Auntie Caught You Spying

Auntie Caught You Spying

You're a curious little one, aren't you? At the family's fourth of July party, you hear noises coming from auntie's bedroom, so being the little pervert that you are, you go check it out. When you see it's your auntie masturbating, you stay down low at the end of her bed and watch. Inevitably, she catches you and yells at you to get out!

Just as you were thinking she wasn't going to say or do anything, she calls you into her room to have a little chat about what just happened.  You figure she's going to give you the typical lecture on how you're not supposed to go into people's rooms when the door is closed, but instead she does something very unexpected!

Here's the deal, since you saw me masturbating, you are now going to masturbate for me, and I'm going to make you eat your cum at the end. You have two choices; you can do it, or I can tell your mom what a dirty little pervert her son is for spying on his auntie. That's what I thought...

Now here are the rules; follow them to the letter. At the end, you're going to come in your hand and eat it for me. Every - last - drop. If you can manage to do as I say, maybe someday we can do more!

Includes: MILF, Taboo, Aunt, Older Woman Younger Man, Cougar, Role Play, CEI, Cum Eating Instructions, Blackmail Fantasy, Masturbation Instructions, Sensual Domination, femdom POV and Diane Andrews

Lick It Clean Lace Bra Lover

Lick It Clean Lace Bra Lover

This was a custom fantasy fulfillment. To be considered, email me at diane (at) insatiablemilf (dot) com

"I was thinking in a vídeo with you wearing my favorite lace bra (img below), teasing me with my fantasy of fucking it with A LOT of humiliation and CEI. Always looking straight at to me in an intense humiliation clip, with a mean and disgusted ton.

On this clip you can refer to me as LACE BRA LOVER,  LACE BRA SLUT, LACE BRA BITCH, you choose goddess, I'd when you call me those names so you can use them a lot

The first five minutes or so you 'll make me hard showing me all the details of your lace bra ( back, straps, the lace cups)and while you're doing that u could start humiliating me for being such a lace bra lover. You know how much your humiliation turns me on so you can be harsh with your words, no limits

At this point, your lace bra lover is super hard and my biggest fantasy is to fuck that lace bra while you keep humiliating me. Today you're going to fulfill my fantasy and you're going to allow me to fuck my favorite lace bra while you shake your tits.

You could say "put your cock on my bra and fuck it, lace bra lover. Fuck while I shake my tits. That's it fuck my lace bra lover. Keep fucking my bra while I humiliate you for being such a bra slut. It feels so good your cock on my bra. I'll keep shaking your slut"

The more I fuck your lace bra,  more you'll grab and shake for me and more humiliation I'll have.

You keep humiliating/shaking/ grabbing and telling me to fuck my favorite lace bra over and over (Always encouraging me to fuck it harder and harder with you humiliating more,  being really bossy) till you think I'm ready to cum.

You 'll allow me to cum all over your lace bra  But only if I lick it all after, So you shake your tits in my face telling me to fuck it and cum all over it. Like a good lace bra lover.

You could straight at the cam and say:

"That's it lace bra lover, cum all over my bra, empty those balls on my lace bra, make it dirty. Look at my tits shaking and cum all over my lace bra"

Cum Loving Sweater Whore

Cum Loving Sweater Whore

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.

"Start off wearing the just the pink sweater and sweatpants and also keep your hair down. 

Humiliate, degrade me and call me names throughout the entire video.

Feel free to call me names like sweater slut, sweater whore, cum slut, sissy bitch, cum dumpster, etc. 

Talk about my sweater fetish and how much I love seeing you in this outfit.

Talk about how I would rather jack off to you fully clothed than in lingerie or fully naked. 

Talk about how hard my dick is from this. 

Begin giving me some JOI, have me jerk at different speeds and edge building up a big fat load of cum. 

Tell me what you think of my sweater fetish and fleece fetish. 

Talk about how I am wearing the same thing as you while I'm jacking off.

Show off your sweater and sweats and tease me with them.

You can tell I'm loving your sweater but you know I want more.

At this point pull out your fleece jacket and have it in your lap. 

Tell me to pull out mine as well and put it on as you are putting yours on. 

For now only zip it up to your breasts. 

Tease me plenty with your fleece jacket and talk about how much more excited I am and how badly I want to cum now. 

Show off your jacket top to bottom and also from the back side. Stick out your ass a bit so I can see the fleece jacket hugging the top of your ass. 

Talk about how the jacket feels. 

After teasing me some sit back down so I can see your face and entire jacket. 

Tell me that you know how much I love to eat my own cum and that's exactly what I'm going to do for you. 

Tell me what you think of cum eaters especially those that eat their own.

Humiliate me for wearing women's sweaters, fleece, sweatpants and jacking off and guzzling my own cum. 

Talk about cum and how it tastes, smells, the texture, etc. Also feel free to use the words sperm and semen when talking about all of this. 

Continue giving me JOI telling me to jack off to you and your fleece jacket. 

While giving me JOI zip your jacket all the way up to the top and tell me to do the same. 

Tell me that you know it's my favorite way to be worn and you know how submissive it makes me feel with a fuzzy collar zipped around my neck. 

It's time to cum so have me get into the cum slut position laying down on my back and flipping my legs up over my head getting my rock hard dick as close to my mouth as possible. 

Tell me to open wide and I better not cum until you say. 

Before you give me a countdown while I'm in this position really drive home and tell me exactly what it is I'm about to do. 

Give me a countdown from 10 and at the end tell me to shoot all my hot fresh cum straight into my mouth. 

Tell me not to swallow just yet, have me close my mouth and sit up and look at you. 

Talk about how big of load is in my mouth, humiliate me for what I just did, talk about the cum and how it tastes and how thick it is. 

Say things like did you enjoy jacking off into your mouth you filthy sweater whore, you like the taste of your own cum.

Eventually allow me to swallow and talk about how warm and cozy I am in my sweater and fleece with a belly full of hot fresh cum straight from my dick." 

BUY NOW to experience the ultimate in Sweater Fetish, Masturbation Instructions, Cum Eating Instructions, JOI, Jerk Off Instructions, Edging, CEI, Humiliation, Femdom and the most erotic sensuality and sultry fantasy fulfillment with ME!

You Found My Dirty Pictures

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Panty Thief

Panty Thief

This was a custom order. Email me for your own custom clip: diane (at) insatiablemilf (dot) com.

I want to have a talk with you. I was cleaning your room earlier and decided it was time to clean under your bed when I found all these pairs of my dirty panties! I had been noticing certain pairs were missing lately, and I could not figure out where they went! Now I know. It's been you, stealing them. Why would you steal my panties? All of my bras and panties are matching sets, so you can imagine my shock when I found my own son has been stealing them!

Have you been smelling them and jerking off to them? Well, if that's what you want, then you can just do that right here, right now, for me. If you're brave enough to sneak my panties from me, then you can be brave enough to jerk off to them in front of me, too. You even stole my crotchless panties, and you know exactly when I would wear those. It's when I am with your father, so obviously you love the smell of sex on me, too. So, I have a special surprise for you. 

Get on your knees in front of me. You're going to sniff and lick and smell these pairs of panties you had hidden under your bed, and then, the panties I've been wearing; the ones I put on after I had sex with your father last night and he came inside me, and then his cum dripped out into my panties -- I have those for you right here, right now and you're going to smell and lick them while you jerk off. Look at you dripping with excitement!

Now be a good boy and cum in your hand and eat it. If you can manage to do that for me, you can have this pair of panties as a reward.

Includes: MILF, Taboo, Fantasies, Mom/Son, Older Woman Younger Man, Cougar, Mommas Boy, Panty Fetish, Panty Sniffing, Cum Eating Instruction, Humiliation

Sissy Tea Time Rehearsal

Sissy Tea Time Rehearsal

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.

"Dear Ms. Andrews could you please make me a custom named "Sissy Tea Time Rehearsal" In this clip you force me to wear panties and a garter belt and stockings. You have set up a tea time play date with me. But instead of letting me drink my tea, you humiliate me and force me to stroke my clitty into the tea cup for your amusement. You tell me that I'm just a porn addicted, perverted sissy masturbator with a tiny clit instead of a cock. You make me stand up with my clit over the cup full of tea and you instruct me to stroke that tiny clit with two fingers while you smile, laugh and enjoy your tea. You let me know that this is a rehearsal and that the real tea party is next week. At that time you're going to make me do this in front of all you girlfriends. They will take pictures and post on social media. You instruct me to keep my pinky out, reminding me that it's a tea party. You demonstrate while you drink your tea. If there is pre-cum you make me take my pinky and wipe the tip of clit, then you force me to ask permission to suck it off my finger. When we get near the end, you make me rub my clitty faster and faster, but I am to slow down if I feel I will cum. You repeat this over and over until I ruin my orgasm into the tea cup with a very slow light stroking motion. The slower I can go and still cum, the more you praise me. Then, of course, I have to drink the tea. Please remember to humiliate me the entire time, talking about your girlfriends, how they will enjoy it."

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My Sissy Boy

My Sissy Boy

This was a custom fantasy fulfillment. To be considered, email me at diane (at) insatiablemilf (dot) com 

"What I'm thinking is it'd start out with you peeking through a

crack in the door and then you open it and say son what is going on here?

You will have caught me on your bed looking at dirty pictures of

you while I'm jacking off with your worn panties and maybe sniffing or

tasting the toy you left laying around.

You're upset with me, but you also understand boys have needs and

desires. You tell me it's ok to masturbate but not to steal your

stuff to do it. You're going to let me finish what I started, but you are

going to watch and when I finish I'm going to have to do it into my

(or your) hand eat all of my dirty hot sticky cum.

You tell me to go ahead and start masturbating my penis and as I do

so you're surprised to see it's very tiny. Daddy's is very big so you

can't believe how small mine is. You tell me to rub it harder so it

grows. I try, but it just won't get hard for me and it's still so

tiny I'm about to cry. You think I may just need something to look at so

you take your shirt off and let me see your breasts in person. That

helps me a little and I rub faster but it's still not enough. You

go ahead and take your bottoms off and let me see and sniff your pussy

as you spread it, then turn around and do the same with your butthole.

I like it a lot and tell you it's pretty, but I'm still not fully

hard.

You sit down next to me and tell me it's ok but you need to ask me

a few more questions. You know that I must like girls because I was

sniffing your panties and looking at the nude pics daddy took of

you. You have a sneaking suspicion though that I might be at least

partly a sissy boy. Did I try wearing your panties? After all my penis is

very small, and would look cute in them. And you did catch me tasting

your dildo. You ask if I just wanted to see what you taste like, or if

secretly I wanted to see what it was like to have a penis in my

mouth.

All of that talk has an effect on me. My little dick starts to get

harder, by no means hard yet, but it twitches a bit. You think

maybe I like that talk about being a sissy boy and you have an idea. You

lube the toy up and slide it into my butthole

You gently use the toy on me and immediately you can tell I like

it. My penis is finally getting hard. Still tiny, but hard. You remind

me that I have to masturbate for you and when the hot sticky cum

shoots out of my small penis I have to catch it in my hand so I can eat

and savor my puddle of shame."

Continued Therapy

Continued Therapy

This was a custom fantasy fulfillment. To be considered, email me at diane (at) insatiablemilf (dot) com

A sequel to the highly regarded "Therapist Manipulation". Enjoy them together, or separately.

It's time for your next weekly session. I have zero tolerance for dirty masturbators, so this week we are turning things up a bit. I have several implements for you to use while I instruct you to masturbate in front of me. You will cum at my command, at my countdown, and at my instruction. Remember, you have no choice in any of this if you expect to keep your job, and this could go on, and on, and on as long as I please. This is only just the beginning...

"This is a continuation of the custom you made for me previously. This is my second therapy session and you have decided to up the humiliation a notch. You have no mercy for dirty masturbators. This time you make me strip down completely and put on nylon leggings and a tiara that says "Princess" on top. You also hand me an aneros toy. You make me put the toy in my mouth, spread my legs for you and begin masturbating my dirty little clitty for you. You smirk and smile as I'm forced to follow your instructions. Feel free to remind me that I have no choice and that this therapy may go on and on indefinitely. Please remind me this is just the beginning of what you have in store for me. Make me thank you (with my mouth full) and please make me repeat humiliating commands. Halfway through make me take the aneros out of my mouth and insert into my ass for you. Make me stroke with the two fingers and move the aneros in and out at the same time. Tease me about my man pussy and my stiff little clitty. Enjoy edging me repeatedly making me stroke harder and faster, but always with only two fingers. You can also make me take the aneros out from time to time and put it back in my mouth. You find this very amusing. When you are good and ready, make me remove the aneros from my ass and allow me to follow a long teasing countdown to an orgasm on the toy. Please make me clean the toy for you. Then show me your disgust and arranging for my next appointment."

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Diane Andrews: Therapist Manipulation

Therapist Manipulation

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.

"In this video I am an employee that has been sent to a therapist because porn was found on my computer at work. You play a professional yet sadistic Therapist. I must be examined by you and follow your instructions exactly if I am going to get my job back. As it turns out, you enjoy teasing and humiliating masturbation junkies like me. It gives you great pleasure to make me stroke for you in all kind of ways, following your instructions exactly. Also, feel free to make me finger my asshole for you. You make me repeat humiliating phrases about the size of my penis and about how I am a horrible pervert. You make me worship you beauty and declare that you have complete control over me. You examine my penis and balls and humiliate me for being small and inadequate. Every once in a while you remind me that you're in charge and I can't get my job back unless I follow your commands. Please bring me to the edge over and over again only to make me stop so you can smirk in my face. When you finally decide to let me ejaculate on your command you tell me that I can only cum if I squirt it directly into my pathetic mouth for you. You make me agree. Then, you instruct me to get into position and make me aim carefully, then you count me down and command me to squirt that load into my mouth!! You make me swallow and show you that it's gone. Then you calmly schedule my appointment for next week."

Doctor's Orders

Doctor's Orders

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. "It starts with you dressed in a medical outfit (no glasses). You tell me that I'm here for a mandatory routine medical exam. You tell me to not be shy and take of my clothes. When I do you are amused but try to be serious. You tell me to lift my penis and show it from all sides while you take a closer look. You note down that I am circumcised. You say something like "The penis appears to be very small, below average size" (while taking notes), still amused by it. You tell me to show my testicles and note "subject has very small testicals, well below average in size". You make an off-hand remark to me: "your balls are really tiny *grin*, sorry that was unprofessional". Your hand reaches towards my balls (below camera). You feel up my balls and say stuff like: "I have never seens balls this small on a grown man" "Do you cum alot? Do you cum at all?" "Are you even able to produce semen with these?" "Are you able to ejaculate a decent amount of semen?" "You know women like it when theres a lot of cum, a lot of semen cumming into their pussies!?" You say: "Well, we will find out today, but first we have to measure the girth of your penis". You take out an empty toilet paper roll and tell me: "The quickest way to measure penis girth is to use to toilet paper test" "If your penis fits into a toilet paper roll it is too thin and not able to pleasure a women" You tell me to get hard in a commanding voice. You slip the roll onto my penis. "Ah, thought so, you penis is way too thin, look how much room it has!" "Thin penis and tiny balls *grin*" You inform me that now I have to produce "a cum-load of semen", you tell me to stroke my penis in a commanding voice. You tell me to flip my legs over my head and point my penis at my open mouth. You say things like: "Come on, stroke your tiny penis, I want to see you ejaculate in your mouth" "Faster, I need a load of cum" "Do you feel the semen building up in your tiny testicals?" "Are you ready to ejaculate onto your tongue?" "Are you going to cum a gooey warm sperm-load for me?" "I'm going to give you a countdown from 10 to zero" You start counting down. On zero you say something like: "Ahh, let my see the how much you can cum". You act surprised by the amount of semen. "Wow thats a lot of sperm!" You command me to swallow my "warm cum load of semen" and grin when I do it. You wrap up by saying stuff like: "Thank you for your visit and thank you for gulping down a load of semen!" END"