She thought for a second before fetching the bottle of lube and giving both items to him.
"Can you try to use it and tell me how it feels?"
"Alright."
Now that he had the "fleshlight" in hand, he could thoroughly inspect it. He put the lube on the bed and took hold of the toy with both hands, turning it around to see all it had to offer. He soon concluded that there wasn't much to it. He noticed that the side which didn't have the silicone opening was closed. The only other interesting part was the other side which was in the form of female genitals. He used one finger to rub it, trying to get a feel for its texture. It felt soft, flabby, and cold to the touch. He then inserted his finger inside the opening and could feel that they had tried to reproduce the folds of women's vaginas, the silicone inside taking the form of small bumps and waves. The feeling was quite far from a vagina, even though the soft and flabby texture was relatively accurate. As expected, it lacked both the warmth and the fluidity of a pussy. He could probably get the fluidity with the lube, but the coldness couldn't be helped.
Seeing him putting his finger inside the toy seemed to resonate well with Sasha, who looked at what he was doing with a very interested and lustful expression.
It was now time to start with the main act. First of all, there was something he wanted to try. He took the toy in his right hand and his cock in his left hand. He then aimed his glans at the hole and slowly inserted himself inside it. As expected, there was a lot of friction when not using the lube, the unpleasant kind. It was hard to move deeper and it kind of hurt too. He now understood that some sort of lubrication was completely expected and the toy wasn't made to be used as is.
He removed himself from the hole and took the bottle of lube. Now, he wondered what the correct process was. Since he didn't know, he chose to ask Sasha about it.
"Should I put the lube on my penis or inside the silicone?"
"Hm, I'm not sure either. What about you do both? Don't worry about the quantity you use, I can just buy more later on."
He wondered if she had plans to make him use the toy regularly from now on. Listening to her idea, he put some lube inside the hole and some on his hand, which he then applied to every corner of his member. His dick was now glistening with the lube and Sasha looked very satisfied at the view.
He took back the toy in one hand and his penis in the other and tried inserting himself once again. It was much smoother now and he was able to go in without any issues. It felt relatively good, the small bumps of silicone inside acting as expected to provide more stimulation and everything feeling very sticky. When he reached the bottom of the fleshlight, he hit a wall of silicone, which was probably the equivalent of the deepest part of a pussy. Overall, it felt okay and it wasn't bad. At this time, Sasha reminded him of his "duty".
"How does it feel?"
"It's alright, I guess. It feels bumpy and sticky and pressing my glans against the deepest part feels good."
"Oh, I see. How is it compared to my vagina?"
He didn't even need to lie because the differences were obvious.
"It cannot be compared. It lacks both the warmth of it and the small movements and contractions you would have when I am inside you. The feeling of stickiness also feels quite different from the feeling of wetness inside you and the pressure is also less."
When he was done explaining, he could see that she looked very happy at his comments. He moved the toy up and down a few times to better understand it.
"Having complete control of the act is nice but that's the same as with masturbation. Overall, I would say it feels a bit better than masturbating with my hand but that's pretty much it."
"I understand. Do you still want to go all the way?"
"Well, why not, I should try it at least once."
He continued to move the fleshlight up and down at a regular pace and Sasha observed everything with a piercing gaze. Still, she seemed a bit disappointed and he asked her about it.
"What's wrong, Sasha?"
"Well... Don't get angry after I asked you to do it but it feels less interesting than I thought because the interesting parts are hidden most of the time."
This made sense. From her point of view, she mostly only saw some plastic going up and down over his groin. She thought for a second and added.
"Perhaps it would be better if I did it for you instead. Can I?"
"Go ahead."
He stopped what he was doing and she came to sit next to him on the bed. Her hand replaced his on the toy and she began to move it up and down at the same pace he had been going.
"Now that I am not in control anymore, it feels a bit more exciting."
Hearing his words, she accelerated her movements and he sighed in pleasure. Seeing this, she also commented.
"Yes, it's more interesting like this."
As expected, a minimum of interaction made things more thrilling for everyone during sexual acts. Progressively, she increased her speed, and the noise of his dick rubbing against the lubed silicone resonated in the infirmary. She was closely monitoring his reactions to her masturbating him and seemed pleased by the view. Eventually, he reached his limit and announced it to her.
"I am going to come soon."
She switched to using both hands now, suddenly going as hard as she could on him. The toy stimulated him several times per second and he couldn't hold on anymore. He came soon after that, grunting his pleasure in a low voice. She pressed the toy as deep as she could on his dick, appreciated one jerking ejaculation, moved it again hard one time, and pressed it all the way once more, in repetition, until he was completely spent.
When there was nothing more to extract from him, she finally removed the toy from his cock. They could now see that it was glistening with both lube and sperm, creating a great scenery for Sasha who looked at her work appreciatingly.