Dave stared as the woman pumped lubricant onto that shiny glove that he'd seen reached up to her elbow. What the hell was going on? A slow learner perhaps but smart enough to realize that if he tried to ask again that it'd hurt, he finally turned his eyes back up to the ceiling. He couldn't bear to make eye contact with this woman he'd never met, this... this outsider. He recognized how silly it sounded, he knew it. After all, he'd come here and paid a stranger to do things, unbelievable things to him, but for some reason, it seemed different when it was a non-professional, an outsider like him.
He knew he should probably figure this out, that maybe there was something else going on here with how he was looking at these two equally unfamiliar women so very differently. Did it make a difference that one did this for a living and the other wasn't? Wasn't a sex worker? At some level, he was being irrational. That was clear, but-
"-and then slowly push in," he heard at the same time something cold touched his well-used hole and he jumped in surprise. He'd been so distracted by that line of thought that he'd missed the next step, the part where Nurse Violet had moved her 'lesson' to the next stage. Lifting his head again, he saw that the woman had her gloved hand between his legs just out of sight and was, as he'd expected, pushing what felt like one finger up his ass.
"My dear, we're past one finger. Have you seen what that little rosebud has taken this evening? Here, pull out and arrange three fingers like this." She demonstrated.
"Ok, I just didn't want to..." the woman's voice faded as she concentrated on putting her index, middle, and ring fingers together. "Ok," she continued, reaching down again, and he felt a new presence at his entrance, "here we go." After a moment the longest of the three slid back in easily but as the other two simultaneously began to push in, the pressure on his ass increased.
"You might need to wiggle them a little... good," the Nurse praised as he felt all three slid into him. The woman, the... civilian, she made a quiet sigh that he couldn't decipher as she pushed and pushed until he could feel the remaining curled digits pushing against his anus from the outside.
"I'm inside of him!" she breathed. He snuck a glance and could tell she seemed flushed. He looked back up at the ceiling, stricken. Another woman was inside of him.
"That's good! Now let's do a little bit of stretching. He's taken some big things tonight, but we need to remind that ass of his who's in charge and get it ready for more. Work your fingers in and out a little and give your wrist a little twist, we need to do some stretching."
She began to do exactly that and he began breathing a little harder. Suddenly, he jumped as her linked fingers brushed against his abused prostate and felt his penis twitch. Somehow, it had begun to grow again and with that unexpected touch, he could feel it rapidly hardening.
"He squeezed! Hard!" the woman gasped, holding still for a moment.
Nurse Violet chuckled in her low voice. "I think you may have pressed his little button. Take a moment to feel around, it's... maybe the size of a golf ball? Walnut? It's good to recognize, and they're ever so useful especially when we're looking to empty out his testicles."
Dave gasped as the wiggling fingers in his bottom touched that sensitive gland again and then again.
"Every time I touch it... Wow!" The woman seemed to be marveling at his twitching and squeezing at the command of her fingertips. He risked another glance and was mortified to find her staring at his penis twitching and dancing in front of her face as it flopped around each time he tensed his pelvic floor muscles in response to her probing. He looked away.
"Like a button," the nurse repeated, a smile in her voice. "Now let's move on. Curl your fingers a little and let's see what you can scoop out into this pan.
The pressure in his ass changed and a moment later, her fingers popped out stretching him even further than before as they dragged something out. He heard a liquid sound and felt something running down his cheeks. His eyes popped open in horror, he hadn't just-
"Oh my yes, Miss Esperanza always leaves such a nice present behind. I do so enjoy her visits, but we simply must clean this up before we let him leave, of course. Now like this." Dave realized it must have been cum she'd scooped out, and he barely had time to consider this before he felt a much greater pressure on his hole. He looked back down. While he couldn't see what the woman was doing exactly, he could see Nurse Violet holding her hand up to demonstrate, this time with all four fingers arranged together. The four fingers worked their way in and as her ad-hoc teacher instructed her, he felt her continue to stretch him even more. Two more times, she ended up 'scooping' out some more. Once in a while, she would brush against his prostate again and he'd squeeze her fingers with his ass involuntarily.
"And now, it's time for the big one. Are you ready?"
He looked over towards her, ready to shake his head, but then saw that she was asking the woman with four fingers buried in his ass. The woman looked a little nervous, but she nodded her head.
"Very good, go ahead and pull out but once we've got more lube on there, we'll need to get back in before he has a chance to undo all your hard work." Dave glared at the women in outrage. HE was the one doing the work, he felt, but he wisely kept his counsel to himself.
Showing her where to squirt extra lubricant, Nurse Violet gestured back towards his ass indulgently as if it was her possession and invited the woman to fully enter him. Showing her how to bring all fingers plus her thumb this time to a point, she pointed and a moment later, he felt her re-entering his ass. The pressure grew and grew as she pushed. He glanced down to see the intent look on her face as she both concentrated and pushed harder and harder. He groaned as the force built and suddenly she looked up and the worst thing happened; he made accidental eye contact with her.
A wave of adrenaline burst through him and he gasped and must have involuntarily relaxed something because suddenly the widest part of her fist, her knuckles, slipped past the ring of his ass and then her arm was pushing into his rectum.
He grunted as her whole fist squeezed past his prostate and all of the muscles in his body felt like they were tensing as he flexed in his restraints. The feelings were indescribable and, his eyes rolling, he twitched in place as a stranger's arm stuck out of his asshole and her entire hand was inside of him.