Older Woman/Younger Man
Humiliating MILF's Boy
My small-dicked boy is a bit of a loser. He has decided he wants to be a super hero for Halloween & has picked out this ridiculous mask. I make him parade around in it in front of my sexy girlfriend & show her his unusually tiny penis. I make him worship our boots & do other humiliating tasks. Poor boy! (Click to see more of Nikki Whiplash)
Length: 11 minutes
Your MILF Is A Lesbian
This is a wonderful bedtime jerk off instruction for my MILF's boy...with an added twist...it also includes me letting you know that my hot girlfriend is more than just a friend. I know you have a crush on her & maybe it will help to know that she's not interested in boys at all... We're going to let you have one last orgasm while watching us together before locking you up in chastity. From now on we'll be controlling your orgasms so you don't turn into a chronic masturbating pervert. (Click to see more of Alexandra Snow)
Length: 9 minutes
Orgasm Control For My Boy
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
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
Teacher Supervised Masturbation
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)
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
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