejaculated, so I am a bit disappointed with that."

"I'm sorry Miss Victoria," he apologized, "I couldn't help it."

"I'll excuse you this time, seeing as it's your first day," she told him, as she stopped stroking his shaft. Her hand slid down to his testicles, cupping and then squeezing them. Tommy's body stiffened, trying to pull away from the sudden discomfort, "but only today. You'll need to work on your self-control. We wouldn't want you cuming prematurely or accidentally ejaculating on me now would we?"

.

"No Miss Victoria," he told her, though she thought she felt his cock twitch at the thought. He had cum three times in less than an hour and his dick still reacted to her dirty talk. He was special indeed.

Miss Victoria smiled, Tommy was going to be an excellent assistant for her.

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Thanks for reading, I'd to love to know what you thought. What worked, what didn't. Do you like my more female dominate stories like this one or my ones featuring submissive women ones? Any and all constructive feedback is appreciated