A Gender Retirement

By BethanyDaWade

A little story about dreams and reality that I wrote and submitted for the May contest, a little mayday at the end is it's only qualification, but I hope you like it.

-Prologue-

My name is William, I am a fifty-eight year old father of four, who has worked hard to raise, and provide for his family for forty years. I am also a transgendered individual, and despite having successfully lived all of my life in a male role, have never been comfortable in it. When I was young, I had come from a time in which about the only gender issue that was recognized by the general society was transvestism. It was largely defined as men who used cross-dressing as a fetish tool for sexual stimulation and gratification. There was no real talk outside of the medical community about transsexuals, and no admission at all of anything between these two extremes at all.

To say I didn't have any idea why I felt as I did earlier in life would be charitable. My confusion became less in time as the phenomena of transgendered became better understood and more publicly discussed in our society. However, any medical treatments to help me obtain an outward appearance that would better match my inner self came way to late for me to take advantage of earlier in my life, and later, my responsibilities and relationships had a momentum that made trying to do anything along those lines unthinkable.

I have no regrets really, I needed family and children in my life more than I needed anything else, and the discomfort and pain I always had due to my transgendered nature was worth bearing in order to achieve those things. I firmly believe that even now, I would have not been able, in this society, to have had a reasonable chance to achieve what I have if I had pursued life actively as a transgendered individual. The chances for employment, relaxed and socially peaceful lifestyle to raise children, and long term familial relationships for the actively transgendered are still not really obtainable for the average person in our society.

My wife always knew about my situation, she was my spouse from my second marriage and after the disaster of my first, I was up front and honest with her from the start. I loved her, and she trusted me to live up to my part of our marriage and be a provider and father to our children, so while she didn't have to deal with the stresses of my gender disphoria, she was aware of it, and how unhappy it made me.

The greatest test of our love and commitment had come, the kids were grown and had moved out, I had earned and saved enough for me to retire early. The reasons I had avoided expressing feminine self were gone, and the urge to do so was overwhelming. It may not have been fair to her after all these years, but it seemed that the time had come for her to find a way to deal with it, or our marriage of twenty-five years was doomed. I did not want it to be, but I felt such a clamor within to give in to my desire to become more feminine, that I couldn't resist it. The triple controls of responsibility and being a normal father figure for my children, as well as having been a provider for my family were gone. The goal of having children to raise and a home to provide for had been accomplished. It was if my female side had waited in abeyance for this and now could not be denied any longer.

I fought off these feelings for exactly two weeks and five days from the day of my retirement before I couldn't take it any longer and spoke to my wife. This is the story of what happened.

-Robin begins her new life-

"Honey," I started, looking across the coffee table as we sat in the living room for an evening of television, "I, ummm..."

As my carefully prepared speech rolled to a tongue-tied stop, I got a desperate look and tried to find my way out of the blankness that had overcome my mind.

"You want to start dressing as a woman, isn't that what you are trying to say dear?"

My mouth dropped open as I stared at her disbelievingly.

"I have to admit, I have been waiting for you to bring it up, I honestly didn't think it would take this long after your retirement to do so," she said calmly.

"You've been thinking about this?" Was all I could think to ask.

"Of course, after nearly thirty years with you, I should know what is going on in that head of yours by now!" she declared. "I have thought about it, and decided that we should proceed as long as you allow me to control you completely. I do not want to be embarrassed, or feel that I am being forced by you to get involved in this. I feel quite forced enough by circumstances alone. I do believe you have been a wonderful, faithful and loving husband for all these years, and now you deserve this, but done my way! Agreed?"

"Agreed!" I immediately replied as my heart leapt.

"Not so fast there my little lady-to-be, things will probably be different than you would like, you will be brought along to your femininity at my speed, and with my tastes and desires in mind, not yours!" she jumped to inform me, "I will not be railroaded by your desires, or fantasy ideas into letting you do, or become, ridiculous or trashy, some style, and a general attention paid to my feelings being around you are called for!"

"I understand!" I declared hardly daring to hope that she would actually help me.

"All right, then I want your solemn promise to obey me utterly from now on!" she demanded looking at me sternly.

"I promise, I will obey you utterly!" I declared.

"Good, I was ready for this some time ago." she said getting up, "wait right here!"

I sat and just felt dazed, how could it have worked out so well? I didn't even have to say anything, let alone make a case for my desires. In a fog, I heard her come back and turned to see her come into the living room and sit next to me on the couch. She laid a small white box with beveled sides onto the coffee table and looked at me lovingly.

"Ok dear, first test, get undressed" she said, "now!"

I was surprised by her tone, but immediately jumped up and began removing my clothes.

As she watched me undress, she remarked, "I know you are transgendered, but after seeing you respond during some of our little dabbles with clothes during sex, I also know that it can be a turn on for you," she continued to watch me strip, "so I have decided to allow your sexual energy to be my control over your good behavior."

Just as I pulled down my boxers, she reached over and opened the box and tipped out the contents onto the coffee table. Out poured several lucite pieces, a hinged ring, a very penis-shaped cage, and some spacers. There were some white plastic studs of varying length, and some plastic tamperproof keepers like those used on utility meters. The last things were some instructions, and a small padlock.

"What is all this?" I asked hesitatingly.

"Well, this is a CB3000 male chastity device, I checked things out online, and found this to be the most reasonable alternative for my needs," she sat and stared at me, obviously waiting for my response.

"But why would we need that?" was the only thing I could say.

"Well, I can live with a man, and have sex, or I can live with a woman and have sex, but I refuse to do both, so from now on, you will be my woman, and so you will not be needing that little bit between your legs," she looked at me and patiently waited for my response once again.

"But, why, I mean, no sex at all?" I found myself whining.

"Well now, I never said that, but whatever sex we have will not need what you, as a lady, shouldn't even have between your legs," she said calmly, "so we will just remove the temptation for you to get any unlady-like ideas, and lock that problem away."

"But don't you like it when we have sex?" I asked disbelievingly.

"Oh, I plan to continue to enjoy our sex together girl, but whether you do or not will be up to you, not me!" she declared, "now let's just get this thing on you so we can get you used to your new role as a woman in this house!"

As I stood there stupidly wondering how this had come to pass as an idea my wife would even have, she spread the instructions out, and using some baby oil and an old scrunchy she retrieved from the downstairs half-bath, she soon had the device on me and clicked the lock shut with a flourish. "There, now we will have to take it off once a week to clean it, and you, and check for any soreness or chaffing, so in seven days we will have to deal with this again, meanwhile, just make sure you wipe after you use the bathroom, which of course, you will now have to do sitting down, and shower like regular in between times, ok?"

I just looked at her wonderingly and then looked down, and shook my head.

"OK?" she questioned firmly.

My head snapped up, and I nodded.

"Good girl, now I know you will have to practice your feminine voice, and I have some tapes to help you with that, it is amazing what you can order online, but in the meantime, I would like you to say as little as possible, in fact, I want you to say nothing to any question I ask you that is a yes, no, question, just nod or shake your head, understood?" she looked at me expectantly.

Not knowing what else to say, I just nodded.

"All right then Robin, it is Robin isn't it?" she inquired.

I nodded again.

"Good, well Robin, let us retire for the night, I have a beautiful full gown negligee for you to wear to bed tonight, and I think we should retire early. You will need some beauty sleep because you have a big day ahead tomorrow, we need to get started working on you, to make you the best woman you can be" she looked at me warmly.

I was thrilled by the idea of wearing a nightie to bed but looked at the clock that said seven-thirty and then looked at her again inquiringly.

She laughed a little laugh, and said, "Well, we won't be going to sleep right away dear, I have to try out my new girl lover don't I?" she said with a twinkle in her eye, "I have to try her on for 'size' so to speak, don't I?"

I stared at her for a moment, and wondered where all this was coming from, but then decided, what the heck, as long as she was going to help me become more feminine, I could spend some time giving her as much loving attention as I could. So I just nodded.

She smiled warmly, and then raised an eyebrow mischievously and took my hand to lead me into the bedroom, turning out the lights as we went.

Once we both cleaned up and got dressed in our nighties, we climbed into bed and lay there for a moment, me feeling strangely unsure and nervous about approaching my own wife sexually, for the first time in decades. Suddenly, Tracy turned towards me and said, "women like a certain amount of romance and a build up of sensation before the main event, whatever that might be, so just let me take the lead, and set the pace dear, ok?"

I looked at her with big, timid eyes and simply nodded. She then leaned over me and started to kiss me deeply, sliding her tongue into my mouth and making me feel wonderfully wanted. I slid my hands behind her head and neck and kneeded the smooth skin at the base of her neck and on her shoulders. We necked for a while kissing earlobes, throats and deeply enjoying each others mouths as first she, and then I began to slowly move out caresses down each others bodies. After a while we were both gasping and twitching with sexual need, she then slowly pushed down on my head until I got the message and went down to minister to her with my mouth.

A long drawn-out session of teasing, nibbling, and finally tonguing her followed until she let out a little gasp of pleasure and then pulled me up again to kiss me. "That was wonderful dear!" she exclaimed happily, "we must do this more often!"

I was pleased that she appreciated my efforts and was about to ask about my relief when she rolled over and turned out the lamp on her nightstand and went to sleep! I looked at her for a moment, rolled over onto my back, touched the chastity cage once, grimaced, and then stared at the ceiling for what seemed like the longest time before my aching body let me sleep.

"Wake up Robin, come on little lady, the sun is shining, and it is time to start your new life!"

I came awake and instantly felt uncomfortable, I had a morning stiffy, 'standing for the queen' as they say, and it was restrained at about one-quarter mast by the lucite cage around it. I jumped up, ran into the bathroom, and sat on the commode trying to relax enough to pee. After a while Cheryl walked right in, just opening the door and walking right up to me!

"Well, you've been in here long enough, problems Robin?" she asked with a smirk.

"Umm," I intelligently stated as I tried to think of a delicate way to describe my difficulty.

"I think I know what the problem is dear, you just wait right here for a moment, and then I think I can help you" and she turned and went out.

'All right! She is finally seeing the light and will get me out of this frustrating thing!' I thought to myself as I waited, 'She has probably gone to get the key for the padlock.'

A few moments later, she came in drinking from a glass of ice water and said, "I find that if I have any trouble letting go, then the sound of running water always helps!" with that, she upended the glass onto my crotch and freezing-cold water ran all over and into the lucite cage holding my much abused stiffy!

"Oww!" I yelled, "what did you do that for!"

"So you could hear the water run into the toilet honey, didn't it help?" she cocked her head at me inquiringly, "try to go now Robin, I'm sure you can."

I just looked at her a moment, then realized that my stiffy had gone down with the shock of the cold water and I could get the relief I needed. As I started peeing, she abruptly turned around and left the bathroom.

Finishing, I wiped myself, and followed her into the bedroom. She was standing next to the dresser looking into the drawer that I kept what little lingerie Robin, or, I guess, I had.

"Well, we are going to have to do something about your wardrobe today dear, you just do not have what any girl needs to get by in daily life," she said moving over to my closet, "we'll just have to make do, this sundress is probably the most appropriate thing you have to wear to go shopping, so get on your undies, and slip it on, then maybe the jute-strap sandals. Fix your hair and then your face, and I will go get a little something for us to breakfast on, can't go out shopping on an empty stomach!" She then turned for the door to the hall and started to leave the room.

"Wait!" I called with a catch in my voice, "I can't go out dressed like this, I'm not ready, I'll never pass!"

She turned quickly on me and said in a firm voice, "You are now a girl, you told me that last night, and agreed to do as I say in order to become one. Well, now you are, and since you are, you will dress appropriately! Do you understand me Robin!"

I looked at her determined, perhaps even fierce face, and found myself saying, "Yes dear..."

"Good! And another thing, I thought I told you not to speak unless asked to do so, at least until your voice is trained, now since you failed to listen, then I think we will have to leave your little cage on without any relief until you can ask me to take it off in a perfectly lady-like voice. Do you understand?" she asked with a lifted brow.

"Yes dear." I stated with eyes down and a feeling of shock as I realized it might be a while before I could manage a 'perfectly' feminine voice.

"Good girl," she replied turning for the door once again, "come down to the kitchen and have some breakfast once you are ready."

Watching her leave, I faced the fact that I was going to have to go out completely dressed, even though there was no way I would be able to look good enough with my current skills and looks to actually pass as a woman.

'What have I gotten myself into?' I asked myself as I moved over to my lingerie drawer, for some reason, a slightly modified scene from a television show in my childhood came to mind as I pulled out my bra and panties, 'Mayday! Mayday! Warning Will Robin-son! Oh! It's only you Mrs. Smith!"

Copyright BethanyDaWade