Cuckold Training

Enriching Your Sexual Education II

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.

"My other idea would be a followup.  The sex ed teacher calls you again the following night and tells you I was a good boy today. She worked with me personally in front of the class and I did a good job licking her pussy and stuck my tongue as far as I could in her anus and was eager to suck on it and that I didn't miss a drop when I ate my semen out of my hand. 

She goes on to tell you that tomorrow we start our unit on bisexuality, but before we start that because of my size issue she'd like to use my as an example and explain the concept of cuckolds. She'll tell the class some men have little penises and can't get a woman off in the normal way and they have to lick the woman while men with big dicks fuck them, then be sissy cuckolds and eat not just the woman's juices but the man's cum also. She also tells you she'd like to use me for the intro to bisexuality. You agree to everything she says and hang up.

You tell me what a good little boy I am and explain to me what's going to happen at school tomorrow. 

Tomorrow to start out one of the other boys with a big penis will put it in the teacher's vagina. While he's doing that I will have to tongue her anus like I did so well today. Any juices that come from her vagina I will have to lick up, and I will occasionally have to lick the other boy too. When he shoots his semen into the teacher it will be my job to eat it all out of her and make sure she's cleaned up. Also clean his penis with my mouth.

You go on to explain to me that the teacher wants to use me as the "bottom" in the lesson on gay/bi sex. I ask what that means and you explain I'm going to have to suck on the male teacher's penis until he ejaculates in my mouth (maybe some of the other boys too!) He's then going to some things with/to my butt. You explain that he'll have me spread it open and put some oil in the hole before he sticks his fingers and a penis shaped rubber toy in it. When it gets hard again he'll have me spread my cheeks open wide while he slides his penis into me and pushes it in and out until he ejaculates again.

You can tell I'm scared about this and you tell me not to cry it will all be ok and won't hurt me too bad, but you can tell I'm also getting a little erection hearing about it. Maybe I'm naturally a little dicked sissy. You tell me to take my pants off and we'll do a little homework to get me ready.

You get out a dildo, making it a point to say it's the size of most men's dicks. Much much bigger than what I have. Have me stroke my little thing for you you lube up my hole and start showing me what will happen tomorrow first with your finger then the toy. You can tell I really enjoy having things in my butt because my penis is much harder than normal. You tell me how when I cum I'm going to eat it again, but there's some extra involved this time. Go on like before with the small penis and cum eating talk, maybe also call me a sissy who just might like boys. After a couple minutes of that when I'm about to you'll pull the dildo out of me and have me shoot my load on it. It'll be dirty from having been inside me and also covered with my cum but sissies don't mind that you tell me as you put it in my mouth and tell me to clean it all up. When it's all cleaned up you tell me I'm a good boy and I'll do fine in school tomorrow."

Mom Son Sex Ed

Enriching Your Sexual Education

This was a custom order. No names used.

"What I'm thinking is you get a call from my sex ed teacher telling you that I didn't do my work in class today. The girls were supposed to pair up with boys and let them feel their breasts as well as smell and taste their vaginas and anuses. The boys were supposed to let the girls watch them masturbate into their hands and eat their own cum. The teacher says this is a required lesson and you tell her you'll help get me ready to do it at school tomorrow.

You sit me down and ask why I didn't do my schoolwork and tell me you don't want me to flunk out. I tell you that the girl I was with was very pretty and I thought her vagina and anus were very pretty and smelled and tasted good but I was too embarrassed to show her my tiny little boy penis. You are very understanding and tell me to take my pants and underpants off.

I do as you say and you tell me you understand why I was embarrassed because my penis is VERY small and looks like it hasn't grown since I was about 3. Still I need to do my schoolwork so you and I will practice what I have to do tomorrow. You first take your top off and show me your breasts and let me feel them, then take your panties off (which you give to me and tell me I can rub them on my penis if it helps). You spread your legs and give me some good looks at your pretty pussy and let me smell and taste it. After a couple minutes of that you open up a bit wider so I can see your other hole and you tell me about it and have me give that one some attention. 

The whole time be reminding me to rub my small penis because I need to cum and be ready to eat the semen. Perhaps towards the end focus on that, and tell me not to be scared you've eaten plenty of it and it won't hurt me. Describe how it might taste and maybe if I eat it it well help my penis grow. Eventually I'll blow my load into my hand (or yours, either way works) and you tell me exactly how to lick it up and savor the taste before I swallow.

Like I said I'd like lots of small penis and cum eating talk from my very loving understanding mommy. I like it when mom uses the proper terms for things -- penis, anus, vagina."

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!

POV Cum Eating

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Sissy Boy Small Penis Cum Eating Instruction

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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