Pictures of Ms. Riley

Sweat rolled down Bobby's back as he put the lawn mower away, the summer sun baking him as he worked outdoors. On the deck behind him he could hear Ms. Riley on the phone, probably talking business. He stole a glance over his shoulder at her as he stepped out of the garage - tall, with lightly tanned skin and long black hair, she had been the object of his fantasies for years. His mother's best friend growing up, Alex Riley had never gotten married - preferring to spend her energy on her career, the way Bobby's mother always phrased it. She lived in a large house not far from Bobby and his mother, which made Bobby the perfect person to be forced into doing favors for her.

Like mowing her lawn.

Bobby shut the garage and walked towards the deck where Ms. Riley sat, wiping his face with his shirt. Soaked as it was, it didn't help, but Ms. Riley had a dry towel and a glass of iced tea waiting for him under the awning. He wiped his face, downed the entire glass of iced tea, and looked up just in time for her to finish her phone call.

"The lawn looks great," she said. She pulled her sunglasses down off her face and glanced up at Bobby. In his imaginings, this would be the part where she would reach up and touch his stomach, remark on how much he had grown up, and begin to strip off her shirt in the summer heat. They wouldn't even bother going inside, the heat of the moment and their attraction forcing them to fuck right there on the deck. Ms. Riley would moan Bobby's name as he came in her pussy and tell him that was the greatest sex she had ever had. She'd be so impressed, she'd demand he fuck again on the spot.

Of course, this wasn't a dream. Real life didn't work like that.

"You also look good," she continued, oblivious to the rapid fire thoughts playing through Bobby's head. "College seems to favor you."

"It's pretty fun, yeah," Bobby said, his voice squeaking a little. That line had been a touch close to what he had imagined. He tried to banish the thought from his head. Ms. Riley, however, being outside, had chosen to wear a low cut blouse, and he could see a bead of sweat roll down her chest and into her cleavage.

"And you're studying and being good so that you get a good job when you graduate?" She asked.

"Of course," Bobby lied. He had skipped class more often than he went to class, but he hadn't failed anything.

"Then you're wasting your time," Ms. Riley said. She put her sunglasses back on and slouched back down on her chair. "College is a time to learn who you are as a person. Live a little."

"I live. But my mom says I need to get good grades."

"Your mom never got better than a C through college and most of that was through my help."

"So you were good and studying?" Bobby asked. He lowered himself down into a chair and poured himself another glass of iced tea.

"Of course not," Ms. Riley said. "I'm just smart." She smirked at Bobby. "That let me get away with all the extracurricular activities."

Bobby took a sip of iced tea to buy himself some time to think. He wanted to know more - surely Ms. Riley was alluding to something raunchy, no? He felt his dick start to stiffen, but he had to know more.

"What kind of extracurricular activities are we talking about, exactly?" He asked, trying not to sound too eager. He was pretty sure he failed, but Ms. Riley chuckled anyway.

"The stories of the things your mother and I got up to in college would make you blush, mister," she said. She pulled a fifty out from the bag at her side and handed it to Bobby. "Now go and leave me sit here and enjoy my freshly mowed lawn in peace."

Bobby got home later that evening and jerked off immediately, thinking of Ms. Riley in college and the things she might have gotten up to. He imagined her on her knees, his dick in her mouth, party music blasting in the background, her clear blue eyes gazing up at him and she stroked him and moaned. He came hard into the towel he held, panting slightly, the image still in his brain. He wiped himself off, stuffed the towel in the bottom of his hamper, and went downstairs.

He was idly watching tv when his mother came home from work. She had recently finalized a deal for a house for a couple only slightly older than Bobby, which was weird to think about, but the sale was huge. She had been working overtime to get all the paperwork in order, so she was basically always exhausted. It was only her and Bobby in the house - Bobby's father had left ages ago and no one had heard from him in years. But it meant there was no one else to help his mom take care of the house when Bobby wasn't around.

He hopped up and followed his mother - roughly 5'6", with medium length blonde hair, she had put on some weight in the years since she had Bobby, but he didn't consider her fat. She had a healthy look about her, and more than one of Bobby's friends had told him they found her hot. Bobby tried not to think about his mom that way. But Ms. Riley's voice floated into the back of his head "what your mother and I did in college would make you blush", and he found it hard not to admire his mother's ass as he walked behind her.

"How was work?" He asked as a way to distract himself. He was starting to get hard again, though he attributed that more to Ms. Riley than to his mother. He completely missed what his mother was saying, but the exact wording wasn't really important. She never expected him to remember the details anyway, so he hmmed and nodded as was appropriate while helping her prepare dinner. Having had a long day, she let him do most of the work, but he didn't mind. He told her of his day with Ms. Riley, and, on impulse, mentioned what Ms. Riley had said about his mother's habits in college.

"Yeah, I was a bit of a deviant back then," she said, chuckling. "Did Alex tell you any stories in particular?"

"She just said they would make me blush," Bobby said. "Any I should know about?"

His mother laughed again and shook her head. "I am not going to be the one to spill any secrets. If she didn't want to say, then I'm not going to tell you."

And no matter what Bobby did, he couldn't convince her to tell him. They finished cooking, ate, and watched some tv before bed. Bobby wished his mother a good night, then spent some more time fantasizing about Ms. Riley and wondering how he was going to get her to tell him some stories.

A few weeks later, Bobby had been roped into helping Ms. Riley again. This time, she needed him to find something in her attic, a box of papers she needed for work. She had kept the attic as a place to store papers and other business things but had slowly allowed them all to be buried by other useless things she had shoved up there, meaning to get around to cleaning later.

Well, Bobby didn't mind. He dug through the mess in the attic while Ms. Riley stood below, telling him what he could and couldn't throw out. She had decided to make it a full blown summer cleaning, since he was going to have to go through most of the attic to get to the papers anyway. It wasn't difficult work, but the attic was hot, and he quickly worked up a sweat.

Deciding it was too hot, he took his shirt off. Not wanting to lose it up there, he dropped it down to Ms. Riley, who caught it looking confused. It took her a second to realize what she was holding.

"There a stripper pole up there I am unaware of?" She asked, holding the shirt up in front of her.

"Only one way to find out," Bobby called down. He held his breath after saying it, worried she would take offense to the innuendo.

"If you are implying that the only way to find out is if I go up there myself you are, first, reading from the oldest playbook out there, and second making me doubt offering to pay you to have you find something for me, as one would assume you were observant enough to discover a stripper pole of your own volition."

"Well," Bobby said, lifting a box to see what was underneath it, "if there is a stripper pole and I just took my shirt off, imagine what my mother would say when she finds out you paid me to strip for her."

Ms. Riley laughed. "Now that would certainly remind her of our college days." Bobby put the box down, searching for another come back. Ms. Riley's phone, however, rang and she walked away to answer it before he could think of something clever enough to say.

He went back to working, pulling open boxes and sorting though them, trying to decide for himself what to keep or toss. He was half an hour working by himself when he came across a box of old pictures. It was old, and worn, covered in a layer of dust. Smaller than a shoebox, it looked as if it had seen better days, as if it had been stuffed away hastily and then forgotten. Inside were a handful of photographs, the kind that came printed out of a Polaroid of old. Each of the photos featured a young woman, hair black as coal, in various naked positions. Some of them were of just her, posed on a couch, or a chair, or a rug. In one she played with her pussy. In another, her tits. But the others were of her and a partner. Sometimes the partner was a girl - often a red head, once a brunette, and once both of them at the same time - but most of them were of her and a guy. Here a picture with a dick in her mouth, there a dick in her pussy, the next a dick in her ass. A close up of her face covered in cum with her eyes closed, a second girl licking the cum off.

"How's it going up there?" Ms. Riley called up the steps. Bobby nearly yelped, but controlled himself. He coughed, cleared his throat.

"It's going alright," he said. He coughed again. "Kind of dusty."

"You want some water or something?" She asked. Bobby called down yes and she went off to get him a glass. He looked down at the box in his hands. He wanted to take all of them, but he wasn't sure how to get away with them. Coming down with the box would be conspicuous and she would recognize the box with her nudes in it, surely. He grabbed a bunch and shoved them into the pocket of his pants, then stuffed the box where he would be able to find it again.

He eventually found the box of papers she was looking for and carried it down to Ms. Riley. He was extremely conscious of the pictures in his pocket, hoping they wouldn't fall out and wondering how he would explain them to Ms. Riley. She gave him some cookies and another fifty when he brought the box down and he discovered she had washed his shirt for him, which was nice. He pulled it over his head and she gave him a kiss on the cheek on his way out the door.

She never discovered the pictures.

At home, he pulled out the pictures he had stolen and laid them out on his bed. He hadn't really given much thought to the ones he had taken, so there was a hodge podge of them, but thankfully none of them showed any dude's faces. It would be much more fun for Bobby that way. He pulled out his rapidly hardening dick as he looked them over, marveling in how perfect her pussy looked, how tight and perky her breasts her. She hair was black and shiny, falling all the way to her ass crack. He stroked his dick to it, looking at the picture of her with a dick in her ass, imagining it was his dick in the picture. He came before he was really ready and the cum splattered a picture of her face. He cursed at first, worried that he had ruined the picture. But as he grabbed it and looked at it he realized how hot it was. It was like cumming on her face. His dick stiffened and he came again, this time aiming for the picture of her face.

It became a daily occurrence for him, jerking off to Ms. Riley's pictures. He took them with him when he left for college that fall, thankful that he had his own room at the dorms. He dated some bit, always looking for someone who could turn him on the way Ms. Riley did, but to no avail. He saw her when he went home for Thanksgiving, but she seemed none the wiser for the missing pictures.

He moved out of the dorms for the winter in the middle of a snow storm. His mom came to help him move, but the slippery ground and the weight of some of the boxes caused him to slip and fall. He dropped a few boxes right into a puddle, and the cardboard soaked through immediately. Cursing, he grabbed what he could, struggling to keep the boxes together as best he could. His buddy from school helped him get them in the car, but the boxes were ruined.

And the pictures were in one of them.

He spent the car ride home trying to avoid a Panic attack. If the box ripped apart and spilled everything, the pictures would end up all over the ground. And if his mom were the one to be carrying the box, she would most definitely see. Would she recognize them? Would she recognize the photos of her best friend from college? Chances were pretty high that she had taken at least a few of them (a question that always bothered Bobby, but that he usually ended up pushing out of his head). How would she react?

So when they pulled into the driveway, Bobby hopped out quickly and grabbed the box they were stored in, carefully trying to keep the box from falling apart. His mother moved to help him, but he brushed her off (probably brusquely). He managed to get it into his room without losing anything.

"I hope nothing in there got ruined, Bobby," his mother said as she carried a second box into his room. "But we'll replace anything we can." Bobby looked down at the box, cursed in his head. The pictures didn't get wet. They couldn't have.

They unloaded the rest of the car and Bobby went upstairs to "rest". He closed the door and locked it.

The box was falling apart even as it sat in the corner, the cardboard seeming to melt and collapse. He pulled open the top and it came off in one, damp piece. The bottom of the box was worse than the top. He crossed his fingers as he dug through the box, eventually finding where he had stuffed the pictures down near the bottom.

They were soaked. He laid them out on the floor, waved them around to try to dry them. He even borrowed his mother's hair dryer to blow dry them, but it didn't matter. They were ruined.

He gathered them up and put them in his desk drawer, laid out flat in the hopes they would dry back to normal, then flopped down onto his bed. He felt into his pants for his dick, but having had the actual visuals of Ms. Riley to look at for so many months seemed to have robbed him of his ability to fantasize. He wanted nothing more than to jerk off, but he couldn't get himself to finish. He needed the pictures. He pulled one out of his desk drawer, but the image was completely ruined and didn't help.

He sat in his desk chair, thinking. There were more pictures. If he could get himself up to Ms. Riley's attic, he could get more pictures. He had to.

He spent the next morning unpacking what he needed to unpack, then got to work helping his mom decorate for Christmas. They spent the next week getting into the spirit for Christmas, buying presents and a tree and going caroling. One morning, Ms. Riley called to invite them over for drinks on Christmas Eve, as she did every year.

"Alex wants to know if you'll be joining us this year or if you'll be off on your own getting into trouble," his mother asked. Usually Bobby turned them down - it was just the two of them drinking and talking and it wasn't usually very fun.

"Sure why not?" Bobby said. His mother looked surprised. "I haven't seen her in a while and I go get into enough trouble at school, anyway."

His mother related this to Ms. Riley, then laughed.

"She says she'll have to break out the hard stuff for you."

"Perfect."

On Christmas Eve they sat around watching Christmas movies and drinking. True to her word, Ms. Riley broke out some whiskey and knocked some back with Bobby. His mother stuck with wine, but by the end of the night it didn't matter. They were each quite drunk. Bobby excused himself to go to the bathroom and stood up to do just that when Ms. Riley stood up abruptly.

"I just remembered," she said, slapping herself on the forehead. "I saw the stupidest thing on the way home from the liquor store. Did you happen to drive down third?"

"We walked," Bobby's mother said gesturing with her drink.

"Well do you want to go walk and look at this house?" Ms. Riley said. "It's atrocious." Bobby's mother laughed and agreed and they looked at him. He almost said yes.

"I think it's probably best for me to stay inside," Bobby said. "Drunk Bobby doesn't like being outside."

Ms. Riley shrugged. "Suit yourself. Just don't drink all my whiskey." They put their jackets on and went outside.

Bobby hurried to the bathroom and peed, then hustled over to the ladder up to the attic. It took a few tries, but he finally managed to pull it down. He was thankful they weren't here as he would never have been able to do this quietly, not with how drunk he was. He struggled up the ladder, almost fell, but made it to the attic. He grabbed the box and pulled a few pictures out of it but, being drunk, he dropped it. Pictures scattered across the floor. Cursing, he grabbed them up and hastily shoved them back into the box. Some of them fell out of the attic, but he figured he would get them when he went down. He checked and double checked the floor of the attic to make sure he got all the pictures, then tucked the box away and went back down the ladder. He picked up the pictures he saw in the hallway, put the ladder to the attic back and brushed the dust off his pants. The thought of the pictures in his pocket made him hard, so he beat himself off into Ms. Riley's bathroom sink real quick and cleaned up. He was sitting back in the living room before they got back, working on a glass of whiskey.

They drank for a little while longer, wished each other a merry Christmas at midnight. Ms. Riley gave him a big kiss on the cheek and told him he should really have a girlfriend to give him a real kiss. She winked and offered to give him a real kiss anyway, but Bobby's mother swatted her arm and pulled Bobby into a hug. She kissed him on the other cheek, remarking that he didn't need some old spinster anyway. They all laughed, then went home. He jerked off again when he got home, cumming all over a picture of Ms. Riley's pussy.

Christmas came and went, a small affair. Two days after, Ms. Riley called, asking for Bobby's help with something. So he bundled up and walked over, hands in his pockets, head tucked against the wind.

When he arrived, Ms. Riley had a mug of hot chocolate freshly made for him and was sitting waiting at the table. He hung his coat up then sat and joined her. The hot chocolate smelled delicious, and even though she wore a black turtleneck that showed no skin, the way it clung to her body made Bobby's dick twitch. Black hair draped over one shoulder, blue eyes popping against the white face, Bobby wanted nothing more than to cum all over her. He pushed the thoughts into the back of his mind.

"Hi Bobby," she said. She fidgeted.

"Hi, Ms. Riley," Bobby said. He took a sip of the hot chocolate to keep from fidgeting. She looked down at her fingers, up at him, smiled slightly and then looked back down. He set his mug on the table but kept his hands on it, letting the mug warm them.

"So what is it you need me to do today?" Bobby asked, trying to ignore whatever it was that was going on with her. She smiled, then pulled something out of her lap and placed it on the table between them: one of the polaroids from the attic.

Bobby stared at it, at a loss for words. It was a picture of Ms. Riley laying out on a couch, taken from between her legs while some dick face fucked her. His dick stiffened, but he couldn't think of anything to say.

"I found that on Christmas morning," Ms. Riley said. "In the closet near the attic. I was very confused because I couldn't think of where it had come from and spent the last few days thinking of where I may have seen this, because it looked familiar. That's when I remembered. And I went up into the attic and found the box of these, tucked in somewhere that made it rather hard for me to find them."