Chapter 4 – The Point Of No Return

Jack was at his wit's end. 

To his left was a beautiful and peppy brunette, in front was a gorgeous dark blue-haired vixen, and to his right was the very woman the acronym MILF was made for. 

He had, somehow, managed to get through most of the questions they asked him. What were those questions? He had no fucking clue. 

All Jack was focused on was keeping his smile in place and looking each of the women in their eyes while trying to not stare at their sinful bodies. 

He failed. A lot.

But, where there is a will there is a way, and Jack was pretty much only willpower right now.

"That will do it, Jack..." Natasha says, sharing a meaningful look with Hannah and Gwen. "I think I speak on behalf of all three of us when I say that we are very excited to work with you. Congratulations, you got the job!" 

You Got The Job!

Those four words rang through his mind like the prettiest bells he had ever heard and, for the first time since he sat down, he relaxed.

He did it. He actually did it. 

He had passed his final hurdle for his dream. Jack felt so happy that he could cry. 

All of the hard work, all of the effort...It had been worth it in the end.

He landed a job at what was to be a very successful modeling agency, if these three women were any indication. 

"Wow...Thank you all so much! Really...it means the world to me." Jack mumbles out with a ton of emotions behind his words and trying desperately not to tear up. He felt euphoric. Like nothing in the world could affect him or bring him down.

"Of course, Jack. We are just as excited to have you as you are to join us." Natasha says with a warm smile. "Now, as your new boss, I will be taking care of the bill tonight and we can plan more out in the coming days. That will include a lot of paperwork for you, so keep your writing hand ready!" She explains further with a laugh, "I still need to show you the office location so that you can get started with all that fancy tech stuff. Do you mind coming in tomorrow? I know it is short notice..."

"Not at all!" Jack nearly shouts. He was hired and he was starting immediately, what could be better?

"Excellent," Natasha purrs. "Shall we celebrate with a hug?"

"Yes, that sounds nice..." Gwen says with her slow Southern drawl.

"Duh!" Hannah agrees, opening her arms out wide.

"Sure!" Jack laughs and stands with the rest as they move together into a big group hug. 

The hands of the women wrap around him and move in slow circles around his body. 

It might have been a bit odd for Jack, but he was not going to let a little physical closeness be a deal-breaker. It certainly never was with his other jobs...

The hug lasts for several seconds and Jack feels almost smothered by the soft flesh surrounding him. He probably would have gotten aroused by this normally, but he was just too happy and relieved to even think of it right now. Instead, Jack pulls the women close and basked in the fact that he was part of something normal, for once. A regular employee of...of...

"Hey, what's the business name going to be?" Jack asks suddenly. Somehow that wasn't brought up during the whole conversation.

It was understandable. This was a start-up and they were still figuring things out. He was getting paid either way, so, honestly, he didn't care much about how long it took them to get things together. The women seemed to have most things worked out, and they were obviously experienced models in their own right, so he never thought to press for a company name until now.

Was he being a bit naive? Probably. But even if they went under in a year, he would still come out with experience in the field, the very thing he lacked and suffered for in his other interviews. Since he was leading everything, he could even put down that it was manager experience as well! It was a win-win for Jack, no matter how you looked at it.

"Well...We are still thinking on it, honestly." Natasha says with a laugh, finally breaking the hug and waving for the others to follow out of the restaurant. She had left several $100 bills on the table. Enough to pay for the meals, the tip, and then some.

"Since we are only hiring models over the age of 28, we were thinking of doing something catchy and edgy pertaining to that. We want our market to be affluent businesswomen and mothers ideally. So maybe something like 'The Cougar Club?'"

Jack couldn't help it. He had been holding back so well, so far. He raises an eyebrow and smirks.

"What? Got a better idea, bub?" Hannah asks, poking his chest and getting a bit too close for comfort to Jack. She was around the same height as him, only a little shorter, and so she really got right up into his face.

"No, No! I was just thinking that it fits you all perfectly, actually." Jack admits quickly, taking a step back from her. "You three are such beautiful women, and I am sure you could get any younger man that you wanted."

The three glance at each other, before looking at him with growing smiles. 

Gwen steps up close to him next and asks in her sultry drawl, "What about you, Jack? Could we get you?"

Gulp. Yes, please. Jack would take her anytime, any place...but that was not an appropriate thing to say, and her smile told him that she was obviously teasing him.

"Ha! You couldn't handle me." He answers with an exaggerated wink and then bursts out laughing. He chooses to go with humor to get out of that potentially dangerous situation. 

"Oh! Look at you, acting like you are hot stuff now that you are one of us, huh? I like it." Natasha says, giving Gwen another meaningful look. 

"Alright, I need to take this one home before she gets sick," Gwen says, grabbing onto Hannah's shoulder.

"Hey! I'm fine! We should hit up a club!" The woman in question says, trying, and failing, to get out of Gwen's surprisingly strong grip.

"Not a chance. I only have an hour left before I turn into a pumpkin." Gwen jokes with a roll of her eyes.

"Aww...Spoilsport." Hannah pouts adorably. 

"Um...Jack?" Natasha asks, looking bashful for the first time since he had seen her.

"What's up, Nat?" Jack says moving closer to her in case she had something private to say.

"I drank a bit too much tonight...Would it be alright if I ask you to drive me home? I can pick up my car tomorrow, I just don't want to risk driving it and getting pulled over." She looks down, as if ashamed.

"Of course! That is no problem at all!" He says, putting a reassuring hand on her shoulder as he pulls out his phone to ask her for directions to her place.

Gwen grabs a cab with Hannah as Natasha is entering her address. They apparently roomed with each other temporarily while they were getting the company started. Jack waves goodbye as they leave, they wave back, and Hannah even blows him a kiss with a wink as well. He just laughs and shakes his head.

'I like them. I feel like this will be a good fit. Our personalities seem to mesh well.' He thinks with a smile as he watches them pull out of the restaurant parking lot.

"Here you go. Thanks again, Jack." Natasha pulls his attention back to her by handing him his phone.

Jack stares at the screen and has to blink and rub his eyes.

'No way. She's in the same apartment complex as me? This is nuts!'

He starts laughing, and Natasha gives him a concerned sideways look. 

"Sorry, you just live in the same complex as me, and I couldn't believe it. We run into each other here and we live at the same place too. It's like fate!" Jack says with another laugh.

He hears Natasha gasp at his words, and looks back down at her worried he said something wrong, but she is just smiling sweetly at him, so he must have heard wrong.

"That is such a funny coincidence!" She says as she looks around the parking lot. "Which one is your car?"

Jack smirks and props his arm out, offering it to his recently reconnected step-sister. "Right this way, Maddam. Your coach awaits!"

She doesn't miss a beat and links arms with him, playing along. "My, what a dashing knight I have." She flutters her eyelids at him several times and they both start laughing as he leads her to his Audi Convertible.

Natasha raises an eyebrow at the 2 seater sports car. "Holy cow, Jack! Nice car!"

"Only the best for the Maddam," Jack smirks, continuing the act.

She rolls her eyes but smiles widely all the same. He opens the door for her and she smacks his arm claiming she could have done that, but Jack keeps his smirk in place and she eventually starts giggling again as she gets in. 

Once they are in the car, Jack puts on some soft music and starts asking her questions he has been dying to ask.

"How are you doing, Nat? How have you been? Might as well take this moment to reconnect while we can." 

"Not bad, modeling was fun and lucrative, but I didn't much enjoy the lighting always being in my eyes, or the heat of the set. Not to mention some of the outfits were downright uncomfortable, but it was ultimately a very successful career...It just gets tiring, you know?"

'More than you can possibly imagine.' Jack thinks internally.

"I can't say I understand, but that does sound tiring." He responds instead.

"How about you? What have you been up to?" Natasha asks, turning fully to stare at him.

"I'm doing pretty well! It took me a while to finish school, trying to figure out what I wanted to do and all that. Dad left me enough to get by, however, so I didn't really want for much. I was just lucky like that, I guess." He answers, telling a half-truth. 

"Oh, I am sorry your dad left, Jack. I know how hard that was for Mom and me when- Ouch!" She suddenly yells out.

Jack, startled, looks over at her worriedly. "E-Everything okay?"

"Yeah...Shit. No. My bra strap broke. It's stabbing into my back...I'm sorry Jack. Could you pull over for a moment? I need to take it off."

Jack blinked. Suddenly aware of how close the two of them were. The high of success was fading, and the beautiful woman that he had an intense sexual fantasy about only days ago was asking to take her bra off while in his car.

'Okay, Jack. Cool it. This is fine. She is in pain and needs help, don't be an idiot.'

Taking a quick breath to steady himself, Jack responds, "Yea, no worries, one sec." 

Jack pulls off the road, only a mile or so away from their apartments as Natasha winces in pain from the offending wire. Once he comes to a stop, she hops out of the car, fiddles with her teal dress, and comes back in a moment later with a black lacy bra in her hands. The peaks of her nipples show through the thin fabric of her teal dress, but he does his best to ignore that. 

'Jesus. What is with this situation all of the sudden? God, she looks good...'

"Sorry again, Jack. I know this is probably inappropriate to say, but these damn things are going to be the death of me someday." She gives him an awkward laugh and a slight smile.

"It's a part of life, Nat. I am not offended in any way. I am happy to help if I can, and pulling off the road was no big deal." He smiles back and reaches over to pat her hand softly. 

Electricity seems to spark between the two at the contact, and Jack swears her nipples grew more prominent under the thin fabric. 

'Nope. Nope nope nope. She is my boss. My brand new boss and long-lost step-sister. We can't do this. No way.' He tells himself as he pries his eyes up towards her face again. 

She, luckily, didn't seem to notice his wandering gaze and, instead, is biting her lower lip, deep in contemplation about something as she looks out the window.

'God her lips are sexy - No! Fuck, Just get her home, Jack.'

"I...*Ahem* I'm gonna get us back now, alright?" He says, putting the car back into drive and not waiting for her reply.

"Okay." She says softly, still deep in thought.

They were almost home and Jack notices that she keeps rolling her shoulders and pushing on certain spots on her back with her hands and then wincing.

'Yea, I can imagine your back would hurt with those two. I don't envy you there. I do really want to play with them though...Shit. Almost home, Jack, almost home.'

The rest of the short drive was made in silence as an odd tension seems to fill the car.

Once he pulls into his parking spot in the apartment complex, Jack breaths a sigh of relief...Only for it to catch in his throat at her next words.

"Jack...You said you were willing to help me, right?"

"Um...Yeah? What's up?" He responds nervously.

"Well...It's just...Okay, I know this isn't super appropriate, but I am alone out here. Other than you, Gwen, and Hannah, I don't have anyone I can ask this..."

Feeling cautious, but not wanting to blow off her newfound trust in him, Jack responds, "Ask away, Nat. As I said, I am happy to help where I can."

"Then...Would you mind giving me a shoulder massage? I have a knot in my back that is really killing me. I haven't been sleeping well because of it...Sorry if that's too much..." She trails off, lowering her eyes to the floor.

Breathing a sigh of relief, Jack smiles widely at her. "I would be happy to, Nat. Want me to do it here?"

"No, I have some herbal ointments you can use up at my place...again if that is okay?"

"Sure...That should be fine." Jack agrees with a nod. Going up to her room wasn't the best idea, he knew, but he liked that she was relying on him. It felt new and filled him with pride.

"Okay! I will lead then. Thanks again, Jack. You're the best." She answers with a bright, relieved, smile.

Missed by Jack was the smile turning into a full-fledged shit-eating grin as Natasha turns away from him.

A short walk later and they both enter her apartment. It is a mirror of his own, 2 bedrooms, 1 bathroom, a large open living room attached to the dining room, a fairly large kitchen, and a back patio space with a sliding glass door.

The big differences are that her apartment, which is below his, is not in a loft-style, but rather a normal 2 bedroom apartment. His was more spacious since he lived on the top floor. The other difference was in the furniture. Natasha's room was, obviously, much more girly than his. Not in a teenager sense, but in the fact that everything seemed to have a woman's touch to it.

Jack's apartment was pretty bare-bones, fit more for usability and practicality than looks or style. His furniture didn't match and he still used older pieces even though he could easily have replaced them. He just didn't like to waste money where he didn't need to - Something he learned from his father's wasteful example.

"Make yourself at home, I am going to change real quick. I need to get out of these heels too." She says with a musical laugh as she disappears into the first room on his right.

Jack makes his way over to her white couch. A small coffee table sat in front of it with a multitude of fashion magazines spread out. A bottle of nail polish, some used paper towels, and a toe separator were also present, reassuring Jack that she hadn't planned this. He was really going to give her a shoulder massage then he was going to leave.

That was it. That was all that was going to happen.

'Fuck. My heart is beating like crazy. This place smells so nice...'

The sound of the door opening behind him drew his attention. Natasha walks out a second later wearing a baggy white t-shirt with a wide opening at the top so that it supported itself on her upper arms instead of around her neck. It leaves her neck and her shoulders completely exposed and makes sense for the task at hand. She has on a pair of comfy-looking pink sweatpants and wears no shoes, showing her bare feet and matching toenails to the nail polish he saw just a minute ago. Her hair is out of her usual bun, and this is the first time Jack has seen her with her hair down.

The navy blue, silky locks cascade down her back and front, looking a bit wild...As if he had undone her bun himself right before a passionate act...Two things also stand out with her outfit, and it proves that she has forgone a bra for this massage.

'Fuck.' Jack thinks as his smiling mask falls completely, his mouth slightly ajar. She wasn't just hot, she was sell-your-soul-to-the-devil levels of hot. 

Natasha moves over to the couch with a warm smile on her face, apparently not registering his look of shock, and handing him a green bottle of herbal ointment. 

She doesn't wait for him to say anything as she turns her back to him and speaks, "I am so thankful to you, Jack. You have no idea how miserable it has been the last few days." She pulls all her lovey hair to the side to give him free rein to her shoulders.

Her pale skin seems to glow in the dim light of the room, and Jack swallows a lump in his throat as he sees her perfectly biteable neck.

'I want to mark her and make her mine.' Jack thinks as he fantasizes about all the things he would like to do to her. None of them have anything to do with a shoulder massage.

"Jack?" Natasha asks, looking over her shoulder at him in worry. "Is everything alright?"

"It will be," Jack answers in a low growl, before blinking and remembering himself. "*Ahem* Yes, everything is fine. I was just...admiring how perfect your skin was. Sorry if that is weird." He admits honestly.

"Not at all..." She says with a blush and an embarrassed smile, "I'm glad you think I am beautiful, Jack. It is an important part of being a model, after all." She giggles, before giving him a questioning look. "Um...My shoulders...?"

"Right, right. Sorry." Jack responds, opening the bottle of ointment, putting some on his hands, and then rubbing them together to warm up the liquid - It was not his first time playing with oil. 

He then, gently, spreads the ointment on Natasha's bare shoulders, making sure to cover them completely, and starts to rub the oil into her skin.

"Hmmm..." Natasha hums in appreciation at the sensation, and it causes the hair on Jacks's neck to rise. 

'I need to hurry through this. I am at my limit. Anymore and...well...'

He uses his light touches to find the knots in her shoulders and back. Once he acquired his targets, he gets to work, applying firm pressure and working the knots free with circular motions from his thumb.

"Ahn!" Natasha moans at the sensation, nearly causing Jack to lose it completely. Instead, he works as hard as he can to stay in a meditative state. 

He had one task: Break the knots. He zoned everything else out. Completely ignoring the moans of pleasure Natasha was making in more and more frequent intervals. 

"S-Sorry, Jack." She says in a breathy tone, "I can't help it whenever someone gives me a massage-Ah!" 

"No. Problem," Jack says mechanically. No longer even trying to sound chipper. His face was in its natural scowl and his eyes were burning bonfires of passion, held back by the most flimsy of gates. 

10 minutes went by like this until Jack felt his work was done. 

Sighing in relief, Jack pulls his hands away and says, "I think you should be good now, Nat. I gotta go though, so I will talk to you tomor-"

"Wait! Jack...I...I know this is not something I should ask, but...Can you massage one other place?" She asks, turning to face him and grabbing his hands before he can move.

"What is it?" He demands, staring into her golden yellow eyes.

"Well...I am...I'm nearing my time of the month..." She says blinking rapidly, her face completely flushed, "And whenever that happens my...my breasts get really sore. I'm sorry for asking this, and I promise I will never ask it of you again, but you were so good with the back massage...Do you think...Would you please message them too?"

Jack's eyes bulge as they open wider than he can ever remember them being. "You...You want me...to massage...your breasts?"

"Yes, Jack, Please! I know this makes me a horrible boss...but you are the only one I can ask! I really need you right now..." She says, her eyes pleading and needy.

"Nat...I...I can't. If I touch you there..." Jack whispers, hearing his heartbeat in his head, it was pounding so hard.

"Please, Jack. I'm begging you." Natasha says, leaning forward and looking up at him with wide, innocent eyes as she bats her eyelashes.

"I really can't Nat. I am not that strong. If I do that then...I won't be able to stop myself from going further." Jack admits, feeling there was no other way to stop this train wreck from occurring than for him to be honest.

She bites her lips and looks down for a second, only to look back up to him with determination. "That's alright...I should reward you for doing this anyway..."

"Natasha! We can't-" Jack tries, his body literally shaking with the feeling of need building up within him.

She quiets him by kissing his lips softly. The sensation sends bolts of electricity through Jack's entire being, his dick responding immediately and answering the call.

Pulling away a second later, Natasha whispers, "I don't mind. I want it, Jack...I want you."

All reason leaves him. 

He doesn't care anymore. The only thing he wants is to make this bitch scream his name. 

He tried.

He tried so goddamn hard. 

But she pushed him too far, and she would have to pay the price.

"Haaaaaah. Well now, you really shouldn't have said that, Natasha."