Are You Trying Turning Me Into A Sissy

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Chapter 33: Tattoo and a Little Humiliation.

We were expected at the tattoo shop, and the girl doing my design explained the process and checked the design.

I stripped off my trousers and pulled down my pants. I decided against tights, but the pants were obvious to the tattooist. Just before we were to start, Victoria whispered to the tattooist, and they stepped away and spoke in hushed tones. "Chris, I have asked if the design could be modified a little.

I am not going to tell you how, but it will be just as elegant and almost the same as what you selected. It's just that you have to consent, and I would like you to trust me and consent without seeing it.

Remember, I will never do anything to harm you. Consider it an act of trust."

I turned to the tattooist and said, "Okay, I agree to do whatever my wife asks."

It was sore, even a little painful, and it took some time. I could not see what was happening, but Victoria watched intently. It was in the same place I had agreed, but what it would look like, I had no idea.

"All done," said the tattooist, who helped me sit up.

"I suggest that you stand and check the mirror over there." I did as she suggested. The design was exactly as I had decided on the left side of my pubic area, but rather than being as discreet as I had intended, it was half the size again, about 1¼" across." Not so discrete; in fact, not discrete at all.

"Wow," I said. Victoria looked apprehensive. "It's as I intended, just larger.

It's done now, so there's no point in looking back. I like it." I did like it. It was what I wanted and what Victoria wanted rolled together. And it could not be undone. It was beautiful. The tattooist gave me care instructions and followed that by saying, "You are brave to have something so feminine, and I suspect that you and your wife love each other very much.

When you come back for your next one, you will have to tell me about your lifestyle. It sounds interesting." "I think that this one will be enough, thank you."

"I doubt that somehow. There will be more than one butterfly as the butterfly in you comes out. Remember that we do tattooed eyeliner and piercing as well. Perhaps you would like a new ring for the septum piercing I noticed."

"Maybe another day," said Victoria. I said nothing.

As we were walking back to the car, Victoria stopped outside a shoe shop, something having caught her eye. "Look at those heels." She pointed, and I spotted a pair of red patent court heels, and the heels must have been five inches.

"You could always use more heels, and those are so sexy, and I love the height. They would be amazing for your legs. They are also on sale at a bargain price. Come on, let's go and try them on."

"No, please don't do this. I can't go in there, and in any case, I'm wearing socks," I whined. Victoria thought for a minute, then pointed to a bench nearby.

"Sit there, don't move, and don't chat anyone up."

I sat and kept my head down. Five minutes later, she was back with a bag containing a pair of knee-highs, a pair of tights, and a pair of hold-up stockings, all in the same nude shade.

"Okay. I said that I wanted to push, and you agreed, knowing that there might be some humiliation. You were great today, and I know that nose ring is bothering you. But I have an idea. We are going into that shop, and you are trying on those shoes. It will be easier without socks and with hosiery of some sort.

So you have a choice. Put on the knee-highs here and now, or pick up the stockings or tights and go change in the toilets. Which is it to be?" Putting on the knee-highs would be easy, but in public, wow. Going to the restroom to change was a difficult choice.

I took the bag and walked off to the toilets. Five minutes later, I was back and handed Victoria the bag. She checked the contents.

"You went with the tights, I see."

"Yes. It made the most sense. I was worried that the hold-ups might slip, so I chose the tights. I'm a bit nervous about anyone seeing them under my trouser legs."

"Nonsense. Well done. Come on."

With that, she marched to the shoe shop. It was one of those with the shoes displayed up to waist height and the various sizes in boxes on the shelves below. Victoria found the shoe that she had seen in the window and checked the shelves for my size. She handed me the right shoe, and looking around, I nervously tied it on. It fit, and she handed me the other one.

They were fine, but I was worried about the staff and other customers seeing me whip them off. Victoria put them in the box and tucked it under her arm, but she also kept hold of the shoes that I had been wearing and wandered off down the aisle.

Here I was in stocking feet and no shoes. I scampered after her. A short way down the aisle, she spotted a pair of black peep-toe shoes with an ankle strap and heels of a similar height to the red ones that I had just tried.

"Sit and try these on. You'll need to sit to do up the straps." Shaking, I did as I was told. I did not see the shop assistant approach, but I heard her asking if we needed help. Victoria responded that we were managing fine, and I saw the girl look puzzled at me and walk away, shaking her head.

"I would get a move on if I were you. She might be back with the rest of the staff to check you out." Fastening the straps was hard with shaking hands, but I managed and stood up.

These too were a good fit, and I noticed the assistant looking in my direction. She mouthed, "Okay," and I nodded.

"Do you want to wear them home or change?" asked Victoria. I took them off without replying and handed them to Victoria. She picked up a black leather knee-length boot with a 3-inch heel.

She just looked at me and handed one over. By this point, I was nearly in tears. I was ashamed and worried about what might happen next, but I took the boot off and pulled it on. It fit really well, and so did the matching pair. I stood and pulled down my trousers over the boots.

I realized that, despite my shame and humiliation, I had an erection. It wasn't that I did not care or want to get away; I was in overload. Victoria knew that I was keen to get away and said, "Do you want to wear them home?"

My response was about to be, "Don't be stupid." But something in me snapped, and I have no idea what or why I decided what I did.

But I said, "Actually, yes, I will wear them home, and turned to walk away." Victoria saw the assistant, who had spoken to us, and headed for her. She explained that we would be taking three pairs and wearing the boots.

I did not hear the rest of the conversation but followed and stayed nearby, trying to be inconspicuous.

The sales assistant rang up the sales, and Victoria prompted me to hand over my credit card. The assistant looked at my name and dealt with the sale. She leaned over towards me and whispered, "You are very brave, and I bet that you have another name. Anytime you want more shoes, come back and ask for Natalie. I would be delighted to help you again." I

nodded but said nothing and headed for the door, only to hear Victoria say, "It's Missy, his other name. Thank you, Natalie."

I could not get back to the car quickly enough, although the heels did slow me up a little. I'm not sure that anyone actually noticed that a guy had high-heeled boots on. We did not speak on the way home. When we got home, Victoria started pulling our clothes off as soon as we had closed the door, and she fucked me senseless.

She laid back, satisfied. I thought back on what had happened. It had not been as bad as I expected, but even so, it was humiliating, and what is worse, it turned me on a little.

About 30 minutes later, she said, "I'm sorry that I was so forceful, but I knew that I had to do that, and it turned me on so much. I have no idea what comes next, but I know this is great, and from your reaction, it turned you in as well."

"I have no idea where this is going, but I do like it. It's just a lot to take on as it comes at me."

"Don't worry, I won't hurt you, but we are going further. You have a friendly shoe saleswoman now, and I'm sure that the tattooist was right; before long, you will want another one. Maybe even your own tits."

"Don't be stupid. I could never hide them. Do you want me to have tits?"

"I know that you like playing with mine, so don't be selfish. The day you ask for them, I suspect hiding them will not matter."

"I could maybe hide small ones."

"If you get them, you will not be hiding them, trust me. Now get dressed in something sexy and girly." I did dress. I put on the yellow 50s-style dress, did my makeup, and put on the red heels.

When Victoria saw me, she said, "I like the look, and I love what those heels do for you.

Clearly, your legs were made for high heels, darling. She was correct; I did like the heels. I have no idea why, but then again, I was a man wearing a wig, make-up, earrings, lingerie, a dress, nail polish, and 5-inch heels.

Somehow, I had gotten used to them. They did not bother me too much; I could wear them for long periods, albeit only in the house, and they felt good.

"I love them. I see that you are not wearing a corset."

"I know I just decided to go without. I like these heels, and I do like higher ones now that I have gotten more used to them.

Especially after my week of being dressed and wearing them almost all day."

We sat chatting with a glass of wine. "We don't have any plans for tomorrow, so we can play. Remember, though, that I am away next Friday and back the following Tuesday."

"I thought that you were going to see your friend Gina on Saturday."

"I am, and I have the days off, but they wanted me to see someone in Manchester that same week, so I suggested that I go and see them on Friday, and I can go straight to Gina's from there.

You should be okay on your own. I'll go to work Tuesday morning straight from Gina's and be home that evening." "Of course I will, although I will miss you."

"I suggest that you have dinner with Jess one evening." "That is a good idea. I'll do that."

"Can I trust you, though?" That's not fair, and you know it. It was you that she had a crush on, not me."

"Yes, I know I was just joking, but given how bloody attractive and sexy she is when she is away from work, you might change your mind."

"I hope that you are joking." I looked forlorn.

"Although I don't know about sex, we have never been apart that long."

"That is true. I will be as randy as hell by the time that I get home. I suspect that you will be as well. Mind you, you can always dress up sexy, watch some porn, and play by yourself."

"Well, I may deal with such matters, but not porn."

"Perhaps I should get you one of those chastity cages to make sure you don't play with yourself or anyone else. I read about them in some of those stories online.

"Are you serious?" No, just kidding. The thought popped into my head. It might be interesting. They are not expensive, and you could try them out, and in any case, it would only be five days, not a week.

"If you had one, I would try it out, but I would keep the key and would not be wearing it for more than a few minutes."

"Okay, it's a deal. It might be fun, it might not, but we will never know unless we try it."

"You are serious."

"Yes, but given all of the things that we have been doing, it is nothing that odd, surely.

"I'll leave it up to you. Order one if you have the courage, and we will use your rules.

Okay."

I went to my laptop, started a small job that I had to do, and checked bank stuff. I did go on the internet and look at the cock cages. It might be fun, and I would be in control; Victoria would not be cruel to me.

In some ways, I would show her that I was into trying new things and extending our fun.

I placed an order for a clear plastic one. I also did not tell her about it. We had a long lie-in on Sunday morning. Victoria went for the papers and asked me to start breakfast.

"Don't put on a dress today. What about your black night dress and negligee? But perhaps the corset and stockings, and of course the makeup and wig."

She was away longer than I expected, but I had coffee made and was dressed as she had suggested with the black peep toe ankle strap heels.

"That is some outfit. It is a shame that the night dress is so long that you don't get to see the effect of those wonderful heels on your legs."

After breakfast, I started clearing up and was sitting and reading the papers when Victoria came into the room. "Would you do me a favor and try this on, please?" She handed me a very short night dress; perhaps it could be called a baby doll.

It was cream with black lace trim. It fit around the bust, was elasticated under the bust, and was just long enough to cover my pants. It came with a sheer black short robe.

"I haven't seen that in many years."

"It was at the bottom of my drawer, and I had forgotten about it. I should have given it to you a long time ago."

Now my stockings and suspenders were on display, and the effect of the heels was apparent. "Back to your papers, darling." She wandered off. In the mid-afternoon, the doorbell rang, and I started to panic, but Victoria went, and I heard her say, "Thank you," to whoever was there before shutting the door.

It's a parcel for you, darling, as she came into the room. I was only expecting one thing, and I blushed red from head to toe. She saw the look on my face and gasped.

"You ordered one, didn't you?

Can I open it, please?"

What could I say? She split the tape and pulled out the cage.

"Oh, darling, this is beautiful, and thank you. Please, let's try it on."

I just nodded, and she sat back on the couch.

Victoria inspected the rings, found one to be the correct size, and snapped it in place.

"Oh my, I am so hot right now that I could come with the lightest touch. Are you ready?"

"I suppose so, but promise that it will only be for a short time."!

It was heavier than I had expected, and there was no mistaking that it was there. I quickly started to get hard, but was prevented from doing so.

"Victoria, it's on; now that you've had fun, please let's take it off."

"Yes, it's on, and I think it looks amazing. You need to leave it on for a little while, at least, or there is no point in it.

"Thank you for that; it was great, but I think that we should leave this on for a while. Imagine how much you will be able to enjoy when it comes off."

I knew that this would happen; why did I put myself in this position? I went to my home office but could not concentrate on work.

I opened a browser and started looking at cross-dress stuff. Then I found some images of T-girls.

They had breasts of all sizes; some looked like guys, but for others, it would be hard to tell. They came in all sizes, too. And it was at that point that Victoria walked in and saw what I was looking at.

"I don't know what to say. Do you like them?"

"I was just checking out some cross-dressing stuff and ended up here."

"Some of them are beautiful. Some I see are in the same boat as you at the moment. I was about to release you, but now I think that I should wait a little while longer."

We chatted some more and agreed that I would use it again but that I would control the keys. I now know that Victoria agreed, but she knew that for it to be effective, I could not control my own release, and it gave her a huge sense of power and control.

Chapter 34: Chastity and Absence.

On Friday morning, Victoria was up very early and getting ready to leave for the weekend, although she had packed the night before.

She called to me to remind me that I was going to take her to the station and that we would have to leave in an hour.

I showered and was starting to dress in a pair of black opaque tights and black pants with a matching camisole top beneath a dark dress shirt and slacks. Victoria came into the room.

"How are you? Recovered from our games last night?" she asked.

"Yes, darling, I'm fine, and I'm going to miss you."

"I know you will, but you have things to do. You can relax a little and take Jess out to dinner tomorrow."

"I will still miss you. I cannot remember when we were apart for 24 hours, never mind five days. Five days without sex!"

She walked away at that point. I sat on the end of the bed. I was sad. I would miss Victoria, and I also felt that I was letting her down. I had ordered the thing after all. But five days? I followed Victoria back to the kitchen.

"Remember when you dressed me as a goth and we got carried away with the piercings? That turned us both on. Then you forced me to try on the shoes, and I flipped and walked to the car wearing those boots."

"Yes, of course I remember. We were both turned on, and we both loved the sex. You quite liked the humiliation too, once you accepted that you liked it. Where is this going?"

"Do you really want me to wear the cage while you are away?"

"Would you really?"

"For you, because I love you, I will."

With that, we went back to the bedroom, pulled down my clothes, and fitted the chastity cage in place.

"I will conceal a key somewhere. Thank you. I love you."

Soon after that, we set off for the station. After dropping Victoria off, I headed to make a couple of calls to clients and reached the office about lunchtime. Just in time for coffee and a sandwich with Jess.

I had not forgotten that I was wearing a cage that would have been impossible, and at times it was uncomfortable. I found myself fidgeting to get comfy.

By the time I reached home that evening, I was going nuts. The cage was the only thing that I could think about. I went to the bedroom and stripped off. I checked the cage closely and then stood, looking at myself in the mirror.

I decided to dress. I put on the nude corset with the breast forms and a pair of nude stockings with the nude heels, and then tightened the corset as tight as I could.

I applied my makeup very dramatically and thickly. I added the black wig. I pulled on a silky knee-length robe and again stood in front of the mirror. I knew that the sight would be arousing, and so it proved it even if I was constrained. I pulled on a pair of French pants and discovered that they were much more comfortable over the cage than tights and tight pants.

I painted my nails. I went to get myself some food and a glass of wine.

The phone rang and broke the trance that I was in. It was Victoria, "Hi darling, just to let you know that I have arrived safely. I had a good meeting and am at Gina's.

How are you?" I told her that I was fine, and we spent a few minutes chatting about our days.

"I assume that you are still okay with 'it'?" she asked.

"By 'it' I assume that you mean the chastity cage that I am wearing and that is causing me discomfort? Well, it is still on."

"Okay, thank you for that; it has been driving me mad thinking about it. What are you wearing?"

"It has been driving me mad too."

I described my outfit.

"So you have dressed purely for yourself and done the whole thing knowing that I will not be there. You have come a long way. Do you want the key yet?"

"No, I don't want the key. Actually, I do want the key, but I am not going to ask for it yet. I want to try and prove myself both to myself and to you."

We ended the conversation soon after that.

About 10 p.m., I decided to go to bed. I kicked off my heels, got into bed dressed as I was without taking off my makeup, and laid back. It took me a long time to get to sleep. My mind was a whirl of sex, feminine clothes, heels, breasts, T-girls, piercings, tattoos, and, of course, the cage. Looking back, I think that something else gave way that night.

I don't know what it was, but there was a change and a greater acceptance of what I had been doing with Victoria. Sure, she had pushed, but I had done quite a lot of my own accord. I fell asleep, wondering what was next. I slept later than normal, for which I was grateful.

I stripped off everything that I was wearing, except the cage, removed the now-muddled makeup that I had slept in, and jumped into the shower. It was cold to start with, and I normally wait for it to heat up, but this time the cold stopped the erection. After showering, I went to get dressed. I gave it a little thought and did it on autopilot.

I dressed in a corset, stockings, French pants, a short skirt, and a sweater. I had added the breast forms, of course. I stepped into the pair of black heels that were going to be impractical and sat down to do my makeup and hair. I decided against a wig but brushed my own hair back and put it into a high ponytail. It was not that long for a girl, but my hair was far longer than most men wear it.

It looked okay. I had not given any thought to the fact that I was going out to dinner with Jess that evening. I made some breakfast and then got on with housework.

I changed the beds, did laundry, dusted, and cleaned, including scrubbing the bathroom and kitchen. By the time I had finished, it was about 3.30 p.m., so I made a cup of tea and sat on the couch.

I had been so busy that the cage had remained largely forgotten. I did not like it, but I was determined to see it out.

The next thing I knew was that I was waking up because the phone was ringing, and I assumed that it would be Victoria, but it was Jess. She sounded upset.

"Chris, I'm sorry to call you this early, but I've had a row with my dad, who is drunk.

He tried to hit me, but I ducked, then went and grabbed my stuff for the evening and left.

I know that we were not going to meet until later, but I don't have anywhere to change and hoped that you might let me come to your place."

"What now?" I replied, a little shocked. I was still dressed.

"Yes, is that okay?"

I looked down at what I was wearing and said, "Actually, I'm not ready yet, so it's..." I did not get to finish as Jess interrupted me.

"Chris, I mean Melissa; I'm sorry. I guess that you are 'dressed'. It's okay. I'll call Julie and see if I can go there."

Now I felt bad. Clearly, Jess had contacted me because we had arranged to meet anyway, and that made sense. Now she had a problem and was turning to her 'older brother' for help, and I was going to let her down.

She knew that I dressed and had seen my sop; what difference was it going to make?

"Jess, I am 'dressed' but that does not matter. You have a problem, and I want to help. Where are you?"

"I'm at the cafe near your house."

"Okay. Come on round, I'll put the kettle on."

She must have run, as the doorbell rang five minutes later. She was dressed in jeans, a sweatshirt, a coat, and no make-up. She had a holdall, and it was obvious that she had been crying.

"Are you okay? Chuck your bag and coat over there, and I'll get the tea, and you can tell me what happened."

She made no comment about how I was dressed. Over the next hour, she explained that her father had been out all night and had come home drunk at lunchtime.

He had confessed to playing cards and losing money. He demanded that she get him some more booze, that he was going to have a nap, and then she was to make him dinner.

When she told him that she was going out that evening, he called her a slut and told her that it was her job to take care of him and do whatever he needed. When she told him that was not her job, he tried to slap her, but because he was unsteady, she managed to duck. She had locked herself in her room and packed a bag while he was banging on the door, calling her names.

When he went quiet, she slipped out, went to the cafe, and has been sitting there trying to decide what to do.

We spent a long time talking about what she could do and reached the conclusion that she should try to go and find digs, possibly with one of the other hairdressers. By the time we got to that point, it was after 6 p.m.

"We should get ready if we are going out," I said. She looked thoughtful for a minute.

"Missy, Chris, I know that Victoria is away, and you asked me out because you were on your own. You dressed today, and I know that you would not go out as you are. We don't have to go out.

We could stay here, get a takeaway, chat, and maybe watch a movie." I thought for a minute or so.

"Okay, if you are happy with that, but remember, I'm a married man!"

"I did not mean to suggest anything inappropriate."

She looked slightly offended. "I was joking."

"Okay. I'm like scruff compared to you. Would you mind if I got changed into something smarter? And I could do your hair if you like."

With that, she went away to get her bag and went to the spare room.

Twenty minutes later, she reappeared, and my mouth fell open. She was wearing a purple dress that flared and stopped mid-thigh.

It showed a good deal of cleavage, and her legs were encased in sheer hose and looked very long, helped by a pair of purple heels with an ankle strap and very tall heels.

Her hair was swept in a French braid, and her makeup was light but stunning. "Wow, you look fantastic."

"Thank you kindly. Now, are you staying like that?"

"No, I need to catch up. I'll go and change."

"Give me a call, and I'll do your hair and make-up."

I changed into the yellow 1950s dress with a corset and matching underwear. I put on nude heels to match the stockings.

Jess appeared at the door and, without looking in, shouted, "Knock, knock. Ready for me?"

I sat at the vanity unit. Jess found a set of heated hair tongs, produced some hair gel and her combs, and set about styling my own hair. She did my make-up.

It was light and colorful; the hair was tightly curled and framed my face, and I looked incredible.

"Wow, thank you; it looks great."

"Yes, it does.

You have great features; dare I say, quite feminine? You look gorgeous. Can I snap a picture?"

"No" was my speedy and terse response. "Actually, I was going to say that I would use your phone so that you could show Victoria." I blushed.

"I'm sorry, Jess; of course you can. That was rude of me, and I should know to trust you by now." She took a couple of pictures. Then we went and ordered food and opened some wine. After eating, we continued to chat and demolished a second bottle of wine.

By 10 o'clock, there was very little that I didn't know about Jess's relatives—very few of them—school, college, boyfriends, her feelings about girls, and her ambitions. They were simple.

Work in hairdressing and as a beautician, possibly going to work in the media, TV, or films, and if that does not work out, have her own salon. Kids did not feature in her plans.

She also knew a great deal about Victoria and me. I was comfortable with her.

I felt sorry for her situation with her father, but there was little that she could do except try to find an alternative place to live. We decided to watch a film and sat side by side on the couch.

We ended up with our arms around each other, almost cuddling. When the movie finished, I noticed that she had tears in her eyes, and I was puzzled, as it was not a particularly sad story.

"I'm sorry. It's not the film. It's being here like this with you and knowing that you are someone that I can confide in and trust and who likes me. That is new for me. Thank you. But I suppose that I had better go home."

"No, I don't think that is a good idea. It's late; you have been drinking, and who knows what sort of reception you will get? There is a spare bed here, and you should stay." She smiled at me.

"Thanks, big brother and sister. Oh, you know what I mean."

I slept well because I had been distracted and had not really thought about the cage. I was in the bathroom when the phone rang. It was Victoria.

"Hi, darling. I tried to call last night and missed you. I guess that you were in the restaurant. We went to a club last night, and it was too noisy to call. How are you?"

"I miss you, and I'm fine, thank you."

"Did you enjoy your evening with Jess? Did you behave? Where did you go?"

"Yes, I enjoyed my evening, and of course I behaved. I'm almost offended that you have to ask." "I was joking. Where did you go?"

"We did not go anywhere; we stayed here. There was a crisis with her father, so we had a girl's night talking."

"A girl's night in?"

"Yes. I will explain everything when you come home. You know that I was locked up, so even if I had wanted to do something, that would have been difficult."

"I was joking."

"Well, she spent the night and is still in bed, I guess. Going home is going to be difficult for her, but we will sort it out. I've just heard her moving, so I'd better go."

"Okay. I'll call you tonight, and you can fill me in on the details."

I went and made breakfast. We talked about her going home, and I agreed that I would take her and assure her father about where she was and see how things went.

I dressed in my guy's clothes. It felt odd, and the tights that I wore held the cage close, and that made things uncomfortable. We went to see her father, and he was okay.

He apologized, and I assured him that Jess had been with Victoria and me.

I know that was not true, but I thought that it was better for him to believe that, and that would cause less of an issue for Jess. When I got home, I changed into stockings and became much more comfortable in the cage.

I spent the rest of the day working at my desk and knew that would give me lots of free time during the week, which kept me somewhat distracted. Victoria called that evening and

I explained what had happened. I even sent here the pictures that Jess had taken. She was shocked that I had been so open and willing to share my being dressed with her.

I was amused by that.

She had seen me several times and been to the club with us. On reflection, the cage had had an effect on me. Well, other than the one that kept me from getting hard!