Dallas thinks that you look like the kind of guy who likes to masturbate. She likes to masturbate, too, so she suggests doing it together. You whip out your cock and she takes off her bra. Can you get it hard for Dallas as you gaze upon her tiny boobs? Yes, stroke it nice and hard – up and down. That is perfect. Keep going. She begins to touch her pussy through her panties, but she quickly decides to remove them. She has such a sexy, petite body! Her sexy tattoos also are a big turn on for you. She reaches between her legs and plays with herself as she continues to help you through your jerk off session. Dallas turns around to show you her ass and pussy from behind and that is your favorite view. As you continue stroking, Dallas tells you that her pussy is becoming wetter and wetter. Today Dallas makes it clear that she wants to see you cum for her and you want to do it just for her. Keep stroking yourself and do it harder and faster because Dallas is ready to see how big of a load you can rub out for her.

Do you have insomnia again? Your Asian step mother knows how important that a good night of sleep is. In her culture, it is not uncommon, she says, for the mother to help a son by helping him to cum. You take her up on this unusual offer and she immediately works your dick for you. Do you see her technique? Let her show you. She puts her mouth on your dick briefly and you fight hard to keep control of yourself. Now grab your cock and start working it just like step mommie Jackie is showing you. She removes her silky robe and you finally see her very sexy body. She touches herself for you. Rubbing her clit, she tells you what a good job of jacking off you are doing. Ridding yourself of a big cum load will definitely make a good night of sleep possible. Well, that is what Jackie tells you. Why would your step mother lie to you? She would not, so you keep stroking yourself. You are ready to cum now, and she wants your sperm on her titties. Now you are ready to go to sleep.

Your parents don’t trust leaving you home alone, so they asked Lily to come over to watch you. You are immediately focused on her hard nipples. You can pretty much get any girl you want, but not tonight. You will not be fucking Lily, but she will let you jerk off to her. Lily encourages you to jerk off as she plays with her body. You love her perky titties and tiny frame. Maybe after she sees what kind of load you can offer her, she’ll come back to fuck you.

Belle complains that no one will hook up with her because she is a nerdy girl. She wears eye glasses, but you can see past that. She is one of the hottest girls that you know. You think about what it might be like if Belle were a dirty girl instead of a nerd. She would not wear glasses and she would definitely wear sexy lingerie. Maybe she would even wear thigh-high stockings and sexy high heels. In your fantasy world, Belle would be hungry for you and she would be more than excited to show off her body to you. She turns around and shows you a few things that she can do with her sexy ass. You would take that ass any way you could get it! Belle talks about all the things you could do to her and how good each thing would feel. With her panties pulled to the side, you watch her play with her pussy. Her pussy lips are hairless, but she does have a nice, dark bush up top. You can hear how wet she is as her fingers explore her twat. Are you almost ready to cum? In your fantasy world, Belle asks you to cum inside her mouth and you give her what she wants. Whoa! You snap out of your fantasy and realize that you have not been paying any attention to the nerdy Belle because you were busy with your sexy fantasy version!

Your buddy's girlfriend stopped over to see him, but he isn't home right now. Dillion says that you make her nervous when you look at her and she quickly tells you that her boyfriend's dick is really not impressive. Since he will be gone for a while, maybe you can spend some time with Dillion. She heard you have a fat dick and she wants to see for herself. As she unbuttons her blouse, she asks you to take your dick out for her. What she sees pleases her and she wants to see what you can do with it. Go ahead and start jerking that dick. After she shows you her titties, she tells you that her boyfriend really does not know much about how to handle a girl, but maybe you do. Do you know how to handle Dillion? She stands up and lets her panties drop. Her sexy pussy is fully exposed right now and you continue stroking your dick. She confesses that her boyfriend's cock does not do much for her, but yours does. Can you cover her titties with a hot load of your sperm? Jerk it harder, harder. Yes! Drop that load onto her titties! Impressed with your efforts, she hopes that this will not be a one time adventure.

It is time for your quarterly review, but you are surprised to be invited to your boss' house. No, you are not being fired, but there is an issue. The issue is that Mercedes, your sexy Latina boss, wants to see your cock. She is not in a good marriage and it is your duty as her employee to make her happy. There is no need for pretense. She just wants to watch you jack off right now. Take it out and get to it if you want to keep your job. You are incredibly turned on and you do as you have been asked. Mercedes is quickly impressed with your dick offering and she is becoming aroused by simply watching you play with yourself. She unbuttons her sweater and she tells you she has fantasized about you before. Soon she shows you that she is not wearing any panties. As you rub your dick, your boss plays with her pussy right in her kitchen! Are you ready to cum for your boss? Yes! You blow your load and you are already looking forward to your next quarterly review.

How far are you willing to go to keep your job? Your manager, Tara Holiday, could fire you right now for your poor performance, but she is willing to give you a favor. If you masturbate for her right here and now, she will consider allowing you to keep your job. She makes it clear that this is not a request. It is an order. When you reveal your penis to Tara, she understands why you are such a poor performer at work. Your cock is less than pleasing to her, but she wants to see what, if anything, you can do with it. You begin to stroke off while she laments your small penis. Maybe she can try to inspire you by revealing her sexy body. Her skirt drops to the floor and you see garters and stockings and a sexy black bustier on this hot boss lady. When she touches her high heels to your cock, your reaction makes it clear that you like what she is doing. Tara seems to delight in the awkwardness of your predicament a little too much, but so do you. When she counts down to 1, she makes it clear that you are to cum as much as you possibly can right there on the floor.

Your step daughter Jenna wants to ask your opinion on her outfit. She has a performance this evening and she has to look good. She has a crush on her coach and she wants to make an impression on him. Do you think that he would like how her butt looks in these shiny blue shorts? Jenna mentions that she is a little tight today, so she begins to stretch to loosen herself up a bit. Her poses are provocative and you find that you are becoming aroused. She knows exactly what she is doing as she invites you to sit on her bed. You are quickly threatened by Jenna. She will rat you out to her mom if you do not do as you are told. She thinks that she is in control, but she probably does not realize you would have jacked off to her even without the threat. Jenna informs you that you cannot cum until she allows it, but you are okay with that. You kind of like the thought of her controlling your orgasm. You also are aroused by her bratty attitude and her sexy, young body. Do you think about sliding your dick into her pussy? That will always be just your sick, twisted fantasy, Jenna informs you. You quickly cum as your bitch step daughter threatens you once again.

Kenzie is your brother's hot sister and she walks into the room and finds you there waiting for her brother to get home with beer. She notes that you have a boner, but she wants to help you to get rid of it. You see her hard nipples teasing you through her top, but she soon lowers her top to show you her tits. You love her fat tits. Kenzie tells you to take your dick out and to start stroking. She is pleased to see your cock offering and she wants to see exactly how big you can grow. Jut watching you handle your dick turns her on quite a lot. She slides her shorts to the side and you see her pink pussy. Her long blonde hair is pulled into two low pony tails. Then she stands up and pulls down her shorts. Her ass is magnificent and she knows it. Kenzie is quite eager to see how much you can nutt for her, so give it to her before her brother gets back home!

You and Lauren had a good time on your date, but she confesses that she is a size queen. She cannot be bothered with a little dick, so before you get busy with Lauren, she needs to see that you are equipped. You show her your dick and she is confused by how tiny it is. The only hope is for you to stroke yourself so that she can see if it gets any larger. Would you even call it a penis? She thinks that it looks more like an enlarged clit and she informs you that you will never have her sexually. Lauren is sorely disappointed and she laughs at your little prick. You are sad and pathetic. You are turned on by the humiliation that Lauren is dishing out to you. She calls your little dick Tiny Tina. She slides her panties to the side and you see her perfect pussy and bush. You will never have this sexy redhead. Wait, how do you cum? Can you cum at all? Lauren wants to know, so keep jerking off your little dick. You never before had an interaction with a woman who so brutally humiliated you and your manhood, but you kind of like the humiliation. She encourages you to cum and she is pleased that you can at least do that much.