My wife has long known that I liked wearing women's clothes. I let her know this after we were married. I actually thought I could stop my desires to dress as a woman once I had decided to settle down, but it did not take long once I had thrown out my entire female wardrobe that I realized that I could never stop.
Once I showed her what I looked like, it was clear she was not all that comfortable with it. I felt terrible about that, so I did what I could to keep my dressing to myself. I would dressup when she was not home. If I had to do it, I would come out and tell her I had the need to be female and would tell her I was getting dressed. This usually prompted a "fine, just stay in the basement" type of response.
Over time, I gradually worked on my wife. She began to soften her position on my dressing. She even asked me one Saturday morning if I would get dressed for her. I was surprised to say the least.
"I don't understand Lisa. You want me to wear women's clothes? Now?" I was really unsure if this was a test, or some kind of new fantasy Lisa wanted to try.
"Come on Jack. You have been after to me to let you be dressed as a woman for almost a year," she said matter of factly. "You already told me you dress, and I know where you keep some of your things. I even know when you wear my things. So lets not kid around anymore. You want to dress like a woman? This is you chance. But, if you want to dress like a woman today, then you will stay dressed as a woman all day. You can even wear any of the clothes I own, as long as it fits and you don't stretch it out.
I still could not believe what I was hearing. She could not be serious. This was some kind of test. It had to be. She had been fighting me, and telling me how she did not understand why anyone would want to be a sex they were not. I would try to explain to her that I did not want to change my sex, that I just like the way the clothes felt.
The only response I could utter was, "yea, right."
"What do you mean `yea right?' You have been saying there was nothing to it, and that you just wanted to wear the clothes. Well, here is your chance."
I just stood there with my hands on my hips. There was no way she was serious. But then she did something that surely began to move me down the slippery slope she always talked about when it came to my dressing.
Chapter 2
Lisa turned away from me and walked over to her dresser and opened the drawer which held her bras and panties. A moment later she had a lavender bra and matching panty brief in each hand. "Put these on. you know you want to," she said coyly.
The truth was I was beginning to get a little turned on. And as I looked at the bra and pantys, and then back at her face, I began to see that she was not kidding. This began to excite me even more. "Are you screwing with me or what?" I asked.
"How many times should I say it Jack. You want to wear my bra and panties, and what ever else right? So here you go. You have my full approval. You can spend the day dressed in my things."
I walked toward her slowly. Her last remark made me realize that she knew exactly what I wanted. I could not hide it. It was all over my face anyhow. when I reached her, she extended her hands and presented me with the bra and panties. I looked down at them, and reached out and took them. The thought that I was going to be dressed as a woman all day began to sink in, and while I should have been scared, or looking to hide, I wasn't. I realized that I was embracing it openly for the first time in front of someone else.
"Go to the bathroom and come out wearing them," Lisa said referring to the undergarments.
"You want to see me in them?" I asked, still surprised that this was happening.
"Jack, you will be wearing them all day, so I guess I should get used to seeing you wear them." She was so matter of fact and plain. There was no fear at all in her voice. This was new ground for me and I think for her too.
I turned to the bathroom, and closed the door behind me. I did not even turn on the light. I stood in the near dark, as the shade was drawn over the window, and removed what I had on; a t-shirt and boxers. I had been wearing a bra and panties since I was 13. I did not need the light at all. I slid the panties up my legs and secured them around my waist. The full coverage bra was a 36DD. All of Lisa's bras were full coverage as she could not get away with a demi cup. The bra went on, hooking in the rear with a three-hook closure. It was very comfortable. I was now fully turned on and it showed. "Are you done yet," my wife's voice broke the silence of my comfort.
This was the moment of truth. "Are you sure you want to do this?" I asked.
"I'm not doing anything. You are," came the reply.
I steeled myself, and just threw the door open to reveal myself to Lisa.
I thought she was going to laugh but she surprised me. "Comfortable?" she asked.
"I'm fine," I squeaked out. "Are you okay?"
"Perfectly fine," said Lisa. "But I think we need to help you out a bit. "Your D-Cups are empty and you will catch cold staying in underwear. I have seen your wig, so you should get that. do you use something to fill out my bras or do you just pretend you are small busted?"
I still could not believe she was going along so smoothly with this. It made me realize that Lisa might be more open then I thought. I began to think that it might become possible for me to be dressed as a woman more often then not. The thought of being able to freely wear what I wanted and when was very cool, I thought as I went to get my wig. This might become more then just dressing on occasion.
Once again, I should have became somewhat concerned that I was suddenly considering dressing up more as a woman then a man, but it just didn't hit me. I think I was thinking with something other then my head...the one on my shoulders that is. I think it was the smaller head between my legs, but in some way, it was my heart to . deep down I think that is why I was not stopping myself.
After I placed the wig on my head, Lisa began to question me as to what I wanted to wear. We were essential the same size. I was rather small for a guy, and I knew I would fit into her jeans and her skirts as well as her tops. Since it was Saturday, I suggested jeans and a simple top. she reached into her drawer and handed me a pair of Guess blue jeans and then emerged with a turtle neck without sleeves. It was a thin sweater texture. "Will these work?" she asked.
"I think they will be fine," I said. she handed me the clothes, then sat on the bed.
"Well, go ahead and put them on silly," she said with a cute smile.
I started with the jeans. They slid up my legs and over my hips and the lavender panties with ease. As a woman's cut, they had a bit more room in the tushy and hips, and tighter around the legs. They made my butt stick out as I had worn them before and knew what they would do to my shape. As I reached for the top, my wife interrupted.
"I think you're forgetting about a girls best assets...What about filling out my bra?"
I was feeling unsure. I had been using water balloons to fill out the bra's I had worn, but of course never in front of anyone. Now I was going to show myself with `curves' for the first time? My head was telling me to stop. That this was a point of no return, but I just went to wear I kept the already prepared balloons, and began to place them into the cups. Lisa, did not flinch. I now had the 36DD-Cup bra filled perfectly as it was used to.
"Good," she said. Now before putting on that sleeveless top, you have to shave your underarms."
"Lisa, I can't do that. I have never shaved before," I said in protest.
She looked at me as she stood up, and face me directly. "If you want to stay dressed in my things, then you will shave those trees under your arms." It was tern and clear. "Use my razor."
It took some repeat strokes, but the razor made relatively short work of the hair under my arms, and they were as smooth and hairless as Lisa's. I put on my top, and looked in the mirror.
Looking back at me was in many ways, Lisa. I had seen her wear this very outfit. My fake breasts were the same size as her real ones. The wig I was wearing was a medium brunette color, just like hers, and straight in texture with bangs, just like Lisa's.
She looked at me and said, "we could be sisters with a little more work."
The `little more work' stayed with me for the next several weeks.
Chapter 3 That day went on with me remaining in Lisa's clothes. I started in them at 9AM and stayed in them until 11:30PM, at which point we retired for bed. She asked me how it felt to be dressed all day and I asked her how she felt about me being dressed all day. I confessed that it took a bit of getting used to, but it was fine, and I liked it, and not hiding it from her. Lisa told me that by noon, she felt like she was talking to a sister, and became more comfortable with it as the day went on. She told me I could wear whatever I wanted if it made me happy.
"Just understand, that this is a slippery slope you on," she said.
"What does that mean Lisa?" I replied.
"Just what I said. you have started something that won't stop. And soon, just wearing my things wont be enough," she sat up and turned to me. "I don't have a problem anymore. I am okay with it, because it is just us, here. But what happens when you start shaving your legs, start wearing makeup and start going out while dressed?" Her comments hung in the dark a moment before she finished with, "just give me a heads up when you start with hormones and all."
I did not know how to respond so I just blew it off. "Awe come on Lisa. I just do this for fun. It's nothing like that.
"That's what they all say I'm sure. You'll see Jack."
"Who are you talking about Lisa? This is me. I am telling you, there is no chance I would turn myself into a woman."
With that we bid our good nights. It took me a while to fall asleep though. I was so caught off guard by Lisa's words. they kept ringing through me. repeating over and over. Was it possible? could I allow myself to become a woman or was this just about the clothes? The thoughts left me as I finally drifted off to sleep.
The next day I really resisted the urge to dress as a woman. Lisa did not raise it at all. We went through out normal sunday routine. Monday and Tuesday came and went. The concept to dressing up, or wearing women's clothes or becoming a woman was not discussed. But during those few days, I began to realize that I was feeling empty without that bra on, or the panties for that matter. I began to allow myself the thoughts of what it might be like to be a woman, and the thoughts felt great. Could Lisa have been right? Could it be that I just was beginning my slide?
As Thursday morning came, I found myself looking at my underarms in the shower. I could see that the hair had begun to grow back, and the stubble was clear and lengthening in the 4 days since I had first shaved. Almost without hesitation, I reached for Lisa's razor, and shaved under both arms. After I got out of the shower, and prepared for work, i just justified the act as no big deal. It would grow back soon enough.
Chapter 4 By Friday evening, Lisa and I were casually watching TV and I had no shirt on. she noticed under my arms. "You shaved again?" she asked.
"Ummm, ahhhh, yea, I did. Just yesterday morning actually."
Lisa just nodded. "So you what will you wear tomorrow?" she asked. "I guess saturday will be your day as a girl right?"
Well she had brought it up after a week of nothing about it. I could not quite tell if she was upset thought.
`I wasn't thinking about it actually Lisa. Did you want me to or something?"
"As I said Jack. Do what you want. No problem."
This pattern went on for the next two weeks. But then Lisa mentioned that she was getting her period the coming week, and to be prepared that she may not be so hot on the whole being a girl thing as she called it now.
"You know Jack, you want to be a girl so badly, you should get your period and deal with it all.
"Okay Lisa, like That's ever going to happen. Plus, I never said I wanted to be a girl. You're saying it.
Lisa retorted, "yea well you're th one shaving your armpits daily, and wearing a bra and panties every weekend. Now, I am supposed to do those things every day. That's what girls do. And, they get their stupid periods once a month."
I sensed some anger and frustration in Lisa, but I was not sure if it was the discomfort of the period, or that I was dressing up in front of her on Saturday's. "What do you want me to do Lisa? It's not like I can have a period to feel your pain. If I could I would, but I cant, so..."
We didn't talk for the next hour. I figured she was pissed at me, and while we went to bed, she said, "You really want to feel it Jack? My period I mean. Because I think I can ask you to do something that could help you understand."
I was just quietly thinking of a reply when Lisa said, "why don't we have a period together? We can both use tampons, only mine will go in my pussy and yours...well..."
I just looked at her incredulously. Was she really talking about inserting a tampon into my ass? I think the look on my face said it all.
"Well how else will it work Jack? There is no other way I can think of."
As I lied their I began to realize that the though of this was doing something unexpected. I was becoming very turned on. I had experienced some anal play with toys before getting married. I actually had purchased a dildo online, and loved the way it felt inside of me, so a tampon would be okay..."Sure Lisa. No problem. Just tell me what to do." The words just came out of me. It was like I was now in a trance.
The next morning, Lisa presented me with a wrapped tampon. "Our period is here. It came at 4AM. I didn't want to wake you but since your up, I will show you how this works." I didn't even hesitate. She showed me how to depress the tampon and have it insert into me, then remove the tube and discard it. Then to take the tampon out every four hours and replace with a new one. The caveat to all of this was that Lisa suggested I wear panties for the week that we were to do this experiment. I agreed.
Suffice it to say, the first day was rough. It felt uncomfortable at first. but I got used to the routine. By the end of the period, Lisa, told me that it was over, and I could stop using the tampons. That first day I felt so odd. I experienced an emptiness that I had never felt. Plus, wearing the boxer shorts instead of the panties felt even worse. As soon as I got home, I put on panties, and just sat their a moment. I figured I had the freedom to go forward and put on what I wanted. That's what Lisa said. So, I put on a bra, put the balloons in for curves, a pair of Guess jeans, and a simple white tee shirt.. Lisa came home soon after I finished dressing, and just looked at me.
"It's not Saturday right?" she asked.
"Umm, no," I replied. "I just...well..."
`It's okay Jack. It's okay.
Chapter 5 For the next 4 months, the slide down the slope continued. We continued to share period cycles and I had stopped wearing boxers altogether. I was now wearing only panties. I was dressing full on Saturday's and Sunday's and even some nights after work. Lisa kept reminding me that I was hurdling down the slope. I kept denying it.
One Saturday, while alone, and dressed, I began to surf the net looking for makeup tips as I had begun to wear make-up on the weekends. I stumbled upon a transgendered personal site and stayed on the site for over an hour, discovering the countless other men who wanted to become women. I had become convinced that I was becoming one of them too as my desired over the past several months to become a woman, began to manifest. Lisa's slippery slope was a reality, and I knew it. Once I created a profile, and photographed myself as a woman for all to see, I knew my future was set. I began talking to other trannys and shemales about their experiences and learned a lot over the next month. I began to shave my legs now. Lisa's comments were simply "I told you so," but our love life didn't change. we still made love. I even began making love to Lisa as a woman, with wig and makeup on.
With the warm weather now here, I knew that Lisa would like to lay out in the back yard by the pool and tan, and that if I was to be dressed as a woman, I would be somewhat expected to join her. I used to do so as a guy, why not now as a girl?
As the first warm day arrived, I say Lisa putting on her bikini. I knew she would spend this Saturday in the back all day and soke up the rays. I was just wearing a bra and pantiesÑmy own that I had boughtÑwhen Lisa chimed in. "Won't you jon me out back Jack?"
I was almost hoping she would ask. "Um, yes Lisa, but I really have nothing to wear for the pool. Maybe next week."
"Don't be silly girl. You can borrow one of mine."
Girl?' Did she say Girl?'
"Bikini or one piece?" her comment broke my thought. "I would recommend a bikini. You have the body for it, and as long as you tuck and wear your wig and some makeup, you'll be golden."
I was pleasantly surprised and thrilled at the same time. My wife was letting me become a girl. She even called me girl. She tossed me the bikini. I needed a little help with tying it in the back. She told me i looked great and that I should forget the balloons for this. It wouldn't look right. Our yard is very private. No one can see in, and I felt safe. But I was exiting the house for the first time as a woman. What if someone did wander back their and saw me? Gosh, that would be scary. But it didn't stop me.
We spent the afternoon in the yard. No incident. No one saw anything. But I didn't consider the effect the sun would have. Despite using SPF 30, I discovered a very deep tan line, and of course they were very definitely female.
Lisa and I showers together that afternoon. we had very similar lines on our bodies. She just looked at me and utter words that sent me wooshing down that slope toward what was now my destiny.
"I just can't call you `Jack' anymore. It is too masculine, and you just aren't a straight guy anymore. At least not to me."
"What are you saying Lisa?" I said as I stopped washing.
"Look at you. You wear women's clothes everyday now. You shave your legs, underarms, you use tampon like your having a period, and now you have tan lines. And, let me tell you `Jack' those line will take a long time to fade. Mine are always slightly their, and your could be too. You could never take your shirt off in public again."
I tried to protest a bit about wearing the women's clothes every day, but Lisa correctly pointed out that panties were women's clothes and that I wore then everyday.
The only sound was the water when Lisa looked at me, put her arms around my neck, kissed me gently, gave me a hug and whispered "Jacqueline," in my ear. We looked at each other and made passionate love in the shower stall. It was the most intense in our lives. When we finished and cleaned up, we agreed that it was time to see a gender therapist.
I did not fight it. And confessed for the first time that I might want to be a woman.
I thought Lisa would burst into tears and immediately want a divorce. But she surprised me again.
"I knew this would happen Jacqueline. And I would have wanted to leave you back before this began. But after giving it a chance, I realized something. I discovered that I can be married to a woman, and that I will love you even as a woman."
I was surprised of course, and moved. We both began to cry some. Our love for each other seemed stronger then ever.
"Lisa," I said as I wiped away tears, you realize that this will make you a lesbian to everyone outside of our lives?"
Lisa became very focused after she wiped away a tear. "In some ways you will always be a man to me. But in many others you are becoming the perfect woman. I never thought I could feel that way, or that I would be okay with you as a woman, but in truth I feel like you are closer to me now then ever before. and if you want to do this, and become a woman. I will support you 100%."
When Monday morning came, we called a gender identity therapist, and made an appointment.
(Like it so far? Let me know. I hope I can finish it soon...)