The Taming of a MILF Ch. 01

Sandra lay back on the couch, her legs spread wide, her dress unbuttoned so she could squeeze and play with her nipples as Tommy knelt between her legs and lapped up her juices with his mouth and tongue like the obedient boy toy she had turned him into. Tommy sucked on her clit, the way she liked it, as he slipped two fingers inside her cunt. Sandra squealed with delight as he eagerly worked her sex starved body.

Sandra was 45 year old trophy wife. Her husband had made his millions in the financial industry. As a result, she was pampered and had everything she could possibly want. Except for a husband who met her sexual needs. Over the years they had drifted apart. His position required that he travel extensively and for extended periods of time. When he was home he had no interest in his wife. Sam was getting all the action he could handle with the assistants he always made sure traveled with him. His assistants usually had two things in common. They were always twenty years younger than his wife, and they all had large breasts.

Sandra knew of his philandering ways, but couldn't understand them. She had always taken care of herself, working out regularly. She also sported a pair of 36DD breasts that were still nice and tight with little sag. And she hadn't even had any surgical help yet. She'd always tried to be attentive in bed to her husband's needs. But whatever she tried to do, it never seemed to be good enough for him. After twenty years of trying, she just gave up. She would have divorced him except for her fear of losing all the perks of being married to a wealthy business man.

Tommy was not very athletic, as teenage boys go. He was more of a bookworm who was more at home in the library than on the athletic field. He was a tall and gangly 18 year old, and extremely shy around girls. Sandra started her seduction of him slowly enough and innocently enough. She would have him come over to help out around the house; cutting the lawn in the spring and summer, raking leaves in the fall, cleaning out the driveway in the winter. As Tommy became more comfortable around Sandra, she in turn began dressing a little more provocatively. Dresses that were a little shorter. Tops that were low enough to reveal her ample cleavage. Then there were the physical gestures. Sandra would hug him more tightly with each encounter, making sure her breasts were mashed against his body. She would touch some part of his body as often as she could, always lingering a little longer each time.

Sandra decided it was time to spring the trap and sink her claws into his tender flesh. Tommy had just graduated and she wanted to give him a gift. She had been talking to him for several weeks about what he would like f. Tommy usually mentioned a video game or a book of some kind. But Sandra knew all along what she had in mind. Tommy walked through the front door of Sandra's house as she held it open for him. He immediately noticed her blouse unbuttoned down below her breasts. He'd always found her breasts magnets for his eyes. No matter where he was or what he was doing his eyes always drifted to those luscious mammaries of hers. And Sandra knew it.

"Come in Tommy!" She said with an overly cheerful voice. As Tommy stood in front of her. Sandra closed the door and then gave him a big hug, squeezing him extra hard. "And congratualtions! I know how hard you worked with your studies!" Sandra held on tight and wouldn't let go. Tommy finally returned the hug, wrapping his arms around her. Their bodies seemed to melt together. The longer Sandra held him, the stiffer his cock became. Tommy knew it was just a matter of seconds before his cock was poking into Sandra's stomach.

Sandra released him. "Why don't you go sit on the couch and I'll get us some lemonade." Tommy walked into the living room and sat down, trying to adjust his swollen cock as he sat. Five minutes later Sandra came bouncing in carrying two glasses of lemonade. She sat down next to him, her tits almost completely hanging out. Tommy got an eyeful to Sandra's delight. He tried to take a drink of his lemonade, but his hand was shaking too much.

Sandra thought she'd play the innocent card. "Tommy! Are you staring at my chest?"

Tommy turned red with humiliation as he tried to stammer out an apology. "No, no Miss Jones! I'm sorry! I was just . . . ."

Sandra couldn't help but laugh at the poor boys defense of his staring at her chest. Her taunting him was bordering on cruelty. "Why you naughty boy! I suppose you want to see them don't you? Come on now, tell me the truth! You want to see them!"

"No ma'am! I mean no . . ."

Sandra reached for his hand and guided it to the inside of her blouse. Tommy's palm covered her hardening nipple. Neither of them said anything as Tommy's hand closed around her enormous jug and began to squeeze it. "Mmmmmm! That feels good!" Sandra moaned seductively.

Tommy almost shot a load in his pants at that point. The closest he'd ever come to a real tit was porn on the internet. Now one of the hottest MILF's in the neighborhood was letting him feel hers.

Sandra looked at him. "You have to promise me you won't tell anyone about this Tommy. I don't want either of us to get in trouble."

Tommy looked up briefly, not wanting to take his eyes off the most beautiful thing he'd ever seen or felt. He was afraid if he stopped looking at it, it would disappear, like it had been a dream. "I promise!" he said sheepishly.

Sandra smiled a devilish grin. "Well then why don't I just give you your graduation gift now." She unbuttoned the rest of her blouse, opened it, and let it fall off her shoulders. She sat next to Tommy topless.

Tommy sat and stared in awe at the most beautiful pair of breasts he'd ever seen. He then reached up with both hands and began fondling them with no further encouragement from Sandra. He had the awkward touch of a boy unsure of how to handle a woman's tits.

Sandra lay back as Tommy explored her sensitive mammaries. Her enjoyment and pleasure coming more from knowing she was pulling this young man's strings than from the expertise of his touch. "Mmmm, that's it Tommy! That feels good! I like it when you pinch my nipples! Oooohhhh, yessss, just like that!"

Tommy worked her tits for the next twenty minutes as Sandra guided him in how to please her. When he could take it no longer he dropped his head and sucked into his mouth one of her engorged nipples. Sandra moaned as the combination of his teeth and tongue sent shivers through her body. What he lacked in skill, he more than made up for in youthful exuberance. He sucked and nursed on her tits like the hungry man-child he was.

Sandra felt her climax building as her tits were nursed on by her new young lover. But she needed more. She pushed Tommy off her chest. "Would you like to learn how to really make a woman feel good Tommy?" She asked as she caressed his face.

Tommy's eyes lit up. "Yes! Very much!"

Sandra almost laughed out loud as she stood long enough to pull her pants and panties down and off. She sat back down on the couch and lay back, spreading her legs to expose her hairy cunt. "Have you ever played with a woman's pussy Tommy?"

"No ma'am!" he responded almost hyper-ventilating.

Sandra took his hand and guided it between her legs. "Feel how wet you made my pussy Tommy! You did that you naughty boy!" Sandra held his hand against her cunt, sliding it up and down her slit. Within minutes Tommy was stroking her cunt on his own. He loved the feel of her soft, moist flesh combined with the coarseness of her hair. "That's it baby! You stroke mama's cunt! You're going to make me cum baby!" Sandra's breathing started coming in pants as her orgasm built inside her. "That's it baby! Don't stop! Don't stop! EEEEEEAAAAAAHHHHHHH" Sandra's body erupted as Tommy stroked her cunt. Her pelvis lifted off the couch as she instinctively tried to get more of his hand in her cunt. She panted and grunted through her orgasm as Tommy obediently rubbed her pussy.

Sandra finally opened her eyes as she regained her composure. She stroked his face as she tried to build up his confidence. "Oh Tommy! You are such a good lover! How many girlfriends have you had? You must be a very popular boy with the girls!"

Tommy continued to strok her pussy as he responded. He thought about lying but decided to just be honest. He was getting what he'd always fantasized about. Why ruin it with a lie. "I really don't have any girlfriends. Never have. I guess I'm just . . ." He didn't know how to describe himself.

Sandra took his face in her hand and leaned forward to kiss him on the lips. "Don't you worry about that baby. Mama's gonna take good care of you." He continued to stroke her pussy, not wanting the experience to end, as they kissed. "You know what a woman really likes her lover to do for her?"

Tommy shook his head not knowing what she was going to suggest next.

"Women love to have their pussies eaten by a man. Would you like to try that? I'll bet you would be really good at it."

"OK!" he said enthusiastically. "What do you want me to do?"

"Why don't you get on your knees between my legs and I'll show you! Oh Tommy, you are going to make such a good lover!" Sandra wanted to build up his ego as much as she could. "After you've taken care of me, then I'm going to take care of you and give you the rest of your graduation present."

Tommy dropped to his knees between Sandra's legs as he was instructed. Sandra spread her legs like the wanton slut she had become. She then used her hands to spread apart the lips of her pussy. Tommy just stared at pink flesh of her womanhood saturated from her juices. Tommy ran his hands up the inside of her thighs to Sandra's guttural moans. "Oohh, Tommy! A woman loves the feel of a man's mouth and tongue on her pussy."

Tommy leaned into her pussy. "You mean like this?" he asked as he dove into her snatch. Not exactly sure what to do he licked each of her pussy lips several times before sucking one of them into his mouth and nibbling on it. It seemed like something a woman would enjoy. He guessed correctly. Sandra shuddered as his virgin mouth sent wave after wave of sensations racing through her body. He'd remembered a couple of porn movies he'd seen, and how the men in them pleasured the woman. He felt a little nervous and unsure of himself as he worked her pussy. But he desperately wanted to please this woman and prove himself to her. Then he remembered the one scene where he'd watched the guy use the tip of his tongue to flick over the woman's clit. He backed his head off far enough to focus on what he thought was her clit. He then lowered his head again, sucked it into his mouth and began using his tongue the way he'd seen it done. He was rewarded with Sandra's response.

Sandra's body arched up and off the couch as Tommy began working her clit with a newfound confidence. He was determined to prove himself to her. Tommy wrapped his arms around her thighs and held on tight as Sandra's body began to buck and shake. Sandra's moans slowly morphed into a scream as her body built towards its second orgasm. "Ooohhh suck it Tommy! Suck it baby! That's it! That's it! Just like that! JUST LIKE THAT!! YES BABY!! YES BABY!! EEEEEEAAAAAAHHHHHHH!!" Sandra's body erupted for the second time in less than 30 minutes. Tommy kept his mouth locked on her cunt and continued sucking and licking her till she collapsed on the couch exhausted.

Sandra lay there panting and purring like a well satisfied woman. Tommy lifted his head from between her legs. He was wearing a big smile as his face was covered in her juices. He had just brought this MILF he'd fantasized about for years to an orgasm. He was pleased with himself, and his self-confidence was soaring sky high. "Oh Tommy! That was wonderful! You are such a good lover!" Sandra sat up and took his face in her hands. "Now let me give you the rest of your present."

Tommy stood up. Sandra reached for his belt and unbuckled his pants, pulling them along with his shorts down to his ankles. Tommy stepped out of them. "Sit here on the couch baby!" Sandra cooed. Tommy sat down next to her. Sandra reached for his cock with both hands. One hand cupped his balls and began massaging them, while the other slide up and down the length of his shaft. "Have you ever had a woman do this to you before baby?" Tommy shook his head, not able to speak. The sensations were so intense he felt his stomach cramp up. Sandra moaned and cooed as she stroked his manhood. "Oohh, that's it baby! Sit back and enjoy this!" Sandra felt his body tensing as his orgasm approached. She knew he wouldn't be able to hold off. This would be a quick one.

Tommy threw his head back and moaned as his orgasm hit. "OOOOOHHHHHH!!" He was still self-conscious enough that he was unsure how to react. His cock erupted shooting his load all over his stomach. Sandra continued stroking his male meat, smiling to herself as she watched his seed shoot all over his body. Jet after jet of his male cream landed all over his stomach and chest. Tommy felt his legs cramping as his body reacted to the intensity of the orgasm. His first at the hands of a woman.

Sandra let his cock slide from her hands as she sat back smiling at him "Did you enjoy that?" Tommy just nodded his head as he tried to catch his breath. "Good! Now you better clean up and get home. We wouldn't want anyone to come looking for you. Now would we?" Sandra smiled at him. She was finished with him for now. "Maybe if you're a good boy I'll let you fuck my pussy or mouth next time." She knew if she kept him hoping and guessing she'd keep a greater amount of control over him.

Tommy's eyes lit up. "You promise?!"

Sandra stroked his face. "Of course baby! I'll take care of my lover! Now you better get!"

For the next two months Tommy visited Sandra on a regular basis. Always performing the same ritual for her, satisfying her needs. Each encounter ending with her giving him a nice hand-job with the promise of something more next time.

Tommy's older brother, Tyler, noticed him mopping around one day after his return from Sandra's house. He was in his second year at State College and played starting linebacker for the football team. Physically Tyler was just the opposite of Tommy. He stood at 6'3", weighed 230 lbs, and was all muscle. Tyler recognized that something wasn't right with his kid brother. Tyler had always been overly protective of his younger brother.

"Hey little brother! What's going on? I don't like it when my kid brother looks like he just lost his best friend! What's with that?"

Tommy became defensive and scared to say anything. "Nothing! I can't talk about it!"

Tyler got a serious look on his face. "What do you mean you can't talk about it? You're my kid brother! You can talk to me about anything!"

"I don't want to get anyone in trouble!"

Tyler knew immediately this was something much more serious than just a stupid choice teenagers make. "Look at me!" Tommy looked up at Tyler. "You are not going to get in trouble. Tell me exactly what's going on! And I want it now."

Tommy began retelling his story of the last two months. It felt like a huge weight was being lifted off his shoulders as he told Tyler of every encounter and how Sandra kept promising certain things, but never delivering. Tyler sat there quietly without reacting, his anger simmering. This bitch was using his kid brother to satisfy her needs. That didn't bother him as much as her playing him along just to keep him her boy toy. Tyler listened through the entire story, not interrupting his brother once. As Tommy brought his story to a close he vented his frustration. "What bothers me the most, and what's really got me worked up, is that she keeps promising me stuff and never delivers on it!"

Tyler continued to sit quietly as he thought about how to help his brother. "When's the next time you're supposed to go over there?" he asked.

"I can go over anytime. But we had talked about tomorrow afternoon for our next get together."

"Alright little brother! Here's what we're going to do."

Sandra squealed as Tommy ran his fingers in and out of her dripping cunt, sucking on her swollen clit. "OOOOHHHH! That's it baby! That feels so good! You're gonna make mama coke mama cum!" Tommy worked her cunt through two earth shattering climaxes for Sandra. He had learned what she liked and he delivered.

After he had satisfied her sexual cravings he stood there in front of her as she sat on the couch catching her breath. "When are you going to give me the blowjob you keep promising?" he asked with a defeated tone to his voice.

Sandra sat up and began unbuckling his pants as he stood there. "Soon baby, soon! Now let mama take care of that itch between your legs." Tommy remained standing as Sandra pulled on his cock till he shot his load all over her hands and arms. "Now wasn't that good baby??"

Tommy smiled as he pulled his pants up and got ready to leave. "Yeah. That was real good." As he walked out of the house and across her yard towards his own, Tyler joined him. "Did you get all that?" Tommy asked.

Tyler held up the mini-camcorder with a triumphant smile. "I got every fucking minute of it." Tyler quickly downloaded to his laptop when he got in the house and reviewed it to make sure it was usable. When he was satisfied it was he copied it six times to six different flash-drives. "I'll be right back little brother. Wait here!"

Tyler walked back across their lawns again towards Sandra's front door. He knocked. Sandra opened the door with a smile on her face. "Well hello Tyler! It's good to see you! What can I do for you?"

Tyler didn't say a word, nor did he return her smile. He held up one of the flash-drives to her. "This is for you! Look it over! I'll be back in an hour."

Sandra took the flash-drive, not knowing what to say or what was going on. She walked into her living room, plugged the flash-drive in and began to watch her world crumble. Her stomach began to knot up as she watched herself being pleasured by Tommy. She began to shake as the video showed her pulling his pants down like some wanton slut and then pumping his cock like a cheap whore.

When Tyler returned one hour later, Sandra was sitting in the living room sobbing. Tyler didn't even knock at the front door. As he walked in, Tommy was directly behind him. Sandra looked up with a defiant look, trying to maintain a semblance of dignity and control in a situation in which she had neither. "So what do you want?" she asked defiantly. "Money?"

Tyler laughed. "You've to be kidding me bitch! No! I don't want your money!"

"Well what then?" she screamed.

Tyler's anger flashed. "I want you to ruin you! I want to send one of these flash-drives to your wealthy husband and watch him throw your slutty ass out on the street!"

The color and defiance drained from Sandra. "No! Please! I'll do anything!"

Tyler chuckled as he watched her demeanor change with one simple statement. "I know you'll do anything. But before we get to that, let me lay it all out for you so you know exactly where you stand. I've got multiple copies of this. I'm prepared to send a copy to your husband, and one to each of the civic groups you belong to. I know how important your status in the community is to you."

"NO PLEASE!!" Sandra sobbed. The tears were flowing like a river now.

"Shut up and listen to me!" Tyler yelled. Sandra tried to control her sobbing. "From this point on you belong to me! Do you understand?" Sandra shook her head in acknowledgment, not knowing what alternative she had at that point. Tyler looked over at Tommy and laughed. "I don't think she really understands yet. But she's about to." He turned his attention back to Sandra. "Stand up!"