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

Remember a few weekends ago when I threw that party. Yea the BBQ that went strong ’till 3am. No, Deb! I did not get so smashed I had to lay down for a half an hour. Actually I went up to my room to grab a sweater. When I got there I heard something in my bathroom. I swear the cat was stuck in the shower again. But when I opened the door expecting the curtains to be cut to shreds, it was Ryan! Yes, Ryan from the house at the stop sign. No, no. He wasn’t “using” the bathroom, he was in there jerking off to a picture of me. It was on his phone! I have no idea how he got it. I guess I was a little tipsy. I mean he looked good, and his cock was massive and so hard. I had to touch it. Yes I did. It was so warm, and hard. No Deb, I did not leave him be… Are you ready to cum for Jen?

Get your copy of Roleplay 22:Horny Jen Catches You Jerking Off

Your stepmom’s sister invited you to one of her famous parties. You know those parties, it’s mainly family with a sprinkle of their friends. BORING! But it is family and Auntie is a MILF. You can always count on Auntie to be wearing some revealing clothing, last time she was in a T-shirt with a neon-string bikini underneath. She always provides great spank bank material. She is “family” but not really, so it totally legit, right??! What’s a horny University kid supposed to do anyway, I’m sure at this time in my life I’m hard wired to not look. Are you ready to cum for Jen?

Get your copy of Roleplay 21:Stepmoms Twin Sister

First thing in the morning there’s a frantic knock at the door. Great news, the slutty MILF next door has some kind of emergency. You’ve seen her around, how could you not notice. She’s this hot little thing and dresses in all types of revealing clothing. This morning she has on a cropped shirt, thigh highs and a short mini skirt. You’ve added her to your spank bank so many times and she’s here asking for help at 8am! Of course your gonna go over and help her out. Maybe if your lucky you will catch a glimpse of her in a revealing pose or something. Worst case you will make a good impression and can possibly hang with her under better circumstances.

Get your copy of Roleplay 20:Jens Emergency

I’m desperately looking for work, I’ve been unemployed for some time now. I’m so excited to cum down and interview for you. I’m sure that I can give you exactly what you are looking for. I understand that you’re looking for a personal assistant. What was that!!?? You want an attractive assistant who will show cleavage. And you want to give me certain responsibilities. I’m sure I can get you off, especially at the office. I’m so excited for my new job, are you ready to cum for Jen?

Get your copy of Roleplay 19: Desperately Seeking Work