Jerk Off Instructions 55 - Step Mom Fun (2015)

A stepmom is still a mother figure; and just like any good mother, sometimes she needs to help her stepson learn how to do things properly. Even if it's teaching him how to jerk off!

Jerking for my stepmother Ariella the widow . Widowed Ariella is looking to you (her stepson) to be the man of the house now and she expects that you will service all of her needs. One of her needs is cock. If you are unable to fulfill this need, you will have to move out. Even without that threat, you were already willing to help her in any way possible. After all, she is pretty hot and her big tits have been your masturbation fodder for quite a while now. Get out that dick and start stroking it. She suggests that you use both hands on your hard shaft. While you manhandle that dick of yours, your poor, widowed stepmother begins to reveal her big titties to you. Very soon thereafter she asks for your cum all over those big tits and you obediently deliver.

Masturbation session with step mommy Caroline. You have been caught by your step mother in your sister's bedroom. You are holding your sister's dirty panties. You fear the very worst, but your step mommie surprises you with her reaction. Do you think that you might be able to control your nasty urges? Perhaps step mommie can help. Why don't you just masturbate instead? It is a very therapeutic activity, so grab a hold of your dick and start working it right now. Step mommie Caroline will walk you through your first session. Your technique is flawless from years of practice, but it is exciting to do this in front of a real woman. When she removes her bra, you are shocked to see that her nipples are pierced! You also now notice a tattoo on her thigh. Now you wonder what other surprises she might soon share with you. Step mommie Caroline asks you to step up the pace of your strokes and she then lowers her skirt. She is wearing black lace panties and she sees that you are getting ready to cum. She removes her panties and sniffs them before offering you a sniff. You see she also is pierced on her pussy and you feel that you will soon cum nice and hard. Step mommie Caroline is extremely excited with your fat load and she suggests that this incident will not be shared with anyone else.

Stroking it for stepmother (with Jennifer Best). Your step mother is getting ready for her first date since your father passed last year. Can you help her choose what to wear? Much to your surprise, she changes her top right in front of you and you see her full titties! You feel your dick getting hard. This is wrong, but you cannot help yourself. Her titties look so good in the second top. You see her nipples are erect. Now she tells you how lonely she is without your dad around, but that she is so glad that she has you in her life. She asks you if you like her boobs and she undoes her top to fully reveal them to you. They are fantastic and again you can feel your dick getting hard. This time, though, your mother notices. She seems to approve. She stands in front of you telling you that she has needs and she caresses her titties. Come closer to your mother. You are now very close to her and you can feel the heat coming off of her body. Sit on the bed. When she reaches over to you, you are a little surprised that she reaches for your cock. You take your cock out and start stroking it. She tells you to touch her tits and you do as you have been told. It is clear that she is becoming turned on watching you pleasure yourself. She spreads her legs and you see that she is not wearing any panties for her date! Mommie is a slut!! As she works over her pussy, you think that you would like to keep her to yourself. When she tells you to cum on her titties, you do just that. What mess you have made on your mother!!

Step mom's nude panty hose (with Maya Hills). You are caught looking up your step mother's skirt at her panty hose. She knows you have a fetish for them and she confronts you. What would your father say about this? You are unconcerned with his wishes. Your sexy step mother Maya does not really mind. In fact, she now knows where all her missing panty hose have ended up!! Take your dick out and stroke it while you look at her pussy through those nude panty hose. She invites you closer so that you can smell her. There is a special quality to the scent of a woman's pussy after wearing panty hose all day long. Even her pretty feet have a distinct panty hose odor that turns you on. As she rubs her legs together, the distinct sound has you mesmerized. Would you like to see more of step mommy? She removes her blouse and bra and you see her big titties, but your focus is her pussy inside those panty hose. With each stroke you feel your balls tightening...you know your orgasm is building. Step mom Maya's ass is high in the air as she plays with her pussy. You cum on her ass and pussy and leave a hot, sticky mess on her panty hose.

My step mother Holly West helps get me off . Holly is uncomfortable with how you seem to hover over her and creep on her. She is your step mother and she wants this to stop. You like what you see in Holly, but she thinks that you two have to take care of things. What she suggests is that she helps you get off. Maybe that will calm you down a bit. She will not touch you, so forget it. Just get your cock out and stroke it. Holly notes how very hard your dick is. She seems to like what she sees as she takes off her tank top. Her boobs are perfect and you even like seeing her tan lines. She directs you to stroke fast and hard, but when you ask if you can titty fuck her, Holly draws the line. You will have to imagine that you are sliding your cock between those titties. You are surprised to see how tight your step mother's body is. This older woman is looking to see how big of a load you can give her, so you work up a hot batch just for her. Step mom Holly likes what she sees. You feel confident that things will progress with her with enough time.

Bonding time with step mom Samantha Ryan. Your dad and step mother were fighting last night and she wants to talk to you about what you heard. Samantha and your father are going to separate. For now, it will be just the two of you in the house as your dad looks for an apartment. Your dad was cheating on Samantha and you do not understand how he could cheat on such a sexy woman. You actually feel badly for your step mother. Samantha hopes that you can now be the man of the house. Can you fill that role? You sit on the bed with her and your role as man of the house begins. She is eager to see if you really are a younger version of your father and she soon finds out that you are. Your dick is impressive and she asks you to start jerking off. Samantha is getting turned on by you and she is ready to show you things that your college-age girls don't know about. As your hand moves on your hard shaft, you realize how lucky you are that your step mom is so turned on by you. Samantha is not too many years older than you are maybe 10 years, if that. Her small tits would look even better if your jizz were dripping down them. Before you know it, she is wearing only panties and shoes, but those panties don't stay in place for long. Your step mom has urges and only you can fulfill them for her. Do not disappoint step mom. Cover her with your jizz bomb and do it right now!