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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

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

I have caught my boy looking at gay porn again. In an effort to put him on the STRAIGHT & narrow I combine 2 techniques: #1. I show him that he can be attracted to women by using my body & hands to arouse him. #2. I show him how awful it would be to be a fag by making him cum on his own face. If he were gay he'd have cocks & cum in his face & mouth all the time. I make sure that experience feels very humiliating & negative.
Length: 12 minutes

Custom vid: I tell you, my boy Johnathon, to rub my feet. I then tell you that I ran into your ex, Katie & that she's just married a great guy & she's really happy. I can tell this makes you sad so I encourage you to stroke your "little peeps" while you worship my feet, to make you feel better. I go on to tell you that your ex had just returned from her honeymoon & I could tell by the sparkle in her eye that she had had lots of great sex. A woman can tell when another woman is being sexually satisfied. I explain that you could never make her feel that way because your penis is too small. I gently tease you about still being single, living at home with me while your ex is having a great life with a real man who probably has a much bigger cock, a better job, etc. I encourage you to cum while kissing my toes, reminding you that your place is kneeling before me, at my feet.
Length: 11 minutes

Custom vid...I come home from work and tell you to rub my feet. I notice this arouses you and start to tease you about your foot fetish. I tell you that your F***** could walk in any moment and what would he think of you! I let you worship my feet as I tell you about running into your ex & about how happy she is with her new boyfriend. I confide that she seems very sexually satisfied & that must really hurt your feelings since she dumped you for having a small penis. I encourage you to stroke your little dick while licking my feet, gently teasing & humiliating you...
Length: 10 minutes

You're hot Aunt is visiting & finds out your marks have recently dropped in school. She figures out that you have a crush on your busty teacher making you so horny in class you can't focus. She takes matters in hand & shows you how to 'release the pressure'. She demonstrates various ways to masturbate, talks about lube, explains how to control your orgasm, etc. She tells you to look at her cleavage & that it's okay to fantasize about her breasts or your teachers breasts while masturbating. This will be our little secret.
Length: 12 minutes

You've been caught jerking off in the bushes by your hot Auntie. She teases you & encourages you to continue...coaching you along...
Length: 7 minutes

MILF/boy - Twisted Fantasy: Show me what an obedient boy you can be for me.
Length: 10 minutes

As part of your sex ed I've gotten you a masturbation device to practice with (it's like a Fleshlight). I know it seems a little strange to have me (your MILF) teach you this stuff but I want to ensure you have proper instruction...& I also know that you secretly desire me even though it's so naughty & wrong...
Length: 16 minutes