Are You Trying Turning Me Into A Sissy

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Chapter 35: Victoria Returns Home.

Monday and Tuesday were normal days in the office. Of course, I was dressed as Chris with normal guy's clothes, but underneath I wore pants, a camisole, and a suspender belt to hold up my stockings. This made the cage slightly less uncomfortable. 

I kept busy to keep my mind away from thinking about anything that might start me to become erect, but in truth, that thought was never that far away, and I was constantly distracted. 

On Tuesday, I left the office mid-afternoon to go home, change, and get some food ready for Victoria to arrive. I decided to wear the white and purple dress and nude stockings, supported by the beige corset and nude heels. 

That dress was a little too tight for the breast forms, so I was only padding the corset out with the fillets. 

I did my make-up and nails and then tried to repeat what Jess had done with my own hair. 

It was not too bad. I prepared a salad to go with the steaks and had everything ready when I heard the door. Victoria had dropped her bags, ran to the kitchen, and squeezed me.

"Darling, I have missed you so much." 

With that, she stepped back to look at me. 

"Well, I see that you look lovely; a corset gives you a great figure but a modest bust."

"Yes, the forms were just too big for this dress."

"You look great, and the hair is good too. How did that come about?"

"That was Jess's idea on Saturday. I'll tell you all about it. Do you want a glass of wine or to eat?"

"No. I have been going crazy thinking about sex. 

I've not touched myself and have missed the sex, but the thought of you locked up has me slightly mad."

"How do you think I have felt? 

I suggest you go to the couch, remove the pants, and let me help you out.

"With that, we moved to the lounge, and Victoria stepped out of her pants and handed them to me. They were soaking, as was she. 

I spent about twenty minutes between her legs, and at one point she passed out for a few seconds. I cannot tell you how much pain I was in with the erection trying to burst out of the cage. 

Thank you, darling. I can't tell you how good that was. 

Get the key. Where is it? 

In the little pot on the coffee table. 

It is a miracle that I was never in there. 

However, even if I had found it, I would not have used it. You asked me to do it, and I gave you my word. But please take it off. 

She fetched a warm washcloth, removed the cage, and wiped me down. It was slow to react and then became painful as it got harder. 

She slipped her lips over it, and my knees buckled at the warmth, and I came. It took us both by surprise. 

It left me shattered. After about an hour and a glass of wine, I felt better. We ate and went to bed for the rest of the night. 

I have no idea how many times we made love, but it seemed like a continuous process, and it was great. 

Late in the evening, Victoria went quiet for a while and was clearly thinking. 

"I don't think that we should play with the cage again. Tonight was fun, but I know that you suffered, and I don't want to do that again.

"I think that it made me very compliant and light-headed. It never left my mind, and when Jess called me, I just accepted her seeing me dressed. But I think that you are right. 

Okay, so now spill the beans about your evening with Jess.

We spoke for hours about what we had done and what she had told me.

"I like her," said Victoria, and then she told me about her weekend with Gina. They had been to dinner at a club and gone for long walks, but mostly just chatted. 

"I enjoyed the weekend; apart from missing you, it was fun. Actually, there is a three-day conference in a couple of weeks. 

I have some business in the city, so it might be a good idea for me to go up there for a week. Would you mind?

No, I suppose not. If you need to go to work, you could kill two birds with one stone. I will be fine, without the cage." 

Then we cuddled and fell asleep. The rest of the week was quiet. 

We both worked hard but took it easy during the evenings. I didn't dress, apart from underwear and hosiery, but we had lots of early nights and sex, catching up on what we had missed. 

Victoria asked if I had plans for the weekend, and as I didn't, she suggested that I dress up. 

"Do you have any suggestions?" 

I asked. 

"Goal out Friday and everyday wear during the day, and we will see where it goes." 

Late Friday afternoon, I put on the black 1950s dress with appropriate underwear and my highest heels. 

I used a black wig and long false nails and did a very dramatic evening make-up. Then I went to start preparing for dinner and chilled plenty of wine. 

Victoria clattered through the door, laden with bags—her handbag and laptop case.

"Sorry. I should have made two trips to the car. 

What do you have in those?"

pointing to the bags. We'll check on them after a glass of wine and dinner. I'm off to change. With that, she disappeared and returned soon after, wearing a very elegant nightdress, robe, and heels. 

She had sorted her hair and freshened her make-up. She was truly a beautiful and sexy woman. We ate dinner and chatted about work. 

Once we had cleared away, we took our wine into the lounge." I was at a meeting until lunchtime and decided to walk back to the office. 

I passed a very fancy charity shop and saw a suit in the window, so I went in. It turns out it was your size and not mine. I spent hours browsing and ended up spending a small fortune, but only a fraction of what the stuff would have cost new. Want to look? 

She came back with a beautiful evening gown. It was floor-length, had a halter neck and deep cleavage, and shimmered with blue sequins. 

"This is for me for the next dinner that we have; the rest are for you. 

She showed me a two-piece gray wool business suit. It had a knee-length skirt and was neatly cut around the knees. The jacket was double-breasted with a shawl collar and could have been worn with or without a blouse. It was very smart. Next was a one-piece red jumpsuit. 

It was tailored so it would fit neatly, had a deep V front, and slightly flared trousers. I was slightly surprised that Victoria would buy me anything with pants, but no one would ever confuse this with being masculine. 

It was beautiful and could be worn for an evening out or for a smart occasion during the day. 

The next item was inside a garment bag, and when I drew down the zip, I saw an evening gown. 

It was a blue-gray, mainly chiffon. It had a full skirt attached to a neat-fitting strapless bodice, but the upper half was covered with what looked like a lace blouse and sleeves that stopped at the elbow. It was stunning. Wow, that is beautiful. 

Yes, it is. Let me drop your zipper, and you can try it on."

I turned around, and Victoria pulled down the zipper, and I stepped out of the door. Victoria had taken the evening gown from the garment bag and hanger. I stepped into it very carefully. It was obvious that it was well made and that it was going to fit very well. 

Victoria pulled up the zipper and fastened the little button behind the neck. The length was perfect, and I felt a million dollars in it. We both admired it and agreed that it would be a great outfit for a dinner event. 

There is one more thing for you, but it won't really go with that dress. She produced a pair of purple suede court heels. They looked incredible, mainly because the heels were very slender and at least five inches tall. I could not resist trying them on and held onto Victoria's shoulder as I stepped into them. 

She was right; they were the wrong color for the dress, and the hosiery was the wrong color. They would need a nude or a matching purple. They are so high but very comfy. I'd love to wear these.

We fooled around a little more and had an early night and lots of dirty clothes the following morning. 

Victoria and I got up at the same time. I dressed casually in a skirt and blouse. Naturally, I put on a wig and light makeup. 

I added a pair of heels and went to make breakfast. Victoria had to go out, and I had a couple of hours to myself. It gave me the chance to do some housework, some laundry, some office work, and check our finances. 

I decided to do some advance dinner preparation, but before doing so, I decided to slip on the new purple shoes. The black tights that I was wearing would never do, so I switched them for a pair of nude gloss hold-up stockings. 

The extra height of the heels made my legs look good, although they stretched my calves, and I knew that it would take a little time for my walking to adjust. I went to the kitchen, made a start, and chilled a little wine. 

About half an hour later, Victoria arrived home. She had several bags of groceries, which I instructed her to unpack while she went to change. I handed her a glass of wine when she returned, and she sat on one of the stools. It was then that she noticed the new heels. 

"Aah, I see that you have the new heels. They make your legs look terrific and very sexy. Can you walk in them?

Yes, but I will need a little practice." We chatted about lots of things before having dinner and heading to watch some TV. I wore the new heels for most of Saturday with various outfits, but they only actually went with the black clothing that I had. The heels were surprisingly easy to master, and they did make my legs look good. On Sunday, I wore the red jumpsuit. 

Naturally, I wore appropriate underwear and tights, and my red heels. I wore the blonde wig and did my makeup fairly lightly. When I checked the mirror, I looked great and, oh, so feminine. I was amazed that I could be wearing trousers, but there was nothing masculine about the look whatsoever. I liked it. 

As I was checking myself out, I realized that I was spending more of my time in a skirt than trousers, and this outfit might tip that back. Victoria was astonished at the look. 

"You are actually beautiful in that, even though I cannot see your legs. No one would know that you weren't a girl looking like that. 

Well, that is not something that we are going to test," was my response. We had a fairly quiet day. We both did some work, and we had several sessions of love-making. After that last one, I slipped on a robe over my underwear but kept the heels on and went to make dinner. 

We sat watching TV, and I noticed Victoria checking out my legs. I could also see her deep in thought, and after a few moments, she said, You once mentioned buying me some ballet boots. Perhaps we should get you a pair if you like heels that much." I did not say anything. 

About half an hour later, Victoria looked at me and asked, "I really need you; I really need your tongue. Please get me off again." 

I was happy to sit on the floor at the edge of the bed in front of her and run my tongue up her thigh. As I was doing my work, she had her hands on top of my head, stroking and touching me. What she said next made me gasp. 

"I would like to buy you a pair of ballet boots if you would like. They are not cheap and would take some getting used to, but they might be sexy. 

As long as you promise to make every effort to walk in them, although I know they might be sexy,. 

As long as you promise to make every effort to walk in them, although I know it will take time, I suggest that you think about it because the deal will be that you make every effort to walk in them and, in fact, to wear them for a whole weekend. If you don't succeed, I will burn every item of feminine clothing that you have and lock your cock away for months. 

It did not really take me any time to think about it. I had turned a corner. I would like to try the heels, and if I did not succeed, it would not be because of a lack of effort on my part. Either that or a broken limb. 

"Okay, I agree." 

"Wo That was quick; are you sure? I paused with what I was doing to answer, "Yes," before getting back to work. you are doing, and the thought of that is really making me horny. 

If you succeed and let me take you somewhere wearing them, I will get my nipples pierced.

That blew me away. Pierced nipples would be so erotic, but the thought of having to wear the boots outside made me shudder. And with that, Victoria shuddered for the first time, but not the last time that evening. 

Chapter 36: Next Morning.

I woke up in the morning to find the other side of the bed empty. 

I was trying to work out why I was in the spare room when the door opened and there stood a tousled but beautiful girl in a T-shirt holding a mug of tea. 

"Good morning. Thanks for holding me last night. I needed someone. I'm sorry for behaving like that."

"Hello to you. Thanks for the tea. You don't need to apologize; you behaved impeccably, and so did I.

I understand, and let's face it, if I were that sort of person, I could brag about having slept with the second-most beautiful girl in the world. "We just' together, but most people would believe that I was implying more than that if I told them."

"Thank you for the compliment. I won't tell anyone, not Victoria. I don't want to get you in trouble."

"You won't get me in trouble. I will tell Victoria and be honest about it. 

We do not have secrets." We both got dressed and set off to work. I didn't see Jess after we got to the salon. That evening, I was dressed in exercise gear and on the treadmill when Victoria called me. 

"Hi darling, what are you up to? I stopped exercising and sat down." I was getting some exercise. What on earth are you exercising?

Yes, I thought it would be a good idea. I have also been practicing with the boots. How are you? 

I'm good; work is going well. Gina and I are having long talks, making a few jokes, and sorting out the world. What about you? How was dinner last night? 

I'm good; work is just the same. Dinner was great, and we had a good time last night. 

You would have seen the photo that I sent. Jess looked a million dollars. Yes, she did, and you looked pretty good yourself. 

Victoria. I have something to tell you. I then told her what happened in the pub and when we got back home, the fact that Jess stayed the night, and how we"slept. 

"Nothing happened, honestly. 

I know all about it, and it is okay." I was stunned. What did she know and how? 

"What?"

"Jess sent me a text message this morning soon after she got to work and asked if she could call me later in the day. 

I was a bit worried, but I was so busy that I did not have time to speak to her until lunchtime. 

She called me and told me about the evening, her being upset, and how you held her, comforted her, and all of the rest. She says that you were a wonderful big brother and that I was lucky."

"Nothing happened, I promise you."

"I believe you both. I knew that you would tell me anyway about anything that had happened, but she was embarrassed and wanted to speak to me about it to apologize. She also told me, You think that is the second most beautiful girl in the world."

"Yes, I did say that."

"Be careful how you answer this question.  Who is at the at the top of that list?"

"You, of course."

"Good answer" We chatted for a few more minutes before we ended the call. I got back to exercising. Half an hour later, the phone rang again. This time it was Jess. 

She told me about her conversation with Victoria and also that Victoria had spoken to her a few minutes ago to report back on our conversation.

"Chris, I will never do or say anything to or with you that I would not tell Victoria about. I value you too much for that."

"Okay, that is good."

"I have a date on Saturday."

"Oh, well, that is good. Who, or is that a secret?"

"A girl that I met through college. She is a couple of years older than me and very sexy. We are going out to a pub and then a dance."

"That's great."

"I do need a favor."

"Okay," I replied, but I was a bit apprehensive. "

Could I come and change at your place so my dad does not know? I will tell him that I am going to your house, but not the other way around.  I know it's a lie, but there is no other way around it."

"Well, if you come here to change, it is not a total lie. Okay, I will cover for you."

"Thanks for that."

"Melissa will expect you for lunch on Sunday with a report."

"Okay." On Friday, I got home early and changed right away into ballet boots and exercise gear. I slogged away for a long time on the treadmill. By the time I went to bed and removed the boots, I had worn them for 7 hours continuously and walked for miles, including an hour, without a break. 

I was confident that I could manage almost anything in them. 

On Saturday, I dressed as Chris, as I had a few errands to run and lots of things to catch up on in the house. Jessica texted me in the mid-afternoon to ask if she could come over to change. 

She arrived half an hour later. 

We sat and chatted and had tea before she went to change. I was heading for my bedroom and had just about reached the bathroom when she emerged. I gasped, and she jumped in surprise. 

Then it was my turn to be surprised. 

As she jumped, she dropped the towel that she had wrapped around herself. She blushed and went to pick it up, and as she stood upholding the towel in her hand, she smiled at me and said, "No secrets between us." 

She stood for ten or fifteen seconds, naked, then turned away. I went to my room and sat on the bed. Several minutes later, and somewhat bewildered by that event, I knocked on the bedroom door and asked, "Are you decent? Do you need anything?

Come in. It is your house, and you just saw me naked; what else are you likely to see? I went in and saw that she did actually have some clothes on." Just chat with me while I get ready. 

I don't have anyone to talk to at home or at work; it's just about work or stupid gossip. I love to chat with you; you know that. 

We did talk about all sorts of things. I watched, mesmerized, as she got ready. It was amazing how she could be a plain girl at work and then go to school naked and transform into a radiant, beautiful, sophisticated young lady. 

A taxi arrived to collect her for her date, and she grabbed her bag with her change of clothes. 

Leave the bag and come back here. You can spend the night and tell Meal about your big date. If you are after midnight, I may well be asleep, but please wake me. There is a spare key on the hall table; please take it with you. Have a good time. It was 2 a.m. when Jess opened my bedroom door. 

"It's just me. I'm home safe. I'll tell you all about it in the morning." 

I looked at her. She looked bedraggled, but in a good way, and she looked happy. 

She was home safe, and that was all that mattered. I was up just before 10 a.m. 

After a shower, I pulled on a housecoat and went to the kitchen to make coffee. Ten minutes later, a sleepy-looking girl with tousled hair made it to the kitchen in an oversized T-shirt that I had left for her. 

She was decent, but she looked so sexy and a little bashful. 

"Hangover?" I asked. 

"No. I only had two alcoholic drinks. 

We had a great time and danced for hours. Then we ended up snogging, and Mary invited me back to her flat." 

She looked slightly embarrassed.

There is no need for details. What you do is your business.

Chris, I do not have any secrets from you anymore. You have seen me at low points and naked. I know your secrets, remember. We kissed and ended up in bed together. It was great. I am no longer a lesbian virgin, and I know that I love girls and not boys. 

I decided that staying the night was not a good idea, so I left to get a taxi home. She flushed. "I meant to hear." I laughed. 

"Well, it meant that your big brother was not worried about you. I loved the 'home' slip. 

But mostly, I am delighted that you had a good time and that you have a better idea about what your future holds. Do you think that I'm a slut, having sex on a first date?"No. What you choose to do is up to you. 

It is no one else's business, and you do not need my approval or disapproval. But I will say this as your 'big brother' and someone who loves you: please stay safe.

She looked shocked, but I wasn't sure why. "You love me? 

Yes, I love you very much. As a big brother and a friend.

We both laughed, had some toast, and chatted for about an hour. Jess decided that she needed to go home and see her. "Are you going to get dressed?" she asked. "Yes. I was puzzled.

No, what I meant was, are you going to dress as Melissa? After you have left, I will get dressed, and I am going to work out."Can I do your hair and make-up, please? 

We both headed for the bedrooms. Ten minutes later, Jess knocked on my door and waited. When she came in, her mouth dropped open. 

I was wearing the black wig and the purple exercise kit, including the trainers. 

"Wow, for someone about to exercise, you look really good. 

For a guy.

No for a girl. 

Now let me enhance that a little with some makeup.  e-up.   should never go to the gym without it. With all those guys drooling, a girl has to look her best. 

I'm not going to the gym; I have a treadmill, and I don't want guys to be kidding. She left half an hour later, and I have to say that I looked good. 

I snapped a selfie to show to Victoria at some point, then changed into the ballet boots. I spent a long time on the treadmill and was confident in the boots. 

In mid-afternoon, I changed into some casual clothes, checked my hair and makeup, and started dinner.