You can’t wear jeans and a T-shirt on Halloween, sweetheart. I was so excited to do fun stuff and pass out candy all night in our costumes. Don’t you like my space woman outfit?
I bet I know what you want to be doing alone in your room all night instead of celebrating spooky times with your Mom. Maybe if I play with your cock right now then you won’t have to skip Halloween to play with it by yourself later? I am willing to unzip my costume and let you see my perfect tits but I am only taking my costume off if you put yours on.

MILF, TABOO, COSTUMES, HANDJOBS, BIG TITS, MOMMAS BOY

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You’re laying back on the couch while you watch your step mom hurriedly get ready for work. She doesn’t know you’re there, so she’s rushing around with only her top & panties on. After one of her nipples begin spilling over her bra you can’t help but instinctively reach down and stroke yourself. Within minutes, your mom notices what you’re doing! She’s pissed. She doesn’t have time to deal with this right now, but to your surprise in her rant she commands you to pull your dick out. You like watching your step mommy so much? Show her. You are in no position to deny your mother, so you do as she says. Within seconds she’s got her hand on your dick – stroking you fast and hard. She makes sure to do her upturned piggy nose for you, seeing as she knows how much you like it from last time she caught you jerking it to her. When you don’t cum in a few minutes, she further commands you to grab her BIG bra that still has your cum stain on it. You oblige and soon she’s stroking you with the bra wrapped around your dick. With her tits bouncing and swaying as she strokes you, her piggy nose, and her giant bra on your cock you can’t hold back..and soon you’re cumming RIGHT into your step mothers hand!

MOMMY ROLEPLAY, BOUNCING BOOBS, BRA FETISH, HANDJOBS, BRAT GIRLS

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Sexy mommy Kristi is just about done cleaning up so she stops by her son’s room to make sure he cleaned too. When she pops in she sees her son lying in bed and he hasn’t done anything! His room is filthy, his bed is a mess… but that’s ok. Kristi is a loving mother and she doesn’t mind making her sweet boy’s bed every now and again. She climbs on the bed and straightens out the blankets then she turns around to talk to her son.
He has a…. weird look on his face. She can tell something is wrong. She comes closer and questions her son on what is wrong… but it doesn’t take long to figure it out. There is a bulge under the blanket… she suspects it might be…. but no, it can’t be!
But it is… her son has an erection… his first erection apparently! Kristi realizes what has happened but she doesn’t know what to do! An erection? Haven’t you ever had one of these before, she asks? Don’t you know how to take care of it yourself?
The poor boy doesn’t and he almost looks ashamed but Kristi snaps into loving mommy mode and reassures him that it is fine… it’s just an erection and they are easy to take care of! Here, she says,… let mommy show you how easy and fun it can be to make the erection go away… and next time you’ll know how to do it yourself!

MILF, TABOO, VIRTUAL SEX, MOMMAS BOY, HANDJOBS, CUMSHOTS

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Where did you dig up my old PowerGlove? I used to beat all the boys on this thing and then make them eat, well never mind. I would love to play but don’t be surprised when I blow you away. If you really want to make a bet on the game then there is one dirty thing we used to play for back in the day. Loser has to eat cum.
You better be sure you want to risk it because if you lose, I might help you make it but I am definitely making you swallow it.

TABOO, MOMMAS BOY, GAMES, HANDJOBS, MILF, CEI

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The office manager enters perfectly dressed and wearing glossy nylons. She doesn’t need to say much and fulfills the perfect office nylons fantasy, nothing could be better, until she comes in again the next day

FEMALE TRAINING, MILF, LOTION / OIL FETISH, MASSAGE, SLUT TRAINING, HANDJOBS

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Every year, you have to get a physical for school sports, which is never really a big deal…but this year, things have changed. It’s like you can’t feel a gentle breeze across the front of your pants without getting a huge boner! Not that you’re complaining but its gotten much bigger and its a lot harder to hide…plus, your doctor is pretty, and you’re sure that when she checks you for a hernia, you’re going to get a big one. You’re not sure you can handle that level of embarrassment, so you go to your mom, hoping maybe she can forge the signature or take to the doctor about skipping that step, but instead she suggests that the two of you “practice” an appointment so you won’t be so nervous about it.
You’re not so sure about it, but you go along anyways, leaving the room so she can “get ready,” whatever that means. When you come back, she’s wearing a lab coat and has a stethoscope draped around her neck, remnants of last year’s Halloween costume. She starts to ask you questions, which aren’t so bad…until she gets to the stuff about your penis. About night time erections. It seems a little much – surely the doctor wont ask these types of question? – but your mother is adamant, insisting that you answer. You try to do so but even talking about it starts to get you hard. Oh god, now you’re going to have to roleplay a hernia check with your mother while you’ve got a boner! Your mother, her hand wrapped around your boner…squeezing it…oh god….this can’t be happening…
…but then it is. Your pants are down, and your mother is inspecting your hard cock. She’s touching it and holding it and then…she’s asking about the little red marks. The chaffing. You admit that sometimes you jerk it too much, and she wants to see how you do it. What?? She’s serious, she wants to see how you masturbate, to make sure you’re not doing damage to yourself. Strange as it seems, you oblige, stroking yourself like you normally would until she stops you, pulling out some lube and telling you that such friction on your penis can be avoided with proper lubrication. You’re about to hold out your hand for some when she squirts it into her palm and gently starts to rub the head of your desperately sensitive cock with it, covering you in warm, slippery lube!
She starts to instruct you on how to properly touch yourself, demonstrating every stroke with her own hands! She shows you how to bring yourself to the very edge of an orgasm, then back off, building a huge load inside your balls. Her breasts heave under the crisp white lab coat as you stare down at her, stroking and massaging your cock and balls with loving tenderness. She brings you up to the edge and back over and over, until she announces that she needs to make sure you’re ejaculating properly, taking out a specimen cup from her desk. Holding it up, she strokes you faster, encouraging you to cum, finally, to empty your balls for your mother.

TABOO, MEDICAL FETISH, HANDJOBS, ORGASM CONTROL, EDGING GAMES, POV

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You’re laying back on the couch while you watch your step mom hurriedly get ready for work. She doesn’t know you’re there, so she’s rushing around with only her top & panties on. After one of her nipples begin spilling over her bra you can’t help but instinctively reach down and stroke yourself. Within minutes, your mom notices what you’re doing! She’s pissed. She doesn’t have time to deal with this right now, but to your surprise in her rant she commands you to pull your dick out. You like watching your step mommy so much? Show her. You are in no position to deny your mother, so you do as she says. Within seconds she’s got her hand on your dick – stroking you fast and hard. She makes sure to do her upturned piggy nose for you, seeing as she knows how much you like it from last time she caught you jerking it to her. When you don’t cum in a few minutes, she further commands you to grab her BIG bra that still has your cum stain on it. You oblige and soon she’s stroking you with the bra wrapped around your dick. With her tits bouncing and swaying as she strokes you, her piggy nose, and her giant bra on your cock you can’t hold back..and soon you’re cumming RIGHT into your step mothers hand!

MOMMY ROLEPLAY, BOUNCING BOOBS, BRA FETISH, HANDJOBS, BRAT GIRLS

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“Oh my god, honey, what’re you doing in here? Are you…masturbating?! Darling, I’ve always told you that’s wrong, you shouldn’t touch yourself like that – it’s desecration of your sacred, virgin body! Your perfect body is like a temple, and this is disgraceful, haven’t I always told you that?…so why didn’t you listen to me? Well, all young boys get erections, but didn’t I always tell you that if you get an erection, you just think about me – about how disappointed I’d be in you if you ‘took care of it’ with your hands – and it’ll go away? So? Why didn’t you do that? Oh, you did think about mommy…but it didn’t work?…”
“…Well, how could it have made things worse, darling? Surely you can’t be saying that thinking about your mother made your penis more erect?? Oh, my…oh my goodness, well…that’s…certainly not what I had hoped for. My goodness, I feel responsible! What…what could I possibly do to make it better, darling?…You want me to…what? Oh, no, I don’t think that would…well, that’s true. It would prevent you from masturbating. Well, maybe then that’s the best option. Ok. Well, ok, here goes…”

TABOO, MILF, MOMMAS BOY, HANDJOBS, BLOW JOBS, CUM IN MOUTH

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So my Son would not come down to breakfast on the first day of School. I went up to check on him and see if he was ok. He told me he was really anxious and nervous about the first day and meeting new people. I called my sister Scarlett to come by and talk to him with me. We went into his room to see him sitting there with his cock in his hands. We saw that he really had a lot of tension built up and he needed a release. We both sucked his balls and his cock until he was ready to blow. We then took turns massaging the cum out of his cock. His first day of school was a success!

TABOO, HANDJOBS, BLONDES, COUGAR, BLOW JOBS, MILF

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