Virtual Anal

darlingjosefin – Five Cumshots With Little Sister

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darlingjosefin - Five Cumshots With Little Sister

darlingjosefin – Five Cumshots With Little Sister

Your grades have been slipping, and your little sister wants to help you out. I know you have a Sex Ed test tomorrow, Jake – you need to study! I offer to help you out by quizzing you. As we start, you seem distracted. You tell me that it’s hard for you to study Sex Ed because it makes you horny … also you can’t stop staring at my boobs. MY boobs! Your little sister’s boobs are distracting you! It’s pretty weird, but since I really want to help you out (what are little sister’s for, after all), I offer you a deal – every time you get a question right, I’ll take off an article of clothing. You readily agree and suddenly you’re an expert on Sex Ed! You answer all the questions right until I’m sitting in front of you naked. I notice that you’ve gotten hard … that’s so weird! But since you did so good studying, I offer to give you a little bit of relief. First, I suck your cock. You liked my tits, though, right? I switch to giving you a tit job, and you don’t last long before you cum! Can you get hard again, Jake? I know you’re my big brother, but I’m really horny now. You fuck me in missionary and cum in my pussy. I didn’t cum yet, though! I tell you to stand still and let me show you what I can do. I ride back on your cock in doggy until I cum. You cum at the same time, and your big load of cum drips out of your little sister’s pussy. I bet you can still get hard, right, Jake? I give you another deal. If you promise to do REALLY good on your quiz tomorrow, I’ll let you fuck my ass. You agree. I lay on my side and you ease your cock into your little sister’s ass. You fuck me hard until I cum, and then cum all over my asshole. I bet you can cum one last time! I stroke your cock until you drip your jizz all over my face. But you keep stroking! I can’t believe how much cum you have! You bust a HUGE final load all over my face while I moan. The scene ends with your little sister sitting on her bed, covered in all five of your cum loads. You know, if this helps keep your grades up … I don’t mind doing this again, big brother. Note: All sex scenes have a visible cock except the anal scene, which is simulated/implied.

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Olive Wood – Mommy Knows What You Did

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Olive Wood - Mommy Knows What You Did

Olive Wood – Mommy Knows What You Did

You’ve really done it this time, Son.
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Olive plays your mother. She talks to you in private about what you did and confronts you with pictures you have taken of her while she was sleeping. Now she will punish you with her strapon and pegging.

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Olive Wood – Stretched by Mommy and Her Huge Cock

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Olive Wood - Stretched by Mommy and Her Huge Cock

Olive Wood – Stretched by Mommy and Her Huge Cock

ou just can’t get enough of Mommy’s giant cock.
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Unofficial desc: Olive is your mommy who happends to be a futa. She trains you to like cock. She makes you virtually suck her cock and the she takes your ass.

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Olive Wood – Wife Pegs and Feminizes You

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Olive Wood - Wife Pegs and Feminizes You

Olive Wood – Wife Pegs and Feminizes You

Your wife finds the key to saving your marriage. I hope you like wearing lace panties.
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Olive Wood plays your wife who tells you that to save your marriage she is going to domme you and turn you into her sissy bitch. She feminizes you and pegs you.

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Olive Wood – Neighbor Puts Stuff in Your Butt

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Olive Wood - Neighbor Puts Stuff in Your Butt

Olive Wood – Neighbor Puts Stuff in Your Butt

Last time you ran into your neighbor, you confessed to listening to her make porn through the walls. Your encounter lead to her ordering you to strip down and show her how you like to stroke yourself to the sounds of her moaning next door. You’ve been desperate to find an excuse to head back to her unit, but haven’t found one until today. When you accidentally receive and open one of her packages containing a sizable butt plug, you decide to hand deliver it to her door. Suspicious that most of the packaging seems to be missing and doubtful that you didn’t know what you were doing when you opened her mail, she decides the best way to set things right might be to try the toy on you. You don’t object as she stretches you open and tugs on your new kitty tail, nor do you stop her when she insists upon pegging you with an even larger toy and counting you down to orgasm.

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Olive Wood – Trained and Feminized by Mommy

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Olive Wood - Trained and Feminized by Mommy

Olive Wood – Trained and Feminized by Mommy

Mommy knows your secret! You’re horrified when she confronts you about your obsession with massive cocks and the oversized dildo she found under your bed, but Mommy is understanding. She knows that the only way to help you is to fully feminize you, lock you in chastity, and train you to please masculine, superior men like the good little slut you are.
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This video was a custom creation and I use the names “Thomas” and “Theodore” a few times throughout.

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Olive Wood – Mommy, There’s Something in My Ass

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Olive Wood - Mommy, There's Something in My Ass

Olive Wood – Mommy, There’s Something in My Ass

Curiosity got the better of you and you now have a Tamagotchi lodged inside your anus. Despite your best efforts, you can’t seem to squeeze it out, and have no choice but to run to your mother for help. Mommy dons a pair of latex gloves and slides one lubricated finger inside you, but she can’t quite seem to reach the foreign object. She’s going to have to use another finger, and another, and another. It isn’t until Mommy slips her entire hand inside you that she’s able to reach the toy you foolishly lost inside yourself.
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The deed is finished with much difficulty, but you don’t want her to stop. You’re an aching, slippery mess, but you beg her to use her fingers once more to help you cum. Though she’s reluctant at first, you manage to convince her that helping you is the most humane course of action. Her hesitation swiftly turns to delight as soon as she’s back inside you, and she gleefully stretches you to your limit, driving you to experience an orgasm like no other.

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Olive Wood – Mommy, Theres Something in My Ass 2

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Olive Wood - Mommy, Theres Something in My Ass 2

Olive Wood – Mommy, Theres Something in My Ass 2

Goddamn it, Son. You’ve gotten ANOTHER small object stuck inside yourself and Mommy has to come to the rescue yet again to help remove it. Mommy is starting to suspect you’re purposefully hiding things in your asshole because you secretly love the way her gloved fingers feel sliding inside you and stretching you open.
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Is that so?

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Olive Wood – Mommy And Son Play with Their Cocks

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Olive Wood - Mommy And Son Play with Their Cocks

Olive Wood – Mommy And Son Play with Their Cocks

You’re finally a big enough boy to masturbate with Mommy. You love watching her stroke her big, thick cock for you and obediently taste her and touch her as you play with yourself. As things heat up, Mommy asks you if you think you could handle sitting on it. You’re confident enough to try, and Mommy gently talks you through climbing on top of her and taking her all the way inside you. As a reward, Mommy strokes your cock as you ride her and brings you to climax as she fills you up with her load.

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