368 Video(s) Found for: All Videos

I understand sissy boys like you.

You know what happens when your father leaves out of town for his business trips don't you? Your step mom gets all dolled up for a night of slutting around town. You like to watch me prepare myself with heavy makeup and slutty but sexy clothes. I know you also play in my make-up and I am ok with that because I understand sissy boys like you. You know I will tell you every dirty detail of my... more

Date Added: 01/05/2024
Starring: Zoey Holloway
Company: ErosArts, Inc.
Running Time: 12 mins

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Big isn't bad, it's good!

Your father said you wanted to talk with a female about something. I know I'm not your real mother but glad you feel comfortable enough to talk with me. So what is on your mind? You have a freakishly large what? A large penis and you want me to tell you a female's opinion of it? Ok, let's see it. Oh wow! That is huge! But it's ok to have a penis that large. I'm sure there are many girls... more

Date Added: 12/31/2023
Starring: Raylene
Company: ErosArts, Inc.
Running Time: 7 mins

Will you help me measure my buxom breasts?

I'm so glad you're home because I am so confused by something that happened today. I went bra shopping and my old bra size doesn't fit me. I've worn the same size since I married your father years ago. You've seen my boobs, only in clothes or my swimsuit but tell me, do they seem bigger? I really need your help. I'm going to place this tape measure around my chest and you tell me what the... more

Date Added: 12/26/2023
Starring: Karen Fisher
Company: ErosArts, Inc.
Running Time: 8 mins

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Do you approve of the lifestyle?

Every thing feels better without clothes on. If it were up to me I would be nude the whole day but the world doesn't work that way so our lifestyle is restricted to just our home. I think your son is picking up on the way we live because he sure likes to watch me clean house on my regular cleaning days. Oh yes, he is here right now watching me. So long as he keeps getting good grades in his... more

Date Added: 12/21/2023
Starring: Alura Jenson
Company: ErosArts, Inc.
Running Time: 4 mins

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Stepsons 'little blue pill" problem.

All I was looking for was something to take this headache away. I thought the bottle of blue pills were aspirin or something equivalent but no, I had to stumble upon my dads Viagra. I instantly got a perma boner that wouldn't go away no matter that I jacked off four times. I was reading on the internet that if my boner didn't go away in a certain amount of time I would have to go to the ER.... more

Date Added: 12/16/2023
Starring: Mikki Lynn
Company: ErosArts, Inc.
Running Time: 5 mins

Let me explain a woman.

I don't want you to feel left out of any sex ed you may not be getting in real life situations so let me take this opportunity to explain a woman to you. I don't think you are getting enough interaction with women and maybe if I show you ways you can please a woman, you will feel more confident in your abilities. You are at the age where you should be going on lots of dates like my own son... more

Date Added: 12/11/2023
Starring: Syren DeMer
Company: ErosArts, Inc.
Running Time: 10 mins

You deserve this spanking!

When did you become such a damn snoop? Do you know where your sister sticks that vibrator that you have in your hand? Of course you know where that thing goes which is probably why I just caught you with it. I should tell her and your father about this or I could take matters into my own hands the way it should be done to teach you a lesson. Remove your pants and lay across my lap. You... more

Date Added: 12/06/2023
Starring: Austin Taylor
Company: ErosArts, Inc.
Running Time: 6 mins

I do this because I love you.

It's been one month and I am very proud of you for being such a good boy. Not everyone trusts their step mom enough to let her put him in chastity. I do this for your own good because I know those slutty women out there only want to get pregnant from you. Could you imagine trying to go to college and support a woman and baby? Of course not, so this is why I keep your manhood in a cage. Now... more

Date Added: 12/01/2023
Starring: Tara Holiday
Company: ErosArts, Inc.
Running Time: 9 mins

Road trip with stepmom.

My stepmom is such a hottie and she doesn't even know it. I can't believe I get to go on a road trip with her, just her and me. My dad is such an idiot in his cheap ways to try and save money. Oh well, his cheap ways pay off for me in a big way. The first hotel we stopped at for the night put us in a king size bed together. What was I to do? I couldn't sleep and had to rub one out. I... more

Date Added: 11/26/2023
Starring: Zoey Holloway
Company: ErosArts, Inc.
Running Time: 37 mins

Are you desperate for female attention?

How could you possibly have an erection at this time of day? I ask you to bring me cleaning solution and next thing I see, you standing there staring at me, with a hard on bulging from your pants! Ok, well I take that to mean you are in desperate need of female attention so go ahead and let's get this over with. I'm telling you to take your cock from your pants and start jerking it. I don't... more

Date Added: 11/21/2023
Starring: Candle Boxxx
Company: ErosArts, Inc.
Running Time: 10 mins