Milf
I always wanted a little girl, not a boy...so I dress my boy up like a girl. Before sending him/her off to school I milk him to ensure he doesn't pop a woody at school, which would raise some questions. While stroking him I tell him how I'll have to train him to be the perfect cock sucker in case a man tries to diddle him. That way he can keep them from going into 'her' panties by making him cum in 'her' mouth.
Length: 10 minutes
This is a gentle, sweet instructional situation with an intelligent, sexy "MILF" who wants to ensure her boy grows up to be a good lover. She catches him playing with her dirty panties which prompts her to take matters into her own hands. There's a long, slow teasing build up, lots of light touching through his shorts...a little sensual foot worship (where she explains he should worship a woman's foot like he would lick her pussy)...she demonstrates good oral skills, explaining the similarities of a penis & a pussy...she then shows him how to use a condom correctly & helps him get used to the sensation of intercourse while wearing a condom. All the while he is instructed to control his orgasm, he's edged & encouraged to take his time & enjoy the experience. There's no rush. There's a nice long hand job at the end where he's edged & teased...eventually erupting in a long built-up orgasm. He's lovingly chastised for not asking for permission as he was instructed. She continues to stroke his sensitive cock a little as punishment while he squirms & giggles. She teases that she'll smear his cum on her pussy & make him lick it off. It's light, loving, kinky discipline. He's left feeling that he has to work a little harder to please "MILF", & he has a lot of practicing to do, but he's in good hands with a experienced mature woman who takes a keen interest in his education. (This is a custom vid. I use the name 'Tommy' a few times.)
Length: 22 minutes
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
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
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
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
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
For all my MILF's Boys and Ass Lovers!
Length: 7 minutes
Sexy Veronica! This clip focuses on her, her legs, her boots, her pussy...we chat while she uses a slave as a foot stool. Candid, unscripted and casual.
Length: 7 Minutes
(By special request from one of my special MILF's boys.) I catch you hiding in the shower trying to peek at me (your MILF!) while I go to the washroom. You get a stern talking to before I dish out your punishment: you'll be on special toilet duty until further notice! You'll have to be my toilet paper and clean me up perfectly each time I go to the washroom. Get started right now young man.
Length: 5 minutes