Video Description: Your supposed to be getting ready to go to a party with your stepmom, but she doesn’t quite approve of your outfit and asked you to change, to which you hint you’d like to mess around, AGAIN??! Fine but you better cum quickly because stepmom is really looking forward to this party, she agrees to a blow job, but can’t resist the urges to undress and finger herself while sucking and stroking your cock until you fill her mouth full of cum.

Video Description: When you come home from class you find your stepmother in her usual spot reading one of her books, she looks beautiful and you stand and stare at her, your attraction and desire towards her one of your biggest kept secrets. You've tried to distract yourself with girls at school and one in particular you've grown quite fond of and would like to invite her over since you two are working on a project together. When you tell your stepmother the news, she's delighted and teases you a bit, and encourages you to invite her over today. Then she does her usual nagging and making you help her clean up as she normally does when any guest comes over for a visit. She even makes dinner, you love watching her clean... another deep dark secret, your mothers voluptuous curves are difficult to miss, she had natural breasts and she can't hide them away in any outfit, and her perfect round ass is always peeking through her shorts, or like today you catch sneak peeks as she bends down to clean in front of you. You do your best to hide your boners and secret desires towards her... trying to shift your focus on your classmate instead. When she arrives at your place you can't hide it any longer, she is after all very similar to your stepmother in so many ways... Her natural red long hair, her green eyes, big tits, though you wonder if she's only wearing a push up bra... and she to has an hour glass figure. The difference is you dont have to hide you attraction for you, you can reach out and kiss her, touch her... she's not just a fantasy in your mind and best of all she wants you, badly. She seems almost disappointed your stepmother is home and you two can't be alone. She's teasing you, trying to kiss you, trying to touch you... but your stepmother keeps "checking in" and ruining the moments. You forget to hide your boner, and your mother giggles and suggests you go to the restroom. But you get lost in a fantasy while reliving yourself, forgetting time and boundaries and social norms, your try your best to focus your sexual desires towards your classmate, this beautiful, popular girl in school that definitely wants you, but you can't help it... you keep shifting fantasizing about your stepmother. Slightly embarrassed by taking so long in the bathroom you invite your classmate to your bedroom, and she takes no time undressing in front of you, teasing you, she wants you... You try your best to stay present and enjoy the experience of her sucking, licking, stroking you but flashes and fantasies consume your mind and you get lost in your desires for your stepmother... fucking your crush but wishing and fantasizing about your stepmother. Almost getting caught when you accidentally refer to your classmate as stepmom... luckily you play it off and your nosy, nagging, beautiful stepmother rescues you but knocking on the door asking if you guys need anything?

Video Description: In episode six of diary of a sex worker Kelly is saying bye to “john” (the main character who initiated the documentary) He asks a few more questions and Kelly makes a few further confessions, speaking about her clients she’ll be pleasing and entertaining this same evening after he leaves. She mentions JOI and finds it cute he doesn’t know that it stands for Jerk Off Instructions, she decides to give him a little preview of what exactly a JOI session can look like. She starts teasing, touching herself, playing with her pretty pussy, dirty talking and telling him (YOU POV Viewer) exactly how to stroke for her until you both reach climax as she tells you she’s getting close and gives you a count down and you cum together. Shortly after her phone rings and she takes the call, from overhearing the call it seems to be another sex worker friend, maybe coworker? When she gets off the phone, she says it looks like it’s going to be an even longer night, she’s taking on one of her “friends” regulars and speaks briefly about helping each other out occasionally and how that works. Something about a virgin, she’s unsure if he wants to roleplay or is genuinely a virgin, regardless…your time it up and she sees you out. The next scene is Kellys panty fetish/twerking client (POV for viewer throughout) Kelly teases, twerking in various positions, taking her time to really tease you and entice you with her perfect round ass, bouncing it up and down for you, slowly stripping from her clothes down to her panties and then bending over for you her big fat ass bouncing. She bends forward, removes her panties and stuffs them inside her pussy and brings herself to orgasm and slowly pulls them from her pussy, shoves them into her mouth and bends over the bed ready for you to fuck her deep and hard. Pausing to switch outfits and a new pair of panties she repeats the twerking, teasing, striping from her sexy red dress, stuffing the panties inside her and then pulling your cock inside her with her stuffed panties fucking them deep into her. She again bends over and pulls them from her pussy slowly, shoves them into her mouth and you fuck her again doggystyle until you cover her ass in cum and she invites you to her shower to clean you off.

Video Description: You’ve been having an affair with the well-known neighborhood whore. Cheating on your wife with this known homewrecking neighbor. She tends to start affairs mesmerize husbands and then dumps them when they finally decide to leave their wives, or so rumor has it. Each time your wife steps out Kelly knocks at your door, each time getting riskier and more frequent, but the sex is unbelievably good and there’s something about this hot sexy red headed MILF you cant seem to resist and consistently risk your marriage and getting caught with. Today is no different, your wife left to run a few errands and Kelly is at your door wearing a nice coat hiding a very sexy and revealing outfit underneath, you never tell her no, how could you. The way she walks, talks, undresses, desires you, you’ve never cum so much or had such a fulfilled sex life before. She teases you, taunts you, strips for you, leaving her clothes all throughout your house, begging to be caught, enticing you to leave your wife so you can fuck all the time. filling her pussy full of cum and then frantically trying to get her to leave as quickly as possible trying to resist the urge to fuck her again, hoping your wife doesn’t come home sooner than expected. Wondering what the neighbors might think, or say… or know…?

Video Description: In episode seven of Diary of a Sex Worker Kelly is meeting with her NEW Client that her friend sent her way. She forgets to turn off the camera and when she greets him, he is shy, awkward, nervous, and slightly confused asking where her friend is. Kelly apologies and offers to cancel the appointment his worker should have told him what to expect. He notices the camera and Kelly is apologetic and kind, and he decides to keep the apt with Kelly as she is breath taking and there’s something that feels comfortable about her. They sit a chat for a moment, Kelly is trying to get a feel of her new client’s needs, seems the both of you not only have A lot in common, but it also seems you have a lot of strange similarities between you to. Kelly brushes it off thinking she must just be on edge from all the confessions she’s been making earlier that day. When she asks if he’s a virgin he asks to turn of the camera and she does. (The remainder of the video is POV of the new client) You share with Kelly that you are a virgin and that you’ve been a regular learning various ways to please himself and women. She’s intrigued and asks if you’d like a massage, you offer to massage her instead, she sits back with her feet on your lap, teasing you a bit spreading her legs revealing she isn’t wearing any panties. She plays gently with herself, teasing you, enticing you, then leaning closely to kiss, and make out with you. She asks if you’d like to learn how to make a women cum, she fingers herself, teasing you, and walking you step by step how to touch, tease, linger, and finger her till an explosive squirting orgasm, you ask to taste her and try out some of the techniques she just taught you and she sits back and you make her orgasm even harder… your both aroused and she asks to taste you, to please you and you agree. She strokes you, tastes you sucks you, and then notices you seem anxious, she pauses and asks if you’d like to slow things down or stop. You confess you heard she may have breastmilk, Kelly catches on rather quickly and escalates wondering if a stepmotherly roleplay would also appease you and it does. She covers your cock in milk, sucking, spraying, licking, tasting, telling you what a good boy you are. Escalating the stepmom dirty talk as she can tell it is exciting you, she tells you she wants you and she starts riding your cock, bending over in doggy style, missionary, kissing, making out, fuck stepmother, (beautiful agony) onto the bed until you can’t help but explode inside of her. She’s surprised, normally she doesn’t get so lost in an orgasm she forgets to have you cum anywhere but inside her. But she tries her best to not make a big deal of this, she can tell your lost in your arousal and still lusting for her and time is running out… she invites you to shower. She checks in with a client and you notice a small heart tattoo that seems so familiar… and when you ask, she says “Love is a Roller Coaster” and you nearly faint. Kelly instantly comforts you and brings you water, she thinks your lust sick, and hooked on her and just not thinking clearly, she tries her best to let you down easily to not ruin the mood, but when you are persistent… eventually it sets in… OMG. You’re my stepSON!?