Tag: Penny Barber

Miss Penny Barber – Mom Indulges Your Foot Fetish In Her Office

I am really glad you came to visit me at the office today but I am also so tired after this long day, especially my feet. It feels so good to finally slip off these high heels.Well thank you very much, I think I look pretty good in these fishnets as well. I would love a foot rub, you are such a sweetheart.
What would really feel great would be to get out of all these office clothes off so I can feel your fingers on my bare feet. Even with my tits and ass out, I can tell it is my toes and soles that are turning you on. I am sure you thought you were being sly but go ahead and pull out that cock. I want to see how hard you get from looking at my feet and I may even let my special little footboy do more than look.

TABOO, MILF, PANTYHOSE/STOCKINGS, MOMMAS BOY, FOOTJOBS, FEET JOI

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Miss Penny Barber – Video Game Bets and Forced Cum Eating with Mom

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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Penny Barber – Bribing Mom For A Blowjob

I hope you know that I am very proud of your recent success but don’t you think you might be getting a little carried with all the custom suits and always flashing your cash around. I am sure it is quite stressful to work such a high pressure job but I am not sure spending so much money on fancy watches is going to help. Of course I would love to hear your idea for better ways to spend your money and relieve your stress, honey. Wait what? One hundred dollars… for a blowjob… from me?
I thought you were joking but that big, hard cock tells me you’re serious. I guess a hundred bucks for one blowjob isn’t that bad of a deal. What if I strip naked and then you can decide if you really want Mom to suck your dick for money.

TABOO, MILF, SUBMISSIVE SLUTS, POV, BIG TITS, MONEY FETISH

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Miss Penny Barber – Mom Takes Pity On Your Tiny Cock

Your date got tired of waiting and finally left. What is wrong, honey? You were so excited about your first date. Oh. That is just silly. It can’t be so little that you are scared to even go on a date. I am just going to take a look because I am sure your dick is not nearly as small as you think.
Ok, well, even Mom is wrong sometimes. You really do have a tiny cock. It’s cute though and it sure does get very stiff. I think I know how I can cheer up my little man and his very little man. You penis is a little small for a handjob but I can give you a nice two finger job though. I bet you would also really love to find out easily Mom can fit your entire tiny thingy in her mouth.

MOMMAS BOY, MOMMY DOMME, SMALL PENIS HUMILIATION, SMALL PENIS ENCOURAGEMENT, TABOO, MILF

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Penny Barber – Caught Beating Off In Mom’s Bed

I am sorry you had a fight with your girlfriend, I mean your fiance, but I am more than happy to have you spend the night, sweetheart. Why don’t you snuggle up and tell me what this big bad fight was about? Well, maybe it can wait till morning.
…
I cannot believe I just got woken up by my son beating off in my bed. No need to stop I already saw what you were doing. Oh I guess you want me to do it for you then. There is no point in arguing since we both know that Mom always knows best. It’s not like you have anywhere else to go even if I didn’t have a hold of your dick. I don’t think a young man with such a hard on for his Mom needs to worry about going back to his girlfriend anytime soon. This might be the most action you get for a while.

MOMMAS BOY, COCK TEASE, ROLE PLAY, POV SEX, MILF

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Penny Barber – Mom Plays Slutty Dress Up To Get Your Grades Up

I was so surprised to get a phone call from your teacher that was not a glowing compliment. What has gotten you off track this semester? Sweetheart, being horny is normal and not an excuse for poor academic performance. What do you mean are horny for something “weird”? You can tell me and I promise I will do whatever I can to help you get your grades back up.
Wait, you want me to wear what? Stick that thing where? Oh goodness. Well, if dressing up in this slutty anime costume and wiggling my ass in your face with this plug in my hole is the only way to get you back to straight A’s, then I guess that is what I have to do.

TABOO, MOMMAS BOY, COSPLAY, BUTT PLUG, POV SEX, MILF

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Penny Barber and Ella Nova – Mom And Ella Nova Tease Your Tiny Dick

Your sister and I are so sorry that your big date turned out to be a prank, sweetie. I guess you will just have to stay in with us tonight and we will do our best to make you feel better. Looks like you were expecting to get laid tonight because we can definitely see the little tent in your pants still. Or is that from Mom and sister wearing lingerie around you?
It might be for the best that the mean girl did not go out with you since I can’t imagine she would be very kind to boy with such a small package. We can’t even ask one of Ella’s friends to take you on a pity date with a dick like that. Think how embarrassing that would be for your sister if everyone at school knew her brother has a tiny penis. I think the best your little cock can hope for is some playtime with Mom and sister because we feel sorry for you.

SISTER DOMME, HANDJOBS, SMALL PENIS HUMILIATION, MOMMY DOMME, SEXUAL REJECTION, TABOO

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Miss Penny Barber – Special Mimosa Gets You Mother’s Day Sex

I am so lucky to have such a darling son who brings me breakfast in bed on Mother’s Day so I don’t have to put on clothes for brunch. The gift you got me is also lovely even if I am not sure what to do with this little, um, sculpture? These Mimosas must be going straight to my head because I am really feeling flushed and I don’t think I can wear this robe another second.
What did you put in this drink, sweetie? I am starting to feel a really strong need to take off this last bit of clothes I am wearing and I also feel much bolder about admitting that I know your “gift” is a butt plug. Does my special boy want to see me being naughty? Is that why you made your Mom’s drink extra special this morning? I have a feeling if I agree to put this plug in my ass then you are going to want put something in my pussy too. They do say a nice hard fuck always makes the best Mother’s Day present.

MILF, MOMMAS BOY, TABOO, BUTT PLUG, POV SEX, MAGIC CONTROL

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Miss Penny Barber – Dick Pics With Mom

I did not mean to walk in on your little photoshoot but since I am here, we may as well get some better dick pics for you. I can get it from angles that will make it look bigger but first let me make sure it is as hard as possible. I’ll just get my tits out and play with your cock a little before we snap any more. You have a very nice dick, dear, and I just want to make sure you have some pictures that make you proud. I mean it really is very, very nice. Actually, sweetheart, I think your cock would look the best after it is has been freshly fucked.

TABOO, MOMMAS BOY, COCK WORSHIP, ROLE PLAY, MILF, HANDJOBS

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Miss Penny Barber – Mom Gets Naked In Public For Your Birthday

I am so flattered you wanted to spend your birthday with your Mom but I think you are pushing the birthday boy thing a little too far. Just because I have had a few glasses of wine does not mean I am going to flash my tits at you in this restaurant right now. You really are a very dirty boy. Maybe a little naughty game of public truth or dare as a birthday treat will be ok.
I can’t believe I am showing my bare ass and breasts in public like this but I have to admit I am definitely getting turned on. Do you think Mom can get herself off before the waiter comes back? I know you want to watch me try at least.

PUBLIC NUDITY, MILF, MASTURBATION, PUBLIC FLASHING, MOMMAS BOY, EMBARRASSED NAKED FEMALE

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