Fooling with His Best Friend's Mom

"You think I won't?" Jasmine asked the young man sitting on her couch.

Malcolm gave his best friend's mom a lazy smile. "Not in a million years."

Jasmine hated that grin. Hated that she liked it so much. Hated that she wanted to fuck the smile right off his face. In Malcolm's irregular visits when he came home from college, it was like some lightbulb came on. She felt something raw and primal she didn't understand. Malcolm wasn't ugly but he wasn't handsome either. At twenty, he was pretty much a physical wallflower, not fat, not skinny, not anything. But the way he looked at her, devouring her with his eyes, it made Jasmine want to drag him to the bedroom and never stop fucking him. And then there was the way the girls his age looked at him. Whispered about him. Giggled about him. Not at him. They watched Malcolm with secret smiles, the kinds of things that made a woman want to know just what they were smiling about.

It would be an odd pairing to any outside observer. In her late thirties, Jasmine was the definition of a hot mom. She worked hours in the gym every week to keep up a trim waist and a tight ass. Her tits had always been what men noticed first, but it was when they caught a look at her innocent face that they realized what a fuck bunny she really was. Jasmine knew it, and liked it. Liked being the hottest mom at the bake sales, at the games, at her husband's work functions. She liked men drooling over her.

But none of them, not even her husband Francis, made her so fucking wet as Malcolm goddamn Williamson, and she had no clue why.

She did know why he was home. It was their special day, and it happened to fall on a weekend. Ever since Malcolm started hanging around with Loren when they were just kids, he shared a love of April Fool's with Jasmine. The two of them were the only ones in their respective families who didn't see the holiday as a pain in the ass. It started small. Malcolm bought some fart spray -- he was twelve at the time -- and squirted the driver's seat of Jasmine's car generously with it. She put a fake but realistic-looking spider in his backpack, nearly making him pee himself at school when he found it.

The next year, he got her by coming over the night before, ostensibly to hang out with Loren and play games, but in reality to add cayenne pepper to the blender. Jasmine was on a smoothie kick back then, and got a hell of a surprise when she made one the next morning. She got him back for that by driving to the school and bribing her friend May in the principal's office to let her into his locker. She filled it with stuffed animals and left a note on the door saying, "I know you get scared sometimes, so I left you some friends to keep you company. Hug one, and all your troubles go away!" He called her up twenty minutes later, laughing so hard he was nearly crying.

So it went throughout the years until he turned eighteen and the games turned to yearly dares. That April Fool's, when Loren was out golfing with his father, Malcolm came over. On her third glass of wine for the night, Jasmine was pleasantly buzzed and told him she was disappointed there weren't any pranks that year. Malcolm told her he was pranked out, and truthfully, so was she. Then he suggested a game instead. She thought he meant a board or a video game, but no, Malcolm had a different idea in mind. Truth or Dare, but in the years since, it had always been dares.

There were limits then. Malcolm asked to see Jasmine's boobs with a hopeful dopey grin and she laughed him off. But by the end of the night, she agreed to jump on the trampoline in her tight tank, and he watched, stunned and so hard by the time she finished she knew he had to hurt. It made her giggle, and secretly, the thought of the eighteen-year-old wanting her that badly turned her on a bit too.

Then came college, and that vague seed of attraction planted that April Fool's Day blossomed into something more, something darker, more urgent. With every visit, Jasmine had a harder and harder time remembering the sanctity of her vows to Francis. She saw Malcolm, saw the unchecked lust in his intelligent eyes, and a fog of desire slipped through her mind. They missed last year's April Fool's since he was in college and it was on a weekday. But it didn't stop Malcolm from texting her and saying they should keep the game going. She replied with a simple, "How?" knowing full well he would want a picture of her boobs or her ass.

"Do something sexy for me," he responded.

"Little pervert," Jasmine wrote back.

"Yup."

That made her laugh. She meant to ignore his request and let it go, but all day, she thought about those words -- do something sexy for him. It was hot the way he commanded her like that. If she thought about it for overly long, inevitably she started thinking of more, of Malcolm in his dorm room, jacking off to her, to her ass, to her tits, to her smile. And when Jasmine started down that road, a dizzying heat swept through her, making her so wet all she could think about was fingering herself to him. By the late afternoon, she got no work done and was staring sightlessly at her computer when she finally said fuck it, and went into the bathroom to tug up her blouse and take a picture of her tits in her bra. It wasn't anything particularly sexy, so she turned in profile to the mirror, raised the shirt, and made a face like she just came. That was it. That was the one. Before Jasmine could think about it overly long, she sent it to Malcolm with the line, "Now do something sexy for me."

Predictably, he sent her a picture of his hard cock tucked away in his shorts, followed by another of his hand inside his boxers with a caption of, "This is what you do to me." She fucked herself silly to those pictures for two weeks, then the guilt settled in and she texted to tell him they couldn't do anything like that again. His response had been simple. "I'm okay with that. But we have to have April Fool's." After an hour of thought, she agreed.

Now it was April Fool's again, and Malcolm was back. Oh Lord, Jasmine was thinking of some very bad things while he sat there right in front of her.

Like now, his first dare of the early afternoon.

"What do you want to see me in?" Jasmine asked, blushing under his scrutiny.

"Your sexiest outfit," he said. "Something that says you're the hottest mom on the fucking planet."

"Language," Jasmine said mildly.

"Really? Now?" he asked with a smirk.

"Brat," she said, and stuck out her tongue. "You have to phrase it like a dare, or it doesn't count."

Malcolm chuckled. "All right. I dare you to go dress like the MILF you are."

"Be right back."

Jasmine tried not to run to her bedroom upstairs, but it was a close thing. She felt giddy, and more than a little sick. This was far more than just a sext back and forth. This was borderline cheating, and given the way she thought -- hoped -- the afternoon would go, that would probably be a line that she crossed too. And it wasn't that she hated her husband or her son. Francis was a good husband, sweet and funny and a good father. Yeah, maybe he took her good looks for granted and their sex had become stale, but that was just as much on her as it was him. She could have told him some fantasies and he would have acted them out for her.

Similarly, Loren was a good son. He knew his friends liked to look at his hot mom and tolerated it with passably good humor. Sure, there was the usual teenage angst and she wished he was pulling better grades in college but he was, at his core, as kind a man as his father. This would be nearly as much a betrayal to him as it would be to Francis.

If they found out.

Jasmine dug through her closet, looking for just the right outfit. A gown was far too formal. A nightie too informal, though it definitely went into her mental maybe pile. Her little black cocktail dress? Closer to the mark. Jasmine's hand rested on it, then moved across the fabric of a red dress she bought for a cruise. The thin shoulder straps could barely keep her breasts in check, and the hem came to just above her knees. Combine it with some heels and... yeah. That was it.

She changed in a hurry, waves of heat pulsing through her. Her pussy begged for attention but she couldn't give it any, lest she call Malcolm up to the bedroom and tell him to pound her into the mattress right there and then. No, she wanted to play this game a while longer, and maybe pull herself back from the edge.

Yeah. Right.

Jasmine spent a few moments tousling her dark brown hair, kissed at herself in the mirror, and opened up the cabinet to dig out some condoms. But... where would she hide them? She didn't want to seem too desperate. Besides, Jasmine wasn't going to fuck Malcolm. She wasn't. She was going to tease him and give him a show and maybe he'd give her one, and that would be it.

And maybe they'd do some petting.

Some serious petting.

The fact that Jasmine wanted her son's best friend's come deep inside her warm wet cunt was barely a thought in her mind. Her warm... wet... unprotected cunt.

She swallowed.

"Oh God, what am I doing?" Jasmine whispered to herself in the mirror.

You're going to let a barely-legal stud seduce you then fuck your brains out, that's what.

She moaned deep in her throat and pushed away from the bathroom counter to head downstairs, where Malcolm was still languishing on her couch. At the sight of her, he uncrossed his legs and leaned forward.

"Oh... oh wow..." he said.

"Never in a million years, huh?" Jasmine asked.

"Y-yeah," he said, suddenly a shadow of his cocky self. "Fuck, Mrs. Taylor..."

"I thought it might be a little too revealing," she said, and pressed her elbows against the sides of her breasts as she bent over. "It's not, is it?"

"Nurkh." Malcolm cleared his throat. "I mean... no. It's... great."

"Well... you used up your one dare this year. I wonder what I should ask for mine."

Malcolm stared at her chest blankly for a few full seconds before he blinked and looked up. "Wait. One dare? What?"

Jasmine came to the couch and sat beside him. His hand went to her thigh and she moved it to her knee instead. "Yes. One dare. That's all you get. So now I need to think of a proper dare for you. Something... fun."

"Wait wait wait, we never agreed to just one dare."

She laughed and patted his hand. If it moved slightly up her leg, she pretended not to notice. "I got you. April Fool's."

"God, I love you and I hate you all at once."

"I know the feeling. But it's still my turn," Jasmine said. Her eyes flicked to his groin. A tent was quickly forming in his khaki shorts again. "Hm. I dare you... to watch a movie with me."

Jasmine could have laughed as his expression broke. "A... a... movie." He sighed. "Well... okay."

"I wasn't done yet," Jasmine scooted away from him towards the edge of the couch and patted the seat beside her. "I dare you to watch a movie with me with your head on my lap."

Malcolm brightened considerably. "Okay. Yeah. Sure."

She laughed and grabbed the remote. "I'll even let you choose the movie."

He scooted over and took the remote from her. It didn't take him long to find a movie, zeroing in on a raunchy 2000s romantic comedy starring Lea Banner as a hot single mom.

"Mm," Jasmine said as the movie started and he put aside the remote. "I wonder why you picked this one?"

"Because..." Malcolm said, twisting onto his side and resting his head on her thigh. "She's the second most fuckable mom I've ever seen."

"Oh, and who's the first?"

Malcolm turned his head and kissed her thigh through the thin fabric of her dress. "You have to know the answer to that one."

"Tell me," Jasmine said, resting a hand on his side.

"All right. There's no woman in this world I want more than you."

She swallowed, and stroked his abs under his shirt. "Someone as charming as you, you could have anyone."

"I had everyone else I wanted," Malcolm said. Onscreen, the intro showed quick flashes of Chicago, but neither of them was paying a bit of attention. His hand brushed hers, took it, moved it to his hip. "Mrs. Berkley. Mrs. Malone." Her breathing picked up rapidly. She knew those names. Knew that they were MILFs just like her. "Ms. Connors."

"Lindsey Connors?" Jasmine whispered, her thighs parting with a rush of liquid heat. Lindsey Connors was the high school science teacher, an incredibly attractive woman in her early thirties.

"Yes."

"I... play tennis with her." Jasmine's hand moved down closer to the bulge in his shorts. "She never... never mentioned it."

"She wouldn't. Probably afraid of losing her job. I fucked her bent over her desk when she had a free hour and I was supposed to be going to the bathroom. I had to gag her with her own panties, she was so loud." Malcolm chuckled. "I just turned eighteen two days before that. A birthday present to myself." He twisted and looked up at Jasmine, and the motion had the effect of bringing his cock within a half inch of her hand. She raised it, trembling, as he stared her in the eyes. "Some college girls and a professor too but they're not the same as a hot mom. And you... you're the last one I want. The hottest one. The one I've been fantasizing about for so long."

"What do you want from me, Malcolm?" Jasmine asked, faint with the need burning inside her. "Because this can't be a relationship."

"I don't want it to be." His eyes sparkled. "I don't want to wreck your marriage. But I want this hot MILF cunt-" she moaned softly at the filthy word coming from his mouth, the boy who used to be so afraid of cursing around her "-wet and ready for me anytime you know I'm coming home. And when I'm not here, when you need it so bad you can't take it anymore, I want you driving over and visiting me at college so I can show you off to my friends before I take you back to my apartment and fuck you ragged."

"W-why would I do any of that?" she whispered, knowing she would, knowing she would burn for him the rest of her life. She never wanted anything more in that moment than this fantasy.

He took her hand in his. "For the same reason all of them wanted it." Was it his hand or hers that went to his bulge? She could lie and pretend it was his, but she had to know. Had to feel him and find out.

"Oh. My. God," Jasmine whimpered as she gripped his thick, hard cock.

He twisted his head, not towards the movie, but towards her breast, and she thrust out her chest without thinking about it, her hard nipple grazing against his lips. "So I'm going to dare you to give over all your dares to me," Malcolm said. He parted his lips and brought hem to her nipple through the fabric, his cock jumping when he made contact. Against her breast, his voice was a soft caress. "Not just today, but for all time." Jasmine stroked his cock, her breaths coming so hard her chest rose and fell with them. "When I dare you to send me a picture of these tits or this pussy, I want you to do it immediately." He nuzzled the fabric of her dress and sucked her tit again through it. She moved a free hand absently to the strap, already tugging it down even as her mind gibbered at her that she was about to cheat, that this was a line she could never uncross. "When I come home and dare you to put on a bikini so I can fuck you by the pool, you'll only ask me if you should wear a one piece or two." With the image of him behind her in one of the lounge chairs firmly imprinting itself into her mind, Jasmine pulled the fabric away from her nipple and started in on his zipper at the same time.

"W-what else?" she panted.

He thought about that and sucked her tit into his mouth. Crackling heat shot through her and she shivered with need. He sensed it and sucked harder before abruptly popping away from her nipple. Her tit glistened, the image forever indelibly the one she would start her fantasies of this day to.

"When Francis is out back barbequing," he said, "I want to take you upstairs and fuck you on your bed. I want him to suspect. I want him to hear just enough he knows who's giving it to you so good."

She shivered again, thinking about it, the young man plowing into her with her legs kicking in midair as Francis obliviously cooked away outside, maybe now and then hearing his wife pant or curse or wondering what the rhythmic thumping was. If she turned on the washing machine...

"Fuck," she whimpered. "But I love him..."

"I'm not asking you not to," Malcolm said as she managed to get his shorts down far enough that his fat, long cock sprang out. His tip glistened as much as her tit and she licked her lips, wanting to get her mouth on it. "I don't care if you sleep with him or save it for me. But I want you on demand. You are mine first, his second. That's your first dare."

"I never accepted," she said, grasping his cock loosely and stroking him. But she knew the truth. She wanted this as badly as Malcolm did.

"Then I dare you to say yes," Malcolm said, and hungrily devoured her nipple again.

The heat inside her built to a roar. She clenched her teeth as the pleasure hit her hard. Barely had Malcolm begun to touch her but the first orgasm hit Jasmine anyways, her mouth opening, her eyes going half-lidded. "Yeeesss!" Jasmine whined, both to the orgasm and the proposal. His. Forever Malcolm's.

She jacked him harder as he sucked at her breast. She only stopped to spit into her palm. Not that he needed much lubrication. His tip gleamed with his desire for her and provided plenty. Christ, he was big, maybe twice the size of Francis and at least again as thick. Shaven too, a look she had never seen on a guy in person. She liked it. No hair to get in the way of what she wanted to do later. Oh God, the thought of Malcolm shooting into her mouth nearly brought her to the edge again. She was going to come so many times that day.

His hips met her fist. Thrusting up at her, he moaned around her nipple and sucked harder. He broke away and growled, "I dare you to unlock your phone and give it to me."

Her feverish mind told her this was a bad idea. Or was it the best idea? Jasmine didn't know which and was too turned on to care. She picked up the phone, punched in her passcode, and handed it to him. He raised it over his head and took a picture as he started sucking on her tit again. Click click click. Then he turned so he could see her jacking him off and got a picture of that too.

He pushed up off the couch and Jasmine moaned in need. He hurried right back to her, the phone in hand, jerking his own cock while he took a picture of her with her tit bared, her cheeks flushed, and her lips parted. Her hands took him again and jerked him harder, faster. Click, click, click. There would be no mistaking her for anyone else if those got out. She didn't care. She wanted more. She wanted him to do every filthy fucking thing he desired. She would give him everything.

Everything.

If Francis or Loren walked in that door right then, she'd still jerk Malcolm off. She was desperate for this, her whole body thrumming with black desire, and she nearly cried out for joy when he grunted, "I'm close. I want to come all over your tits."

She hurried down the other strap on the dress and jacked him against her nipple, her mouth parted wide, her mind floating on a thousand embers of wicked desire. He gritted his teeth and aimed the phone, snapping picture after picture as he started to come, great big gobs of him streaking her tits, her nipples, her chest. She let him go and grabbed at her own tits, rocking back against the couch at the feel of the warmth of him, her son's best friend's come, holy fuck, this was wrong, this was wrong, this was so fucking wrong.

Then he was moving too, dropping the phone beside her before falling to his knees and yanking her dress up. Jasmine spread her thighs wide for him. He grabbed her flimsy excuse for panties and ripped them away from her, pocketing the material and driving his tongue between her slick, thick folds.