Vile Habit

Be sure to see Step-Mommy Issues 1 for the first part of the series!

You come for an appointment with me, your chosen for how open-minded I am and...how much I remind you of your beloved step-mother. Your dreams and fantasies about your step-mom have been bothering you, and I'm the first person you felt you could talk to about them. I have some unconventional treatment methods, like trance work and roleplay therapy that help you to act out these feelings instead of repressing them, which unfortunately gives you feelings of guilt and shame. You confess that not only do you dream of being sexual with your step-mother, you're fixated on her pantyhose and her cleavage as well. I talk you through an induction, past your distraction on my deep cleavage and nylon-clad legs. I remove my glasses so you can stare into my eyes as I bring you deeper and deeper into a safe place. I plant triggers to make you associate me with your step-mother more and more, until you believe you are at a family party, in a bedroom snuck away for an erotic interlude with your seductive step-mom. You're completely relaxed, guilt-free, and under my spell as I tease you with my pantyhose, and as you can see, I'm not wearing any panties. I tell you how much I love your eyes on me, and how I want to see your cock. I encourage you to jerk off for me, and I rub the gusset of my pantyhose, then reach my hand underneath to finger my wet pussy. I tell you how much I want you, the forbidden fruit, but that we have to be quick and careful, and not remove our clothing, so we don't get caught. You're soon ready to cum, and I let you titty-fuck my cleavage, telling you I want your cum on my tits, then I'll hide it and wear it to dinner, but you shoot such a big load it goes in my hair, dripping down over my chest and bra. I used a squirting dildo POV style for this.

After a long day at work, step-mommy's feet are tired. She works as a secretary and she always dresses a bit sexy, wearing tight skirts, stockings or pantyhose and high heels, because she is hoping for a promotion. You offer your hard-working single step-mom a footrub, and she kicks off her patent leather pumps, releasing the delicious aroma of her sweaty feet into the air. But first she gives you a nice kiss on the lips to thank you, and did she slip you a little tongue on purpose or by accident? You start rubbing her arches and soles in her shiny nude nylons and she moans with pleasure. You know how to make your step-mother feel good. Her smelly, sweaty feet and erotic moans arouse you, and you get a boner. You're always fantasizing about your step-mom and the way she languorously reclines on the bed, giving you flashes up her skirt, drives you crazy. She even casually rests her hands on her chest as she enjoys her massage. Then she catches you sniffing her feet, but she isn't mad. She teases you about your erection and your arousal about her feet, and then she says she wants to get out of her work clothes. She strips off her skirt, showing that she's not wearing any panties, and her pussy is shaved. Then off her top goes too, and she starts massaging her breasts while you finish the footrub. She says that we both may as well relax, so why don't you sniff her feet while jerking off? She begins playing with her pussy too. It will be our little secret, we're both horny and need to take a load off, right step-son? It feels so good getting her feet rubbed like this, that she couldn't help but get turned on. She slips off her stockings, revealing slutty red toes, and tells you to suck them while she plays with her pussy til she cums. Finally, she has you put her toes in her mouth, or use her feet to jerk off with, whatever you want, until you cum for step-mommy's feet too.

I'm your and I want to try something new. You have a fixation on your step-mother and her pantyhose, and the only way that we can have a breakthrough, in my opinion, is to act out your obsession through role play. This controversial method will have to remain between you and me. I put you in a trance state, and then allow you to masturbate while I tease you, and lovingly welcome you as a sexual step-mother who embraces your desire for me. We're going slow in this session with only shared words of love and lust, and mutual masturbation. Enjoy the sight of your step-mother teasing provocatively, showing off her cleavage while you jerk off, her legs in nylons, her ass as she bends over in her pencil skirt. The mesmerization will make you feel like it really is her there in the flesh, welcoming you and wanting you. There is no need for shame, only love and desire. Your step-mother loves and wants you in every way, as much as you want her. I spread my legs revealing sheer pantyhose and rub myself to an orgasm while you do the same, and leave a trigger for you to book another session before bringing you out of trance and getting dressed.

You try to convince a married neighbour to buy some raffle tickets, but she has another kind of getting lucky in mind...

You come to my door selling raffle tickets, I'm the lady from the new family in the neighbourhood. You're nervous because I'm pretty and confident, I put my pantyhose-clad feet up on the coffee table, and ask you directly what you're selling. I seem bored that it's baked goods, and quickly turn things to my advantage. What if I bought 10 tickets, I say, leaning forward, and slowly pulling a 20 out of my bra. And what if I buy 10 more tomorrow, do you think my odds would be good? I hate to lose, I say, casually opening and closing my nylon-covered leg slightly. I tell you that I don't like wasting my money, I need to be sure to get what I'm paying for. I tell you that my husband is in the garage as I spread my legs wide. I'm experienced enough to smell a virgin, and I love young horny boys. I rub the crotch of my hose, and you can see my pussy through the nylon. I tell you to jerk your cock, that I know exactly the sound of my husband approaching. Just do what I say, and there will be plenty of raffle tickets in it for you, and some other things besides. Have you ever had your cock sucked? I want to taste you. I suck you down, gobbling your cock expertly and you're in heaven. You've jerked off a ton, but you've never felt anything so amazing, so wet, so slippery, so teasing, so all-consuming. You can't get over the way I look at you with lust, the way I lick your cock head, and get it all slippery with my spit, the things I say. You know you'll be coming back for more even before you cum in my mouth, and I pull the 20 back out and tell you to be sure to come back tomorrow.

You think you're all grown up now, fucking girls in school, but you still want your step-mother. In fact, now you can compare and see that my pussy is best. I cum easily and often. I can come with your mouth, and with your cock alone. My pussy is still so tight, and it milks your young cum every time. You're addicted to sex with your step-mother, it really is best isn't it, my boy? No one can deep throat like step-mother either. Today I want to show you something new. How to fuck a woman's ass. Not a a grown woman, with a big round ass like me. Of course it will come in handy for your little brats, step-mommy loves you and wants to do it right. I put my big butt in your face, you're crazy for me in a bikini. Then I remove it via the strings, and lay in the prone bone position, lubing up my hole that I cleaned out just for you. I show you how to open up my tight ass with one finger, then two, and lots of lube. With a big hard cock like yours, sometimes it helps to play with a toy first, like this buttplug. Jerk off for step-mother while you watch me put it all the way in, nice and slow then deeper as it gets easier. Look how step-mommy can take it all the way! Now put your big hard cock in my ass, sweetie, just the head, feel how tight it is? Now push slowly, listen to step-mother. Good boy, you're a natural. Fuck your step-mother's ass nice and slow like a good boy. Now faster, and watch! Mmmm feel how step-mommy is about to cum? My asshole is squeezing you. Let me milk your cock in a sweet anal cream pie as you cum with your step-mother. Step-Mommy is always the best.

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You're nervously sitting at a table with your girlfriend's sexy MILF of a step-mother after being fed a good meal. Her nipple is peeking out of her workout top, and she has no idea. She lectures you teasingly about being good to her step-daughter, then gets up and says she has to do the dishes, giving you an eyeful of her huge ass in shiny spandex leggings. She apologizes for her attire, saying she just came from the gym. As she does the dishes and chit chats with you about the usual Step-Mom stuff, you can't tear your eyes from her butt. She turns around to ask you a question and catches you staring. She just smiles and keeps on, but now she's bending over a lot, and moving her hips. Your boner is relentless. Your girlfriend texts to say she will be a bit longer, she got an urgent work call and is upstairs. You don't know what to do with your erection..but this MILF does. She comes over and says she knows what you want, and she puts her ass in your face, giving you a lap dance. You can barely control yourself, and you're torn between erotic madness and fear that your girl is going to walk in. Instinct takes over and luckily this woman knows what to do. She gets down on her knees, staring into your eyes and smiling, giving you a handjob. She tells you to hurry up as she jerks you off and you shoot a huge load, cumming on her pretty hands and arm, and she laughs, wiping it up with a dishrag.

Also see Spandex Tease: Stroke, Smother and Cum on My Ass , Spandex Vacuum Sucking and Step-Mom's Sexy Satin and Spandex

I'm your step-mommy and I've come in to tuck you in the grown up way. I'm wearing some sexy navy blue Victoria's Secret lingerie... I know all about your addiction to MILF porn. You can't hide from step-mommy. You think I don't know your friends call me a MILF...I even fucked one of them, maybe I'll tell you about that another time. But for now, you're going to jerk off for your step-mom's MILF body, you know you dream about it sweetie, now you can. Don't worry it will be our little secret. You're a big boy now and Step-Mommy will make you rest so sweetly. Jerk for my mature tits, trimmed bush and juicy pussy and sweet curvaceous butt as step-mommy strips down for you and spreads, encouraging you like a loving, dirty step-mother the whole time.

Also see A Step-Mother's Love , Learning to Fuck Step-Mother and Come Back to Step-Mother

At last, you're home for the holidays, arriving quite late on Christmas Eve. Your sexy, curvaceous step-mother awaits you dressed in only a short satin robe and maribou heels. She missed you and she missed your cock too. She begins to undress, unwrapping the best of your presents. Soon your erection is springing to attention, and she asks you to undress too. Your step-mother teases you, flaunting her ripe, mature body, her strong legs, her round, full ass that you love more than any other. She peels down the straps of her satin slip, revealing her perennially perky breasts. She talks dirty to you, then taking her in her hand, which you adore, her grip confident and experienced as ever. You're rock hard with anticipation, and she tells you to sit down after your long drive. Your step-mother mounts you, her breasts bouncing up and down as she takes her pleasure in your cock. Then she lays under the tree for you to take control, spreading her pussy and touching herself, eager for you to enter. You fuck her and soon it is hard to hold back, so she flips over for your favourite position--doggystyle. It feels so taboo to fuck your own step-mother on all fours under the family tree, soon you feel like you're about to lose control. She wants it, she needs it, and she asks for it. She wants your come deep inside her for Christmas this year, she wants to feel you coming in her as she comes on your cock....

Also see Fucking Both Your Moms , Hurry Up For Step-Mommy and Step-Mommy's First Date

I'm your sexy, youthful, wicked step-mother, always dressed in something erotic around the house, and we have a special relationship. We've fucked, we've sucked, we've masturbated in front of each other and more. I'm so proud of you for doing so well in school this semester that I want to give you a treat. Today I want you to jerk off while I play with a new toy I bought, to see if I can make myself squirt, then you can learn how to do it to me. Jerk for me step-son, pleasure yourself and give me a show, and I'll give you one. I'm very fertile at this time of the month, so we can't have sex. Jerk it for your dirty step-mommy, and I'll make my pussy juicy and wet with this Njoy wand. I have a deliciously powerful, wet orgasm, which brings you to the edge of orgasm yourself. I clean off my toy with my mouth and then ask you to clean me up, with your tongue. Lick my pussy step-son, while you make yourself orgasm. Then come in and kiss your step-mother, I love you step-son.

Also see Step-Mom Masked , Step-Mom Found Your Dick Pics and Bad Step-Mommy Jerk Off Instruction

I'm your step-mother and I call you into my bedroom to discuss your masturbation habits. I've found those dirty, crunchy tissues. I'm laying down relaxed in bed, and you're surprised my attitude isn't more strict. I confess that I understand what you're going through. At my time of life too, hormones go crazy and I'm wet all the time. I go through pair after pair of panties in one day. I've seen your browser history, step-son, I know what kind of porn turns you on. You love older, curvy women--real women, not I shamelessly flaunt my cleavage and as I say these dirty words, you can't help but get a boner for your own step-mother, and I encourage it.

Sweetly Stroking for Step-Mom , Masturbating with Step-Mom and The Step-Mother's Day Present

You're my sweet, special boy and I love our time together. I invite you to sit beside me on the couch, and you can't keep your eyes off my braless breasts under my blouse. I ask you if you remember the time I put oil all over my body and let you watch, then asked you to jerk off for me. I strip off my top and oil up my breasts as we go down memory lane. Your young boner responds automatically, easily. I tell you not to be shy, let's make some more step-mother-step-son memories. Don't worry, it's not if we don't touch each other in the naughty places. Stand up and put on a show for me, while I bring myself to orgasm, you'll do the same. Stroke it just how your step-mother asks, you're such a good boy.

Also see Hurry Up For Step-Mommy , Step-Mommy's First Date and Secret Time With Step-Mommy