Tag: Penny Barber

Miss Penny Barber – Special Easter Holiday Handjob From Mom

I need you to hop up, get out of these jeans and into your Sunday suit before you make us late. I will give you your Easter present now if you promise to hurry. I know you are too old for an egg hunt but these say they are for adults. Oh wait, these aren’t fun Easter eggs, these are sex toys! I guess you stick your thing inside the egg?
We should test this one out just to be sure but then we really need to run along to church. Oh that just slides right on there, doesn’t it. So stretchy and slippery on your nice stiff cock. This toy is actually pretty fun for Mom and it looks you are definitely enjoying it too. We are running late though so I need you to enjoy it a little faster. Maybe the sight of my bare breasts and wet pussy will help you cream your egg a little quicker.

TABOO, MOMMAS BOY, POV, ROLE PLAY, MILF, HANDJOBS

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Miss Penny Barber – Mom Gives You A Girly Make Over For Her Lesbian Fantasy

I was planning to spend an evening with a nice glass of wine and my big book of Playboy centerfolds because I thought you had already gone to bed, sweetie. I just really enjoy the photography and well, maybe I like looking at the pretty girls too. Not as pretty as you though. Oh come on, I bet you would make a lovely girl.
How about you slip on a bra and panty set of mine and we see if it fits? If you are right then I will buy you concert tickets but if you can wear my clothes then I get to give you a makeover. Looks like someone is excited by just the idea of wearing his Mom’s panties. Don’t worry I think we still get these on over your little erection. I can’t believe how sexy you look all dolled up. You do make a very pretty girl but I think you would look even prettier with your lips around my strap-on cock.

MOMMAS BOY, FEMINIZATION, TABOO, MOMMY DOMME, STRAP-ON, MILF

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Miss Penny Barber – MILF Sex Trance Ends In Spanking For Perverted Step-Son (HD MP4)

I was actually feeling proud of little Sammy for how diligently he has been working on his science experiment but then I discovered that he was motivated by something other than academic ambition. The dirty brat was trying to build a mind control device and he planned to secretly test it on me for his own entertainment. I knew from the way he was always trying to look down my top or up skirts that it was not going to be some cute show where he made me quack like a duck.
I was proved right when he finally snuck up and blasted me with whatever gadget he had been constructing. Too bad I had already sabotaged it. I pretended to be totally under his control at first and sure enough, he ordered me to strip within his first few commands. He barely even tested my obedience or awareness before he was grabbing handfuls of my tits and proclaiming himself to be a genius. I let him live his perverted dream of having his step-mom as a mindless sex doll for a little longer before I snapped him over my knee and into his nightmare. From thinking he had absolute power over my body to begging me to stop spanking his bottom in less than two minutes. At least he will have some memories of seeing me naked to comfort him during the long months of chastity ahead.

TABOO, MAGIC CONTROL, MOMMY DOMME, MILF, SPANKING F/M, COCK TEASE

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Miss Penny Barber – Sweet JOI With Mom’s Breasts (HD MP4)

Is my little darling all relaxed and cozy before we start playing with that hard little thing of yours? You know edging with Mom helps you to be an obedient boy and you always enjoy our wanking sessions more when you are nice and comfortable beforehand. As long as you stroke it exactly like I tell you, then you will get to see Mom’s big beautiful breasts before your thingy pops. I know you want to rush to your countdown and get that special feeling but first you have to show me that you can follow directions about how to touch yourself. One hands or two, slow or fast, just follow along because Mommy knows your cock best.

MILF, MOMMAS BOY, BIG TITS, JOI, ROLE PLAY, TABOO

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Miss Penny Barber – Mom Makes You Fuck Little Sister Bambi Belle (HD MP4)

I caught naughty little Bambi trying to seduce you into giving her a very explicit sexual education. As soon as I realized what you and your sister were up to, I put the bare bottom she had just been wiggling in your face over my knee for a quick spanking. If Bambi wants to show off her adorably tiny tits and puffy pussy while she learns about the birds and bees, then she will do it under Mom’s supervision.
I make her spread her legs to give her brother an anatomy lesson while I explain that she since thinks it is appropriate for her brother to see her in a thong then she will be allowed to wear nothing but panties in the house from now on. Bambi is not the only one who has to get naked though and it is only fair that she gets to take her time staring at your cock just like you did to her entire naked body. I even make Bambi describe your erection, since we are here to learn after all but she doesn’t get much past “big” and “hard”. Of course, this lesson will not be complete until you climb on the bed with that big, hard cock and fuck your sister with it.

TABOO, POV SEX, SISTERS, SPANKING F/F, MOMMY DOMME, COCK TEASE

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Miss Penny Barber – Masturbation Addiction Revealed To Prom Date By Your Mom (HD MP4)

I am so happy that you two are going to prom together. I was not sure my special little man would be able to get a date with his, you know, little problem. Oh you don’t know what I mean? I am surprised you have not caught him in the act by now. I know most boys love to play with themselves but my little wanker is just obsessed. I can’t count the times I have walked in on him either with his hand down his pants or his dick in his hand. Sorry if this is a little shocking, sweetie, but I just thought you would already know about his jerk off addiction. Speaking of your date, I wonder what is taking him so long to finish getting ready?

TABOO, EMBARRASSMENT, CLEAVAGE, MOMMAS BOY, MILF, MASTURBATION HUMILIATION

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Miss Penny Barber – MILF Teacher Transformed Into Slutty Stepford Mom (HD MP4)

I am not going to tolerate your lewd staring in my classroom any longer. I do not want to hear excuses for your behavior or blaming my appearance for your choices. From now on, I expect…
What was that sweetheart? I guess I lost my train of thought. Would you like some tea? How about some cookies? I only have store bought but I promise they will be homemade next time. I just want my darling to be happy and healthy. Is there anything else….
Nevermind, sweetie, I have something more important we should talk about. Mommy is starting to get very horny and she needs your help. Don’t you like the way my body looks? Maybe if I just take off some clothes so you can see as much of me as you like. I am not sure why you are hesitating to fuck me right here on this desk but will you at least show mom your nice hard cock? Pretty please?

MILF, MOMMAS BOY, FEMALE TRAINING, JOI, ROLE PLAY, TEACHER FETISH

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Miss Penny Barber – Sneaky Son Obsessed With Mom’s Jean Covered Ass (HD MP4)

I am a little confused when I find a very old pair of skintight vintage jeans mixed in with the laundry. My ass always looked great in them but they have been stored in the attic for years. Now I find them in with the clean laundry and my son is very keen for me to try them on. So keen that he doesn’t even give me a chance to undress myself and pulls my skirt down before I even know what is happening. I am a little embarrassed to have him see my butt in just a thong but try to just go along since he seems to really want to find out if the jeans still fit.
The jeans are tight but I can definitely still get them on and I have to admit my butt still does look great in these jeans. My son thinks they look so good we should take some pictures but for some reason he insists the photos would look better without a top in the way so he pulls my blouse over my head before I can react. When I started laundry today I certainly expect it would end with me topless, wiggling my hips, and posing with my denim covered ass popped out while my son takes photos of me. At least, I hope that is all he is doing back there.

TABOO, MILF, CUM ON CLOTHES, JEANS FETISH, ROLE PLAY, EMBARRASSED NAKED FEMALE

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Miss Penny Barber – Mom Blows Your Bully And Makes You Watch HD MP4

Hello there, sweetheart, and please say hello to my special guest as well. I know he used to pick on you a lot but he has really grown up into quite the handsome young man. It was his idea to do a video chat so you could learn about our new relationship. We both want you to see your mom unzipping your bully’s pants to play with his nice, stiff cock. How does it feel to watch the guy who used to give you wedgies sliding his dick between my big tits?
You can tell us both how it makes you feel when the three of us have dinner together next weekend. Try not to get offended when he makes some “your mom” jokes about all the things he has been doing to my holes. In the mean time, just relax and enjoy watching your Mom give your worst enemy the blowjob of his life.

TABOO, MOMMAS BOY, CUCKOLDING, HUMILIATION, MILF, OLDER WOMAN / YOUNGER MAN

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Miss Penny Barber – Mom’s Remedy for Sexual Frustration

I can’t help but notice your constant hard-ons around the house. Maybe it’s because I wear such skimpy lingerie all the time. Although I’ve also noticed you spending tons and tons of time on the computer every day. Your attitude has been sub par, too. Clearly you’re sexually frustrated. But instead of having you get a girlfriend, I’m going to deal with you myself. After all, as your Mom I’m already around all the time and I know your body and your schedule. You’ll be jerking off twice in the morning, twice before bed, once when you first get home, before you go out—and any other time that I think you need to. The instant you get an erection, you need to play with it immediately and try to cum. We’ll be making some changes to your wardrobe so that Mommy can always tell when you’re hard: tight jeans when we’re out and naked at home. Actually, are you hard right now? Well, what did I say? What can I do to help you cum really, really hard?

MOMMAS BOY, TABOO, OLDER WOMAN / YOUNGER MAN, FEMDOM POV, MASTURBATION ENCOURAGEMENT, JERK OFF INSTRUCTION

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