Ladies,

What is the most fun or interesting Role play or fantasy scenario that a gentleman has ever asked of you or that you personally enjoy experiencing,  Can be alone or with others.

I highly enjoyed the secretary/boss role and school girl/ teacher...the first one was memorable because it happen to be in a very large law firm (after hours) so we did it on every desk, and the second one.. I had the outfit pigtails and even a lunch box full of toys.. I love role playing because it is just fun and opportunity to experience new things and characters.

Over the years, there have been so many role playing scenarios.  Everyone was more enjoyable and fun than the last.  

I had a gentleman request that I was a real estate agent. His home was really for sale. I had to wear a suit and go to his house and actually try to sell him the house. He probably just wanted to hear my thoughts and ideas as a person seeing the house for the first time while having a good time as well, so we killed two birds with one stone. I was to show the home and them when we got the bedroom, I had to seduce him. It was really erotic and fun as hell!

Another gentleman was into Cosplay. I wear a costume where I was a caped crusader complete with face make-up, a mask, etc. and had to take him captive and have my way with him. That was great fun!

One time with a good client friend on mine, we decided to call an agency to send a girl over. We pretended we were engaged, I had never been with a woman before, and we wanted to do this before we got married. It was hysterical!  We had so much fun pretending with this girl.  I pretended that I had never been with a girl before and was afraid and she had to "make me like it"....lol....that was awesome!

On another occasion, a gentleman wanted to see his wife with another woman. They had discussed it, but never knew how to go about it. He suggested that I come to their hotel room under the pretense of an in-room massage. I brought my table, oil etc. and told the gentleman he was welcome to to stay. He told me to see how far I could go. If she resisted, obviously just continue with the massage. After about a half hour massage, I started caressing her breasts, and she did not say anything. I then intimately touched other parts of her body and she did not resist. But the end of the hour, we were making out and totally enjoying ourselves while her husband watched. It was a great experience.  

Another role play was a cuckhold situation. A gentleman and I went out and he wanted to watch me seduce another man at a bar and take him back to our room so he could watch me with him. This was fun! It happened in Vegas... (I guess not everything that happens in Vegas stays in Vegas)

On of my all time favorites was with Laura de Leon in DC. A gentleman supplied an entire script. We all worked together for an investment firm. He discovered that she and I had been skimming of the top. In order to keep our jobs, he wanted in and wanted to see us together. We had to beg him not to fire us, report us, etc.  It was great.  

There have been so many other wonderful role play adventures, the list goes on and on and on...the nurse, the teacher/student, the neighbor who seduces the young boy next door, etc. All in all, I think it's exciting and really fun! It certainly changes things up a bit. Keep 'em coming...I have a creative mind and certainly will go along with mostly all role plays and fantasies!

Always Sexy,  
Ton

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Well the most interesting/different one that I did was where some one wanted me to humiliate him about his penis size, or lack thereof. I was afraid of offending him but it seemed the meaner I got, the more he liked it. Had a follow up session with him and he had got  a penis cage for his cock with a lock on it where he wasn't able to get hard! All he wanted me to do was to tell him about how I was going to go out later that night and pick up a real man and have sex with my well endowed lover in front of him.  
It was my first time dabbling in that fetish and certainly my most unique.  

One of my most memorable one was when I was requested with a cheerleader outfit, pom poms and everything

On my list of things I definitely want to do is office secretary scenario or a teacher student one....mmmm
:

I would love to role play this....
True experience...years ago, when I was 26, I dated a lady who was 36, and she had a 16 year old daughter, One day, while I was waiting for my GF to come home from work, daughter and I were talking in the family room. Daughter comes over and sits by me on the sofa, and confesses that she has "peeked" in on her mom and I having sex. Daughter says she wants me to show her how to make love like her mom and I do,,,,,and leans in to passionately kiss me! Needless to say, I gently pushed her away and told her that could not happen.....(she is 16! and I'm dating her Mom!!)   But the fantasy still remains...so I would love to fast forward the timeline to find her again, at a more appropriate age, now that I no longer date her mom!

Sound like fun??

Had a guy want me to dress up like a chicken and "hatch my eggs" for him. Don't even ask what the eggs were and where he wanted to put them.

A gentleman once asked me to play the role of "the hot single lady next door". He wanted me to pretend that I was a friend of his mother's and that I was coaxing him from his teenage pubescence and re-creating him into a man by way of naughty seduction. The role came really easy to me and I got really into it. He actually had to "tap out" because he got a little freaked out. lol!!! After a few "safe" moments we resumed and the naughty neighbor next door had her way with him!!!

I've not been much for role play but Toni's response may have changed my mind!

The most interesting was priest/nun.  My inner Catholic  lschoolgirl was hugely tittilated by that one, and it was at the client's request. The most fun was Daddy/daughter. Ver taboo, and extremely exciting for me.  It gets me hot all over again just thinking about it