Diamond has been noticing her son looking at her very strangely. Then, as she is exercising in her room she feels his eyes on her. She starts to scold him but realizes it is natural for sons to have…feelings, especially at his age. She is his first crush and she wants to handle it the right way

TABOO, MILF, COUGAR, OLDER WOMAN / YOUNGER MAN, SLUT TRAINING, DOMINATION

Continue to download

Mom is going to visit her gynaecologist and asks son to sniff her cunt just to be sure she smells good. She imitates a pose like on a gyno chair so the boy could sniff her gorgeous cunt well. But of course she knows that would turn him on again! The view of that fantastic big labia pink mature cunt, wide open stunning legs and her dirty talk make him wank and cum before she leaves to the doctor. Oh, and one more thing please – would you pee all over me Mom! I need to feel that divine liquid all over me again!

PEE, MOMMAS BOY, TABOO, OLDER WOMAN / YOUNGER MAN, ROLE PLAY, COUGAR

Continue to download

This was a custom order – no name used. To submit a request, email me at diane (at) insatiablemilf (dot) com. Please submit a full and detailed request for my review.
What do you think you were doing spying on me like that? Don’t you understand that’s wrong? I mean, I’m your mother, you are not supposed to look at me that way! Maybe I’m so angry because… well… maybe I liked it. I did. It actually turned me on a lot to know you were looking at me that way. Do you really want to know what it would be like to experience your mother’s body?

MILF, COUGAR, POV SEX, TABOO, ROLE PLAY, BIG TITS

Continue to download

This was a custom order – name used. To submit a request, email me at diane (at) insatiablemilf (dot) com. Please submit a full and detailed request for my review.
“I was interested in a POV video with you playing my tipsy mother coming into the living room from the party outside to unknowingly seduce me over a longer period of time. I was watching some TV while drinking on the couch and you decided to join me. We talk with each other for a bit, talking about what drinks we like. Then it moves on to talking about the party and how everyone was checking you out. I try to move on from the subject. [Silence]
You make a couple drinks for us to have. Then after drinking you feel buzzed and start checking me out. You ask, “Honey, you remember that talk we had a long time ago about , when you said people should be able to make love to whomever as long as their adults and consent. I remember I disagreed with you and said that sex between family members is not alright at all, do you remember?”
ME: Yeah
MOM: Well, I have been thinking about it…. a lot.” [Pause]
ME: Okay, what about?
I mean, I have been umm … you know…umm…thinking about it…late at night.”
ME: Ummm what do you mean?
MOM: I have been thinking about how you might be right.
ME: Mom?
MOM: I have been thinking about what your cock looks like ….. and if it would feel good for me to touch it.
ME: What the fuck Mom? Umm, ummmm we can’t and there are so many people outside anyways.
This is where you seduce me by slowly assuring no one is going to come in from the party and you want to just look at it. You slowly pull me out of my jeans [no cock in video plz], You smile and then grab it, seducing me to be able to suck it to completion in your mouth. [2 minute bj]
After cumming in your mouth and you swallowing it. You dress back up and drink to clear your throat. Someone comes in from the party [no actor needed] to grab some beers and quickly leaves which is good because we act kind of awkwardly silent watching TV. After partier is gone back outside…
MOM: Did you like that?
Me: omg…yes.
MOM: I am so fucking wet for you Samuel. Are you still hard?
ME: Yes, but we shouldn’t.
MOM: [smile] You know you want to.
You seduce me quickly and pull me out of my jeans again and move your panties over to the side from under your skirt , climb on me and take control riding me and then urging me to come inside you eventually. [4-5 minute sex] [Toward the climax, plz pull out your beautiful breasts and ensure me that you don’t care if anyone comes inside.]”

MILF, COUGAR, POV SEX, TABOO, ROLE PLAY, BIG TITS

Continue to download

Another installment to the ‘Keep It In The Family’ Series. Milf mom comes home after a filthy feverish fuck session with her son and two lifelong best friends. It started off innocent. Bringing the boys to the amusement park for a day of fun. Things seemed a bit suspect, like her skirt flying up in the wind riding a roller coaster and the friend sitting next to her copped a feel. At the time she thought he just did that on accident since the ride was so jerky. Later she realizes… no it was not. After a steamy hot karaoke session she realizes the boys have been hitting on her… and that she kinda likes it. To remain appropriate she goes to the car for the rest of the outing and takes a nap in the back seat. What she wakes up to was a sworded surprise too wrong for words.

AGE PLAY, COUGAR, MILF, OLDER WOMAN / YOUNGER MAN, TABOO

Continue to download

I went to my friend Ronnie’s for the weekend and his mom picked me up at the bus stop cause Daniel had to work. When she picked me up she looked sexy as ever and she started asking me about my life and my girlfriends. I explained that i am struggling cause I am a virgin and not really sure about how to act with girls. She started coming onto me and said that she could help me out and give me some pointers. On the way to the house she wanted me to fondle her breasts and she said it would be a good idea for me to get use to getting my cock felt up in the car. When we got into the house she started touching me all over and dropped to her knees and started pulling my cock out. I was amazed how good it felt and after a few minutes of sucking my dick she lead me to her bedroom and stripped off all of her clothes and we had hot passionate sex. After the sex she told me she knew all along that I was not a virgin as she was aware of other older women that I fucked.

MILF, OLDER WOMAN / YOUNGER MAN, VIRTUAL SEX, POV, COUGAR

Continue to download

This was a custom order. To submit a request, email me at diane (at) insatiablemilf (dot) com. Please submit a full and detailed request for my review.
You’ve been away at college for so long, and mommy misses you so much! It’s time for our weekly cam session, and much to your delight mommy is wearing the sexiest outfit you’ve ever seen! She is obviously ready for something extra special and fun… and after the usual pleasantries are exchanged, you find out exactly what she has in mind! It’s the filthiest, raunchiest, dirtiest cam session you’ve ever had with anyone, especially your own mother!

TABOO, COUGAR, MASTURBATION, MILF, DOUBLE PENETRATION, SOLO MASTURBATION

Continue to download

This was a custom order. To submit a request, email me at diane (at) insatiablemilf (dot) com. Please submit a full and detailed request for my review.
“My idea is kind of a version of your clip Mommy’s Again. You are a divorced mom home alone and you have been drinking all day and you are and very horny. You have a college age son who is home for the summer but has left for the weekend. One of your son’s friends who you have always wanted to fuck stops by to see your son. You tell him he’s not home but you realize that this is a perfect opportunity to seduce him. You ask him if he thinks you are pretty and if he likes your big tits. You have him drink a couple drinks with you and then you tell him since he’s been drinking the only safe thing to do is to have him spend the night and if he’s going to spend the night, then you might as well have some fun. You tell him how much you like to get fucked when you’re and you unbutton your shirt to show him more of your cleavage which was already very prominent. You notice his cock is getting very hard and you ask him if you can see it. He pulls it out and you touch his dick marveling at how big it is and you tell him again how much you like to fuck when you’re and how you’ve always thought he was handsome and what a waste it would be if he didn’t put his cock in your pussy and fuck you. You tell him how awesome you are in bed when you’re and that he should take you to bed right now and fuck you all night. The next scene is you in the bedroom on your back getting fucked and telling him how much you like getting fucked by his huge cock. When he’s ready to cum, you tell him you want him to pull out and cum all over your stomach and tits. You are very happy he has such a huge load of cum and make arrangements with him to come over and fuck you for the whole summer whenever you get which is a lot. If you agree to this, could you please wear either the red shirt and red bra you wore in Mommy’s Again or the blue lingerie you wore in several of your other clips? Also, you should be barefoot for the entire clip if that is ok. I think you are absolutely georgeous!”

MILF, COUGAR, POV SEX, TABOO, ROLE PLAY, BIG TITS

Continue to download

You just got a great deal on an apartment. Although you’re barely 21, it’s in a 55+ living complex. All you have to do is attend to the resident’s minor home repair issues. Mostly it’s just fixing light fixtures or moving heavy stuff, but today was different. There’s this one woman – she can’t possibly be 55, can she? – who has been giving you serious bedroom eyes ever since you moved in. Your units are only a few doors over from one another, and you can’t help notice that she has a lot of, um, gentlemen callers. Even so, when she asks you to come look at an issue with her bed, you don’t think it’s anything suspect. Even after you come in, and she’s all flirty, wearing a tight outfit, telling you how strapping and strong you are, you don’t think she wants to…well.
You check out the bed. She says that it squeaks something terrible, and gets on to bounce the mattress and demonstrate, to not avail.
“You know,” she says, smirking, “it’s normally when it’s two people, so why don’t you get on here with me, so you have a better understanding of where the issue is?”
Even then, you don’t see what’s coming next…when she climbs on top of you and starts to bounce. You can be really thick sometimes…and it doesn’t take much of this sexy cougar bouncing on your lap to make you really get thick! Once you notice how hard you’re getting, you try to wiggle away but she doubles down, bouncing and grinding on you, and you realize this was her plan all along! Before you can say “senior discount,” she’s got your cock out, working it into her wet and hungry pussy. You’ve never seen a woman so self-possessed, so sure of what she wants…and what she wants is you, deep inside her milking quim! You watch as she bounces on your cock, making herself cum onto your straining dick, begging for your cum…

Category: VIRTUAL SEX
Related Categories: MILF, ROLE PLAY, DIRTY TALK, COUGAR, POV

Continue to download