Toronto, On Business

I was finally about to met her. We met three months before on internet. She lived just outside of Toronto, a city where I was travelling often on business and our discussions rapidly turned to sex. She seemed very open and kinky and was definitely looking for a regular lover. On my side I had been with the same woman for over 20 years and had a plain vanilla sex life when I had a sex life.

So I was finally making it for a full week in Toronto and she asked me to drive to her place and to be there for 6 O’clock as she would be waiting for me. My idea was to take her out to dinner and enjoy a great meal together, and to take it from there.

She sent me a few pictures before and she looked like a very healthy and good looking woman. I mostly remembered her great smile and eyes, not to say her kinky look.

Every time we chatted, she was telling me that I was turning her on and leaving her frustrated with no one to help, and that one day I would pay for this. I was having fun and making sure I would always tell her how long I would perform oral sex on her, as I knew she missed it so much, as oral sex was her favourite sexual activity.

As I got closer to her place I stopped to buy a nice bottle of wine and some flowers for her. I finally arrived at her place and I was excited. She lived in a very large cottage, that looked very clean and very well maintained.

I parked the car and walk to the front door and rang the bell. While I was waiting for her to come and open the door, I noticed a small note on the floor:

“michel, I had to take my son to my mother’s place for the night, I will be back soon. The door is unlocked, so please get in the house, and follow the instructions you will find in the entry hall”

I looked around and decided to try the door. As she said it was unlocked so I walked in and closed the door behind me. I was in a small lobby and the other door making it to the house was locked, so I had to stay in between the two doors. I saw a sports bag on the floor with an envelope on it. My name was written on the envelope, so I took it and wrote the message:

“welcome michel

Tonight I want to make you pay for all the teasing you did to me during those months and I won’t be the one frustrated at the end of the night.

Before my arrival, I want you to undress and put whatever you will find in the sports bag and follow my instructions. You better be a nice boy and obey.

Love

Mistress.”

Wow Mistress…. I liked that but I wasn’t expecting this… but wanted to play the role. So I undressed and put my clothes in the closet. Then I opened the sports bag and found some leather restraints and a collar. There was also a thing in leather and metal, and it took me a while to understand what it was… It was a locking cock cage, that I slid over my penis and used the small lock to make sure Mistress would be happy. I also put the collar and the restraints around my ankles and my wrists. The feeling of the leather and knowing that I would be her slave got me excited, but my penis couldn’t grow much because of the metal cage….

On the bottom of the bag I saw another letter, with a key attached to it. I took it out and read it:

“Good boy, how do you like loosing control of your penis? I am sure you enjoy it….. Now you are allowed to walk in My house and You will go to the first room on your left on the second floor and follow the instructions there…. See you soon.

I walked in and her house was very clean, I took the stairs up and opened the first door on my left and saw a letter waiting for me on the bed.

michel, open the closet and find something sexy to wear for me, then you will lie on the bed and make sure your ankles and wrists are tied to the bed. I also want you to put the blindfold and the mouth gag that you will see on the table next to the bed. I can’t wait to be back. Love. Mistress.

I opened the closet and all I could see was some women clothes, so I opened a few drawers trying to find something sexy to wear, but they all had lingerie, sex toys, or were emplty.

I read the message again and couldn’t understand what she meant, but time was flying and I was afraid she would be back soon and that I wouldn’t be ready.

In the drawers were some very sexy outfit, but in dark colours and with lots of leather clothes. In the closet, everything was more feminine, with pastel and light colours.

I finally decided that I had to get ready for her, and I put on a pink outfit with a bra, a very large waist clincher and some very frilly panties that were covering my cock cage. I also had the pink stockings. I looked at myself in the mirror and couldn’t believe what I was doing, and I wanted to run away. I looked so feminine and had never experienced something that crazy.

I installed myself on the bed and started by the ankles, then I took the mouth gag. It had a penis shape that would fit in my mouth and a long dildo on the outside. It also had a lock to keep it in place. The penis was quite big but I managed to get it in then I put the blindfold and attached my wrists to the top of the bed…. I was now totally helpless and had to wait for her to arrive. I was trying to listen to the noise, but everything seemed very quiet in the house.

I don’t know how long I stayed in that position before I finally heard some noise. The door opened and a very sexy voice said:

“Hummmm look at the nice bitch in my house, waiting for me to have fun”

I felt her hands all over my body and my penis grew as hard as it was possible in my cock cage. Then I felt the penis gag in my mouth moving, as she was playing with the dildo. I understood she was lowering herself on the dildo and that was pushing the gag deeper in my mouth, forcing me to get more of the penis gag in my mouth.

Once she had the entire dildo in her, she started to rotate and get the dildo in and out of her pussy…. I could smell her and feel her juice running in my face. She was going faster and I knew she was getting more and more excited every minute. Her breath was heavier and I am sure she was enjoying it a lot.

“Ho my little slut, You look so sexy…. Do you like the cock in your mouth? I am sure you would like to have a bigger one to suck on…. You look so sexy in pink…. Are you getting wet by now? “

I couldn’t answer her, but I wasn’t totally sure if I was enjoying it…. This was just too different and new to me… but I know she was having fun and having a great time.

“Oh but I forgot to ask you to wear jewels honey…. I like it when a woman wears jewels in bed, here let me grab those for you…”

With the blindfold I couldn’t see what she was doing, but I felt her hand pushing aside my bra and I felt a pinch on my left nipple, the on the right one…. Oh that was uncomfortable.

“You look so cute with your jewels, sexy… and I made sure you won’t loose them as I adjusted them with maximum pressure…. Have you ever had nipples clamps on before???? You will enjoy the feeling when I will remove them…”

The pain was slowly disappearing as I couldn’t feel my nipples any more, and I had to concentrate on her. She was just using the dildo with so much energy that I thought she would break my neck.

After she came a few times, she got up, and left the room with saying a word to me.

I stayed on the bed, totally helpless, with an erection as big as I could get one in the cock cage. In fact my penis was so squeeze in the cage that it was starting to be painful.

After a while, she came back in the room, and I felt something cold on my penis.

“You shouldn’t try to impress me with your big “clitoris” in its metal cage… The ice will cool you off and remember…. I told you so many times that you have been such a teaser on the internet… Now you are mine to play with. The ice on my balls and my penis made me loose my erection rapidly. She then removed the gag and replaced it with her pussy. Again she used my mouth for a long time, until she reached another orgasm.

When she got up, I asked her: “Mistress could you please remove the clamps on my nipples?”

“Oh poor sissy, I am sorry I forgot about them, it is a got thing you made me remember”

And she took the out. I wasn’t expecting such a pain and I let out a long noise.

“Poor girl, that hurts…… well I don’t like hearing those noise in my house, What if the neighbours hear you? “

And as she was saying it, she pushed the penis gag back in my mouth…. “suck on this instead of complaining”

She then took a spreader bar with restraints and attached those to my knees, so my legs were wide open. She detached my wrists and attached them to the middle of the spreader bar. Once really secure in that position, she detached my ankles and pushed me and lifted me so I would be on my knees. Having my hands pulled to the spreader bar, I had to rest on my head, which was turned on the side because of the dildo still attached to my mouth gag. It was very uncomfortable position and I really couldn’t move by an inch.

Mistress then lowered my panties and gave me a spanking. Each stroke was painful and since I couldn’t move it was impossible for me to try to avoid the shock. She wasn’t a sadist but just wanted to see my buns red, as she said red and pink go well together.

Then I felt something being tied around my balls and then my balls being pulled. What she did was to have a parachute ball stretcher attached around my balls and then pulled it to the spreader bar. I was now totally helpless, with my ass up in the air, and very accessible to her.

Then I felt her pour something on my ass, and rub it, slowly she rubbed my ass, and suddenly pushed a finger in my ass hole. I never had anyone do this to me before except a doctor…. The sensation was funny at first and I rapidly relaxed and it became enjoyable, until she inserted a second finger. She was also pushing deeper and deeper and faster and faster…. My ass was getting to be on fire, when she pulled her fingers out. She then pushed a butt plug in me. Soon I found out it could be inflated and was also vibrating.

She adjusted the size to what seemed very large and the speed to very fast and left me there alone in the room.

When she came back in the room, I was exhausted, and she pulled the butt plug….. I felt so empty.

“I see my little slut likes to have something in her pussy…. You really are quite something, a cock in your mouth all the time…. You are a real whore….”

She got behind me and put her hands on my butt and got closer to me.

“since you like cocks so much, I have a nice one for you now… It is a big one, but a slut like you should be very happy…”

I then felt her pushing something in me, and I soon realized she was about to fuck me with a strap on dildo. And it felt so big. I was just trying to relax, but the position I was in wasn’t the best one to relax….but the fingers and the butt plug had helped me prepare for the dildo and soon she was fully in me. She started slowly but soon was going very rapidly, and the feeling on my prostate was getting me totally excited, I had never been so excited in my life.

“See my sissy, fucking you will make you so wet, your prostate will start leaking very rapidly and you will cum and cum and cum, but I want to collect each drop for you.

She fucked me for a long time, I was so tired I was about to faint, I never had been so exhausted before.

When she had enough, she removed the spreader bar and let me lie on the bed, on my back, she took out my gag and pour all my cum she had collected in my mouth…

“She you are now a real girl, you have suck a cock, were fucked and had some cum…. And you wear nice lingerie and enjoy being sexy……”

She removed the blindfold and this was the first time I was seeing her, and she looked even nicer and sexier than on the pictures she sent me by emails.

She lowered her head and kissed my penis, and asked me :

“Do you want me to remove the cock cage and undress you for the night or are you ready to sleep like you are right now? Think about it well before you answer?

“Yes Mistress, please remove it, and let me undress, as I really want to take a shower before I go to bed for the night…”

“well I asked you to think well before, and you didn’t think at all, I don’t want to know about you, I wanted you to think about me, and see what would please me more…. And of course, I want you to keep your cock cage all night long and wear you sexy lingerie also…. But since you want a shower, I will allow you one….

She took me by the collar and pulled me in the bath room, and made me sit in the bath, the she got up and let herself go on me. This was the first golden shower I ever received…. I felt so ashamed and humiliated but I didn’t want to say a word.

When she was finished, she allowed me a real shower, but only with cold water, and once finished she took me back to the room, and she choose a new outfit for me to wear, all in white, stockings, frilly panties, garter belt and bra.

“You look like a virgin in white, good thing I know you no longer are….” And she started laughing….

She took me to bed and tied my hands to the bedpost and left me in that position for the night……

I felt asleep thinking about how she would wake me up the next morning…..and I couldn’t wait to find out.