Patreon LogoYour support makes Blue Moon possible (Patreon)

Blackmailing MILF (HotTexasCowboy & Cindi Fuller)

Joined
Feb 7, 2011
Bill knocked on his brother's bedroom door, peeking in with a sly smile on his face. The handsome, athletic seventeen-year-old heard a slightly distracted "Yeah, come in," and stepped into the room. His brother Fin was surfing the internet, having just minimized the screen with nude shots of hot, older women. Finley, known as Fin, was sixteen, a bit more than a year and a half younger than Bill, but with similar handsome features and well-toned lean body. He knew their mother was at her weekly book club meeting, and he didn't worry too much about Bill seeing him surfing porn. "So, what's up?" he asked with a cocked eyebrow.

"You have to come see this," Bill jerked his head for Fin to follow him. "Gonna knock you out," he promised.

The brothers were close, especially as their Dad had to travel so much for his business. Right now, Dad was gone for the next six weeks, somewhere in Asia, leaving the two teens with their mom for the first half of summer vacation. Fin followed Bill, raising both eyebrows as the older brother led them to their parents' bedroom door, and on through. Fin had always understood that this was off-limits to them.

"Wait 'till you see what I found!" Bill leered, leading them to sit on their parents' double bed.

"What were you looking for?" Fin asked, partly shocked but extremely curious.

"This!" Bill said triumphantly as he opened the drawer to the bedside table he knew was his mother's side. He reached in and held up a vibrator. "Last night I got up for a late night snack, and heard a buzzing from mom's room. When I listened at the door, I also heard moaning and something playing low on the tv. Can you imagine mom enjoying herself in here last night?"

Fin could. Their mom, even at twice their age, was the hottest babe in the school's parents group. Most of their friends called her a MILF, and the two teens had learned not to be embarrassed at that, recognizing the truth of the label. "But that's not all," Bill grinned sneakily, pulling out a DVD case with a disc within. There was no label on it. "I think this is what she was watching," he said, waggling his eyebrows. "Wait 'till you take a look!" He opened the player by the bed and put the disc in, taking the remote to turn on the wall tv.

The image came up, the video faded and rough, like it had been transferred from an old VCR tape. The first thing was a hand backing away from a camera. The hand slipped away to show a man in a tuxedo stepping back toward a woman in a white bridal gown leaning on the arm of a couch. "I shouldn't let you do this," the bride said, smiling naughtily, in a voice Fin found hauntingly familiar.

"Come on," the guy smiled. "I want something to remember you by. Don't you want a keepsake of your wedding day, too? Something you wouldn't want to share with Dan, of course," he said in a short laugh.

Dan was their father's name. And the woman on the tape was a younger version of their mother. And she was falling to her knees, her hands going to the strange man's zipper -- a man who was NOT their father. And she pulled out the man's penis and started licking it as it grew more erect, then slipping it into her mouth and moving back and forth.

The two brothers watched, their mouths slack in amazement as the woman they knew as Mom performed fellatio, then leaned back on the couch arm as the man raised her ruffled skirt and penetrated her, to her obvious enjoyment. "Jee-suz!" Fin said in awe. "Do you think Dad knows about this?"

"No fucking way," his brother said with certainty.

"Do you think he should?"

"Here's what I think," Bill said, his eyes intense. "I think we should make a copy, or a couple, and let Mom know what we know, and see if she thinks we should share this with Dad. And what she'll be willing to do to keep that from happening." He smiled sneakily.

"Wow!" Fin said in almost a whisper. "How far do you think she'd go?"

"As far as we want, Bro. She'd be ours for the next six weeks. What do you think of that?"

A slow, playful smile started to spread across Fin's face. He was no virgin, but there was a lot he wanted to learn. They got to work, and had the disc copied, one for each of them, plus copies on their computers. "Now how do we get this going?" Fin said, grinning in anticipation but a little uncertainly.

Bill paused, then went ahead. "I think if we both confront her, it might really spook her into something unexpected. I think we need to ease into this slowly, get her to make small concessions that gradually get her in deeper. I promise to let you know everything that happens so we can plan together, but let me start with her alone tonight. Then we'll figure out how to go from there. Don't worry, we'll make sure you get a fair share of fun, bro."

Fin reluctantly agreed that was probably better, and he headed back off to his room, leaving Bill alone in the living room, resting on the couch with the tv controller until their mom came home...
 
Sandy came home from work like any other day. She dropped her purse on the counter in the kitchen as her heels clicked across the tile floor. Her maroon blouse buttoned up the front did little to hide her 36dd breasts which threatened to burst her buttons it appeared. Her breasts were not that of a teenager. The were round and soft and hung lower than she would like. She was wearing a grey skirt that hugged her hips which were round and firm it was to her thighs a few inches above her knees and her dark thigh highs accented her curved well formed legs.

She was surprised to see her son sitting in the living room with the TV on. "Hey honey, what's going on" she said naively as she sat down on the sofa. His serious tone concerned her

Sandy had never been accused of being worldly. Vshe was often manipulated into doing things for others. She was caring and open and seemingly gullible which had gotten her into precarious situations before. One of those was about to come back to haunt her.
 
Sandy and Dan had been separated for several months. The boys visited their father on weekends, and were absorbing their dad's ever-less-hidden disrespect for his wife. Bill suspected a divorce was coming eventually, and the tape of his mother's wedding day infidelity would be a strong weapon for their father's side. He and Fin nevertheless didn't show the effect their father's disdain was having on their own view of their mom.

"Girls," Bill answered with a shrug to his mom's question. He looked at her with something approaching resignation. "I just don't get women, Mom. My last date with Jennifer was a bust. I don't get what they like and what they really want?" It was all a story; his last date had ended up with his hand down Jennifer's pants and her gasping in pleasure, but she wouldn't return the favor by rubbing his cock.

"They all pretend like they're so prim and proper, but I know they just want to enjoy themselves, the same as us guys," he went on in a show of frustration. "You like sex, don't you Mom?" he suddenly turned the question on her. "I mean, you're a pretty woman, and you don't mind showing that off to people. I know Dad's been gone a while, but I'll bet you really miss being alone with him, right? I'll bet thinking about it turns you on. Why pretend it doesn't?"

If she denied it, he had the video standing by to prove her wrong.
 
Sandy listened to her son, she had noticed her teen sons had been more distant and disrespectful lately, contributing it to teenage years. Her face blushed as her son began telling her about hi date and suddenly turned the tables on her.

"Well, I ..errr ... Y-yes I like sex. It's natural too" she stammered. Her son never asked her about things before and she wasn't about to tell him how horny she had been And how her vibrator wasn't the same. "Sure I miss your father sometimes. But we do ok without him don't we?"

She was afraid the answers might not be favorable. The boys may not want to be with her and might choose their father over her. She watched her son certain something was up. He never wanted to talk about this stuff. She just wasn't sure what it was.
 
Bill had to work hard to suppress his smirk. "Yeah, we do ok without Dad, I suppose," he seemed agree. "For sure, I know you do." At that, he raised the remote control he had been holding and pointed it at the tv/dvd and hit a button. The tv that had been muted flickered as the dvd started playing. There was the man not their father with their mother in her bridal dress, going to her knees and reaching for his zipper. "But then, I guess you always have," Bill added with a slight leer. "Shall I keep playing this, Mom? Or maybe I should send a copy to Dad. I doubt he's ever seen this, right?"

He paused the video and gave his mother a knowing look. Ready for her to admit he had her in the palm of his hand and see what she was willing to do about it.
 
Watching as her son turned on the recording. Her eyes wide. "Oh my god. Where did you get that?" Though she knew the answer. How could she have been so careless? She stared as he shut it off. Eyes wide as she watched her son's cocky smirk. No doubt he knew the consequences she faced if this got to their father.

"No.. Pleas, you can't show anyone, I should have destroyed it. You..we have to get rid of it" she pleaded seeing no mercy in her sons eyes. She felt a lump in her throat as she felt warm. Her eyes teary as she felt ashamed and trapped. Caught in her dirty secret.
 
Bill caught the glistening in her eyes and the quiver in her throat as she reacted in shock to the video. I've got her right where I want her, he thought. But rather than push hard, he quickly rose and went behind the couch, leaning down to massage his mother's shoulders. "Hey, relax Mom. This can be our secret, okay? Dad doesn't need to see this, and I won't tell Fin." Leaving open the idea that Fin might learn of it on his own, he thought with an inner smirk.

"This will just be our secret. I just need you... to be nice to me. There's things I'm curious about, you know? Things you can show me. Things I know," he motioned his head toward the tv screen, "you already know a lot about. I mean, this is just a mom helping her son understand girls better, right?"

His rubbing hands tugged at her blouse material, and the top button popped open, both from the pressure of his fingers and the already existing tightness of her bust against the material. From behind and above, Bill could peer down her cleavage, and he liked the view.
 
Sandy sat horrified. Her son knowing her dirty secret was bad enough but the idea of her husband and other son finding out could be devastating. She felt her shoulders rubbed as he moved behind her. She was understandably tense as he rubbed them. His fingers moving her blouse as he worked her shoulder muscles. She gasped as the first button popped revealing the curve of her DD-cup breasts top and cleavage. She swallowed hard. Could this really be what he was talking about? Could he really be wanting this?

"I. Of course I'll be nice to you. Please. No one must know" she said trying to sound sweet. She was in turmoil. How could she get out of this? She sighed in resignation as her son looked down on her "what do I have to do?" She reluctantly gave in. Truly hoping he didn't expect sex.
 
Surrender, Bill thought triumphantly. He continued rubbing, feeling a surge to his groin at his victory. "Oh Mom," he said, feigning a casual attitude far from what he felt, "I just want you to be a good parent and help me learn things that will help me. Help me with girls." His fingers pulled at the fabric of her blouse and popped open the next button. He thought he'd be seeing her bra by now, but realized as his fingers rubbed her shoulders that there was no strap there. His mother going braless? The idea excited him further.

He moved back to sit on the couch, next to Sandy, shifted so he was partly facing her. "I've never, you know, seen a girl's tit--uh, breasts, you know. Not a girl's, but a woman's. I mean, except for videos on the net." He gestured toward the tv, which also served as a reminder to the blackmail he held over her. Not that she had revealed much during the video. She had remained in her wedding dress while blowing the guy, and the then lifted her shimmering bridal dress to let him fuck her from behind.

"If you, I mean, just so I'll know, would you mind showing me yours? You know," he winked, "just our little secret."
 
Sighing as her son moved around. Her big beasts pushing at the blouse. She watched as he sat down realizing she was going to have to endure some humiliation for a while. She sighed. Telling herself this was about helping teach her son. Not sexual.

Her tan aureolas were always so sensitive and about the size of a quarter. She undid her top as her big breasts swung free. Her sleeves pulled down as her shoulders were nude, the blouse around her back. Her nipples grew hard and long. Sticking out like pencil erasers in size and shape. She shivered as the air hit them. She had always been so responsive there.
 
Bill watched, fascinated, as his mother opened the blouse and slowly pushed the flaps around back, exposing her bust to him. "Wow!" he breathed softly, and it was no act. He had seen more than a few tits of his high school dates, but this pair was much more full and heavy than the school girls he'd played with. Even as embarrassed as she seemed to be, he saw the way her aureolas mottled with little bumps and the nipples poked up hard.

"Gosh, Mom," he said again, "they're really beautiful. Could I just...?" His hands rose almost instinctively, going under the globes and hefting them experimentally, as if testing their weight. He couldn't help but move his thumbs up to stroke just under the sensitive aureolas and barely brush her nipples. "How does that feel, Mom?" he asked her, his eyes fixed to the tempting globes.
 
As he stared she couldn't help feeling a bit flattered as he looked her big breasts over. She was shocked, to shocked to speak as he touched them. She swallowed hard and gasped as the thumbs ran over her sensitive nipples and teased her aureolas. Her back arched involuntarily as her heart started pounding. She knew this was not going to end well as her conniving son found how sensitive her nipples were and how it made her aroused.

Squirming her breathing coming hard. Her face flushed she eventually managed to moan out "ok. Ok. That's enough " as her body trembled. She was biting her lip. Her long blonde hair falling around her shoulders. She was trembling and the fact she hadn't been with a man hadn't helped her situation.
 
Bill couldn't help but notice the strength of Sandy's response to his boob teasing. Man! he thought. She's practically blowing it just from this! I wonder if she's getting wet. Hell, I wonder if she could cum just from playing with her tits and nipples. When she called for a stop, he gave her nipples a quick, light pinch, then continued to massage her breasts.

"What's the matter, Mom?" he asked innocently. "Is this bothering you? It doesn't hurt, does it? I thought girls were supposed to like it when you played with their breasts. Am I doing it right? What should I be doing?" His thumbs flicked over her nipples again. "What does it feel like when your nipples stand up like that? Is that good, or bad?" He continued to play the part of the innocent, using it as an excuse to continue teasing her body.
 
Her hand went to her hair sliding her fingers through it as she squirmed. Feeling him pinch her nipples making them stand out more. She was arching her back more her protests ignored. "It..it feels good when they are hard. Your. Agh. Doing it right. It's enough. You know how now aahhhh" she gasped as he continued to play with her big breasts. Feeling her son turn her on despite her disgust and humiliation from it.

He seemed like a kid with a new toy as he played with her huge breasts. He could tell how sensitive her nipples were and was pretty gentle so far.
 
It was exciting to see how affected she was by this, Bill thought. His jeans were getting almost uncomfortably tight as he enjoyed manipulating her like this. "I need to get used to seeing these," he said, as if musing aloud. "I think you should wear more revealing tops from now on, around the house. Low cut, tight, find some really thin blouses. That's what I want to see. Okay?"

Suddenly he leaned down and opened his lips, lifting one of her breast to his mouth. He took the nipple in and fastened his lips to the tip of her breast, sucking in the nipple hard, closing on it. He widened his lips and used his tongue to flick rapidly over the nipple, loving the feel of the rocky bullet against his tongue. Then he release it, straightened back up, and let go of her breasts.

"That was really neat, Mom. I think I learned a lot. We'll have to do this again, soon. And don't forget about what I said about your tops from now on, right?" He glanced at the tv, reminding her of the video. "Why don't you go change into something?"
 
Sandy' back arched as she felt his mouth sucking her. Her nipple pulled in. Her body squirming as he made her nipple so hard. She was in turmoil as he teased her. Her body so aroused. She felt guilty. Guilty about the recording and even more so about letting her teen son do this to her.

"I'll try" she managed to moan out sounding more like a whine as he worked her body into a frenzy. She was gasping for air as he finished. Pulling away her wet cold nipple stood out proud and glistening with his Saliva.

His instructions were clear and to keep him quiet about the recording she decided revealing tops wasn't so bad. She nodded. Knees shaking as she went upstairs. Not sure what to put on.

She slipped out of her work clothes. Slipping into some jeans. She held the sheer blouse for a long time before sighing and putting it on. Her breasts jiggled and swayed with each step as her tan nipples were easily seen through the sheer white button front blouse.
 
While Sandy was changing, Bill dashed up to Fin's room to fill him in. He found his brother watching their mother's wedding porn video closely, sometimes freezing the frame to examine it closely. "She was floored when I showed her my copy of the video," Bill told him triumphantly. "She'll do anything to keep it from Dad. I got her to show me her tits and let me feel them! And from now on, she's wearing sexy tops to show them off for us. I'll keep teasing her tonight. Tomorrow is your day. When you come down for dinner, you can look at her shirt, but don't make a big thing of it. Take you phone and seem to be real absorbed in it." Fin agreed with the strategy.

Bill then dashed back downstairs to be there before Sandy returned. He was hanging up his phone when she reappeared, and he smiled approvingly at her choice of blouse. Her breasts jiggled within her thin shirt with each move she made, and her nipples continued to poke daringly out against the sheer fabric.

"I ordered a pizza for supper," he told her. "It should be here in a bit. Come here." He motioned for her to come to where he was standing. He blatantly stared at her blouse, and nodded. "Yeah, that looks great. Dress like that, okay?" He reached to pinch one nipple he could see through her shirt, a harder pinch than before, and held it several seconds to see her reaction.
 
Walking into the living room her son looking at her in a whole new way. She was walking in, her breasts jiggled and bounced with each step. She watched nervously as her son approached her. Her nipples poking out hard from the earlier play. She saw the grin on her son's face, knew he was up to something.

As he complemented her on her blouse, she felt his finger grab her nipple. Not asking permission this time, taking it for granted she was going to let him, and of course, she knew she had little choice. She felt his touch squeeze her nipple, the touch feeling good at first, her mouth opened in a gasp and her nipple swelled in his fingers. The pleasure turned to pain as he pinched harder, her face grimaced as she took the punishment. She winced as he finally let go of the abused nipple, it stood out red and stiff as he let it go grinning.

She nodded "ok" as he told her that's how she should dress. she felt humiliated but it was better than the alternative. The bell rang about the time he want back to sit down, she grabbed her billfold from her purse, knowing it was the Pizza. She didn't even think about her blouse till she opened the door, the young delivery drivers eyes widened as she realized what she had done.

She paid him, as she took the pizza, her face flushed in embarrassment as she brought the pizza back in. "BILL...FINNNN... PIZZAAA" she said as she placed it on the table. getting plates out for everyone as she sat down at the table and waited for them to come to supper.
 
Bill was in the living room, picturing in his mind the deliverer's reaction when Sandy opened the door with her tits there to poke his eyes out. And his mom's reaction to being seen like that. Yeah, this was going to be fun. Grinning, he walked to the base of the stairs and echoed mom's yell upstairs for Fin to join them. Then he sauntered into the dining room, smiling as he took a chair across from Sandy so he could keep looking at her boobs while they ate.

Fin joined them shortly. He had been on the internet, going to certain sites he knew to find specific programs he wanted. Fin was the computer nerd of the family, but lately some of his experiments had peaked into the hacker area. Nothing malicious, depending on your definitions, but now he had a specific goal in mind. He picked up his smart phone, remembering Bill's instruction, and started a game he appeared engrossed in as he came into the dining room. He glanced up as he sat down, and couldn't help but stare for several moments at his mother's revealing top. He blinked, and offered up a quiet, "Uh, wow, Mom. You look... nice." He would have kept staring, but Bill cleared his throat, and Fin grabbed a bite of pizza and returned to his phone game, sneaking peeks, however, whenever he paused to get another bite.

Dinner was a quiet affair. Fin had an earbud in one ear, but Bill wasn't in the mood much for conversation. The boys, typical teens, wolfed down much of the pizza, washing them down with soda. When they were done, neither moved while they expected their mom to take the dishes into the kitchen. As soon as she was through the door, however, Fin leaned across the table to his brother and whispered, "Keep her down here for, oh, about an hour. I need time to do something."

Bill cocked an eyebrow curiously, but nodded. "No problem," he whispered back, and Fin took off back upstairs. Bill waited for his mother's return, then stood up as she came in. "Hey, mom, I wanted to ask you a couple of things. Okay?" He didn't wait for permission. Instead he reached to one of her boobs and snapped his index finger over her still-pronounced nipple. "So, are these perked up all the time like this, or does it only happen sometimes. What does it mean when they do this?"
 
As they sat down sandy realized both boys watched her breasts jiggle. " well thank you fin" she said as he complimented her. He didn't really pay attention after that. Not like his brother who seemed totally engrossed in her big breasts. Men had always stared at them. They were large and round and natural. Her nipples pointed slightly upward and out and were long and easy to spot under her clothes even.

As the meal finished she put the dishes in the dishwasher. Every move made her breasts bounce and sway. As fin headed upstairs. Bill met her with more "questions" she was relieved He did seem just curious and experimental more than wanting incest. She grew a bit more trusting and open.

"Owe" she moaned as he flicked her nipple. " they are sensitive. Mine more than some women's. And they get hard because of cold or excitement or stimulation. " she explained. Rubbing her flicked nipple as it stood out harder now.

She could see his curious or was it mischievous mind working as he grinned. His mother standing revealed from the waist up in a sheer blouse that did little to hide her nipples. She felt less confident and more uncertain by the minute
 
"Ah," Bill said, nodding a bit, but acting as if still curious. "So... which is it? I mean, you're not cold, are you?" He watched as her own fingers circled the nipple he'd flicked. Without hesitation, he raised his hand and mimicked her fingers on her other nipple, feeling it hard through the sheer blouse. "Excitement or stimulation, you said. Aren't those really the same thing? If you're getting stimulated, doesn't that mean you're getting excited? You said your nipples were more sensitive than some womens'. Does that mean they get you more excited than other girls? Does stimulating them turn you on more? Are you saying other girls wouldn't react the same way?"
 
Her hand dropping as she stops rubbing her nipple as her son rubs the other one. Her face reddens as she flushes. " yes. I get really excited from it" she admits. Embarrassed to be having this conversation with her son. His fingers working her nipple as it stands out hard. The other one throbbing from him flicking it with his finger. She bites her lower lip as she knows she has to stand there and take it. "I think most girls would be excited. Not all at the same levels from this though" she continues. Her upper chest and face flushed with excitement and embarrassment.

His grin showing he enjoys playing with her full breasts. Her nipples so hard and long. Standing out like pencil erasers. She can't remember when they were so long. Or when a guy had played with them so much. Her knees felt week as she watched him. His curiosity about how different things affected her nipples made her nervous about what he would do to them next.
 
When Sandy's hand abandoned her nipple, Bill's other hand rose to take its place, his fingers massaging both breasts and the hard, erect nipples. She's like putty in my hands, he thought. "So, like, when you say that this makes a girl excited," he continued, as if seeking more hypothetical knowledge, "does that mean... just the nipples are excited? Or, does it affect the rest of you, like, you know, other parts? And, when girls get excited, how does that make them feel? Are they, like, stronger, or weaker, or all flush and needy?" God! He loved playing this game!
 
Sandy's legs were shaking as her nipples were teased. Her body was aroused. She was stammering "all parts g-get excited" she stammered her face flushed she leaned back against the counter. Her hands holding herself up. She saw the gleam in her sons eyes as he played with her large breasts. She could feel her heart pounding as her breathing came harder. Her nipples were tingling and hard. Her aureolas wrinkled as her nipples looked darker. " please no more" she said sounding weak as she let him play with her like a toy.
 
"Wow... All parts?" Bill repeated. She was begging him to stop, and he loved how hearing her beg made him feel. Powerful, and in control of her body. Even as she begged to stop, she couldn't move away from his touch. "So, are you, like getting wet, you know, down there?" he asked slyly.

And to check, one of his hands left her nipple and reached to cup the crotch of her jeans. His fingers pressed and rubbed at her pussy, and he could clearly feel dampness leaking into the fabric. "You are!" he said, as if amazed. His hand rubbed and his fingers wriggled, up and down and against her through the denim and underwear, if she was wearing any. "What would happen if I kept doing this to a girl?" he pretended to ask. I've got my mom by the pussy, and she can't get away, he told himself.

As if challenging his control, he said, his voice a bit husky, "If you want this to stop, you just need to move away..." If she could, he thought.
 
Back
Top Bottom