Friend Keeps Getting Best Friend's Mother Pregnant

[FantasySharer1]

-20 year old well-off, orphaned, trust fund kid with money to take care of a family (Mike)
-Best friend (Jake), 20 M, with two sisters, 18, 22, and Mom 40 (Diane)

Mike has been showing up to the house for years and has basically grown up with the family. Jake's Dad is out of the picture and Mom is exhausted working extra shifts while trying to pay for college.

Mike has always had a crush on Jake's Mom because she's funny, sweet, kind, intelligent, and drop-dead gorgeous, and at 40 has turned into the hottest most fit MILF he's ever seen. Mike has enough income from his trust-fund to take care of the entire family's bills. He secret pays off the tuition bills for all the kids (his friend and the sisters) and the mortgage on the house.

He doesn't tell anyone, he really meant it as an act of love for this family who has been like a second family to him. Diane figures out what is going on and corners him in his apartment one day and asks him why he did. He responds, sincerely, "I really love you guys and I have more money than I know what to do with. There's no reason for me not to help." Diane melts and seduces him immediately which takes minimal effort.

They end up together which initially makes Jake really angry, breaks up their friendship temporarily, but Mike moves into the house and Jake can hear Mike fucking his mother constantly. At some point, Mike has impregnated Diane 5 times, and they now have five children running around and moved into a much larger house with help.

The conversation that keep echoing in my head as the story progresses:

Jake: "I don't understand why you have to keep getting my mother pregnant every fucking year. You're rubbing it in my face."

Mike: "I don't think you understand, she's my wife. She's had more of my children than she had any other man's. She's more mine than she's ever been any other guy's. I love her. All of her. She's the love of my life Jake. Your mother. She's never had that before and I want to give it to her for the rest of her life. I'm not just fucking her. I'm her husband. Forever. And she's the one who keeps asking me to get her pregnant."

Jake: I...I never realized it was like that.

Mike: She struggled a lot to raise you and she loves you so much that she gave up her own dreams and fun. She hadn't even been with anyone after your dad who left like over 20 years ago. I think she wants to have the experience of raising a family and being taken care of. She always wanted a huge family, so I'm here.

Jake: The idea of you just fucking her, and cumming in her all the time, and impregnating her just, it bothers me.

Mike: Right now, your Mom and I have 5 kids. She told me she wants 8. There's going to be more of me fucking your mother, cumming in her, and impregnating her. The sooner you get used to it the better. But, I'm never, ever leaving her or treating her badly. That's one thing I can promise you.

Eventually would be awesome if the sisters ended up joining too and becoming part of Mike's little harem.

 

[Fuumayami]

Pretty hot. My lovely milf wife and my two step daughter wives.

 

[FantasySharer1]

Pretty hot. My lovely milf wife and my two step daughter wives.

Yeah, the idea of the step daughter "wives" is hot where he is actually their age. Would be amazing if all three were pregnant at once.

 

[GlennJenko]

I'd tweak this slightly.

The initial concept is great, and if I was writing I'd split it into parts. Part one could be up until Mike fucks Diane, or alternatively as Jake comes to accept what's happening and gives them his blessing.

What I'd shift is the mother's pregnancies. Having children in your 40s isn't common and has a higher likelihood of complications. Maybe what happens instead is that the mother had 2 pregnancies in those 4-5 years and just found out she's having another. Though she did want more, due to said complications Diane and Mike agreed this would be their last. What they then agreed was that she wanted grandchildren and didn't see why Mike couldn't be a father again, given he was only in his mid-20s. That then brings Diane's two daughters into things, and you can then end it with all three being pregnant.

 

[FantasySharer1]

I'd tweak this slightly.

The initial concept is great, and if I was writing I'd split it into parts. Part one could be up until Mike fucks Diane, or alternatively as Jake comes to accept what's happening and gives them his blessing.

What I'd shift is the mother's pregnancies. Having children in your 40s isn't common and has a higher likelihood of complications. Maybe what happens instead is that the mother had 2 pregnancies in those 4-5 years and just found out she's having another. Though she did want more, due to said complications Diane and Mike agreed this would be their last. What they then agreed was that she wanted grandchildren and didn't see why Mike couldn't be a father again, given he was only in his mid-20s. That then brings Diane's two daughters into things, and you can then end it with all three being pregnant.

That's a great tweak. All three being pregnant together, even scheduling appointments back to back with the same Dad. The whole clinic staff looks at each other and chuckles when the appointments come.

 

[DarkSollat]

Why is Jake even in this story? He serves no purpose other than being miserable.
Interesting question is if 40 yo woman's body is even able to support that many of frequent pregnancies. For some reason it escapes my suspension of disbelief.