Milf

MILF's Strap On Discipline

mp4 207.35 MB
Category: 

You are at an age now where the way you are disciplined for stepping out of line is about to change. Not only do I wear the pants in the Fam, I have the biggest swinging dick. That's why your old man is such a good husband. He gets my huge cock up his ass if he doesn't do everything I tell him to do. The same now goes for you. You will be a good boy, get good grades, clean up after yourself, etc. if you mess up, try to rebel, stay out past curfew or anything else you won't get grounded or have your video games taken away...noooo, you'll be stripped naked in front of your own M! Bent over & fucked hard with my monster cock!
Length: 9 minutes

Boss Boob Addiction

mp4 254.13 MB

You can't stop staring at my cleavage at work. You're obsessed. Before firing you I decide to give you one more chance. I tease you with my breasts & make you jerk off in front of me, both humiliating you & hopefully satisfying your curiosity about my boobs so you can focus on your work. (Custom vid, no name mentioned).
Length: 10 minutes

Orgasm Control For My Boy

mp4 492.21 MB
Category: 

It's time for sex ed & masturbation instruction from your loving but strict "MILF". Today you'll learn orgasm control. At first you'll be expected to sit on your hands & not touch yourself while I tease & seduce you. Eventually I'll give you permission to touch yourself & will give you a countdown to stroke & NOT cum, then hands off. You'll edge yourself & eventually be given another long countdown from 20 to practice cumming on command. You will be a perfect boy for me & cum only when I give you permission. (Custom vid, Chris's name mentioned a few times.)
Length: 18 minutes

Caught By Auntie

mp4 258.62 MB

You get caught wanking by your hot Aunt. Even worse, you're jerking off with her dirty panties that you dug out of the dirty laundry hamper. As she shames you she notices your tiny penis & your tight foreskin. She makes you pull it back even though it hurts & talks about discussing getting it snipped with your M(ilf). She makes you finish jerking off in front of her while making fun of your tiny penis & teasing you about having a crush on her. (Custom vid with the name Stephen mentioned a couple times.)
Length: 12 minutes

Naughty Boy

mp4 224.29 MB
Category: 

Sometimes a 'MILF' has to take matters into her own hands. A boy needs to learn proper self control as well as many other things about sex.
Length: 8 minutes

Teacher Supervised Masturbation

mp4 296.15 MB

This is a custom vid but no name is mentioned. I am a modern, but conservative teacher. (Glasses, blazer, jeans). Your hormones are effecting your studies so from now on you'll report to me each morning for guided masturbation. I'm professional and slightly dominant but in a nice way. I use "official language" (penis, anus, masturbate, ejaculation, etc.). This is about education and discipline. Young men need proper guidance in their sexual development. I also give you an anal toy to use & guide you in using it to have a more intense orgasm (so if you have an anal toy it would increase your enjoyment of this vid).
Length: 12 minutes

MILF's Boy: In Good Hands (MILF/boy)

mp4 286.43 MB
Category: 

Junior has been misbehaving at school. M decides he's not too old to spank but then gets a better idea when he seems humiliated to be half naked in front of her. She realizes that at his age there are better ways to get a boy to mind his M. She threatens him with chastity if he's bad but also shows him what his reward will be if he's good...she seduces him with her skilled, experienced hands...telling him that she can teach him everything about sexual pleasure & being a good lover...all he has to do is behave for Mmmmm...
Length: 10 minutes

MILF Bath Time Jerk Off

mp4 199.84 MB
Category: 

It's bath time with loving MILF. So you're very relaxed & ready for bed after your bath you're going to be a good boy & cum for me...you're also going to make sure you're very clean so you'll be cleaning that bum hole with your finger while you stroke for me... xoxo
Length: 7 minutes

MILF's Special Sissy

mp4 304.69 MB
Category: 

"I always wanted a girl!" ...We can't have the other students at school figuring out what you have under your skirt so MILF will just make sure we get rid of that stiffy before you go to school.
Length: 10 minutes

Counselors Small Penis censored

mp4 266.7 MB

This is a custom vid for Stephen & I say his name several times throughout the vid...but you can enjoy this even if you're name isn't Stephen. Here's the outline: "I'm a high school student you are a school counselor. I go to see you because somebody pulled my pants down as a prank at a pool party and the hot girls in my class saw my small penis. You are really nice & sweet about it and try to reassure me that it was probably cold water & that young women can be cruel etc. You get me to show you my penis so you can reassure me that its all in my head. You ask to see it erect so you can properly judge it. You admit to me that it is smaller than average. You take pity on me and let me masturbate in front of you. I ask you if you'd be interested in someone like me and you turn from nice to real bitch laying on SPH insults going on about your lovers huge cock & comparing the two. You do a tease showing of your ass, mocking me. Showing your tits saying how your small my cock would look in between them. Eventually you show your pussy by taking your panties off but leaving a short skirt on. I cum, you say how pathetic i am for not holding out. You mock my cock as the cum drips down it and it shrinks even smaller. You make me to lick my cum up laughing at me calling me your bitch. The End"
Length: 10 minutes