Mom's Best Friend Ch. 01

Joey's mom had always been fussy about him. Sherry would make sure he was in bed for ten every night, even though he was eighteen now, badger him about eating enough greens and try to force him to make friends. That last part was the big struggle. He just wasn't a social guy. He'd had a few friends in high school but hadn't really spoken to them since graduation. Really, he spent most of his time in his bedroom, gaming or sleeping. And, of course, 'relieving stress'. Hot, sticky stress.

Her biggest fear was that he'd go off to college exactly the way he was now. A shut-in with minimal social skills and little drive to work on himself. The boy had never even brought a girl home. She had found dozens of magazines under his bed, or at least she thought they were magazines, of cartoon women with appropriately cartoonish breasts and their tongues lolled out. She was more embarrassed for him than for herself having found them. It was on that day that she resolved to show him that there was much more to life than his bedroom and his own hand. So, she called up her old college friend Eileen.

Eileen was a sex therapist, though she had majored in psychology. She helped men mostly, things like premature ejaculation, erectile disfunction. If a man had a problem with his penis, she figured she had the cure. Sherry supposed it was down to her vast experience. They had been roommates, and there was a sock hung on the doorknob more often than there wasn't in their dorm room. It wasn't a surprise that she got so much attention. Even back then, Eileen had the best body on campus. Full, round breasts that sat tear-drop shaped against her chest, framed by puffy pink nipples in the centre. Below them her slightly plump stomach that jiggled ever so softly. Men seemed to love resting their heads on it, they all called it lovable. Below that she had trained her ass into two firm globes that stretched out the fabric of whatever pants she was wearing, swaying and clapping against each other in stride.

The woman that arrived at the front door on Saturday morning was almost as she had been back then. Her breasts had grown a little larger and a little heavier, the pooch of her stomach had thickened a little more and somehow her ass was rounder and firmer than it had been in college. She wore her light brown hair in a bun that swept back from her temples and had a light dusting of freckles across her cheeks and the bridge of her nose. Upon seeing her old friend, Eileen threw her arms around her. Her breasts flattened against Sherry's own and she couldn't help but notice how warm Eileen felt pressed against her. She wrapped her own arms around her and melted into her embrace.

"Sherry, oh my god! You look so good!"

"Speak for yourself, Eileen! Have you even aged?"

The pair separated and looked each over other with warm smiles and flush cheeks.

"Oh, of course I have. I'm so much bigger than college."

"So much more lovable, remember?"

Eileen giggled and swatted her hand in the air playfully.

Sherry led her to the living room and busied herself with fetching her old friend a drink while she composed herself for the awkward conversation ahead. She imagined Joey up in his room, gaming or... doing something else that required his hands. This was the right thing to do, she assured herself.

"So... you're a uh... sex therapist, right?" She asked although she knew the answer.

"Yep! Thought its really unusual for an eighteen year old boy to have issues with his penis."

"Uhm... no his penis works fine... I mean I think so! I haven't like... looked at it."

Eileen furrowed her brow and turned to face Sherry with her mouth upturned in a slight smirk.

"So what's the problem, Sherry?"

"Uh... he's... well... he's kind of a shut-in... and I found all these... anime girls under his bed and... well... you were always the hottest girl I knew and... maybe you could just... show him how great girls are... so he tries to go out and meet one." She stumbled out shamefully.

Eileen stared blankly at her for a few moments before surrendering and bursting out laughing, her large breasts jiggling about under the fabric of her black sweater with the motion.

"You want me to seduce your son?!" She cackled.

"N-no! I'd never ask you to... if you didn't..."

Eileen held out her palm and composed herself.

"Sherry, honey, I would love to."

Her mouth dropped open and a deep blush snuck across her face. She stammered wordlessly for a few moments, fully expecting Eileen to start laughing again and revealed that she would not, in fact, seduce her son.

"Y-you would..."

"Honey, you don't think I fucked all those guys in college because I don't like having sex, do you? Besides, I always fancied myself a bit of a... virgin killer." She said, her voice dropping into a sultry whisper.

Sherry smiled softly and sank into the sofa besides Eileen.

"Thank you, so much! I know this is a little unorthodox, but I really think this will work. Really light a fire in him, right?"

"One hundred percent. So, tell me all about him."

Twenty minutes later the pair were stood outside his bedroom door, listening to the sound of him snoring. Sherry shook her head and mumbled an apology before rapping on the door harshly. Joey woke in a daze, not registering the knocks on his door until he heard his mom's voice ordering him up. He staggered over and groggily turned the handle, stood in only his burgundy boxer briefs. He was tall and lean with a mop of messy hair and not much else of note about him. He was the kind of person that could stand in a room and not really ever be noticed. And today he was greeted by his mother and the most beautiful woman he had ever seen stood beside her. His eyes darted from her face, down to her heavy breasts to the thick meat of her thighs and then worriedly down to his own underwear, where his cock had begun to stir.

"Mom! You didn't tell me we... wait here!"

"Wait! Sweetie, its fine. Uhm... Eileen is actually here to talk to you about your... stress relief habits..."

His face darkened and his mouth gaped open.

"What?! I don't even... I dont have a... what the hell mom!?"

Eileen stepped forward, her curvy frame taking up most of his doorway and smiled sweetly at him. She was wearing a tight black sweater that was stretched out by the enormous mounds of her breasts, the fabric around them going sheer to reveal the red lace of her bra underneath. Beneath them a short white skirt that stopped just past halfway of her thighs, and even from this angle he could make out the swell of her ass behind her. His cock stiffened to full mast, protruding out from his boxers as if were trying to shake this woman's hand.

"Sweetie. Calm down. Your mom is just worried that... you don't have much interest in... well... I'm sure we'd be better off talking by ourselves right? Just you and me?"

The thought of being alone in his bedroom with this woman was all he needed for his anger and indiginity to give way to dumb lust. He nodded and quickly shooed off his mother, who retreated downstairs with nervous satisfaction.

Eileen looked around his bedroom, at the mess of dishes on his tabletop besides his PlayStation, the overflowing laundry hamper and the bundle of clothes that had not made it in. The acrid smell of sperm that filled the stale air in the room. She walked across to his window and leant forward to open it, her skirt hiking up to reveal the edge of her matching red panties. He locked onto them instantly and let out a strangled groan that she definitely noticed.

"You know, we're wearing the same colour undies.' She said with a smirk.

"I-I didn't... didn't know that." He lied.

"So that tent in your pants isn't for me?"

He went wide eyed and suddenly remembered the situation down there, futiley covering his bulge with his palms. Eileen giggled and sank into the bed, her heavy ass leaving an indent in the mattress. She patted the space beside her and he obeyed quickly.

"So, sweetie, my name's Eileen. I was your mom's bestie in college. We were roommates actually. And your mom is worried about you."

"Why? I'm fine?"

"She thinks you're... missing out on life. Like, girls for example."

He blushes a deep crimson and shifted uncomfortably on the bed.

"I-I've spoken to girls before."

"Honey you're eighteen. Surely you've done more than speak to a girl." She said, unable to hide the teasing lilt in her voice.

"Uh... y-yeah I... I... haven't."

"Never!? Never even kissed a girl?"

She faked surprise, but Sherry had already told her all of this downstairs. Really, she was just enjoying watching this cute little virgin squirm.

"No... I... I prefer like... 2-D girls..."

"Like the ones with giant boobs?"

He blushed deeper.

"How do you know about that?"

"Oh! I forgot to tell you! I'm a sex therapist. I've dealt with pretty much every problem in the book. Lots of men get addicted to that stuff. Hentai, right?"

He nodded shamefully.

"The thing is, sweetie, hentai isn't real. It can't... can't kiss you." She said, turning to face him.

He stared dumbly at her, cock raging in his boxers as his eyes danced between her plump lips and her enormous tits.

"If you don't mind your first kiss being with someone twice your age... I could kiss you right now." She said sultrily.

She parted her lips and slowly pushed her tongue out, licking across them before retreating back in with a wet pop. His cock responded by shooting a thick glob of precum into his boxers, making a visible wet patch against the burgundy fabric. He nodded shakily and leant in towards her, breathing raggedly as she puckered up and leant to meet him.

Their lips met and he was hit by the sweet taste of her cherry lip gloss. He gasped into her mouth as she held him by the back of his head and slipped her tongue into his mouth. Her enormous breasts flattened against his arm as she pulled him in close, a soft heavy weight that felt so natural. His head was spinning and beyond feeling horny he felt so proud of himself. His cock clearly felt proud too, for it was standing at full attention and drooling into his underwear. She pulled away from him with a wet smacking sound, tendrils of drool joining their mouth and then falling away. Eileen took notice of the huge wet spot that bloomed across the front of his boxers and felt her pussy clench around nothing.

"Congratulations on your first kiss." He said sweetly, rubbing his shoulder.

"Th-that was... that was amazing..."

"It only gets better from there sweetie. I've noticed something."

He looked down at his wet underwear and panicked.

"Wh-what did you notice?"

"You keep staring at my boobs!" She giggled and cupped her breasts from underneath, lifting them up and then letting go. They bounced around a little restrained by the cups of her bra.

"Uh... I guess I was... s-sorry..."

"What for? I like it, sweetie. And I guess they're as big as those hentai ones, huh?"

"Y-yeah... but... better..."

She grinned at him and fixed her eyes to his bulge as she hooked her fingers into her sweater, watching as it throbbed and pulsed with each inch of bare skin she revealed. She stopped just below her bra and shimmied from side to side, watching as he drooled all over himself with his mouth slack-jawed. Then she lifted it up and revealed her huge bra-clad tits for him to see in all their glory.

"H-holy shit..." He mumbled.

"You must really like my boobs, cutie pie. Your cock definitely does."

"They're.. they're... c-can I touch them?"

She tapped her chin with her forefinger and tilted her head in exaggerated thought.

"How about a game? Let's see if you can take my bra off all by yourself!" She chirped brightly.

Then she placed her palms flat on the bed behind her and arched her back so that her chest was thrust out in front of him. His mouth went dry as he watched each breast settle into place in their cup. He adjusted his position, and his sensitive cock rubbed against the bedsheets as he did so. An unabashed moan escaped his throat and another spurt of precum escaped his tip and the notion arrived that he might not get through this with clean underwear.

"Good luck!" She chimed.

He wrapped his arms around her torso, his left elbow wedged between the chasm of her cleavage and his right arm pressed firmly against the swell of her breast. She was a lot curvier than him, and his slender frame couldn't get all the way around, so he got off the bed and leant into her, flattening her tits against his chest and leaving his sensitive cock exposed in line with her bellybutton. She looked down at it dreamily as he fumbled about with her strap. Her tits shifted against him, each motion causing his balls to clench harder and his shaft to stiffen further inside his underwear and his body instinctively pushed itself harder against her soft tits.

"I-it won't come of!" He cried frantically, feeling the first tingles of an orgasm blooming behind his balls.

"Oh god! Are my boobs too big?!" She asked in mock exaggeration.

His movement became frantic and jerky, desperate to remove her bra before he filled his boxers up. He couldn't just let go of her and calm down, she'd think he was a total loser. Then, she reached down with one finger and lightly tapped the straining head of his cock through the burgundy fabric. That was all it took. He stiffened up and collapsed forwards arms draped around her neck as his face buried itself in the canyons of her cleavage, inhaling the sweet vanilla smell that permeated from her. His cock lurched forward in his boxers, rubbing hard against the fabric and then pulsed once, twice, and shot out the first rope of cum. He moaned in euphoria into her titflesh as white hot pleasure detonated in his groin, fucking himself against the meat of her thighs as his cock continued to empty itself into his boxers. By the time his orgasm faded he had shot eight ropes out into his undies, a huge wet patch that stained the whole front and leaked out onto both of their thighs and pooled against his sensitive balls. Pleasure quickly gave way to embarrassment and he pulled out of her cleavage and looked her in the eye like a misbehaving puppy.

"Oh sweetie... you couldn't even get my bra off... and you came in your boxers." She said softly, clearly fighting back laughter.

"I'm so sorry... you're just so hot and I was trapped against your boobs... and that kiss really had me worked up... and I wasn't expecting you to..."

She pressed a finger to his lips and shushed him softly.

"Shhh. It's okay. It's actually really flattering, sweetie. My big boobs were just way too much for that virgin penis. Did it feel good, making a mess in your boxers?"

"It felt amazing. The best orgasm ever!"

"See. That's all I wanted. Just for you to feel good. And guess what?"

"What?" He asked nervously.

"Now that you've got one load out... you'll last way longer when I put it between my boobies."

His spent cock somehow found itself twitching back to life in his sodden boxers.

"Now, where's the bathroom sweetie? Let's get you nice and clean."