The Janitor Pt. 02: Willing Bookworm

The Bookworm (anal in the library)

The usual disclaimers: this story takes place in a high school but everyone having sex is over 18. No STD'S, COVID or unwanted pregnancies rear their ugly heads.

Mike was whistling as he moved the buffer across the floor in a geometrical pattern. It was mindless work which was a good thing. Ever since his encounter with the two girls in the school laundry room he had been distracted. He had 'caught' them three more times and got to watch some sweet girl-on-girl sex. The last time they had a new girl with them who seemed to just love getting reamed with a huge strap on dick. He was looking forward to the day they were all on birth control. In the meantime he whistled while he worked.

He got to the end of the hallway and parked the buffer in the janitor's closet. He consulted his list of chores for tonight and saw that waxing the library tables was next. He grabbed the carryall tray with the things he needed and headed up the stairs. He walked into the library confident that he would be alone. It was nearly 5:30 on a Friday evening. There were no clubs or practices on Fridays and the only athletic contest was an away baseball game.

He pulled the chairs away from the wide table and ran two lines of liquid wax down it's length. He carefully spread the wax in an even coat then moved to the next table and repeated the process. When the wax was spread, he moved back to the first table and used an electric buffer to polish the wood. When he was done, he used a soft cloth to buff the wood bringing out the grain which made the wood seem to glow. He enjoyed polishing, it was satisfying somehow. He worked his way around the room alternating between tables.

He finished the tables and took a break to hydrate. There were two more tables to do in the back behind the stacks. They were large round tables reserved for study groups. He turned at the last stack and nearly ran into a young lady bent over the nearest table. She had her top on but was naked from the waist down. Her legs were very long and had a great shape to them. The butt definitely had a nice shape also.

He was wondering how she hadn't heard him buffing the other tables when he noticed an expensive pair of Bluetooth earbuds in her ears. That certainly didn't explain why she was bent over with her jeans neatly folded on the table and a red thong on top of them. She was looking down at an open laptop and seemed engrossed by whatever was on the screen.

Mike put down his equipment and slowly eased to the side so he could see the screen. He was both shocked and amused when he saw the girl was watching porn. Not just any porn but anal porn. As he watched a new scene came on causing the girl to moan and reach one hand behind and squeeze one of her cheeks. As she did so it opened her up and Mike saw an emerald butt plug pulled tight to her asshole.

"That's right," the girl said aloud, "I have a jeweled butt plug up my ass."

Mike nearly jumped out of his skin when she spoke but soon realized she was still unaware of his presence and was talking to the characters on the screen.

"Yes, it is the large one, over two inches in diameter and heavy. You wanted me to stretch out my butthole for you, didn't you?" the girl enquired of her laptop.

Mike was impressed by the girl's detailed role playing. It was obviously not the first time she had watched this video. He looked more closely at the video and realized that he too had seen this one. It was about a girl who was working late at a bank and gets taken by the janitor.

Mike wondered whether the girl would freak out if she saw him or want to continue the fantasy in person. The young lady answered his question by saying, "Oh I wish you were here in person; I want my butt reamed so badly. You would know what to do and like it, not like the idiot boys I have asked."

She whimpered now as the couple changed positions and the actress sat her ass down on the huge porn cock. One of the junior officers of the bank came into the picture. Without a word he unzipped and stuck his hard dick in the pussy of the woman riding the horse cock.

"Oh yes," his little cutie moaned, "Fuck her in both holes and come at the same time. Do it, do it now."

As the actors all came at the same time, on the table the girl used one hand to strum her clit and the other to pull and twist the plug in her ass. It didn't take her long to join them in reaching a climax. She sighed and closed her computer and slowly started to stand up. Mike figured it was now or never, so he stepped up behind her then used one hand to bend her back down onto the table.

She screamed but didn't try very hard to get away. She reached one hand up and pulled the earbuds out. She started to turn her head and Mike quickly used his other hand to keep her looking forward.

"Damn it Terry, I told you that you blew your chance at doing anything with me last week," the girl said angrily.

Mike shifted his free hand down and caressed a firm butt cheek before using it to spread her open. The green jewel winked at him as he stared at it. He gave it a little tap and got a small moan from her. He gripped the edges and gently pulled on the plug. He saw it start to stretch her hole open and quickly tapped it back into place.

"Oh fuck, don't think you can just come in here and pretend to like playing with my ass Terry" she said sternly then spoiled the effect by moaning loudly, "let me go now."

Mike casually used his hand to spank her. At first she yelled and tried to squirm away. By the time he had given her five on each cheek she had settled onto the table and seemed to be resigned to her punishment. He paused and wondered what his next move was.

The girl wiggled her hips and complained, "Why did you stop, it was just getting interesting."

Mike grinned and pulled her backpack over. One handed he searched her bag and found a twelve-inch wooden ruler near the bottom. He held the ruler so she could see it out of the corner of her eye.

She tried to nod then said, "What the hell has gotten into you today?"

It sounded like a rhetorical question so he didn't bother replying. Instead, he used the ruler to rhythmically turn her ass a bright red. At first the girl squirmed in pleasure but by the end she was wriggling trying to get away.

Finally she gasped out, "Oh please, please stop it's too much."

Mike threw the ruler down on the table right in front of her nose.

"OMG, I'm surprised there is not blood covering it. It feels like I should be bleeding," she exclaimed.

Mike rummaged in her bag for a small tube of lotion he had noticed earlier. He squeezed a healthy dollop onto each cheek then started gently rubbing her abused ass.

"Use both hands please, I won't try to look. I know you're not my asshole ex but I need you to cool my ass down before we do anything else. Are you going to talk to me or just silently torture me all night?" It still sounded kind of rhetorical, but he answered her anyway.

"Sure, we can talk. What is your name would be a good starting point I suppose," he offered.

"Cassandra, my name is Cassandra," she told him, "Although why a mad rapist would want to know my name is a mystery."

"Hi Cassandra, my name is Mike, I am neither mad nor a rapist."

"Then why are you holding me bent over a table with my privates on display? And call me Cass."

"Well, I didn't want you to see my face in case you were the type of girl to kiss and tell. Now that I know how much perverted fun you like to have, I guess I can let you up."

With that he let her go and jumped back away from the table just in case she had something planned. Instead, she picked up the lotion and waving it behind her asked him to rub her ass some more. He did as she asked and soon she was purring like a kitten.

"I have a question," Mike said as he continued to rub her butt, "Why are you watching porn in the school library? Are you homeless or something?"

"I come in here after school to get my homework done. My mom runs a daycare out of our house, it is impossible to study until the rug rats go home. I finished and was horny. I figured this time of night it would be safe. I never thought a perverted creep would attack me."

"Yet here we are. You want to straighten up and maybe put your pants on?" he asked.

Cassandra slowly stood up then stretched to get the kinks out. She turned and looked at him and grunting said, "At least I am being molested by a decent looking guy. You are going to molest me some more, aren't you?"

"If that is your desire, sure, why not?"

"Jesus, don't sound so enthused about it. Just my luck, an apathetic molester."

"Well, I'm certainly going to think about it but first things first. Can you show me a valid ID that states you are over 18? Are you expected home at a set time? Will you let me remove that plug with my teeth? Can I fuck you in the ass?"

"Ok. In order: yes, no, yes and I thought you'd never ask."

"Oh goody, let's see the ID first my lovely."

She produced a current driver's license from the state they were in. It listed a local address; he was surprised to see she lived on the next street over from him.

"All right, that checks out. Another question, why would your ex not fuck that gorgeous ass of yours?"

"He seemed to like the idea of fucking me until he realized I only wanted it in the butt. He bolted when I asked him to put a finger up my ass."

"So, I take it you've have regular, I should say vaginal sex, with a male partner before?" he inquired.

"Oh sure, I've given blow jobs and had a dick in me a few times but can't find anyone that wants to try anal."

"Jesus," Mike mumbled, "we are raising a generation of fucking idiots. Who could look at that ass and not want to pummel it?"

"I have a theory on that. All the guys I asked to do me were anal virgins. A few of them were vaginal virgins and Terry, my ex, I think was a hand virgin. His own hand I mean. They were all afraid to try something and be made to look the fool. Boy's egos you know."

"There might be something to what you say. I got lucky with my first serious girlfriend. She loved it up the ass, a good Catholic girl that was terrified of getting knocked up like her three older sisters. I may be a little jaded, who knows. Ok here's the big money question, where did this desire to have anal sex come from?"

"Well, it's not really a desire," Cass explained, "it's more of an obsession. I hooked up with a guy at a pool party. We were both drunk and started fooling around. We finally found an empty room and made out for a bit, he got my bikini bottom off then went to town eating my pussy. He was really into it, soon he was going from my clit to my butthole. I told him I really liked his tongue back there and he concentrated on my asshole. He got his tongue way up my sphincter making me come. I told him he could fuck me there if he wanted.

I got on my knees, heard him getting in position then nothing. I looked back and he was passed out with his swimsuit at his feet. I tried to wake him, but it was no use. I put my suit back on, got my stuff, said my goodbyes and went home. I have been obsessing ever since."

"When was this?" Mike asked.

"Six weeks ago," she replied, "I went to the sex store and got this set of four jewel plugs, this is the biggest one. I bought an anal dildo, beads, a hook and some other stuff."

"Yeah, that pretty much describes an obsession I guess," Mike said with a chuckle, "so, anything I should know before I ravish you? Kinks, taboos, oh yes please, not in your lifetime?" he asked.

"Not really, why, do you have something special in mind?"

"Besides giving you several mind-blowing ass orgasms, not really. Is your pussy off limits? Do you go ass to mouth?"

"Oh yeah, you can use my pussy. I really want your cum to wind up in my ass, however. One of my favorite videos has ass to mouth in it. I would be happy to try it unless your cock comes out of my ass absolutely covered in shit," she informed him.

"Next question, do you want to do it here or go down to the laundry room where we could get more comfortable?"

"Not down there please. When I was in Home Ec earlier this year Nancy McGovern tried to feel me up when we went to fold towels," she shuddered.

"Right, bent over the table then. Can I pull your plug out now?"

"It's funny, it's really tight, but if I move around it feels like it will slip out of my ass, but it never does. If I wear it all day at school, sometimes at night I have a hard time removing it."

"I do love a challenge," Mike said smiling.

"Wait a sec," she said and pulled her hoodie and T shirt over her head. To his surprise she wasn't wearing a bra. She had small B cup tits that had no sag in them.

He put his hands on her shoulders and turned her to face the table. She bent over and spread her legs without a word. When she was lying flat, she reached both hands back and spread her cheeks. Mike went to his knees and started kissing and licking her ass. The lotion was well absorbed but still left an odd oily taste in his mouth. He moved in and licked all around the plug. He could smell her ripe pussy. He didn't hesitate in dipping down and tasting her nectar. His tongue parted her lips before he nibbled and sucked on them while using a thumb on her clit. Cass shivered then started to giggle. He stopped, asking her what was so funny.

Still giggling she said, "This is the first time anyone has kissed my pussy lips before he kissed my face lips."

Mike laughed and resumed his journey of exploration. He soon had the entire area surveyed and went to work on removing the plug. He tried pulling it out with his teeth but got nowhere. He gave up before he needed upper and lower dentures. He tried just pulling on the jewel with steady pressure. It seemed to be working at first then Cass told him to stop, it was too painful. He took the lotion and tried to get as much in her rectum as he could around the narrow stem. That seemed to help but still it wouldn't come out.

"Ok, you're going to have to squat down on your heels. That should give us a better angle, the body naturally loosens up in that position," he told her. He took ahold of her hips and pulled her back until she could stand. She squatted down hanging onto the edge of the table for balance. He got to his knees behind her then thought better of it and scooted around until he was sideways to her. He used one hand to rub her pussy and clit while the other hand applied a steady pull on the plug. He kept pulling, when it was nearly at its widest point his hand left her pussy and found a nipple that he pinched as hard as he could. She let out a shriek and the butt plug was ejected from her ass. Cass lost her balance and fell into him. He was off balance as well and they wound up in a heap on the carpeted floor.

"My hell," Cassandra groaned, "that hurt and felt incredible at the same time. Thank you. Quick thinking on the nipple grab btw."

"You're welcome, I was highly motivated to get that monster out of your sweet ass. Now I can plug it with something else."

"Hang on just a minute Sluggo," she said as she got herself twisted around so she was sitting in his lap. "I want to check out the goods before you just pop it into my tender little butt."

"Sluggo? Who or what is a Sluggo?" he demanded to know.

"Nancy was a comic strip in the newspapers, it ran from 1938 up to 2018. Her boyfriend was Sluggo. My grandpa was a huge fan and had scrapbooks filled with old strips. I learned to read from them. It was around for eighty years, you never heard of it?"

"Now that you mention it sure, they had round faces and she had frizzy hair."

"Very good, if you had failed the Sluggo test I would have been so out of here. So, get the duds off, let's see what you got there pal."

She was a fairly small girl, but he struggled a bit to gather her in his arms and stand up. He deposited her on the table then made a small show of stripping for her. When he was naked, he stuck a body builder pose. She laughed and applauded then held her finger up in a stirring motion, so he did a slow turn for her.

"I was thinking I could get you to fuck my ass then get out of here. After seeing you naked I want you to lick me some more, then fuck my pussy, then deflower my tight teen ass. If that takes a couple of hours would you mind?"

"I am more than willing and capable of catering to your every whim madame. Command and I shall obey."

She smiled and shook her head. She gathered her clothes, stuffed them in her backpack then used it for a pillow.

Mike got down on his knees and pulled her hips to the edge of the table and went to work on her sweet pussy. He had Cassandra writhing and moaning in no time. Her first orgasm came two minutes in, her second was nearly a continuation of the first.

"Holy shit, if you can make your dick perform like your tongue, we're getting married," she exclaimed then added, "I'm sorry, that just came out. I didn't mean that. Shit, no wonder I don't have a boyfriend."

"Did you say something?" Mike said with a straight face, "I was thinking about what font to use on our wedding invitations."

"We're just getting started and this has already been the best day and the best sex I've ever had," she said as she playfully slapped his arm.

"Well then, it's time to give your pussy a taste of cock," Mike said as he got to his feet.

"Did you want me to suck it to get it hard?" Cass asked.

His response was to insert his rock hard cock in her pussy and bury it deep. He held it in her, looking in her face for a reaction. She stared at him with a huge grin then used her internal muscles to give him a hello squeeze.

She quickly proved that she was capable of vaginal as well as clitoral orgasms, over the next ten minutes she proved it four times, but that was her limit.

"Please, oh please stop. I can't take any more," she begged.

Mike was out of breath and couldn't tell her that he was fine with stopping also. He lowered himself to the floor and rested his head on her thigh. She reached down and ran her fingers through his hair. They had rested like that for about five minutes when Cass grabbed his ears and gently pulled on them. Mike slowly got off the floor then stood between her open legs.

"Time for the main event," she said as she brought her knees up until they were on either side of her head. This tilted her hips back and gave him a lovely view of her ass.

"Is this how you want to do it?" he asked her.

"Yeah, I use my dildo in this position, it goes in easier. Plus, this way I get to see your ass fuck face," she giggled.

"I know you want this, but I think some lube would be a good idea. Do you have something other than that lotion?"

"Oh shit, I forgot," she said as she took the backpack from under her head. She opened a side pocket and handed him a tube of lubricant.

"You do know this might have been useful when we were trying to get the plug out, right?"

"I was so excited about finding someone that is into butt stuff I forgot completely, sorry."

"Well, I wasn't the one in pain so it's on you."

He used liberal amounts on her ass, amused by how much she enjoyed one, two then finally three fingers.

He pulled his slippery fingers from her then added more lube to his hand slowly stroking himself.

"As much as I have been using toys to prepare for this, I'm probably loose enough for what I want," she told him, "I want you to put it in me and just keep going. I want you to bury your cock in my shitter in one stroke, okay?"

"Fuck yes it's okay. I want to watch your eyes get bigger and bigger as I fill your ass."

"Then do it, do it now you pervert," she told him.

Mike followed her orders and slowly sank his cock into her ass, her eyes did get bigger the deeper he went. In just seconds he was balls deep in her tight warm ass.