This may seem strange but you're the only one I can talk to. My boyfriend broke up with me because I wouldn't have sex with him. I told him I would get his cock off anytime he wanted but it would have to be with my hands. I think that's a pretty good deal, he didn't. So here is my dilemma. I have to know that my hand job wasn't the reason he broke up with me. I mean if this is as far as I... more

This has become problematic. You know what I'm talking about. You can't keep your eyes off my tits! It's embarrassing and everyone in the family has noticed. I'm surprised our parents haven't said something to you. Ever since they got married and made us siblings this whole family structure is askew. What kind of weird family do you come from anyway where you would get a boner from... more

Ok so you know my best friend has a crush on you. The thing is I want to go with my boyfriend and her to the prom but she needs a date. This is where you come in. Don't shake your head no! It's super easy. All you have to do is be her date for one night. It's not like I'm asking you to take one for the team and fuck her. What would make you change your mind? Ugh, really? you want me to... more

I'm glad my step-mom is gone. This gives us a chance to talk about something that might be awkward, at least for me. I'm sure you've heard of the term step-daddy issues. I mean we both know you aren't my real step-dad. My issue is I find you hot, as in I have a crush on you. You're the nicest man I know. You're really attractive and I feel a deep connection to you. It's the kind of... more

This started out as fun didn't it? I mean the harmless, flirty texts when our spouses weren't looking. You do look so much like your step-brother, my husband that it was kind of like I had two of you to flirt with. The family would totally freak out if they knew we were in a bedroom together right now. We have to stop the flirting before it ruins everything. We both know I won't ever fuck... more

Have you heard of a thing called camming? It's web camming on a site where I get naked and show guys my body while they jerk off. I've been doing ok but found out if I can use a real dick in my shows I can make more money. I don't have a boyfriend so this is why I called you in here. Would you be my web cam dick? You don't have to show your face. No one has to know I'm jacking off my... more

This doesn't have to be awkward. Hear me out as I explain why it's time you get shown the right kind of appreciation for your generosity. You are the most giving step-father in law a woman could ask for. Not only have you let your step-son and I stay here rent free while we continue our education but you also chip in when we aren't able to meet surprise expenses. I don't know of any other... more

I'm a little pouty tonight step-daddy. I got dressed up to go on a date and my boyfriend blew me off to go hang with his friends! The most sucky part of this is I was planning on being naughty with him, as in giving him myself for the first time. Now I see that he doesn't really care about me. I'm so tired of immature guys, I really am. My step-mom got lucky with you. You're so sympathetic... more

I'm glad we had the same idea of getting away from all those boring parents in the den. How can they spend hours upon hours playing bingo? They won't even notice we're gone. Playing with you is going to be so much more fun. I've crushed on you for awhile. I never thought I would get to touch your cock. You know how it is when you like some one and you are so curious what their private... more

Can you grasp the fact you're going into the military? I can hardly believe it! I mean I'm so used to you being home for me all the time. What am I going to do without my big step-brother around to protect me and keep the dumb guys away? Hey, remember that game we used to play last year? You know the one where I jerked you off just to see how much cum load you produced. Remember you ate all... more