Chapter 13 – An Unexpected Visitor
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This story always takes me the longest to write. So many hidden plots and things in the background to keep in mind. xD

Here's the next chapter! Hope you enjoy it!


Jack Richards - MC. Tech Lead for The Cougar Club, and White Mask


White Mask - Legendary Dom of the porn industry and Jack's past alter ego.


Natasha Sutherland - CEO of The Cougar Club and The Cougar Club: After Dark as well as Jack's boss and ex-step sister.


Hannah Adams - Retired runway model & Personnel and Operations Team Lead for The Cougar Club


Gwen Collins - Retired lingerie model and the Product and Venue Acquisitions Team Lead for The Cougar Club


Kimiko Nori - Jack's neighbor who somehow knows his identity


Erin Schneider - Receptionist at The Cougar Club Office


Elizabeth "Liz" Ellis - Natasha's Secretary at The Cougar Club - Rabbit Animal Mask


Noel Kingston - Modeling Director for The Cougar Club


Stacy Hensley - Jack's assistant & Tech Support Agent for The Cougar Club


The Animal Masks

Known: Rabbit = Elizabeth "Liz" Ellis

Unknown: Fox, Ocelot, Dolphin, Horse, Eagle, Monkey, Deer, Panther, Duck, Spider, Wolf, Lion, Snake, Lynx, Shark, & Blue Jay


The 4 Non-Players

Known: Gwen Collins

Unknown: 3


Chapter 13 - An Unexpected Visitor

Jack felt like shit. 

He had woken up in Natasha's bed with a killer hangover from the night before. Hours of high-intensity sexercise had left him exhausted and, Jack felt absolutely horrible for giving into his lust like that. 

Jack had rebounded with women and made the mistake of hooking up with exes before, and, wow, it always ended badly. 

He didn't particularly care about Natasha getting hurt feelings or mixed signals, but he absolutely despised himself because of doing this. 

He should have known better. He should have had more control. He shouldn't have drunk an entire fucking handle of vodka...He was always bad with liquor, it was one of the reasons he didn't drink very often. He hated the feeling of losing his faculties and that his mind was muddled. 

And, yet, last night he had drank like the world was ending. 

The way his head felt right now, it might. 

Jack decided to call out for the day and recover at home. He couldn't deal with work right now, and he was sure he looked like shit. The "Tomorrow" in his promise would have to wait until he was feeling better. 

'Now to sneak out of here before she wakes up.' He thinks and looks over at his bedmate.

...The awake bedmate that was currently smiling at him... 


"Morning~" Natasha purs as she sits up and stretches, not even trying to hide her breasts as they free themselves from her covers. 

Jack grunts and gets out of bed. He searches for his clothes so he can make a quick escape. This was the last place he wanted to be, especially sober. 

"Aw, no greeting from my needy lover? You were quite the wild beast last night. I doubt I will be able to walk straight today~" She continues in a teasing tone. 

Jack's face contorts in rage and fury...but a good measure of that was aimed internally. 

He decided to say nothing and, instead, put on his clothes and leave.

Natasha didn't try to stop him or even talk to him again as he did so, but once he was dressed and ready to go, he made the mistake of looking back at her. 

She was smiling sweetly at him and waving. 

Taking a deep breath so as to not explode on her, Jack silently fumes as he leaves her apartment and heads for his own. 

He wanted to say that it meant nothing...but it didn't. It was some of the best sex he had ever had and he remembered every moment of it. 

It was very surreal to both hate someone with all your heart and want to fuck their brains out, and Jack decided he really disliked that feeling. 

He left Natasha's apartment without another word and called Liz to let her know he wasn't feeling well. He then sent a text to let his assistant, Stacy, know as well as one into the "Team Lead" group chat with him, Natasha, Hannah, and Gwen. 

Seeing the "Feel better~!" from Natasha nearly made him cough up blood, but Jack needed to calm down and rest. He was in no shape to plot his boss's demise. 

Jack entered his apartment, stripped down where he was, - deciding he could worry about the cleanup later - and climbed in to take a quick shower. Once he was dried off, he put his phone on the charger, ignoring the other messages he received, and collapsed to his bed in only boxer briefs. 

Within seconds, Jack was asleep once more. 

* | * | *


Jack jolted awake from a deep sleep and groggily looked over to his bedside clock. It was a little after 1 pm and Jack was feeling much better than he had been this morning. 

*Knock* *Knock* *Knock* 

"Fucking hell...Go away..." Jack mumbles tiredly into his pillow as he pulls another one over his head and ears. 


Growling out his frustration, Jack throws the pillow covering his ears into the wall and stomps over to the door, not caring about his current state of dress. 

"What!?!" Jack demands as he throws the door open in nothing but his boxers. 

"Oh my, thank you for the show, Jack." A voluptuous woman with a sultry voice says in a Southern drawl.

"G-Gwen? Why are you here?" Jack asks in confusion.

Gwen, dressed in her usual white business shirt, black skirt, black stockings, and black heels stands before him. She exudes all the charm older women spent their lifetime cultivating, and no one had done it better than Gwen Collins...Her charm just happened to come in equal measure to her sex appeal.

Gwen had long, wavy lavender hair and deep, amethyst, droopy eyes that seemed to capture men's attention completely. Her chest was one of the largest Jack had ever seen and, though not as thin as she once was, she was perfectly curvy in all the right ways. 

Jack had said it once, and he would say it again. Gwen Collins was the woman the term MILF was made for. 

"I am here to take care of you, silly," Gwen answers with a smile as she raises a grocery bag in her left hand. 

Jack stared at her for a long moment. He couldn't seem to understand the situation and his headache was starting to come back with a vengeance. 

"May I come in? It is awfully muggy out here today. I tend to sweat a lot in these situations, so it is not all that pleasant." Gwen asks with a deep chuckle. 

Jack, not really sure why he was, stepped aside and let her come in. 

Gwen wasted no time and entered his apartment. She walked in, looked around, and tsked twice at the discarded clothes on the floor before walking into the kitchen and starting to take things out of her bag. 

Jack moves to his kitchen counter after closing and locking the door. His guard was up, but his head was feeling worse and worse as he stayed standing. 

"So, why are you really here? Did Natasha send you?" Jack asks in a harsh tone. 

Gwen pauses what she was doing, looks over to him with a stern expression, and chides, "No, Jack. I already told you why I was here: To take care of you. Now, either sit down or go back to lie down in your room. I will whip up something to help with the hangover here in a moment."

Jack...was at a loss for words. He knew there was something more happening here, but he had no idea how to force her to tell him. His mind was much too muddled for this plotting bullshit, so he decided that playing along was the best thing he could do for now.

Jack sat down at the kitchen counter on a stool nearby as he watched Gwen pull out several different fruits, vegetables, healthy powders and pills, and a blender. 

Gwen worked while humming a low tune, and that humming seemed to have a calming effect on Jack. The whole situation seemed...very motherly. He sensed no malice or false expectations behind it, and Gwen was completely at ease being in his apartment alone while he was sitting in just his boxers. 

In other words, Jack had no clue what was going on or what to expect. 

Right before she turned on the blender, Gwen turned to Jack and told him to cover his ears tightly. He nodded and did so as she started the blender and quickly tossed in everything she needed. After a few more seconds of blending, she stopped it, waved to him that it was alright now, and filled one of his glass cups up to the brim with the dark green liquid. 

She pushed the concoction over to him and explained that it was her family's sure-fire hangover-curing-smoothy recipe. 

"This is going to taste like you are eating grass, but, I promise, it will help." She explained as Jack looked down at the "drink" critically.

Jack gave her an incredulous look, but she matched it with a stern, again, motherly one. 

The two battled in silence as a war of stubbornness was suddenly being fought. 

'Does she really think I am dumb enough to drink this, no questions asked?' Jack wonders as he crosses his arms and raises a single eyebrow. 

Gwen scoffs, sighs, mutters out "Men," and then takes a sip from the top of the drink herself, before pushing it back over to him. "There, satisfied?"

Jack...was. He also felt a bit bad all of the sudden, but he pushed that feeling away. Being the "Good Guy" was the same as being a pushover. If Jack was confident in anything, he was confident in not being a pushover. 

He made a mistake with Natasha last night, but his anger and hatred for her still burned just as brightly. He would ruin her and enjoy doing it...

But that didn't mean that he should take that fury out on Gwen either. 

After another few seconds of a staring match, Jack was the one to sigh and give in. 

Gwen had never harmed him. In fact, she had only ever treated him with respect and was, by all accounts, overly generous to him. Several times during his few weeks at The Cougar Club, she would buy morning breakfast for her team, and she had always saved Jack a bagel, donut, or burrito. Always. She also had often come to check in on him and see if he needed anything, she would ask if he wanted anything if they went out to eat without him, and he had honestly thought of her as a good friend...before this whole nightmare had started. 

Still...even after that, she had not changed. Even with the jig being up, she still bought him breakfast yesterday and she still checked in on him in the afternoon. As if nothing had happened. As if nothing had changed. 

Jack couldn't find it in himself to blame her for what Natasha and the others had done, and there was always the chance that she genuinely was one of the 4 who had no idea what was going on. 

Plus, if she wasn't, that meant she was a rich and powerful woman who was not someone he could piss off or shun without repercussions. Jack was angry, but he wasn't stupid. Best to keep his enemies close by where he could watch them. 

So, Jack downed the drink. 

It was horrible and had the consistency of thick syrup, but he ignored his revulsion and drank it down completely. 

"Good, now let's go sit down on the couch and have a discussion while that works on your headache," Gwen says after wiping down the counter in front of her, cleaning the blender, and putting some things back into her bag. 

Jack says nothing but can immediately feel his headache start to lessen. It wasn't a fast process, but, even after only a couple of seconds, he could tell it hurt less. He says nothing else as he pushes the glass back over to her and stands to walk over to the couch. 

Gwen cleans the glass just as quickly and deftly as everything else and then washes her hands before moving over to join him. She smirks at him awkwardly standing by the couch and sits down on one end of it, indicating he should sit at the other end. 

Jack does so slowly, cautiously, making sure to keep most of his body turned towards her. 

Sighing, Gwen begins what she has to say, "Jack, I want to make you a promise. Will you listen to me?"

He raises an eyebrow again, but motions for her to continue. 

"Thank you. My promise to you is this: I will never lie to you. I may not always be able to tell you everything, but I promise that I have never and will never lie to you."

Jack nods slowly to her, not fully believing anything she has to say. It was not his way to be overly trusting, and trusting Natasha, someone he thought of as family and who would never harm him, had gotten him into this situation in the first place. He would have had to be a complete moron to take her words at face value.

Gwen smiles at Jack and continues, "With that in mind, I want to tell you a couple of things. Things I am not allowed to tell you and things that put me at great risk for telling you. Once again, I cannot explain everything, but I promise to always be honest with you."

Gwen had Jack's full attention now. If she was an Animal Mask and she gave him info on the others...? This was going to be an enormous chance for him to get ahead at his "Job."

"Firstly, I am not one of the Animal Masks. I am one of the 4 not participating in this little game, and I do not know who all the Animal Masks are."

'Shit. There goes my chance at leads...' Jack thinks dejectedly.

"Secondly, of the 4 not playing the game, I am the only one who knows the inner workings of Natasha's plan. I have been with her since the very beginning when it was still just an idea."

Jack balks at this. All trust and credibility she had with him, she just threw away. She had helped plan this? She had gotten to know him and allowed this to happen anyway!?! 

Fuck her. Fuck her and probably Hannah too. 

"I think you should leave," Jack says coldly, standing once again. 

"And I think you need an ally right now. Someone who will have your back and help you with the difficult things you are going through. In fact, being that for you is one of the only reasons I am at this company in the first place. I came here for you, Jack, just like the others. The difference is that I wanted to take care of you. To offer you a shoulder to cry on and an ear to listen to your problems. I couldn't have stopped this from happening, but I can do my best to help you in any way I am able. That is just who I am. I like to take care of others." Gwen says patiently in her sultry Southern drawl. 

"That and fuck me, right?" Jack snaps at her, his anger building. 

"I will not deny that I am open to that possibility, but that is not the reason I came here today. Nor is it the reason I am still with the company." Gwen waves his comment away easily. "Now, please, sit down and I will explain everything I can to you. Getting upset will only cause you more pain with your headache."

Jack was speechless...But he was also practical. Even if she was lying, he really could use an ally. More specifically, he could use someone in Natasha's inner circle that he could press for secrets. So, gritting his teeth and biting back a scathing reply, he sat once again. 

"Thank you. Again, I promise that everything I tell you, and everything I will ever tell you, will be honest and without deception." She says while she sits up a bit straighter. 

"I joined this company for two reasons. The first is you. I honestly wanted to take care of you more than anything else in the world. Before you ask, my children are 20 and 18 respectively, so I am not abandoning them to be with you. Also, I am divorced, so I have no prior commitments and can dedicate everything to taking care of you."

Jack wanted to laugh. He wanted to lash out at her...but he could tell from her intense and pure gaze that this was the truth. She really felt this wholeheartedly...Which begged a question.

"Why?" Jack asks in little more than a whisper. 

Gwen smiles widely. "I told you. This is who I am. I derive enjoyment from taking care of others."

Realization strikes Jack and he recoils in shock. "You're...You're a Mommy, aren't you?"

A Mommy was another BDSM kink, one that Jack had very little exposure to. It was a female Dom who liked to take care of a male or female "little" and who acted as a motherly figure in their life. It was the opposite of the Daddy/little kink that he had played in some videos years back. 

Jack was capable of being a Switch, someone who could be either a Dom or a sub, but this was mainly for when he did porn. He had done scenes with Mommy's before and, while enjoyable, they were not exactly his cup of tea. He liked being in control much more.  

"I was..." Gwen says wistfully, pulling Jack from his shocked musings, "But my husband decided to cheat and upgrade to a newer model. He left me for a 20-year-old and it was a rather messy divorce. Am I here to be a Mommy for you? No, not exactly. I simply want to take care of you, Jack. I...I know it sounds stupid, but you helped me through my divorce and it is because of you that I get to live one of my dreams."

"H-How could I have helped you...?" Jack wonders aloud. He could not think of how a pornstar could possibly have a positive impact on anyone's life. 

Gwen smiles widely at him and reaches over the couch to take his hand in both of hers. "You are much more of an inspiration than you think, Jack. To you, you may have only been a pornstar, but to grieving widows or divorcees you were a chance to feel loved again, even if only for a brief moment of fantasy. Do not underestimate how powerful of an impact that was. As for me, you pulled me out of depression and, through your aftercare scenes, showed me what being in a good Dom/little relationship could be like. You gave me hope for the future from a, seemingly, hopeless position. You made me want to keep living."

The power and genuine feelings of gratitude in Gwen's words shocked Jack to the core. Never in his life had he felt proud of the 5 years he had spent as a man whore...but she made it seem so beautiful...Like, maybe, it hadn't been a waste of his life. 

Jack shakes his head and focuses back on the situation at hand. Gwen did not remove her hands from his, however.

"I am not going to be your little," Jack says resolutely.

"And I never asked you to, now did I?" Gwen responds back instantly with a teasing smirk.

Jack opens and then shuts his mouth. She had him there. 

"My time as a Mommy ended with my divorce from my husband. With you, I want to be a caregiver, friend, and confidant. I can't promise that I will get nothing out of it myself, but one of my only goals, while I am here, is to be someone you can talk to, vent to, and rely on. I mean that from the bottom of my heart."

"What are your other goals?" Jack challenges, choosing a different angle of attack. 

Gwen chuckles in her seductive manner, "There is only one other goal. The second reason I joined this company. It has always been my dream to open my own modeling agency, and, with the talents and beauties we were able to bring on, I know this one will be successful." She explains with a wide, happy smile.

"Those are your only reasons? To take care of me and to enjoy the success the new business brings?" Jack asks with a blank expression.

He was laying a trap to catch her lying. He needed...needed to be right about her. He had to know she was just like the others. He wasn't sure why, but it felt important to him. 

"Yes, Jack, those are the only reasons." Gwen nods, finally taking her hands back. 

"And you want to be on my side with all this?" He questions again.

"Yes, I very much want to be someone you can rely on. I want to be someone you can trust to take care of you." She answers without hesitation. 

"So, you agree that Natasha was wrong to put me in this situation?" Jack questions one last time, fighting the smile he felt growing. 

"No, Jack. I agree with Natasha. I may not agree with the methods she used, but I do think you need to accept your past and stop trying to run away from it. It isn't healthy for you." She answers just as quickly, without even pausing to think. 

Jack falters. 

He was expecting her to lie. He wanted her to take his side completely so that he could know without a doubt that she was a liar. That what she said and did could not be trusted...but, instead...She had told the truth, even at the expense of all the trust and goodwill she had built with him thus far. 

He wanted to be angry. He wanted to lash out at her. He wanted to kick her out of his apartment and tell her never to return...

But he didn't. 

She hadn't lied to him. 

She told him something that would damage their relationship immediately and with absolute conviction. 

And if she wasn't going to lie to him...she was useful. More useful as a "friend" than as an enemy. 

Jack sighs and collapses back on his couch completely. 

'It's like I am constantly in a den of cobras...' He thinks as he rubs his temples. 

It was true that trusting no one and doing everything himself was safer...but he was still human. 

He wasn't a machine without feelings or emotions, and he agreed that having someone to vent to was a good thing. 

If nothing else, it might prevent him from getting drunk and winding up at Natasha's door late at night again. If that was all Gwen did, then Jack would be thankful. 

"Come here, I'll rub your head." Gwen offers with a warm smile as she pats her lap. 

Jack squints at her like she is crazy, but, after she just smiles at him sweetly for several minutes in response, he groans and moves over to put his throbbing head on her lap. 

Gwen immediately starts running her fingers through his hair and massaging his head as she coos out, "That's it. Let me take care of you, Jack. You've done so well. Natasha was quite panicked when you found a mask on your first day. You are so incredible, Jack."

Jack, whose eyes had closed in bliss, cracks one open again and asks, "...Yeah?"

"Oh, yes. You should have seen her face. It was hilarious. She is so cute when she is flustered, don't you think?" Gwen answers as she starts to trail her long nails gently across his scalp. 

'Fuck, that feels good.' Jack sighs contentedly as he closes his eyes once more. 

"I got her good," Jack mumbles out tiredly.

"You did. I bet you are going to give it to Liz just as good."

"Damn right I am. I am going to get them addicted to my dick."

"I am sure that won't take long." Gwen chuckles softly. 

"I need to make them pay..." Jack whispers softly, his mind starting to drift off.

"And I will be here for you no matter what happens." Gwen offers, just as softly. 

"Why are to me...?" 

"Because I love you, Jack. I love you and want to take care of you."

"You...hardly...know..." Jack trails off as sleep overtakes him.

"I hope to fix that, Jack. I want to know everything about you...I want to be here for you, forever."

And as the day slowly turned to night, Gwen remained on the couch, stroking Jack's hair gently as she occasionally whispered positive and loving remarks. 

Despite Jack's best efforts, Gwen had won a place in his heart this day.