Date with a Doctor

I was nervous as I walked into my boss's office this afternoon. I had just gotten out of school and was ready to enjoy my night off when I got the call.

"Thank heavens you're here!" she exclaimed as I walked through the door. "OK Jennifer just called in and she had a date tonight with Dr. Owens, and I need you to fill in for her."

I work for an escort service. And, no, I am not a prostitute. In fact, I almost never sleep with my clients. I just love to take a man out for a good night on the town and then call it a night. I am just not aggressive when it comes to sex, most guys that hire an escort, and are looking to get laid, want a girl that is going to just hop on top and go to town. I guess I am just to shy to do that. Yeah, I could make a lot more money if I did, but I am content to keep my dignity intact and just make what I can.

Dr. Owens is well known as a regular client at the service. He is a young, attractive, and very wealthy surgeon, who is always having these dinner parties at his mansion. And he always hires a girl from the service to go with him. I guess he pays well, because the other girls love to get him for the evening. I always got the feeling thought that more goes on there than the usual get together.

"What? Me? I......I....."

"I know it's not your kind of date, but I really need you tonight. He is such an important client to the service, I couldn't stand to lose him, and you are the only girl available. Actually, he is really happy. I have showed him your pictures and he can't wait to meet you. I think you could make a lot of money if you started taking these kind of jobs more often."

"I know, it's just that no one ever talks about what goes on at his parties, and that makes me nervous."

"He is just secretive because he is a doctor and if his patients found out about his tendencies he could lose his practice."

"But what if he tries to do something I am not comfortable with? You mean I can't tell anyone? What am I supposed to do?"

"You can always leave if you don't like what is happening, but I would hope that for such an important client that you would be accommodating." She said with a stern look on her face. And I knew that I didn't really have a choice.

"OK, fine. I'll do it, But just because you really need me. Don't expect this to be a regular thing from now on."

"Great! You won't regret this, I promise. Oh, and I almost forgot. His rules are that you must be completely shaven, and you need to wear only a black dress, no bra or panties.

"Wow, now you are scaring me even more, but what can I say. What the client wants, the client gets."

"That's my girl. Now go get ready, his car will be here to pick you up in an hour."

So I went to my dressing room and did as instructed. I tried to imagine what was in store for me later and I started to get excited. Maybe this would be a good thing. Maybe I just might enjoy myself. As I shaved the naturally blond hair from my pussy, I wondered why the strange request. I figured that he probably just wanted to have a quickie in the limo and didn't want to have to fumble with panties. Then he could get back to parading me around that party and showing me off to all his friends. Somehow I started to hope that it would be more than just that. And I started to rub my pussy just thinking about it. I had to stop myself from cumming before I even get picked up. What good would that do. So I finished up and was ready to go, with my sexiest black dress and my highest black pumps. I was about ten minutes early so I went downstairs and waited by the door. Suddenly a black limo pulled up and I was shown in. As my eyes adjusted to the light I noticed Dr. Owens sitting across from me taking it all in.

"Good evening Dr. Owens. How are you doing today?

"Wow!" was all he said for a long time as the driver pulled out of the driveway and began the 15 minute drive to the mansion.

Finally he spoke again, "I have been waiting a long time for this. I have wanted to bring you to one of my gatherings for a while now, but your boss seemed to think that you were not ready for me."

"So are you going to fill me in on what the plan is for the evening?" I asked with a coy smile.

"Well let me just say that you look amazing. Did you follow all my instructions? Let me see."

So I nervously pulled up my dress just enough that he could see my pussy lips and that they were hairless and panty-less.

"All that I am going to explain to you now is that I want you to obey me completely tonight. I may ask you to do some things that you are not used to doing. But I promise that I will not harm you." He had moved over next to me to inspect closer the job that I had done. He started caressing my inner thighs, and then reached up and cupped one of my breasts and squeezed gently. "I intend to give you more pleasure than you have ever dreamed of, but you have to do everything I say. Speak only when asked a question, and always refer to me as "Sir" Is that understood?

"I think so" I said shyly, embarrassed that he was speaking to me that way.

Then out of nowhere he smacked me hard on my bare thigh. Leaving a hand print where he made contact. "Yes Sir" he said. And then I understood.

"Yes Sir" I repeated. And then the caressing started again. I felt a little dirty, but I was getting awfully turned on and I was wishing that he would just fuck me right there in the limo. But we had arrived, so he straightened out my dress and took my hand and smiled as he said, "Let's go meet my guests."

We then entered the mansion and walked into the dining room where all of his guests were already seated waiting for us to arrive so they could begin the dinner. I noticed that I was the only female in the room and I started to get nervous again. Dr. Owens led me to my seat and sat next to me and began introducing me to the men at the table. They were all wealthy business men and other doctors. They were all pretty attractive men, I started to wonder if I was going to have to service all these men. Is that why he pays so much?

My mind was put at ease through most of the dinner. We laughed and joked and told stories while we ate. I almost forgot about what had happened in the limo earlier.

Then once dinner was over and the table had been cleared. Dr. Owens took me by the arm and led me down a hall and then down a staircase into the basement. There were candles lit everywhere and there were several contraptions and devices that I did not recognize.

"Now for the fun part." He said as he slid my dress from my body and I instinctively covered my breasts. He walked a few feet away and the next thing I knew I heard a swish and felt a stinging pain on my ass. I jumped and yelled out in pain as I took my hands away from my breasts to feel the welts that were appearing on my ass cheeks. "You will not try to cover yourself at any time" he said sternly and I knew what he was expecting.

"Yes Sir" I said, not wanting to feel the whip on my sore bottom again.

Then he put a blindfold over my eyes so I could not see what he was doing. Next I felt something cold on my hands as he brought them together behind my back and cuffed them together. Then I felt another strap go around my neck and latch tightly. I started to get really scared about what was going to happen and I felt a few tears soaking into the blindfold that was covering them. I started to panic and fight against my bonds. "We were going to do this the nice way, but now I guess we will have to do it the hard way." I started hearing some footsteps in the room and I realized that the other men were joining us in the room. I was mortified to be stripped naked in front of these men that I had just met. I then felt hands on my shoulders and I was pushed down onto a bench with my legs straddled on either side and my ankles were cuffed and attached to either side so I couldn't move my legs. Something about all this was starting to get me aroused. How could I be enjoying this? I thought.

Suddenly I felt hands cupping my breasts and squeezing and playing with my nipples. I started to moan with pleasure as they were pulled on and licked and teased. I had no idea who was doing this or how many hands there were, I just decided that I was going to relax and enjoy this. I started feeling hands rubbing my legs and pulling them farther apart. Then a finger started exploring the folds of my labia. "She's dripping wet!" someone exclaimed. Slowly a finger was inserted into my vagina and started fucking my hole gently, then two fingers. I started to move my hips to try to get the finger farther inside me. "That's enough I heard Dr. Owens say, and suddenly all the hands were gone. I groaned in disgust as I wanted then to continue. Then suddenly I felt a sharp pain on my chest, as if a hundred little whips had hit there all at once. One of them grazed my nipple and I felt it harden with pain. But with that pain, came pleasure that I have never imagined before. As the blows kept coming, hitting me on both breasts and my stomach and between my legs I started leaning back and rocking back and forth as the blows started to feel good and I wanted more. Then they stopped.

"Sit up!"

"Yes Sir"

"Are you enjoying yourself my slave?"

"Yes Sir!" I moaned.

"Are you ready for more?" he asked.

"Oh, yes Sir, please. Punish me some more."

I then was lifted and guided to lean over some padded contraption and my ankle cuffs were attached to the bottom with my legs spread open. Then my hands were unattached and brought in front of me and bound underneath. My head was just hanging off the front and I could not lift myself. My ass and pussy were now on full display to the men that were watching and I felt my juices dripping down my leg. Then I started to feel the whip again on my ass. I squealed as they hurt worse then the front did. It must be a different whip this time. I lost count as my ass cheeks were reddened with blow after blow from the whip. Suddenly I felt someone in front of me and then I felt flesh against my lips. I stuck my tongue out and started to lick the cock that was presented to my mouth. I licked all around the head and started trying to pull it into my mouth but I couldn't move my head forward. Then he grabbed my hair and shoved his cock all the way to the back of my throat. I gagged and coughed as I tried to breathe. Then he released my throat and started to fuck my mouth still holding on to my hair and shoving the head of his dick deep down my throat with every thrust.

This assault on my mouth had made me forget about the whip that had stopped at some point and now there were hands again caressing the grooves and marks that the whip had left behind. Then I felt hands rubbing my clit and spreading my juices around. Every thrust from the rod ramming my throat pushed me harder onto the fingers exploring my holes. I started feeling fingers rubbing around my little asshole as well. This made me nervous because I had never put anything in there before and these fingers felt like they meant to start invading. Sure enough, there was some pressure there and then it gave way to a finger that started going in and out and I moaned around the cock in my mouth as I felt a new kind of pleasure. The fingers were moving in and out of both of my holes and I started trying to move back further onto them but I just couldn't move enough to make a difference.

All of a sudden everything stopped and I cried out in agony as I was really enjoying myself. Then I heard Dr. Owens voice. "Do you want more?

"Yes Sir!" I yelled

"Tell me what you want"

"I want to be filled up. I want all my holes filled. I want to cum."

Finally I was set free and led, by a leash attached to my collar, to a cot of some sort where there was a man laying there. I climbed on top of him and lowered my pussy over his erection. My hands were still bound in front of me so he guided his dick into my hole. I almost came from the feeling of fullness. This had to be the biggest cock that I had ever had inside me. I started to lift myself up and down and rode his cock like a mad woman. Then I felt a man behind me push me face down onto the other mans chest and while the man under me was thrusting up into me I felt fingers again at my ass. The finger went in again and I got nervous, as I had never had a dick in my ass, much less at the same time as I was being fucked. I took a big breath as I felt the head of a large cock rubbing the entrance to my backdoor and it started pushing its way in. I yelled out as the head was sucked in, he kept it there for a few seconds. Then almost pulling it all the way out, he thrusted it in harder and got another inch in, as I screamed again. He pulled out slowly, and then he buried his whole cock inside my bowels. I almost passed out from the full feeling I got having both holes stretched to their fullest. Other hands started groping at my clit and my nipples until I just couldn't take anymore and I came in a screaming orgasm like none I had ever felt before. The men did not even take notice, except to shove another cock in my mouth. This continued for a while, until I thought I could take no more. Finally I started to feel warm juices being squirted into me at all ends. My face was covered and I felt cum splattering on my shoulders and my hair and back as I realized that all the men must have been jerking off around me watching me get fucked in all my holes.

They all got up and left me lying there, still blindfolded, and wondering if what just happened had only been a dream. When, at last, the blindfold was removed from my face, all I saw was Dr. Owens sitting next to me smiling. I smiled back, with cum dripping from my face. He handed me a towel to clean up with and watched as I rubbed my breasts and back, and legs and stomach, until I had cleaned all the cum from my body.

"So, did you have fun?" He asked.

"Surprisingly, I did. Where you fucking me?" I asked, suddenly not sure if he had been involved at all in what had just happened. He just grinned and said "I Guess you'll never know."

From that night on, whenever Dr. Owens was having a party I always volunteered.