Gracie is feeling conflicted about what to do. The 34 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 15 years younger than her. 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.
She then pays the bill. Gracie drives a bit slower when they leave as it is now getting dark outside. The woman drops him off a couple of blocks away from his home so his mom wouldn't see him with her and find out what had really happened. She needs some more time to make him head over heels in love with her and unable to walk away from her. The good doctor gives him a little goodnight kiss before he exits the car, telling him "I'll see you at my house again tomorrow," she says. "I will tell your mom I have some more chores for you to do."
"Okay, Gracie," he tells her before he starts walking to his house. When Penn reaches home, he enters. His mother is waiting for him. She doesn't know who he was really with and just asks him if he and his friend really worked or just played games together. "Of course the two of us really worked, mom," he tells her and quickly goes to take a shower and brush his teeth. Penn has already eaten more than enough for the night.
As he lies in bed, he looks up at the ceiling with his hands clasped behind his head. The boy grins to himself and thinks about just how lucky he is to have a wonderful girlfriend like Gracie.
....
Penn is feeling pretty good about how his relationship with Gracie is going. It has now been an entire week since the two went out for the first time. Gracie has consistently remained her usual charming self and he still feels that he could be himself fully around her. All he looks forward each day now is to go on another date with her. He does not find the fact that she was his doctor to be a source of discomfort anymore and now allows himself to enjoy being with her fully. For the boy, there is no more feeling uncomfortable around his older girlfriend, and she knows and is happy about how he feels too.
He is sitting on her couch right now, watching TV with her. The dork could feel her eyes on him though. Penn just turns slightly to face her and asks "Are you thinking about something?" She is caught off guard by this. Gracie looks at him as he continues "I just noticed that you have been looking at me out of the corner of your eye for some time now. Is everything okay?" Penn is genuinely concerned, wondering if something is wrong or not. The young boy might feel comfortable dating her now but this is still his first relationship, so he can get nervous at times like this.
Gracie leans in to kiss him gently on his temple, making the boy blush. "I was thinking about doing something when I was looking at you," Gracie says to her cute boyfriend. Penn has no idea what she is talking about. He doesn't ask her though, instead choosing to wait. If she wants to talk about it then she will. He shouldn't press her on it if Gracie isn't voluntarily offering any information on it though. He'll let her decide by herself if she wants to talk about this or not, without him pressuring her. "It's really important. Do you want to know about it, baby boy?" she asks, using her pet name for him.
Penn blushes from her words. His ears turn bright red as he looks away from her coyly. The boy always get so damn flustered whenever she calls him that. She loves seeing his cute reaction and is using the endearing words more and more often each passing day, just so she could see Penn look like a tomato. "Sure," Penn whispers, with his voice now slightly trembling. "What were you thinking about doing?" Somehow Penn gets the feeling that he shouldn't have asked her the question that way but he doesn't know why yet. He is about to soon enough though, when she gives a mischievous little smirk.
"I'm planning to do you, actually," she tells her much younger boyfriend as he sits there in shock. She then places her right hand on his crotch. Her fingers start rubbing the boy's dick through his pants. Gracie massages his now rapidly growing erection, making him gasp as she caresses him through the trousers. Penn tries to push her hand away in his surprise, overwhelmed by what is going on right now. She hasn't touched him down there yet. It's the first time and he doesn't know what to do as Gracie beings stroking his prick through his pants. "I'm going to jerk you off and then suck your dick, and when you are ready, I'll stick your cock inside my cunt. I'm going to make you cum in my pussy."
"Gracie, wait just a moment," he says to her as she starts to unzip his pants. Try as he might, he couldn't stop her from yanking his trousers down to his ankles and touching his boxers. The material is very thin and his pre cum is already seeping through it. She could see the outline of his dick clearly and licks her lips, stroking it. Gracie resumes with her pumping motion as she jerks him off through the underwear and gives the cock several squeezes, making Penn moan. "Please, let's talk about this first before we do anything. I really like you a lot but I'm worried we're taking it too fast. I don't want to mess up what we have, baby," he says to her as she plays with his penis.
"Okay, baby. I will take things slow, but only because I like you so much," she replies. "I won't rape you because I care about your feelings. You don't have to fuck my pussy today. But you must let me suck your cock. I want to drink your cum." He gulps as she caresses his stiff prick and yanks his boxers down like she did with his trousers. Penn's dick springs free, jutting up. She smiles and wraps her fingers around it. With a very firm grip of her hand, she strokes his dick, sliding her fist up and down. "Your dick is mine and I am going to suck it today, baby boy," she whispers as she masturbates his dick.
Gracie spits on his dick, using her own saliva as lubricant. I'm yours," he tells her, crying out as she swipes her thumb across the spot beneath his cock head. Penn's underside is very sensitive. The frenulum has so many nerve centers clustered right there, after all. "Just no sex today please. I don't feel ready yet. Ahhh! Oooh, your hand feels so good." She smirks, tugging his dick harder. The older woman enjoys her control over him, knowing that Penn is still a complete virgin, whilst she is already a very sexually experienced woman. He is no match for her and she loves that. She loves the power it gives her over him.
"It's okay, baby," Gracie says, jerking his dick harder. She palms his balls and rubs them, cupping his nutsack gently. Her skilled hand squeezes him and she pumps his erection. Gracie kisses him on the side of his neck, licking him and nuzzling with the tip of her nose. Penn is now moaning louder as she strokes him. She says "You are so cute trying not to cum. Don't worry. I know what I'm doing. I won't let you cum until you are in my mouth. I'll make you blast the inside of my mouth with your warm jizz. I bet your virgin cum would taste really nice, baby boy. I bet it will be real delicious."
Gracie then bends down and wraps her lips around the spongy head of his dick. She then slides her full lips down to the base of his cock. Her pouty lips feel so good around him and she sucks him off slowly. The older woman usually likes to give aggressive blowjobs but with her partner being inexperienced, she is worried he would lose control and cum too fast. That's why she is being careful, wanting to build up a massive load in his balls so that he'd cum a lot. Gracie knows exactly what she is doing and is using her tongue to stimulate him like a pro, keeping him on the edge.
She bobs her head faster as his balls now rise up and touches her chin. He is very close now and she believes that his load will be enough. Gracie has never been wrong when judging how much a guy will cum and this proves to be no exception. Penn screams like a whore as his dick sprays a huge load of semen into Gracie's mouth. He fills her mouth up with his cum and she eagerly drinks it all down. Then she withdraws the rod and wanks him hard, saying 'Cover me in your cum." Her strokes make him blast her face with his warm ejaculate. He is wide-eyed in shock as he shoots ropes after ropes of cum all over her beautiful face. The young geek is now decorating his former pediatrician's pretty face in his seed. He paints her gorgeous face white with his cum. Soon her entire face is covered in his spunk.
"Your virgin cum is so delicious," she remarks, with her face drenched in his young semen. "I love feeling your warm jizz all over me like this." He blushes as she then takes her skirt and panties off, revealing her hairy cunt to him. The full bush above her snatch is alluring. "You are going to eat me out now." Her words compel him and he quickly gets on his knees, planting his face in her hot cunt. Her snatch tastes wonderful and her pubic hair smells amazing to him. She moans as he laps at her labia and licks up her nectar, eagerly tasting her delicious womanly juices. This boy was born to eat pussy, she thinks as he gives her head, sucking her clitoris.
His attention brings her off and she has an orgasm, squirting all over his face and in his mouth. Gracie wants to freak her cute boyfriend out so she pushes him away and turn around, placing her elbows on the couch seat and thrusting her round ass out at the nerd. With her thick, meaty backside in his face, she tells Penn "I want you to eat my asshole out next." She expects him to panic at the task and is shocked when he obeys her without hesitation, kissing her dirty asshole and burying his tongue inside her ass. "Wait, honey. I was joking. You don't have to."
"I know that," Penn says, moving his lips away from her sphincter. "But I also want to do it. Your asshole is so delicious." His words make her cunt spasm as Gracie realizes just how well she trained him. In just one week, she has managed to make her boyfriend so subservient to her that he actually tells her her asshole tastes good to him. And Penn does find Gracie's musky shithole to be delicious. It's making his cock so hard, even though Penn just cummed earlier. He keeps on rimming her ass until she has another climax, with his tongue buried deep inside her buttocks.
Once that's over, Penn gets up and sits back down on the couch right next to his much older girlfriend. Gracie just wraps her arms around him and rests her head on his shoulder. Gracie kisses his cheek and he blushes shyly but lets her hold him, feeling safe in her arms. "You're so wonderful, sweetie," she tells Penn. "Going down on my asshole like that? That was so sweet of you. Do you really think my ass taste that good?" The boy quickly nods and Gracie smiles happily. "Perfect." They sit there like that together before Gracie says "I need to pee. Just give me a minute, baby."
"You don't need to go to the toilet," her boyfriend says as he lies down on the floor and looks up at her. "You can use my mouth. Piss in my mouth and I will drink every drop of it. Let me taste your urine, Gracie." Gracie couldn't believe it. She squats down over his face with her hairy pussy hovering there for a few moments before starting to urinate. She starts pissing in her much younger boyfriend's open mouth. Urinating with a blissful sigh, she quickly fills up Penn's mouth with her salty urine. The young boy swallows every drop of her piss like he promised her he would, to her great delight.
Once Gracie is done urinating in his mouth, she also uses his tongue as her toilet paper. "Thank you for that," she says to him. He nods shyly as she then ruffles his hair and puts her underwear and skirt back on. She then drives him home. The doctor parks right in front of the house since she knows that his parents would be at work right now. It means she can linger and kiss him on the lips before leaving. He goes into his houses, his cheeks on fire as he thinks of how soft her lips felt against his own. He soon realizes what is going on. He is now falling madly in love with Gracie.
...
Two days after she sucked his cock in the living room, Gracie has Penn at her place. She is sitting next to him on her couch, with her arm wrapped around his shoulders. Gracie is thinking of how she could get into his pants today. Her cunt is begging for attention. After she saw his dick, she knows that he would not bring her pleasure from sex. Gracie still wants to bang him though. It can help her gain even more control over Penn than she already has and that is what she wants, to have the boy she is in love with in the palm of her hand. It will make her feel much happier.
"Let me make you cum again," she says to him as she grabs his dick through his pants, groping her young boyfriend. He is a lot less reluctant to let her have her way with him now, although the two of them still haven't had sex yet. The boy just shyly tells her Gracie that she can as she unzips his pants. She lowers it with his boxers and wraps her fingers around his penis, jerking him off. Her hand rubs his pre cum all over the hard shaft, covering the veiny tool in his own clear, sticky liquid. "You're so fucking cute, baby boy," she croons in his ear.
"Thanks," he murmurs shyly as she is stroking his cock. She jerks his dick at a steady pace, giving him light kisses up and down the side of his neck. Her lips caress his flushed skin as Penn sweats from arousal. The way she is handling his genitals is making him really horny. She turns him on like no one else ever could. Already he is her submissive and becoming more and more obedient of her each day. "You're so good at this." Gracie smiles in appreciation, loving his compliment a lot. Her fingers form a tight grip around him as she squeezes and pumps his manhood, making more blood flow to the area.
She then lets go of the boy's cock for a moment and yanks her top off to show him her large boobs. Her tits are erect. Gracie smirks as he stares at them with his mouth hanging open. Then she lies down on her stomach and wraps both of her breasts around his prick. "I will titty fuck you now," she informs Penn in a sexy tone. "I'll make you spray your warm cum all over my tits. I want to feel your hot, messy cum dripping from my huge boobs, baby." Then she starts to slide her breasts up and down, using her cleavage to stimulate his rod. "Fuck my tits, cutie pie," Gracie orders them.
The boy obeys his girlfriend, thrusting upwards between her soft breasts. He fucks the valley of her boobs, nestled in the cleavage. Penn moans as he feels her warm tits on his dick and fucks the gap between her mounds of mammary flesh. Her breasts feel so wonderful on his dick as he fucks her tits. "Ahhh," he moans out loud. She smirks as he grabs her boobs and fucks them. Gracie loves how weak he is as he sits there with his dick nestled between her large breasts. He is completely hers now and she knows it. She loves the power her tits give her over her cute boyfriend. It is so intoxicating and she can never, ever have enough of it.
He is soon unable to take the incredible amount of pleasure. With a loud cry, he being spurting out of the tip of his hard cock, firing strands of cum all over her large tits. She smirks as her boyfriend is losing control of himself, cumming all over her massive boobs over several seconds. It amuses her to see him cry out in pleasure as he covers her boobs in his semen. His hot seed splattering all over her breasts makes her feel so warm too but she enjoys the power she has over him at this moment the most. He could do nothing but give her what she wants and drench her tits in his hot jizz, soaking her pair. "Thank you, my baby boy," Gracie tells him as he heaves from the exertion.
She then takes her skirt off, revealing that she was going commando under it. Her forest is glistening with the nectar. Gracie's cunt has a very powerful smell at the moment. Her hairy pussy smells so strongly right now because of how turned on she is, as she tells him "You are going to fuck me today." She then leads him to her large bedroom where she lies down on the bed on her back. He stands there, eyes fixed in her wet, hairy snatch, not knowing what to do. It is going to be his first time, after all. "Come on. Stick your hard cock inside my pussy and fuck me till you cum. I've got an IUD inside me so you can give me a creampie, darling."
The blushing boy obeys his much older girlfriend. Penn gets between her thick, powerful legs. He lines the tip of his dick up with her slit before penetrating her. Slowly pushing through the hole, he enters the warm orifice. It feels so hot inside her, as if the tunnel leads up to a molten core. Her passage heats up his dick, searing his manhood as the boy starts fucking. He fucks her slowly, being unaccustomed to how a vagina feels. She locks her ankles on his back, slightly above his buttocks, pulling him in as deep inside her as his dick could reach. "Come on. Fuck me really hard now, my darling baby boy," Gracie says to her lover.
Penn begins banging her a little faster as she encourages him. He slides in and out of her with his dick, pumping the rod in and out as she smiles at him. She gives him a smirk that says it all. It tells him how helpless he is. All he is doing right now is giving her control over him by surrendering himself to her. He is a whore, fucking his mom's best friend. It isn't just who he is. It's what the boy is and there is no use trying to deny it. "Grab my ass. Squeeze it. I want to feel your weak hands squeezing my thick ass," she orders him in the sexiest voice he has ever heard in his life.
The boy couldn't hold it back longer and does what she says. Penn reaches down, eagerly grabbing a fistful of her asscheeks. Feeling her muscular ass in his hands trigger his climax. He starts to scream as his dick pulsates violently, throbbing before firing gallons of cum deep in her pussy. Penn's whole body is convulsing as his balls and cock work together to unload inside her, filling up her womb with his semen. His thick seed spatter against the insides of her muscular vagina as she laughs at him. "Oh you are mine now, baby boy. From the moment you slid your cock into me, you were already mine. But now that you're cumming inside me, this is just sealing the deal."
Penn collapses next to her on the bed but she hasn't had enough yet. Gracie gets up on all fours, shoving her huge ass out at him. "Fuck my ass too. You are going to feed my asshole your cock and fill up my ass with your cum, you slutty little boy." He shakes his head and tells her he is too exhausted, but his girlfriend isn't having any of that. "I can see that you're still standing. By the time I'm done with you, you should be unconscious. I'm going to drain your balls and milk you dry, and I'll use my ass to do that. Now stick your cock in my ass and cum in my bowels, or I'll beat you up and knock your teeth out."
The nervous boy probes through her tight sphincter. Her anal ring doesn't have to expand much to take him in as she has had much bigger cocks before. It only takes a few seconds for Penn to bury himself balls deep inside her ass. He gasps in shock at how pleasurable being in her buttocks feel. Her asshole is even tighter and warmer than her pussy. The friction is amazing as he now thrusts in and out of her ass. "Yes, baby boy. Fuck my huge ass. Call me mommy and cum in mommy's ass. Fill mommy's large ass with your spunk," she dirty talks her younger boyfriend.
"I love your ass so much, mommy," he moans. "Mommy's ass is so tight. I'm going to cum in mommy's ass now." He fucks her massive ass for the next few minutes before unloading his balls into her bowels, filling her ass with his thick cream. Penn floods her ass with his hot cum, jizzing inside her buttocks until he has no cum left to give her. Then the boy really does collapse on the bed next to her as she lies down next to him. She looks at him with love, feeling so proud of herself for being able to break him in in such a short amount of time. Penn no longer has any sense of self and is now her property, ready to fuck her at anytime she wants.
She feels the need to pee and shakes him awake. "Open your mouth," Gracie instructs him. He knows what she now plans to do and gives her a smile before opening his mouth for her like she told him to. She squats over his head and is soon pissing into Penn's mouth. The taste of her delicious piss makes Penn smile as he gulps it down. The stream of urine keeps on coming, hitting the back of his throat, but he doesn't mind at all. "Well done, my sweet little boy," she tells him and pats him on the head as she uses his tongue for toilet paper and wipes herself clean. She then puts her skirt back on and helps him get up.
"Let me drive you back to your place," she tells him as she leads him to the car and then makes him sit in the shotgun seat. Buckling up, Gracie starts the car and begins driving towards his house. It won't be long now before she tells him about how she lied to him. Penn is definitely addicted to her now. Her lips, cunt and asshole have already broken his will and he is now her sex slave. He won't be able to leave her because she's conquered him so completely. His dick wouldn't let him leave. Not a chance in hell. All she has to do is make it final when she tells him that his mom does not know yet and he will have to defy her to be with Gracie.
Once she's dropped him off, she goes to the shopping mall where she shops for the next half an hour. Shopping helps her relax and soothes her nerves. She might have hidden it from others well but deep down Gracie is the tiniest bit afraid of how her young boyfriend will react to the news that she deceived him into dating her. He could get upset at her if she doesn't reveal it to him in the right way and at the right time. That is why she has to be very careful about how she does it. She couldn't mess this up. Even though she is fairly certain he is pussywhipped by her now, she still doesn't want to take more risks than she should, so she'll set the atmosphere just right. It's Valentine's Day the next week Everything will be perfect. She will prepare him a special dinner and charm him even more than usual.
Once he is in a wonderful mood, she'll tell him about how his mother doesn't know that they are dating yet.
....
Gracie has prepared a great meal and is now waiting for her boyfriend to arrive. She can't wait to give Penn the present she got him for Valentine's Day. He will definitely love it. The doctor thought it is the right thing to do. She will make it a special day for Penn to put him in an excellent mood. Then Gracie will tell him how she lied to him about his mom already knowing of their relationship. He might be shocked by the news and a little upset, but not nearly as much as he would have been had she not taken the time to make the Valentine's Day perfect for the both of them.
Penn arrives about ten minutes after she has finished setting up the place. He gasps in shock at how romantic the setting is. The boy lets her hug him and then kisses her on the lips. "Honey," he says. "This is perfect." Then he says "But you didn't have to do all this all by yourself. I could have helped you. You must be really tired setting everything up. Let me rub your feet for you after the meal is over." Gracie feels pleased that he is so considerate of her needs and nods, before getting him to sit with her at the table. She then pours him a bit of water and some wine for herself.
"The whole point of this is to surprise you, baby," she explains. "How could I let you help me set this up and surprise you with it afterwards? I won't say no to the foot rub though. You are so good at massaging me." Gracie's compliment makes him blush. Penn is still not used to her complimenting him, even though the two of them have been dating for a bit of time now. He would probably still take a little while to get used to this. A few more weeks, maybe. Yes, that'd be enough for him to fully adjust to his life as her much younger boyfriend. He is surprised by himself adjusting this well already.
"Well, consider me surprised," he tells her. "And also delighted too." The two starts eating and Penn quickly remarks "Wow, your cooking really is amazing!" Gracie is now the one to blush slightly from his compliment. "I mean it! This is seriously great! I love the sauce you used with the snow fish." It makes her feel really proud since Gracie made the sauce herself from scratch. She watches him eat the dish she cooked with a light smile on her face, happy to see how he clearly enjoys it very much. She knows he isn't faking it. She knows him well enough to tell if he's faking his pleasure or not, and he clearly isn't.
She touches his cheek gently. "Good," Gracie whispers. "Because I did all this for you." She then hands him the small, wrapped box. Inside is a nice watch. He gasps and quickly thanks Gracie for the gift. "It's no big deal, honey," she tells Penn. Now is the chance she has been waiting for. Gracie takes a deep breath. Penn looks at her intently, noting how her expression has gotten serious all of a sudden. "There's something I have to tell you about. It's really important to me and I want you to please tell me you won't get mad at me. At least not until you've already let me finish saying my piece."
Penn frowns in confusion. He doesn't know why but the way Gracie said that and is looking so intently at him right now is making him feel nervous. It makes him feel that what she says next might not make him feel very happy. It could dampen his great mood and he doesn't want that. But he still wants to listen to what she has to say. So he tells Gracie "Well go on then. I'm waiting. I promise I won't get mad, at least not until you're finished." Penn can control his feelings and is pretty sure that nothing she can say will make him lose his cool, now that he's fully resolved not to freak out too soon.
"I didn't tell your mother yet," Gracie whispers. He raises his eyebrows at her in response. The boy prompts her to go on since he isn't sure yet what she is taking about. Gracie says "I didn't tell her that you and I are dating." Now her boyfriend starts to show the first signs of being upset. His eyes go wide and he turns red, and not in that cute way too. But Penn quickly calms down, and she decides to go on. "I asked her if she'd be okay with me dating you. She said no, so I lied to her that I have given up on the idea already and decided to let you go. I know it was terrible of me to do this. Could you please forgive me?"
Her words make him pause. The teen is confused and upset but his heart tells him to just forgive her because they are together now and that's all that matters to Penn. So he gives her a light smile as he tells her "You can explain why you think I'm worth lying to her for. I want to hear it. Tell me your reason now and I'll listen to you. Why did you think it is worth lying to your best friend, so that you can go out with her son?" He looks at her, thinking about whether he is too forgiving, being willing to forgive her if she tells him what he wants to hear. He is really desperate to hear those three words and eight letters.
Gracie knows what her boyfriend wants to hear. She wants to say it to him too but still feels that she isn't ready to say it to him yet. That's why Gracie takes a deep breath and decides to plaster an innocent look on her pretty face, acting like she doesn't know what he's talking about. "What on earth are you taking about, baby?" she says to Penn. "I lied because you're cute and I want to date you. That's all. There's nothing more to that." Penn looks deeply wounded by her words and she really wants to take it back and tell him that she loves him. But it's too difficult to say that right now, even though she really wants to.
She has been in love with him for some time now and knows about her own feelings, but for some reason can't say those words. Penn tells her "I'm in love with you now, Gracie. If you tell me you love me, I'm ready to defy my mom for you." He looks at her hopefully, waiting for her to say something, anything at all. But she just stands there, looking at him silently. Her eyes tell him how she really feels and he is glad, but he wants to hear it from her, for her to tell him why she did what she did. He already knows why but he really needs to hear it so that he can know she is as serious about their relationship as he is now.
"I'm sorry, but I don't know if I can say those words back to you right now. I do care about you a lot but I don't know if I am ready to say I love you yet," Gracie says to her younger boyfriend despite already being in love with him. Even when she first asked him out and then fucked him, Gracie still had a tiny bit of doubt within her over whether or not she is doing the right thing. She might have planned to tell him she loves him today but now that the moment is here, she is chickening out. It is one of those rare moments where her usually great courage fails her.
"I love you, Gracie and I know that you love me too," Penn says boldly. "There is no other reason for you to lie to my mom, who is your best friend. You are really serious about with me, so much so that you risk greatly upsetting her. I know you're nervous to admit it now but please, just say those words to me. I need to hear them. I need to be with someone who can admit her feelings out loud. I am completely in love with you now because you made me fall for you. You made me fall in love with you and I'm not afraid to say that, so why can't you just admit that you love me too?"
Penn's words strike a cord within her heart and she finally overcomes all her fears. "I'm sorry I chickened out at the last second," she says. "I meant to tell you this before preparing the meal but I panicked. I was worried about how we would make this relationship work with your mother disapproving of us dating like this. But now I realize I have zero reason to fear." Gracie then takes a very deep breath before saying "I love you too Penn. I love you so much. I love you more and more every day if that's even possible." She then captures his sweet lips in a passionate kiss, now no longer afraid of what the future may hold for the two of them.
The two of them finish the meal and then make love in her bed afterwards. It is the perfect evening for them. She has planned this well and it ended the exact way she wanted it to. Yes, there was the moment when she chickened out of telling him she loves him, but it didn't last too long. With his help, she was able to overcome it and confess to Penn how she really feels about him. It went very well, considering everything. The sex is also pretty good, as he eats her out after cumming in her cunt. It makes her cum so hard to be able to degrade him that way, and she'll never let go of him, no matter what. He is hers and hers alone.
"I have an idea," Penn suddenly says to her as they cuddle in bed after the sex. Gracie looks at him as he gives her a warm smile. "About telling my mom. I think the two of us should go to her together tomorrow. We will hold hands and walk into the house, and tell her we are in a relationship now. She'll accept it once she realizes how serious I am about us. Walking in together while we are holding hands will show her that. I promised you I will stand up to my mom for you if I must, and I meant it. My mom will probably cave in but if she doesn't then I'm willing to move out and come live with you."
Gracie just kissed him on the forehead before saying "Sweetie, I love you so much and I don't want to risk making your mom upset. But I agree. We have to do that to show her that what we now have between us means a lot and we won't give it up. I'll do it the way you suggested. We'll walk in holding hands and she'll see and realizes that we both really love each other a lot. It'll be enough to convince her. It should be and I'm sure she'll approve of us. She'll approve of me dating you because it'll make you happy." She then kisses Penn and fucks him, making the boy cum in her pussy again before he passes out. He is a lot more resilient now, taking five orgasms to knock him out now instead of just two like before.
As he sleeps, she stares at his face and peppers his cheeks with kisses, also kissing him on his eyelids. She loves him so much and she is never letting him go, no matter what.
.....
Carole is sewing at her desk right now. She is doing it to help distract her from some of her concerns. The woman is a little bit worried since her son has been acting weird lately. He always looks so cheerful. Of course, that's a good thing. Except, she has no idea why Penn is so happy today. She knows he is dating a girl, but for some reason her son would not bring the girl over or talk about her at all. It's almost like he is afraid that he would upset Carole with his choice of who to date. But who on earth could Penn date that would upset Carole?
She recalls how her best friend Gracie had once asked her if she would be fine with her dating Penn. Carole had told her to fuck off and berated her harshly right then and there. Is it possible that Penn might be dating her though? No. It can't be. Gracie was his pediatrician and also his mom's friend. He wouldn't go out with her, right? She is worrying way too much. It's most likely just a girl his own age, and he's probably too shy to bring her to meet his mom. That's all there is to it. There's no evidence that he is seeing her best friend, so Carole is just being way too paranoid.
There's the sound of someone inserting a key into the lock of the front door and entering the house. Carole looks up and is surprised to see both her son and her friend arriving together. What is even more surprising to her is how the two of them are holding hands as they enter the house. She frowns. "What's going on? Why are you two holding hands?" she asks Gracie and Penn suspiciously. Her frown deepens when they avert their gazes, looking aside guiltily under her scrutinizing eyes. She doesn't like this at all. It's clear that these two are hiding something from her, and when her son hides something from her, it really irritates Carole a lot.
Gracie takes one little step forward and approaches Carole. She has on her face a tentative look. "Listen to me, Carole," she begins. "We have something to tell you. It might be a hard pill to swallow and I'm sorry for not telling you earlier but it wasn't the right time then. But it is the right time now." She takes a deep breath as Carole stares at her, already aware of what's coming but still unable to believe it. "Me and Penn are dating. We also already said 'I love you' to each other a few times. We are here to tell you this today because I don't want to keep it a secret from you anymore."
Now it's Penn's turn to say something to his mom. He takes her hands as she stares at him and her best friend, still in shock at the news she just go. "Mom, I know that this can be difficult for you to accept. But I want you to know that I'm really serious about Gracie. I love her a lot and want to be with her. Can you please accept that for me? It would mean a lot for me if you accept us being in a relationship." He looks at her with a lot of hope in his eyes, begging her to say yes. The boy sighs when his mom suddenly rapidly shakes her head with a furious expression on her face.
"You betrayed me!" Carole shouted at her best friend, pointing at her pretty face with a shaking, accusatory finger. "I told you to stay away from my son yet you still asked him out! How could you do this to me, Gracie? You are my best friend. You helped me raise him and you were also his pediatrician for Christ's sake!" Then she whirls on Penn who is standing there, frozen. Carole is now unleashing her rage on him after she has already yelled at Gracie. "And you are my son. How the hell could you have possibly thought that I would be fine with you dating her? Why did you even go out with her in the first place? She's actually a couple of months older than I am! You're dating someone who is older than your mom!"
Gracie quickly steps back in. "It's not his fault," she says. "I lied to him. I told him that after we talked about this, you were okay with the two of us dating. He only found out that you didn't know of our relationship yesterday. So please, don't blame Penn because it's not his fault. I was the one who lied to him. It's my fault. I am the one to blame. I only lied to him so that he would date me, because I love him so much. I can't live without Penn. So please, do not make him leave me. I love this boy more than anything in the world and I promise I will cherish him and take good care of him. I'll always treat Penn right."
Hearing this makes Carole's expression soften considerable. She sighs. "Well, I can't say that I like this," the single mom mutters. "But it's understandable. The age gap aside, you two are perfect for each other." Penn beams. "So I guess what I'm trying to say is that you two have my blessings. I won't stand in the way of your relationship anymore." Her son rushes towards and flings his arms around her in a massive embrace. Carole smiles softly as she hugs him back and tells Carole "You better keep your word. Take good care of my son. If you ever hurt him, I will hunt you down and kill you. Got that?"
Gracie nods. "I promise I'll be good to him," she says. After Carole lets go of Penn, she gestures for Gracie to step to her. The two women then hug too and then Gracie says "Come on. Let's go to the mall and have some lunch together. We can also get ice cream too." Carole is happy with the idea and she, her son and Gracie all leave the house together. Penn is delighted by how smoothly it went today. His mom and his girlfriend are now talking to each other about the relationship. There is nothing for him to worry about, now that Gracie's told him how she really feels about him and isn't hiding it inside for any longer.
The meal proves to be one of the best ones of his life. Penn loves the way the two most important women in his life are still able to remain friends after the shocking revelation. He was worried it would destroy their friendship but it did not, so that's something for them to celebrate together. His mom is now a bit happy, to be honest. She doesn't know anyone else she would trust with her son as much as Gracie. She knows Gracie could take care of Penn and be trusted to treat him right. Now Carole is actually a little ashamed of herself for not handling the news very well at first. But that's all in the past now.
At the end of the meal, they go to the ice cream store together. The three of them have an open conversation about what the future entails before returning to Carole's place. She sends her son to his room so that she and Gracie could talk by themselves. Penn heads to his own bedroom and sits down on his bed, smiling brightly. He feels much happier now than he did yesterday. And that is saying a lot too, since he was already a very happy boy yesterday when Gracie told him she loves him. Today is just that bit more special than yesterday was. Today his mom found out about him and her friend dating, and she is okay with it. That's more than he dared hoped for last night.
"So what are your plans with my son now?" Carole asks her best friend in a very serious tone. "I know I told you I am now okay with you dating him, but I still really want to know where you are taking this. He is my son and I love him and don't want to see him get hurt. Tell me what your intentions are now." Gracie knew that sooner or later she'll have to deal with this. Carole is serious about protecting her son. She raised Penn as a single mom ever since her late husband died in a car accident. It's why she can be overprotective of the nerdy boy sometimes. Okay, most of the time.
"I want to marry him one day," Gracie tells her friend. "Not today, but one day I will pop the question. I'll ask Penn to marry me, and I know that he will say yes, because he loves me as much as I love him." Carole nods. She is glad to see that her best friend isn't just using Penn as a sex toy. The fact that Gracie has already thought of marriage shows how serious she is about being with the boy and that's what Carole needs. The reassurance that her friend is taking him very seriously and not just playing around with the nerdy boy. She can now fully relax and let go of all of her concerns. No more need for Carole to worry over her dear son. He is in very good hands now and she's happy.
That night Gracie goes straight home and enjoys a wonderful sleep. She is a very happy woman now. Her boyfriend is still dating her because his mom who is still her best friend approves of their relationship. She knows he would still be with her even if Carole said no but it is just so much better this way. This way everyone is happy. There is nobody fighting. Everybody is pleased with the outcome. She knows soon she would be getting married to Penn. Maybe in the next three months, or four, just in case he doesn't feel ready yet. Definitely by the end of this year though. She won't let her adorable boyfriend stall for any longer than that. He'll marry her even if he doesn't feel completely ready by that point.
Four months later, Penn is ready for it. She doesn't know how she knows. She just knows it. Gracie buys a golden ring in secret. Later the same day, she takes him to the same French restaurant that she took him to on their first date. He is overjoyed when she gets down on one knee and shows him the ring. "Will you make me the happiest of woman and be my husband?" she asks. The boy nods with tears of happiness streaming down his cheeks. He kisses her as she slides the ring onto his finger. Penn has never been this happy before in his life, not even when the two of them went on their first date together. He knows she is the one he wants to be with, the one and only love of his life.
Carole knows that this might not look like the perfect situation to outsiders. Her son is dating her best friend, after all. It is an arrangement that is far from normal. But both of them seem to be very happy from it and that's really all that matters to Carole. The two most important people in her life are happy together and they will always be happy together. So there is nothing for Carole to worry about now. Everything is well. No problems, no worries, no causes for concern at all.
Her only concern now is finding a good dress to wear as the mad of honor. The wedding proves to be a beautiful one. It is the perfect ceremony and Penn and Gracie both smile widely as they become husband and wife.