Thursday. Benjamin began his day in a positive mood, happy with how things turned out the day before. He quickly finished his preparations and went to school early as usual. Once there, he knocked on the infirmary's door and it was immediately opened, Sasha welcoming him with a smile. After locking the door, she looked at him as if there was something she wanted to say.
"You look the same as when you wanted to try anal sex last time. Is there anything you want to try today, Sasha?"
She blushed a little and answered.
"Actually, yes. But I am not sure you will be okay with it."
"Tell me and if I really don't like it then we can do something else."
"Alright. Do you remember when I taught you how to masturbate?"
This is something that happened during one of their many sessions. She had shown him how to masturbate and even recommended he do it if he missed her when they could not see each other. He nodded to her question and she continued.
"Today, I would like to see you masturbate."
Was that the reason why she taught him this in the first place? Watching him fap in front of her could be one of her fantasies, not that he really minded.
"That's not a problem but it isn't very interesting, you know?"
"Not at all! I am very interested in it."
"Well, okay."
"Great. And also, well, um..."
"Yes?"
"I bought a... toy with me and I would like to try it on you. Only if you are alright with it, of course!"
"A toy?"
"Yes, this one."
She went to her bag and took a long black object out of it. It was around 40 centimeters long and had a hole in the shape of vagina lips at one end. The exterior looked hard while the interior looked like it was made of softer silicone. She excitedly started to explain the object to him.
"This is a toy that men use to masturbate, it is called a fleshlight. The interior here is made of silicone and it tries to reproduce a woman's vagina. You insert the penis in this hole and then move it back and forth to pleasure yourself."
She took a small bottle of liquid out of her bag.
"It comes with some lube to make the process more fluid and a lot more pleasurable. What do you think?"
So this was her real aim. He was both conflicted and curious. As a man from his previous world, masturbating with a sex toy in front of a woman was quite a shameful thing to do. On the other hand, he also never tried any toy before and he was somewhat curious about them, wondering how it would feel and how different from a real pussy it would be. Seeing her look full of hope and thinking that such shame didn't exist in this world anyway, he thought he could try it, at least to see how it would feel like. He also wanted to stay open-minded to new things and not deny them without trying first, unless it crossed a hard line in his preferences. If he didn't like it, he could just stop and switch to fuck Sasha.
"I can try, I guess."
"Really? Great!"
She gave a big perverted grin, seemingly already anticipating the show.
"But why would you want me to do this? Is it something common?"
"It is relatively common. I heard couples often use toys like these to spice sex when they have gotten bored of normal sex."
"Oh? Are you already bored of having sex with me?"
She realized her mistake and looked panicked.
"No! Never! I, I was really just curious about it! This is just a fantasy of mine, please believe me!"
She spilled the truth in her panic, afraid that she gave him the wrong impression. Seeing her reacting so strongly, he felt bad about teasing her like this and comforted her.
"I was just joking, I believe you, don't worry."
"Really... You scared me."
"Sorry, sorry. Anyway, should we get to it? How should I do it?"
She went to the bed and indicated for him to sit on the edge.
"You can sit here. Can you first masturbate normally? We can use the toy later on. Fortunately, you can come multiple times in a short amount of time."
"Alright."
Unsure of how things would turn out, he decided to simply remove all his clothes as usual. Even after so many times together, Sasha seemingly never grew bored of seeing him removing his clothes and lusting at the view of his nude body. She was watching him intensely, a predatory expression on her face, even sometimes licking her lips unconsciously.
Once he was done, he sat at the edge of the bed and she placed one of the infirmary's chairs in front of him. She sat on it and had now the best VIP seat possible for the incoming show. She locked her lecherous gaze on his penis and he soon started, understanding her implicit message.
He spit in his right hand and put his palm on his rod, slowly moving it up and down to start masturbating. She quickly queried him, seemingly curious about the process.
"Can you explain in detail what you are doing and how it feels?"
He wasn't sure what she wanted to hear. For better or worse, male masturbation was a very straightforward process. What's more, the question was weird considering she was supposed to be the one who taught him how to do it in the first place, as well as the fact that she had given him many handjobs in the past. Still, it seemed that today would be a day to realize another fantasy of hers and he didn't mind indulging her a little. She had always treated him well, even if lustily at times, and he rarely had the heart to refuse her small wishes.