Mom's Motivation: Daughter's BF

"I'm serious," Joel said, shocked to be hearing that this perfect woman, beautiful in every way... mind, body and spirit, could be insecure. "You have an amazing body."

"You think so?" Stephanie asked, playing vulnerable.

"Yes indeed, you don't look anywhere close to your age," he said. "Trust me, my mother is your age, and you two look nothing alike."

"Oh yes, harder, fuck my ass harder," the onscreen MILF demanded, moaning like crazy.

Stephanie knew that was true; she'd only met Joel's mother once, but she was a large woman; very nice, but who nonverbally had judged her for what she did for a living, and for being divorced. Joel's mother was still married, and was a nurse.

"That's so sweet," Stephanie said, deciding to play a scene right out of the awesome Michael J. Fox movie 'Secret of my Success', with Joel being the overwhelmed young man played by Fox, and she the sexy seductive MILF Vera Prescott, played sensually by Margaret Whitton (there's even an amazingly sexy montage, where she teases him relentlessly in the limo in a very sexy nylon scene). "But I know I can't compete with the younger girls." When in truth she knew not only could she compete, but could out sexy, out slutty, and out fuck any of them. She asked, as she cupped her huge double D tits, "But do you think these are firm, Joel honey?"

Joel was paralyzed with shock. This was the kind of thing that only happened in some badly scripted porn film. "They look v-v-very firm, Ms. Friesen."

"I told you to call me Stephanie," Stephanie corrected, holding her tits up immediately in front of the wide-eyed college boy.

"S-S-Sorry, but they do look really firm, Stephanie," he corrected himself, having known from the beginning of this visit he should leave, knew that wherever this went it would be wrong, but his stockinged feet felt glued to the floor. There was no way he was going anywhere!

"Thank you, but do they feel firm, Joel?" Stephanie asked, snatching downwards for his hands and placing them on her tits.

Joel was speechless! He couldn't believe this was happening! He couldn't believe he had his girlfriend's mother's breasts in his hands.

"Squeeze them, Joel," Stephanie ordered. "Just like you would grapefruits in the supermarket to see how ripe they are. Do they feel nice and firm to you?"

Joel mindlessly obeyed, his cock really raging, feeling pleasurable pulses in his pants, as he test squeezed those gravity-defying tits.

"Well?" Stephanie asked, loving the look of awe and wonder in his eyes.

"V-v-very firm," he stammered, as he kept squeezing them as if they were indeed perfectly ripe grapefruits.

"And how about my ass?" she asked, taking a step away, wanting him to want her even more. She bent over, presenting him with the most amazing up close and personal view of her ass, with her pussy folds now peeking out at him. "Is this elderly broad's ass still firm?"

"Oh God, it's very firm," Joel said.

"And my legs?" she asked, really loving the power she was exerting over her daughter's boyfriend as she stood up, draped a leg across the coffee table and ran her hands over her sexy, sheer leg. "What... do... you... think... about... my... legs?"

"T-t-they're amazing," he stammered, and then blurted out for some reason, "especially in those nylons."

"You also like my nylons?" she asked coyly, not having previously noticed him checking out her legs when he was over... he'd undoubtably sneaked admiring looks at her tits, but she hadn't noticed him checking out her legs... although most guys did, so it didn't come as much of a surprise.

"They look very nice," he said stiffly, in spite of her flaunting all her charms so forwardly, terrified of doing or saying something wrong, but nevertheless unable to keep from staring at her sexy legs and feet in the sheer black nylons. He hadn't known such nylons existed outside of porn, and seeing them on his girlfriend's mother had him in awe and lust.

"Come feel them," she offered, knowing he wanted to.

"I shouldn't," he said, admiring them as if in a trance.

"You've already felt up my tits, Joel," Stephanie pointed out bluntly. So you can also feel my legs through my nylons. We both know you want to."

"But... you're my girlfriend's Mom," Joel pointed out the obvious. It had taken him a while to get around to mentioning that... meaning she was entrancing him beyond his ability for rational thought.

"So? That undeniable fact gives you the opportunity to see and feel more or less what Haley looks like without her clothes on," Stephanie said; it was true they had very similar bodies, although her daughter's tits were much smaller.

Joel knew everything that was happening was wrong, everything ever since he'd arrived was wrong; morally and mentally he knew this, but alas for his morality, it wasn't the head on his shoulders guiding his actions anymore... it was the lower head... and the lower head was making it clear that what he wanted more than anything right now was to feel those sexy legs in those sexy nylons.

Joel didn't say a word as he came forward, bent down, and ran his hands over her sheer, nylon-covered legs, unable to express how sexy and soft they were to him.

"You know, I have to work out every day to keep my body in this kind of shape," Stephanie said.

Joel heard her words, but he didn't process them as he prayerfully said, feeling he might come any moment just from excitement, "They're so soft!"

"Nylons are a great way to showcase my legs," Stephanie said.

"Yes," he replied, unable even to attempt a conversation, his brain complete mush from his complete obsession with the nylons he was touching, the legs he was touching, and the naked body he was touching.

"I've told Haley she should wear them, but she won't," Stephanie said.

"I know."

"Oh yes, come in my asshole," the MILF demanded, and then addressed her daughter wickedly, 'See? This is how you should please your fucking man!"

"Shoot, I guess I should shut that off," Stephanie said with a playful laugh, bending down and closing the laptop while Joel kept gliding his hands up and down her leg.

"So if you haven't seen my daughter naked, I'm assuming you also haven't fucked her," Stephanie said bluntly, using language a mother never does with her daughter's boyfriend.

"What? No," he said, shocked at her blunt question.

"But of course she at least sucks your cock and swallows your load?" Stephanie asked wickedly, pretending this was just common sense, even though she already knew differently, "or welcomes your warm, soothing facials?"

"No, never," he denied, shaking his head, about to come in his pants without even having his dick touched.

"Jesus Christ!" Stephanie declaimed as if personally offended. "Then at least hand jobs?"

"Nooooooo," Joel moaned, while he did spew his load.

"Did you just come in your pants?" Stephanie crowed, loving the power she already had over him, and now anticipating really getting him off!

"I-I-I'm so sorry," he apologized, standing up and turning to leave... shame coursing through him.

"Get back here, boy," Stephanie ordered, placing her hands on her hips and standing with her feet shoulder width apart, presenting him with an amazing view of her impressive frontal nudity.

"I really should go," he said, terribly embarrassed at ejaculating in his pants, and also feeling guilt rushing through him for kind of cheating on his girlfriend... although he really had no idea how he'd describe what had just happened.

"No way; we need to talk, sweety," she disagreed, walking right up to him and taking his hands in hers.

"I'm so sorry," he said.

"For what?" Stephanie asked, actually feeling a little sorry for him for always getting cock blocked by her daughter.

"For coming in my pants just now, and for drooling over your hot bod and objectifying you," he said, feeling so humiliated.

"First of all, I'm extremely flattered that you came in your pants," Stephanie said.

"You are?"

"Yes, because the only reason you could have come in your pants, and without any physical stimulation to boot, is because I turn you on, and more than just a little."

"I can't deny that! You're so beautiful," Joel blurted, in complete lust with this woman, "and your nylons are so soft, and your dirty talk was so seductive."

"You even liked my dirty talk?" she asked, even though she knew almost all men loved a woman bringing a filthy mouth into the bedroom.

"It's very different," he said.

"Different from my daughter you mean?"

"Yeah," he nodded.

"So have you ever fucked any girls?" Stephanie asked bluntly.

"Yeah, a couple of them," he said, although both were only a couple of times each.

This perplexed Stephanie. Surprised her too. He was decent looking. He had a good body. He was outgoing. It was hard to believe he'd gone through high school and part of college only getting laid a couple of times. Poor guy. At his age he was supposed to get laid all the time.

"But from what you said earlier, they weren't naked."

"That's right, they just lifted their skirts and moved their panties aside."

"How about blow jobs?"

"Once on a bus once, coming back from a debate," he admitted, not mentioning it was from the very chubby Tara, or that he'd lasted less than two minutes. But on the good side, the feel of her mouth on his cock was amazing as he was coming... so much better than his hand. Every orgasm since that bus ride had been anti-climactic... well, that wasn't literally true... he'd definitely climaxed each time... but they just didn't live up to or even come close to replicating the pleasure Tara had given him that time.

"I see," she said. "Next topic. I know you've been doing your best to talk my daughter into having sex with you."

"Oh, God," he said, his red face somehow going even a darker shade of red. "And she's been complaining to you about it? Now I really have to go, if you're about to give me that talking to!"

"No, don't go; I get it," she said. "You're twenty. You're a college man. You have needs."

"Yes, but I'd never push her into doing anything she isn't ready for," he said, and meant it. Sure, it drove him crazy that she wanted to wait, but he loved her. She was an amazing woman. They had so many other things in common.

"I know that," she said, "because you're a gentleman."

"I try," he shrugged, having been called a nice guy his whole life... a description that could be a compliment or an insult, depending on who was saying it. Bad boys got laid. Nice boys held hands.

"But you get frustrated and horny because she doesn't put out, don't you?"

"Well..."

"Always tell me the honest truth about this and everything else. I'll know if you're lying."

"Well, yeah."

"And here's a little secret: Haley knows that you're horny, and she told me she's afraid she'll lose you because of it. So tell me something else: have you ever felt tempted to at least cheat on her? Again, the truth now."

"Ummmm..."

"Don't worry, you don't have to say it; I can see it in your eyes. So I have a rather unorthodox idea."

"Oh? What is it?" he asked, still having a hard time maintaining eye contact when her huge tits were still right out in the open and staring back at him.

"I mean it's a very unorthodox idea," she stressed. "More of a proposal, really; or even more accurately, a proposition."

"Tell me," he said, almost begging, since with all the buildup, he was really wanting and needing to know!

"Well, since my daughter won't give you what you need, and since I'd really hate it if you dumped her for some hot skank at college, or even just cheated on her with one," she said, deciding the risk of making this offer was a better bet than not making it and thus chancing his dumping her daughter, "you can fuck me instead!"

His eyes went wide.

He'd heard the words, but didn't believe them.

No way was this hot mother offering to have sex with him!

No way!

"So what do you think, stud?" Stephanie asked, grabbing his cock with her left hand... which was still housed inside his jeans, but not for much longer... and she was happy to discover it was still hard and felt impressively large.

"Ooooooh," he groaned, a chill going up his back at the hottest woman he'd ever met in real life squeezing his cock.

"Nice cock, Joel," Stephanie said. "It's a shame my daughter hasn't discovered the joys of playing with a big dick."

"Yes, Haley. What about her?" he asked, this offer a dream come true, seeming even too far-fetched for a porn film... yet it was real.

"We're doing this for Haley," she said, dropping to her knees and fishing out his cock.

"We are?" he asked, as this dream come true kept right on coming visually true right before his eyes. He wanted to pinch himself, but he didn't, in case this was a dream.

She pulled out his dick and said approvingly, "This is a very impressive cock."

"T-T-Thanks," he stammered as she began stroking it.

"You're good for Haley, and she's good for you," Stephanie explained as she stroked the nice hard cock. "So since she can't in good conscience give you what every man needs, at least not yet, I'll have to step in for her until she is ready to do it."

"You're really sure about this?" he asked, watching this beautiful naked woman stroking his cock.

"Well, there is one great big if. If I promise to suck your cock regularly, and also to take it in my pussy and my ass, will you promise not to touch any other girl except for Haley whenever she's ready?" Stephanie negotiated wickedly, a moment before starting to lick the thick shaft.

"Y-y-yes," he stammered, "I-I-I can certainly promise that!" He was stunned to hear what she was offering, especially the part where she added her ass into the mix without his even asking for it!

"Then we have a deal. Whenever you need to drop a load, you just come to me," she said as she swirled her tongue around his cock head. "And I do mean whenever! Don't you dare ever stay away just because you think you're coming to me too often. I love to have sex, so I'll always enjoy fucking you just as much as you'll enjoy fucking me. And I'll also teach you all the best ways to please a woman. Do you want to learn how to please a woman?"

"Wow! Yes indeed!" he blurted out, just as she took his cock into her mouth. "Oh God," he groaned, now happy about creaming his jeans earlier since if he hadn't, he'd be coming in her mouth already.

"Mmmmmmm," she purred, as she took all eight of his inches in her mouth.

"I still can't believe this is happening," he said as he watched his girlfriend's hot Mom sucking his cock. He'd imagined Haley doing this many times, and also many times Stephanie doing it... he'd always assumed eventually he'd live out the fantasy of Haley doing it, but never in a million years could have fathomed the other fantasy coming true.

"I'll do absolutely anything to ensure you don't leave Haley, so if you'd ever like to try something particularly kinky, be sure and ask me," Stephanie said, briefly taking his cock out of her mouth to speak before returning to sucking the big dick, looking forward to swallowing his load number two. Even knowing Haley wouldn't understand why she was doing this, which was why she couldn't ever find out (she knew it wouldn't ever go as well as it sometimes did in the 'My Wife Caught me Ass Fucking her Mom' series), she also knew Haley would be devastated if she lost Joel, which would then affect her grades, her college career, and even more, since she had a history of depression issues.

Joel just moaned while Stephanie's mouth gave him pleasure unlike any he'd ever experienced!

After a couple minutes of bobbing, Stephanie stressed, "Of course nobody can ever find out about this arrangement, Joel, especially Haley."

"Of course," he nodded, looking down at the hot MILF.

"So which would you rather... would you rather comedown my throat, or all over my face?" Stephanie asked wickedly.

"Golly, I don't know," Joel said in confusion, "either would be great!" this wild afternoon still getting wilder and wilder.

"Look Joel, here's Lesson Number One in pleasing a woman. A willing woman such as Haley will be for you someday, and like I am right now, appreciates a man who knows what he wants," she said. "I'll happily suck your dick all day if you tell me to, but you need to assert some control."

"Really?"

"I know I come across like a strong, independent woman, and I am one," Stephanie said, as she kept stroking his cock, "but whenever I'm intimate with a man, I become submissive, obedient, and an absolute slut, longing for my man to take me and use me however the fuck he wants."

"Really?" Joel repeated. In many of his jerk off fantasies he did become that man... dominant... just taking what he wanted. He'd imagined face fucking Haley if she allowed it, or bending Stephanie over a kitchen table and just slamming his dick in her pussy... yet after he came, he always felt bad about harbouring such demented thoughts.

"Joel, you're a man, and a man needs to lead his woman."

"I just don't know," he said, still tentatively.

"Okay then, if I need to be the one breaking the ice this time, I'll do it! I order you to face fuck my mouth, Joel," Stephanie demanded. "Shove that big cock all the way into my mouth and down my throat, and then do it again! Grab hold of my head and face fuck me! Use me like a cheap whore! Then when you're ready, come in my mouth or shoot a big load all over my face, and I don't care which, so long as it's your decision!"

"Fuck," Joel said, all her nasty talk enough to entice him out of his nice guy shell and into his fantasy bad boy persona. Well... at least a step or two. He slid his cock into her mouth and grasped her head with both hands... far too gently at first... but at least he began slowly to fuck it.

At first he was still tentative; he was fucking her mouth, but only slowly, more like making love to it. Stephanie first bobbed more vigorously to goad him along, then grabbed his ass and pulled him irresistibly forward, until all eight inches were tickling her tonsils. Years of experience meant she could easily take eight inches without gagging (meaning three of those inches were down her throat), and while holding her breath, she held his entire cock in her mouth and beyond for a good thirty seconds!

Joel was in awe of her entire surreal tour de force! Then when she backed away, he took her actions as a challenge and assessed, seeing her excessive saliva dripping off of his cock, "A demonstration like can only mean you want me to really face fuck your mouth!"

"Yes baby, that's exactly what I want," Stephanie purred, looking up at him. "Give me all of that cock with everything you have! Fuck my face like an insane person, I want to feel your balls careening off my chin!"

"Shit, then if you really want it..." Joel warned, finally getting drawn into this debauchery and shoving aside away any tentativeness in his actions.

"Yes, go right ahead and shoot for the moon! I want you to use me every which way you want."

"Okay then, you asked for it," he drawled, and slid his cock back into her mouth. This time, like he'd seen in some porn films, he grabbed her head in both hands and really began to fuck her mouth. And still never having fucked anyone the normal way, this was a completely surreal experience. He felt a surge of power and an intense rush of adrenaline because of this very moment becoming a man... a bad boy... and not some pussy whipped nice guy.