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My story contains both text messages and emails. Whenever an email is being read I have put it in italics to make it easier to distinguish. I hope you enjoy the story.

I would also like to thank and acknowledge Ramjet86 for the great edit work.


We had been together for 12 years, married for 9. She knew about my submissive desires, and most, if not all, the kinks I was into. She wasn’t interested in any of it. Other than that, we got along great and were very compatible. To her credit she never had any issue when I indulged in my kinky pleasures. It just didn’t do anything for her so she never participated. Occasionally she would acknowledge my kinks by ordering me something online as a surprise gift or we’d be out shopping and she’d ask if I wanted to buy myself some new panties. Nothing extended into the bedroom and most of the time I indulged when she was out of the house or away on a trip. About the only time she was aware that I had been playing was when I would put on one of my chastity cages because I would unusually still be wearing it at bedtime. Even then, she would simply ignore it. While she wouldn’t tease me about it, which I would have loved, she didn’t tell me to take it off either. I was content to play by myself, in my own mind. I wanted more, but knew better than to force the issue with her.

All this left my submissive desires and kinks as fantasies that I played out in my own mind. I thought that would be my life until a business trip halfway across the country changed everything. Once or twice a year the company I worked for would have large in-person meetings that could have easily been done virtually given today’s technology. The President, and most of the Board, were older gentlemen who preferred face-to-face interactions instead of seeing people on a computer screen. I actually didn’t mind making the trips since it allowed me to catch up with some colleagues, share a few drinks and let off some steam together.

I arrived at my destination Sunday evening and got settled in. I unpacked some things and sent a quick text to let her know I had arrived safely.

She responded back and added, “Check your email.”

I assumed she had forwarded something she wanted me to see. Not really wanting to be bothered I asked her what it was about.

She simply replied, “Check your email.”

I figured it could wait so I made contact with two of the guys and went to meet them in the lobby. We went to get a bite to eat and have a few drinks. A few blocks away we found an inviting restaurant and went in.

About an hour later as we were finishing our meal and starting our third round of drinks, my phone beeped. It was her and the text message read “I’m waiting.”

I responded with a question mark.

Her response was, “Read the email NOW.”

I quickly opened my email and there it was. An email with the subject line, SISSY. Looking up from my phone to make sure nobody could see, I opened the email. Thinking better of it, I excused myself to go to the bathroom. In the safety of a bathroom stall I opened the email and began reading it.

Sissy, I have been doing some thinking.

Generally, when she makes this comment it means she has decided on something, and while she will listen to whatever I have to say on the subject, she has already made up her mind to do whatever it is. With this thought in mind, I continued to read the email.

I have decided to indulge some of your kinks and fantasies. In order for this to happen it must be enjoyable for me as well. This will not be a 24/7 thing. In fact it may be only this one time. I will decide that at a later date. If you would like me to be your Mistress, this week while you are on your trip you will become my sissy husband and follow these instructions. In the side pocket of your suitcase you will find a pair of your panties. Put them on and text me a picture. If you do not want to do this, reply to this email with a simple “NO” and we will forget the whole thing. I expect a response within the hour.

She had signed the email with a single word, “Mistress”.

No wonder I had received her text expressing her impatience. This was a dream come true and I’d already screwed up. My bag was back in my room, and was only a short walk away, but a full night with my colleagues was still ahead of me. The first night at these meetings always played out the same way drinking late into the night and catching up on each other’s lives.

While the conversation flowed I was distracted with my own thoughts, wondering how and when she had put panties in my bag, how long ago had she started planning all this and what she actually had planned. My wife was someone who planned everything out to the finest detail so whatever she had planned I knew she had already anticipated each surprise. Her initial email had arrived out of the blue and shared none of the planned details other than it would involve my kinks and fantasies. That left an bahis şirketleri endless amount of possibilities. With all these thoughts racing through my head I knew the only way to find out what lay ahead was to send her the picture she requested.

Finally the guys were ready to go back to the hotel and resume drinking there. I told them I needed to get something from my room and would meet them at the hotel bar. As I entered my room I checked the time and saw I had about five minutes to send the requested picture. I frantically searched my bag and found the panties. They were powder blue with white lacy trim and ruffles that she had bought for me about a year ago. They were not a completely feminine pair of panties but still screamed sissy. I wondered if this meant she had been planning this since the moment she had bought the panties but had no time to contemplate this. I dropped my pants and pulled them on. I quickly snapped an unflattering selfie, with my shirt on and my pants around my ankles. It wasn’t a great picture but would have to do as I sent it to her with less than a minute to spare.

She responded almost immediately, “That is not the picture I was expecting. Are you sure you want to do this?”

I responded, “Yes, please.”

She responded, “Surely, you mean ‘Yes please, Mistress’. Not off to a very good start. There will be consequences. We will discuss later. Check your email.”

I looked and there was a new email waiting for me. Clearly she had prepared the email in advance as there was no way she could type that fast. Thoughts again swirled in my head wondering how long had she had been preparing for this day. I opened the email and started reading.


I am so glad you said yes, although who are we kidding, I would have been shocked if you had declined. Before we begin, know that I will be doing and saying things for our mutual kinky enjoyment. Some things will be made up stories and some will be real. You will not know which is which. Hopefully it will add to the excitement for both of us. No matter what, know that I love you and would never do anything to harm you. Also know that I intend to enjoy myself and that means I will be getting sexual satisfaction on my terms and you will have no say in the matter.

I read that last line twice. Did that mean she intended to be fucking someone other than me? I continued reading.

Let us begin. Here are the rules.

1. I reserve the right to make up any rule at any time.

2. You will obey me at all times.

3. Starting now, you may not touch MY cock.

That she called it her cock and not mine excited me as continued reading.

4. Starting now, therefore, you may not masturbate and certainly may not cum.

5. You may send me two texts a day. One greeting in the morning and one good night in the evening. You may reply to my texts only if I give you permission.

6. You may not email me. You may reply to my emails only if I give you permission or instructions to do so.

7. If I send you an email that requires a response, I expect that response within 1 hour from when I send it.

8. You may not call me. If I call, you will answer immediately.

9. You may not ask questions unless I give you permission.

10. You may not ask for permission to ask a question.

11. You may not complain.

12. You will address me as Mistress at all times.

13. You will refer to yourself as my sissy husband.

14. While you are away, you will wear your panties to bed every night. I expect you to keep them clean and for them to be clean when you return home. This means hand washing them each morning.

15. I am free to do whatever I desire. You will have no say in these matters.

If you understand and agree to these rules, send me a text with a picture that won’t disappoint me.

These rules will be in place until we are both home together. I will be keeping track of your obedient completion of tasks and your disobedient infractions. When we are back home together we will sit down and discuss this adventure and what the future will hold for us.

If at any time you decide you want to end this, text a picture of your sissy panties in a trash can with the word “stop”. But know if you do, this will never happen again.

Your Loving Mistress

I read the email several times, especially rules 9, 11 and 15. No questions. No complaining. No say in what she does while I’m gone. She had never given any indication that she was interested in any other men, but this was basically giving her a hall pass and she did say she intended to get sexual satisfaction. I trusted her, of course, but she also knew me and knew my kinks. How far would she go and how far could she go. I had on occasion fantasized about cuckoldry, but not all fantasies should become reality. This was one of them and I didn’t know if I could handle it. Then there was rule 3. She had never referred to it as her cock. The thought of that excited me bahis firmaları as it meant she was in a dominating mood. Something I had rarely ever seen and loved it each time it had occurred. I made up my mind and was ready to be her sissy husband and all that it entailed. I stripped completely except for the panties. I took several pictures, looked them over, picked one and sent it to her.

Less than a minute later she responded, “Good sissy.”

Another text arrived almost immediately. It was a picture of her pussy with the caption, “This is no longer available to you. It is only for those I decide should have access to it and that is not you. You are a sissy, my sissy and sissies don’t deserve pussy. Take a final look at what you will no longer have and will no longer be allowed to gaze upon then delete this photo. You will reply to this text when you have followed my instructions.”

Surely this was part of the game we were playing. She was feeding into my fantasies. I wouldn’t be forever denied and surely she wouldn’t actually sleep with anyone else, would she? I wanted to keep the picture but knew if I did I would somehow get caught and in that moment I wanted to do nothing other than to please and obey her, so I deleted it and sent her a text telling her it had been done.

Her response floored me and also excited me. It read, “In the future, if you want to see a pussy, look in the mirror. Mine is reserved for real men.” It was followed by the emoji of the smiley face laughing and crying at the same time. Then she said good night.

Since it was allowed I said good night to her as well and went down to the bar.

After two more hours of drinking and conversation we all decided it was time to get some sleep and prepare for tomorrow’s meetings. Back in my room I prepared for bed in my blue sissy panties with an erection I so desperately wanted to touch. I remained obedient and finally drifted off to sleep while different scenarios danced through my head.

The next morning I woke early, horny and happy about yesterday’s events. I showered, shaved and got myself dressed. I washed my panties in the sink and hung them on the shower curtain rod to dry. As I was leaving the room it occurred to me that my panties would be seen by the people who clean the rooms. I contemplated putting the do not disturb sign on the doorknob. Then I decided to leave it as is. Figuring the cleaning people probably see that kind of stuff all the time and probably don’t even think twice about it. I went to our first meeting of the day, aroused with the thoughts of cleaning ladies examining my panties and laughing amongst themselves about me and wondering if my beautiful Mistress had this in mind when she ordered me to wash them daily. The first meeting started at 8 but my thoughts drifted to contemplate what she had in store for me today.

I waited until about 9am and sent her a good morning text. It was about 30 minutes later when she sent a text in response. The delay in her response was not alarming as I knew she most likely was busy at work. At about 10am I remembered to check my email and saw that she had sent an email at 9:05am. She must have waited until I sent my good morning text to send the email. Panic filled my mind as I quickly opened it and scrolled to the bottom to see if a response was required. I did not see any indication and blew a sigh of relief. Given the time I surely would have missed my one hour deadline and she was keeping score, whatever that may incur. I returned to the top and began reading.

My Sissy Husband,

Just a quick note to let you know what your Mistress will be doing today and give you a few assignments. I have taken the week off so I am free to have my fun. I may or may not choose to keep you informed. I likely will though because it will be fun to tease you with my exploits. Joan and I were talking and she has a date with a guy she met online.

This meant she was not at work so why did she take so long to send a text in response to my good morning text. My head was spinning already. This was already exciting, fun and nerve wracking. I was aroused and wanted to touch myself. But I remembered rule

Joan was her best friend. They had known each other even before we met. She had divorced her ass of a husband about 10 years ago and had been through a lot of boyfriends since then. She was a nice, attractive lady and I always liked her but she had horrible luck when it came to men. They never seemed to work out. I continued to read the email.

She asked me to go with her as sort of a chaperone. She said her date agreed and has a single friend available so I will be going to dinner with them and wherever afterwards. I figure if it makes Joan more comfortable what harm could it be. It will be nice to get out and maybe let my hair down a little and have some fun. Who knows my date might just be the type of real man I need to give my pussy the attention it deserves.

A date? What had she told kaçak bahis siteleri Joan? Was she just feeding into my fantasies or was this real? Why would Joan want a chaperone and why would my wife agree? Everything seemed far-fetched and almost so unbelievable it had to be true. She was playing with my head again and I loved it. I was excited and apprehensive all at the same time. Was she seriously considering sleeping with another man? All these thoughts were racing in my mind as I returned to the email.

As for you, my sissy, you have an assignment. Before this evening’s text, you are to buy yourself a new pair of panties. They are to be a shade of pink or red. Your choice but they should please me. You will include a picture with your evening text.

Your Loving Mistress

I had difficulty concentrating the rest of the day. Scenario after scenario played out in my mind. Her at a bar, chatting with a handsome man. Her flirting, touching, being touched. I had a constant hardon thinking about the possibilities.

As usually happens at these functions we finished relatively early in the day. Around 2:30 I made an excuse to the guys and said I’d catch up to them around dinner time and set out on my task.

There were a lot of shops in the area and I found one that seemed to have what I was looking for and walked in. Immediately I was greeted by a sales lady who asked if I needed any assistance. This was awkward and a bit humiliating. I’m sure I was blushing when I said I was just browsing. She was a few years younger than me. Okay, more like 10 or 15 years younger and was tall, slim and attractive.

She said, “Okay, let me know if I can be of assistance. Women’s sizes can be a bit tricky and I’m happy to help.”

I began to get excited and a little uncomfortable. Did she know I was looking for something for myself? I told myself she couldn’t possibly know. I’m sure she was thinking that most men just have no clue about women’s sizes. My head was swimming. My mind was playing tricks on itself and my wife, back home, was responsible and I loved it. I wanted to talk to her and tell her everything that was happening and how I was feeling, but I remembered the rules. No contact without permission.

As I browsed through the area where the bras and panties were located I could feel eyes upon me. I looked around but saw nobody. Finally I saw them. Bright red. They had a lace waistband and a small black bow on the front. I picked them up and held them out in front of me. Seemingly out of nowhere the young sales lady appeared at my side.

“Those are cute,” she said. “For that special someone.”

Again I’m sure I blushed.

She tried to put me at ease, “Don’t be embarrassed. We get a lot of men looking to pick up an intimate gift for their lady friend or wife.”

I tried to speak but what came out was a stammering, mumbling mess that didn’t make any sense. She took my hand that was holding the panties and asked if I had any idea about her size or what style she normally wore. I struggled with an answer. How could I come close to my size without just coming out and saying they were for me. The excitement I was feeling was overwhelming. I tried to take a deep breath but it didn’t seem to help. Finally she let me off the hook, if only for a moment and asked for the panties I was holding. I relinquished my grip on them and our hands parted. She put her index fingers in the waistband and held them up.

“If she’s about my size, these may be good.”

Then she put them along her own waist, modeling them. I was painfully aware of the erection in my pants and hoped she didn’t notice.

“Is she my size? Or is she smaller?” She seemed to hesitate before asking “or bigger?”

Seizing the opportunity, I sheepishly said bigger.

“Well depending on how big we’ll want to go up a few sizes.”

She picked up another of the same pair and held them up against the first pair.

“See how these are the same style but provide a little more room.”

They were clearly a few sizes bigger and looked like they would indeed fit me better. I made a comment about how they looked more similar in size to what she had, compared to the first pair. The reality was the first pair would have fit her perfectly. I did indeed know her size and they were it.

The sales lady said, “Well we have to be sure. Panties are an item you won’t be able to return. You understand, I’m sure.”

I hesitated for a second, then said I would take them and take my chances.

She said, “Great, now what can we get to go with these. A matching bra, perhaps.”

Again, I couldn’t think of what to say. She was doing her job, pressing a sale, and doing it very well. I managed to put her off and said I’d just take the panties. She relented and walked me over to the register. She rang me up, put them in a bag and off I went.

Before I reached the door she called out to me and said if I change my mind about the bra or anything else I might be interested in to come back any time. A few ladies who were in the store looked up to see who she was talking to. I could feel my face turning red and my election getting harder (as if that were possible) as I went out the door.

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