Mom's Best Friend

Comments and feedback are appreciated. If enough people enjoy the story, I'll write a 2nd part.

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Maddie was snuggling against Tyler's shoulder as he was playing a video game on the couch. They had a bit of an argument earlier that day when their sex session turned into what she had deemed to be 'too big a production'.

She'd refused to let him tie her up and did not seem to get into it beyond the quick orgasm she received while he tongued her.

Once she refused to reciprocate oral sex, Tyler finally gave up. He stopped the session - never started it really - with a raging hard-on and had been brooding for the past thirty minutes.

Finally, Maddie had enough of his attitude and told him to have fun with his TV before leaving the house. He glanced at her on the way out, her jet black hair dropping as she bent to grab her purse. She looked hot wearing nothing but a tube top and tight shorts; the summer outfit for LA residents.

She looked hot alright, but was she worth the headache?

He'd been into domination even before he'd hit puberty and now, in his last summer before college, had bloomed into a handsome young man, irresistible to many girls.

His good looks had allowed him to sleep with several girls, half of which had been willing to get into bondage and humiliation before receiving an orgasm as a reward. Most girls he'd met had been into it but Maddie could be the exception that broke the rule...

He paused the game and stared at the ceiling. Tyler lived in an affluent neighborhood with his mom and stepfather, although he rarely saw the latter. As a matter of fact, he couldn't even remember where Hank, his stepdad, had flown to this week - was it Japan or Qatar? Either way, he would return soon, only to get back on the road again.

His Mom, Trish, on the other hand, was always home with a swarm of friends, each hotter than the next one. They were either on their way to the gym or discussing the benefits of the latest anti-aging cream, the one not yet available to the public.

Trish's BFF was Amy, a dirty blond, California-native that could have played a part in any beach-tv series. At five feet seven with pulpy lips and a rock hard body, she'd make most sane men turn around on her path. In her mid-thirties, she worked hard to stay in shape and had benefited from a trust fund that guaranteed she'd only have to work if she wanted to. She had the easy-going attitude of a woman that had no financial trouble but tried to hid the void of companionship in her life.

Tyler was lounging in the living room, looking at Amy and his mom who were chatting in the kitchen, bottles of wine and champagne on the counter. It was early in the day, but it seemed that his vacations meant that they were also on holiday.

"Hey Amy, do you have any cool games on that iPad?" He asked, seeing the corner of the device stick out of her purse as he grew bored with the selection he had on hand.

Tyler's mom said, "You should take care of that girlfriend of yours instead of playing games... One day, she'll just leave you."

Amy piped in with a smirk, "Maybe she should learn how to be appreciative and take care of her man." She then took another swig of the champagne cocktail she had concocted.

"What the...!," Trish said, shooing her friend with a napkin, "He doesn't need to hear that. He's cocky enough," exclaimed Trish.

"Meh... She's not the one. Can't you tell?" Amy said nodding towards her friend's son.

She then answered Tyler, "I think there's a good puzzle game; hang on." She unlocked the tablet, started the game, and handed it over before going back to her conversation and her drink.

He started the game and almost immediately got bored. Mechanically, he went to the browser and the sites she had recently visited were still active; a half dozen tabs, the last of which was a news site. Out of curiosity, he looked up the other tabs and almost lost his shit when he saw that she had kept a few porn sites open.

Fucking A.

"Be cool, be cool. Act like nothing is going on", he thought.

Three of the pages had displayed videos and while he couldn't risk playing the movies, a quick look at the titles told him all he needed to know. "Handcuffed and leashed amateur", "Oral services" and "Loving the abuse" were the main ones.

Tyler discreetly pulled his phone and took pictures of the site to easily find them and look-up her username.

"What do you think?" Amy asked from across the room.

"Meh..." he answered, glancing over as she stood straight, looking in his direction.

He put the game back on and just left the tablet on the couch before nonchalantly heading back to his room.

"I think it's probably a girl's game," he quipped with a smirk, trying to get a rise out of Amy and an eye-roll from his mother. It didn't fail with the latter as she responded,

"What a macho! just like his father, I swear..." And then she added, "Where did I go wrong?"

Then she smiled, as she always did when his son acted that way, so proud of her alpha boy.

"What, too complicated for a boy's brains?" Amy shot back to Tyler.

"Riiight... Ok, I'll see you later... Stuff to do," as he ran up to his bedroom to be alone with his trove.

He looked up her web activities and the porn site he visited. Her username was PrettyTiedUp and while it didn't seem she had uploaded any video, he could see her "favorites".

There was a wide range of themes, but it was clear that humiliation and domination were the main ones. He reviewed more titles in her list of public favorites videos describing women that were "Forced to suck", "Cumslut at the bar", "Tied and tried".

Amy? Amy being into that? Boy, what he'd do to see it.

It wasn't hard to think of Amy as a woman rather than his mother's best friend: he'd jerked off fantasizing about her too many times to recall. First, because she was gorgeous and had always seemed to have a soft spot for him. Seconds, she was always wearing tight and revealing outfits. He could tell his mom lived vicariously through some of her stories... At least that's what Tyler thought when he saw the two of them giggle as they chatted in the backyard, Amy gesticulating and sometimes miming obvious re-enactment.

His brain was working overtime. God damn, he would love to bag Amy. Now, that was a woman, not a girl like Maddie.

He started wondering if he could use one situation to get to another.

He laid in bed for five minutes, picturing Amy's face on some of the videos he was watching. He had a raging hard-on and the impulsions of a young bull.

Without a real plan in mind, he thought he heard the patio door close and went back downstairs.

Trish was on the phone with his step-dad, which was bound to last a while. She had gone in the yard and could be heard talking to Hank. One thing was for sure: while his mom could certainly fit the title of a trophy wife, they were a tight team and conversed daily about a wide range of topics. He always reached out to get her point of view.

Tyler decided to play it cool and grabbed a glass from the kitchen counter, pouring a half flute of whatever champagne was on the table.

"Easy tiger," smiled Amy. She was probably at the end of her second one and had glided past 'happy', going straight to 'giddy'.

Tyler leaned against the kitchen island, acted like he wanted to ask something but closed his mouth again.

Amy picked up on it and said, "What?"

"What what?"

"You got something on your mind?"

Tyler looked down and said, "Nah... you'll make fun."

Amy sensed this could be serious and perked up.

"I won't, Tile. You know I wouldn't." She'd call him 'Tile' for a long time and had always been considered the aunt he never had.

Amy could tell he had waited for Trish to be on the phone and that this was pretty important.

Both were now leaning against the kitchen island, looking outside to the back of the chaise-lounge Trish had laid on.

They stood side by side for a moment before Tyler started, "You swear you won't make fun?"

She hooked her pinky in the air as proof.

"Or talk about it with mom? Or think I'm a pervert?"

"Uh-oh," thought Amy, hoping not to hear anything too far gone.

"Pinky-swear," she said as he hooked his finger onto hers.

"Maddie wants me to dominate her in bed."

He waited until Amy looked at him, puzzled.

"Ok," she stated with a tone indicating that she was waiting for him to state the problem.

She was amused that he was bringing this up. "Kiddo," she thought, "you could tie up most women anytime you'd want."

"Her ex was apparently really good - at least she keeps talking him up, and I'm kinda nervous about the whole thing."

Amy realized that Tyler was far from the kid she watched grow up over the past few years. He was a young man with very different problems than she'd expected.

"Well, she's a bitch for doing that and should know better," Amy snickered before gulping a little more of the Champagne than she should have.

"I just don't know if I'd be any good at it. I've thought about it a bunch, but that's not the same." Tyler was pushing the pity card almost too far.

"Well, most of this is instinctual... Trust your gut, establish boundaries and you'll be fine."

Amy was very comfortable with the discussion. Hell, there were not a lot of areas where she'd be considered an expert - but this one? Yeah, sign her up.

After thinking some more, she added, almost to herself, "Boundaries would have been good for me too a few times, let me tell you."

Ok, she was buzzed and needed to shut the fuck up.

She looked at Tyler. God, he was a handsome prick. Kid was going to be a stud and fuck his way through half of West-Hollywood by his twenty-first birthday.

"I wish I'd done it more before... just to get comfortable, you know?"

"Well, what have you done before? Maybe you can build on that."

There was an embarrassed pause, and then Tyler said with a smirk, "Mainly jerk...er... watched porn videos showing BDSM scenes. I don't think that makes me an actual expert."

He wanted to show her he knew some terms at least and was not a complete newbie.

"Wow! TMI, TMI!!" Amy said with a smirk.

He looked at her and said, "Sorry, I shouldn't have said anything."

Feeling bad and without thinking, Amy added:

"Ah Tile, if I was ten years younger, I'd give you a practice round." She immediately thought "FUCK!! SHUT UP!" and put the glass of champagne down, swearing to only drink water for the rest of the day.

Jackpot. Tyler jumped at the bit. He had planned to innocently ask, but she'd done it for him.

"That's such a great idea! That would be awesome!"

"What?" she asked puzzled.

"Letting me practice; oh my god, that's brilliant!"

"Yeah, that's not gonna happen," she answered dryly.

"Why?"

"I could be your aunt. Shit, I'm basically your aunt."

The tension had built up too quickly. With a hillbilly's voice he answered, "Well in them parts, we don't frown upon them kind of relationships."

She laughed and with a more serious tone, added, "Some women really enjoy this, Tile. If she likes you, she'll guide you and it will be fine."

"Easy for you to say. You're not the one who's got to be a top."

"That's true, and I've never had to either," she replied without thinking. "FUUUUUUCK!" her brains screamed.

"See! You'd be great at giving me feedback!" Tyler exclaimed,

Amy was well into buzzed territory and she was thinking of how long it had been since a man had his ways with her. Telling her what to do, pushing her to the limits... It had been a while, that was for damn sure.

"Five minutes," he said.

"Five minutes what?"

"Let me try it on you for five minutes right here just so I can figure out how to get started and if I'm doing well."

"Not a chance, your mother would be furious."

"She'll never know I swear! Just tell me how I sound, if you think you'd get into it, all that stuff. It'd be great to have a woman's opinion." He had turned sideways and was staring at her. She did not want to hold the gaze as the conversation was now uncomfortable but her cloudy mind was negotiating with herself: "What could he do in five minutes?" and "Help the kid out."

She could not deny the allure of being used as a prop slave even if only for five minutes. She had a flash of herself bent over the kitchen counter, ass in the air while the young stud looked her over.

"This is silly, Tyler."

"Please..."

The champagne was not helping her negotiate: five minutes was not long at all - how much could he really do in that time? And Trish was right there, a few feet away from them.

She was making a big deal of nothing: he was going to give her a couple of cheesy lines, they'd laugh and be done.

She looked at him and in a moment of immense weakness, said: "Fine. Five minutes."

"Pinky swear?" he asked with his digit extended. She grabbed it with hers.

He looked at the clock on the wall as he moved behind Amy and told her to keep her hands on the table.

"We're staying here?" she asked surprised, staring at the back of her best friend.

Tyler did not answer.

"For the next five minutes, I am in complete control and you are to obey me in every way. Close your eyes, please, and make every effort to forget that it's me."

His voice was a bit deeper and he did not quite sound like Tyler. She stood straighter and closed her eyes, playing her part and acting as if she was getting in character.

"I am going to find out just how obedient you can be."

"Good luck," she said, wanting to be smug.

There was no reply and the silence became heavy. Her breathing was shallow as she sensed him coming close behind her. She could feel his breath on the back of her neck.

"I'll let this little comment slide, but that will be the only time."

"Oh, come on Tyl..."

The sting was immediate. The mental shock was much worst.

"HE JUST SPANKED ME," her brain was shouting.

Tyler had used his palm to slap her ass, perhaps a bit harder than he wanted but he carried himself as if this was all part of the plan. He checked to make sure that his mom had not heard anything but all looked well.

"As I said, I am now in complete control. If you are disrespectful, if you do not obey or if I just feel like it, I may punish you."

God damn, this was ballsy, he thought. His heart was racing and he could hardly believe the words that were coming out of his mouth. They flowed easily though, as if he had rehearsed this scene many times before.

Ana could feel her cheek get a little warm and was thrown back to her past relationships. Flashes of the men that toyed with her in the bedroom, tied her up, fucked her senseless, and made her come like there was no tomorrow.

The spanking was the trigger of how many sessions began. Damn, she loved it. The kid was audacious and sounded pretty darn good. She was almost immediately and despite herself in a different mindset. It had been a long time, too long perhaps, since she had been properly dominated and the slap on her derriere had reignited the desires to submit.

Tyler put his hands on her shoulders and started rubbing them. His fingers immediately finding knots in her muscles and pressing against them for a few seconds. Amy felt some of the tension leave her body as she let out a small moan. It allowed her to get used to his touch and was a gentle follow-up to the spank.

"I'm going to ask you personal questions that will be embarrassing. This is to check if you will tell the truth. If I feel you are not, I may punish you. Are we clear?"

"Yes... Yes..." She seemed to hesitate.

"Sir," he added, "Call me 'Sir', at least for the next four minutes."

"Y... Yes, Sir," she murmured but repeated it loud enough for him to hear.

"When was the last time you had sex?" he inquired with a flat tone. He knew it was a bit of a weak question, but he liked the simplicity of it.

"Mmm... A couple of months ago..." "I... I think..."

"Long time for you. Was it memorable?"

She felt a pinch when she heard him say that - as if he thought of her as a slut.

"Not really... Mmm..." God, he was good with his hands. His fingers were pressing all the right spots.

Tyler watched the clock. He needed to get to the point. He moved his hands down to her lower back, and grabbing her by the hips, drove his thumbs on each side of her spine. Amy immediately arched her back.

"When was the last time someone dominated you?" And to be more precise, he added, "The last time you were someone's sub. I know you've done it before," he added calmly implying there was no need to deny.

Calling Tyler 'Sir' was like a truth serum compelling her to state facts.

Going through quick maths in her head and said, "Two years." Quickly adding, "Sir."

He left his hands on her hips but stopped rubbing. She relaxed her body. There were three minutes left on the clock.

"Do you still fantasize about being collared? Being someone's personal fuck toy?"

And as she answered 'Yes, Sir', he grabbed her yoga pants and pulled them down to her knees.

She swallowed a shriek of surprise and started to bend to pull them back when she heard, "Don't you dare!"

Amy froze and immediately realized she had already started obeying him. She slowly rose, leaving her pants where they were.

There was a natural degree of embarrassment as she had worked out at the gym earlier and did not feel particularly "fresh". To make her even more self-conscious, it had been a few weeks since she'd shaven her pussy. The humiliation of having to stand there felt part of the course; part of what she had just agreed to a moment ago.

Amy may have been buzzed but she still knew this was wrong. And yet, it felt so fucking good. She had secretly yearned to be back in that state again, submitting to a man that would dictate how she was to stand, what position she had to take. But Tyler?

"Put your hands behind your back, lean on the counter for balance if you have to."

Amy immediately obeyed, grabbing her wrists as a display of submission. To keep steady, she pressed her chest against the kitchen island.

He took a step back to admire Amy's position and snapped a couple of pictures with his phone. There was no desire to blackmail, simply the idea of admiring her gorgeous rear later.

God, she looked fantastic. Amy had great legs, toned to perfection on a bubbly ass. He bent to examine her pussy; she had been trimmed but hairier than expected. Her lips seemed puffy and looked as if they'd be drenched if he pulled them apart.

He slipped a hand between her cheeks and rubbed a finger along her cleft.

She knew this was coming the second she was told to put her arms behind her back and yet she shuddered as the sensation. This was definitely wrong, but she'd already agreed to it when she'd bent forward.

Tyler couldn't quite believe this was happening. It almost felt too easy - he thanked the champagne cocktails, not giving himself enough credit.

He rolled his fingers against her softest flesh, squeezing and pulling her lips, touching her moistness. Her body responded enthusiastically to everything he did, clearly excited.

"The only thing that I did was slap your ass once. Do you want to tell me why you are so wet?" he asked.

"I... I don't know..."

Tyler moved his hand further, squeezing her clit between his fingers, making Amy immediately gasp and lurch backward. He could feel her juices against his wrist.

After a few seconds, he moved his thumb inside her while leaving three digits on her rosebud.

He could feel her tight pussy around his thumb, squeezing it with her muscles.

She moaned heavily; it felt so good to be penetrated. Felt so right to be told what to do.

"Mmmm... That pussy feels nice," he stated.