Jessica in Red Ch. 01

He was right. The heart emojis might seem trivial, but the fact that they were aimed at Patrick made my heart sink.

"Ok, let's get you set up, because I need to go handle a few preparations for your wife's big night."

He reached into the box and removed a small box. The photo on the box clearly showed what it was. It was a chastity device. He didn't speak, he just took his time unpacking it, including a small lock, which he turned the key on a few times to be sure it opened and closed.

"Step one: Jimmy-boy's useless little dick gets locked away. I mean the guys who are going to use you tonight certainly don't want that little thing flapping around. And we both know Jessica is going to have no use for it after tonight. And last, but certainly not least, you are not going to get to pleasure yourself for quite a long while. So, let's get you all locked up and taken care of."

He handed me the two part cage. "Put it on, I am not doing it for you."

Once again, there was no use pushing back. I looked at the photo on the box and after a couple false starts, I got myself inserted. I had fantasied about a chastity device before and thought is arousing. But the reality of getting placed in one isn't arousing at all. It is humiliating, and in this case, humiliation and arousal are not connected. My dick shrunk to little boy size as I got organized to put it on, and even after two misfires, my dick stayed shriveled enough that it was in the smallest possible setting. I finished it and looked up at him.

"You really look like a little boy. I could have just put you in this and sent Jessica a photo and she would have driven herself to my place, but what fun would that have been!"

He wasn't wrong. I looked pathetic. He showed me the lock.

"Put it on. And hand me the key. Tomorrow I am going to give the key to Jessica. I will act in an advisory role, but it will be up to her when you first get out of that. But do recognize, I can be very persuasive, and I think a month is a good first run." Patrick laughed as I handed him the key.

"Now, this is kinda late notice, but you know sometimes timetables have to get moved up." As he said this, he pulled out a butt plug from the box. He also pulled out a harness like device that I could only assume was designed to hold the plug in. I was speechless as I stood naked and contemplated what he intended to do next.

"I always preach that we need to be customer centric, and so, even though I would like to be the one to pop your anal cherry, oh, Jessica spilled the beans that anal was not part of your relationship, so I am just guessing you are an anal virgin. By the way, she shared that little nugget when we were texting this morning. I would guess she was masturbating while texting with me, because she seemed to lose control of her edit button. But I digress. Back to our customers tonight. I offered your ass and they are very excited to take it. In fact, they were so excited they signed a contract extension just on the promise of your ass. So, I guess both you and your wife have great asses!"

He was having a little bit too much fun. But what was I going to do about it? My wife was out of touch and preparing for him to make her his, I had already sucked his cock, and my dick was locked away tight. I really didn't have any leverage at all.

"But, since I am a nice guy, I am going to have you spend some time this afternoon preparing your sissy ass. Don't worry, I am not going to do anything with you, but, ah yes, right on time." As he said this, his administrative assistant, a very attractive middle aged woman named Sydney walked in his office. I was too far gone to even try to cower or cover myself. She said hello to both of us like it was just a normal day.

"Sydney my dear is going to take over and supervise your preparation. You will cooperate completely with anything she asks. Do not make come back here and take corrective action, understood?"

"Yes, Sir."

"Sydney, his appointment is at 3pm, the clinic said they will have him completely ready at 5pm, but he will need to seriously hydrate and might be a bit wobbly for the first 30 minutes. So, take him to the hotel. There is a nice suit waiting for him there. His dinner engagement is at 6:30. I want him seated and comfortable when I enter with his wife. Thanks again for rising to the occasion on such short notice."

Sydney responded like her work agenda had just been reviewed. "That sounds good. I will make sure everything goes smoothly. You just concentrate on the beautiful young lady who has no idea how lucky she is."

Sydney turned to me, "I never understood how she was with you, and to be frank, I was surprised that Patrick didn't take her at the Labor Day picnic. It turns out, he didn't see her because otherwise all of this would have happened 2 months ago. I told him that he might just want to keep an eye out for a hot little devil at the Halloween party. That will teach you to tell me that she would be wearing red!"

Both her and Patrick laughed. Patrick came over and kissed Sydney on the cheek. "Tell your husband I owe him one, he picks the course, the greens fees, drinks and dinner are on me."

She smiled and responded, "just let him win a hole or two so he has some ego left after that."

"Are you implying that I have a bad habit of crushing men's egos!" They both laughed at me given the obvious connection.

As Patrick left, he looked at me one last time. "Tonight, will be the best night of Jessica's life. Be happy you had a very small part in making it happen. I am going to truly enjoy making love to her."

With that he left me standing there naked and humiliated. My pity party was short lived. Sydney broke me out of it quickly, "For god's sake, put some clothes on, put your toys back in the box and follow me. Your clinic appointment is in 30 minutes."

I did as instructed. As I exited the building a mere 6 hours after I arrived, I marveled at how thoroughly and completely Patrick had orchestrated a seismic alteration of my life. I was off to some sort of clinic to get prepared to be an anal sissy, my wife was at a spa getting herself ready for an evening of passion unmatched in her life, and both of us were happy and excited about our new lives. Only Patrick could make that happen so efficiently and effectively. I shook my head in awe.

To be continued.