Tonight, you and your Auntie are spending time together while your parents are out. She is technically your sitter, but you two have such a fun relationship that she hates to put labels on it. With her always trying so hard to play it cool with you, you know that you can get away with almost anything. So, when she offers to play a game of high/ low as a way to get you ready for bed you see a great opportunity to take advantage of the situation.
Rather than sticking firm to her ground rules, Auntie lets you choose the forfeit for each round she loses. Obviously, you want to have fun with this and even embarrass her a little. So, after a bit of resistance, your aunt agrees to strip off a piece of clothing each time she loses.
You are elated! It does not even matter that you have no control over the cards or the fate of the game. There is no way she could get a straightforward winning streak. One way or another she will be removing her clothes. Plus, she is only wearing a few items of clothing and you know it will be very easy to elongate the game and get the win you desire.
Clip contains: taboo ENF – auntie plays a game of strip high/ low with you that ends in your favor – embarrassed naked female
Related Categories: TABOO, GAMES, NUDITY/NAKED, EMBARRASSED NAKED FEMALE, CMNF / CLOTHED MALE NAKED FEMALE.
Keywords: tammie madison, aunt, taboo, nudity, strip games, nude auntie, embarrassed, losing and getting naked, nude in front of nephew.
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In the middle of the night you are awakened by the sounds of planes overhead and distant explosions. Mom runs into your room and drags you to a small closet in the basement.
“We should be okay in here” Mom says with a worried look on her face. She does her best to comfort you, but even she is scared and jumps each time an explosion sounds to close.
“I’m so sorry baby. I knew things were going downhill in, but I did not think we were already here. I think this is it, darling. This is the end of the world. We may not have much time, but I think we should make the most of it while we can. Is there anything you regret or wished you had done?”
Without even thinking about it you blurt out the first thing that comes to mind. You never wanted to go out as a virgin. At first, mom is shocked and a little saddened by this confession. She had just assumed that you were getting laid all the time. Then, her face lights up as realizes this is something she can do for you. Mom can make your last wish on earth come true by letting you lose your virginity to the woman you love more than any other.
Clip contains: apocalyptic taboo mom and son – mom comforts you while the world is ending – virtual sex with mom – virtual blowjob – loving mommy takes your virginity
Sex acts: virtual blowjob and virtual sex (cowgirl, reverse cowgirl and against the wall missionary) with mommy talk, ending with implied creampie.
Related Categories: MILF, VIRTUAL SEX, APOCALYPTIC, MOMMAS BOY, PERIL.
Keywords: tammie madison, loving mommy, mom and son, taboo, virtual sex, cum with mom, end of the world, apocaplypse, lose virginity to mom, confession, virtual bj, pov.
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You walk into Mommy’s room to find her in a bathing suit. Seeing her in that sexy, tight little number makes you forget why you came in here. As you stare, Mom urges you to go put on your swimsuit too so you can join her at the pool. Since you are still unable to speak, Mom assumes that you are nervous to be in a swimsuit and offers you some encouragement. “Would you prefer to wait and put on your bathing suit at the pool? I can take this off and change with you there.” When Mommy pulls down her suit and reveals her breasts you are completely captivated. She sees you staring at her lovely tits and invites you to touch and explore them. It is only natural for you to be curious and she wants to know just how wonderful boobs are. As you touch, you can tell that Mom likes it. In fact, it seems to overwhelm her and she pulls away. Mommy insists that you both need to continue to get ready and starts to remove her bathing suit. As it drops to the floor you know this is your opportunity. With Mommy bent over in front of you it is too much to resist and you step forward and enter her. Mom is both shocked and pleased. This is not what she expected from her boy, but she is not about to stop it.
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Before going for a run Mom likes to stretch legs and back from the comfort of her bed. However, today she has a little mishap when trying to get a deeper stretch in her back. Still determined to get out for her run, Mom calls you into her room to give her a helping hand. Each time Mom tries to target her lower back and thighs while stretching she gets a little stuck. If you could just help manipulate legs and push your body against her for a bit more pressure it would really help.
As you help move Mom’s body around and lean into her legs, you cannot help but get a little excited. The moans she lets out with each stretch a bit too much to take. When Mom accidentally pushes back into and feels your growing bulge she gets another idea. Maybe it would be easier if she were to just remove her shorts for stretching.
Finally, Mom decides that you two should forego the stretching altogether. It would be far better for her warm-up if she were to do something more energetic, like jumping or bouncing. The best way to get that type of movement is for you to be inside of Mom. Mommy wants you to be fucked and to ride you. She has decided that being pumped full of your cum would be the best possible warm-up and why would you ever want to deny Mom of what she wants?
Clip contains: taboo mom and son virtual sex – pov – mom gets turned on feeling your rock hard body up against her – creampie encouragement from mom – milf
Related Categories: MILF, MOMMAS BOY, OLDER WOMAN / YOUNGER MAN, STRETCHING, VIRTUAL SEX.
Keywords: tammie madison, pov virtual sex, taboo mommy, son fucks mom, helping mom stretch, horny mom, creampie mom, mom wants your cum, workout clothes, sports bra, milf.
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Mommy is so proud of you and your very healthy sexual appetite. She knows that you make the most of your amazing dick by jerking off often. But, what she does not know is when you last did it for Mommy. Don’t you find her sexy? She finds you very attractive. In fact, she gets turned on each time she notices just what a sexy man you have become. But, she wants more. Mommy wants to watch you enjoy that gorgeous cock while you look at her. That is not too much to ask, is it? After all, Mommy made you. It only seems right that you show some appreciation by giving her what she wants and masturbating with her.
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Hey, it’s only me. I was just coming to check *gasp*… What are you doing? Are you trying … to… to suck yourself? Oh my god. I did not think that was a real thing guys could do. How far did you get? Go on, just show me. You are already in position anyhow.
That is not bad. You seem so close. Maybe you just need to be a little harder and then it will slide right in. After all, I know you like to perv on me. No need to get all embarrassed now. It is no big deal. You are not the first guy to perv on his hot sister. Plus, I am genuinely impressed. I really want to see you achieve your goal.
So, why don’t we make this fun. Each time you get a bit more in your mouth, I will give you a bit more to look at. I want to see you take it all the way. Not only that, but I want to be a part of the big finale. I would love to watch you orgasm, cumming in your own mouth, and then kiss you to taste the cum on your lips and tongue. I want to make out with you, swapping your cum back and forth between my mouth and yours.
It looks so good. Keep going. Keep sucking your dick for me. Cum in your mouth and let your sister taste it on your lips.
Clip contains: horny sister catches you trying autofellatio and encourages you to keep going – taboo brother sister cum encouragement – cum eating instructions – sister wants to watch you suck your dick and cum in your mouth – mutual masturbation
Category: SELF SUCKING
Related Categories: AUTOFELLATIO, CUM EATING INSTRUCTION, TABOO, CEI, MASTURBATION ENCOURAGEMENT.
Keywords: tammie madison, sister, taboo, cum encouragement, suck for sis, self-sucker, swallow your cum, cum in mouth, sis wants your cum, taste your cum, suck and cum, horny sister.
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I do not wear these heels often. You probably have not seen them on me before. That is because I love to save these cheeky see-through wedges for one special purpose. They are my ball crushers. Despite the sweet and innocent appearance of these darling shoes, they deliver an impressive amount of power when slammed down on your feeble balls. These heels are perfect for the obliteration of your balls.
Clip contains: showing off my favorite shoes for ball stomping – giving you the opportunity to drool for my perfect feet in these cute ball crushers before I show you just what they can do
Category: BALL STOMPING
Related Categories: CRUSH, FOOT FETISH, CBT, FOOT DOMINATION, HIGH HEELS.
Keywords: tammie madison, ball crush, cbt fantasy, clear wedge shoes, pov foot worship, stomping on your balls, ball stomping, sexy feet, sexy heels, under my feet.
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There have been some complaints about your behavior. People are saying that you are being an absolute dick. Is this true? I am so disappointed in you, honey. No son of mine is going get and keep a reputation for being the biggest dick around. So, I’ve decided that the only way to stop you from behaving this way is to show you what it is like to have to put up with a huge dick.
That’s right, baby, dick for dick. Mommy is going to use her own cock to teach you a lesson. You have never seen what a giant cock I can grow, so understandably there will be some hesitation on your part. But, I am not putting up with any of your attitude today. Now is not the time for you to be surprised to find what I hide under My dress. I am going to make you suck and fuck this cock of mine until I am well and truly satisfied that you will be a good boy from now on.
Clip contains: futanari Mommy teaches son (POV) a lesson for being such a dick – made to suck Mom’s cock, take it up the ass, and do ass to mouth for being a naughty boy – taboo futa Mom and son scenario
Related Categories: FUTA, PEGGING, TABOO, MILF, POV SEX.
Keywords: tammie madison, futa mom, pegged by mommy, futanari punishment, anal, taboo fantasy, mom has a dick, milf fantasy.
Your sister has been asked to come over and look after you while you have the house to yourself. She is fine doing it, but finds it strange that you cannot be trusted on your own. How is it that you still don’t have your life together? Being the kind sister that she is, Tammie offers to help you.
When she starts talking about clearing out all the excess in your life, cleansing and clearing, you start to worry that she is going to try and push some meditation and wellness stuff onto you. She is always boasted about the benefits of some new fad. So, you are taken completely off guard when she tells you what she has in mind.
Your sister thinks that an enema is all you need. By cleansing your body, she says you will cleanse your mind and be able to sort yourself out. You are not totally convinced, but you know she will persist until you give in. Plus, she says there is a little bonus. Most guys find that there are some rather pleasant side effects from the feel of the water flowing in your asshole. That is Tammie’s favorite part. Not only will she help you clear out the debris with the enema, she will also help you achieve a fresh state of mind through an explosive, freeing orgasm. This time with your sister will change your life.
Clip contains: taboo brother sister fantasy where sis gives you an erotic enema encouraging you to stroke while you retain the water and orgasm to release everything – POV enema – JOI – jerk off encouragement
Related Categories: TABOO, MASTURBATION ENCOURAGEMENT, JOI, SISTER DOMME, POV.
Keywords: tammie madison, enema encouragement, joe, sister, taboo brother sister, erotic enema, jerk off encouragement, masturbation, cum encouragement, get off with sister.
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Honey, I know you don’t want to see this, but I need you to watch. I need you to follow their instructions. I’m not sure how many of them there are. I don’t even know where they have taken me. All I know is that they have me and they will only release me once you pay them the $50,000 fee. I know it’s a lot honey, but you’re going to have to withdraw from your college fund. If you don’t, they will simply keep me here, to use as they please, for as long as they want. baby, they’ll keep sending you videos until you pay them. They’ll keep filling me with their cocks and their spunk until you have raised the full amount. Baby, please help mommy. Please do what they say, or else you’ll just have to keep watching mommy get used by these monsters!
Related Categories: BONDAGE, CLOWNS, CUCKOLDING, DEEP THROAT, CREAMPIE.
Keywords: taboo, bondage, creampie, deep throat, tammie madison, forbidden perversions, clowns, horror, ball gag, consensual non-consent, sloppy blow job, fauxcest, mom son, cuckolding.
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It always a bit awkward when you have to spend time alone with your girlfriend’s mom. She is hot and doesn’t seem to be aware of the effect her cleavage and revealing outfits have on you. Usually you can cover up or hide your erection from her, but tonight she notices.
“There is no way I am letting my daughter go on a date with you while that thing is fully loaded. You better get to work relieving g yourself of that hard on. What are waiting for? Whip it out and get to work.”
You cannot believe that she is serious! How can you possibly masturbate right in front of her? When she calls up to her daughter to slow her date prep, you realize this milf is serious. Your girlfriend’s mom wants you to masturbate for her. She starts touching herself, revealing more, and teasing you. There is no way you want to pass up the opportunity to stroke and cum with an older woman, so you start doing as she says. The only difficulty now, is holding back so that you don’t explode before she counts you down.
Clip contains: taboo jerk off encouragement and instructions from your girlfriend’s – stroking for an older woman while your girlfriend is upstairs – cumming with your girlfriend’s mom
Related Categories: OLDER WOMAN / YOUNGER MAN, JERK OFF INSTRUCTION, MASTURBATION ENCOURAGEMENT, JOI, MILF.
Keywords: tammie madison, taboo joi, jerking for milf, encouraging joi, naughty mom, girlfriend’s mom, stroke for an older woman, jerk off encouragament, mutual masturbation, hot milf.
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