Sam's New Job Ch. 01: The Offer

Trying a new series with a slower start. I haven't forgotten about James and his Daddy, but I've had a dominant woman on my mind recently.

I'm still very new at all this, so any feedback is appreciated. Hope you enjoy!

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A fresh start

The big city was scary, but exciting. Sam had never seen so many interesting shops, streets and people in his life. His eyes had been opened to a world of possibility and expression, and he was going to dive in.

As soon as his first paycheck arrived, he got a tattoo of a caged bird on his arm. Something his parents would never approve of. A reminder that he'd never be caged again. Wardrobe changes followed. Sam always liked looking a bit feminine, and now was his chance to experiment.

This newfound freedom was intoxicating!

Sam had a girlfriend growing up, but they only ever kissed. She was sweet and caring. He fantasized about being chained to someone's bed. His true desires were masked by a disciplined and chaste exterior. Deep down Sam feared that once he gave in to desires, he wouldn't be able to stop.

It was time to take risks. Dating apps were much more alluring now that they had much larger pools of users. People here were more upfront about what they wanted.

Choices

Swiping on dating apps is addictive. Left for no, right for yes.

Luke, he/him, 26, Bartender, Gay

Pictures of him at the bar, with friends, at the beach, in a club. He had such nice arms, fuck. Sam couldn't help but imagine being pushed against a wall. The club picture. Luke was holding... a leash?

He let out a deep sigh. Swipe left

It was time to take risks, but maybe he should take some baby steps first?

Jessica, she/they, 24, Student - Marine Biology

Pictures of her in colorful outfits, scuba diving, in an arcade, in her room. A bisexual flag and lots of sex toys proudly on display. Then some pictures with her and some cute guy.

Looking for a 3rd, any gender welcome, come play with us!

Sam thought about it for a long time. They were both very hot. Would he even know what to do? He hasn't even had sex with one person, nevermind two.

Swipe left

Ugh... this was going terribly.

Sam spent an hour tweaking his profile and judging his pictures.

Sam, he/him, 24, Software developer

Most of the photos were fairly standard. Sam wasn't buff but he still looked good. A healthy balance of solo and group photos. Only one with a cute dog. He made sure to show his tattoo clearly, and also to mention that he's bi. He has some makeup on in one of the pictures. Maybe he'll find someone that will be into him cross-dressing from time to time.

That's enough for one day.

It's a match

Sam was making coffee when he found her.

Ms. B, 32

She looked exquisite. A photo of her sipping wine seductively, long black dress, leg exposed, heels. Another of her working at a large desk. Then, her lounging back into an antique chair. Full nude. All of the important parts were covered by strategically placed props and some plants in the foreground. She was covered in tattoos.

All of the pictures were taken from below. She towered over each shot. No eye contact either. She was always looking away. Over the camera. To the side.

Sam was enthralled.

Without thinking he swiped right.

It's a match

His heart started racing. How's it possible? She's so hot!

He had to think of a good opening message... damn. After a few bad drafts, he decided to do some work first.

He spent all day thinking about her. Wondering what he should say.

"I like your tat..." - no that was terrible!

*ping*

She sent a message.

"Tonight 7pm or tomorrow at 10pm?"

Huh? What did she mean? For a date?

"Hey B, love your tattoos! I'm free tonight, but what are we doing?"

"Don't speak when you're here. Wear the makeup."

An address followed.

Oh fuck. Was this safe? A hundred terrible scenarios started racing through his mind.

A picture came through. She was on a bed, facing away. Busy on her phone with a dating app. Wearing black lingerie that left her perfect ass exposed.

"I'll be there, can't wait"

He paused for a second. Send

"Good boy."

Sam checked the time, it was almost 5:30pm. He immediately rushes to the shower.

As his pants hit the floor, he notices how hard he is. That picture was still clear in his mind. Damnit, he really wants to touch himself...

No! That's a terrible idea. What if he can't perform later?

Later... fuck. Maybe just a few, slow, strokes to get warmed up? His hand had already moved towards his now fully erect penis.

"Don't speak when you're here"

Sam imagined himself being led to the bed. Not saying a word. She undresses slowly. Teases him for a bit. Then he pulls her perfect ass closer.

"Nnnnggguuuhhhh"

A few short bursts all over the shower door. He collapses against the wall, breathing heavily.

Oh no... should he reschedule? It's definitely too late. Shit.

He cleans up, gets dressed and adds some eye makeup. Just a bit of color around the edges, to make his eyes pop.

6:40pm

Sam doesn't want to be late, so he heads over early. The location is a large apartment building. It looks very expensive. He looks at the address again to confirm. Looks right. Someone let him into the building.

"Hey, I'm a bit early"

No reply.

What if she wasn't even here yet? It was way to early!

He took the elevator up to her apartment. Maybe a knock will do?

*ping*

"You were instructed to arrive at 7pm.

Oh no. Had he already blown it? Maybe this whole hookup thing wasn't for him. This was his last chance to back out.

The door opens.

It's her. She's wearing the same lingerie as in the photo. For the first time, Sam looks directly into her eyes. She's gorgeous.

"You're early."

She turns around and starts walking into the apartment. Sam follows.

"Sorry, I..."

"No speaking. You're not very obedient, are you?"

Sam already started feeling nervous. He already knew he'd do anything she asked.

She leads him to the bedroom.

"Undress. I need to inspect you before we get started."

Inspect him? Sam reluctantly starts undressing. Despite all of the questions that were distracting him, he was erect again.

She grabs his penis. Squeezes slightly. Pulls back. Sam shivers and lets out a soft moan. She takes the condom from his hand and puts it on, slowly.

"Moans and grunts are permitted. No, expected."

His balls are next. He jumps as she squeezes. She leaves her hand there for a moment, looking directly into his eyes. He looks away.

"Acceptable. I want a steady pace, no breaks. I'll tell you when to speed up. Try not to cum before instructed to"

This was absurd, but she was so beautiful. Her commanding tone was incredibly arousing.

She got onto the bed, and opened her legs.

Sam approaches slowly. Ready to fuck her, as instructed.

"You know what, it suddenly seems much smaller. You can go down on me instead"

Smaller?

She grabs onto his hair and guides him to her pussy. Eager to please, Sam starts with a few gentle kisses, before heading in with his tongue. The smell drives him mad. He starts licking more intensely. Fuck. He wants to serve her. He wants to impress her.

"Good, continue like this"

Her thighs press against his head. He can feel her moving around. He tries to read her movement. A quick kiss. A passionate sigh. A gentle suck. Toes curling. A change in pace. A tightened grip.

Sam looks up and sees that she's on her phone. Swiping. She spots his eyes and responds by pushing his face even deeper into her pussy.

"Just keep going, you haven't earned my attention yet."

Eventually, he hears the phone drop onto the bed and her moans grow loader.

"Fuuuuucccckkkkkkk"

She pulls his face away.

"Good boy"

A warm feeling pulses through his body. He blushes.

After catching her breath, she looks at him. Her eyes travel down his body. Then she stops.

Sam looks down and bites his lip.

"I was hoping you'd fuck me tonight, but it's clear to me now that you have a different purpose"

She moves her foot to his mouth. He parts his lips slowly.

"I enjoy using men, like sex toys.

She slips her toes into his mouth. He starts sucking eagerly.

"Usually, I only let my toys inside me for a few sessions before replacing them"

Her foot retracts. She taunts him with a kiss.

"I'm going to offer you a more permanent role, but I won't let you inside me at all"

Her foot moves lower.

"I don't need your clit"

She kicks his balls lightly and smirks. Sam starts moving away, but she corrects him quickly by shaking her head.

"I do need a maid. A personal assistant. Someone who'll follow my instructions exactly. Obediently."

Her foot rubs against his penis.

"My maid needs to focus on me, completely. So I have to take certain measures to make sure they don't do anything naughty."

A harder kick connects, Sam recoils.

"Don't worry, you'll still be punished for disobeying me."

She pulls away and reaches for the bedside drawer.

"You're going to beg me to lock your penis in chastity. You're going to submit your orgasms to me. I'll decide when you get to experience pleasure."

She holds up a small, pink chastity cage and a lock.

"I couldn't help but notice your tattoo. A caged bird, how fitting."

Sam was very nervous. He'd fantasized about situations like this before, but he couldn't just let a stranger lock him up.

"We'll start with 1 month. When you're ready, you'll come back here. You'll beg me. However, the longer you wait, the longer your sentence. For each day that passes, I'll add a month."

Sam starts opening his mouth

"Still no speaking, not today. I'll send the contract over tomorrow. I know you want this, it's just a matter of when"

She gets up, runs her hands through his hair one last time and opens the door.

He gets dressed and heads out, still in shock.

"It's just a matter of when"

Those words echoed in his mind all the way home.