People on punishment are treated like potential criminals

Reaching for your book you start to write. You’d been using old rules so much that all of these experiences that seemed new to you weren’t really new to her at least in her mind. You wanted this to be new for both of you. You also felt forcing sex on her or even making it seem she was obligated to was a step too far at least for now.

New rule: all students on punishment are treated as at risk for criminal behavior. They must undergo mandatory cavity searches at least every day by their master.

You put away the book and Sarah looks nervous.

“I can’t believe they instituted that new policy. I mean what do they think I can really hide? I’m not a criminal just a bad student and I’m already naked!”

“I know, it’s not fair. I wish I didn’t have to.”

Sarah looked upset “I’ve never been touched before. You know that. This isn’t really what I was expecting.” She said trying to laugh about it but feeling overwhelmed.

“I know you would be anyway but please be gentle.”

“Of course. I’m sorry this has to happen.”

Sarah started to speak “at least...” and then stopped.

The thought that she was about to say “... it’s you.” Entered your mind. You really hope that was what it was but you’re too nervous to ask.

You grabbed her hand and guided her into a classroom that was unused to give you two as much privacy as possible. There was still a camera so they would know it’s been done.

“Are you ready?” You ask.

“No or I never will be I guess but, this is as good a time as any.” She said.

“Okay, let me just see the inside of your mouth please.”

She opened it and said “ahhh” and you looked but then you put your finger in her mouth to feel around. She looked uncomfortable but didn’t complain. After removing your finger and she rubbed one foot against the back of her calf nervously.

Her boobs were not large enough where there was a lot of underboob but she could potentially hide something there.

Reaching for her breasts you think again “do you want me to or can you...”

Looking away from you with shame she grabbed each of her nipples and lifted her breasts showing nothing was hidden. Her nipples seemed to harden and your penis matched.

Now on to the better parts you thought.

“Try to get as comfortable as possible.”

“Umm... where do you want me to be?”

“Why don’t you climb up on this table?”

She climbed up and got on all fours with her legs slightly parted. Already having the perfect view of her pussy and ass, you couldn’t help but push it further.

“Sarah... I need you to spread your cheeks for me. I’m sorry I just can’t see that well.”

She sighed heavily but reached back with a hand on each ass cheek and spread them giving you an incredibly lewd view of her anus and pussy. You could see her ass resting on her bare feet with a hand on each cheek and her wet pussy and pink butthole.

“Just... make it as quick as possible.”

“I will. Just take a deep breath there might be some pressure.”

Reaching for her labia with one hand you placed the other on her ass cheek. This was going to be the first time you touched a woman intimately and you were nervous yourself. You paused.

“Michael, it’s okay, really. Neither of us want this and that’s why it’s okay. You’re a really good friend and I honestly wouldn’t pick anyone else if I absolutely have to do this.”

You feel guilty but not enough to stop.

“Okay I’m going to start now.”

She took a deep breath and her pussy was wet enough where you didn’t need to go very hard to get two fingers in. She gasped and moaned loudly. You could feel her pussy start to contract around your fingers and you question whether trying to make her cum would make things better or worse. deciding she might be more attracted to you if you can show her you know what to do you wiggle the two fingers around inside her as she moaned lightly. You moved up and down and around ‘searching’. You continued to probe deeper and deeper and you could see her asshole start to contract as her pussy got wetter and wetter.

“Michael, please, I know it’s not my place and you’re my master but if you’re satisfied that my vagina has been thoroughly searched, please stop i’m going to...”

You thought you were doing the right thing but apparently not. You pulled out your fingers from her pussy and it quivered a little. She was breathing heavily and was practically shaking but still held her cheeks spread as she was told.

“Are you okay?”

“Yeah, just didn’t expect it to... have that sort of effect.” She said still panting.

“Okay, I didn’t mean to make you... feel any sort of way.”

“No honestly, if it were by choice that would’ve been... special. It’s just not and I didn’t want my first... you know... to be under these circumstances.”

She called it special. That had to be a sign but you were still kind of nervous. She was naked and completely at your mercy but it felt like she was the one in control.

You placed the fingers that were still covered in her juices at her anus and she jumped nervously but then calmed down a bit. You could see her closing her eyes and taking deep breaths.

“Master, I trust your judgment just do we need two fingers? Please don’t hurt me.”

She was practically cowering and called you master. clearly she was feeling so uncomfortable she felt she had to be extra cautious.

“Why did you call me master?”

“I just... I know you didn’t ask for this but I also know that you’re the one in control here. I’ve never had someone touch me there and to be honest I never wanted to. I just know guys really like it back there so I was hoping to be as respectful as possible asking you not to... hurt me.”

You respond “Sure I can do just one finger. Just don’t call me master please. I know it doesn’t seem like it but we’re equals.” trying to appear as caring as possible. This whole conversation happening with her on a table, naked, spreading her ass while you held two fingers on her anus.

“I’m only doing this because if I didn’t someone else would.” You lie and feel bad but this is Sarah and you’ve been dreaming about this sort of thing since you hit puberty.

Removing one finger that had been touching her back door you take your middle finger and place it against her asshole.

“Are you ready?”

“As I will be. Just don’t... hurt me. Please.”

You slowly and as gently as possible push against her ass with your juiced up finger. You hear her grunt and she’s starting to clench around your finger as it gets very slightly inside her.

“Are you okay?”

“No, yes, i don’t know... it’s not you. It’s the situation. Just hurry please.”

You push harder and you get in up to the first knuckle and she grunted and yelped. Rubbing her back with your free hand you hope to calm her down a bit. You keep pushing as she clenches involuntarily around your finger. She seem to spreading her cheeks even more trying to add to her comfort. You get to the second knuckle and she’s biting her own lip to not whine. You take your spare hand and place it on her right hand which is spreading her right ass cheek. She grabs it and squeezes hard as you finally get to the base of your finger. She lets out a loud sigh as there’s no more finger to insert. You gently probe around her rectum for a while and she holds your free hand the whole time.

“Michael, please...”

You pull your finger out very slowly and her asshole closes shut as you get it all the way out.

“Sorry, I just don’t want to lose you if they think I’m not thorough enough.”

Patting her gently on the butt she gets up off the table and her legs are wobbly. You catch her as she starts to fall. Holding her up as she leans against you, she looks into your eyes and then away.

“Sorry, I just need a moment.”

“How do you feel?”

She swallowed nervously having to discuss her intimate areas “The front place feels fine, the back one is a little tender. Don’t worry, I know you did your best.”

Not knowing what to say you said “let’s get to class.”

“Okay.” She said looking down at her nude body and sighing obviously hating her exposure.

A voice in the back of your head says “make your move.” But you’re not sure the time is right. You hold her up by her back as you make your way into the corridor and then the halls which are empty because you’re running late.