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."

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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." 

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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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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"

Caught With My Bras

"Caught With My Bras"

This was a custom order - name not used. To submit a request, email me at diane (at) insatiablemilf (dot) com. Please submit a full and detailed request for my review.

I know you thought I wouldn't find out, but you should know better by now. I caught you when you were stealing my panties, and now my bras too!? What is this obsession you have with my undergarments?

If you don't want to tell me, then you're going to be punished. Well... punishment it is then.

I have strict instructions for you throughout. I'm going to count you down, and maybe I'll let you cum, and maybe I won't, that's entirely up to me. When and if I do finally let you cum, you have only one place to empty your load...

You had to know there would be punishment for stealing your mother's bras!

Cum Eating Instruction - Diane Andrews

"Introduction To Making Your Cock Grow Bigger"

Taboo - MILF - Momma's Boy - Fantasies - Role Play - Cougar - Mom and Boy - Masturbation - Small Penis Encouragement - Big Tits - Cum Eating Instruction - JOI - Jerk Off Instruction - Masturbation Instruction - CEI - Bathtub Fetish

Honey, I know that you are growing up and getting bigger, but that there are parts of you that aren't catching up quite as fast. I know that you watch me sometimes when I bathe, that's why I leave the door cracked for you sometimes, because I kind of like it, but I also know that your penis is rather small for your age, but not to fret, I've done some research and there is a way you can make it grow bigger. You will have to be dedicated and diligent, but this will work. It starts with eating cum. We will begin with your own, and possibly even mine, and also your father's. He has quite a large penis, and eating his cum will just bolster your growth rate that much more.

I'm going to take an initial "soft" measurement. Don't worry, most men are small when they are soft. Now we have your measurement while soft, but I also need to know how big you grow when you're hard, so let me help make that happen. I know you love mommy's wet, soapy tits (that's why you watch me in the bathtub) so we'll begin there. Well, that's making it a little harder, but I want it as hard as it can possibly get. What if mommy masturbates in front of you, would that get you hard as a rock? Good. We will try that! Now you're hard enough we can take a good measurement. Ohhh, that's good! But, we can do better. Maybe if you eat mommy's cum it might help as well, so here, lick this clean.

Well, now we need to make you cum so you can eat it, this will be the first step in making your cock grow as big as we can get it. What if I masturbate again, and this time stick this part of this toy in my ass? Ya? I figured you would enjoy that!

Now remember, when you cum, you need to cum in your hand and eat every last drop so you can grow that cock nice and big for mommy!

CEI MILF Diane Andrews

 

Diane Andrews MILF