Her coworkers had seen her femme up once or twice before, the job interview, and when she got dragged on stage for a keynote presentation, but her natural look was very much a "working from home" vibe, even when she went to the office.
Normally she'd drag herself into work with a hoodie and a hangover. Hair tied back with a knot and a pair of rotten old sneakers she'd never remembered to replace.
Dressing down meant she could get an extra thirty minutes of sleep, which was no small amount given she regularly spent most evenings hunched over a computer, alternating between last minute fixes for work, and various Japanese comics of a dubious nature.
Not today. Today, Cherry made an effort.
She'd borrowed her roommate's lipstick. Some of her clothes too. She'd even worn the uncomfortable shoes she'd bought for a wedding. Ones she promised herself never to wear again.
The reason? Today was a special day at work, and it never hurt to make a good first impression with the new boss. Cherry got a few looks on the way into the office, but the arrival of her new boss turned everyone's heads.
"I'd like to introduce you all to our new VP of Engineering, Stevie."
"Hello everyone, it's wonderful to meet you all. I imagine some of you might be a little surprised. Stevie isn't a very common name for a woman..."
Cherry was surprised. Yes, she'd been expecting another dude in a suit, but that wasn't why Cherry was shocked. She'd met Veronica at a party, back in university. Somehow she looked even taller than before, too.
"Cherry, isn't it? I haven't seen you in forever!"
"Oh, you know each other?" The founder was all smiles. "Wonderful! I'll leave you two to catch up."
"You know, I almost didn't recognize you." Veronica was smirking.
"Er...Um..." Cherry didn't know what to say. She was still a little shocked.
"Although it doesn't seem like anything else has changed." Veronica laughed. "Still as timid as ever."
"Err.."
"You look sweet though. Good enough to eat!" Veronica leaned forwards and mimicked taking a bite. "Still the same old Cherry."
Veronica walked off without saying a word, moving onto the next coworker for pleasantries and introductions.
The meeting had wrapped up, and shortly afterwards Cherry was back at her desk, miming productivity. She couldn't think straight. Her mind was replaying the moment over and over again.
Not her last meeting with Veronica, but her first.
--
She was twenty, and it was her first real party at college. One of her dorm mates had dragged her away from the computer, insisting that Cherry go to at least one party. That was where she'd met Veronica for the first time.
Cherry had been hiding in the corner, nursing a coca-cola without alcohol, wondering how long she'd have to put up with the loud music, when Veronica approached.
"Hello."
"Um, Hi."
"I haven't met you before, are you a freshman?"
"F...F...Final Year.."
Cherry's brain was in a total panic. The captain of the swim team was speaking to her. The captain of the swim team was leaning over her. She alternated between trying to make eye contact and staring at her feet.
"Are you OK?" Veronica had gently grabbed her chin, lifting it up. "Had too much to drink?"
"I'm the des-des-designated driver!"
Cherry was torn between collapsing onto the floor, or pushing her chin forwards into Veronica's hand.
"Shame. It would have been fun to share a drink with you."
"I...I..."
"Nervous?"
"Yes...First...Party."
"Oh. Don't worry. I don't bite."
Cherry's mind went into overdrive. Imagining Veronica leaning over her and gently biting into her neck. She couldn't stop herself from blurting her thoughts out.
"P..Please."
"You're so fun to tease, Cherry." Veronica sighed. "A shame."
"O..oh?"
"It looks like your friend needs a ride home." Veronica pushed Cherry's chin with her finger, "See?"
Cherry's dorm mate was covered in vomit.
"Oh...Jessie. Oh no."
"It looks like she won beer pong though." Veronica laughed. "Oh well."
Veronica grabbed Cherry's hand, and scribbled out a phone number. "Call me when you get home, ok? So I know you're safe."
--
"Cherry? Cherry?"
She was spaced out in front of her computer. Seven unread emails. Two slack notifications.
"The new boss wants to see you."
Cherry froze in place.
"Um. Sure. One sec."
Two of the emails were from Veronica. One of the slack messages too. Cherry quickly wrote out a reply, then deleted it. After a few attempts, she managed to type out "I'm on my way!" and hit enter.
Standing outside Veronica's office, Cherry couldn't bring herself to knock.
"Cherry, is that you? Do come in!"
Cherry regretted wearing the uncomfortable heels. Out of practice, every step she took was a risk, and as a result, it took an embarrassingly long time for her to take a seat opposite.
"Well, Cherry, as you know I'm doing one-on-ones with every member of the engineering team."
"...Yes..." Cherry nodded meekly back.
"I have to say, I'm really impressed with the work you've been doing. It says here you were on call for three months, during product launch?"
"Well.. Yes... Um."
"Just you?"
"Kinda. Um."
"Are you ok Cherry?" Veronica closed her laptop lid, "You seem a little out of it."
"I... I... Um." Cherry was stumbling over her words. "I'm... I'm sorry!"
"Cherry?"
"I never called you back. I'm so sorry. I had to take Jessie to the ER, I thought she'd vomited up blood, and I... Um... It was 5am by the time I got home and then it was too late but then..."
"Really?" Veronica was holding back laughter. "You know, I thought i'd scared you off. It might sound like boasting, but you were the only one who never called me back. I did wonder if i'd gone too far."
"Umm... No... not... no." Cherry wanted to curl up into a small ball.
"That or you didn't like me."
"No..no...um. Yes. No."
"Don't worry Cherry. I'm just teasing. I heard from Jessie's friend that you two got home in the end." Veronica sighed. "Never mind, eh?"
"oh."
"This probably isn't a great conversation for work." Veronica sighed. "Don't want to get into trouble on my first day."
The rest of the conversation went as well as it could. Cherry stammered out a few answers, often consisting entirely of one word. Veronica promised to fix some of the on-call burden, too.
"Oh, and Cherry, just before you go!"
"Yes?"
Cherry didn't want to turn around. It was hard enough to stand straight.
"My number's still the same. Give me a call if you'd like to get drinks after work sometime."
"S--Sure."
"Oh, and, by the way, you look great today. Glad I'm not the only one putting in the effort!"
Cherry tried not to squeal out a thank you, and wobbled her way back to her desk.
--
The next day, her flatmate was a little surprised when Cherry asked to borrow another outfit.
"Again? Really? Not that I think it's bad, but... two days in a row?"
Cherry didn't know how to explain it. It sounded silly. Dressing up to impress her boss, her old college crush. The one she'd never had the guts to call.
"M...My...Boss."
"What. Some jerk is making you dress up?"
"No. Um... I..."
"Ohhh. Say no more."
On her way into work, Cherry pulled out her phone, for the eight or ninth time that hour. She scrolled down to Veronica's name, opened up the message app, and then stared blankly at her phone.
"I'll do it after lunch."
Lunch was a team affair. Everyone crowded around a long table. Cherry had planned to sit next to Veronica, but had arrived late and ended up stuck at the other end of the table.
It didn't help that she could still see Veronica. It really didn't help that Veronica would occasionally catch her staring, and wink back. It really, really didn't help that Cherry couldn't stop staring.
"Cherry?"
"Um. Oh."
"It's time to go back to the office."
Everyone else had vanished. Cherry had been looking at her phone, still unsure what words to type out.
"Oh. Hee. Something on your mind?" Veronica snatched the phone out of her hands. "Let me help you."
Cherry looked on as Veronica wrote out "Hey V, I'm free this friday if you'd like to get a drink? Love, C." and hit send.
Veronica handed her back the phone. "Was that too hard?"
"Um..Um.."
Cherry's phone beeped. A message from Veronica.
"I have a late meeting on friday, but we can go out afterwards if you don't mind waiting."
"Well" Veronica was leaning over her. "Can you?"
"S...Sure." Cherry's hands were trembling.
"Use your phone words, Cherry."
"S..Sure." Cherry typed it out, letter by letter. Somehow she hit 'Send', too.
"Well. That's sorted. Come on, it's time to get back to the office."
--
Her roommate couldn't believe it. Three days in a row. Even with the uncomfortable heels.
"Cherry, if this is going to be like this every day of the week, we're going to have to go shopping."
"Um. Fine."
"Cherry, are you ok?"
It was weird enough to see Cherry dressing up, but she'd never been enthused about shopping. Not unless it was for anime figurines.
"I... Um... Veronica... She... Um."
Cherry ended up pouring out all of her thoughts at once. How she'd met Veronica, seeing her again at work. Yesterday's plans for a date.
"Wait, Slow down. Deep breaths."
"My... My boss. Date... date with my boss. Friday. Friday."
"Right. Cherry. We're going shopping, after work. Thursday. Ok?"
"Ok."
Cherry took a deep breath. Only three more days until the date. Thankfully, she had an awful lot of work to catch up on.
Back at work, Cherry ran through her unread emails and double checked the calendar. There wasn't any team lunches, or meetings. She double checked Veronica's calendar too, just to make sure.
Every time she got an email from Veronica, she'd space out for a couple of minutes, and her usual razor like focus had been shot to pieces. Veronica had all day meetings with the founders, along with the investors, so Cherry hoped that today would be a reasonably productive day, without interruptions.
"Thinking of wearing this for our date on friday."
Fifteen minutes into the start of her day, Cherry was once again completely lost in her imagination.
--
Thursday was a blur. Somehow she found the ability to think in short bursts. Somehow no-one noticed her moaning in the toilet.
In the evening, her roommate dragged her through the outlet mall on the edge of the city. She'd been wanting to drag Cherry out shopping for what felt like years, and just wouldn't accept Cherry's "This'll do" for any of the outfits she tried.
It felt like a whole week had passed by the time Cherry got home.
"I can't wear this to work."
"Oh, you totally can."
"I can't."
Somehow, her roommate won the argument.
Come Friday morning, Cherry was wearing the dress. It matched the new shoes cherry had bought. Just as impractical as the ones she'd been wearing all week, but just a little bit more comfier. Five times as expensive, too.
Cherry barely recognised herself in the mirror. Her flatmate had brushed out the split ends. Her flatmate had helped out with her makeup, too.
Even her coworkers were a little surprised.
"Going to an interview, Cherry?"
"Not really. Meeting a friend after work."
"A friend?... Or a Friend?"
"Um. Heh. Old college friend. Wanted to look nice."
"Well, good luck!"
Five pm rolled past in an instant. No emails from Veronica. Not even a single slack message. Somehow Cherry had managed to catch up with all of her work.
She took a deep breath, and placed her phone next to her desk.
Five minutes past. Nothing.
Ten minutes past. Nothing.
Cherry put her phone back in her purse, then immediately took it out again. Double checking she had signal, and battery, just in-case Veronica had tried to call.
She went back to her work computer and looked at Veronica's calendar.
"Investor Call 5-8pm."
With a sigh, she re-opened her work email, and desperately searched for something to take her mind off the wait.
--
"Hey" Veronica was standing behind her, and had rested her head atop Cherry's shoulder. "What you working on?"
"Erk!"
"Sorry about the wait, Cherry. Hope you didn't mind waiting."
"I... uh...um..."
It was almost ten pm. Cherry had given up on work and had started reading things to take her mind off the date.
"Oooh. Fanfic." Veronica laughed.
Cherry had tried her best to think about anything else, but smut was the only thing that kept her mind occupied.
"No wonder you never replied."
Cherry tried to close the tab and check her phone at the same time. It didn't work.
"Come on, I'll take you home, at the very least."
Veronica grabbed Cherry's hand and helped her to her feet.
"Did you drive in?" "N..no."
"Well, grab your things, I'll drive you home."
Cherry wasn't really paying much attention, she was just following behind Veronica, trying to walk at a fast pace without tripping.
"One sec."
Veronica ducked into her office and returned bearing a motorcycle helmet.
--
Cherry wasn't the adventurous sort. She'd never crossed a road without looking both ways three times over. She'd never ridden on the back of a motorcycle.
At first, Cherry was rather hesitant. Unsure about hugging onto her boss. Within a second or two, she'd immediately changed her mind, and had wrapped herself around Veronica's back.
"Cherry? You can let go now."
"Ummm..."
She didn't want to let go. Not yet. She'd already regretted enough of her inaction around Veronica. A few more seconds of contact wouldn't hurt.
Veronica peeled Cherry off and helped her off the bike.
"Let me help you with that."
Once again, Cherry was standing before Veronica, with her chin being pulled up by Veronica's hands.
"I... UUhhhh." Cherry blinked. "This isn't..."
"You seemed a little nervous on the bike, so I thought I'd stop a little early."
They were only a few blocks downtown. It had only been three minutes on the back of the bike.
"Sorry. I... I've never..."
"I guessed." Veronica laughed. "No matter. How about you come inside, for a coffee?"
"Coffee?"
"Yes. This is my apartment building."
--
Cherry was having trouble breathing. She was having trouble walking. She could barely think straight. Her boss. The captain of the swim team. Holding her hand.
"I moved in pretty recently, it's a really nice building..."
"Uhuh."
Cherry squeezed Veronica's hand tightly. She wished that the elevator would suddenly halt, and that she'd be trapped in this moment forever.
"I'm sorry about the mess. Just take a seat on the sofa. I'll be back in a second. Let me change out of these."
Cherry suppressed the urge to say "No." It really didn't help that Veronica looked incredible in her motorcycle leathers.
Sitting by herself, she pulled out her phone once more. It had only been ten minutes since they'd left the office. She sat watching the seconds tick over on her phone, trying her best not to panic.
"Cherry? Ah."
She panicked.
"Cherry, I'd like to introduce you to my wife, Emma."
Cherry would have collapsed if she hadn't been sitting down. She might have run for the door too, but was terrified of making a scene. Somehow she managed to blurt out a reply.
"He...hello ... Emma."
--
Life wasn't fair.
Emma was too perfect. Even freshly dragged out of bed, she looked like a movie star. Cherry couldn't help but compare herself to her.
Cherry had spent more than an hour getting ready. Three hours of shopping. Practicing her makeup. Emma, by comparison, had thrown on a dressing gown and was breathtakingly beautiful.
"Cherry. Hmm."
Cherry mumbled out a response. She couldn't bear to make eye contact with Emma, nor Veronica.
"How did the date go?"
"Um.. I.. Me?"
"Yes you." Emma laughed. "A shy one, aren't you? How did the date go?"
"We... um... We... Nothing."
"Oh?" Emma was smirking, not that Cherry noticed.
Cherry was still staring at the glass of alcohol in her hands.
It took all her self control not to down the drink in one, and fuzz out her brain for the evening.
"I was working all night, Love. We didn't even get to the bar." Veronica explained.
"Shame. She is just as cute as you said."
It felt like a job interview. Cherry on one side of the table, Veronica and Emma on the other. Worse than a job interview.
"Well. Hmm. I'm in a good mood." Emma leaned over towards Cherry, lifting her head up. "Do you like my wife?"
"Y...y...yes."
"Well, I'll make you a deal. Ask me nicely, and maybe I'll let you two have some fun together."
"Such a generous wife." Veronica laughed.
Emma put her finger to Veronica's lips. "Behave."
"Yes Ma'am."
Turning to face Cherry, Emma repeated her question.
"So, Cherry, would you like to have some fun with my wife?"
"I... I...I..."
"Is that how you ask nicely. Look me in the eyes."
"I... I..."
"Good girl."
Cherry froze in her seat. Emma had walked over to her side of the table, and was happily looming over her.
The dressing gown wasn't hiding much.
"Now, I ask again. Is that how you ask nicely?"
"I...I..." Cherry's brain was stuck in a loop.
"Why don't you get on your knees." Emma took the glass from Cherry's hands. "Like a good girl."
"I... I..." Cherry fumbled onto the floor, "Please."
"Don't forget to look me in the eyes."
Cherry looked up.
Emma was smiling.
"Do you want this? Say it clearly."
"I... Please. Yes. I want... Please."
"Beg."
"You heard her, Cherry. Beg." Veronica was standing behind her.
"I... I.."
Veronica grabbed Cherry's hair, and pushed her head forwards.
"Be a good girl Cherry." Veronica. "Ask Emma nicely."
Cherry had only just noticed that Emma wasn't wearing anything underneath the dressing gown.
"I... I... I..."
"You don't have to speak Cherry. You just have to beg."
Cherry leaned forwards.
"Good girl."
--
Cherry woke up with some confusion. It wasn't her ceiling she was staring at. It wasn't her room, either.
The memories of last night flashed through her mind. How she'd humiliated herself. How they'd used her. How she'd been forced to beg. How she'd been left to sleep on the floor when they were finished with her.
The collar they'd put on her was still tightly fastened around her neck, too.
It turned her on.
"Naughty girl. Did you forget?"
Emma had caught her. She had forgotten.
"I...I...I..."
"You aren't allowed to play with yourself, Emma."
"Sorry Mistress."
"Have you forgotten what you are?"
"I... I... I'm your good girl. M..misstress."
"Show me."
Emma crawled towards the edge of the bed, and looked up towards Emma.
"Please."
"Again."
"Please."
"One more time."
"Please. Please." Emma rushed her words. "Mistress, Please."
"Good Girl.""
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