Are You Trying Turning Me Into A Sissy

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Chapter 17 - The New Dress.

I finished sharp that Friday and made my way home. I soaked in the tub and after drying painted my toenails using the purple nail polish that had been left for me. I pondered what was going to happen later as I let it dry. Then I pulled on a robe and went to start dinner preparations. I purchased a new ring for the ankle chain and fastened it around my ankle.

The ring replaced the broken clasp and I had to fix it with a pair of pliers. I had decided that it would remain on and not remove it. It was symbolic of how I felt I suppose, and no one was going to see it.

An hour later Victoria arrived. She looked as if she had had a tough day. I handed her a glass of cold white wine.

"Thank you darling just what I needed to start with. I need a shower and clean clothes. See you in the bedroom in 30 minutes."

I sat at the dressing table in our bedroom and waited. Victoria came out of the bathroom looking stunning in a red silk nightdress with a matching robe over it.

Her hair was pulled back into a bun, and she wore very dramatic makeup and quite a bit of it. I noticed a pair of red hose, stockings or tights I didn't know which and a pair of patent red heels.

She said nothing but handed me a white camisole and pants set and a pair of beige, 15-denier, glossy tights. I pulled them on. I sat down again and she applied false nails and painted them several coats of purple polish.

In between coats drying, she did my makeup. There was plenty of it but it was subtle and the long lashes were back.

She used the blonde wig from the first outfit and tied it off of my face with a purple hair band. She changed my earrings for a pair of very long ones with purple stones at the end and said, "I forgot about this."

She handed me a navel chain that matched the earrings. I inserted it. "Nearly ready, just the dress and shoes. Now, this is different and I think it may shock you a little."

She was right. The shoes were the white slingbacks that I had bought for the blue outfit and I slipped them on, then Victoria pulled the dress from her wardrobe.

My mouth fell open, I have never seen anything quite so outrageous, so feminine, so girly. I never uttered a word as she helped me into it and zipped it up at the back.

It took a bit of effort as the dress seemed to be a shade tight but once it was on I stared into the full-length mirror. It was a shock, she was correct.

It was girly, very girly but not really sissy except I was a guy so maybe it was sissy, who knows, I wasn't really caring.

This was an impractical dress but I realised that I loved the look. "Wow" was all I could say.

"Chris, sorry Missy, it is amazing, I love it and I think that you do as well."

  "Yes, I do."

I stared at my reflection but I had nothing else to say.

"I see that you have the ankle chain on, did you get a jeweler to fix it?"

"No, I did it myself." "Where did you get a clasp?"

 "I didn't. I got a new jumper ring and fixed it," I stated still staring at myself. "How will you get it off them?"

"A sharp tug will break a link or a pair of pliers to undo the ring."

 "But that's a bit of a hassle, isn't it. I could get it repaired for you."

 "No thank you. It won't be a hassle because I'm not going to take it off. If something crops up that means it has to come off, it will be easy enough to open the link."

"You are going to wear an ankle chain that says 'Sissy' permanently?" she queried.

"Yes, I am."

"Wow," was her only comment before she left the room. I found her in the lounge sipping a glass of wine. My glass was on the coffee table. Nothing much was said about the outfit during the evening.

I kept checking the mirror, and Victoria kept staring. The sex was as good as it has ever been and went on long into the night.

 Chapter 18 - The next Day.

The following morning Victoria was up sharp and delivered me a cup of tea as she kissed me awake. "Darling, I need to go out for a couple of hours. Why don't you chill out, have a shower, do your makeup, and slip on your underwear and a robe until I get back. There is some laundry to keep you busy."

Three hours later Victoria came home with some bags, and the shops had been visited.

"Hi darling, finish what you're doing and join me upstairs." Ten minutes later, the dishes were put away, the laundry folded and I headed to our bedroom.

"Yesterday I noticed that the dress was just a little tight and because of the bodice being stiff it didn't look quite right so I have bought a couple of things to help. Please be patient, don't panic and you'll see."

 With that she moved towards me with a long bra, actually, it was a waist cincher type garment with lots of fasteners at the back like a bra. I know that I felt faint but she wrapped it around my torso and fastened it. It pulled me in, it made my breathing shallower.

Bloody hell I was wearing a bra! She had me step into the dress and it fastened so much easier and I could not deny that it enhanced my shape.

Wait, I was a guy, who enhanced my shape? Well, it did. Then she handed me a pair of new shoes, these were beige peep toe court shoes with a 4-inch heel. I stepped into them.

Instantly I was aware of the height difference but in the mirror, I also noticed two other things, they matched the color of my tights exactly and made my legs look astonishingly shapely and long, actually sexy.

"Oh my goodness."

"You like?" Victoria asked.

"Yes, I do. A bra is a bit scary though."

"It's not actually a bra."

"It has cups," I retorted.

"Yes, it does. But it gives a better shape, although there is one more thing that I could do if you were feeling brave."

"What? What else could you do?"

"Close your eyes."

I did so but now I was starting to tremble. Victoria unfastened the top of the dress and coming in front of me slipped something into each of the corsets or bra cups, I was confused about what it was called but that was because I knew that she had just added breasts!

She rearranged and fastened the dress again.

"Keep your eyes closed," as she fussed about and led me to the mirror.

 "Now you can look."

I looked, I saw, I nearly swooned. My god that was astonishing, my shape had changed a fairly small amount but the difference was immense. , I looked so good, I felt right, I felt like a girl.

I loved it.

"They are called breast fillets, women use them to give themselves an extra lift. I was scared to try them on you but now that you are dressed they make a huge difference.

What do you think?"

"I don't know. They make a huge difference. It looks, I look incredible. But a bra and breasts?"

 "It's just you and me. It's between us. We love each other. Tell me that you don't like it or are uncomfortable and I'll remove whatever you want."

 "I don't want you to remove anything. I love it but I cannot help feeling that a line has been crossed. I don't know what that is yet but maybe I just need time to adjust."

"I love you."

She gave me a small kiss on the cheek as she left the room. I stood in front of the mirror.

I stood and stepped in front of the full-length mirror. There was the image of a young lady in very feminine clothing, beautifully made up, hair done nicely.

Smart, fanciful, shoes with a heel that emphasized the shape and length of the legs to which they were joined at trim ankles.

Long bare arms with a bracelet and long talons at the end of the fingers.

The waist was slim and emphasized the bust, all in all, a very shapely lady. It was me! It was hard to believe that the person in front of me was me, a guy. Since this started I had believed that a man in female clothing was odd, perhaps wrong, not mainstream but I had enjoyed the feel and the sexiness.

Here I looked again and realized that all of those feelings were incorrect, there was nothing wrong with this image, it was right, it was comfortable. It was me and I loved it. I turned around and realized that Victoria was not there. She had left the room. I made my way to the lounge where she was seated sipping wine.

She gestured to the glass for me on the coffee table and I took a sip and stood before her.

"Finished admiring yourself have you?" she queried. "Yes. It was a bit of a shock."

"Why was that?"

 "Well, the outfit is beautiful. It seems 'right' somehow," I replied.

"Despite the tight long bra and the breasts?"

"Yes, Somehow it looks and feels right. The clothes, and the outfits before have felt good but this is different, this feels as if it is right. Not making myself that clear I know."

"Actually I do understand. Until now it has been playtime, a fantasy. This looks as if it is really you."

I realized that Victoria was correct. This was me although I did not know what was ahead and I doubt if she did either.

Clearly, I was still a man in a dress but I did not feel too much like a sissy. I felt as if I had matured and tried to explain it to her.

"I think that you are right and we may need to talk over the weekend but for now let's have some wine and relax. What do you think of the shoes?"

"They are really nice and match the outfit. Stylish and comfortable," I replied.

"They matched and are cute. I know that you like the high heels.

Why is that?" she queried.

"I love the way they emphasize my legs. But you are constantly aware of the higher heels. That is not right I am constantly aware of the hosiery, the clothes, the swish of a skirt, the feel of the make-up. But you can forget, briefly, that you are wearing them.

 With the higher heels, you cannot forget that you have them on, you are always aware of the position of your foot and leg even when sitting down, and you have to think before you start to move.

The ones that I had were low enough that now I didn't have to think about it. It came naturally but these will take some practice but I'm sure they will be fine."

 "Wow. Perhaps we need to try something a bit more extreme."

"Yes. That would be good to try but most of the higher heels either have platforms as well, which look clumsy, or they are really fetish wear."

"I will see what I can find and you should look too."

The rest of that afternoon we did things in the house, then cooked a dinner, watched some TV, and went to bed early. As ever the sex was great. The following morning I was just coming out of the shower when Victoria came back into the bedroom.

 "What would you like to wear today, yesterday's outfit or something else?" she asked. I was tempted to go with the same outfit but it had been worn for two days and looking worse for wear. Victoria spotted my dilemma.

"I have an idea. It involves your first outfit."

I blanched "The sissy dress?" "You call it that if you wish. But, yes that dress.

I'll pick the clothes and do your makeup a little differently." "Okay," was my nervous reply. Victoria produced the waist cincher and fastened it on.

It felt tight again but somehow comforting. She added some garter straps and then some nude glossy stockings and the pink lacy panties. She asked me to step into the new shoes that matched the hosiery and then pulled the dress on.

It was too short with the stockings and I started to protest but she just shushed me.

I said nothing. The breast fillets were added.

"Sit at the vanity, face away from the mirror and I will do your makeup but it will be a different look."

She added some earrings that I had not seen before, a string of gold hoops that I could feel touching my shoulders.

In the brief glance that I had at them, they looked a bit slutty. She then did my makeup. Heavy foundation, rouge, long false lashes, several coats of mascara, a lot of eye shadow, and very red lipstick.

 I could feel the makeup, thick on my face. It would be hard to not be aware of it. Victoria added the blond wig but styled it a little more. Eventually, she allowed me to stand and look in the mirror.

Wow, I was wearing the sissy dress but looked like a slut, a very cheap slut. I felt embarrassed and started to redden, and then I looked again. Yes, I looked slutty but somehow the feel of the outfit, the cinched waist the breasts the heel height, and the feel of the makeup felt good.

Victoria surprised me, I had almost forgotten that she was there.

"I'm going to get a coffee. Take a good long look, think about the look, and then come and talk to me."

Twenty minutes later I joined her.

 "Well?" was her only word. "I'm conflicted. I like the feel of what I'm wearing, including the heavy makeup.

I'm not keen on the tops of the stockings being visible and I look slutty.

It feels good but it's not my look."

"I love it. It looks sexy but you are correct it's not you but I had to find out. Interesting that you have not commented on the height of the heels, the tightness of the cincher, or the breast fillets."

"I love the heels and the extra height. The constriction feels okay and together with the fillets it creates a great figure."

"So you like having tits then? Perhaps we should get some bigger ones, or maybe even real ones," she asked. I nearly fainted.

 "Real ones?"

 "I was joking, at least about the real ones. Bigger breast forms." Victoria was thoughtful and then asked, "Can you tell me why what you are wearing feels okay when a couple of months ago it was humiliating?"

 I thought about that for a few moments.

"You clearly had an image in mind when I dressed fully for the first time and that was a sissy.' I found that humiliating even though you explained and were kind. Think about it now though I wear women's underwear and hosiery every single day, I have no hair on my body, and I don't know how long it is since I last went for any length of time without my toenails polished.

My ears are pierced and I frequently dress entirely in women's clothes, sissy clothes really, and I wear an ankle chain that says 'sissy' and which I fastened on myself.

No guy does this to himself, but a sissy would.

I accept that is what I am a sissy and I like it although I don't want anyone else to share this secret."

Victoria looked stunned.

"Wow, I see. But Jess knows and has seen photos and I'm sure that Julie probably has some idea."

 "Have you told her?"

"No, I have not but she knows something is going on, she knows that you have been wearing hosiery. I promised that I wouldn't tell and I will keep my promises but one day someone will find out and it may be best, if we continue, for you and I to control that."

I didn't know what to say but it was certainly something to think about.

"I have some office work that I need to do this afternoon but I have something that I want you to do. I want you to read some more stuff on Fictionmania so that we can talk about some of the things in the stories.

We are busy next weekend, but the following weekend we can spend together, so I want you to look for an outfit.

Everything has to be new; clothes, underwear, jewelry, shoes, wigs, and makeup everything, and you have to select it and buy it. It should be dressy, the sort of thing that you would wear if you were getting glammed up.

Not sissy.

"I want to see what you select."

There was nothing that I could say in reply so I spent the afternoon shopping, browsing, and reading.

 I placed orders for a dress, a new wig, shoes, underwear, and hosiery.

 I decided that I would have a look for makeup and jewelry during my lunch breaks over the next few days.

Victoria finished her work and helped me with preparing an early dinner. Over a glass of wine, she asked "Well have you selected an outfit or made any decisions yet?"

"Yes I have, but that is the last thing I am going to say until I have everything and we are ready to go."

No more was said. We had an early night and great sex.

Chapter 19 - Interesting preparation week.

 The next week continued with me dressing in underwear daily and some evenings practicing in heels. One lunchtime I spent some time looking at makeup in a department store and the assistant offered to help me with my colors. It was humiliating but she was great and I managed to get the correct things, even though I spent a small fortune.

Later that same afternoon, Jess stopped in for a coffee at her break and she saw one of the bags.

I saw her looking but she didn't say anything.

That morning I had put on opaque tights and I noticed Jess looking at my ankle. She could hold back no longer.

"Chris, I'm sorry but I have two things to ask you and I will respect that you may not wish to answer. Before my first question, I promise that I will never discuss anything that we talk about with anyone else, including Victoria."

I realized that this was going to be difficult but she was going to ask anyway.

"Firstly I may decide not to answer, that depends on the questions but whatever happens I will tell Victoria about our conversation whatever you ask and I would appreciate it if you would keep your observations and my answers to yourself."

She took a deep breath and said, "Okay, I have two questions but the answers may lead to more questions."

She stopped and I could see her thinking before she carried on.

"I assume that you are still 'dressing' and wearing ladies' underwear?"

I hesitated a moment but she interrupted.

"Actually, you are wearing 40 denier tights or stockings so I know the answer to that. Are you wearing an ankle chain and what's in the bags from the department store that are not very well hidden near your desk?"

 "Wow. Please promise again that you will not discuss this, but seeing as you know some of this I will answer and I hate to lie."

 "Okay, I swear." "Yes I am wearing an ankle chain and I assume that you saw it through the tights."

"Yes, I caught a glimpse of something shiny when the sun caught it just now."

"When we first started this Victoria gave me an ankle chain that said 'Sissy.' I hated it at first but came to realize that a man in women's clothes could well be described as a sissy so I wore it when I dressed.

Then I caught the catch and it broke.

I decided to repair the catch so that I could wear it and because of things that we had done I kind of recognized that it was right so instead of a new catch I inserted a new jumper ring. I wear it all the time." Jess just stared at me.

"Oh Chris, you are remarkable. That is lovely and you must be so secure to do that." "It all makes me nervous but it is not something that we are going to stop shortly."

"Do you still have the navel chain and wear it?"

"I have three, I think, and I don't remember the last time that I was not wearing one of them except when I was swapping them over." "Oh, wow."

As for the bags, Victoria asked me to choose and purchase a new outfit, everything. I got most of it mail order but makeup is a little trickier.

I plucked up the courage and went to the store at lunchtime and the assistant guessed most of the story and helped me out. She helped me get the correct colors for my skin tones."

Jess sat there gawping with her mouth open. Then she got up came over threw her arms around my neck and gave me a big hug.

"Oh Chris, you brave wonderful man. I don't know what to say. I'd better get back to work."

She closed my office door and seconds later poked her head around it.

"Next time you need to go shopping, please ask me and I'll help. You might find it a bit easier."

Later that evening, over a glass of wine, I told Victoria what had happened with Jess. "Really, that is amazing.

I think that she is right, her helping you would make it easier if you are comfortable with that.

I will have a word with her next time I'm getting my hair cut. Just realize this though. At some point, she is going to want to meet Melissa and you will not be in a position to deny her so you had better think about how to control that."

Well, that gave me something to think about.