I usually spend Christmas in Florida in the house that my girlfriend, Heather, and I share. We are late going this year but tomorrow we leave for it.
My sub, Butler, and I are at a cusp in our relationship. We were in Florida all last winter where I moved him into the garage apartment at our house and introduced him, the very few times it was necessary, to our neighbors and friends, as our gardener and handyman. I present myself as a single woman living with Heather. There is a significant age difference between my sub and me. In that small coastal town, no one ever discovered or even suspected that he has been my life partner for the last 15 years.

He retired with a good pension. I like him busy so I found him work as a waiter at my tennis club during the day and as a server for a catering company in the evening. Together, he works about 40 hours a week. Of course, he turned over his small checks to me. The rest of his time he spent doing outdoor tasks such as gardening, grocery shopping and running errands.. We never allow him in house.

Last year he was often in a setting where he was a low wage older man who served while I was at lunch or at a party. He admitted it was the most embarrassing thing he has ever experienced as my submissive. (Embarrassing him makes him crazy for me!) Men that I dated in Florida frequently asked him to bring us drinks and in a completely innocent fashion treated him as a flunky. He was completely ignored. I could see his public service working on my sub’s view of himself. He started to internalize his place as a mere servant. This excited me to no end.

My female friends in Florida who noticed him working in the yard or as a waiter looked through him as if he didn’t exist. All they knew was that he worked for Heather and me as our gardener and handyman.. My friends there are mostly my age and they naturally wouldn’t be romantically interested in a man 20 years older than them who obviously was broke enough to be required to still be a food server. It took a lot of strategic planing and work but I socially demoted him. It may have been the most wicked thing I have ever done to him. He once was a successful lawyer. I made him into a low wage server. The whole experience turned me on incredibly.

Now, I simply don’t know what to do. Do I continue where we live most of the year as a couple in society or do I permanently move to Florida where he can continue to serve publicly as a mere servant? Right now we are only spending 25% of our time in Florida.

I can sense big changes coming. I think his chastity and cuckolding along with the steady physical discipline I have given him has helped make all of this possible. He never could have done this when we started. However, now we are fifteen years into his submission. We are both different people. He is ready to follow me anywhere as long as he can stay by my side. I finally have what I have always wanted, choice.

It sounds like we are moving farther apart but the whole thing has been tremendously exciting for both of us. However, be careful what you wish for. You may get it.

Last year, and I’m sure this year as well, we will continue to maintain his discipline sessions on Wednesday and Saturday. We’ve been doing this so long I feel we’d be lost without it. We have a tall privacy fence. I rarely allow him in the house so we do it in the backyard. Heather has taken an interest in these sessions and she usually watches and frequently asks to wield the crop. She is trustworthy so I allow her this pleasure.

I continue to control his orgasms. In Memphis we enjoy coitus once in a while but not in Florida while I’m living with Heather. She hates that he might orgasm inside of me. Instead, I allow him to fist himself off each Saturday if he has served well. Once in a while I arrange for him to fail.. When he does he is denied and he has to spend the following week in chastity.

Our most exciting times is when I maneuver us all into a social situation where he is a lowly server and I am enjoying myself with my social peers. I wanted to start Butler off right at his job by bringing a date to our Tennis club so he could wait on us. However, I’m at an age where most men my age are married or worthless. I don’t like to admit it but in Florida, I have trouble getting dates!

I did do one thing for Butler that might amuse you. I invited two women to lunch at the club for lunch today who I know are in the same boat as I am concerning available men. *Butler waited on us as we commiserated about the dearth of available men. The club was slow. I noticed Butler hovering politely just within earshot busying himself with clearing another table. I encouraged the women to describe the kind of man for whom they were looking. Both of these women are attractive and about my age. They both described men who were also about their own age who had professional jobs or money. I agreed with their idea of the perfect man.

They both knew Butler worked for me as a gardener and handyman. I couldn’t help bringing him into the discussion. I motion him over and spoke to him directly, “I guess you’re been hearing us complain about the lack of men. I know you’re been working the party circuit as a food server. Have you met any younger attractive professional men you can suggest?”

There it was. Here were three good looking women who were literally looking through him. He had become invisible. He was too old and obviously, with his job as a waiter, in another social class. I could see him wither in front of us. Oh, i knew what it was doing to him. I had subtly but powerfully belittled him. I knew he would start feeling uncomfortable in his cage before he could walk back to the kitchen.

I have learned over the years what moves him. I had orchestrated the moment for both of us. Despite himself, I knew he was excited by the emotional knife I had just pierced him with. Once the blade is in, it’s important to twist it. In those moments I can feel an electrical current pass between us. We still love each other. This situation lasts for two months each year. I can tell it moves us forward into our two different roles.