Author's Note: This is my first story on Literotica. It's about a boy named Elliot, who grows up as the middle child in a trio of male siblings. In this first installment, his friend James convinces him to masturbate together over a picture of Elliot's mother. Elliot, who had never once been aroused at the idea of incest or thought of sex with his mom, is overcome with the strange and overwhelming lust and urges that have suddenly overcome him, and as the seeds that James plants in his mind take root, he is introduced to a whole new perspective on sex.
***
"What? Why?" Elliot blurted out. "That's fucked up, are you crazy?"
"What? Dude, it's a compliment!" James protested. "All I'm saying is that your mom's crazy hot, and...I may have...thought about doing it with her...a couple times."
"Not cool, James," Elliot said crossly. "That's my mother. Show her a little respect."
"Alright, alright, I'm sorry...I...I didn't think it'd upset you that much," James said.
The two 18 year old teenagers were at Elliot's house for school. It was just the two of them, and they were celebrating the end of exams and the beginning of the holidays by playing video games.
Somehow, one way or another, the topic had landed on girls, and James had deeply offended Elliot with his out-of-the-blue comment.
"I'm just saying your mom's really...hot," James said, grinning. "She's not my mother, I'm allowed to think about stuff like that."
"Still..."
"Are you blushing?" James asked.
"N-No! Shut up, man," Elliot said. "Dude, I don't want to talk about this. It's weird."
"What, it's not like I'm asking you to commit incest! I'm just saying your mom's hot! If you want, you can say you think my mom's hot too. I won't get upset."
Elliot had thought James' mom was pretty, but it hadn't led to much more than that. He certainly wasn't about to ask James to sneak him photos of his mom like the latter just had.
"Whatever. I'm NOT going to sneak you photos of my mom so you can...fap to them. That's just...sick!"
"It's not like I'm asking you to join me! It's just...you know...I wanted to try something a little daring, and spanking it while thinking of my friend's mom is just the right amount of risk and daring I'd need," James said cheekily.
"You are so horny," Elliot said. "Go talk to some of the girls in class, man. Leave my mother alone."
James was a footballer and one of the certified 'cool kids' in class. He wasn't 'on-steroids'-type muscular, but he did have a skinny lean body, and thick strong arms and that washboard stomach and abs that girls went crazy for. With his mischievous grin and trademark inappropriate humor, Elliot figured the guy could get girls whenever he wanted to. He figured James had to have had sex by now; 18 year old attractive boy like him would have no trouble finding someone to spend the night with.
Elliot was a different story himself. The two were an unlikely pair. It was the old cliche of two neighbors becoming childhood friends - the cool guy befriending the quiet nerd and shy geek. Elliot hated having to own that title but it was the truth for most of his life. He wasn't the worst-looking guy in the class, he was sure. Freddie Willis took that title with the braces and the acne and the stereotypical stutter that repelled girls like nothing else could. Elliot was no jock, that was for sure, but though he was skinny, he was fit enough, and girls had told him before that he was cute. He'd just never worked up the courage to ask them out yet, and he was sick and tired of guys like his brother Colin telling him to grow a pair of balls and man up.
He'd always grown up with an inferiority complex and suffered from social anxiety; problems that guys like Colin and James - who had girls all over them - would never understand.
The thought of it made him jealous.
"How about I make you a deal?" James said, bringing Elliot back to the present.
"What?" Elliot asked.
"You know my sister Sara?"
"What about her?"
"I know you like her."
"No, I don't!"
"You totally do, dude. You get all hot and bothered everytime she talks to you. She thinks it's cute. I bet she'd give you a chance if I put in a good word-"
"Please don't!" Elliot practically begged. "I'd die of embarrassment."
"Alright...if you get me a picture of your mom in the shower, or at least without clothes on...I'll get you some of Sara."
"That's...sick! You want me to take pictures of my mother...? Naked?"
"I'm not asking you to masturbate over them or anything! Just get me some pictures! I've got the whole holiday ahead of me and I need fap material. The same old porn videos on the net just don't cut it anymore. I want some action closer to home, you know what I mean?"
"I really don't want to know more about what you mean. Fine. Whatever. I'll do it. But just ONE picture. Okay?"
"A deal's a deal, mate. You always got my back, Elliot."
***
Elliot had always seen his mother as...just that. His mother. Nothing else but the woman who had taken care of him for his whole life.
Not once had any sexual thought involving her ever entered his head. But the task set before him, and the seed that James had planted in his head - willingly or not - had taken root in his mind.
He found himself checking his mother out in a new light, for the first time, that night at the dinner table.
The four of them were gathered there to eat. Colin was talking to Dad about some football match - more cliche conversation. Elliot wished his younger brother Matthew - who was turning 18 himself in a month's time - was back from Scout's Camp. He got along well with his younger brother and the two were very much alike. Instead, he was stuck with stupid Colin.
Colin was being a loudmouth again, bragging about something. Colin was no beefcake either, but was fit and athletic where it mattered, like James. As the eldest brother he'd often picked on Elliot for being the skinniest of the three brothers, and had often influenced Matthew to do the same at times.
Being the middle child sucked. Elliot watched his mother from across the table.
"What's the matter, honey?" his Mom asked.
Elliot shrugged, his throat dry. "N-Nothing."
Mom was only in her early forties, at the age of 42. She was still a sprightly radiant woman, always with a smile on her face and a spring in her step. She was what Elliot would call an eternal optimist. His mom worked as a waitress at the local diner on Mondays, Thursdays and Saturdays; and usually spent the rest of her days with her 'girlfriends' - who were all mostly middle-aged housewives tending to their own husbands and children.
Elliot had always seen her as an active and adventurous woman, who had a caring side to her each time he'd been bullied by Colin. He'd never really stopped to look at the ample curves on her body, or the surprising bounciness of her jiggling breasts.
A drop of mayonnaise fell from her spoon and into the curve of her breasts and Elliot watched her wipe it up with finger, licking it off.
He felt his cock grow hard, and grew alarmed.
Shaking himself mentally to clear his thoughts, he looked away hurriedly.
He'd never, ever gotten a weird erection like that before. Sure, like most boys, his erections came and went at the touch of a button. He'd never gotten one from staring at his mother before. It frightened him, the prospect that James' words had gotten to his head, corrupted him.
And the more he thought about it, the more his eyes strayed back to his mother. The more he stared and ogled her, the more he realized James was right.
His mother WAS fucking hot.
She was fucking sexy for her age. The more he stared at her, almost salivating over her body, the more aroused he became.
He could feel his erect cock tenting his shorts underneath the table.
It alarmed him at first. Why the hell was he getting aroused staring at his mother?! It was wrong! It was incest! It was sick and perverted...
...and exciting.
Sitting there at that dinner table, blood rushing to his head and nether regions, for the first time in his life, aroused by his mother, he couldn't remember a time feeling more sexually excited. Not even the girls at school had elicited such a reaction from him.
He'd basically accepted that the girls in his class were out of his league. His mother though...totally accessible at home 24/7.
He turned back to his food but he'd lost all appetite. He was sweating, trying to avoid eye contact with the others. All he wanted to do was get back to his room...and he knew exactly what he wanted to do up there but didn't want to admit, not even to himself.
***
When dinner was over, Colin and Dad went down to watch another dumb action movie. Elliot was pacing back and forth in his room, his phone in one hand.
"I can't do this...take pictures of...no, no, I'll get busted! She'll think I'm sick!" Elliot said to himself.
His erection had eventually subsided but now it was regrowing back to full attention, away from the prying eyes of the rest of his family.
He swallowed, his throat unbearably dry.
"You promised James," Elliot said aloud.
Though to be honest, that wasn't the only reason why he wanted to go through with this.
With the other men preoccupied with the television, Elliot made his way over to his parents' bedroom.
As luck would have it, the door was open a crack. He meant to peek in and knock, hoping that his mother would be asleep or something and he'd take over from there.
What he saw - he was not prepared for.
His mother was standing in front of the mirror, dressed in nothing but a bikini. She had her hands above her head and was checking herself out in the mirror, as if modelling herself.
"No...you look fine..." she was saying.
Elliot's jaw had dropped. She was dressed in lacy skimpy lingerie and his heart was racing. She was talking to someone on the phone.
"Emily, where on Earth did you get the idea that I needed to buy this kind of underwear?" Mom said. "I look like I'm trying to act 23. It's embarrassing."
'Emily' - or Auntie Em, as Elliot had grown up knowing his mother's good friend - said something back over the phone, and Mom laughed.
"David? You think he'd like seeing me in this?" - David was his father's name - "David hasn't touched me in several months, the man's obsessed with work. Honestly, I get more attention from the boys at home than I do from him."
"Hm. I don't blame them. They're young, like we were. Their raging hormones control their actions and all that nonsense, you know. I'm the only woman in the house with three horny males. Yeah, that's right, Matthew's still at camp, he's coming back next week."
"Oh, please I don't want to talk about David and my sex life. David only cares for his stupid television and spending all his time on Boys' Night. His friends are nice but he spends all his time with them, hanging out. I barely get any when he's actually home."
"Oh, Em, you're so racy tonight, haha. A threesome? You're crazy! I might have taken three dicks at once when I was still in college, but I'm a mother of three now! ...Wait that came out wrong. Oh, don't you dare suggest that! Emily!"
Mom continued laughing, still staring at herself self-consciously in the mirror.
"Thanks for buying this for me as a gift though...it feels weird modelling it. I'm not runway model for sure but it looks nice. Reminds me of the good old days. Whatever. Alright. Bye."
She hung up, and continued checking herself out, adjusting her bra strap, fidgeting, etcetera. Elliot could feel his cock standing to full attention, pressing against his shorts, about to break free and give his mother a salute.
He swallowed, his balls aching. He wanted nothing more than to masturbate, but he fought down the urge. He had good self-control, good willpower, all that nonsense.
Raising his phone, he snapped a picture with his camera. Then another. And another. And another, and another, and another...
***
"I'm sorry I didn't get any pictures of Sara," James said the next day.
The two of them were back in Elliot's room. Elliot had had a hard time in class earlier that day. He'd fought down the will to masturbate all of last night, only to wake up after a vividly detailed wet dream, where he'd groped, fondled and brutally ploughed a woman dressed in the same lacy bikini his mother had been modelling.
Even after cleaning up the sticky semen-stained mattress, his dick was all recharged and ready to go almost instantly and he'd gone through most of school with it tenting up in his pants.
At one point, some girl named Jennifer caught sight of it and she'd giggled so hard. He'd been so embarrassed and couldn't say anything. Jennifer had been decent enough not to point it out though, even when her friends asked her what she was laughing at. He was grateful that she hadn't made a fool of him; perhaps he should thank her later.
"You promised me!" Elliot whined. "Do you know what I had to go through to get these pictures of my mother-"
"Shh! Bro, isn't Colin in the next room? Keep your voice down!" James said.
Colin was indeed in the next room. The three boys were the only ones in the house.
"I just...I..." Elliot felt incredibly frustrated, both with his own sexual confusion and James.
"Hey, I'm sorry, Sara was away last night, I couldn't get you any pictures. And, I may be dirty minded but I'm not going to steal some of her panties for you or anything...she organizes her underwear as if they're top-secret government plans. She'd notice if even one was missing and report it straight to MY mom! Then I'd look like a pervert getting YOU something to fap to, you desperate horny boy." James grinned.
"I'm not desperate or horny! I just...I thought...I...I got these pictures for you and you didn't hold up your end of the bargain!" Elliot said.
"Well, I'll repay the favor later. Thanks for the pictures. I know it seems a little sick but...it's just between friends, you know? Boys will be boys and all that crap. I'm sorry you don't get anything juicy to masturbate to while I do."
Elliot groaned. "I...I..."
"Dude, you really are horny today, aren't you?" James laughed. "You look really pissed off. Dude, okay, I'm sorry I didn't get you anything from Sara."
"Whatever. Here. I took these pictures of Mom the other night."
James' eyes went wide. "U-Uh...wow. I mean, come on...you look at this yourself. You're a boy like me, you can't deny these are fucking hot. Your mom is sexy as fuck."
"She looks just as hot as yours, but you don't say stuff about your mom!" Elliot said.
"Well, yeah. I'm just saying I feel more comfortable talking about your mother. I know you're into girls, dude. I saw your erection when you were checking out Jennifer and Brianna and-"
"James!"
"It's true! I know that no matter how shy you act, you're as straight as they get. Look at these pictures and tell me you're not even a little bit aroused, even if it's your mother. Go on. Look! That's a sight to get any boy hard and ready for action."
Elliot swallowed. He'd snapped almost two dozen pictures of his mother in that bikini. Her ample breasts and almost visible pussy was a huge turn-on. He tried to hide his own erection from James, turning away from him on the bed so he couldn't see his cock tenting his shorts, but James saw him moving away and grabbed his arm.
"You are aroused! You've got a hard-on!"
"Shut up!" Elliot pushed James. "I do not! Colin's here, be quiet!"
"Colin wouldn't give a fuck, relax! Dude, you agree! Admit it, your mother is hot as fuck."
"Okay, yeah...whatever. She is pretty good looking."
"Good looking? She's so sexy...I would give anything to fuck-"
"James."
"Sorry. You know what I mean."
James licked his lips. "I'm going home to...you know. Masturbate. You comfortable with me saying that?"
Elliot shrugged. "I'm not that innocent, you know. Yeah, we both know what you're gonna do once you get home."
James got up to leave, then stopped. He turned back to Elliot. "Dude, why don't you join me?"
"Excuse me?" Elliot asked.
"Come on! I saw your dick! You know you want her."
"What the fuck, bro! That's my mother!"
"She's also a sexy woman! What's your point?" James said, grinning.
"I'm not masturbating to my own mother!"
"Just...ignore her face. Look at her body, her breasts. Shoot your load. Come on. I can tell from your face that you really want to. You look as horny as I am."
Elliot hesitated. There was a strange feeling in the air, like he was about to cross a line here with what decision he made.
"Come on! How often in your life are you going to get a chance like this? I don't care, I'm going to masturbate right now. You don't have to watch if you don't want to but I really need to stroke my cock because your mother is smoking hot-"
"Alright."
"What's that?"
"Alright. Fine. I'll do it."
"For real?" James looked stunned.
Elliot shrugged. "Peer pressure, right? I'm not into incest, I swear...I...I just...I'm really horny right now."
"Course you are mate. I can tell. If you don't get off with me right now you'd probably climb all over her when she gets back and be unable to control yourself-"
"Just...shush. Let's just...get it done and over with."
"Give in to your urges, man." James laughed. "It's just masturbating, I'm not asking you to do anything else. It's not incest if it's using your hand, hahaha. Oh man, that's a good quote. I need to write that down or something."
James unzipped his jeans, stripping his shirt off. Elliot had seen James without his shirt on a couple times but never really made much notice. James was tan, with lean skinny arms and that good ole' washboard stomach and abs he'd seen whenever the two boys went out swimming in James' pool. Elliot had never really cared much, not when he'd been staring at Sara sunbathing in her bikini and trying to hide his own erection from James in the pool while the latter teased and threatened to tell on him.
Elliot watched as James stripped off his jeans and shorts. James' hard cock sprang free of his boxers, standing up straight to full attention. His balls and scrotum hung heavy and full, with a tuft of brown pubic hair around his throbbing veiny shaft. He grabbed his dick and turned to look at the picture on Elliot's phone, zoomed in to his Mom's face and breasts. "Come on. Don't leave me naked on my own. Take your clothes off, let's take a fap."
Elliot slowly raised his arms and slipped his shirt off. James laughed, looking at Elliot's bony frame, but not unkindly. "You know, I'm sure the girls wouldn't mind going for a skinnier guy. I'm sure the beefcakes and their boisterous attitudes get annoying at times. If you were a little more confident, you could get some pussy on the side."
Elliot was too shy to say anything, but he laughed anyway, starting to loosen up. He took his pants off, and slowly and self-consciously let his erection free, quivering and twitching in the cold air. His dick wasn't as thick as James' was, but it was longer by a couple millimeters.
James glanced at him and nodded. "So...you are a dude."
"Very funny. This is so weird...fucked up."
"You're aroused. Don't deny it. This is making up for Sara. Relax, let it go."
"I can't believe I'm about to masturbate to my own mother."
"It's not incest-"
"-if you use your hand, yeah, whatever. I still think this is weird."
"Let's see if your tune changes once your hand's coated in cum and sperm."
James grabbed his dick and began to stroke furiously, already groaning and sweating, eyes fixated on the picture of Elliot's mother and her breasts.
Elliot was breathing heavily. He touched his dick and began to stroke it. Moving his hand back and forth, the feeling of masturbating was heavenly.