Tag: SMALL PENIS ENCOURAGEMENT

Miss Roxana Rae – Quality Time With Step-Mommy

Your happiness is so important to me. I see how you never go out on dates or bring women home. It makes me sad to see a guy like you never getting any pussy. I bet it’s because of your tiny cock. Well don’t worry, step-mommy doesn’t mind your little dick. I think it’s cute. In fact I’m going to let you stroke to me. It’s my job after all to make sure you are happy. In fact, why don’t you just give up pussy all together. You don’t need a woman, all you need is step-mommy…..

SMALL PENIS ENCOURAGEMENT, SPH, MOMMY ROLEPLAY, JOI, CUM COUNTDOWN, SFW

Continue to download

Painted Rose – Baby Dick Handjob and SPH Humiliation

You’re gonna be late and Mom promised Dad to get you to school on time and when she walks in you are jerking off. She’s not really put off but, more worried about you being late and concerned that it’s so small. She asks if you’re sure you are your fathers son. You’re struggling to cum. She tells you to just hurry so you can leave for school. She offers to help. Maybe you should wear a diaper to school since it’s so small… Since it’s so small she starts treating you like a sweet baby who needs to hurry up and cum. She baby talks you until you cum…

ADULT BABIES, SMALL PENIS ENCOURAGEMENT, SPH, HANDJOBS, MOMMY ROLEPLAY

Continue to download

Tatum Kelly – The Two Finger Method

You confide in me, your step-Mommy, that masturbation doesn’t feel good for some reason. I ask you to pull down your pants and that’s when I realize you have a very tiny cock. While holding in laughter, I demonstrate a way of jerking that I think will work for you: the two finger method. Clearly your palm is way too big for that little cock so you’re going to have to do it using two fingers instead. Thank goodness your step-Mommy was here to teach you that! Masturbation is important and your happiness is equally as important. Let’s give my method a try today…

MOMMAS BOY, SMALL PENIS HUMILIATION, SMALL PENIS ENCOURAGEMENT, COCK TEASE, EYE GLASSES, TABOO

Continue to download

Hot Wife Jolee – Mommy sees your tiny penis

Mommy is omg shocked when she sees you struggling to find your penis in your pants. Did mommy make her boy horny? Mommy asks her boy to drop his pants; it is ok to do in front of mommy. OHHHHH mommy is finding it hard not to laugh !! your penis is so small just like your poor father. Mommy feels bad for you and encourages her bot to embrace his tiny little dick with mommies help.

TABOO, MOMMAS BOY, DIRTY TALK, SMALL PENIS ENCOURAGEMENT, MILF, SMALL PENIS HUMILIATION

Continue to download

Ivy Starshyne – Regressing My Son

Oh, sorry, dear… oh… oh, my! Wow! THAT… THAT IS… WOW! Very small. Much smaller than I’d have imagined. I’m not saying this to be mean, honey. I actually think it’s cute. You know what it reminds me of? When you were a little baby.
It’s okay to have a little pee-pee, but with that baby dick, it would be more suitable if you were actually a little baby. Don’t you think? My little baby? Hey, little pee-pee. Just relax. Let this happen. You’re going to become my little baby again. Look how small that little winky is! Awww. So sweet. So tiny. So small.
Oh! Are you doing the pee dance? Do you have to tinkle? Let’s get you on the potty then. I’m going to hold your little dinky down so you don’t make a mess. My little baby. You look so cute! You’re getting so little, aren’t you? You’re even sucking your thumb, just as you used to… what a good boy you are! While we’re in the bathroom, I think it’s a good time for a bath. Let’s get you clean.
Let’s get those little baby bits clean. My sweet baby! And his little pee-pee! Oh, but little pee-pee is getting hard. Are you having fun being Mommy’s little helpless baby again? Yes, you are. I’m so happy, I love being Mommy to my little helpless baby. Let’s dry off the little baby and his cute little pee-pee. And oh my, wouldn’t you be so cute in some little panties? Look at that, they fit your just perfectly. No bulge, so they’re so nice and cozy, huh?
Now then, come to bed and suck Mommy’s breasts… I’ll stroke your little bits over your panties to help you relax, my little baby. You’re nice and hard again, hm? Look at that little baby precum spot on the panties! You’ve made a mess though, right after bath time. Aww. It’s so cute though! My little baby making a little mess in my panties. I’ll have to put you in diapers for those wet spots when I play with your winkie.
Aw, falling asleep? You’re such a good little baby… I’m so happy. You’re so sweet. You’ll be my little baby forever.

AGE REGRESSION, TABOO, MOMMAS BOY, BATHTUB FETISH, SMALL PENIS ENCOURAGEMENT, TIT SUCKING/NIPPLE FETISH

Continue to download

Taboo MILF Kristi – Mommy Loves Your Adorable Tiny PeePee – 720p

Hello my sweet son, you look sad. Do you need mommy’s help with something? Oh…. that…. again… Honey, how many times do I have to tell you? There is nothing you can do about your small penis, you were born this way and you just have to deal with it. Oh I suppose I can take a look and see if it has gotten any bigger if that makes you feel better. Let me have a look….
Sweetie… it may have gotten a tiny bit bigger but really honey, the truth is… you have a baby dick and since you do, you need to be treated like a baby. Your penis is never going to grow any bigger. It is always going to be a tiny little penis but I find that absolutely adorable! Mommy loves your tiny little peepee and I want you to be my sweet little tiny dick baby.
Now that we are treating you like a baby, it’s time you act like one. Come drink mommy’s warm sweet breastmilk and play with your adorable peepee until you cum so you can sleep good tonight. Come get your yummy snack, mommy’s tiny dick baby!

SMALL PENIS HUMILIATION, SMALL PENIS ENCOURAGEMENT, TABOO, LACTATING, JOI, MOMMAS BOY

Continue to download

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

Continue to download

Bettie Bondage – Mommy Loves Your Tiny Dick

Oh, honey, what’s wrong? Did something happen last night on your date with that…girl? You know I never liked her anyways. Come now, sweetie, be a good boy and tell mommy what happened…a hotel? Why on Earth would you rent a hotel room? Oh, my. Well, that’s ok, go ahead, tell me about it. I’m not mad. Your first time, with her? I mean…no, go ahead.
She said what?! My, that’s quite rude. No, I’m sure it’s not too small, honey. I mean, of course I haven’t seen it since you were little, but I’m sure it’s fine…she’s just a hussy. She did? Told the whole school? Oh, sweetie, that is so awful. You know, I could help you gain some, uh, perspective? If you showed me. Then I could tell you if she was right, if it’s not even worth it to try and um…fuck your tiny baby dick. Go ahead…
Well, that is small. But maybe if you’re hard it will get to a respectable size. Go on, get it hard for mommy. What’s wrong? Nervous? Hmm…well, maybe I could just touch it a bi…oh, see, there it goes. Hmm, still so small…skinny. Not girthy, like most girls like. It’s rare to find a woman like me who likes them smaller. Hmm? What’s that? Oh, yes. Mommy likes smaller penises. But finding another woman like that is going to be near impossible.
You know, I hate seeing you so down. I know this is going to sound crazy, but what if I helped you? You know, I did make you. And that. And I think maybe I made you the perfect size just for me. C’mon sweetie. It’s not like any other woman is going to want to fuck that. Just let mommy touch it…that’s it. Let mommy suck and fuck your tiny little cock. Mmmm, that’s perfect! Not too much bouncing, you’ll slip right out! Let me grind on your baby dick, sweetie. You’re going to make mommy cum! Now, it’s time to get that little dick to cum for me…I bet that little dick has a nice big load for mommy! Be a good boy and cum inside mommy’s mouth, darling!

TABOO, SMALL PENIS ENCOURAGEMENT, SMALL PENIS WORSHIP, SMALL PENIS HUMILIATION, MILF, MOMMAS BOY

Continue to download

Miss Roxana Rae – Tiny Dick Demotion

Look at that poor pathetic little thing. There is just no way you could ever be considered a man with that tiny dick. In fact, I think it is best if I just demote you from manhood to a more appropriate place in life. You need to be treated the same as others your size, cause you just can’t compete with the Alpha guys. I’ve decided the best thing to do is revoke your manhood and demote you.

SMALL PENIS HUMILIATION, MOMMY DOMME, LINGERIE, JOI, SMALL PENIS ENCOURAGEMENT, JERK OFF INSTRUCTION

Continue to download