Milf
Sissy Boy Wanked Before School
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
My Boy Won't Be Gay
To ensure her boy doesn't grow up to be a homosexual, a strict, church-going "MILF" takes matters into her own hands. A little bit of disciplinary spanking puts her boy in his place before she shows him how good it can feel to cum by a woman's hand.
Length: 13 minutes
Slow Loving Sex Ed
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
My Boy Will Learn To Worship Pussy
Before my boy goes off to college I decide to teach him about the birds & the bees. Who better to teach him than the loving mature woman who raised him to respect women? Today's lesson is primarily about learning to please a woman with his mouth. 1st I give detailed instructions, then I have him practice until I have a 100% real orgasm (not a fake porn orgasm). I then reward him by showing him what fellatio is & finish him with a hand job. The message throughout is to respect & worship women. To use his cock, hands & mouth to please a woman FIRST. Lots of SEX EDUCATION & real-world training on being a good lover & a gentleman.
Length: 23 minutes
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
Cum For MILF's Friend Ceara
Be a good boy & show Ceara how well trained you are. Show her how good you are at worshiping feet & cumming on command... (Click to see more of Ceara Lynch)
Length: 5 minutes
MILF's Strap On Discipline
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
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
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