Chapter 1: Trading Up For a Milf

I’ve always considered myself a level-headed person. It’s one of my greatest strengths. There’s very little on this earth that can really get me to flip my shit, with a few notable exceptions. Now, what would these exceptions be, you ask? Well, I only know one for sure, and that would be walking in on my cheating whore of a girlfriend bobbing her head up and down on a cock while jacking 2 others in both her hands in the middle of a public bathroom. 

If that happened, I would totally flip my shit. Luckily, what are the odds of that?

Much higher than I would hope, evidently.

The scene I just described is playing out directly in front of me. My vision goes red, and before I know it I’m beating the shit out of some dude on the floor while my girlfriend is crying in the corner. I’m about to deliver the coup de grace when I’m yanked off of the dude underneath me. The other 2 ran and got teachers, who are now yelling at me and pulling me out of the bathroom, while others help to clothe my girlfriend and her probably-still-alive lover.

Instant 2-week suspension, with a potentially worse punishment waiting for me down the line. There’s also the potential of criminal charges, which isn’t great. I feel a bit of regret, but it pales compared to the rage swirling within me. Honestly, It was probably unfair of me to attack him. My now ex-girlfriend is the one who broke our trust; It’s not like I can hit a girl though.

I kind of want to die. I’m now at home, laying in bed, staring at the ceiling. I just got done with the most painful reaming of my life courtesy of my mother. She said I was reckless, that I’d done something unforgivable, and that I would need to apologize. I kind of agreed, barring the last one. No way in hell am I apologizing to the dude who railed my girlfriend, but that was the one she seemed to care about the most. It seems that if I apologized my punishment may be lessened, but there’s no way in hell I’m doing that. So here I am, laying in my bedroom, forbidden from leaving the house until I “come to my senses” as she puts it. Fuck this.

Night falls with neither me nor my mom having budged, and I fall asleep. 

“Hello there hun,’” says an unfamiliar, feminine voice.

I’m standing in the middle of grey. The walls, the floor, the sky above me, all grey.

“This is a dream right?” I ask

“... Something like that.” says that same voice. It’s noticeably deep for a woman, but still obviously female. Her arms wrap around my shoulders from behind, with her hands clasping each other on my chest

“Who are you?”

“Who I am doesn’t matter. we need to talk about you. I saw what happened today… that must’ve been dreadful” I feel a rather large chest pressing on my back, but I seem to be unable to move.

“You were watching me getting cucked?”

“I would have phrased it a little more… delicately… but yes, I saw your beloved betraying your trust” her hands grow tighter around me as she speaks.

“Are you like… an element of my subconscious here to help me deal with my grief?”

“No. I’m here to extend an invitation.”

“To... what?”

“An invitation to play a game. A game of love and lust. A game that I think you would be perfectly suited for.”

A game? I'm pretty interested in hearing more. It's not like there can be any harm in it, considering this is a dream and all.

“That sounds interesting.”

“So you accept?” Her arms grow even tighter around my shoulders. I think more is riding on this than I'm aware of.

“I’d like to hear more about it first.”

“As you should. It’s a game about lovers, and stealing them. It’s about taking a woman and dominating her until she’d rather die than lose you. Every 2 weeks you will receive a target, who you need to seduce and turn in to your woman. Every time you succeed, you will be granted power.”

“I’m intrigued, but first, 3 questions. Firstly, why? Secondly, what’s the catch? Thirdly, why me?” 

“The reason is that it’s entertaining, there is no catch, and I chose you because I think you would be an... interesting player. Speaking of which, you won’t be the only one playing.”

“Will the other players be after the same targets?”

“For the first target, every player will have a unique target. After that, targets will have overlap.”

“How long will the game last?”

“As long as it continues to entertain our audience.” It could go on forever? that's a scary thought.

“Will I get anything for playing?”

“Other than a harem of submissive lovers who love you more than life itself? You’ll get powers far greater than other humans, and a chance at winning the final prize”

“And the final prize is?”

“A secret.”

“Alright, so to recap, you want me to play a game about domming women, and for doing that you’ll give me magic powers?”

“A simplistic view… but yes, that is correct.”

“Sign me up.”

“Before you are officially allowed into the game, you must prove that you are capable. I have no doubts that you are, but I’m not the one who decides. Your first target is the mother of the man who had intercourse with your lover. Steal her within 2 weeks, and you will be allowed into the game.”

“If I fail?”

“There is no punishment for failure, but there is a punishment for talking. Do not disclose what we have talked about here today, whether you succeed or fail. Also, don't involve law enforcement. Bringing the law in for any reason is forbidden.”

“I’ll do my best.”

“I know you will. You have a bright future ahead of you.”

I jolt awake. Was that… was that a dream?

 

I get out of bed and head toward the bathroom, still a little dazed from my less-than-stellar sleep. The faucet makes a loud shhh as I splash a little bit of cool water on my face to help with the grogginess. I grab the hand towel next to the sink, wipe my face, then take a moment to look in the mirror. 

A few of the girls I've met have told me that I'm attractive, but every time I look in the mirror I don't really see it. There are a lot of attractive features, but they all came from my dad, and god knows he's the last person I want to look like. I'm just barely over 6 feet tall, have thick, unkempt hair that I struggle to keep tidy, and a strong chin. My beard is still coming in, but my mom says the stubble makes me look nice, so I keep it at a short but visible length.

Now that the tiredness has been dealt with, I go make some breakfast. It’s late, much later than I normally sleep so the grogginess is a little strange. Most of the time I’m up at 8, but today I just barely rolled out of bed at 11:30. Because I’m suspended, I have plenty of time to make something a little more substantial than my norm, So I make some eggs and toast, then sit down to eat. I certainly have a lot to think about. Was that all just a dream? It certainly didn’t feel like it. The feeling of that woman’s arms around my neck… her breasts on my back… there’s no way that was just a dream. I have no proof, but I can’t shake the feeling that it was something more than my tired mind playing tricks on me, Which leaves a new question. 

How the hell am I supposed to seduce Darren’s mom? I have no experience with older women and little experience with women in general. The only woman I have successfully “seduced” was also seemingly fucking everything that moved. I’ve never met my target, and I have no inroads. In addition, I beat the shit out of her son, and I'm grounded. I can't imagine either of those facts has exactly got her panties dropping. How the hell am I supposed to do this?

I don’t have the chance to answer that question. The front door opens and my mom steps in with a smile on her face. She’s turning 40 this year but she looks much closer to 30. Her skin is still smooth and has no noticeable wrinkles. She has beautiful blonde hair and a tall, buxom frame that even I, her son, take notice of.

“Oh Samuel~! I’ve got a surprise for you!”  She says, far too cheerily.

My danger senses are going off. This is my mother's signature "so angry she wrapped back around into being cheerful" mood. I rarely get to see it, but our past battles have been legendary.

“Mom? You seem cheerful.”

“Oh no, I’m still fuming, but I met up with Darren’s mom and we’ve reached an agreement.”

“Really?” I don't know if this is a good thing or a bad thing.

“She wants to meet with you and discuss what happened. I have her address and it’s about a 15-minute walk.”

“You’re just going to hand me over to the lions?”

“Gladly. Now you best get to marching little soldier!” She says proudly and gestures to the open door.

“Can I finish my breakfast?”

She sighs.

“Okay, but after breakfast, you’re heading over there. Don’t think you can just skulk away to your room!”

“Fine.”

And so I finish eating and begin my journey to Darren’s house. This might be a stroke of luck, but I’m not sure. I can’t imagine she’s going to be too happy with me after I turned her son's brain into a gravy. As I walk I look at the scenery. It’s fall, and the leaves have already changed color. There are trees all over the residential street I’m walking down, with leaves blowing everywhere. It’s a bit cold, so I regret not bringing a jacket, but not so cold that I want to go back and grab one.

I arrive at my destination in 15 minutes flat and knock on the door. It swings open and I am greeted by a beautiful older woman. She looks like she’s about 30, but there’s no way that’s true because she’s the mother of an 18-year-old child. She’s tall as well, standing about 5’10”. She’s only a few inches shorter than me, and I’m 6’ flat. She’s got beautiful dark hair, a curvy figure, and thick lips that a certain type of person would call DSL’s. She’s gorgeous. My eyes return to her face, and... is she checking me out too?

Her eyes return to mine, and she realizes I have definitely seen her eyes wander. She seems slightly embarrassed and says “So you’re the one who Darren fought with… come in.” The door opens further and I step into her home.

The house is well-kept, with little to no visible mess. There's a light fragrance of cinnamon, furthering the well-kept, homey feel. She gestures for me to sit on a couch, and sits on my left, a cushion away. I'm not really sure what to do. It looks like she's waiting for me to say something. I guess I should introduce myself.

“Hello ma’am, my name's Samuel.”

“I know what your name is, your mother and I had a nice long chat about what happened yesterday. Did you know that Darren is in the hospital?”

“No… I didn’t.” That’s bad. I knew that I hurt him but I had no idea how much

“He’s got a concussion. We still don't know how bad it is.” Shit. I knew that I hurt him, but I didn't think I actually scrambled his brain.

“I didn’t mean to hurt your son that badly.”

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“Do you really have any remorse?”

“Uh, yes?” I wasn’t really sure that I did, but I imagine this is the answer she wants to hear.

“You shouldn’t.”

I think I might have something in my ear. I definitely misheard her. “What?”

“What I’m saying is that it’s fine. That little shit had it coming.”

“Huh?”

“My son and that girl? behaving the way they were in the bathroom? I'd be angrier if you hadn't beat him.”

“You... you're really fine with what happened?”

“Someone had to put him in his place. If I found out before you did he'd be in a shallow grave in the backyard.”

“That’s... really nice to hear. Everybody seems to be against me, but nobody cares that he was fucking my girlfriend.”

“You shouldn’t worry about that girl either, a good woman would never cheat on a man like you.”

“What do you mean?”

She slides closer to me until she’s right next to me.

“I mean... she doesn’t know what she’s missing.”

I'm ashamed to admit this, but I'm panicking right now. What the hell is going on?

I let out an audible gulp, and she continues, “a young man like yourself should be with a woman who can really appreciate you.”

“Who… who do you mean?”

She lets out a seductive, throaty laugh. “Hmm, I wonder.”

Her hand reaches for my crotch. My instinct is to pull away, but isn't this what I want? I thought seducing her would be much harder than it has proven to be. Her hand snakes under my pants and grasps my fully erect cock.

“Oh… is this for me?”

“Uh… I guess?”

She lets out another laugh and unzips my pants, pulling my prick out. I’m standing at my full length of 6 inches, and she seems reasonably impressed. Before I can say anything she’s already leaned over my lap and put me in her mouth. I can’t help but let out a loud moan. I’ve never been blown before, so the feeling of her experienced mouth and tongue working my shaft is unexpectedly amazing. Rather embarrassingly, I’m already feeling my orgasm coming on. After all that talk about appreciating me, I really don’t want to let her down. I’m trying to hold on, but... Jesus Christ, it feels so good. I can’t even think straight anymore as my hips begin to lightly thrust into her mouth. I want to stop myself but it’s like they have a mind of their own. She takes this in stride and uses their force to push me deeper into her throat. I clench my fists, then I think about old women shaking their saggy tits, I do everything I can to keep myself from blowing so soon, but I only manage to extend by about 1 minute. In grand total, this has probably taken about 3 minutes.

“I’m gonna cum!”

“MMMM”

I don’t understand what she just said, but she pushes her head all the way down to my balls, and I start to spurt in the back of her throat. I start to run my fingers through her hair as I cum.

“Fuck… That feels amazing.”

My orgasm ends. She sits back up and adjusts her clothing.

“Could your girlfriend do that?”

“N-no. She said she wanted to be more comfortable with each other before we did anything”

“What a naive little girl. Hopping on some loser’s cock, leaving her handsome… virile… boyfriend alone.”

I don’t know how to respond to that. She just referred to her own son as “some loser” and called me virile in the same sentence. I try to change the subject.

“I’m sorry about cumming so early.”

“Don’t be, it’s a compliment that you felt that good. We have a lot of time for you to get better at this.”

“Huh?”

“I’ve worked out a deal with your mother. I won’t pursue legal action if you help around my house for the next few weeks.”

“And by help, you mean what we just did?”

“By help, I mean cleaning, but there should be plenty of time for some fun as well.”

Suddenly, I feel invigorated. My punishment for beating the shit out of her son is to come over to her house and have sex with her? Sounds pretty alright to me.

My erection sprouts again.

“Oh my, that was fast. We should definitely take care of that.”

This time she stands up and slides something from under her dress. Upon closer inspection, I can see that they are her underwear.

“Have you ever done it for real?”

“No.”

“Well then, allow me to introduce you to adulthood.”

She straddles my lap. With my dick pressed up against something under her dress.

“Let me move, you just enjoy yourself”

“O-Okay.”

Suddenly, my prick is surrounded by warmth and wetness. I can only assume that this is her pussy, and the sensation knocks the air out of my lungs. The feelings coursing through me are absolutely incredible. She begins to rock her hips as I lean back into the couch cushions, trying not to lose my mind. This feels so much better than I ever could have imagined. She sees me struggling to hold it together, and decides to make things worse. She presses her lips to mine and slides her tongue into my mouth.

I can’t take this.

She presses her body hard against mine and takes complete control. The only thing I can do is try to survive under her ministrations. There's a piece of me that's angry at myself. My performance is embarrassingly lackluster, and I'm letting her take complete control because of my inexperience.

Having just barely cum, I thought that I could last quite a bit longer. That may have been wishful thinking. Having sex with this beautiful older woman is just too stimulating. My hands are on her breasts, groping them. My lips are being devoured by hers, and my cock is exploring her depths with gusto. I’m doing my best to hold on, but she isn’t making it easy. 

I manage to hold it in longer this time. We’re going for almost 10 minutes before I finally yell “I’m cumming!” She, rather surprisingly, replies with an equally loud “Me too!” With a final bob of her hips, she slaps her meaty ass onto my hips and lets out a loud moan. I can feel her orgasmic convulsions and they very quickly bring me to my own orgasm. I cling to her and pull her into an embrace, cumming deep inside of her and filling her with my seed. Wait… isn’t that really bad?

I jolt out of my orgasmic trance, “Oh… shit!”

“What’s wrong?”

“I just came inside you!”

“Not a problem, I’m on birth control.”

“Oh… that's good.”

“Are you sure that was your first time? You were great.”

I get the feeling like that was to stroke my ego. “Uh… I’m pretty sure it was.”

She finds my response funny and lets out yet another deep, beautiful laugh. “I’m looking forward to the next time. You should try to be a little more in-control, girls like that.”

“I’ll keep it in mind.”

“Unless you want to go for another round, this is all I needed you for today, so you can head home.”

“Alright.” 

I decide to use her advice right now. As I get up to leave I lean over to her and kiss her, pulling her into a possessive embrace. She looks at me with a bit of surprise and kisses me back. After a moment I begin to leave.

“This was really fun, I’m looking forward to next time. When should I come over?”

“I’d love to see you early sometime tomorrow.”

“Alright, does 10 sound good?”

“The earlier you come, the more time we have.”

“I’ll keep that in mind.”

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