Chapter 17

Things are becoming intense for Alan as the days progress. He feels that he has been doing some good, helping out Marian next door with her troubles. She came over to thank him and offer herself as a means of a thank you. Of course he fucked her, he’s not stupid.

Sandy has been trying to get closer. She seems to have made it a point to watch Alan fuck the women he brings home. She has been there to help him masturbate by licking his prick or balls. She has even ensured that he is cleaned up afterward real good. Sometimes it is so good he ejaculates a second time without having to even touch himself.

And then there is Judy at work. She has gone above and beyond to please him. She has come to work every day with a dildo shoved up her. She tells him that it is for him, but in reality it is for Victoria, her girlfriend. What Alan doesn’t know won’t hurt him, right?

So while he is helping women in need, Alan has to deal with the strangeness of his dog and his enjoyment of her, while trying to figure out how to take the next step with his secretary. Alan figures that by fucking all the women he does, he is helping them in some way like for them discovering who they are. He is at odds with himself over Sandy and how good she can make him feel. And then there is Judy that seems like she wants to give her all to him, yet at the same time she is so elusive. Because of all this weight on his shoulders, he cuts out of work early, skipping out on a blowjob and potential sex with Judy to see Kennedy. Even if he misses out with his secretary his therapist will take care of him.

“You’re too stressed,” Kennedy says. He has told her everything that has happened since the last time he saw her—everything that is except his forays with his dog. “You have a good woman that’s practically yours. She seems to take care of you like your mother did.”

“She makes sure everything runs smoothly at the office,” he agrees. “Maybe if I had her at home with me I wouldn’t have to fuck so many women.”

Kennedy smiles at this. “And do you hate fucking so many women?” she asks.

A grin spreads across his face. “I can’t say I hate doing it, but I don’t think I would if I had her.”

“It is interesting how a man can go monogamous once he finds the woman he loves,” Kennedy continues. “But I wonder if you will stay that way.”

“Why wouldn’t I?” he asks.

“You’ve lived your life like it is an adventure,” the therapist explains. “It is like suddenly quitting that adventure to become a scholar. The call of the wild is a confliction with having to sit in library. It is always beckoning and eventually you have to answer or die from boredom.”

“And you doubt I can do that?” he asks.

The woman nods. “I think so.”

“How would you feel if we didn’t have our meetings?”

“I think we still need them even if everything works out,” she answers. “I would like to feel that you don’t need me anymore before discontinuing.”

“That would be hard if we’re still fucking,” he says with a cocky grin.

Kennedy doesn’t return the smile. “We wouldn’t be,” she says and his grin fades away. “If would be strictly professional—doctor and patient.”

“Oh ... well...”

“As a matter of fact, I have a little assignment,” she goes on, “Two actually.”

“I don’t think I need more on my plate right now,” he tries to argue.

“These are easy,” she says quickly. “The first is for you to go on some little getaway.”

“By myself?” he asks.

“Take Judy with you,” Kennedy suggests. “In fact, have her invite her girlfriend along. Maybe get a threesome happening. Let Judy get a taste of your lifestyle. She will not like it and let you know or she will and dump her girlfriend.”

“What if she isn’t interested at all?” he asks. “What makes you sure she’ll dump Victoria?”

“If she is as into you as you believe, she’ll tell you her feelings. But from what you have told me, she is kinky and is enjoying this side of her that you’ve opened up.” Kennedy smiles as she sits forward in the chair. “As far as her dumping Victoria, that’s easy. Victoria doesn’t seem to be keen on doing much outside her comfort zone. That fact that she has only agreed with letting Judy give you blowjobs is because she enjoys the benefits that come with it.”

“Judy’s high salary,” he surmises.

“She’s over paid for her qualifications,” the therapist specifies.

“And the other assignment?” he asks with a nod.

“You’re going to leave here today without fucking me,” she says. “Not only that, but I want you to resist picking up any women until after your getaway.”

“That shouldn’t be hard,” Alan puffs.

“Shouldn’t it?”

By the time Alan leaves Kennedy’s office it has begun to rain. He rushes to his car and gets in. His assignments are now heavy on his mind. They shouldn’t be hard to follow, though now he wishes he would have gotten at least a blowjob from Judy. He thinks about going back to the office to maybe get that blowjob and then decides against it. He didn’t expect this, but at least if he has to wait until this weekend, he can. Besides, there is Sandy at home that can help alleviate the ache in his loins. She isn’t human, so she doesn’t count. Even if she somehow did count, he’s not picking her up, she lives with him.

Heading home Alan rounds a corner and notices a woman walking, huddled in her coat with her head down. Of course his first thoughts go to the potential of having sex with her, but then he remembers his assignment. He passes her and just happens to look back through his rear view to see the car that just passed him fly through a puddle beside her and send a wave of water cascading over her like a tsunami on a little island.

He stops at the stop sign, his eyes still on her. She stands still now. She is shivering. Wearing a thin jacket, her hair is plastered on her face and shoulders. Forgetting his need for sex, he feels a sense of duty to help her instead. Seeing that there are no cars coming or going, he shifts into reverse and backs up to her. When he gets to her he rolls his window down and shouts, “Hey, you want a ride? It’s cold.” She nods and he motions to the passenger side door. “Jump in then.”

The woman wastes no time and as she closes the door, she huddles nears the vents where the heat is blaring for her. “Thanks,” she says. “You’re a lifesaver.”

Alan smiles at her and starts back down the road. “I’m Alan Denning,” he says. “Where you headed?”

“I’m Cathleen. I live across town over in Uptown Apartments.” She pushes the hair from her face. “Today turned out to be real shitty.”

“I know where that is,” he says. “And yeah, you’re right it has become a shitty day.”

“The rain?” she asks.

He shakes his head. “That I can deal with, it’s work that’s a pain in the ass.”

“Boss troubles?”

“I am the boss,” he chuckles.

“I know that feeling,” she says. “I used to run my own company, took too much out of me. So I went back to working for someone.”

“I never liked making someone else money,” he remarks. “So how long have you been walking anyway?”

“Quite a bit actually,” she says, shaking her head. “My car’s in the shop so I’ve been taking the city bus. I missed it by like four minutes and I didn’t want to wait until it came back around.”

“Yeah that hour between routes is crap,” Alan says with a shake of his own head. “I’m one of the businesses that have pushed for the city to get the bus system updated. Those assholes on the commission are just way too slow.”

“I never gave it much thought before I need to use it,” Cathleen admits.

“I didn’t either, but I heard some of my employees talking about it and I figured I would see what I could do to help them out.”

“That’s real nice of you,” she says. “Not many bosses would go that far to stick their necks out for their employees.”

“It’s the least I can do,” he says. “I mean, we’re supposed to help out of fellow men and women, right?”

“That is true,” she agrees.

He pulls into the apartment complex and asks, “Which one are you in?”

“It’s right there on the corner, top floor,” she answers, pointing in the direction of her apartment. “Thank you so much, Alan Denning.”

He pulls into a parking space. “It’s no problem. I hope your day turns out better.”

“Same to you,” she says, giving him a quick smile. Then she opens the door and slips out.

Alan watches her as she begins to climb the stairs. I did it! He has managed to avoid temptation and woo the woman. Kennedy obviously didn’t think it was possible, but he did it. Then Cathleen slips. He actually sees the heel of her shoe snap. Quickly, he turns off the car and runs out to her. “Are you okay?”

Cathleen is holding her ankle tightly and tears are rolling down her cheeks as she shakes her head. “This day has just gotten shittier.”

“Let me help you,” he says as he slips his arms beneath her and lifts her up. She cries against his shoulder as they get to the second floor out of the rain. She fumbles with the keys before being able to get them in the knob of the door and he carries her inside. Alan takes her to the couch and sits her down. “Let me take a look at that ankle for you.”

Cathleen sits back and extends her leg. “Oh fuck. I’m so sorry. Thank you so much.”

Alan shakes his head as he looks at her ankle. It is slightly swollen, but not too bad. “There’s no need to apologize. I’m here to help. It’ll be okay. Just get some rest and ice.”

“No, you’re a nice man,” she says. “You care about your employees, and you care about stranger, helpless women.”

He looks up and gives her a smile. For the first time he realizes how pretty she is. He was so focused on his assignment, trying to prove his therapist wrong, that he didn’t pay all that much attention to Cathleen’s looks. Now looking at her face, doe eyed and tear stained cheeks, none of it fazes him.

She smiles up at him and asks, “Can I at lease get you a drink for your troubles?”

He thinks about it for a moment and says, “Why the hell not? I’ve taken the rest of the day off anyway.”

Cathleen smiles and stands awkwardly. “I only have beer, if that’s alright.”

Alan nods, “That’s perfect.”

The woman attempts to walk but stumbles. He jumps up and sits her back on the couch. “How about I get you an ice pack instead?”

She sighs, “It’s probably the best thing to do, yeah? I still owe you that beer. How about I buy you one as soon as I heal?”

“You got yourself a deal,” he says. “Now let me get that ice pack for you.”

He can see the kitchen from the living room and heads to the freezer. He grabs the cold pack.

Taking it to her, he says, “This is going to be cold.”

The woman jumps a little as he places it on her, “Holy shit!”

“Sorry!” Alan laughs. “You should get on some dry clothes and get some rest.”

She takes a deep breath. “Do you think you can do me two more favors?”

He shrugs. “Sure, what do you need?”

“Can you help me with my coat and help me to my bedroom?”

The man sees no harm in helping a bit more. He has fought his urge to pursue any women until this weekend and he has forgotten his need. He nods and helps her stand. Then her removes her jacket, fighting for every inch. Then she leans on him as they head toward her bedroom.

Her room is immaculate. A large window is framed with white curtains. Her bed is massive and covered with a thick, pink comforter. There is a large television hanging on the wall opposite. It’s clear she spends more time in the bedroom than anywhere else considering how sparse the rest of the apartment looks.

Cathleen’s words shake him out of his daze. “If you could just help me to the dresser I should be good. Thank you so much.”

They move together in unison to the dresser. She leans on the top of it and slides the drawer open. Although he tries to resist from doing so, he feels his eyes bulge slightly as he sees the pink dildo shaped like a dog cock resting atop a pair of satin panties. She closes the drawer quickly and her face reddens as she says, “Um ... sorry. You didn’t see that, did you?”