Mom Takes Pity On Your Tiny Cock - Miss Penny Barber

Mom Takes Pity On Your Tiny Cock – Miss Penny Barber

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.

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Caught Beating Off In Mom's Bed - Penny Barber

Caught Beating Off In Mom’s Bed – Penny Barber

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.

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Penny Barber - You Don't Have to Sleep on the Couch, Daddy

You Don’t Have to Sleep on the Couch, Daddy – Penny Barber

I come out of my bedroom for a drink of water to find you sleeping on the couch. Did you have a fight with Mom again? You know, I really hate to see you sleeping out here. Do you want to come sleep…with me? We crawl into my bed, but I’m awfully squirmy. You see, I’m not used to sleeping in my clothes. Will it bother you if I take them off?

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

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

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.

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

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

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.

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Special Mimosa Gets You Mother's Day Sex - Miss Penny Barber

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

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.

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Dick Pics With Mom - Miss Penny Barber

Dick Pics With Mom – Miss Penny Barber

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.

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

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

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.

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Special Easter Holiday Handjob From Mom - Miss Penny Barber

Special Easter Holiday Handjob From Mom – Miss Penny Barber

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.

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

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

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.

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