We are former high school classmates who dated in school. We meet after many years at a reunion. I’m married and a success in my business – have even started discrete dating, since wife no longer wants sex.
You start flirtatious – “Remember me? We dated a bit in school. So impressed that your business has turned out well. I always knew you were smart, and determined to make it.”
I react to your flirtatious behavior. “[Smile] I see you do remember. Can we get away from the group to somewhere a little more private?”
[Leaning in closer] “Actually I remember you quite a bit. You were the first guy to get his hands under my sweater. And what I really remember about that is that you came in your pants the moment you saw my bra.”
[More suggestive action – tracing your fingers over your breasts, opening buttons, showing cleavage]
“You remember, don’t you? I was ready to let you take my cherry that night – and instead you made a cum mess in your pants. At first, I guess I was flattered you liked me, but then it started to happen every time – and I began to notice you didn’t want to take my bra off – you wanted to look at at it – and touch it.”
[Blouse/shirt open now – just bra]
“You are starting to look embarrased. You remember all that too. It took me some time but I began to realize you were a bra pervert. You were a total pervert. And you still are”
“Don’t try to deny it to me. I know who you are. I also know you have been dating – despite still being married. Yes, I know some the women you have been with. Actually, they say you are a decent fuck. I do seem to remember you had a nice cock. Glad you figured out how to use it.”
[A little sterner tone]
“If you think you can keep from cumming on the spot, bra pervert, let’s see that dick that the women are talking about. Go ahead, show me. Mmmm I can see you still are turned on by my bra. I know you want to cum on my bra. That dribble of pre-cum is giving you away. Well – I think that might be arranged – for old times sake – but on my conditions.”
“Does that surprise you? After all, I do know your past – and your filthy perversion. You would not want that getting out. And I am ready to help you with your disgusting needs. Provided – no more dating – you worship me as I know you always have.”
“Stand right here – pants down – and show me that hard cock. You may worship my gorgeous bra – touch it – gently – softly. This is your mistress. Now – if you want what you have always wanted – you may cum on my bra – and only on my bra – from now on. That’s a good boy.”
Forgot to mention that I would like the bra to be sheer – so I can see the nipple through the sheer fabric. And intersperse into the suggested script with comments/ actions like “You are such a perv – trying to stare at my nipple.” “You adore the way the sheer fabric clings to the curves of my full breasts.” “You are already thinking about your cum on this bra, aren’t you?” “You would rather jerk off staring at my breasts in this bra than fuck me, you sick perv.”

BRA FETISH, HOME WRECKER, HUMILIATION, JOI, BIG TITS, FEMDOM

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.
“Background: All of your son’s neighborhood friends, like to come over to your house because they love watching you clean. You always dress sexy, low, low cut tops, either very low cut bras, i.e. demi-bras, or no bra, and very short skirts, nylons and garters are a plus, love the smoky/black very sheer nylons…. You make sure to bend over in front of the boys so they can see down your top, gently swaying/jiggling your tits for them to enjoy. When you clean shelves you have your back to them so they can see your skirt ride up, or cleaning the ceiling fan, stretching in front of them, facing them so they can see the front of your sheer panties. All, very slow and erotic, mommy enjoys being admired by these boys.
Mommy is extra horny today, daddy left yesterday on a business trip and mommy didn’t get her quota of morning sex.
Mommy makes comments to them such as: are you enjoying the view, do you like what you see, does that make it better (pulling blouse open a bit more and pulling up front of skirt so they get a clear view of your panties)
Mommy becomes more and more blatant about exposing her body to them as she’s cleaning. As she gets turned on, she asks them if they know what fucking is. Of course they all turn red, especially your son, hearing you say such words. Mommy presses the issue, then asking them if they want to know what fucking is.
Mommy decides to show them, swearing them all to secrecy. She leads them al into her bedroom where she undresses, slowly, talking about her tits, what happens when she gets pregnant, her pussy and how it is gonna be used during sex. You have them take off their cloths also, after all, it’s not fair for them to see mommy naked but she can’t see them.
After mommy tells them all about tits, function and erotica, and her pussy, in detail. She takes out a small lifelike cock, hopefully you have one, to demonstrate how a mommy makes love to a cock. Talk about blowjobs, demonstrating, and one of my favorites, titty fucking, then, after she gets the cock all nice and hard, she demonstrates how a mommy gets pregnant by a daddy, slowly rubbing it up and down her pussy, actually showing them, then how it goes into a mommy’s pussy, goes in and out, slowly, then when daddy shoots his white, sticky, cum into mommy’s pussy, she can get pregnant.
Explain to all them that that is how they were made, their mommy’s took their daddy’s cocks, made them hard just like I showed you then she fucks him.
After answering all their questions mommy sends them home then takes her son back into the bedroom to let him practice on you how to make babies. Remember that I like dialog, the more the better, especially the very graphic uses of tits, pussy, fucking, and blowjobs.
While in bed with your son, you talk again about all the things you covered with them, and how you really like showing off for his friends. Then mommy has her son get on top of her and fuck her.
Please, no loud screaming, “here I cum, etc? I like soft quiet talking and gentle body shaking, it’s obvious that mommy has an orgasm.
Cooling down, mommy asks him how he enjoyed fucking her and if he would like to see her fuck each one of his friends while he watches, yes, I am a devout voyeur.”

MILF, SEX ED, MOMMAS BOY, TABOO, ROLE PLAY, DIRTY TALK

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.
“For my second video, I would like you to act out my favorite fantasy. It’s summer and we are sitting in the front room with the door open and just the large old fashioned screen door. We are sitting on the couch, you and I and my brother who is nursing at your breasts. I am always there when you nurse my brother because I love seeing your tits. You know this and make sure to make a big scene out of exposing your breasts in a very slow erotic way, never just one, as most mothers would do, but both so that I have an unobstructed view of your bare tit. You have me keep a wash cloth close so that I can catch any drips from the non-nursing breast. You like for me to hold your tit while I wipe the nipple and of course I make it last as long as possible.
Eventually you tell me that it’s okay to just hold momma’s titty, she likes for her men to appreciate her assets.
While nursing, you talk to my brother about me and your bare tit. Things like, “you see what your big brother is doing, he’s holding momma’s titty in his hand,” and ” he likes watching momma feed you and stare at momma’s titties, etc. A nice running commentary about me liking your naked titties.
A little while later, the paperboy comes to the door to collect. You tell him to come on in and ask him what he wants. You ask him if he can wait till you finish feeding my brother, and of course he doesn’t mind at all. He obviously stares at your tits and develops quite a bulge in his pants, no huge cocks, just normal for a boy. You decide that maybe he needs a nice tip for waiting for you to finish.
You begin asking him, “do you like looking at a woman’s titty?” “have you ever seen a woman’s titty before?” “would you like to touch one?” “I’ll let you but you have to do something for me.” Here you talk him into taking his cock out so you can see it.
Now mommy gets really slutty and puts on a show for her sons. Mommy uses cock, pussy, fuck, titty a lot. She offers to pull up her skirt so all the boys can see her pussy. And, please, expose your pussy, just a little for us to see. Asks the paper boy has ever fucked a woman. She tells him about her exploits around the house for her son, me, like cleaning naked, letting me touch you anywhere and whenever I want. Sometimes coming over to the couch while I am watching TV and sitting on my lap facing me straddling my legs pushing your tits into my face, rubbing your bare pussy on me, etc…. And sometimes, when daddy is away, I get to sleep naked with mommy all night.
Eventually you ask the paperboy if he would like for you to suck his cock. Of course he looks startled, and you explain, in explicit detail about women sucking cock. Putting it in your mouth, licking it, rubbing it all over your face, a scene that I find totally erotic in porn videos.
Don’t spend a lot of time with head down, making slurpy noises. The talk is the most erotic for me and of course seeing your body. Head down for a couple of seconds, up and talking to your sons, like “are you watching mommy suck cock? Did you see mommy put his cock right in her mouth, just like she does yours? Etc….
After he comes, you tell me to hurry up and get naked and lets go to bed, mommy needs your boy cock right here in her pussy,
Remember, slow and sensual, with lots and lots of dirty talk by mommy”

MILF, LACTATING, MOMMAS BOY, TABOO, ROLE PLAY, BIG TITS

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. After catching mom cheating with the neighbor, you decide this will be the optimum time to use it against her to get what you want. After joining her in bed for a “nap”, you wake her by lifting her nightie and touching your cock to her ass and then tell her if she doesn’t do what you want, then you are going to tell your father about her fucking the neighbor. Reluctantly, at first, she agrees to go along with it, but then realizes your cock is much bigger than your father’s and ultimately is consumed with passion. BUY NOW to experience the ultimate in MILF, Taboo, Mom/Son, Older Woman Younger Man, Cougar, Mommas Boy, Big Tits, Pov Sex, Blackmail fantasy, Cock Lust, Big Cock, Virtual Sex and the most erotic sensuality and sultry fantasy fulfillment with ME!

BLACKMAIL FANTASY, MILF, POV SEX, ROLE PLAY, TABOO

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.
There you are again peeking at me through the keyhole in the door while I begin to undress for my shower. Again I know it’s wrong, but the idea of you spying on me such as you do makes me excited. Come in here and let’s do something about that.

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

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

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

“If you could wear hosiery and of course something showing your boobs. You will be sitting on the bed talking down to two of the neighborhood guys. You are asking them how come they are always hanging out at your house instead of being outside playing with all the other guys. Hmmm you say you think you know why. They have heard the rumors and they want to see it! They are confused how you are such a beautiful woman but could actually have one of those. You say well I don’t know. You guys may not be ready yet.
You think about it some more and say well okay but you have to keep it a secret and they have to do and say whatever you tell them to. They agree so you begin by telling them they have to call you mommy. Don’t worry about why just do it. Now ask mommy if she will show you her tits. You smile and pull them out. Now ask mommy if you can see her lady cock. They ask so you pull it out and begin to stroke it. I bet its much bigger than yours. Lets see. Pull out those little cocks so mommy can see. You smile. You lean your hips towards the camera and down below it and tell both of them to rub it. It will be mostly out of view below the camera You begin working your hips and moaning as they stroke you. That’s good. Stroke mommy’s cock. You reach down and briefly rub theirs. See we can help each other. Doesn’t it feel good when I stroke your dicks. You start getting real horny. You choose the shorter one. You say okay tell mommy you want to suck her cock. That’s a good boy. You look over at the other one and say no I want him to suck it. I have something else planned for you since you are bigger. Did you know you have a pussy. Oh yeah. I’ll show you in a minute. Okay first let me kiss you so you lean down and kiss him. Now kiss mommy. Open your mouth and let mommy put her tongue in there. You kiss him. Then you stand up and say okay open your mouth for mommy’s cock. Slide the strap on down below the camera like it is going in and out of his mouth as you work your hips. It feels so good. Moan a lot and tell him how good his mouth feels. He’s such a good cock sucker for mommy. You do this for a little while but then pull out saying whoa I don’t want to cum just yet but don’t worry mommy is going to let you swallow her cum. Be patient.
You look over at the bigger one and say lay down on the bed and pull your legs way back. Mommy’s going to show you how to use that little pussy. The camera changes to where it is looking right up at you. You begin pushing your strap on into him. Working your hips. When you are done pushing it in the strap on will actually be out of view. The rest is virtual sex. You over the camera pumping your hips. You look at him while you fuck him smiling and moaning. You talk dirty. Do you like it when mommy fucks your tight little pussy. Tell mommy to fuck you. You kiss him several times as you fuck him. You look over and talk to the other one. See what I’m doing? Don’t worry your time will come. This goes on for a while (make sure your boobs are out). You begin to realize you are about to cum so you pull out. The camera changes as you walk over to the younger one and push your cock down below the camera again working your hips. You are so close you order him to finish you off. Make you cum. Suck all the cum out of you and orgasm while he swallows it. You stand back holding your cock smiling and say what good boys you are. Now remember this is our little secret.”

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

Continue to download