You've had too many nights of little to no sleep. It's about time we remedy this problem. When I have trouble falling asleep I masturbate. Don't be uncomfortable with that thought. I'm just your stepmom but I care for your well being especially now that you're in college and need your rest for school. I happen to notice you have an erection under your sheet which tells me that masturbating is not too far fetched an idea to help with your insomnia. Why don't you let me help you at least this once. I've been told I give a good hand job. It's been so long since my hand was wrapped around a hard young cock. Your father certainly doesn't get this hard anymore. I don't even have to see your dick, I'll leave the sheet over it so you don't have to be embarrassed about me seeing it. I happen to think I'm a pretty nice mom right now in here late at night jacking off her step son so he can sleep. Oh my, you dick is really getting super hard. You must be close to ejaculating. Go ahead and let it all out. Well from the look of how much cum you soaked the sheet with you clearly haven't been jacking off enough. You look very relaxed now so I'm going to leave so you can fall asleep. I'll clean your cum soaked sheet tomorrow. Oh, and don't tell your dad about the insomnia remedy I gave you. This is our secret.

I figure it's time you knew that I've been fucking your best friend. You know your dad is kind of getting up there in years and even though I love him, he doesn't satisfy my needs. Your best friend offered his cock to me and I took it, again and again. Oh now don't get jealous. I can't fuck you, you're my step son. Maybe I can at least help you get off without touching your dick. Go ahead and get your dick out for me. I want to see if it's as big as your friend's. You can rub it for me. That's it, rub the tip gently. Show me how you stroke it. I'll even show you my mature body while you rub yourself to climax. This is a bonding moment isn't it? I hope your dad doesn't come home from work early and catch us like this. It's not bad because I'm not touching you. Are you ready to cum for me? That wasn't a very big cum load, you poor thing. I may have to save some of your friend's cum in my pussy next time I fuck him so I can show you what a real cum load looks like.

This lesson is all in love. I honestly want you to get a girlfriend and get a life outside of this house. You're man enough now to not be stuck at home all the time. I have a little motherly insight that might help your cause in the female finding department. You need to do some trimming on the nether regions to impress a girl. I'm going to instruct you how to groom down there and then I want to see the size of your load. I have to give honest feedback in order to fully help you get a girl.

I know you hear your father and I fighting quite a lot lately. It's because of your real mother always butting into our business. I hate to see you in the middle of all this contention. It must create much undo stress in you because it sure does do it to me. When you dad and I fight so much it means we don't have sex. Look at me, I am a woman who needs sex. You're a nice looking young man. Are you into MILFS? I bet at least one of your college friends has fucked a MILF. What do you say, shall we make this interesting between us? You can keep a secret right? I thought so…

Your sister told me you are skipping class because you are getting bullied at school by the guys in your physical ed program. I know college can be hard to deal with sometimes but you have to go back to school. Your sister also told me the bullying is because you have a small penis. I am only your step mother but I am trying to do all the duties a real mother would and feel I should talk with you about this matter objectively. Lets determine if you even have a small penis. Go ahead and pull your pants down and show me. Well, maybe you should get it hard so I can really see it's growth potential. Hmm, o.k. well let's talk about the advantages of having a small penis. You can satisfy very petite women. You can have anal sex with most any woman and it won't hurt her. You won't ever have any embarrassing bulges in your pants to contend with in public. Now that you're hard I probably shouldn't leave you like that. The least I can do to help you feel better is help you get a good nut before you have to go back to school. I will help you have a really good cum. Go ahead and stoke yourself for me. Don't be shy, I want to do this for you. I'll get undressed and tell you exactly what I want you to do for me. Now that mommie has undressed for you and showed you her beautiful naked body, will you stroke yourself and cum for me? Imagine you are fucking my tight little asshole with your perfect penis. Oh yes, that's it give me all your hot cum right on my pink puckerhole. There now, don't you feel better already? You made me so proud and I'm sure you're going to satisfy any woman you want with your penis just like you satisfied your mommie.

Your dad has an uncomfortable time talking about sex with you so he sent me in here to give you some words of advice. First, I have to ask if you are still a virgin? This is great news that you are! More young people your age should remain virgins because having sex can sometimes complicate relationships. What I am trying to say is you should masturbate to your hearts content rather than go spread that seed among girls that are practically strangers. I almost don't want to admit how often I masturbated before meeting your father. In fact, it doesn't have to be complicated at all to get yourself off. Now that I am having all this talk about pleasuring ones self, you don't mind if I use your pillow for a few minutes do you? For old times sake.

Since when is an open door an invitation to watch your stepmother masturbate? I was sneaking a few minutes to myself and now I have to reprimand you for watching me pleasure my pussy with my vibrator. I thought you were at work or in class at this time of day! This is so awkward to have this discussion with you. I suppose in the end it's just the matter that we all need to have sexual release, even you. I would like to finish if you would like to join me. So long as you don't breathe a word of this to anyone, let's hurry up and both get our nut so we can carry on with our day.

Pretty strange how when you grow up in a small community things have a way of coming full circle fast. I had the biggest crush on you in high school and you wouldnt give me the time of day. You completely embarrassed me in front of all my friends with your better than me attitude. Your dad fell head over heels in love with me and now I'm your stepmom. How dare you think that when he leaves to go out of town for work you think you can come get my pussy now. Oh no, only thing you are getting from me is a lot of verbal attention. Ill let you see what you wont ever get to touch.

My step-mom would be what old school dudes call a 'Brick House'. She is stacked in all the right places. My dad would kick me out of the house if he knew the dirty thoughts I've had about her. Imagine my surprise when she came to my room late one night saying she had a craving for hard cock. Apparently my dad is nothing more than a limp noodle dick for her, even after taking one of those blue pills! I was actually lying in my bed considering rubbing one out before nodding off to sleep and here she was saying she just needed to feel a hard cock in her hand and could she touch mine? I wasn't going to deny her hand on my hard on. I was so nervous that as much as I tried to relax and realize one of my fantasies was coming true having her in my room, my dick had other plans. Her breasts nearly spilled from her dress and it still wasn't enough visual to get my wood solid. She stroked me as she talked in her sexy soothing voice, asking if I like the way mommie stroked my cock. I couldn't even reply I was so worked up inside. I just lay there and let her have her way with my dick. She took her dress down and let me see her mounds of flesh released from her lacy bra. Holy hell I wanted to bury my face in between those huge tits! I wasn't sure what I would be able to do so I lay still as she continued with her stroking skills.

Can you help your step mom decide which shoes to wear out tonight? She models 2 pair for you. You start getting hard just watching her try on the shoes especially the really high heels. Step mom Mellanie sees your hard on and she suggests that you get rid of that hard on quickly. Get your dick out and jerk it off to your MILF step mom. What really did it for you is her ass. Her skirt is tighter than a skirt should be, but it perfectly shows off her big booty. Is it getting warm in here? Step mom Mellanie starts taking off her blouse and then her skirt so that she can cool down a bit. That only makes you get hotter! She is wearing black panty hose and they have a slight sheen to them that you really like. Her legs rubbing together gives off that very distinctive sound of nylons rubbing against one another. Your nasty step mommy then starts jacking your off with her nylon-encased feet. It feels so good! It isnt much longer till step mom Mellanie is begging for your sperm and you give her a bunch on her sexy nylons.