Doctor Cougar

Gracie is feeling conflicted about what to do. The 44 years old doctor is pretty, being much more beautiful than many younger women. She is very gorgeous for her age and would even give several 18 years olds girls a run for their money with regards to physical appearance. Not to mention that she is remarkably intelligent, given that she graduated from Johns Hopkins medical school. Her good status as a highly respected pediatrician and high income affords her everything she has ever wanted but one thing. Well, person really. A person who means a lot to her, more so than anyone else. Someone who she wants to be with.

His name is Penn. There are three huge problems for her though. The first one is that he is 18 years old, being more than 20 years younger than her. Heck, she was able to drink legally before he was even born. Second, Gracie is close friends with his mom. And the biggest issue of all is that he used to be one of her patients. She watched him grow up not only as an adult figure in his life but as his pediatrician. This sort of past between them would make them dating inappropriate. If her colleagues found out, her job might be compromised. She could maybe even get fired if she's unlucky enough.

But her love for Penn is so strong and she couldn't fight it anymore. She has greatly struggled to control her feelings for some time now, but it is no longer possible for her to do so. The doctor is now really desperate, dying to have her friend's nerdy son in her arms. For him she is willing to take the risks. Penn is worth it to her. He is cute, kind, sweet and the way he looks at her just melts her heart. Gracie could always feel her lace panties get moist whenever Penn is around her and always has to go finger herself right after he leaves the house. It has been this way for some time now.

That's why she finally decides to call her friend Carole, who is Penn's mom. She asks her if she would mind sending Penn over so that he could help her out with some chores. Carole has no idea that her friend is in love with the boy and happily said yes. Gracie rubs her cunt through her panties thinking of how she is going to make a move on him once he is here. She can't wait to fuck him. Penn will be hers before he knows it. That much Gracie is sure of. All she has to do be aggressive with him and overwhelm him with seduction. He won't know what to do about it at all.

Carole drops Penn off soon after that. The boy is a thin bookworm. Most girls don't see him as someone they want to date, usually either ignoring or friend zoning him. There's been a few who thought he's cute but never made a move. "Hi, Dr Philips!" he greets her with a bright smile on his face. It is a very infectious smile and she finds herself grinning right back at him. He is so cute in her eyes and she wants him so badly. In times like these she no longer pays any attention to the fact that he's both her friend's son and her former patient, and that dating him could easily be seen as inappropriate. She doesn't care about the gross factor anymore. "What did you need my help with?"

The blonde pediatrician smiles at him warmly, making Penn blush. "Firstly, there is no longer any need for you to call me Dr. Philips now, Penn. You're no longer my patient," she says. When he frowns at this, she tells Penn "You can just call me Gracie." The boy nods slowly, his cheeks tinged red. "I want you to help me do my laundries and wash some dishes for me. Then you can also wash my car. Can you do that for me, Penn?" Penny quickly nods, getting to work straight away. The young nerd starts working on the chores in that order and Gracie watches him closely, not taking her eyes off him for a second as he works.

It is part of an elaborate process which Gracie is planning to use to prepare the boy for his part in her life. He used to be her friend's son and her patient but she wants him to be more than that. Gracie wants him to marry her one day and then be her subservient husband. All that would require her to train him in doing all the necessary house works. He has no idea why she is making him do all this stuff yet. One day he will but not today. No, for now, she will keep on training the boy without his knowledge, until Penn is sufficiently ready for what she has in mind.

But then her pussy throbs and Gracie realizes she can't wait any longer. She walks up to the teen from behind and places her hands on his shoulders. The much older woman leans in and sniffs his hair. He freezes in surprise but does not move away, being quite perplexed by what's going on. "So," Gracie starts to whisper as she begins massaging his shoulders. "Are you close to being done with the chores I set for you?" Feeling Gracie's warm breath tickling his skin is making Penn turn red. The way she is touching him and sniffing his hair also makes him blush too.

"Oh, yes, I think that I'm nearly done now," he mutters under his breath as his cheeks turn redder and redder. She rubs the tip of her nose along his scalp and nuzzles across to behind his ear as he stands there. Penn is rooted to the spot with his legs refusing to obey his orders and keeping him in place, just not listening to him as he tries to Will them to carry him away. "What's going on Gracie?" Penn asks her as she keeps on sniffing him and touching his body. "And why are you sniffing my hair like that?" The contact is starting to turn him on but he doesn't say that, being way too embarrassed.

"Do you have a girlfriend, Penn?" she asks him. When he shakes his head to tell her no, she smirks and then reaches around his body from behind. The sexy doctor places her hand on her former patient's crotch. She grabs his erection through the pants, fondling the geek through his trousers. He gasps as she also uses her other hand to grope him, cupping his balls from behind as Penn continues to remain there, paralyzed with shock. "Good. That means I won't have to feel guilty when fucking you. I didn't want to steal another woman's guy and now I won't have to do that."

Penn struggles weakly in her arms but she holds on fast to him. With both of her hands on his private parts, Gracie knows he won't be able to escape from her and doesn't even bother tensing up her arms, staying relaxed. "Gracie, you are very beautiful, smart and kind," the boy tells his former doctor, making her smile. "But you're also my mom's close friend. If we start dating, then both of us would be best betraying her. I love my mother and I know she means a lot to you as well. The two of you went to high school together. Please, you can't betray her by dating me. Don't let me ruin your wonderful friendship."

Gracie sighs before releasing his cock and balls. "Okay," she says. "But whar if I talk to your mom first?" Penn turns around at this part, looking curious. "I mean, what if I ask her if she is okay with the two of us going out?" The way she said this really makes him start to chuckle lightly. "I'm serious. I think I can persuade her to be okay about the two of us going out together. In that case you will be okay about it, right?" Her hopeful face melts his heart and he slowly nods, despite knowing that he really shouldn't be so okay with this. Penn just couldn't help himself.

"I'll date you if mom says that it's fine," he tells his former pediatrician, making her squeal in joy. She then leans in to kiss him on the cheek and drive the boy home. On the way, Gracie asks him not to tell his mom about what happened. Gracie insists that she will deal with the issue herself and that hearing about it too much may impact Carole's decision. After checking to see that Carole isn't home now, she goes back to her car and calls her friend. She thinks about how Penn blushed when she kissed him on the cheek and feels her pussy getting really wet. Just getting to kiss him in the most innocent of ways was a turn on for her.

Carole picks up after about ten seconds and asks "What is it, Gracie? Is it my son? Did he break something?" They all know that Penn is a good kid but he is also clumsy and has broken a few stuff before, so that's the mean concern. The good doctor quickly assures her that it isn't the case, making Carole sigh in relief. "What is it then? No that I don't like talking to you but I'm at work right now and you know what my boss is like so please just get to the point." Gracie feels nervous about what she is going to tell Carole next and decides she will do it as slowly as she possibly could.

"You see, I have something I need your advice about," Gracie begins. Carole is quiet for a few seconds before telling her to go on. "I want to go out with this guy but he's a bit younger than I am. I don't know how to win him over. Could you help me figure it out?" Carole goes silent as she thinks about what her best friend just told her. She never thought of Gracie as the type of woman to want to go after younger guys. But here she is, telling her that herself. It is all too astounding to her and she is struggling to process it. And Gracie hasn't even gotten to the craziest part yet.

"Well, I suppose you would have to be a lot more careful when flirting with him than you would be if you were hitting on a guy our age," Carole finally says to her. "Make sure not to spook him out when you approach him. You wouldn't want to scare him off and make him run away, right?" Gracie answers that she wouldn't want that. "So tread very carefully. No sudden movements, or he will panic." Gracie thanks her for her suggestion. "No problem, my friend. So may I ask who this lucky guy is? Is he someone I know?" Now here comes the difficult part Grace has been dreading.

Gracie takes a very long breath before replying "Yes, he is someone you know. In fact, you know him very well. Better than anyone, really." She pauses for a moment before continuing "He is your son Penn. I'm in love with your son and I really want to go out with him. I want a real relationship with your son and I also want you to approve of this too. It would mean so much to us. I would be really happy if I get to be with him and he would be so happy as well. Don't you want us to be happy, Carole? Please say something." Gracie then waits for the outburst she could already sense over the phone, knowing it's coming soon.

"How the fuck did you think I would be okay with this? He is my son! Mine' I'm not going to let you date him. You are as old as I am and I'm his mother! You are more than double his age. You were able to drink alcohol before he was born! You helped babysit him when he was little. You were his pediatrician for crying out loud!"

She goes on for more than an hour and by the end, Gracie has gotten an earful.

......

After getting chewed out be her livid best friend, Gracie gets home. She feels hopeless about her future. She already has the perfect career with a lot of money and a lovely house. Now all she needs is for Penn to move in with her and be her husband, but with Carole's disapproval, that will be hard to achieve. Penn seemed pretty adamant when he insisted on his mom being okay with the two of them dating and now she knows why. When Carole shouted at her, it made her feel guilty for even thinking of doing that to her friend. Dating her friend's son could be terrible for their friendship and mess things up beyond repair.

Yet Gracie also couldn't deny herself a chance to be with the boy she loves. It's too hard. She isn't strong enough. But how is she going to get him to date her if he would only do so should his mom approve, and his mom clearly does not approve? She doesn't think she could do a thing to change Carole's mind now so she will have to change Penn's mind. But then that seems about just as hard, since he really doesn't want to hurt his mom's feelings. Gracie can see why he wouldn't want to, since he is Carole's son, after all. No good son would want to hurt his mother's feelings.

Then Gracie gets an idea. It's a brilliant one. She really thinks it might work too if she could control her poker face well enough. Knowing that Carole is at work now, she gets into her Porsche, driving to her friend's house. She knows that Carole wouldn't be home for at least an hour if not two, she plans to make her move and get Penn to agree to be hers. All she has to do is tell him one massive lie and she can do that. Gracie is a great liar when she needs to be one, and that is what she needs right now. She will tell him the biggest lie of her life and he will believe her words because deep, deep down, the nerd really wants to.

When he sees her, Penn is surprised by her presence. She did only drop him off back here about two hours ago and now she is back. Not that he isn't happy to see her. He really is quite happy to see Gracie, since she is both a family friend and his former pediatrician, but after she asked him out, Penn still feels quite awkward in her presence. "Gracie, what are you doing here?" he asks her in the most polite tone. He feels unsettled by how ill at ease she appears, but a part of Penn is also secretly aroused by the raw confidence she is exuding from her stance. He doesn't know why but he is.

"I talked to your mother on the phone," she replies. Penn tenses up. Disbelief is plain across his face. The boy couldn't believe she actually went through with asking his mother if she would be fine with the two of them dating. "She was a bit upset at first. Okay, maybe she was more than a bit upset. But then I told her about how much you mean to me and how much I love you. She took a lot of convincing but now she's okay with the two of us dating. So you will keep your word and go out with me now, right? You said you would date me if your mom is fine with it and she is fine with it now."

Now Penn is totally flabbergasted by what he is hearing from her. He blinks several times before managing "That is great news! Yes! I'll do it. I'll keep my word." Penn could feel himself turning red all over. He could hardly believe he would be going out with Gracie. She is such a kind, intelligent and beautiful woman. He is so lucky she asked him out and he knows it. What he does not know is that she lied about his mother being okay with the two of them having a relationship. He doesn't suspect her of deceiving at all, so great is the nerdy boy's naïveté. The thought that Gracie lied so she could get him to be hers has not crossed his mind.

"Good," Gracie tells Penn. She kisses him on the lips and he gasps in surprise before kissing him back. He goes weak in the knees as she wraps her muscular arms around him. Gracie's embrace is able to bring him warmth like nothing else ever did. She then says "I want to take you out to dinner tonight. But you can't tell your mom yet though. In fact I don't want you to talk to her about us at all. She might have accepted us now but she still feels uncomfortable about this. So it's best not to remind her of our relationship for now, alright? Just promise me you won't mention it."

Penn might have gotten suspicion of her if he was a more wary person but he is a very trusting person so he nods in agreement to her. He believes Gracie and takes her at her word, much to her delight. The boy doesn't even suspect that she lied to him about his mother being okay with the two of them dating. "Okay," he says. "I won't talk to mom about us dating. I'll let her have time to adjust to it first." Gracie nods, thanking him. She will have to tell Carole later about their relationship after Penn has gotten much more serious about their relationship. She'll have to wait for a bit of time.

"I'll tell her I'm studying at a friend's house," he tells Gracie before she leaves and after she asks him to come up with an excuse he thinks will convince his mom to let him stay out late. Gracie has told him where she'll pick him up and he is surprised by how excited he is. He was already excited the moment that he heard his mother approves but now his excitement level is through the roof. She is the type of woman he wants to date and now he's going to dinner with her. The fact that she babysat him and was his pediatrician is now at the back of his mind and no longer of concern to him.

He goes back to his bedroom where he sits down on his bed. There he plays on his phone for a few minutes before he goes down to the kitchen. Penn starts to cook his mom light dinner before wrapping it up and sticking the plate in the fridge. The boy then writes a note and sticks in on the fridge door, waiting to see if his mother would come home before he has to leave. He sits on the couch and watches TV for another two hours before looking at the time and seeing that he has to leave. Penn gets up from the couch and leaves home in a hurry, going over to the place where his mom's friend said she'd pick it up.

Soon after he arrives at the place, Penn is greeted by Gracie. She gives the boy a quick peck on the lips. Leading him to her car, she opens the door, letting him into the shotgun seat. He puts on the seatbelt and she gets behind the wheel. Then Gracie starts the car and turns to face him. "There's a nice little French restaurant nearby," she tells her young date. "The Foie Gras Ravioli there is a very delicious dish." She then drives to the restaurant. He looks at her out of the corner of his eye and blushes when she catches him watching her. Gracie is delighted by his reaction, finding him to be very cute when he turns scarlet.

She gets them there in half an hour and parks the car. The restaurant is a nice, small one like she promised. Inside it, there are a few chandeliers and carpets made from the finest fur. Penn feels so overwhelmed by it, having never dined in such a beautiful place before. Gracie happens to have a regular table where she and her younger partner are soon being seated by the beautiful waitress. He blushes as she reaches across the table to hold his hands in hers. Gracie has soft yet strong hands. They are very delicate yet still powerful from lifting weights, the result of which are her two powerful arms. "I told you it's a nice place," she says.

He listens to her tell him stories about when she and his mom were in school together. The boy laughs as she recalls all the shenanigans that they got up to. Penn never knew his mother and all her friends were pranksters back in the day. "I've got to say I wasn't sure about the date when you first asked me out," he admits to her. She looks confused so he explains "You're really great but I was worried that you being my mom's friend might complicate things. Plus, you were also my pediatrician. But now I realize I made the right choice when I said yes. I'm glad we're doing this now. I really like you a lot, Gracie."

"I like you a lot too, baby," she replies. It isn't the truth. She doesn't like Penn. Gracie Philips is unconditionally and irrevocably in love with him. It's just a bit too soon to tell him that, since Penn could easily panic and freak out. If he leaves her it would break the doctor so much, so she is going to be careful with him. "Come on. The waitress is coming over with our appetizers now." He nods and the two of them start eating their meal together. The atmosphere is just perfect, being very romantic with all the candles. It's all they could ask for.

"This is really good!" he remarks to her as he starts eating the scallops. Gracie sits there and smiles at him. She knows she made the right choice to bring him to this restaurant. For herself, she has ordered an onion soup as appetizer. It doesn't take long before they finish the appetizers. About 20 minutes later the main dish arrives. Both has ordered the Foie Gras Ravioli and it proves to be as great as Gracie promised Penn it would be. They eagerly eat it and and order the desserts right after, a tiramisu cake for Gracie and Crepe Suzette for Penn. The young boy is still really enjoying the experience of being on a date with Gracie.