Little background in my mid twenties I was dating a divorced woman, 10 years older, newly divorced who was a research doctor who was from Boston (her accent was nails on a chalkboard) who dated and married the same man since she was 16.
She was a workout freak, even competed in a local Fitness Competion, she was just really tone and firm, not really masculine, about 5’5, tight frame with fantastic breasts, body, short blond hair (Peter Pan cut) and crystal blue eyes.
Due to the age difference we committed to just having fun and not letting it get serious because neither of us wanted it.
She traveled often and she would occasionally fly me out to visit her.
During the holidays she kept telling me I have to see NYC in the winter so she had a trip to the city (staying in Newark though) and she flew me out.
My flight was delayed and we were talking over the phone and she was already drinking (as was I) and she asked me if I ever role played.
I honestly have never, so I told her so.
She just laughed and said she had this fantasy of being a high class call girl and asked if I was game for it.
I replied sure, but asked how we were going to set it up.
She left a key for me at the hotel, she was going to go shopping, get ready and to call her as I landed.
Hour and half later I call her, goes to voice mail and I just tell her I am here, grab a shuttle to the airport, check in, head to the room and clean up.
After a about a half an hour the room phone is ringing and ringing so I finally pick it up.
“Sir, this is the front desk, you have a guest is it acceptable to give her access to your room?’
‘Sure’ I say and just hang it up.
About 5 minutes later I hear a knock on the door, walk over and open it up.
And there she was, beautiful, crystal blue eyes, she was wearing a mid length black coat, very form fitted skirt, black nylons and black high heals.
She puts her hand out and says hello, she is Bianca (that wasn’t her name) and I took the que and gave her my name.
I invite her in and she comes in, ask her if she wants a drink and she says yes.
So we walk into the sitting area and I ask to take her coat and she take it off and she was wearing a black sleeveless dress with an open back, she looked stunning and she has a large purse and I set it down for her.
So she asks me if I do this often and tell her yes, I do but never with anyone as beautiful as her and she blushed a little.
So she says, “you have paid for the night, my safe word is cinnamon, I am saying that because I am really good with anything but if I am not comfy I will let you know, understand?”
I said yes
“So what do you have in mind?” As she crossed her legs intentionally showing me she had on thigh highs which she knows drives me crazy. I just said, “you are the pro”.
“Well how about if I freshen up?” and she headed to the restroom.
About five minutes later she comes out in heals and thigh highs only and sits back down in the chair and grabs her drink.
She looks at me and says for me to “sit here” which was a chair across from her. And she stands up and walks to her bag and she says, “I will get us started” and she bends over across from me and my heart is racing I am so turned on.
She grabs an a few things out her bag and threw them on the bed, I didn’t pay attention to what she threw because she pulled out a rather large vibrator.
She sits over on the corner of the bed right across from me and she hits the switch on the large dildo and I hear the hummmmm.
She starts to rub it on her clit, staring me right in the eyes and starts working it on it, she is making small moans as she does it, I go to stand up and she tells me very direct, “sit down, I don’t want you here yet, please.” So I sit down and watch her slide lean back and with her one leg pulled back as she penetrates herself with the vibrator staring at me with droopy eyes but not moving from my gaze.
After 2 or 3 minutes of intense silence she begins to climax.
She then stands up, turns around and kneels on the bed so I am staring right at ass and she kneels down on the dildo and inserts it, she positions it so she can ride it while I am watching her tight little pussy grip that large didlo from behind as she is riding it.
She says, “play with yourself” so I stand up and pull my pants down and my cock is rock hard so I start to slowly jack off, and she says “come to this side so I can watch you” so I pull my pants off and walk over so she can watch me stroke my throbbing cock.
A few seconds later she commands me, “stand on the bed so I can suck your cock while I am getting fucked” and man I almost tripped on the bed but I stood up and slowly fed my cock into her mouth. She is slobbering on it and cums again and has a mouth full of my fat cock and is breathing hard from her mouth as it may have been one of the hottest things I have ever experienced.
She finishes her climax and peels off the drenched dildo.
She looks at me and on all fours she crawls over to the pile of stuff she threw on the bed and says she needs some help with this.
It was a ball gag, she hands it to me and turns aroubd and tells me, “be gentle putting it on, after that you have to remember, I am a whore, your slut for the night, we aren’t hear to make love, I am here for you to use me”.
She leans back and I see there is a set of handcuffs.
I lean her forward and cuff her hands behind her back and push her back on the bed.
I begin to eat her pussy and she is making muffled groans. I grab the big vibrating dildo, turn it on and slowly insert it in her pussy. I am working it and it was big, so angled it up and then l leaned in and began to lick her clit while I am fucking her with the dildo.
She is going insane. She came once pretty hard and was squirming, I asked if she wanted it? She nodded and I told her I was going to do give it to her, I was going to fuck her hard but I wanted to how many times I could make her cum with the dildo and sucking on her clit.
She came twice but the last one she started to shake, almost like convulsions, and she was fair complected but her face and chest turned flush red and her back arched, moaning loud and then she squirted the dildo out and sprayed cum all over.
She was breathing hard and I reached over behind her head and unhooked the gag, flip her on her side and grab the links of the handcuffs and drag her to the edge of the bed.
My cock is rock hard and I spread her legs and step up behind her and slide my pole inside her and once I get good depth I grab the cuffs as her hand are still cuffed behind her and use them to pull her back on my cock as I am beating her pussy up.
A few minutes I drop a load deep into her.
I grab her again by the cuffs and put her in the middle of the bed.
I lube up the dildo again and tell her to fuck it, I sit down spread eagle right in front of her while she is riding this giant dildo.
I grab her by the hair to bring my cock back to life and shove her face below.
A few minutes later I get up and drag her by the ankles to me by the edge of the bed, her beautiful ass is facing me and I put the dildo back in her pussy and tell her to start fucking.
I creep up behind her and lube up my thick cock and start working her tight little assehole, she stops fucking and playfully, but firmly spank her on the ass and tell her to keep that fucking dildo in her tight little pussy.
I finally get all the way in, I am stretching her ass out, she is breathing hard, moaning, but I have her hands still handcuffed and holding her up on both the dildo and my cock.
I am ready to cum and a shoot a huge load in her ass but she starts riding the dildo hard and she cums ones last time.
She turns around and says she is done, she can’t take anymore.
I took the que, unlocked the cuffs and asked if we were done?
She half laughed and said yes but don’t fuck me in the ass again!
We ended up watching a NY rangers game but with no more sex, she was literally done.
We would go on and use the role playing in a few ways, strangers meeting, secretary/boss but we never did that one again – and yes it happened however she was not happy with me fucking her ass.
Source: reddit.com/r/gonewildstories/comments/cb3r3m/ever_role_play_mf