Would He Dare?

There is a gift in someone who dares to be so rough with me. Most men would never dare. I need to know that a man will be so bold, that at least he is capable of this sort of wielding. Then I can trust him. The flimsy men, the ones who would never dare to hurt me, to see me flinch, to bend me over and take me anywhere, anytime; I have no use for. Their trepidation is suffocating to me. And reflective of their behavior outside the bedroom. It always is. You can tell a lot about someone by how they fuck: Timid or decisive. Experimental or staid. Hard-driving and fierce or languid and droopy. My selection criteria is all about this crucial element: Can this man take charge? Does he dare? "6" The 400 Blow from Beautiful, Depraved

When I was an escort, I often wondered that before I met a new client. I wondered if they would take charge or be timid. Most of the men were kind of in middle ground. They didn't want to tell me what to do but they wanted me to be a slut. The bigger slut I was the more they were turned on. Begging, eager, lustful, passionate, attentive, wanton, wet and ready to do anything and they would become repeat clients who tipped. And well I like sex and liked my job so often I was able to pull all those things off pretty easily. It was exciting and I often got turned on with anticipation before the client even walked in the door.

I had a few clients that dared...they took charge. And were rough in a good way. I would leave feeling well used and spent. One of those clients was an older man that I have wrote about before. He was close to 70. And he had a beautiful huge cock. And would take me in many ways.

Let me back up a bit....and post something I wrote about before....

There was a whole community - just like the BDSM community - there was a sex industry community. We had forums, parties, socializing and such. There was a man that kind of rallied the "community." He did interviews and a "date" with the escorts and then after he would basically write up a review along with the interview and post it to the escort forums. When he would do this the girl would get a lot of good advertising. Well this man did one of me with a little bit of a BDSM twist. I was out about my BDSM interests but it was also known I didn't really engage in it unless I got to know the person. And even then I really was selective. I did some rough sex type of things and spanking but that was about it.

So after the interview I got quite a few gentlemen that would see me several times and then mention the BDSM and their interest in it. Very few of them from the bottom and several from the top. For the most part it is as I said above most of them just wanted someone who enjoyed sex and was very wanton. But I did have a few that wanted to do some BDSM elements in our time together. And one of those gentlmen is the one I mentioned above...he talked about the interview in his initial email to me...and that was unusual as they usually were to shy to bring it up right away. It would take a few appointments before many of the men would mention the BDSM. But this gentlemen did and he had a reference for me to call one of the other girls in the community. He didn't say in his email what he was wanting but he mentioned the interview so I knew it was something more then just a regular appointment. But I told him I would have to meet him first.

So on our first date/appointment he showed up at my hotel room with a couple of diet cokes and said he wanted to talk first. Again not something that was really the norm. So we sat down and he proceeded to tell me he wanted something specific and that if I could provide it he would be seeing me very regularly.

As I said he was an older man...almost 70. He wasn't from the states although he had lived here a very long time but still had his accent. Oh so nice...shiver! He wasn't bad looking. And so we sat and he proceeded to tell me that he hadn't really been able to find the type of date he wanted from anyone. Basically he didn't want to talk. He said his wife, his girlfriends over the years and the escorts he hired all wanted to talk before, during and/or after and he just wanted to come in get down to business and have fun without talking and all the emotional things women do. He said he liked noise and talking dirty during sex but he didn't want to talk before or after. He also liked it a bit rougher. I felt very comfortable with him. And after a little more conversation about what he wanted I told him that I felt I could provide him with what he needed. And then we had some fun before he left. It was pretty mild the first time. I knew he was just testing the waters as I was too.

After that though all other dates went to no talking. And so this was a typical date with him. I would be dressed in something sexy....often thigh highs, heels, and some type of lingerie. Occasionally he would ask that I greet him in just thigh highs and heels or a special type of outfit/costume (such as a school girl). He would show up and I would open the door and not say hello or anything. I just open the door and let him come in. He would take care of business - pay. And then he would undress and put a condom on - all without saying anything to me. After he was done he would come to me, grab me and kiss me...usually while pull off lingerie (at least panties or bottoms). Or push me to my knees to give him a blow job. And then it moved to sex - vaginal or anal. He was often rough he would dig his fingers into my breasts and ass. He pulled my hair. He was very forceful in how he handled me - pushing me to the bed, spreading my legs, holding my mouth to his cock and so on. Often he did spanking and of course talk dirty to me also. After he had an orgasm, he would lay there for a few minutes, then get up, clean up, get dressed and then say good bye. And that was it. I always got follow up emails from him telling me that I did great and he had a great time. And I am glad he did that as it would probably make me wonder if he had not had a good time. And that submissive part in me does like to please!

So for some randomness about him...

* Wow, wow, wow, he knew what to do sexually. I usually orgasmed with him multiple times during our appointment. Not only with sex (which is a very rare occasion that I orgasm from vaginal sex) but with just the little bit of spanking and digging his fingers into me. He combined it in just the right way to send me over always.

* He was the first uncut guy I had been with and also the largest man I had been with. He was a short man - he was maybe an inch or two shorter then I. He would get undressed, have wrinkly skin from age and then expose this big smooth uncut cock all hard and ready to go. And it just always amazed me to look at him...this little man that looked like a sweet innocent Grandpa and here just moments after he undressed he would be fucking me and making me moan with pleasure.

* He was the first older man I was with that liked to role play Daddy/girl. He liked it when I dressed as a school girl. He liked kind of role playing that I had done something bad at school and now came home to get punished. Or that I had been showing off my tits and pussy to the boys and school and he wanted me to show him how I did that. I never thought with someone just who was really a stranger - no emotional connection - I would be able to get off on doing that type of thing but I did with him. Previously all of my Daddy/little girl experiences had been with men only slightly older or slightly younger then me so this felt umm much hotter in a way for me as he was older and realistically could have had a daughter my age. And I never expected that it would turn me on in the ways it did because of my past.

* I have many fond memories of him. All his appointments left me very wet. I will also always remember him for another reason - because I was with him on 9/11 and we didn't have the tv on so I found out after. Later when I was checking out of the hotel room. It was such a good appointment. I came out so happy and excited just replaying it in my head moments after he left. It was a roleplay day with me as a school girl and him as Daddy finding out I was a bad girl at school. So I have these vivid memories because of the fun we had but coming out and knowing that while I was having all that fun - tragedy was striking the USA....well it is odd to think about. It is also one of those questions I always have to tiptoe around when people ask where I was when I found out. I wonder if he thinks of me on 9/11 like I think of him.

* Overall - our appointments were some of my favorite. He dared and it turned me on. It was the whole package of how he looked, how we didn't talk except during sex, how he fucked me, how he spanked and dug his fingers into me...it was all very hot for me and I always looked forward to our appointments.


(Thank you Fleshbot for putting this entry in the weekly roundup)