The Trophy Wife Ch. 01

Things were a blur after that until I was driving home. I had to have been there for more than three hours. I have not been the same since, and I am sure dear readers you understand. This was the beginning of what was to be a unique tryst but now I am different. It was the first time she urethral sounded me. I hope you understand that this is raw in me even today.

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A week later she came to my office again and we went to lunch at the little French restaurant. In so many words again she asked me if I was ready for new things? I was not thinking with my mind, but I said sure, adjusting my pants, getting a little stiff.

She had them bring a phone to the table and told me to call my secretary and tell her I would be taking the rest of the day off. Then she said that we were going shopping. Hmmm?

The ride in her Jag was more than scary. Damn she drove fast. She did not say where we were going until we got to the adult toy store. I had been there before to purchase books. She took me to the upper-level fetish area and purchased two blow-up items: A blow-up butt plug and a blow-up strap on. They were made of quality latex rubber, and had a bulb connected to them which would blow them up larger. She also purchased a package of extra-large condoms.

You can imagine where my head was at this point. I am not sure what else we did but we went back to her house. She dismissed the maid who gave me a very strange look, I don't know why I remember things like that. Perhaps I felt guilty. I am sure she knew what was up.

The sessions from here on out always began with a discussion on the veranda, of what she needed, perhaps what she was going to do, and a walk to the room. After a bit she joined me on the veranda. She had changed into her almost see-through sheer sun dress. The semitransparent dress accentuated her beauty. I could tell her nipples were hard.

She informed me the uses of each toy. The blow-up butt plug was to loosen or open the sphincter muscles of my anus so as to allow the strap on to slide up my butt. The strap on would rub her clit as she fucked me. And, with all that, we walked into the room.

I was placed over the horse. She had an enema unit in her hand. It was connected to something. She lubed my anus up and stuck it in. I felt a little bit of discomfort but it was not that bad. Then the flow was interesting! As more of the water/liquid began to flow, I was thinking about my safe word. Then she started rubbing my balls and penis, saying, "Deep breaths Bobby."

It began to feel interesting, almost pleasurable, until the first cramp hit, and she pulled hard on my balls and penis. I was like a washcloth and went limp.

She sent me off to the bathroom saying, "We need to clean you out and dilate your sphincter so we can have fun."

She didn't seem to mind the gross nature of giving me the enema. Yes, it was erotic, but I was not hard anymore. After relieving myself in the bathroom, I cleaned up.

Then to my surprise, I was back on the horse, belly down. She lubed up my butt and inserted the new blowup butt plug with a rubber on it. She pumped it up two or three times. I remember hearing something like, "Bear down, Bobby, and it will come out." Slowly she pulled it out with a plop. Holy cow, that was different coming out, but felt good. This was not liked the other sessions I had liked. This was something more... I was uncertain.

She said we were cooling down too much; we needed to get hot again. Some paddling and rubbing, the chemistry began for me, deep breaths, and stiffness. I suddenly had a cold feeling as she added more lube up my anus and reinserted the blowup butt plug again. Deflated, it went in without much trouble. And she counted to four as she pumped it up four times.

Oh, I felt full. Then she pulled it out slowly without deflating it. She was telling me that can cause the sphincter to lock up if I did not push down. She fingered my ass, and I felt a deflated plug inserted again, then she counted to five. Oh, gee, that was good yet full. Then a pop, it came out after she pulled it.

Then she was able to put three, and then four fingers in my ass saying, "You are dilated enough. We will try fisting another time."

She took me over to the bed and had me lay on my back with my butt on the edge of the bed. It was at her crotch height. She wanted me to watch as she hooked up the inflatable dildo to her harness. She put a condom on it and noted that would make it a sterile toy and easy to insert. She then pumped it up as I watched and then deflated it, saying, "Bobby how much can you take?"

"Oh, this is so much fun," she said.

In the past I had liked anal stuff, but I was not sure about the pump-up strap on thing...

Deflated it went in without a problem, and then she pumped it one time. Oh wow, that was different and felt good. I was on my back. She was between my legs, standing and pumping it in and out, and then she started slapping my penis. I remember thinking, why she can't just jerk me off? The harness she had the dido in was rubbing her clit.

"Bobby do not come yet; we are going to do this together." It did take her a while. I sagged and then got hard again, she slapped and then rubbed. Now she was pushing it all the way in and rubbing up and down and pulling it almost out.

"Let's see if you can take two pumps moving in and out." Phew, that thing got big. I was taking deep breaths. "Good," she said, and pumped it one more time. She was quivering and had a small orgasm. She began going in and out and up and down with more vigor. It was as if my ass had the same pleasurable nerves that my penis had.

It felt really good now and then. She then had the big orgasm, she stopped and just quivered. I'm thinking what about me, I want to come too! She pulled it out and leaned down. She gave me a wonderful blow job to finish which took a bit longer and then kissed me for the first time with my cum in her mouth, saying: "I imprint you." I did not understand, but I felt great and would at this point do anything she wanted to do.

After a bit, I was told to take a shower and get dressed, and then meet her on the veranda. When I got out to the veranda, she was drinking a cocktail of some sort and had a bourbon and water for me. How did she know that my favorite was bourbon and water? Always, so many unanswered questions. We enjoyed some light conversation that I don't remember much of except she seemed happy.

She told me I did good this session and that she would be gone for several weeks. She did not get up, did not give me a hug, and just said, "I'll see you when I get back."

I was dismissed.

Chapter two next...