You started out as such a beautiful boy. Dark locks, strong chin, beautiful eyes. I was hoping you would have the manly cock to go along with how handsome you were. As you grew I realized you were cursed with your father’s sad little prick. Looking at it makes me sick. So my dear boy, I have begun unbeknownst to you, hormone treatments. I have scheduled and surgery for your transformation. I have already redecorated and room, I have a few other changes in store for you as well. Since you have not become the man I had hoped you would be. I am going to turn you into my perfect sissy slut. Your journey starts now my sweet girl, let’s get ready!

Castration, Castration Fantasy, Coerced Bi, Female Domination, Female Strap-on, Female Training, Mommy Domme, Mommy Fantasy, Sissy Training, Small Penis Humiliation

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Your haughty upper class Mummy saw you last night, sneaking downstairs. I know you saw me kissing that man dressed as Santa Claus. It wasn’t your father, who is incapable of pleasuring me. It was our neighbour. And I also know that it turned you on. That you jerked off to it. So Mummy has decided that we both have little secrets that we need to keep; Mummy won’t tell anyone that you jerk off over her – over her breasts, if you don’t tell daddy about her secret lover. Okay, darling?

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Your father remarried in his mid-life crisis and now you have a new Mommie who just happens to be the hottest Bratty Bitch from hell you’ve ever laid your innocent virgin little eyes on. You aren’t really so innocent though because you’ve secretly been spying on Her when She gets out of the shower and you’ve been peeping in on Her when She gets dressed as well. You don’t know why you’re being such a naughty boy, but you just can’t seem to help yourself. Your first time masturbating was while watching Her- you thought She wasn’t aware you were sneaking and jerking off to Her, but Mommie knows everything. She finally takes the opportunity to confront you when you are peeping in on Her once again, especially since you’ve become even more brazen in your naughty behaviors than ever before. You will follow all of Mommie’s instructions, including showing Her your tiny little clit dick which won’t grow much more if it all- that’s right, you’ll have a small clit-dick just like your silly old father. The good thing is you’re young and Mommie is interested in sculpting you into the perfect male slave beginning now, in your young age, She will give you a little taste of what being (mind)FUCKED really feels like. Who’s Mommie’s good boy? Yes, you are. Enjoy xo- Princess Pilar

Age Regression, Beta Humiliation, Boot Fetish, Brat Worship, Ebony Female Domination, Little Play, Mesmerize, Role Play, Shiny Fetish, Small Penis Humiliation

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Last night your mommy and I had a long conversation about you. She was very worried that your small dick was running your life. She expressed to me your lack of pussy and how your tiny cock hasn’t really grown that much since you were a baby. She told me you should have been born a girl and that she regrets not raising you as one. Maybe then you wouldn’t feel so bad about not getting any pussy. We decided that I will be taking over as your new mommy and that I will be feminizing you from now on. I think your new life as a girl will be more fulfilling and you will no longer have to deal with the pressures of the male role. Now sit down and listen to mommy as I go over your first new lesson as a girl.

Category: MOMMAS BOY
Related Categories: SMALL PENIS HUMILIATION, SISSY TRAINING, FEMINIZATION, SISSY SLUTS, PUSSY CONTROL

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I just married your dad and moved into your house and now there are going to be some changes. I know right now you think I’m being a mean mommy but in the long run I’m really just helping you. See I know about that tiny little useless dick of yours and if you follow my rules I will help mold you into a useful man instead of a loser with a useless unfuckable beta dick.

Category: SMALL PENIS HUMILIATION
Related Categories: MOMMAS BOY, FOOT FETISH, CHASTITY, JOI, SMALL PENIS ENCOURAGEMENT

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Oops! Mommy caught you jerking off, except she didn’t walk away and leave you to it, in fact she noticed that you were jerking off the wrong way….but don’t worry, mommy shows you how to properly jerk off such a small cock. Now that you have been corrected, mommy will sit and watch you two finger jerk in front of her until you blow your tiny load.

Category: SMALL PENIS HUMILIATION
Related Categories: MOMMAS BOY, CUM COUNTDOWN, JOI

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Come over here and sit down next to mommy I have some advice I need to share with you. Now I know you will be heading off to college soon and I want to make sure you are prepared for what will happen. See the other day when I accidently walked in on you after your shower I couldn’t help but notice your tiny dick. I know being your step mom I haven’t been around your whole life but I was concerned maybe you had a medical condition you hadn’t told me about but when I asked your father about it he said you were perfectly healthy but have always just had a teeny tiny dick. I’m actually surprised given the fact that your father has an extremely large cock, but I guess some things aren’t genetically passed down. Anyways, I’m concerned about your sex life in college with such a tiny dick, I think we both can agree you will be better off forgoing any attempts at sex and just focusing on your studies. Now of course you will have to have some type of sexual outlet and masturbation is probably the best bet for you. So let mommy teach you the correct way to jerk off such a tiny baby dick. I know you have probably been trying to jerk off with one whole hand like a man with a big cock but that’s not the correct way. Here let mommy show you, we will do it together…..

Category: SMALL PENIS HUMILIATION
Related Categories: JOI, ASSISTED MASTURBATION, MOMMAS BOY

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I am so happy that my little man has found a great girl with a huge cock, just like mine. I always taught Sam that his place in the world is as a cocksucking servant to the superior futa females in his life and that is why I know Ella is just the perfect dickgirl for him.
Even the happiest families can experience a little holiday tension though so when Ella suggests that she has bigger cock than me, it almost turns into a full blown futanari family feud! The only way to settle this size matter peacefully is obviously a double blowjob from Sammy. He is going to take his futa facefucking like a good boy and then let Ella and I know which one has the biggest dick. Poor Sammy is going to end up with a very upset Mommy or a pissed off girlfriend but at least he will get to worship two giant futa cocks first!

Category: FUTANARI
Related Categories: SMALL PENIS HUMILIATION, BLOW JOBS, MOMMAS BOY, MILF, FUTA

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Are you wondering about the big bulge in Mommy’s short shorts? Maybe feeling a little jealous of the size of it? I am happy to show you mine, if you show me yours…BUT whoever has the smaller dick has to give the other person a blowjob!
I hope you are not too shy to compare your cute little erection to Mommy’s huge cock. We can even stroke together for a while to give you a chance to make yours get bigger. Mommy enjoys watching you play with your cock almost as much as I’ll enjoy getting mine sucked!

Category: FUTANARI
Related Categories: SMALL PENIS HUMILIATION, SHEMALES, MOMMAS BOY, MILF, FUTA

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Jodi has just come back from a long run in the morning and finds an eagerly horny and hard man back at home. Sweaty and tired, Jodi is in no mood for fooling around, but doesn’t wish to see a hard cock wasted. Enjoy jerking off while watching Jodi stretch out and masturbate in her gym clothes in the front doorway.

Category: JERK OFF INSTRUCTION
Related Categories: MILF, EXERCISE, SOLO MASTURBATION, SMALL PENIS HUMILIATION

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