Chapter 6 – In Deep

Jack stares down at his new boss and once step-sister as she rubs her face on his dick. 

Jolts of electricity run from his abdomen to his head with her every movement. 

"You've got a wonderful cock, Master."

'Holy shit. Is this actually happening?' He wonders internally.

Not that he was complaining, mind you. This was everything he wanted and more!

Smiling down at her, Jack puts his arms up on the back of the couch and spreads his legs wider so that she had easier access.

Natasha doesn't miss a beat and scooches in as close as the couch will allow her to. She continues to rub her soft cheeks up and down his shaft, staring at it in amazement. 

"I'll be honest, I didn't think you would be game for this, Nat," Jack admits, tilting his head to the side. "Were you always such a dirty gril, or was it something you picked up later in life?"

Natasha blushes, his words sending pangs of embarrassment and shame through her chest. 

"You've never looked as beautiful to me as you do now."

Those words sent a different sensation through her entirely. The heat in her loins growing by several factors.

Choosing not to reply, she instead starts licking the massive rod in front of her. From the base to the tip, she licks - Making sure to cover every inch in her saliva. 

Jack sighs and closes his eyes, a content smile on his face. 

She repeats this for several passes, then changes things up, wrapping her tongue around his member as best she can and moving her head from side to side.

"Yessss." Jack moans, "That's good. You're doing a wonderful job, Nat."

Pleased by his praise, she continues the motion with more energy.

As Natasha looks up at his blissful expression, she thinks of how many times she imagined this scene. How many times had she cum pretending to suck this dick? How many times had climaxed while thinking of him moaning her name?

More than she would like to admit.

She hated giving blowjobs normally. Not much for a woman to like, really. It was only when she was really into her partner that she did it, and, in this case, she could not possibly have been more into Jack. He was everything she ever wanted, and his pleasure ramped up her own exponentially.

Knowing that she was the one making him moan just like she always imagined was both feeding her pride and driving her mad with desire. 

Changing it up again, she focuses on the head of his curved manhood, flicking her tongue in small motions along the upper and lower side of his circumcised tip. It twitches each time, almost as if it was encouraging her in the action. 

A few more minutes pass like this, then Jack decides he wants more.

'Should I test her comfort levels? ...Yeah. Let's do it.'

"Show me your pretty mouth, Natasha. Let me see down your throat. I need to determine if it is worth my time and energy to choke you with this cock you seem to like so much."

Natasha was far too aroused to offer any kind of resistance at this point. She desperately wanted more of him and she was eager to show him just how good her throat could feel.  

She opens her mouth as wide as it can go and stares up at him with sparkling eyes.

Jack was honestly surprised. He expected some pushback with a request like that. Most subs required training, or, more accurately, they needed to build up levels of trust. Trust that their doms would take care of them and not hurt them in ways they didn't like; Trust that they would humiliate them, but not take things too far. This whole thing was a give and take, and she seemed much more willing to give than he would have expected based on what he had seen previously. Was she really new to this? 

'To not only agree, but to do so without blushing or batting an eye? Was she just trusting me blindly or was she secretly a nympho?'

"Good girl, Nat. Very, very good." Jack says as he leans forward and grabs her chin to inspect her mouth like a Vet would to a dog. 

A visible shiver runs down her spine as he compliments her and at the shameful act. She even starts letting out an "Aaaaaaaaah," which nearly makes Jack break out laughing. 

She obviously was enjoying the shame play. But it didn't seem to phase her as much as before. Odd...

Nodding once, Jack lets her go.

'She seems more experienced than I thought. Maybe she has done this before? Ah well. Let's see what she's got.' 

"Show me what you can do, my beautiful little slut." He goads her.

"Gladly, Master~," She responds with a hint of pride and excitement to her tone.

Natasha then, with no hesitation whatsoever, fully engulfs Jack's cock from tip to base in one fluid movement, showing him the true level of experience from the mature 31-year-old woman.

Jack goes cross-eyed at the sensation, leaning forward and hugging her face to his pelvis, without really intending to. 3 years of nothing and suddenly going from his hand to this...It was more than he was prepared for.

She puts up no resistance and laps at him with her tongue as she swallows with her throat, breathing easily through her nose.

Once he realizes what he is doing, Jack lets go of her with all but one hand.

She stays where she is even without his body around her to hold her in place.

For several long seconds.

Jack blinks. 

She is still down there, looking up at him with proud, glistening eyes.

'Okay. Yup. She knows what she is doing.'

Jack pulls at her hair to slowly bring her off his dick. Her eyes never leave his as his cock moves out of her throat and mouth inch by inch.

It pops out of her with a loud suction noise as strings of her saliva keep her attached to it, and more fluid puddles in his crotch.

Natasha looks up at him with a teary-eyed smile, begging for praise. 

"Jesus Christ, Nat. That was incredible. I have been deep throated before, but never for such a long time or so suddenly. There is usually a lot of prep involved in that...You really are a dirty girl aren't you?"

She pouts at him, not getting the amount of praise she wanted, so she does the whole thing again.

"Fuuuuck." Jack wheezes out. There is nothing quite like a good blowjob, and right now Natasha was putting most of the pornstars he had slept with to shame.

Deciding to let the woman do her thing and worry about the rest later, Jack leans back again and covers his eyes with one hand. 

The sensation was mind-blowing. 

Her tongue swirled at his base and her throat constricted, almost milking him. 

When she noticed he wasn't looking anymore, Natasha got a bit peeved. Deciding he was the one in need of punishment for ignoring her, she started to move up and down him like a piston. Her lips tightened as she went the full length of his cock with every movement.

Jack's hips bucked involuntarily and his head whipped back to stare, wide-eyed, at her. 

If she wanted his attention, she had it fully now.

"S-Shit, Nat. If you ke-eeeeep that up I am gonna-"

Once again a loud slurping noise can be heard as she takes him out to speak.

"Do it. I want to taste you. Please, Master?" 

Her coy begging look is so intoxicating that Jack could do nothing else but slowly nod to her in bewilderment.

He lost control of the situation, but he needed to cum, so he didn't care. He had gone too long without and he wanted this to happen just as much as she did.

Or so he could only imagine.

'Finally. I can taste it. It's mine. I earned it.' Natasha thinks in pure ecstasy.

She was beyond the realm of rationality at this point, almost as if it was her orgasm she was working towards, not Jack's. Her prize was seconds away and nothing would stop her from getting it.

And get it she did.

Less than a minute of vigorous head bobbing later, Jack was bucking his hips again. 

"Fuuuuuck!" He growled through his teeth as white spots appeared in his vision. 

An endless torrent of seed spilled from his member straight into Natasha's wanting throat and mouth, just as he had imagined a few days ago.

Jack wasn't sure he had ever cum this hard in his life. No one, not a single woman, had ever shown as much enthusiasm as Natasha just did in her blowjob. She seemed...almost giddy to receive him and her efforts were not in vain. 

Jack came for several seconds and Natasha quickly moved his tip to her lips as she sucked with as much force as she could manage. 

She got every last drop he could give, and kept sucking afterward to make sure of it. 

When he finally arrived back from his flight in the clouds, Jack saw her, swirling his sperm in her mouth, chewing on it, and, once she was sure he was looking, opening her mouth to show him before swallowing it all down.

'What. The. Fuck.' This was all Jack could think. 

His dick should have been completely spent with all that she did, but that last action had him hard and ready to give her some more. 

"Bedroom. Now." He commands, no room for argument in his tone.

His words finally brought clarity back to Natasha as panic sunk in. 

'Shit! I got carried away!'

Jack stands, kicking off his pants, socks, and shoes, before pulling Natasha up from the ground and dragging her towards the door to her bedroom.

Time to backtrack a bit.

See, Natasha never planned for this to happen.

Sure, this was the ultimate goal, but it wasn't supposed to happen now. Not like this. 

There were logistics, outfits, teasing, chance encounters, and many, many more steps that were supposed to happen before she got to this point with Jack.

Meeting him at the restaurant had been a complete coincidence. Being in the same apartment complex wasn't, but he shouldn't have found that out for several more weeks. 

She took a risk inviting him over, but she only planned on teasing him and making him want her more. 

Going as far as they did was never part of her plan. 

Natasha showing her experience was never part of her plan.

And Jack seeing her room was DEFINITELY not part of her plan. 

As such, Natasha had some quick thinking to do. 

"Jack, wait! Please...can't we continue on the couch? My room is a mess. I haven't unpacked everything yet!" She tries.

"Don't care," Jack says heartlessly.

"Well, I kinda do! Can we not, please?" She insists.

This makes Jack pause. 

He was big on trust and not breaking trust...but there were too many inconsistencies with the night.

The way she acted before and after the massage was completely different. 

Jack thought, rightfully, that something suspicious was going on, and, based on her panicked face, he would find answers behind this door.

Jack sighs and stops in his movements. 

He wasn't about to break trust with someone he trusted himself. That was one of his big rules.

"Sure, Nat. I just got a bit excited. Let's move back to the couch." He answers her with a smile.

Breathing a sigh of relief, Natasha nods and stops pulling back on his arm.

Too bad for her, Jack didn't trust her anymore.

Once the resistance was gone, he quickly moves and opens her bedroom door. "After I see what you're hiding."

'SHHHIIIIIIIIT!!!' Natasha screams internally as Jack enters her messy bedroom. She chases after him and wraps her arms around his chest, as if to bodily pull him from her room, but realizes that it is too late. 

Jack's blank expression told her all she needed to know.

He saw.

Clothes were spilled on the floor haphazardly. Boxes were opened and their contents half-emptied or otherwise displayed. A makeup table was a mess with various bottles and containers, some still open. The walls were barren, but freshly painted a creamy off-white - Thank God she didn't have time to hang up her White Mask posters yet.

In the center of the room was a king-sized bed with messy white sheets and a comforter, obviously left in the same state it was in when she woke up that morning. A dresser across from her bed had several of her pants, shorts, and skirts as well as her bras and panties hanging from their ajar drawers, left that way in her rush to pick out a matching outfit. Her closet door was askew, showing several different outfits hung up and ready for her when she needed them. 

But none of this is what Jack stares at.

He couldn't give a shit about the mess.

No, all he was looking at was a large, corner display case in the far right of the room.

One with 5 shelves.

One that was neat and tidy in the otherwise chaotic mess. 

One that had been custom-fitted, even having glass covers over each shelf.

One that was filled to the brim with bondage and sadomasochistic equipment of every shape, size, and purpose.

The top row held coiled, oiled ropes of various gages and lengths hanging from hooks with plaques next to them indicating their typing.

The next row had a display of paddles, whips, and riding crops mounted to the back of the case for both presentation purposes as well as ease of access. Most were monogrammed with an artistic JN either embedded into the material or, otherwise, attached to small metal plates near the handles. Almost as if they were name-brand purses or handbags instead of instruments of pleasurable torture. 

The middle row had a rainbow collage of dildos with varying purposes. Each normal dildo was presented on a large wooden riser of some sort while the longer or odd-shaped ones were hung on brackets in the back, making it easy to see and access whichever one was desired.

There was everything from simple silicone or rubber cocks in different colors, lengths, and girths, to vibrators from small to large, or clit stimulating dildos with wrap around portions, to simple massagers with large round heads. There were also some butt plugs, tails, and beads hung up behind the riser display, and, lastly, a retractable wooden pole that was hung on hooks above the shelf, outside the glass, that any of the previous dildos could be attached to. Once again, the initials JN were on every single one - Clearly a brand name after all. One Jack had never heard of. 

The second to the bottom row had leather cuffs, strips, restraints, and chains along with ball gags, eye covers, and other mouthpieces all hung on hooks. At the bottom of the shelf was another small riser system containing a multitude of different lubes and oils - All with JN labels.

Finally, the last row held metal clips, clothespins, candles, small elastic straps, egg-shaped vibrators with wires, and even a low wat taser with metal clips attached at the end held in small plastic bins. Laying in front of them all was an honest-to-god-gimp mask.  

"H-Holy Fucking Shit," Jack mumbles as he takes in all the various S&M objects.

He slowly turns to see the pale face of Natasha looking right back up at him. 

"J-Jack. I...I can explain." She tries.

"Oh, you will. But first, go and sit on the couch. I need a second to process this." Jack answers in a cold voice. 

Even with it being her own apartment, she listens to his words and does as he says silently.

Natasha's gut had fallen through the floor. The weight of her entire plan and the future of her newest employee seemed to hang in the balance of this next conversation.

She doesn't even speak when Jack opens the door to her other room and sees the various BDSM equipment and furniture still in their JN boxes. 

It was an invasion of privacy, sure, but there were much more pressing issues at hand than that at the moment. 

'Shit. I am so fucked.' She thinks, hanging her head.

* | * | *

Jack was beyond words.

He thought she might be into this and was a bit experienced, but nothing, NOTHING could have prepared him for what he just saw.

Her room had more equipment than most of the sets he worked on!

There was anything and everything he could ever need here in this apartment - Hell, she might own more than he does! 

Not to mention they were all apparently name brand? Just how much had she paid for all this!?!

Most of Jack's stuff was in storage currently, as he wasn't thinking he would need anything more than handcuffs and a soft whip for fun with the kinker ladies he eventually hooked up with. 

To see so much of it here was...unbelievable. 

To be honest, Jack wasn't mad at Natasha.

Sure, she hadn't told him her preferences right from the start, but how does one even bring this kind of thing up if they don't know what their partner is into it? 

Jack had never had that problem. Whenever he did this in the past it was as a service. A job. People came to him. 

Before that, he talked dirty to and spanked his girlfriends, but it wasn't until he started working in the host club that he got into BDSM.

How could he expect Natasha to just all of a sudden say, "Oh, hey, by the way, I am the freakiest girl you have ever met. Tee-Hee."

He could only imagine how being this deep into the fetish must turn off or intimidate other guys. 

Maybe it has even led some of them to abuse her thinking she would like it? Give a douchebag a whip and he will beat a girl black and blue thinking she's into it.

Had she been through something like that? God, he hoped not...

So, no, Jack was not angry at her for hiding this from him.

Jack was a bit miffed that she let him believe she was new to this all, but, again, he never asked her.

Sure, he was domineering, but what if it had all been an act? What if he wasn't as experienced as he let on and she scared him off by admitting to her fetish? He could understand her not telling him right away to protect herself.

He wasn't honest with her in the beginning either...Just kinda jumping into things and expecting her to follow along...

The fact that she did so and didn't kick him out right away was amazing enough as it was. 

No, this was both their fault, and Jack wasn't gonna be a Jack-Ass about it, pun intended.

Besides, he was now in his element! If anything, wasn't this a great chance to do what he loves with someone who might love it just as much? Doesn't this mean that Natasha...That Nat might be perfect for him? 

He wouldn't have to be fake with her. He could just be himself and they could both enjoy it! How amazing would that be? Wasn't he just thinking about settling down with someone now that he got a stable, normal job?

'Cool it, Jack. Don't get ahead of yourself.'

There was a still serious problem, after all. 

'Thank God I left my shirt on...She would know I was White Mask instantly if I took it off. With her this deep, she has to have watched me before. My scar is not all that subtle...'

Jack resolved himself with what he was about to do. He couldn't hide it, and, to be completely honest, he didn't feel like he needed to. Not with her. Not after all he had seen. 

His secret was bound to get out eventually. It wasn't like he was gonna stop having sex just because he had a recognizable scar.

Jack felt like he could trust her now. She was just like him!

Now that he had the full picture, it was time for him to apologize for his behavior and see if he could mend this fence. 

It was only right.

***

Poor Jack. He didn't have the full picture, not in the least. He had only just scratched the surface...

* | * | *

"Natasha," Jack starts quietly after taking a long break in the bathroom. "I...I'm sorry."

Of all the things Natasha thought she would hear, that was certainly not one of them.

"What?" Her confusion was clear in her expression as she faced the still-naked-from-the-waste-down Jack.

"It wasn't right of me to barge into your rooms like that...I was...Something just felt off. I get it now, though, and I am sorry. I hope that you can forgive me. If you can, I promise to be upfront and honest with you moving forward." Jack says with determination. 

He sits next to her on the couch, though further away than either of them had been previously, as he waits for her response. 

Natasha was stunned. 

He looked so sincere and apologetic. It was clear that he was regretting his actions...but why? Shouldn't he be cussing her out right now? Shouldn't he be furious with her? Shouldn't he be pissed about finding out?

'...Unless...Unless he didn't figure it out at all?'

Was she safe? Was her plan safe?

"Natasha...?" He asks again in an even quieter voice. She can see the pain in his eyes as if he was waiting for her to fire him and kick him out of her life forever. 

Holy shit.

She had gotten away with it.

He really didn't notice.

She was fine...Holy fucking shit fucks, her plan was fine!

Swallowing a mouthful of saliva, Natasha speaks softly, "It's fine Jack...I...I am just a bit ashamed is all." 

She looks down at the floor with a small awkward smile, trying desperately to avoid it evolving into a wide grin. 

She had to act and plan her words carefully until she understood the extent to which Jack saw through her.

"You don't need to be ashamed about that! I am the same! I like the same stuff, Natasha! It is probably why our chemistry has been so good! How do I explain this..." Jack says as he runs his hands through his dark brown hair.

What? How? Why was he only looking at things at a surface level!?!

Wait...He didn't have all the pieces. He was missing context clues. He wasn't able to make the right connections...

'Of course, he can't...' She realizes, 'He doesn't know that I'm aware he's-'

"Do you watch S&M porn, Natasha?" Jack asks in a sheepish voice as he removes the last article of clothing he still wears - His V-neck black t-shirt - revealing a long jagged scar on his left pectoral muscle. 

'I can work with this. Everything is fine.' Natasha nearly screams in joy at the realization.

"I...um...I do sometimes...But why ask me-*Gasp*" Natasha was selling it for all she was worth. Her eyes bulged from her head and her hands covered her open mouth. 

"Jack...You're...You're..."

"That's right. I'm White Mask," Jack says with a confident smile, fully exposed to a woman for the first time since he retired 3 years ago - More so even, as Natasha is the first woman to see White Mask fully naked and without his namesake.

'Oh, Jack. You will thank me for this when it is all over. Not during...You will probably hate my guts during...but by the end, you will thank me.'

If Natasha's face matched her internal thoughts, she would look like the Cheshire Cat.