Helping Mom's Best Friend - Cover

Helping Mom's Best Friend

by Ashley

Copyright© 2026 by Ashley

Erotica Sex Story: Amanda was more than happy to volunteer her son's assistance when her best friend, Lauren, needed his help with a costume fitting. So was Tyler, who'd had a bit of a crush on her for a while. And that was before he realized that it would entail lots of clothing changes, and some delicate minor adjustments...

Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa   Consensual   Reluctant   Lesbian   Heterosexual   Fiction   Incest   Mother   Son   First   Masturbation   Oral Sex   Petting   Tit-Fucking   .

Tyler was in his room, minding his own business. Well, he’d actually just begun to check out, rather optimistically, whether Amber Heard had ever done any porn. Anyway, there was a knock on his door.

He hurriedly switched to a news stream. “Come on in,” he called. It was his mom, and she had her cell to her ear.

“Hi,” he said, and she mouthed it back as she listened to the person on the other end of the call. “Why?” she asked them, and then, after a pause, “Oh, I see.”

“How tall are you?” she asked her son.

“Five eleven,” he answered with a frown of confusion.

“Weight?”

“About a hundred and fifty. Why?”

His mother sort of shook her head at him as she repeated that and then listened some more. “Are you busy this evening?” she asked him.

“No. What’s going on, Mom?”

“OK ... We’ll see you in a bit ... Bye.” She finished the call and then smiled at him. “That was Lauren.”

Tyler had known his mother’s best friend for ... well, as long as he could remember. “Oh, OK. And what was all that about?”

“You know that she’s a seamstress, right?” He nodded. “Well, she does the costumes for the local Am Dram, and she’s got a bit of a problem.”

“OK,” he said slowly. “And that affects me, how?”

“The leading actor has a dose of man flu. He’ll probably be okay for dress rehearsals next week, but she needs to do a fitting of his costume before that, and you’re more or less the same size.”

Understanding dawned. “So she just needs my body, right?”

Even as he spoke those words, he began to get a boner.


His mother had several friends who all met every other Wednesday for what they called a book club, although to Tyler it looked like they were just drinking wine and chatting, with some books scattered about, mainly for the look of it.

Anyway, whenever they were there, and he happened to walk through the lounge, he made a point of checking out what Lauren was wearing. Not that she dressed sluttily or anything, it was just that she was rather nicely built and her clothes fit very well. He didn’t walk through too often, at least he tried not to. Although when he came to think of it, there was often some hushed giggling as he was leaving the room.

As he said to his mate one time, when he may have mentioned Lauren, and Clyde asked what she was like, “She’s not skinny, more curvy, and she’s got these amazing boobs...” Tyler gestured with his hands, trying to convey their impressive size and probably weight, “ ... and her ass is just...” He sighed and could have done with adjusting his pants just at the thought of her wonderful bubble-butt.

“So just like your Mom, then?” Clyde said with a smirk.

“What? No! What?! She’s nothing like Mom! They’ve got different colour hair ... and their faces are totally different.”

“Oh, right. My bad. Nothing at all like your mom, then,” his - possibly about to become former - friend replied, grinning like a bastard.

“Fuck off!” Tyler told him.

“Ow!” Clyde cried out when Tyler punched him rather hard in his upper arm. But it had sown a small seed in Tyler’s mind...


“Well, I’m not sure I’d put it exactly like that, but yes. She’ll be round to pick you up in about fifteen minutes,” his mom was saying as his attention came back from his daydreams.

He sat there after she’d gone, contemplating spending some alone time with the lovely Lauren, idly stroking a cock that was no longer quite flaccid. Don’t be stupid, nothing’s going to happen! he told himself.


The moment Amanda opened the door to her, Lauren realized her mistake. She’d learned over the past few years to always dress ... demurely when meeting her best friend. She wasn’t quite sure when Amanda had become such a prude, but it was easier just to go along with it, rather than put up with her disapproving looks. But she’d been in such a rush that evening that it had completely slipped her mind. The way that Amanda’s eyes narrowed as she took in first the few undone buttons on her blouse, and then the apparently shocking expanse of her lower thigh, made her cringe inwardly, but there was nothing for it but to smile and carry on.

“Hi,” she said breezily, “Thanks for doing this.”

“It’s Tyler you should be thanking,” Amanda responded, somewhat icily.

“Yes, of course,” she replied. Tyler appeared behind her and gave Lauren a smile that had been sadly lacking in his mother’s greeting. He really is quite the cutie, Lauren thought, not for the first time, as she smiled back.


“Thank you so much for doing this,” Lauren said as they drove over to her house.

“No problem at all, Mrs. Collins,” Tyler replied.

“Just, Lauren,” she said, smiling over at him. “Mrs. Collins makes me feel so old.”

“Sure, Lauren,” he replied, taking the opportunity as she turned back to the road to look at her legs. Her skirt had ridden up a little, and she was showing a little thigh. Very nice thighs ... and knees, actually.


“Do you wanna beer?” she asked as they went in through her front door. He was seventeen, and his mom never let him drink at home. Not that he hadn’t had his fair share, though.

“Sure. Thanks.”

“Miller regular or lite?”

“Regular, please,” he responded.

“Good choice,” she said, and came back into the lounge a few minutes later with two beers in one hand and a something very green on a hanger in the other.

When he looked quizzically at it, she explained, “It’s Robin Hood, a British pantomime. And I hope you’ve got clean undies on,” she added, handing him one of the bottles. He swallowed hard as he saw how little of the costume there was: a short-sleeved jerkin and a pair of shorts. He opened the beer and took a long, hard pull on it. When he looked back, she was sipping her own, smiling expectantly at him.

“What?” he asked.

“Try it on then, dummy,” she said, chuckling. “That is why we’re here.”

“What, here?” he asked.

“This is where my sewing stuff is,” she replied, pointing to the table with a sewing machine on it in the corner, “So, yes.” She paused for a few seconds. “You’re not shy, are you, Tyler?” she added, sort of challengingly.

“No, no,” he replied firmly, peeling his T-shirt off over his head, and then pushing his jeans down to his ankles and stepping out of them.

“Good boy,” she said approvingly, and then went closer and blatantly looked up and down his body, even walking around him. Tyler found it quite arousing having her stare at him that way, wearing only a pair of light grey boxer briefs. “You’ll do,” she said finally.

“I’m sorry?”

“You’re pretty much the same build as Hank,” she said. “What did you think I meant?”

“Yeah. Yeah. Just that ... obviously.”

He got into the costume, and it seemed a little big on him. She stood in front of him, cupping her chin with her hand, once again looking at him intently. Then she went over to the table where her sewing stuff was and picked up a small tin. She took a bunch of pins out and put them between her lips, and then came over and stood behind him, gathering material and pinning it tighter to his body. When she was done, she came back around to the front to look at the effect. “Not bad,” she mused, and then got down on her hands and knees, her face only a foot or so from his groin.

As he looked down, he could see down her blouse, and she had a very pretty bra that left the tops of her boobs uncovered. Don’t look! he warned himself, as he felt his dick starting to swell.

“Sorry if this tickles a bit,” she said as she began to adjust the inner seams of the shorts. It didn’t tickle, far from it: her soft hands brushing his inner thighs felt amazing. And she’s working her way upwards! He was biting his tongue and trying to think of the un-sexiest things he could imagine as she got closer and closer to his junk. But it didn’t work. He was sweating as she went up the other leg, now fully erect, and it really didn’t help when the back of her hand brushed against his balls!

“Hmm,” she said, sitting back to admire her work. “Maybe you are a little bigger than Hank,” she said, pretty much to herself while she stared straight at his dick.

After a few very long moments, she stood up. “OK, slip them off, and we’ll see how that works.”

“N-N-Now?” He spluttered. His boner was obvious enough as it was, but in just his briefs...”

“Yes, now,” she replied, folding her arms under her boobs - her quite magnificent boobs - and tapping her foot impatiently.

Short of actually saying something along the lines of, ‘I can’t because you’ve made me hard as fuck’, he didn’t really have any choice. He took it all off and stood there with his hands over his crotch.

She took the outfit from him and then went over to her sewing machine. He kind of assumed that she’d use that, but she just used a needle and thread. After she’d been working for a few minutes, she looked up at him. “You know, you’ve got nothing to be embarrassed about, Tyler,” she said calmly. She was being so cool about it that he felt himself beginning to relax. “You’ve got a really lovely cock,” she added, smirking as she peeked up at him through lowered lashes.

“Mrs. Collins!” he blurted out, ashamed when it came out much higher than he’d have liked.

“It’s still Lauren, please. Besides, it’s not like I haven’t seen it before.”

“W-W-What?!” he spluttered

She stopped her work and looked up at him, grinning. “When you were a baby, I used to change you sometimes. Your little cock and balls were adorable,” she said, a faraway and very fond look on her face as she remembered those days. “And rubbing baby powder into all the little nooks and crannies...”

Tyler had a vision of her doing that now, and his hardon, which had been fading, came back with a vengeance.

“You’re much, much bigger now, of course,” she said, once again peering as she tried to see what his hands were covering. She pouted and frowned, and then did something that he couldn’t believe: she undid two more buttons on her blouse, and separated the sides, showing off a truly beautiful cleavage. “It’s only fair,” she said, smiling sweetly and looking pointedly at his hands. She is so coming on to me! he thought, and then moved his hands away. Her smile widened. “That’s much better,” she said, giving his groin a long, lingering look before carrying on with her work.

“So, Tyler, do you have a girlfriend?” she asked.

He let out a breath as they came back to safer ground. “Yes. Grace.”

“Is she pretty?”

“Yeah, she’s very pretty,” he replied, and he couldn’t help the little sigh that slipped out.

She glanced up at him. “So Grace won’t let you do it, then, huh?” she asked.

“W-W-What?” he replied, once again totally wrong-footed.

“She won’t let you fuck her?” This was absolutely not the demure woman that he’d known for so many years, and he had to admit that he was shocked, but also aroused. “What? You don’t think your Mom’s old friend should say fuck. Or, God forbid, actually do it?”

“You’re not old M-- Lauren,” he said, catching himself just in time. It earned him a smile.

“You’re very sweet.”

“She says that she’s not ready,” he explained, not sure why exactly.

“Have you ever ... erm...?” she asked, waggling her eyebrows suggestively. He shook his head; too embarrassed to answer. “You know that if she’s saving her hymen for Mister Right, there are other ways...” she said. Oh! My! Fucking! God! Is she talking about anal?! “Personally, I love it,” she added nonchalantly, like she was talking about cheese or something. “Got to be lots of lovely warming up ... and lots of lube ... but a guy’s, or a girl’s, fingers in my ass first ... and then ... hmmmm.”

She looked up at him and burst out laughing. “Your face,” she giggled, pointing at him. He didn’t think he could have been more shocked if the Pope had just gotten his boner out on live TV. “I see that at least part of you likes my depravity,” she said. There, at the end of his now achingly hard cock, was a tell-tale wet patch of precum. “Was it the girls or the anal play?” she asked as she picked up the costume and walked toward him.

“B-B-B-Both,” he admitted.

She once again kneeled down in front of him, placing the costume to one side. “Well, there’s no way we can do a fitting with this thing like this, is there?” she asked, running a finger up and down his shaft, making it jump and twitch. “Would you like for naughty Mrs. Collins to make it go away?”

Oh my fucking God, does she mean what I think she means?! “Yes, please,” he replied, in a voice so tiny as to be almost inaudible.

“You must never tell your mom about any of this,” she said as she slowly peeled his briefs up and over his erection.

For a few seconds, she just stared at him. Then she lightly scratched his balls with the fingernails of her right hand, making his cock twitch like crazy. “Now that,” she said softly, “is a very, very nice cock.” And then he almost fainted as he felt her hot mouth cover his knob, and her shiny red lips caressed the ridge under it.

“Oh, fuck!” he gasped, and felt her giggle around him. Grace had blown him a few times, which he had thought was the best thing ever, but she never seemed to put her heart into it, and she’d occasionally caught him with her teeth. It was clear that Lauren loved it though: humming joyfully as she jerked him off with one hand, caressing his balls with the other, all the time sucking and licking his glans as if it was the most delicious lolly in the world. And she had this amazing technique: the hand on his shaft was moving up and down while also twisting round and round. Needless to say, it wasn’t long before he felt his balls tightening, and he groaned, “I’m gonna cum soon.” Grace had threatened that she’d never, ever go down on him again if he came in her mouth. But Lauren just hummed some more and doubled down on all the gorgeous things she was doing. He held off as long as he could, XXX never wanting it to end, but it was the little finger of the hand playing with his balls, venturing between his butt cheeks to tickle his asshole, that sent him over the edge, and his hips lurched, and his legs shook as he came what felt like bucket-loads into her eagerly sucking mouth.

“Oh God ... Oh God ... Oh God ... he groaned as she gently squeezed his balls and milked every last drop out of his cock, swallowing it all.

“There, that’s better,” she said cheerfully, delicately dabbing at the corners of her mouth as she watched his penis deflate.

She put her hands on his still-trembling thighs and looked up at him. “Are you OK?” she asked.

“Y-Y-Yes,” he croaked, looking back adoringly. “Thank you.”

“Ready to try these on now?” she said, picking up the outfit. He nodded, and then she leaned forward and kissed away a last errant drop of cum from his slit, licking it from her lips with every indication of pleasure. “Good boy.”

He was still shaking faintly as he pulled the clothes on, and his mind was reeling at what had just happened: his mom’s beautiful, previously prim and proper friend had just given him the most incredible blowjob of his entire life. He was definitely in awe, and quite probably already a little in love.

“Not too bad,” she said, examining her work. Then she put a few more pins in, a suspicious number along the inner seams of the shorts, before she told him to take them off again.

This time she did use the machine, and he went and stood next to her, fascinated by the deft and sure way that she worked. It also meant that he could see down her blouse as well, and the way her boobs jiggled was mesmerizing. Of course, the inevitable happened, and his cock gradually began to crank up again.

Every now and again, she’d glance over at it before carrying on. Finally, when he was fully hard again, she sat back and glared up at him. “You know, it’s very hard to concentrate when you’re doing that,” she said accusingly. “I think maybe you’re doing it on purpose.”

“I’m sorry, Lauren,” he replied with a very unsorrowful grin.

“Hmmm,” she said, clearly totally unconvinced. “It’s also making me really fucking wet.”

He tried not to look shocked this time, both at her language and at the image of her pussy, all wet and lovely, that immediately sprang into his mind.

She put her hand under her chin and looked up at him thoughtfully. “If Grace doesn’t want your virginity, do you think that I could have it?”

What can I say to an offer like that? His smile was so wide that his cheeks hurt as he replied, “Yes, please.” It sounded terribly lame, but it was the best he could come up with at the time. She seemed happy enough, though, and reached over and pulled his briefs down to the floor before standing up and kissing him lightly on the lips. Then she wrapped her hand around his cock and used it to lead him to her bedroom.

Leaving him in the middle of the room, he watched in stunned silence as she took all her clothes off. Her boobs sagged just a little as she released them from the bra, but they were spectacularly beautiful and heavy, and clearly very natural; his penis bobbed in appreciation. When she pushed her panties down to her knees, her baby-smooth, bald pussy got a similar accolade. Seeing it, she smiled and stroked her fingers over her vulva.

“Laser hair removal,” she explained.

“Beautiful,” he countered, which earned him a very cute, girly giggle and a big smile.

She lay back on the bed with her legs apart, beckoning him with a finger. Her pussy lips were open a little, and he could see how wet she was inside. It looked gorgeous and so enticing, and the urge to plunge his erection straight into it was huge. But her boobs and her sweet, smiling mouth also seemed irresistible.

 
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