Yes, Mommy Ch. 01

"Do your fucking job right, Henry! Jesus Christ, what are you, five years old? If I ever have to call you in here again, you're done! You hear me? You'll never work in this business again! Now get the hell out of my office."

Mona could feel every set of eyes on the floor anxiously awaiting the pile of shit the boss would shovel in their faces now he was in a particularly bad mood. He was a stern disciplinarian and nobody enjoyed working with him, least of all someone as reserved as Henry. Even slinking back to his desk with panic in his eyes, Henry carried a certain charm, something magnetic and beautiful about him. But Mona was never quite sure what it was. He couldn't have been older than twenty-six, but she was unsure.

He had recently transferred from the Ottawa division, but he made little impact upon arrival. Mona had been with the company for years. At thirty-two, she could still turn heads when she wanted to, but never Henry's. Not that she ever really tried: everyone in the office knew she was a lesbian.

She found Henry alone at the table near the coffeemaker. As she approached the break room to get another coffee, she heard small sniffling and wondered if she should retreat.

"Henry?"

His head snapped to and he hurriedly wiped his eyes.

"Yeah?" His voice was soft and small, and she could tell he was struggling to keep himself composed.

"How ya feeling, bud?"

Henry's eyes darkened. "He humiliated me in front of the whole office!"

"Yeah, he's a bit of a prick," Mona said.

Henry chuckled. "Understatement," he giggled, wiping his nose. "Hey, Mona? Um... thanks. It's kinda nice someone cares how I feel."

"Sure." She pulled up a chair beside him. "Totally valid being fucked up about it. If it was me I'd have pissed in his coffee," she admitted.

Henry finally smiled, a big toothy grin that lit up his whole face.

"You would not!" he teased.

"Boy, you better believe I didn't go to school for ten years just be treated like a child," insisted Mona. "That right there: belittling? That's pussy-repellant right there! 'Here's your coffee, boss. Drink it up; it's delicious!'"

They joked like that for a little more than an hour, Mona trying her hardest not to be too awkward. She fell into the habit of overcompensating for her less-than-smooth talk with more and more absurd humor. Henry did not seem to mind, and Mona began to wonder how long it had been since he had had a real friend. She felt a little silly about it, but he seemed never to know what he should be doing, like he needed permission to just be.

"Shit, it's getting late," Mona realized, her watch ticking away at 1:57. "Fuck, we're late! We were supposed to be at the meeting at 1:00!"

They tried and failed to sneak in the back, but being found out gave them a kind of conspiratorial bond, something juvenile over which to poke fun at the boss. They spent the entire floor meeting exchanging trite jokes and stifling laughter at the boss's expense. By the end of the day, Mona felt very confused. She always thought of herself as a lesbian, but she certainly could not deny how badly she wanted to sit on Henry's face. Almost as quickly as the thought came, it vanished.

"For fuck's sake, he's a person, not a toy!" she thought. "Don't take advantage of his vulnerability. You are his friend, not his partner."

Still, she wrestled with a damp spot in her panties as she clocked out and waved goodbye to Henry. His cheery farewell sent a flash of nerves up her spine.

Arriving home, Mona tried to come but found that her favorite porn videos did nothing for her. Her mind kept drifting back to thoughts of Henry. The way he bit his lower lip when he was nervous. Those dimples he tried to hide. The way he giggled, sweet like a drink after a long day. And his intellect! Seemingly the one man in the world who could keep up with her. Always something to say, if after a fair bit of provocation and encouragement. His soft features: big, warm brown eyes and long black hair delicately braided. She imagined him beneath her, head between her legs, his lips hesitantly pressed against her own. Encouraging him, telling him how she liked her pussy kissed. His tongue against her clit, then gently inside her. Looking up at her with those big doe eyes, as if to ask if he was doing it right.

She reached her vibrator and slid it deep into her pussy. Henry was so adorable, so innocent, and however confusing to her, she wanted him. She wanted his tongue gently teasing her heavy tits, desperate to please her. She wanted him on his knees, face buried in her cunt, her juices dripping from between his lips. His tongue inside her, soft and curious. His thumb circling her clit as he ate her out, savoring her taste. She wanted Henry struggling to breathe as she rode his face, bucking her hips and grinding her swollen, aching pussy against his nose and lips, demanding he service it. Mona pumped her pussy harder, faster, deeper as she thought of him writhing beneath her, begging to cum and never quite able to get off. She had no desire to touch his throbbing cock, which by that point would have to be leaking precum all over her bedsheets. No, she just wanted him bound and gagged, bent over her bed with his ass exposed. Mona placed a second vibe over her clit as the fantasy took shape in her mind. A seduced Henry nervous as she lined the head of her strap-on against his tight hole. His eyes going wide as she started to press her weight into him, his moaning as she slid inch after inch deep into his fuck hole. Her thighs slapping against his as she bottomed out and continued to thrust, faster and faster, hands tight against his hips as she fucked him, grinding his face against the bed. Slapping his ass til it glowed red beneath her, thrusting that cock deep and deeper.

"Oh, fuck, yes!" she screamed. "You filthy fucking slut!"

She turned her vibrator to max and pushed it in deep before the first wave of her orgasm began to rumble in the back of her mind. It spread to her thighs and then to her feet, a river of pleasure flowing up her back and into her ears. A second wave and her toes curled around the satin sheets, screams from some primal place as she gushed all over her bed and legs. Mona would have minded the mess, but she was more interested in why she had cum so hard.

**********

Over the ensuing weeks, she strengthened her friendship with Henry, and it was not long before co-workers assumed they had initiated a romance. Mona could not understand where this rumor had started or why. Had they paid any attention at all to Henry's needs and the way he always seemed nervous, even when smiling, it would have been clear he was struggling with severe social anxiety and not in a place where he could date someone. He could barely commit to their friendship: he always seemed off, inauthentic, like something was never quite right about the way he walked, the way he carried himself. It was clear he enjoyed Mona's company but always waited for her to initiate conversation. And even then, she tended to dominate the conversation. He seemed content, grateful even, to let her dazzle him with sharp wit and scathing commentary about the office drama. But those marvelous brown eyes of his... Perhaps they had seen too much. She would search within them for answers, but they were just blank, like a forest after a great fire.

They spent almost three months eating lunch together, goofing off, and learning just about everything about one another. As she was learning how much he hated pickles because of a bad sandwich, or how much he preferred Star Wars to Star Trek (blasphemy if she ever saw it!), she began to suspect he was probably gay. She wanted to be a good friend to him, but she also wanted to wrap her legs around his head. This false dichotomy kept her in a state of near-constant confusion. Even Henry began to notice how often she forgot to forward a memo, how often she seemed cross and distracted with little things that never used to bother her.

"Hey, Mona?" he asked one morning, shaking the snow off of his winter cap.

"What's up, Boo?" He didn't mind the pet name as much as he used to.

"What, um... What's-Is something wrong?"

She tried to be chill, but she knew what he was talking about.

"I'm cool," she insisted, hanging her jacket up in the coat room.

"I just, um... I feel like you've been kinda distant lately, and I wanted to check in to see if there was something going on in your life you wanted to talk about."

"Don't worry about it," she chuckled. "I'll be OK, just dealing with a lot of stress, that's all."

She knew as she sat back in her office chair that Henry was worried about her. It reassured her but also made her feel a twinge of guilt as she stared at her computer monitor. From across the empty room, Mona could just about feel the panic with which he clicked his pen against his desk. It was late December and everyone else was out for the day, but they had gotten on the boss's bad side and been stuck with shit detail. It took an hour for him to work up the courage to approach her, delicately tapping her shoulder.

She turned her chair to find a very perplexed Henry cocking his head. She turned a bit red and tried to keep her voice level.

"It's you. I, um... You're..."

"Did I do something wrong?" he asked, eyes wide.

"No," she assured him. "I'm just usually into women, so it's weird how badly I want to take you out. I really like spending time with you, and I was wondering if you wanna go out for drinks or a movie."

"Oh," he blushed, somewhat dumbfounded. "So that, that was... that's why you..."

"Yeah. I mean, if you're gay or taken or whatever, that's fine!"

"Well, I've been with a few guys before, but... Did you think I was gay? I like girls, too, you know."

"Sorry, I shouldn't have assumed," she admitted. "Should we just pretend this didn't happen?"

"I'm not saying no," he corrected her. "I'm just, you... OK. Sure. I can give this a shot. I'm just not a very good date. I mean I've dated before, kinda. I mean, sex. I mean, no one's ever..."

His face was scarlet, deep and ruddy like he was out of breath. Her coy smile made it worse.

"Women have never been so forward with me," he chuckled, fiddling with his hands. "I-I've never really been hit on before. I've matched on Tinder, but not often, and only with guys looking for one night stands."

"So, tonight? Dinner at the Rouge?"

"Sure."

**********

Mona knocked at Henry's door with a calm confidence. When he opened the door in pajamas and a Black Sabbath tee, she thought he had forgotten their date. Her indignation softened as he explained himself.

"I'll be ready to go in a bit, Mona." He fixed her a whiskey on the rocks and apologized for getting caught up in something personal. "I just got a bit distracted. I'll be right out."

"Take your time," she assured him, admiring his physique as he walked away. His hips swayed a bit and she drank in the image of his round ass peeking out the top of his PJs. There didn't seem to be a trace of hair on him, just cool, clear skin and more curves than a bowl of soft serve.

Henry disappeared into his bedroom for the next half hour. During that time, Mona helped herself to a few more drinks, not enough to get drunk but enough to make her seek out the bathroom. She closed the door behind her and tried to navigate her way to the toilet without touching any of the used panties littering the floor. At first she thought nothing of it, save a bit of judgment towards his messy roommate, but when she tried to knock the panties resting the toilet seat onto the floor, she was shocked to find cum leaking out of them. There was something else, in addition to the strong odor, something like...lube? She followed her nose toward the shower and pulled back the curtain to find a recently used vibrator smearing KY jelly against the side of the tub. What had Henry gotten up to?

"That perv!" she thought, eyebrows knitted in erotic surprise. "Stealing her panties and cumming in them!"

She bit her lip, mind wandering to ever naughtier fantasies. Henry emerged from his bedroom soon after dressed in a commanding dark blue suit he seemed very uncomfortable wearing.

For her part, Mona wore a sleek black dress and a matching pair of fuck-me pumps.

"Call me ambitious," she had thought.

The date was a casual kind of formal. They talked, ate expensive food, drank fancy wine, and tried to make merry, but the bathroom scene kept her rapt attention, far removed from the conversation with Henry. She tried not to exacerbate his anxiety or be rude by ignoring him, but no matter how much she tried to enjoy the date, she just kept coming back to those soiled panties, filthy with fresh cum, and the vibrator that had recently been inside his ass.

When they got to Henry's door, he asked her if maybe they shouldn't date anymore.

"I'm sorry," she said. "I had a lot on my mind."

"You barely looked at me all night!" he whined. "Maybe we're just not compatible. As a couple, I mean."

"No, that's not it!" Mona interrupted.

"Well, then what were you thinking about?" he asked, voice low and resigned.

"To be honest," she began, lifting his eyes so she could see his reaction, "I was thinking about those cum-filled panties in the bathroom and that purple vibrator of yours."

The color drained from his face. She shushed his embarrassed stammering with the suggestion they talk about it inside. He agreed and locked the door behind them.

"Stealing a lady's panties and busting in them?" she teased. "Scandalous! Did you, like, rifle through her panty drawer or raid her dirty laundry?"

"I need a drink," he swooned, reaching for the spiced rum.

"Oh, my God! You didn't!" Mona laughed. "Did you sniff them too?"

She eased up a bit when she saw the worry and shame burning in his eyes, like he was afraid she hated him now.

"OK, maybe I did cross the line a bit there..." she admitted. "I was just teasing, but that doesn't excuse my behavior. I didn't mean to make you uncomfortable, and I'm sorry, Henry."

"They, um... Well I guess as bad as this looks, it can't get much worse." He took another sip from the bottle. "There is no roommate."

"But, then whose-"

"They're mine," he confessed. "They're my panties."

"Then can I be honest with you?"

"Yeah?"

"That just makes this whole night way more interesting," Mona purred.

Henry could see smoldering hunger in her eyes, like she had been waiting a long time for this moment and now something had loosed her desire.

"So that's what's been on your mind?" Mona pressed her advantage. "Worried I couldn't take you serious if I found out you dress in those cute little panties?"

"Well... yeah."

She grabbed his hand and guided it under her dress. His eyes got wide when he realized she hadn't worn panties, and she was about dripping wet. She guided his fingers over her clit and then slipped one into her pussy. She had never seen a more adorable kind of shock.

"Does that answer your question?" she asked, retracting his fingers. "It's gonna take a lot more than that to scare me away. If that's your kink, that's your kink. Who am I to judge?"

"It's not really a kink," he countered.

"Oh?"

"I'm... I just..."

The gears in her mind clicked, and suddenly she understood the source of all his anxiety, every little tic that kept everyone but her well away from the shy, quiet guy at the office. It's because he wasn't a guy. Henry was a girl!

"Oh, Boo, are you transgender?" she asked.

"Yeah," he sighed. "I am."

She reached her arms around him and hugged him close.

"You big dope, why didn't you tell me earlier?" she joked. "This explains so much!"

"It's hard to be a sissy," he said. "We don't even like us."

"What's a sissy?"

"Oh, you know, boys who dress like girls, act like girls."

"But you are a girl. Sissy doesn't really suit you, now that I think about it, Henry."

"Jessi, actually. I kinda prefer Jessi."

"See?" Mona insisted. "You have little in common with most men. Maybe what's between your legs, Boo. But what's between your ears is all woman. Can I assume you want me to use she/her pronouns?"

Jessi blushed, a deep, profound crimson like she had never been seen before and didn't know how to behave. She nodded, a wide smile suggesting this was the first time anyone had ever validated her.

"I can show you," Jessi squeaked. She had decided to trust her friend with her most intimate secret.

"Show me what?"

"Well," Jessi began, "I've been taking hormones for almost six months now, so I was thinking I could show you what I really look like, underneath this ugly suit and tie."

"I bet you look hot," Mona chuckled.

Jessi disappeared into her bedroom and when she emerged half and hour later, Mona almost dropped her whiskey. Jessi was still blushing, like she was worried Mona would change her mind. A bit of drool slipped over her orchid lips as she looked Jessi up and down in awe. No way she was anything but a woman.

Her long black hair was wild, untamed and sultry against her neck and shoulders. Extensive tattoos suggested anything but a boring office worker: skulls, roses, and barbed wire circled her thighs and danced across her exposed tummy. Jessi's panties left nothing to the imagination: her small cock strained against her panties, a low cut black pair with soft pink polka dots, a bit of lacy trim, and a small bow right below the hemline. Mona could feel herself leaking onto the couch as Jessi adjusted the straps of the cutest black bra she had ever seen. The lingerie exposed almost every inch of her, from the grim reaper on her left thigh to the bullet holes inked across her right. Her plump lips, framed by a slash of glossy black lipstick, practically begged to be kissed. Smooth, soft face expertly made up. But her eyes were the best part. Big and eager, thick black liner and a bit of mascara. Glittery eyelids a deep, smoky purple. She didn't have a masculine bone in her body.

"Um, Mona? You're kind of staring..."

"It's just nice to finally meet you."

"No more lies," Jessi agreed, sitting beside Mona. "No more Henry."

She was intoxicating. Mona leaned in and kissed Jessi along the nape of her neck. She ran her tongue along the skin and savored the scent of sweet peach and something else. It was like she could smell Jessi's desire. She looked into those brown eyes and saw everything, Jessi's whole being laid out and vulnerable.

"You're beautiful," Mona promised. "Can I have you? I just want every inch of you right now."

"But I don't like to be the dom," Jessi protested.

"That's not what I meant- Wait, what?"

"Oh, well, I kinda always wanted to be dominated by a daddy. Or, in this case, a mommy?"

Mona broke a devious smile as Jessi explained what she needed from their relationship.

"Oh, baby girl... You naughty little minx," Mona chuckled as Jessi shared her favorite porn tabs and the filthiest tumblrs Mona had ever seen. "Yes, yes, and yes. We can arrange that."

"Yeah? I've just really wanted-"

Mona kissed her deeply, drinking in the drunken aroma of the woman she had been lusting over for weeks. As they tumbled into the bedroom, Mona grew more aggressive. Jessi gasped as Mona kissed her neck, deliberately dragging her tongue across it. Jessi moaned as her new Mommy began to suck on the sensitive skin of her shoulder.

"Tell me, you little slut," Mona demanded. "Did you wear those panties on our date tonight?"

"Umm..."

"Look me in the eyes and address me proper!" Mona growled.

"Y-Yes, yes Mona."

"Yes, what?"

Jessi couldn't bring herself to say it. Mona grabbed a handful of Jessi's hair and forced her to her knees, back arched painfully.

"Yes, what?" she insisted.

"Yes, Mommy! Yes, I was a bad girl!" Jessi answered.

"Is this what you want? To be treated like a whore?"