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Anal (140)

You should go for a walk on the beach.. No, I want to stay here. I’m just saying it might be fun for you, maybe you could hit on some girls or something… Like without your step sister being there… Can you just leave the room please? Because, I need to take some pictures.. That’s none of your business… 39:44
Private Pictures
I’m sorry you had a bad day at work, let me make it better.. I can give you a massage… I’m your girlfriend, it’s my job to make you feel good. We can even use your favorite hole, I think it might be my favorite now too… 24:55
A Girlfriend's Touch
I’m sure you’re fine. I would just tell Alex to try it… Well, I’m his dad. I really shouldn’t look at my son’s girlfriend’s butthole… Okay, look, I can check it out but I’m sure it’s probably normal. Assholes are usually pretty tight. They just need a little training… 31:54
Guidance
Just go on a date with her. She’s really pretty and very nice… Oh this again. You’re not gay.. It’s just a phase. Or maybe it’s not… But how do you know for sure if you don’t try out girls? I’m your step mom, I just want to help you try something new. Maybe you’ll like it… 24:28
Free Sample
You can keep watching it. I’m not mad.. I’m curious, can I watch it with you? I’ve never really watched anal porn before… 27:11
Let Me Try
I don’t know anyone else who has as much experience as you.. I really want to try butt stuff and my boyfriend is to scared to try anything with me.. And you’re my boyfriend’s dad, so technically it’s not really cheating if you teach me… 32:51
Curiosity
Girls don’t like anal. At least I didn’t like it.. I tried it once… I shouldn’t even be telling you this stuff, I’m your step sister.. But there’s no way. You’re too thick, that wouldn’t fit in my butt… 28:17
The Right Way
Honey, you’re doing so good. You’ve been lasting longer and longer.. But today I have a surprise for you. We’re going to try something new. Yes, it’s going to be harder to last, but you’ll love it. Just remember what step mom has taught you… 27:04
Anal Edging
That’s just how I like to have sex. Is that weird? It just feels really good in my butt… You’re my big step brother, don’t make fun of me… Anal is fun. Haven’t you tried it before?.. We’re on vacation, you’re supposed to be having fun… 35:33
Vacation Essentials
I know it’s a first date but I need to find out if you’d even make a good boyfriend… Yeah of course I’m putting it in my butt first. Anal is my favorite… You’ve never put it in a girl’s butt before?.. Don’t worry I’ll tell you exactly what to do… 25:38
Goth Girl Priorities
You’re sure you don’t mind? You’re my step son, I know I should ask someone else.. Okay, I’m just afraid of making things weird. But I also want to make your father happy and let him use my ass. He’s just so big… You’re the perfect size to practice on… 25:27
Anal Training Mom
I don’t like you watching these videos.. I’m your step mom it is my business… They give you an unrealistic idea about what women like.. Anal sex? Really? You actually think there’s women who like having sex in their butt? Wait, you have? You’re telling me you’ve actually had anal sex with a girl in real life, and she liked it?… 31:11
A Successful Experiment
I know you cheated… Doesn’t matter, I’ll beat you tomorrow… Yeah there was definitely a lot of hot girls at the beach today… Don’t say that, you’re my step sister… Yeah of course, I’m horny too. That’s why I’m just going to jerk off. But we shouldn’t talk about that stuff… Why do you want to see it? That’s really weird… Okay fine, but only if you show me yours too…. 28:31
Safe Sex
Family vacation with your step daughter and her girlfriend get’s very interesting when you accidently discover they want to experiment with anal sex but they need to find a guy… 39:20
Vacation Anal Training
Listen, I need help… I need you to help me with something secret. Your big brother has a massive cock. And he wants to try anal with me. I need someone to practice on first… And I know your cock is just the right size for me… 21:15
The Right Size
No, I’m not mad. I’m just concerned. What if you get your step sister pregnant? What then? Exactly. We can’t have that happen. But don’t worry, step mom has a solution. I can show you how to have sex and be completely safe… 33:58
Family Planning
My daughter told me about what happened yesterday… Don’t worry I’m not mad. It’s perfectly normal for a young man to have certain urges… But you know you have to wait until marriage to do those things with my daughter. But in our family we have an old tradition… There is a way for me to help you with your cravings while not cheating. I can show you if you like… 22:16
Family Tradition
Why are you in bed with me again? You’re my little step sister. You should be in your own bed, not naked laying next to me. It’s not my job to teach you those things. You should find someone else… 21:45
New Things
I talked to your girlfriend.. Honey, I’m fine with you having sex… But you shouldn’t pressure her to do anal. She’s not ready yet. I know you really want to try it. But your girlfriend needs to want to try it too.. I don’t know why you’re so obsessed with anal. Have you even done it before?.. 27:52
As Good As It Looks
Step dad, relax. It’s not even that big. It’s just a butt plug. I don’t get it. When I put things in my pussy, that’s fine with you. But when I do butt stuff you get embarrassed. Just film it. Guy’s love buying anal videos. It’s not like you have to help me put it in or something… 26:31
World's Best Step Dad
Oh, that doesn’t bother me. Everyone jerks off. Don’t be embarrassed. Actually, what are you watching? I’m just curious, that’s all. Relax, I won’t tell your mom… Oh wow, anal sex. My favorite. My husband used to fuck my ass constantly. I miss that to be honest, things are different now.. I’m jealous, you probably do anal with girls all the time… 34:21
Essential Needs
I’m glad it’s going so well with your girlfriend, honey. I knew you’d do great after I taught you a few things… Oh wow! Your girlfriend wants to try anal? She must really like you sweetie.. No, there’s no reason to be nervous. Step mom can teach you that too. It’s very easy if you do it right… 22:27
Just Practice
I just need some more pointers. I know you don’t like talking about this stuff because I’m your step sister, but who else am I supposed to ask. Managing spicy accounts for girls is your job. And I know you’re really good at it. Please, if you want to be a really good step brother you would help me grow my account. You’d just be helping me make more money, what’s weird about that?… 33:25
New Management
You’re my best friend. I don’t want to mess that up. But it’s not that I wouldn’t want to date you… It’s just.. I have very specific needs… Like sexually. I need anal all the time. You don’t seem like you’re a guy that would be into things like that… 26:34
Anal Required
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