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Whoever said the best jokes were the ones based in reality was so right. The jokes about Ian being a virgin was one that unfortunately was based in reality. No one knew it but him, and the women he’d dated in the past, but his coworkers and the internet poked fun constantly. Ian rolled with it, laughed, and was overall a good sport. However, everytime the joke was made, he’d feel shame in his gut. Being a virgin this late in life was usually a religious based decision, but for Ian it wasn’t.
It wasn’t that Ian didn’t want to have sex, or that he was waiting for marriage or even waiting for “the right woman.” What it had come down to was that it just never worked out. Ian’s past girlfriends had always had some sort of hang up. Some were waiting for marriage, one was a survivor of abuse and couldn’t have sex without having flashbacks, and one didn’t want to because she was terrified at the idea of being the person to take Ian’s virginity.
Ian didn’t have some impossible standards for losing his virginity. At least, he didn’t think they weren’t unreasonable standards. He wanted the sex to be with someone he cared for and trusted, it couldn’t be a stranger because he wouldn’t have the trust. He didn’t want to get attached to some stranger just because they took Ian’s virginity. It didn’t need to happen with a girlfriend, but he thought it was the most likely situation that would happen.
The virginity joke wasn’t the only one that was too true. Ian had made jokes that had hinted at something that he had hoped no one had picked up on. He thought he was getting away with it too, until one afternoon when it was just him and Amanda in the kitchen of the office.
“So, have you found anyone to indulge your little mommy kink?” She asked, her tone light and teasing.
All of the color drained out of his face.
“Wha-how did you figure it out?” Ian demanded in a whisper.
Amanda blinked in surprise. “That’s a real thing for you? I thought it was just a joke.”
Ian wanted to bolt. He could see the exit just behind her. It was calling to him, a siren song, promising freedom and relief from his humiliation. He was about to make a break for it when Amanda placed a gentle hand on his shoulder.
“Hey, I don’t care, Ian. It doesn’t matter to me if it’s a joke or real. You aren’t hurting anyone by enjoying what you enjoy.” Amanda said in a kind but firm tone.
Ian looked into her eyes. She was giving him a firm look that reminded him of one he’d seen mothers give children for years. The reassuring kind for hard situations. Ian swallowed thickly.
“Thank you.” Ian whispered.
She took her hand off his shoulder and walked away.
Ian wasn’t sure when he’d started to notice Amanda as more than a co-worker and friend, but he knew it happened after that conversation. He started to notice how pretty she was, how toned and inviting her body looked, and how she always seemed to fall into maternal roles so naturally. It was like she was doing it all just to mess with him, but he knew she wasn’t. She hadn’t brought up his kink since she found out it wasn’t a joke. However, more than once while he was checking Amanda out, he saw her look back.
The day everything changed, there was a knock on his office door. He didn’t look up from his work.
“Come in.” Ian called.
Amanda walked into his office. He probably wouldn’t have thought anything of it if she hadn’t closed the door behind her and locked it. The moment he heard the click of the lock, Ian abandoned his work.
“Is everything okay?” Ian asked.
Amanda strutted over to his desk, hips swaying in such an enticing way. She crossed over to his side of the desk and sat on his desk. Ian’s mouth suddenly became dry.
“I’ve noticed you watching me, Ian.” She said.
Apologizes spewed from his lips before his brain even caught up to what was happening.
“I’m so sorry. I’ll stop. I’ll leave you alone and never bother you again. I’m so sor-“ Amanda cut him off.
“I’m not upset.”
“You’re not?” Ian asked.
“No, I’m not. In fact, I think the two of us could have a lot of fun together. What are you doing after work?” She asked, a little smirk on her lips.
Ian’s heart was pounding in his chest. “I’m not doing anything after work.”
“Good. Come to my apartment after.” She said, and stood.
“Wait, there’s something you need to know!” Ian blurted out.
Amanda looked at him.
“I-I’m a virgin.” Ian’s cheeks were on fire.
The smile that took over Amanda’s face was soft and kind. “That’s okay, baby boy. Mommy can take care of that, if you want her to.”
Oh fuck.
Ian swallowed thickly. “I’d like that.”
She leaned down and kissed him softly on the lips. Before he could kiss back she was pulling away, leaving behind only the memory of her lips and the scent of her perfume. As quickly as she’d come into his office, she left it.
He couldn’t get any work done for the rest of the day. How could he when Amanda had all but told him she was going to have sex with him after work. He tried to make himself focus but inevitably his thoughts would shift back to Amanda. He tried to make a beeline for the parking lot once the working day was over, but Anthony held him up. Ian usually loved any excuse to talk to his best friend, but he was antsy to leave and get to Amanda’s.
“What’s got you all worked up?” Anthony asked.
“I’ve got a date.” Ian said.
It was kind of a lie, kind of the truth. He wasn’t sure going over to Amanda’s to have sex counted as a date, but it wasn’t nothing.
“Oh! Why didn’t you tell me earlier, man? I didn’t mean to hold you up. Have fun tonight.” Anthony said, clapping him on the shoulder.
“I will.” Ian said with a smile.
He drove to Amanda’s apartment with nervous jitters. What was going to happen? Were they just gonna bang and never talk about it again? Would they become friends with benefits? He had no idea what would happen.
When he knocked on her door, Amanda opened it with a smile.
“Hi.” Ian said awkwardly.
“Hey Ian. Come on in.” She said, opening the door wider.
Ian had been to Amanda’s place before. It was a cozy apartment, covered in plants and little touches that made him feel right at home. She led him to the kitchen.
“Would you like some tea?” She asked, getting out a tea bag and a kettle.
“Sure.” Ian said.
They made small talk and passed jokes back and forth as they waited for the water to heat up. He relaxed easily. Talking with and being with Amanda felt so natural. She poured him his tea and they drank it slowly.
“So, you’ve got a mommy kink.” Amanda said casually.
Ian’s cheeks heated up. “We already established that.”
“I know, but it’s good to make sure we’re on the same page. Do you want to explore this kink?” She asked.
Ian looked down at his mug. “Yeah.”
“We could do that, baby boy.” She reached out to cup his cheek.
Ian leaned into her touch.
“I don’t know what I’m doing.” Ian admitted. “Like I said, I’m a virgin.”
“How did a handsome guy like you stay a virgin for so long?” Amanda asked.
So he told her, blushing and stammering the whole time. Amanda didn’t interrupt or comment, just let him talk. Once he was done, he looked at the floor. He felt fingers on his chin, tilting his head up, making him look at Amanda.
“You have nothing to be ashamed of Ian.” Amanda said in a kind voice. “Wanting to lose your virginity to someone you trust is valid.”
“Thanks.” Ian said sheepishly.
“We don’t have to do anything tonight if you don’t want to.” She said.
“I do!” Ian blurted out. “I want to! I-I really want to.”
His cheeks were burning, but he didn’t look away from her gaze. Somehow he knew that Amanda would take care of him. He knew he could trust her. She smiled, something so bright and beautiful.
“Okay, do you want the mommy kink incorporated as well?” Amanda asked.
Ian nodded. “Please.”
“I can do that, baby boy.”
Ian shivered and Amanda smirked.
“Let’s take this to the couch.” She said and he followed her into the living room, both of them abandoning their cups of tea.
She sat down on the couch and Ian sat next to her. He fidgeted nervously. He wasn’t completely inexperienced. He’d done some things. He’d fingered girls before, had gotten handjobs in the past, but nothing further than that. He waited for Amanda to make the first move, not sure he’d know where to start if it was up to him.
She turned towards him and he copied her.
“Relax, baby. Everything is going to be fine. You can tell me to stop at any time.” Amanda tells him with a gentle smile.
Ian relaxes a little, his shoulders sagging. He smiles back softly, and then she’s leaning in. He follows her lead, and then they’re kissing. It starts slow, gentle, and soft. She cradles the back of his head and he wraps his arms around her as the kiss deepens. It’s nice, kissing Amanda. She’s a good kisser. She’s in control of the kiss and Ian is happy to let her. It feels nice to sit back and let someone else take control.
Then her hands began to wander. They left his head and explored his arms, his chest, sliding down to his belly. He moaned into the kiss when her hand found his clothed dick and squeezed gently. She pulled away from the kiss with a smirk.
“Want something?” She asked.
“You know I do.” Ian said.
Her hand withdrew and he whined.
“I’m not touching you unless you tell me what you want.” Amanda says.
Ian bit his bottom lip. It was so embarrassing.
“It’s okay, Ian. You can tell Mommy what you want.” Amanda encouraged him.
Ian couldn’t help the groan that tore from his throat. The pleased look in her eyes made him feel warm in his chest. He wanted to please her, he wanted to make her happy and feel good.
“Please touch my dick, Mommy.” Ian didn’t even remember deciding to say it, the words just escaped before he could stop himself.
Amanda smiled sweetly at him. “Good boy. Take your clothes off for Mommy.”
He couldn’t shed his clothes fast enough. He stood in front of her, naked as the day he was born, and realized Amanda was still in her dress. He blushed, a little embarrassed to be the only one naked, but was surprised that it went straight to his cock. He was slowly chubbing up from the situation and he was mortified that she had done so little, yet he was already responding.
“Well, aren't you handsome.” Amanda purred, her eyes darkening as she looked him up and down.
Ian’s cheeks heated up. He shifted his weight from foot to foot, not knowing what to do.
“What do you want me to do?” Ian asked.
Amanda stood up, towering over him. “Lay on your back on the couch for me, sweet boy.”
Ian followed her instructions, eyes glued to Amanda. He waited for further instruction. She didn’t speak though, she grabbed the hem of her dress and pulled it over her head. His breath caught in his throat. Amanda must have been planning this when she came into work today because she was wearing a lacy white bra and a matching pair of panties. The white lingerie looked amazing against her tan skin, and she must have known how gorgeous she looked in her lingerie because she held herself with a confidence that only came from knowing you’re attractive and loving yourself.
“See something you like?” Amanda teased, a playful glint in her eyes.
“Yes, Mommy. You’re beautiful.” Ian told her.
Amanda smiled sweetly. “Thank you, baby.”
She perched herself on the arm of the couch and spread her legs. She pushed her panties to the side, revealing her glistening pussy to Ian. He groaned. She was gorgeous everywhere. Her pubes were neatly trimmed, her clit was prominent, standing proudly and Ian wanted to lick it.
“Can I taste, Mommy?” He asked.
“Maybe after.” She said nonchalantly.
Ian whimpered, imagining licking his own cum out of Amanda and his cock twitched. They hadn’t discussed using protection or not. Of course he’d use a condom if that’s what she wanted, but he couldn’t say he didn’t ache to know what her bare cunt felt like wrapped around his dick. He opened his mouth to speak again but he snapped his mouth shut as she slid a finger into her pussy. Amanda moaned softly as she began fucking herself with her finger.
“Hmmm, bet you wish it was your finger in Mommy’s pussy.” Amanda said with a smirk.
Ian nodded, watching intently. His cock was fully hard now and he was breathing heavier as he watched Amanda slowly finger herself. After a few minutes, she added a second finger and began scissoring herself open. Amanda crooked her fingers and moaned.
Ian whined. He wanted to touch her and be inside her. He wanted her so badly, his hands itched.
“Mommy, please!” Ian begged.
“Be patient, baby.” Amanda told him.
“I’m trying, Mommy, but I want you so badly.” Ian whined, wriggling impatiently on the couch.
“Be a good boy and I’ll let you cum tonight.” Amanda said.
Ian’s jaw snapped shut. He wasn’t going to talk himself out of cumming tonight. Amanda smiled at him.
“That’s a good boy.” She cooed.
He shivered. He liked that. A lot.
He wanted to be a good boy. He wanted to be her good boy. He wanted to please her and make her feel good.
Amanda continued to finger herself for a while and once she deemed herself ready, she pulled her fingers out, took off her panties, and straddled Ian’s waist. Amanda lined herself up and smiled down at Ian.
“Are you ready, baby?” She asked.
“I’m so ready, Mommy. I want you so badly.” Ian said breathlessly.
“Yeah? You want Mommy’s pussy?” Amanda cooed.
Ian was nearly drooling at the prospect when logic screamed in the back of his mind.
“What about protection, Mommy?” Ian asked.
“I’m on the pill and I’m negative for everything. You don’t have to worry.” She assured him, a fond look in her brown eyes. “We can get a condom if you want though.”
Ian shook his head. “That’s okay, Mommy.”
He must have spoken too quickly, because she smirked.
“You want Mommy’s bare pussy? You want to feel her hot, wet cunt on your dick, baby boy?” Amanda asked.
Ian nods frantically. “Fuck yes, Mommy. I want your pussy so badly. I wanna be inside you so badly. I’d give anything.”
Amanda smirked and slid down onto his dick. Ian moaned loudly as she slowly went down. She was warm and perfect on the inside. She slowly slid down onto him until he bottomed out. Amanda grinned down at him as Ian whimpered.
“You like Mommy’s pussy, baby?” Amanda asked.
“Your pussy is perfect, Mommy. I’ve never felt anything better. Oh my god! Holy shit, please move! Please, please, please!”
Amanda braced her hands on Ian’s chest and began riding him. She’d never looked so perfect. Even with the bra, her breasts jiggled, and her face twisted up in pleasure. She looked almost ethereal and Ian was at her mercy, a worshiper at the altar that was Amanda. He wanted to kiss, lick, and touch every inch of her skin. He wanted to map out every dimple, every stretch mark, every freckle. He wanted to know her like he knew the back of his hand.
“Mommy, can I please touch you? Please?” Ian begged.
Amanda looked at his face. “Where do you want to touch Mommy?”
“Your hips? Your tits? I don’t care, Mommy. I just want to touch you. Anywhere, please.” Ian whined.
Amanda smiled. “You can touch Mommy, baby boy, anywhere you want.”
His hands went to her hips first. He felt as she bounced on her cock in everyway. Felt her cunt hugging his dick, felt the ripples in her flesh as she moved. Ian understood why people never shut up about sex. What could be better than this? The warm feeling of a woman on him, her warmth wrapped around his dick, the space she offered him to be vulnerable, the safety she offered.
He sank into the pleasure, groaning and moaning as she rode him, his hands slowly moving up her body. They trailed up her soft belly to her large breasts. Ian looked at her face, wanting confirmation once again that it was okay to touch them. Amanda’s eyes were closed when he first looked. It took a moment for her to open her eyes again and see him looking at her.
“Mommy, can I touch your boobs?” Ian asked.
He was surprised by how small his voice sounded, how fragile and vulnerable his voice was even to his own ears. How did he sound to her?
Amanda stilled and Ian whined high in his throat.
“Be patient.” Amanda chided.
Ian looked down shamefully. “I’m sorry, Mommy.”
He looked back up just in time to see her arms behind her back and her bra fall loose. She shrugged it off, leaving her tits bare for him to see. Ian licked his lips as he tried to will the image of her perfect breasts into his memory forever. He never wanted to forget her tan skin, her hard, pink nipples.
“You can touch them now.” Amanda said, and began grinding down against him.
It must have felt good for her because she moaned softly and a thrill shot through Ian. All he wanted was to please her. He wanted to be a good boy for Mommy.
“Does it feel good, Mommy?” He asked as he hesitantly reached a hand to her breast.
“Yes, baby, it does.” Amanda sighed.
“Good. I-I want to be a good boy. A good little toy for you.” Ian admitted.
The look in Amanda’s eyes could only be described as adoring. She looked at Ian like he was something precious, something to be cared for. Not like he was a mid-thirties fuck up.
“You are, Ian. You are a very good boy for Mommy.” She told him seriously.
Then, she grabbed his hand that was kind of hovering over her breast and placed it on her tit.
“Go ahead, play with it. Mommy’s nipples are sensitive. Touch them, play with them, suck on them.”
He leaned forward, capturing the nipple of the breast he wasn’t touching in his mouth as he began to knead the other breast. He sucked the nipple gently at first, flicking his tongue over the bud. Amanda’s moans grew. He began pinching the nipple that wasn’t between his lips as the fire in his belly burned brighter, her walls clenching down around him.
Everything was so overwhelming. What should he focus on? How could he pick when each thing was so special and out of this world in it’s own way?
“I can feel your cock twitching in me. Are you close, baby boy? Are you going to cum inside Mommy?” Amanda asked.
Ian groaned around her nipple and nodded.
“Good boy. Make a big mess, and then you’re going to use your tongue to clean it up.”
He whined and sucked harder on her nipple. Fuck, he wanted that so badly. He didn’t even know he was into it until she’d brought it up earlier. It was so dirty.
Not even the porn he watched was that filthy. How did she think of that?
His brain began to short circuit. Amanda’s rhythm had gotten sloppier but she kept her composure, looking like an utter goddess as she rode him like he was a toy.
“Come on Ian, cum in Mommy. Be a good boy, fill Mommy with your cum.”
Who was he to deny his mommy?
After another minute of her riding his cock, his hips jerked, toes curled, back arched, he shook and came with an unintelligible cry, releasing her nipple.
“That’s it, baby. Good boy.” He vaguely registered her saying.
He shook under her through his orgasm and once he was done, he laid there gasping for breath.
“Oh my god. Holy shit. Mommy, that was-that was everything.” He croaked.
He felt like a towel that had been wrung dry. He had nothing left inside him, but he still had more to offer the goddess of a woman on top of him.
“I’m glad. Now, you’re going to lick me clean and make Mommy cum. Don’t want my little boy to be greedy.” Amanda said.
She gently pushed his head back down and lifted herself off his softening cock. She positioned herself over his face and lowered her pelvis.
His cum was leaking out of her pussy, dripping down her thighs and onto his face. Somehow, it made his mouth water. Shouldn’t he find it repulsive? Shouldn’t he find the idea of eating his own cum gross?
At the end of the day, it didn’t matter. It’s what Amanda wanted him to do, and he wanted to make her happy. He stuck his tongue out of his mouth and lapped at her folds. His cum was salty but he could taste Amanda too, and she was divine. He grabbed her hips and pulled her closer, trying to force her to actually sit on his face instead of just hover over his face.
“Let go. Don’t be naughty.” Amanda chided.
“Want you to sit on my face, Mommy. Wanna be smothered in your pretty pussy.” Ian said against her skin.
“Are you sure, baby?” Amanda asked.
Ian nodded. “I’m positive. Please, Mommy? I want it so bad.”
That must have been enough to convince her because the next thing he knew, she was sitting on his face. Ian licked his cum out of Amanda as his air began to run out. It didn’t matter though, because the more he licked, the more he tasted her. He’d happily suffocate if it meant the last thing he tasted was the tangy taste of Amanda.
She rose just long enough for Ian to get a few lungfuls of air, and then she sat down again. He went back to exploring her folds with his tongue. He found her clit and was rewarded with a loud more. He licked around it in circles before sucking on it gently. She moaned loudly.
“Yes, baby! Right there!” Amanda cried.
Ian continued suckling gently at the nub, eager to make her cum. His only regret was that he couldn’t see her face when she fell apart. He was running out of air again but he didn’t care. Making her cum was more important. Finally, just as his vision was getting spotty, Amanda shook and cried out as she came. She rose pretty quickly, still shaky.
Ian’s mouth and chin were soaked in Amanda’s juices but he didn’t mind. In fact, he didn’t want to wash his skin ever again. Keep the scent of her on him forever.
She sat on his waist again and pulled him up, his face landing in her breasts. She cupped the back of his head, cradling him to her. She kissed his forehead.
“You did so good, Ian.” She praised him. “You were such a good boy.”
Ian smiled dopily. That’s all he wanted. “Thank you. That was perfect.”
Amanda smiled fondly at him. “I’m glad. Maybe we could do it again sometime?”
“I’d love to, Mommy.”