You’re hanging out with your Girlfriend at her place but you’ve only agreed to dinner because she’s been playing hard to get and well you’re sure after this she’s gonna give it up. Her mom asks if you can grab something from the top shelf. Well you’re sure you can score more points if you help out her mom. As you climb up her mom grabs your legs and ass. She says she’s just helping, you’re sure she’s just helping herself. I mean her mom is one hot MILF and you just noticed she’s dressed a little skimpy today. All this petting has your cock jumping. Your girlfriend reminds you that your both supposed to go to the store. You tell your girlfriend that your gonna stay back here and help “mom” while she goes out. Maybe “mom” will give it up before your girlfriend does. Are you ready to cum for Jen?

Get your copy of Roleplay 01: Girlfriends Mom Can’t Help Herself

You’ve been my neighbour for some time now. You’re always friendly to me. Most of the other neighbours are either indifferent or catty towards me. I love the way we flirt with each other, but I’ve never put any thought into it. So when I invited you in tonight for a drink I never thought we would end up teasing each other. Wait what??!! You’ve been spying on me??!!! Through my windows!?!! For how long??? Are you ready to cum for Jen?

Get your copy of Roleplay 31: Confessions Of A Peeping Tom

Your hot neighbour Jen came over for a visit. She always dresses slutty. I’m sure she gets more “looks” from the other neighbourhood wives then the husbands. She has this slutty reputation, but your sure it’s just talk. Are you ready to cum for Jen?

Get your copy of Roleplay 30: Alysha Is In The Other Room

Imagine going through candidates for a position at your business, and your first teacher crush shows up. She looks like she did when she was your english teacher. You had such a hard crush on her, the many nights dreaming about her and now she’s here. In your office. Still as hot as she was when she was teaching. Are you ready to cum for Jen?

Get your copy of Roleplay 29: Your Old High School English Teacher

I met my wifes boss, Jen at the christmas party. She seemed very nice. She dresses to impress, more like she dresses to capture. She was flirty with me that night, so I’m sure dropping by to talk about why my wife shouldn’t be too much of a problem. When your wife comes home from work crying most nights and “really doesn’t want to talk about it!!”, I figure, go and find out why. My wife has mentioned that Jen can be really demanding at times. I’m sure I can smooth things out a little and bring peace back to my life.

Get your copy of Roleplay 28: My Wifes Demanding Boss, Jen.

There I was having a little alone time when I noticed you staring, just outside my bedroom window. I’ve seen you there many times, it makes me wet knowing your watching. This time I had you call you out on it. I want to be your naughty neighbourhood whore. I need your hard cock, I just have to have it. Are you ready to cum for Jen?

Get your copy of Roleplay 27: Caught Gooning On Me

Your mom has never been someone you could ever talk to about, anything. Dad’s not around, ever. You can’t talk to any of your friends about this. Since you’ve been with Karen her mom has been treating you like one of her own. Karens mom Jen has been a rock for you and now that you need some advice you’ve decided that Jen is the only one who could help. You’re late to the game of sex and really know nothing. Jen is such a MILF, and she is your confidante in ways. Your sure she would have no problem helping you out. Besides Jen is a hot MILF. Are you ready to cum for Jen?

Get your copy of Roleplay 26:Girlfriends Mom Is A Hot MILF

Your grades have gone to hell and you seem extra distracted in class as of late. You’re failing! You’ve been invited to talk about what is going on. Damn your teacher is soo hot, and you just told her it’s her that is the problem. You can’t believe it came out that way. Something has come over you. Your lust for Jen is too much you feel as if your a passenger in your body. You’ve never had sex before and your making moves on Jen that your have never made on your girlfriend. Are you ready to cum for Jen?

Get your copy of Roleplay 25:The After School Meeting

You just had the pleasure of interviewing Jen for your vacant Sexetary position. Since you’ve promised her top salary you have to be sure she can “handle” the position. Today she’s going to prove herself by performing a few tasks for you. She’s very keen for the position. She starts by sliding you deep down her throat, only stopping to ask if your going to fill her mouth. As she goes on you feel her abilities are more then adequate. But she doesn’t stop there, she slowly removes her mini skirt… Are you ready to cum for Jen?

Get your copy of Roleplay 24:Hired A New Sexetary

You’re greeted this morning by Ms. Jen. You asked for an early morning wake up. You know that Ms. Jen makes sure your fully awake before she leaves. As she opens the door you are greated with a lovely Ms. Jen, wearing a crop top, grey skirt and thigh hi socks. You can’t wait for what Ms. Jen has in store for you. She teasingly asks if you have “morning wood”, then pries if she can take a peek. She waits in anticipation as you remove your covers. You can tell she likes what she see’s as a huge grin, followed by an excited look, covers her face. Are you ready to Cum for Jen?

Get your copy of Roleplay 23:Your Early Morning Wake Up