tagMatureMrs. Maitland's SAD Valentine

Mrs. Maitland's SAD Valentine


Sincere thanks to MSTarot, Privates1stclass, and SecondCircle for mentoring me and making this a better story. I appreciate every minute of your time.

This is my Valentine's Day 2014 contest entry. Vote, if you like. Thanks for reading.

Part 1: The New Job

"Saturday will be sunny and unseasonably warm for the end of September," the perky blonde in front of the weather map said.

"Awesome!" Brad Spencer said back to her. "Playoffs are on Saturday."

Brad had gotten home from work and turned on the TV in the living room, just in time to catch the weather recap at the end of the eleven o'clock news on Channel 4.

He was still a little pissed that his new job would keep him from making it to softball practice on Thursday, but he was grateful just to have the job. It wasn't easy for a guy like him to find a good, steady job, especially with benefits.

He went to the kitchen to grab a beer and a bag of pretzels, and then plopped on the couch, spilling some of the beer on his pants. He pulled his phone out of his pocket and opened the porn site he kept bookmarked.

"The best part of living alone and working second shift. Porn in the living room, and I don't have to get up in the morning," he said out loud. "If I could figure out how to get this on the big screen, life would be perfect."

He scrolled through the new videos until he found a girl-on-girl scene that made his cock stir. He liked lesbian porn, especially when they really looked like they were into each other. He ate his pretzels while he watched, quickly losing interest in the scene.

"Fuckin' porn stars. Shouldn't they be able to pretend they like each other?" he muttered as he watched their tongues practically sword fighting in what was supposed to be a kiss.

He selected and rejected another and another until he finally settled on a sweet massage scene in which a barely-legal blonde in pigtails lay on her stomach on the table, naked and blindfolded. The hot MILF that was massaging her back stood near Blondie's head, still fully clothed. She slid her oiled hands down to Blondie's ass and slowly rubbed the muscles beneath her skin When her hands reversed to slide back up her spine, the masseuse slipped her finger between Blondie's ass cheeks, making her shudder as her finger grazed her anus.

"I like where this one is going," Brad said to the empty room. He put his pretzels aside, and drained the rest of the beer can in one gulp. He paused the video and walked to the small bathroom to take a piss before he got too hard to pee. He didn't bother to wash his hands afterward, and he walked back to the couch with his cock in his hand.

He started the video again, and began to stroke.

In the video the masseuse leaned down to Blondie's ear and whispered, just loudly enough to hear, "Michelle, you can turn over now."

The camera cut to Michelle, still blindfolded and lying on her back with pools of massage oil trickling down her body. Brad's erection jumped to full hardness as soon as he saw her tits. They were on the smallish side, but her pink nipples jutted out like erasers on those giant pencils they sold in souvenir shops. The camera slowly moved lower and zoomed in on her completely bald pussy. Her soft, pink lips peeked out from between her slightly parted legs, a sight that caused Brad to moan while he tightened his fist around his cock.

In the next shot the camera man was standing behind Blondie's head. While she lay there on display, the masseuse stepped into the shot at the foot of the table, now completely naked and glistening with oil as well. He moaned out loud, imagining that the oil smelled like exotic spices.

Brad paused the video for a moment to examine the masseuse's body, comparing it to her "client's." As enticing as Blondie's tight, little body was, the masseuse's exuded womanhood. Her tits were heavy and full without sagging. Her stomach was slim, but not skinny like Blondie's. Her curvaceous hips and rounded bottom filled out her hourglass figure. The difference was striking. Although Blondie had to be of legal age to appear in the video, she looked like a child next to the sensuous woman that was massaging her.

She placed her oiled palms on Blondie's thighs and began rubbing her hands up and down the length of her legs. As she bent to reach higher on her body, her breasts grazed the tops of Blondie's feet, making both women shudder.

Brad looked at the time left on the video— eight minutes, twelve seconds. "Yep," he thought. "I'll be done by then."

Leaving her hands on Blondie's stomach, she moved around the table to stand near her head. Brad began to stroke faster as she brought her oiled hands up over Blondie's tits. When they trailed over her nipples, she whispered again, "Oh, Michelle. You're so ready for me, aren't you?"

Michelle's only response was a small whimper. Brad pinched right under the spongy head of his cock, sending a jolt down through his balls. The masseuse bent a little bit, allowing her nipple to brush Blondie's lips. She stuck her tongue out, and found the nipple in front of her. She tried to suck it into her mouth, but the masseuse stepped away and helped Michelle move herself closer to the foot of the table.

She slid her hands up her thighs, sliding them inward as they got closer to her body. When she reached her pussy, she dipped her first two fingers into the cleft between her legs, moistening her fingertips. She used the fingertips of her other hand to spread Michelle's lips. When the camera zoomed in for a close shot, Brad could see a droplet of her wetness threatening to drip to the massage table.

Brad stroked faster, imagining himself standing at the end of the table, getting ready to plunge his cock into her tight pussy while the masseuse lowered her pussy over Blondie's face. A loud moan from the blonde brought him back to the video, and he watched the MILF place her tongue between Michelle's swollen pussy lips and begin licking her clit.

He closed his eyes, feeling his balls start to tighten. He was breathing fast and hard. His hand pounded up and down on his cock, making a rhythmic slapping noise. Slippery pre-cum spilled out of the head, and dripped onto his hand. The lubrication reminded him of the massage oil, and he opened his eyes to watch the video once again.

The masseuse's mouth was planted deeply into her pussy. Her head made slight movements up and down as she licked Blondie's clit. Her first two fingers pistoned in and out of her pussy.

Blondie's hands slid over her own tits, and she began pinching her nipples with her thumbs and forefingers. Brad could see the flush spreading across her chest, and he knew that she would come soon. When her hips began to buck against the masseuse's mouth, Brad's hips began bucking with hers. As hard as he tried, he couldn't hold out until Blondie came on the screen. His body went rigid, his eyes closed, and he began to spurt all over his hand and his pants.

As he relaxed, he heard Blondie cry out as she came for her masseuse. Brad opened his eyes in time to catch the black screen with the web address where the full video could be found. He clicked to find the name of the actresses, and took a screenshot for future reference.

Brad cleaned himself off with the tissues he kept on the end table, just for that purpose. He went to the kitchen to recycle his beer can and throw away the trash. He grabbed another beer from the fridge, sat down on the couch, and clicked into Facebook to see what his friends were up to.


As he pulled the industrial garbage can behind him to the science wing, Brad saw the huge banner at the end of the hall advertising the Homecoming events for the next week.

"Ugh," he said. Homecoming wasn't for guys like him, and he had always resented the way the school shoved it in his face. His grades were never good enough to last long on any school sports team, so even though he was pretty athletic, he was never one of the jocks.

He remembered the pep rallies, especially the ones for Homecoming. Sitting in the bleachers with the other guys with long hair and Metallica t-shirts, he had resented being forced to watch the Parade of the Popular around the gym. The worst was the introduction of the Homecoming Court. They wouldn't be crowned until the dance after the big game, but it was at the pep rally that the student body would pay homage to their elite.

The tradition at East Lake was to have the girls dress in the boys' football uniforms and the boys to dress in old prom dresses and plastic tiaras. They'd be introduced by the cheerleading captain who would read a nauseating description of all the fabulous things each court member had been doing for the last three years. Each couple would take a victory lap around the gym, waving and allowing everyone the opportunity to be jealous.

Definitely not for a guy like Brad.

He shrugged off his disgust and continued to the biology classrooms, the highlight of his night. Sure, these classrooms were messier than some of the others, but the animals in the cages lining the walls of the rooms provided a little bit of entertainment in his otherwise dull evening.

His favorite was the bearded dragon in Mrs. Maitland's room. According to the tag on his cage, his name was Marvin, and he was a friendly little fucker, as far as Brad could tell. As Brad walked up and down the rows of desks to sweep the floor, Marvin would run back and forth in his cage, like he was trying to follow him. Brad found himself working faster in Maitland's classroom than the other rooms, just to allow himself a couple of minutes to "chat" with the crazy lizard.

"You wanna come out and play, dontcha?" he said in a sing-song voice. "Marvin likes people, doesn't he?"

Brad looked at the lock on the cage, and wished for the hundredth time that his master key would open it. "One of these days I gotta get down here when Mrs. Maitland is still here. Maybe she'd let me hold you, Marvin," he said to the lizard. "Do ya think she would?"

Brad had graduated from East Lake High three years before, but Mrs. Maitland was new. New to East Lake anyway. He had only met Mrs. Maitland once, during the first week of school. He hadn't paid too much attention to her, except to wonder why someone her age was starting at a new school. He wasn't even sure what "her age" was, but the lines that crinkled around her blue eyes when she smiled and her salt-and-pepper hair told him that her years in high school were far behind her.

He remembered the teacher that she had replaced though. Brad had been in Mr. Morgan's class for biology two years in a row. He still suspected that he only passed the second time because Morgan couldn't stand to have him in class again.

"What a prick," Brad muttered under his breath as he picked up the garbage can and got back to work.


Brad arrived at the bowling alley just after seven o'clock. He looked around for his buddy Kris, who was already set up and ready to go. He had placed a pitcher of Miller Lite on the counter behind them, and was pouring it into clear plastic cups when Brad arrived.

"Hey, man. What's goin' on?" Brad asked.

"Hey, Brad. Not too much. Did you see the girls on your way in?"

"No. I thought they'd be here later," Brad said.

"Yeah. Me too, but Jenny got off work early. She brought Tanya with her. They just ran to the ladies' room. You'll like her," he said. He lowered his voice, and put the back of his hand alongside his mouth. "Huge tits, and she'll be offering to blow ya after two beers. "

"Nice," Brad said. He hadn't been with a girl for a long time. He had gone to school with plenty of girls that were known for using their oral abilities to boost their popularity, but he didn't have much to offer girls like that. He wondered what this girl's motivation might be.

But he wasn't going to ask.

As he tied his bowling shoes, Brad realized that he hadn't bowled in weeks. Working in the evenings kept him from joining the Thursday night league. He hadn't thought about how much he missed it until that moment.

"Fuckin' job," he thought to himself.

He turned to see the girls approaching. He hadn't met Tanya before, and she was a pleasant surprise. Short, spiky, dark hair, pretty face, nice, tight body with the huge tits that Kris had promised. Definitely a pleasant surprise.

He didn't realize that he was staring until she spoke.

"Brad? Hello?"

"Oh, uh, hi," he stammered, blushing.

Fortunately, Kris saved him by putting a beer in each of their hands, and announcing that Tanya would bowl first.

Tanya stepped up to grab a bright orange ball, almost slipping in the rented bowling shoes.

"I totally suck at this," she called over her shoulder. "Just warnin' ya."

"I totally don't care," Brad said to Kris with his eyes on her ass as she bent and launched the ball. She remained frozen in that position, watching the ball as rolled toward the gutter.

"Good one," he called to her.

"Good view, anyway," he said under his breath.

Brad stepped up behind her for her second ball, and offered his assistance. He put his hands on her hips and offered some pointers. He held her arm and demonstrated how she should roll the ball, allowing his hand to graze her ass while he made his point.

When he leaned forward, closer to her body, he could smell the heady scent of lavender in her hair. He resisted the urge to scoop her body into his before she launched her second ball.

This time she hit two pins, which caused her to jump up and down with her arms raised in victory on her way back to her seat.

As Brad watched her breasts bouncing in celebration, he thought, "My god. I love bowling."

After the eighth frame and the second pitcher, Tanya announced that she was going out to smoke. "You coming with?" she asked Brad.

They grabbed their jackets and headed out into the chilly night. Tanya lit her cigarette and offered it to Brad.

"No, thanks. I don't smoke."

"Yeah. I keep saying I'm going to quit, but I never do," she said.

"C'mon," Brad said. "Let's walk a little."

He took her hand and led her around the side of the building. There was an Applebee's restaurant facing that side, and they continued to walk to the back side of the building where it was darker. Tanya finished her cigarette and crushed it under her left Ugg.

"So, what are we doing back here, Brad?" Tanya asked. "I don't think we're supposed to be here."

"Well, I've had a couple of beers, so I needed some air."

He looked down at her, trying to catch a glimpse down her top, but she held her leather jacket tightly around her.

"Are you checking me out, Brad?" she asked with a smile.

"May-be," he said.

He stepped closer to her, backing her into the cold brick. Placing his palm against the wall, he leaned in to kiss her. She tipped her head back to meet his kiss. She opened her mouth to accept his tongue and reached her arms up around his neck. She arched her back, pressing her breasts into his body.

He brought his hand to the side of her face, and then allowed it to slide down to cup her breast. His tongue probed her mouth. He knew that she could feel his erection pressing into her stomach. He wondered if what Kris had said about the blow jobs was true.

As the kiss deepened, her hand slid from his hip to his fly, feeling the bulge forming there. "Does this guy need some air too?" she asked.

Brad chuckled at her corny question. "Yep. That's why we're back here. I didn't want the families coming out of Applebee's seeing you touching me there."

She giggled and fumbled with his belt.

"Whatcha doin'?" he asked with a grin.

"Nuthin'," she answered with an even bigger smile as she pulled down his zipper.

"Need some help?" He unfastened the button on his jeans and reached out to stroke her cheek.

She reached into his boxers and pulled out his cock, hard and ready. Brad knew it was just your everyday, average, white-boy dick, but Tanya put on a good show of telling him how long and thick it looked. He had enough beer in him to let her words stroke his ego.

A chilly, late-October breeze swept the dried leaves over the pavement in the parking lot. Brad's cock was dripping pre-cum, and when cool air met wet skin, it made him shiver.

"It's a little cold out here," he said. "I bet it's nice and warm in your mouth."

Instead of answering, Tanya crouched down in front of him and took his cock all the way into her mouth. She looked up at him and raised her eyebrows, as if to ask, "Better?"

"Oh, yeah. Nice and warm," he groaned.

Tanya began to lick his cock from the base all the way to the tip, stopping to collect his warm pre-cum with the tip of her tongue. As she licked his slit, he moaned again.

When she pulled her head back, she exposed his completely wet cock to the cold air, causing another shiver as she continued to lick the underside of his shaft. He placed his hands in her hair and pulled her head back into his pelvis. She pulled back, he pulled her forward. Over and over he felt the cold air attacking the warm saliva on his cock, and more warm saliva fighting back.

"Oh my god, baby. You're gonna make me come."

She put her hand into his boxers, and put her hand around his balls. She caressed the skin of his scrotum with her thumb and tugged gently on his pubic hair.

"You're driving me wild, baby. Pull my hair again," he said. "Not too hard. Oh, yeah. Suck my cock."

He could feel the pressure building around the base of his cock, and he knew he wouldn't be able to hold on for long. He stroked her hair as she pushed and pulled her mouth along his cock.

She looked up at him and smiled around his cock as he made eye contact with her. That smile pushed him right to the edge.

"Oh, baby. It's been so long. I'm gonna come in your mouth. Oh my god," he moaned.

His balls contracted, and his cock began to spasm against her tongue. She opened her mouth and stuck out her tongue to catch his cum. He took his hand and pushed the tip of his cock against the middle of her tongue. He liked the roughness of her taste buds on the tip of his cock and then the slipperiness of his cum.

When he finished spurting his cum in her mouth, she looked him in the eye and swallowed. She tucked his cock back into his pants as she rose to her feet. She wrapped her arms around his neck and kissed him deeply.

He kissed her back, zipped up, and took her by the hand, leading her back into the bowling alley.

When he got home later that evening, he thought about Tanya. She was cute and fun and a good cocksucker. "I should give her a call sometime," he thought to himself as he settled onto the couch with a beer and checked his Facebook.


The problem with working second shift was that Brad generally spent his day dreading going to work, which kept him from getting too much done around the house. He usually slept late since he stayed up half the night playing video games and watching porn. By the time he got up, it was lunchtime.

After a week of Indian summer the last week in October, the grass had gone through one, last growth spurt. He figured he'd better get out there and mow his lawn and his mother's lawn before George started to bitch. He hoped that this would be the last time he'd have to mow before winter even though it was nice just to be outside.

He put on his headphones and cranked up some Slipknot before starting the mower. Just as he made his first pass through the front yard, the sun broke through the clouds. He stopped walking for a moment, closed his eyes, and tipped his head back to let the sun shine on his face. He'd been feeling a little bit restless recently, but the sun felt warm and good, and it energized him.

He made quick work of his own lawn before zipping through his mother's small yard as well. He was almost disappointed when he was done, but it was getting late. He had to be at the school at quarter of three in order to start on time.

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