Story By: B.C. Kingston
Artwork by: B.C. Kingston
Mandy closed her laptop and leaned back against her chair. She was spent, physically and emotionally. As she looked at the trail of wetness on the towel between her legs and down onto the carpet, her sense of physical satisfaction quickly gave way to pangs of guilt.
What had she done? She’d sent naked pictures of her own daughter to a stranger on the internet. Worse, she masturbated to them. Even worse than that, she enjoyed the hell out of it. What was wrong with her?
It was only a few short months ago that Mandy was going through the motions of being a happily married, middle class, and very boring wife. Her daughter Lilly was mostly out of the house now attending the local university and doing God knows what else in her free time. Although she technically still lived at home, Mandy rarely saw her.
With Lilly gone, Mandy was left to focus on working and spending time with her husband, Charles. However, spending time together had to be a mutual thing and Charles seemed to prefer work. Her husband hadn’t even noticed when Mandy cut back her off-season hours at the tax-accounting firm. She was home a lot more, but that only made clear how little time he spent at home. If he wasn’t traveling to an industry convention somewhere, he was burning the midnight oil doing paperwork at the office. And when he was home, there was the constant interruption of sales calls which he rarely deferred despite Mandy shooting dagger stares at him.
Charles’ work brought them success though. She had a nice big empty house to wander around in. Lilly didn’t have to take out a student loan. The cars in the garage were both Audis. Mandy couldn’t really complain about her situation in life except she was bored, miserably bored.
Her sex life was practically non-existent. When Charles did oblige her, it was a very clinical thing; not much satisfaction to be derived from that. Worse, it was very evident much to her dismay, that Lilly’s sex life had kicked into overdrive. There were so many boys around in high school and now college that Mandy couldn’t keep track, and had long since given up trying. Lilly’s soap-opera romances were convoluted dramas that she tried her best to avoid getting tied up in.
The frustrating part was Mandy saw a lot of herself in Lilly, at least physically. When she was Lilly’s age, Mandy would’ve been her spitting image: medium height, bright red hair, pale freckled skin, voluptuous, and curvy. The years had taken their toll, of course. A little extra weight, a little sag, some gray hair, and creaking in her joints. However, at a distance, one would be hard-pressed to tell them apart. Lilly’s personality on the other hand, came almost exclusively from her father: outgoing, energetic, impulsive, and unflinchingly optimistic. Lilly seemed to dance through life, unfazed by her circumstances, despite all of the questionable decisions she’s made, particularly in the romance department.
Still, Mandy had to admit she was jealous of her daughter. If she could relive her own youth, she would want what Lilly had. She wouldn’t have been so shy and bookish. She would’ve lived it up a bit more. And given her current circumstances, she would’ve had a lot more wild and carefree sex. She feared the consequences before, but what had she got to show for it now?
That’s why Mandy was so upset when she found those pictures on her daughter’s laptop. As a mom, she was horrified that her daughter would do such things, posing naked like that for who knows which boyfriend, and on Mandy’s own bed too. It was so… slutty and disrespectful. She thought she had raised her daughter better than that.
Yet at the same time, those pictures were the embodiment of everything she wished she had done in her own youth. On full display was the outgoing, sexy, and fun persona of “Lilly,” the girl she never was.
Mandy thought about confronting her daughter, but quickly dismissed it. How would she justify snooping in Lilly’s private files? Furthermore, Lilly was an adult and as distasteful as it was, she was well within her rights to keep naked photos of herself if she wanted. Why she felt the need to do that in her Mom’s bedroom was hurtful, but in an odd way she understood that too. The taboo of being so naughty on her parent’s bed must’ve been quite the turn-on.
So instead, Mandy plugged a her thumb drive into Lilly’s laptop and copied the pictures. She wasn’t sure why she did it. Perhaps leverage for some future argument? Blackmail? No. She knew why she wanted those files, even if she couldn’t admit it yet. She wanted to reclaim her youth, take back some of the carefree sexuality she had missed out on over two decades ago.
Several weeks passed by and Mandy found herself thinking about those pictures more than she liked. She was obsessed really, jealous, depressed, and yeah… horny. She couldn’t take it out on her daughter though. That didn’t seem remotely fair. So instead, she decided to take on her daughter, to become her.
She thought about dressing sexy and heading to a singles club while Charles was out of town, but nixed that idea immediately. She didn’t want to cheat on Charles (at least, not physically) and she certainly didn’t want to be that sad fortysomething woman dressed half her age hanging out with drunkards in a smoky bar. Besides, the fear of getting into trouble or worse, getting caught terrified her.
No, she needed an option she could have more control over; something that allowed her to roleplay a younger, sexier version of herself and maintain her anonymity. Once the parameters were set, the solution was pretty obvious. “Lilly” would live out her fantasies on the internet.
Personals were out. She didn’t want to meet anyone in person, or do phone calls. So she settled on several romance chat rooms she found in search. She made a profile that was an idealized sexy version of her younger self. Mandy used a candid picture of her daughter, which she cropped above the lips to obscure her face.
And then the perverts came streaming out of the woodwork. At first, it felt somewhat gratifying, but got disgusting quickly. Mandy learned fast though. She blocked often and quickly. A few men she met online seemed alright and she flirted a bit, but she was still having trouble coming out of her shell and roleplaying a confident, sexy young girl, especially when so many men wanted to dominate her in some way or another.
Then Jonathan messaged her. He seemed different right from the start. He was shy, sweet, smart, and very inexperienced. He was like a lost puppy. Mandy’s own insecurities vanished as she quickly swept him up into her fantasy. Talking to him was easy, and the persona of LillyPad4_69 flowed effortlessly from her fingertips.
He sent her pictures from vacation. He was cute, handsome even - just the type of guy she could envision “Lilly” falling for. Their rapport transitioned comfortably from talking about mundane subjects like school and favorite movies into fantasies and turn-ons. He was an eager and willing participant in her fantasies. The thought of her words driving him to masturbate was greatly satisfying. She could tell he was infatuated.
Mandy’s time with Jonathan had a rejuvenating effect on her. Not only did she feel sexier and have incredible orgasms, but there was a spring in her step outside of the chat room. She even started utilizing her long dormant gym membership and eating better. Her whole outlook on life was subtly shifting and she found herself not just pretending to be Lilly online, but embodying that persona in real life. She bought sexier clothes, wore skimpy underwear, and invested in new makeup and skincare products.
Lilly was the first to notice, of course. She came by the house one afternoon and stopped in the doorway and stared at Mandy, gobsmacked.
“Wow Mom, you look great! Have you been working out? Where did you get that outfit? I love it!” she rattled off in her typical stream of consciousness fashion. They went shopping. Mandy had more fun hanging out with her daughter than she’d had in a long time. If only Lilly knew what was behind her sudden transformation…
Mandy was really enjoying her time with Jonathan, but knew her house of cards had to come tumbling down at some point. He wanted more than she could give him: photos, phone calls, her last name, and a number of other personal details she couldn’t part with. Her thoughts turned once again to Lilly’s naughty photos. She still had them. Jonathan would love them. But could she do it? Could she trust him with them?
She decided she could. After all, Jonathan had more than earned that much for what he had unknowingly done to boost her own self-confidence. However, a little insurance policy was in order. And so she devised a “homework” assignment for him. If he wanted naughty pics of her, he would have to send some naughty pics of his own first.
Naturally, he agreed immediately. Mandy knew Jonathan was in lust with “Lilly” but she didn’t quite realize the lengths he would go to in order to please her. When she opened that email from him, her mind was blown.
Quickly setting her wine down on the nightstand, Mandy settled comfortably into the pillows of the bed with her laptop to the side and began slowly scrolling through Jonny’s lust-letter.
“I’m so excited to see you, my cock is already hard in my pants.”
“Oh yes it is mister,” Mandy cooed at her laptop. She was ready to go too. She’d already stripped down to her underwear and put a towel underneath her on the bed. Her free hand started squeezing her ample breast through her new lacy white bra.
“I wish it was you unzipping my fly. Wouldn’t you like to see what’s inside?”
“Mmm hmmm…” Mandy felt a shiver travel down her spine. Jonathan had done this for her and only her. Being the sole audience for this special show made it that much more scintillating. Mandy dug into her bra and freed her fleshy pale, freckled tit. She began rubbing and pinching her swollen pink nipple.
“I’m already wet for you. Just look at the precum dripping from my tip.”
Mandy was wet too. Jonathan’s cockhead was shiny and glistening with precum. She wanted to lick the screen. She wanted to taste him. Instead, she settled for sliding her hand down her tummy and into her panties. Now they were both fondling their sex through their underwear.
“I can’t help but touch myself when I think of you. Do you like having this power over me?”
‘Oh yes I do Jonny. You have no idea how incredible it feels to have you lust after me.’ Now his cock was completely free of his underwear, oozing precum down onto his sexy happy trail. Mandy followed suit by frantically rolling her panties down her legs just far enough to spread them apart. She started running two fingers the full length of her sex, gathering up her juices and rubbing back up to circle her clit.
“I’m imagining you straddling my hips, your wet pussy leaking onto my balls as you stroke my shaft.”
The next shot was nothing but cock. It took up the full frame in all of its wet, veiny glory. Mandy had to pause and savor this picture, her mouth slightly agape, a bit of drool quivering at the edge. Maybe it was just the pure sensual bliss of the moment, but Mandy was certain she’d never seen anything so magnificent before in her life.
‘Oh, I can do that for you baby!’ She pushed her laptop further down on the bed and folded the screen back so she could look down on it. She got on her knees and spread them apart, panties still wrapped around her calves behind her. Sitting upright, she stared down at the image of Jonathan’s rigid member, and started frigging herself deep with two fingers.
A moan escaped her lips, “Mmmm… Jonny.” She reached over and scrolled to the next picture.
“Oh god I want to be inside you so badly. How much do you want my cock in your pussy? Can you imagine how good it would feel?”
Jonny was gripping his hard shaft tightly. It looked swollen and ready to burst. Mandy’s hand was moving so quickly, it made wet spanking noises as she slapped her pussy. Her juices were running down her thighs now. She alternated between finger fucking herself, and madly rubbing her sopping wet clit.
Close to the edge of orgasm, Mandy saw a part of one more picture at the bottom of her screen. Carefully, she leaned over her quivering legs and scrolled it into view.
“Mmmm… I’m cuming again for you Lillypad. Look at the mess I made dreaming of your sexy body!”
There it was. Cum all over his belly, dripping from his cock, soaking into the patch of pubis. Mandy lost it. Falling back onto the bed, she arched her hips into the air, furiously rubbing herself.
‘Oh God Jonathan! Oh God, oh god, oh god….’
“MMmmmmm….. “ Another deep moan emanated from within as her climax washed over her. She bucked her hips in time with the waves of pleasure, her hand now clamped down on her pulsating sex.
As the waves subsided, her legs gave out and she collapsed fully onto the bed, absentmindedly kicking the laptop with the heel of her right foot.
“I hope you loved these pictures. I definitely enjoyed making them for you. I can’t wait for you to show me how they made you feel…”
‘Oh Jonathan… If you only knew...’ A small pang of guilt bullied its way into her mind as the euphoria of her orgasm slowly faded…