Urban
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Are You Trying Turning Me Into A Sissy
🕑 Added 2024-04-15 14:00:08 +0000 UTCChapter 7 - The next day.
We slept late. Victoria was first to head for the bathroom saying "I'll be back soon, stay where you are" and I soon heard the shower running. A few minutes later she reappeared with damp hair and fastening her robe.
"Now, I want you to strip, shower, and come back here.
But shave and make sure you are smooth. There is make-up remover on the vanity unit."
Twenty minutes later I was back. Victoria was dressed in skinny jeans, a tight T-shirt, and low heels. I was surprised and said so. "I want to get you dressed and then I'm going out as I need to get a few things and something for dinner. Sit here."
She did my makeup and groomed the wig before handing me a new pair of tights, a new pair of panties in white silk but covered with lace frills and a matching if somewhat less lacy camisole. She left me to dress in the same dress and shoes, gloves, and socks. "Meet me for coffee and croissants when you are ready."
She looked up as I walked into the kitchen and beamed. "You look wonderful; I love it and thank you."
"I love the feel of the clothes, make-up, wig, and shoes but I can't help but feel it's wrong for a guy."
"I suppose you are right that it's not mainstream, but if it feels good=" "You don't mind your husband being dressed as a sissy. I suppose I am a sissy."
"Yes, I suppose so, but my sissy and I love you. I'll be a couple of hours, don't answer the door and practice walking in heels.
Try walking backward in case you ever want to go dancing," she joked.
"There is no chance of that. Ever," I replied.
"Never say never. Look in the mirror and think back six months ago who would have thought. Mind you I suspect that you might just spend some time in front of the mirror when I'm out" She was right. I moved the full-length free-standing mirror into the long hall and walked back and forwards.
I did not try walking backward after nearly falling flat on my first attempt. I could not help but think a guy in a dress and wig was wrong but in truth, I loved the look and the feel of the clothes, the shoes, make-up, and hair. I still felt guilty.
My feet were hurting by the time Victoria came home and I had slipped them off a few minutes before she arrived. "What's this, shoes off?" she asked as she came into the kitchen.
"I sat down two minutes ago, walking in heels is not easy if you've never done it before."
"I'm not happy, part of this is about you doing as I asked. I'll be back in a minute."
She was unhappy and that disappointed me more than I would have thought. She came back with two lengths of pink ribbon.
"Shoes on."
And I stepped into them again.
"Foot up here," as she indicated a stool and tied a ribbon under the sole and tied it on top of my foot. It would not stop me from untying it but I would not be able to slip it off without a deliberate act to remove the ribbon. I was puzzled and could not fathom her actions as she did the other shoe.
"Why are you forcing me?"
I asked.
"I asked you to go along with this and you agreed. I was happy with how this is shaping up but the heels are part of this and I want to remind you of that with the ribbons and to get used to the heels. We can stop all of this if you want to go back, but neither of us do. I don't want to be cruel but we agreed that I should push you.
That's what I'm doing."
"Okay, I'm sorry."
"I bought you a present but maybe you won't want it."
"What is it?" I asked excitedly.
"Well, maybe you won't like it anyway. It's an ankle bracelet."
"Really?"
I asked as she brought out a box. She took the chain out and I saw that it had some text. As I looked closer I saw that the text said 'sissy'. The smile left me.
"I told you that you may not like it.
But yesterday you admitted that you were a sissy, my sissy, so I thought that it was appropriate and that it was just a bit of fun."
She was right, the way that I was dressed clearly indicated that 'Sissy' was the correct description.
"I'm sorry you are right. Thank you, please put it on me if you would."
She fastened it around my right ankle. With the ankle socks, it was hardly visible but it felt as if it weighed heavily.
"Let me see how the practice went."
I walked back and forth several times and she made a few suggestions to improve. "That is really good, well done.
I see that you moved the mirror was that to help so that you admire yourself?"
"Both," I sheepishly replied. We spent the rest of the day quietly. Victoria told me that she had been reading about crossdressers on the internet. She suggested that I do likewise and gave me a few sites to look at.
She also suggested some cross-dresser fiction. Some of the articles that I read were fascinating and most made me feel better about what we had been doing, about how I was dressed, and that there were far more men, and couples, like me. Some of the fiction was erotic, and some was scary. That night was a repeat of the previous evening. It was wild and erotic.
Chapter 9 - Sunday.
Victoria was once again up before me. I removed the ankle bracelet before the rest of the clothes and went for a shower. Victoria was waiting for me when I came out of the bathroom.
"Morning darling. Ready to get dressed? I want to try a slight variation if that's okay"
"Of course," was the only possible reply. "Instead of tights, I thought that we could go with stockings today and she handed me a pink glossy pair."
I took them and was about to put them on when an idea struck. I picked up the 'sissy' ankle chain and fastened it about my left ankle.
"Thank you, I really appreciate that. I intended to dress you like this because it turned me on and I thought that you would like it once you got over your prejudices. I love you so much."
I pulled on the stockings and held them in place with a suspender belt that I had not seen before. I put on the ankle socks and stepped into the shoes. I put a foot up beside Victoria on the bed and handed her a ribbon to tie the shoe. "I don't think that we need that."
I stepped into the panties, camisole, and dress and pulled on the gloves. I sat at the mirror for Victoria to do my makeup.
"Can I try something a little more extreme today?" she asked. "Of course, whatever you want."
She applied the makeup, applied it very thickly. She applied false lashes that she must have bought when she was out the day before. They were long, very long. I was instantly aware of them and when mascara was added I felt their weight. I loved them. These were followed by heavy eye-shadow and lip gloss. The wig was added and brushed into shape. Then she sprayed me with perfume. That was new.
"What do you think?"
"I love it. The lashes are something else and make my eyes look huge."
"I'm glad that you like the look. Earrings today, we forgot yesterday. I'm going to dust and change the bed would you help and get in some more practice in the heels?" We worked together for a couple of hours and it was very loving and there was lots of touching.
Victoria did some work during the afternoon and I read more fiction.
I learned a few things and realized that I do not want to be totally subservient but was prepared to allow my lovely wife to lead and make most decisions, particularly as regards our sex lives. I realized that some crossdressers/trangenders want sex with other males and some want their own breasts and or hormones.
I wanted none of that and resolved to tell Victoria of my thoughts later. After dinner, we cleared the table and did the dishes. "We need to talk. Thank you for this weekend you should go and change and then we can discuss it and where we go from here."
I thought about it for a few minutes, so long that Victoria looked puzzled. "What's wrong my love?" she asked. "Nothing is wrong.
Do you mind if I stay as I am?
You know that I enjoy the feeling of the clothes and the rest of the things, the makeup, shoes, and everything is good. The wig is a bit warm but it would not be the same without it. It makes the look."
"Oh, you lovely man. Of course, you don't have to change."
"Don't you mean lovely sissy?" I responded. "I do feel a bit guilty about that but as I said I realized that is what I wanted, I wanted you like this, my very own sissy but not at any cost. I knew that I would have to push a little but I wanted you with me and not resenting or disliking me."
"It's okay. I suppose sissy is okay, it's like Chris."
"No not Chrissy or sissy, we need to find you a name."
She thought for a minute "What about Melissa or Missy, kind of fits with Chris and sissy." Don't ask me why but I was so proud.
"Missy it is."
"Does that mean that you are prepared to do this again at some point? I'd like it." "What do we have on next weekend. I need more practice in the heels." "Are you sure?" "Yes, I am. I enjoyed this when I got over the shock.
But actually, the biggest shock was you being angry and tying on the shoes." "I have no idea what came over me and it was only symbolic, I never meant to mistreat you."
"I realized that when I gave it some thought. Was that you pushing things?"
"No, it just happened without any forethought."
"If we do this again next weekend will you push a little more?"
"No, I don't think so.
We made a leap this weekend and I have not thought beyond this weekend. Did you have something in mind?"
"No not really. But you are the instigator."
"Yes and I will continue to do so but I need to give it a thought. Maybe pluck your eyebrows into very defined arches, tattooed eyeliner, and breast implants? Don't panic I was only kidding about all of those.
That is much, much further than I think we will ever go." "I'm pleased to hear that." And with that, we went to bed.
Chapter 10 - The next weekend.
The following week was quiet by comparison. We both worked. I continued to wear feminine underwear beneath my outer clothing.
On Tuesday evening Victoria worked late so I decided to get some practice in the heels. They looked a bit odd being pink and worn with black tights and I kept my jeans on. That was how Victoria found me in the kitchen.
"Oh, my word. Practice?" as she raised a questioning eyebrow.
"Yes, but I didn't use the ribbons."
"Why not?"
"Because I decided to do this. Maybe next time or if you think I have been bad."
On Thursday evening after dinner, Victoria asked "Are we still on for the weekend?"
"Yes, I'm game."
"Okay, I won't be here until between 5 and 6. Do you want to start before I get here?" I got home at about 4 on Friday. I took a bath, shaved everywhere, and went to the vanity unit. I painted my toenails and fingernails. I fastened the ankle chain. I stared at the makeup. I had never done this but I started with foundation, eye shadow, mascara, blusher, and lip gloss. The eye-shadow was not right but I'm sure Victoria would fix it. I pulled on a pair of tights and panties. Then I pulled on the dress and shoes as I heard Victoria come through the door.
"Sorry I'm not done yet, I think that I need a little help but wanted to try it myself."
"Oh Missy, I'm so proud of you, let me help with the hair. I see that you didn't use the ribbons on the shoes."
"Not just yet. My eyes need some work."
She helped with the make-up, and hair and adjusted everything else.
"Go and start dinner and let me change."
About half an hour later Victoria joined me in the kitchen. She was wearing a purple nightie and negligee, what I guessed were black glossy stockings, and a pair of black heels that I had never seen before and which were incredibly tall.
My mouth dropped open. "Like the heels I see. Thought that I needed to keep them higher than yours."
"They are stunning. I didn't think that your legs could get any better but wow! What are the 5 inches?"
"Yes. I suspect that any more would be a problem for regular use outside the house."
"Well I wasn't planning in going shopping or to work in mine so maybe you could try something more extreme, but I wouldn't rush it.
Practice makes perfect, or so you said. Perhaps you need to tie them on" and laughed.
"What about those ballet boots that we saw, they were about 7 or 8 inches I think and they tied on"
"They might be a bit much.
They had them in pink and they would go with that outfit!" "No way" and laughed.
"Maybe one of these days when you want another bet I'll give you the option of ballet boots or pierced nipples."
For a change that made her stare open-mouthed. The weekend that followed was very loving and Victoria was delighted to find my ribbon-wrapped gift although by the time she found it, it had become a little too tight! We both practiced in our heels, and I got makeup lessons.
We read more fiction, drank lots of wine, and had lots, and lots of very good, satisfying sex. There was no dressing up the following weekend as we had plans, dinners, and socialized. It was a quiet period for us even though the sex was very good.
Chapter 11 - A New Dress.
I realized that there would be a dress-up weekend coming and as much as I loved the outfit a new one would give me a chance and allow the other to be laundered over a weekend. I did some internet research.
I found a pale blue silk dress that was much longer than the pink one but still had lots of underskirts and long chiffon sleeves.
I ordered white opaque tights and stockings some pale blue panties (with lots of lace) a matching suspender belt and a pair of plain white patent 3-inch heels with slingbacks.
I decided that I wanted a change of hairstyle for this outfit and ordered a black wig in a bob that was about chin length.
So totally different from the other one In the middle of the week Jess came to my office at lunchtime to ask me about something that she was doing on her college hairdressing course. Before she left she asked:
"Chris, I know it's none of my business and you can tell me to get lost but I am intrigued to know if you and your wife are still playing dress up? I know that I'm nosey but the truth is I really like you, it's not a crush and I think that I might be gay so please don't worry but I'm fascinated and cannot stand not knowing."
I did not really know what to say and gave it a bit of thought before answering, "Please understand that Victoria and I are very much in love and have no interest in anyone else. I really like you and I think of you as a younger sister, nothing else."
"I'm sorry Chris I did not mean to make you feel uncomfortable. I do like you and your wife I would not want to do anything to upset our friendship."
"Okay. Please do not discuss this with anyone else but yes we are still playing dress up. It makes for an interesting life."
"You don't have to tell me anything if you don't want to but do you have a dress?" I took a deep breath.
"Yes, it is pink and very sissy."
I blushed. Jess reached out and took my hand. "Chris I'm sorry I don't want to embarrass you."
"You know about the underwear so it won't matter that much. Actually, I've just ordered a new dress for this weekend, it's blue and very frilly. I'm going out at lunchtime tomorrow to see if I can find some earrings to match" I actually felt better for opening up.
"Chris, you are so brave and I would do anything to help you or just lend an ear. Would you like me to come with you, might be easier if they thought they were for me. You don't have pierced ears do you so it will need to be clip-on.
There is a much smaller choice. Unless you would like me to pierce your ears" and laughed heartily. That made me feel so much better. She just accepted my dress as being nothing that abnormal.
"No I don't have pierced ears and that might be too much." "Who bought your first dress, was it you?"
"No, it was Victoria, it was really all her idea. But I wanted to surprise her this weekend. Pierced ears might be too much of a surprise" "If you want to make a statement that would do it. My offer stands, I'll come with you and pierce your ears if you want.
Even if you keep the earrings in for the weekend the holes will heal in a few days and no one will ever know."
That thought remained with me for the rest of the day. It was like the first day wearing the panties.
No, I could not go that far.
On Thursday Jess was just leaving for lunch as I stepped out of the door and we ended up heading for the cafe on the corner and sat together. She did not raise the subject of my dressing during lunch but walking back she stopped to look in the jeweller's shop window.
I hovered nearby until she pulled at my sleeve and asked, "See anything that you like?" I stared into the window in a bit of a daze and then she pointed at a pair of long earrings which consisted of thin chains with numerous small blue stones of various shapes.
They were about 3 inches long and would be very noticeable.
My first thought was 'What a great color to go with the dress' then I realised that they were for pierced ears. Jess saw what I was looking at.
"I bet they would go with your new dress.
You should get your ears pierced it would be a great statement even if you took them out and you could change them for small studs hardly anyone would notice." I walked away from the shop in shock. She was right but somehow I could not speak. Jess chased after me and apologized.
"Chris I'm sorry I did not mean to upset you I was just having a bit of fun even if I am right. Sorry."
I went back to my office but could not get the idea out of my head. That evening I was distracted and Victoria asked what was wrong. "Nothing just thinking about the weekend" She smiled that very lewd smile and beckoned me to the bedroom.
The next morning as I was leaving the house Victoria asked, "Are we still playing this weekend?"
Yes, darling. I hope to get away about 3pm and should be ready to greet you about 5ish. Is that okay?"
"Of course it is. Any clues?" "No all will be revealed this evening.
I only hope you like what I have planned."
"Chris, I love you anything that you decide is okay except leaving me." "No chance of that." Later that morning I summoned the courage to speak to Jess. "Would you help me at lunchtime?" "With what?" "I want to get my ears done."
She beamed from ear to ear and leaned forward to kiss my cheek.
"Oh Chris I'm so happy I'll do anything to help. See you about 12.30pm?" We went to the cafe for lunch again and discussed what I wanted.
She suggested getting my ears done at the jeweler as she knew the girl who worked there.
That was too much.
"No we'll just buy them and you can do it before I set off home."
In the shop, Jess did all the talking asked to see the earrings, and held them up for approval as if I was buying them for her.
The girl asked, "We have a matching chain for a navel piercing if you are interested."
Jess responded with a polite, "No thanks."
Back in my office, Jess sterilized a piercing needle and my ears before making the holes and inserting the earrings.
"Wow they look great" I could feel them touching my neck, it was slightly erotic but my concern was getting home without being seen.
"Don't worry I'll check that the coast is clear and slip you out of the back door. You should have got your navel done as well though"
"Thanks for all your help, but that would be much too much," I replied.
Comments
Urban
π It's a pity I missed out on this number.
Brett Schuhkraft
I hate to be picky but what happened to chapter 6 and 8
J Chimera
He is giving ground on his fears and prejudices little by little. He might even reach a point where he will seriously consider the addition of breast forms to his persona at some point. This is a wonderful, well crafted story that keeps getting better and better.
nancy
Too good!! Iβm still thirsting for more and more of this!!! Please???
nancy
nancy is an absolute fan of his piercings and agrees about the navel. I truly love this potential inclusion of Jess-and the idea of even more people being involved. Divulging their kinks is hot. Iβm hoping he becomes addicted to the humiliation and fetishizes the activity.
Brianna Demonet
I love the idea of his ears getting pierced. He definitely should get his naval pierced as well.
Amanda
Thanks URBAN for sharing another photo with us.β€οΈπββοΈ
Amanda
Enjoying this story. The restraint of Victoria is a refreshing change from the usual expectation. I am a little tense about the intrusion of Jess. She seems quite pushy and potentially a disruptive influence on the relationship. Hope i am wrong.πππ»β€οΈπββοΈ
