Teaching Intent Ch. 03: Caitlin

Cindy Condor was sitting at her kitchen table looking at her phone. She jumped back and forth between two different websites, trying to take in all the information so that she can form a decision on what to do. One was an online gradebook for 18-year-old daughter. Her grades were lousy. C's in English and Spanish, a D in science, and an F in math now that he entered her most recent test.

The other website was her daughter's Instagram account. She had hundreds of photos of herself posted there, all of them publically available. Scanning through the photos Cindy noticed that her daughter rarely wore an outfit that covered her navel. Sure there was the occasional dress, mostly from school dances, but those were compensated but exposing her cleavage and being ridiculously short.

The other thing that struck Cindy was the sheer volume of bikini pictures that Caitlin had posted. Caitlin appeared to own an unnecessary variety of bikinis: a purple top with a bright white bottom that tied together on the sides, a top and bottom with a matching floral pattern, a black one that could pass for underwear, a red top paired with a low rise white bottom that had a thick strap that wrapped around her side, a top with a butterfly top paired with an orange bottom, a blue top wore underneath a life jacket, a bright yellow top paired with a bottom that had pattern resembling autumn leaves, another leaf pattern but these bottoms had the front and back connected with a gold ring on her hip, a tie-dye looking one with pink and white blotches, a teal one that looked like the back was a thong, a solid green one, a bright red one, a blue one with white streaks that looked like the surface of the water when viewed from below, a white one with a large image of pink lips on the fabric covering her left tit, a strapless white top with a small viewing window between her breasts, they just kept going. It was all too much for Cindy to take in at this moment.

And she seemed to wear them everywhere: sitting on a dock, on their boat, an underwater scuba diving shot, at the beach, in a pool, in her bedroom, in the family bathroom, at a friend's house, in a car, at the tanning salon. This certainly explained how her once pale daughter was now so tan. The girl seemed to live in bikinis this summer.

Caitlin walked into the room as Cindy was scrolling through her various bikini pictures. Of course her navel was exposed again, actually nearly her entire chest was as all she wore on top was a black sports bra. On her hips she wore a pair of tight black leather shorts.

"What are you wearing?"

"I'm a bunny rabbit," Caitlin responded as she pointed to her headband with large black lacy ears. Caitlin took the seat across the table form Cindy to put on her women's lug-sole combat boots. "I'm going to head over to Kayla's Halloween party."

Cindy looked back at her phone, an F on her math test. "Why don't go trick or treating first?"

Her daughter rolled her eyes. "Mom, I'm 18. That's a little old to go trick-or-treating."

Cindy sighed as she looked her daughter's outfit up and down. "I saw you failed your math test."

"Mom it's a Friday night, can we talk about this maybe on a school night."

"Your math teacher lives two houses down. Maybe if he knew you were his neighbor, maybe if he sees you more outside of school he'll go a little easier on you. Just a quick stop before you head to your party. It couldn't hurt."

"Yea OK," she said as she stood up. When she turned around Cindy saw how those leather pants tightly hugged her daughter's round ass.

Cindy pulled up her own Instagram account once her daughter had left. Just two years ago her daughter was this shy little girl that would never walk out of the house like that. Two years ago was the last time she had a student in Greg's class. She fucked him weekly to get her son to pass math.

Cindy saw Greg at the grocery store a month ago and joked, "I hope Caitlin doesn't need as much help as her brother to get through math." A true statement that sounded innocent to anyone that didn't know the full truth.

"It's important to me that Caitlin puts in the work herself, but I think she'll do great," was his reply. Cindy knew then to fear this moment although she didn't know exactly what she feared. She knew her daughter was far from a virgin. Shit some of the comments on her Instagram account were very explicit and then there were the sounds. Walk by her room any random time last summer and you'd hear some things. Sometimes she was having phone sex, sometimes she had a boy snuck in, but Cindy never had the guts to barge in and bust her. She was always so busy, off on her own affair.

Cheating on her husband with this math teacher was the start of a road that led to other affairs. Cindy knew she hadn't been around much and blamed herself. She used her palms to wipe away the tears before heading back to find her own slutty Halloween costume. Her lover would help her forget the pain.

* * * * *

Caitlin Condor passed a dad with his kids as she walked down the road. She noted that his eyes were locked on her as they approached each other. She smiled and said nothing to him.

The overgrown bushes at Mr. G's house helped with the Halloween aesthetics. She past the bowl of candy with the "Please take one" sign and rang his doorbell.

Caitlin grew uncomfortable as she waited. She hoped he'd answer the door before another group of children swung by. Maybe he wasn't home. There was a bowl out, but then there were two cars in the driveway. Maybe he was entertaining guests and didn't want to keep getting up to reach the door. Maybe people congregated at his house before heading in one car to a bar. How many of her teachers would be inside?

The door opened as she contemplated scenarios. Her math teacher, Mr. G, was wearing an outfit not terribly different from his normal classroom dress: khakis and a dress shirt. The dress shirt was also khaki with over half the buttons were undone so she could see his chest hair. He was hairier than she had previously imagined. His curly brown chest hair was especially noticeable on his light skinned chest. Across his chest was a strap holding a satchel on his hip. On the other hip was a toy pistol. He was wearing two belts, a light fabric one holding up his pants and a darker one that only went through half the belt loops holding his gun.

He had the stubble that he'd been growing all week that had crossed the boundary to a short beard. His wide brimmed sable fedora was pulled down to partially obstruct his eyes, and of course his mouth was formed into his trademark goofy grin.

"Trick or treat."

"Caitlin!" His voice squeaked and then he cleared his throat before continuing. "It's a good to see you. I'm glad you rang the bell instead of just raiding the bowl."

"Well I was looking for something sweet and your bowl here just didn't have what I craved."

He smiled as his eyes obviously looked her up and down. "I like your costume, but where's your fluffy tail?"

She lifted her heels off the ground and pivoted so that he could see her in profile. She raised one leg and gently touched her hair to strike a pose for him. Subtly, she sucked in her belly and pushed out her ass. "I'm not that kind of bunny."

"I think you might be my favorite type of bunny."

"How about you? You some sort of safari guide?"

He let out an awkward chuckled and turned away from her for a second. "Nah, I'm Indiana Jones," he said as he drew his fake pistol.

"Ah right, my dad likes him a lot."

"Not exactly the result I was going for."

"Maybe it would be if you knew how well I got along with daddy."

He stuttered for a bit, but never found the words.

"Do you mind if I come in for a minute and warm up?"

"Yea sure, come right in Caitlin."

She looked around after passing through the threshold. "I didn't realize how similar all the houses were in this neighborhood."

"Yea, I can imagine the assembly line where they build them all."

She didn't get his joke, but kept on smiling. He fidgeted with is hands briefly before leading her through the house to the living room where he stopped and looked around. Hocus Pocus was playing on the TV in the corner. There was a bowl of popcorn on the coffee table. A leather jacket was draped over a nearby chair.

"Were you just having a relaxing evening watching TV?"

"Yea, something like that," he said as he scanned the room like he was looking for the missing remote. "I'll probably head out once it gets dark."

"Will I see you at Kayla's party?"

He chuckled. "Nah, you don't want me there. I'll probably head out to a bar."

"You know in most countries 18 is old enough to go to the bar."

"So is that why you visited? Looking to score some alcohol for your party?"

"Not for the party, but I'd be interested in pre-gamming if you're offering."

He grabbed a bottle of vodka off his counter and a dark red juice from his fridge. She'd been drinking enough to know he put about half a shot's worth of alcohol in her drink. "This stays between us," he said as he handed her the drink.

"Wish my test scores would just stay between us," she said as she took a sip.

"Yea, sorry about that." He poured himself a significantly stronger version of the same drink. "Your parents check your grades recently?"

"Yea just got the talk before my mom sent me over here."

He smiled and swirled his drink. "Yea she was very involved in Pat's grades two years ago. She comes off as a bit of a helicopter parent."

Caitlin snorted. "She used to be, but she's been different the last year or so."

"How so?"

"She's always gone. I can't remember the last time she made it to one of my games."

"She get a promotion at work?"

"No, I think she's just having an affair."

Mr. G spit out some of his drink and started coughing.

"Shit it's not with you is it?"

"No, you just caught me off guard with that statement. That's got to be hard to deal with."

Caitlin shrugged. "It was at first, but I've learned a lot from it. Being prudish about sex only works if everyone else is too. But lower your expectations for everyone else and it frees you up to have a lot more fun."

"How's your dad doing?"

"I found him someone that keeps him satisfied."

"That's very... sex positive of you."

"He's just like you. He needed it even if he wouldn't admit it at first."

Mr. G put his drink down. "I find plenty of women to keep me satisfied."

She reached out and curled her fingers through his chest hair. "Is that so? Usually people don't dress up when they leave the bowl out. Someone else on their way over?"

"Actually I think she just left. Must've gotten scared off by the competition."

She laughed. "I don't think it's much of a competition." She patted the bulge in his pants. "You give your intentions away."

Her thick-soled black boots clanked loudly as she turned to walk away from him. Walking up to the back of his couch, she bent over and placed her forearms on the back of the couch. "Do you think it looks bad that I don't have a tail?"

She started scrolling Instagram as she waited for him. Marge had already posted a picture of herself in her angel costume with the caption "so excited for tonight". Caitlin liked it, the outfit was cute. It was revealing for what Marge normally wears: a relatively short skirt but longer than Caitlin's shorts and a strapless white shirt that still covered her stomach. Caitlin would've been in a tube top and mini skirt had she been an angel.

Caitlin spoke when she finally felt his hand on her hip. "So about that test grade?"

"I'm so sorry, I must have accidentally switched the digits. 38 and 83 are very different grades."

"I think you meant 100."

"100's are more suspicious."

Caitlin stood up and took a step away from him. "Sorry, but if we're going to do it then you really have to make it worth it."

He grabbed her hand before it was out of reach. "Fine, fine, fine. 100. Now give me a piece of that tail."

She spun to face him as he pulled her towards him. She tilted her head up to look as him as he planted a deep passionate kiss on her lips. His hands were all over her ass and in moments her shorts were pulled off her bubble butt.

She grabbed his shirt and ripped it all the way off. Two buttons went flying across the room. She then fiddled with his belt, but the toy gun instead of his pants fell to the ground when she got it undone. "I'm not used to men's outfits being this complicated."

He chuckled as he undid the other belt. Once his pants were down he grabbed her legs just below her bubble butt and lifted. She wrapped her arms around his neck as he sat her on the back of the couch. A moment later he slid her shorts down to her boots. She spread her knees as wide as they would go as he shuffled stepped his dick towards her.

She moaned loudly for him as his dick entered her pussy. "Oh you're so big. Something else you have in common with my daddy." Mr. G stopped pumping and loosened his grip on her. "Oh don't stop. Fuck me daddy."

He resumed pumping, but wasn't enthusiastic enough, so Caitlin pushed her body towards him. Unfortunately her ass slipped off the edge of the couch causing her to fall forward. His arms shot out and tried to catch her, but he ended up just breaking her fall as he fell with her.

Caitlin still banged her knee, but didn't let that pain slow her down. Moving was awkward as her boots and shorts kept her ankles bonded together. She climbed over him and lowered herself onto his still erect dick.

He laid still, watching mesmerized as she took complete control. Her body danced and moved like she was riding a bull in a rodeo. Her eyes seemed focused on some distant point. Her lacy bunny ears were askew but still on her head. Her black sports bra still firmly held her B-cup breasts in place. Her stomach muscles flexed and moved like a turbulent ocean. Her small deep navel was a whirlpool in the center of that ocean.

She was in such a daze that she didn't immediately notice when he came. She was staring at some distant point as she continued to robotically rock on his cock. He rubbed his hands up and down her bare chest and then up to her firms tits to keep himself hard.

She snapped out of her trance when he pulled her down for a kiss. She turned away so that his lips pressed against her cheek. He wasn't discouraged, but soon she raised herself off his cock. "I should get going to my party."

"Come on, one more trick before you go."

She sighed as she kicked off her boots. "Alright, but make it quick. You're not my only dance card tonight." She laid on her back with her legs spread and her eyes closed.

He placed his hand on her knee and slid it along her smooth leg. She was completely hairless from the neck down and every inch of her was tanned beautifully. His thumb lined the lips of her pussy while his fingers reached underneath and grabbed that ass meat. "Flip over, we'll fuck how rabbits do it."

He rubbed himself as he watched her silently comply. She flipped over on her elbows and knees so that her ass was presented before him. His hand rubbed her ass before he brought his hips up to hers. His dick easily slid into her wet pussy.

His hand rubbed up and down her spine. Her back was cold, a stark contrast to the warmth his dick felt between her legs. His hand found its way back to her ass where his thumb curiously circled her asshole. He pressed against it and she moaned. He realized that was her first moan of the night.

He moved his index finger to the hole and pressed deeper. She gasped loudly. He smirked at having knocked her out of her trance. His hips picked up rhythm as he pounded her pussy. Her pussy was significantly wetter now that his finger was in till the second knuckle.

He pulled his finger and dick out of her when he felt himself getting close to cumming a second time. Grabbing her on the hips he lined his dick with her asshole. It was dripping her with her juices, but he pressed slowly as he inserted his dick into her ass. She groaned and grunted, but said no words to him. Her asshole was so much tighter than her pussy so he kept his motions slow so as not to hurt her.

He pulled out again when he once again felt himself getting close to cumming. He stroked his dick vigorously, his hand gliding easily along the surface thanks to all of her wonderful juices. He aimed to cum right on the top of her ass to give her a white tail to finish the bunny look, but the initial spirt shot all the way across her back.

She walked over to his bathroom to clean herself up while he rummaged through her stuff. She didn't have much to go through but he wanted her black panties for his collection. She didn't say anything to him when she returned to find her panties gone. Wearing only a sports bra, she casually walked without shame over to his kitchen where she grabbed a dish towel off the stove. She used it to make sure both of her holes were as dry as can be.

Once done she casually discarded it on his counter and walked over to get dressed. He was mesmerized by her confidence. "You're welcome to visit any time you like."

"When's the next test?"

"Probably not for another month."

"I might swing by then just to make sure I'm prepared."