Dear Diary, I want to try more things this year, even if my husband is sort of a prude. But where can I find someone who respects my marriage, but will also do all the filthy things that I’m curious about? Maybe…just down the hall! But will my son help me fulfill all my dirty fantasies, starting with sticking his beautiful, hard cock up my ass? I may be a mother, but I’m also a horny little slut! XOXO, Penny Timestamps 2:56 Mom propositions you for anal sex 5:37 Mom in lingerie 8:08 Butt plug and anal masturbation 14:43 Blowjob-handjob-titty fucking combo while butt plug is in 20:53 Remove butt plug 21:28 Your cock in Mommy’s ass 26:06 Mom has an anal orgasm while you cum in her ass 26:30 Cum play, showing off your anal cream pie

ANAL, POV SEX, BUTT PLUG, MOMMY ROLEPLAY, TABOO

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I’m your young, sexy step-mom. You sneak in and find me in my bedroom. Oh, you have a secret to tell me? You broke up with your girlfriend? Are you ok? Well, I’m glad you’re ok. I know you don’t want your dad to know, so I promise not to tell him. Can I tell you a secret now? I’m wearing a butt plug right now. Oh my god…do you have a boner right now? It’s ok! It’s my fault for saying anything! But…can I tell you another secret? I’ve always wanted to know what your dick looks like. Would you mind…showing me? Fuck. I was not expecting such a nice, thick cock. Ok, since you showed me your dick, I’ll show you my tits. Oh, you want to see my butt plug? I’ll show you, but if I do you have to fuck me. Deal? I slide my bikini off and show you my butt plug. I notice your dick twitching and can’t wait to get you inside me. You slowly slide into my tight, wet pussy from behind with a perfect view of my butt plug. Ugh, you feel so amazing inside me. I want you to fuck me hard and deep. I bounce my ass for you as you thrust in and out of me.

ASS FETISH, BUTT PLUG, MOMMY ROLEPLAY, POV SEX, TABOO

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You’ve been such a good girl! Let Mommy reward you! 7 minutes in heaven, watch me strip for you, and put in my plug. You’ll get to watch me play with my pussy, cooing about what a good baby you are. Talking dirty to my sweet girl while I bring myself to have an intense orgasm.

MOMMY ROLEPLAY, STRIPTEASE, BUTT PLUG, SOLO MASTURBATION, ROLE PLAY

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Your beautiful Italian stepmother today wants to play a really exciting game: she slams her big ass in your face and gives you careful jerking instructions. Follow what he tells you and indulge in a fantastic taboo orgasm. His words are like fire because since you were little you always thought of putting your hands on your stepmother’s big ass and breasts. So seeing her like this causes you a never-before-felt excitement that will be hard to hide. Think if people who know her and who know you knew what would they say? Adora il grosso culo della tua matrigna italiana – La tua bella matrigna italiana oggi vuole fare un gioco davvero eccitante: ti sbatte il suo grosso culo in faccia e ti da attente istruzioni per masturbarti. Segui cosa ti dice e lasciati andare ad un fantastico orgasmo taboo. Le sue parole sono come fuoco perchè tu da quando sei piccolo hai sempre pensato di mettere le mani sopra il grosso culo ed i seni della tua matrigna. Quindi vederla così ti causa un eccitamento mai provato prima che sarà dura a nascondere. Pensa se lo sapessero le persone che la conosco e che ti conosco cosa direbbero?

TABOO, BIG ASS, MOMMY ROLEPLAY, SINGLE MOM, BUTT PLUG

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So you know that your dad and I have been trying to get pregnant for a while. But can I tell you something? I really, really miss fucking you. It’s too much of a risk for you to fuck my pussy while I’m off birth control. However, I do have a butt plug in right now and thought maybe you might want to fuck my ass? I tease you for a bit while I strip out of my clothes. My pussy is so wet thinking about you fucking me…and also because I’m ovulating right now. What if…you fuck my pussy first? I want to feel you. You slide into my wet, fertile pussy and fuck me. My butt plug makes me even tighter than usual. You can’t cum yet though. I can’t wait for your dad to finally get me pregnant so we can fuck more often. Are you ready to fuck my ass? I pull my butt plug out and help you slowly slide inside of me. You feel amazing inside my ass. I don’t even let your dad fuck me like this. I ask you to fuck me from behind while I use my hitachi on my clit. Fuck me hard and deep. I get closer and closer to orgasming. I want you to fill my ass with all your cum. Cum in mommy’s ass.

ANAL, ASS FETISH, BUTT PLUG, MOMMY ROLEPLAY, TABOO

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We asked you to show up a little early because I need to get you ready to entertain everyone. You did not think my son and all his jock friends wanted you to actually party with them? No, sweetie, you are just here as a little femboy party favor. I am going to get you all pretty and sissified so those boys have a blowjob doll for the night.
I will do your make-up while you pick out some cute lingerie to wear. Then we need to get that cute little ass filled by this pretty pink plug. Go ahead and give it a little lick so I can slide it in easier for you. The butt plug might be a tight fit but some of the boys coming over are much bigger so you will be glad to have your hole warmed up beforehand, trust me.

TABOO, FORCED FEM, MAKE ME BI, FEMINIZATION, BUTT PLUG, MILF

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Mom’s noticed you catching her naked a handful of times, and feels it’s time to have the talk, or at least a talk. She sits you down, confronts you, and explains how she is going to show you her body and how everything “works,” She closes the door and undresses reassuring you not to be nervous. She starts with her breasts explain the nipple & areola and talks about breastmilk & how the milk comes out, showing you and spraying & self-sucking her own milk from her breasts. She encourages you to try some, you hesitate at first but then decide to try some. Mom then decides to show you her pussy and explains & shows the different parts of her vagina and asking if you’d like to see how it looks when a woman cums. Encouraging you to get a nice up-close view she talks about getting wet, how playing with your ass is also arousing for some. Deciding to show you what a butt plug looks like, while masturbating by fingering herself & then using a vibrator. After mom cums for you, she shows off playing with her own cum and how it can be different for each woman.

MOMMAS BOY, ROLE PLAY, BUTT PLUG, MILF, LACTATING, FINGER FUCKING

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Ohmygoodness Mommy Anastasia St. Claire has walked in on me farting and laughing about it like a baby. I try to explain that its just a tummy ache but Mommy caught me way too much in the act with me lifting my bottom up in the air and giggling about it to myself. Its so embarrassing, I can’t believe she just happened to walk in at this time of all times. Mommy scolds and shames me, telling me that “Princesses don’t toot” and especially not laugh at it. And as if that wasn’t bad enough, Mommy then tells me that if I’m going to act like a baby about it rather than a princess, she’s going to treat me like a baby! She grabs the diaper off my nightstand, making me lay out on it an spread for her before she warns me that she will be silencing my noisy bottom and pulls out a large pink butt plug! Its so big that even with lube, it take a minute to get it into my tight untrained butthole. After making it fit, Mommy finished with a powdering, rubbing it all into my little pussy before taping my diaper up! My plug is so big that when she has me bend over to check that my diaper is all securely and tightly on, I can feel it slide deeper and wider but Mommy doesn’t care for my complaining….I’ve certainly learned my lesson about being a rude little girl now.

ADULT BABIES, AGE REGRESSION, BUTT PLUG, DIAPER DISCIPLINE, MOMMY ROLEPLAY

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This is a follow up to “Step-Mom Shows you her New Bikinis.” Your step-mom is making you breakfast while she explains that even though your dad is out of town, she has a lot to get done, and she wants you to focus on your own tasks. As she rambles on about what she needs to do, you can’t help but stare at her ass showing through her see-through leggings. She chides you for not listening and responding to her. After she gives you toast and scrambled eggs, she starts loading the dishwasher. You can’t even eat as you watch her bend over. She catches you staring and says that she doesn’t understand why you’re so obsessed with her butt (she knows why). Eventually she gets frustrated and gives you a full view of her booty, she even pulls down her leggings, and tells you to get an eye-full so you can focus for the rest of the day. She mentions that she made a mistake showing off her ass to you previously, and just because she let you fuck, doesn’t mean it can happen again. After, she walks into another room and you pull out your hard dick to start stroking to the memory of that ass. She walks back in and catches you. She decides that something needs to be done, and she tells you to meet her in her bedroom after you finish eating.
When you go into her room, she’s now wearing lingerie and a lace robe. She tells you that you’re not in trouble. She explains that since you are obsessed, she’ll fulfill your little fantasy one more time. She tells you to pull your dick out again, and she shows off her body. She mentions that she has a surprise, and when she bends over, you find out that she has a buttplug in. She says that she’s getting her ass ready so you can fuck it again and get everrrrryyyything out. You’re rock hard by now, so she gets on her knees and sucks your dick. Once your dick is lubed with her spit, she gets up, bends over the bed, removes the buttplug and tells you to slide your cock in. She gets into it and starts begging you to fuck her ass hard and drain your balls. You oblige and fill her asshole up with cum.

TABOO, ASS WORSHIP, BUTT PLUG, VIRTUAL SEX, ANAL, MASTURBATION ENCOURAGEMENT

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I was so surprised to get a phone call from your teacher that was not a glowing compliment. What has gotten you off track this semester? Sweetheart, being horny is normal and not an excuse for poor academic performance. What do you mean are horny for something “weird”? You can tell me and I promise I will do whatever I can to help you get your grades back up.
Wait, you want me to wear what? Stick that thing where? Oh goodness. Well, if dressing up in this slutty anime costume and wiggling my ass in your face with this plug in my hole is the only way to get you back to straight A’s, then I guess that is what I have to do.

TABOO, MOMMAS BOY, COSPLAY, BUTT PLUG, POV SEX, MILF

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