Are You Trying Turning Me Into A Sissy

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Chapter 27 - Wednesday.

I was up early and dressed in the new corset which did wonders for my figure and pushed up the breasts.  I was getting used to its constriction.  I put on the new blouse with frills and the skater skirt as well as the T-strap shoes.  

Make-up completed and the new long black wig on I looked good.  I really liked this length of hair, my own was getting longer but was an awful color, perhaps I should have my this color or maybe red.  What was I thinking?  Victoria was impressed when she found me in the kitchen. 

 "That is a good look it suits you.  You are getting good at make-up too."  I worked hard all morning, only stopping for a cup of coffee at lunchtime, I accomplished a lot of work and was ahead of my task list.  

I set about the adjustments for the gaming software and sent them away.  That should help with income.  

Then the doorbell rang.  I initially gave it no thought and got up to head in that direction when of course I realised how I was dressed.  

I stopped in the hall and looked at myself in the mirror.  

Could it be a delivery and could I get away with how I was dressed?  

I chanced to open the door just enough to peer around it and see that it was a parcel for Victoria.  

The delivery man never gave me a second look.  

I signed and took the parcel in. I went to the kitchen and was making a mug of tea when the doorbell went again.  

This time I went straight to the door assuming that it was the delivery man.  I pulled the door part open and there was Jess partly turned away from the door.  

As Jess heard it open she turned back and saw me, well the minimal amount that you could see with the door only half open.  

She started to say "Hi Chris " and came to a halt.  Her eyes went wide and her mouth opened but nothing more came out.  

I don't know what I was thinking but I tried to shut the door at which Jess said: "It's too late now, I've seen you so you may as well open the door and let me in."  

I opened the door with my eyes down and humiliation mounting rapidly.  I turned and walked into the kitchen and Jess followed. 

"I see that you are making tea, I take mine with a little milk as you know."

 And she sat on one of the kitchen stools.  

"What are you doing here?" 

I asked still not able to look at her.  

I made the tea and also sat down.  

"I was heading to a shop nearby and Julie asked to bring you some paperwork and ask you for a copy of a document she needs that you have. So here I am, and here are the papers.  Now what is happening with you?" 

 "I am so embarrassed and humiliated.  I never wanted anyone to see me like this."  

"What nonsense.  

You and Victoria clearly like to play and I suspect she encourages you, although I'm not sure how much actual encouragement you need.  

You look great by the way. Stylish and very feminine. Actually, your mannerisms, the way you walk, sit, straighten your skirt, and are very feminine and are actually really quite attractive." 

 "Thank you.  Yes, we both like to play and this was meant to be private." 

"Victoria made you show me the pictures and even you have told me some of it.  

Clearly, it has gone much further.  

You are wearing a corset, have long nails, some everyday clothes, great makeup, and the nose chain is something else.  I love the look.  

You dress like this because you like it.  At some point, you are going to have to go out dressed or someone is going to find out.  

Just like this.  I'm glad it's me.  

I like you and Victoria, you have been very kind and supportive to me.  I would never tell anyone about this. 

 I promised you that when you showed me those pictures and I will keep that promise, but at some point I won't have to because you will have to." 

 "Thank you for that.  I trust you and really like you." 

"Okay, now I need to see what is in your wardrobe."  

As humiliating as it was I enjoyed the half hour that Jess and I talked about clothes and makeup.  

As she was about to leave she said: "I have just one question?  Are those real?" and pointed to my breasts.  

I went red. 

 "No they are breast forms and they are glued on."  

"They suit you.  Maybe you should get your own pair."  

I was stunned.  

"But how would I manage with them?" 

 "Women all have them and the way you are dressed, you look like one. I have to get back now.  See you on Monday."    

I had pizzas ready to go in the oven and a bottle of wine open when Victoria came in.  I was sitting on the kitchen stool where I had been almost continuously since Jess had left.  

It was clear that the wine in front of me was not my first glass.  

Victoria took one look at me and realized that I was upset.  

"Come on pour me a glass and bring them both through to the lounge."

 She dropped her bags in the hall, stepped out of her heels, and sat on the couch tucking her legs beneath her.  

"So what happened?" 

I explained everything and she burst out laughing.  

"Oh my darling you must have been so embarrassed"  "I was but Jess was great about it." 

 "Of course she was she likes you and it isn't as if she had no idea about your dressing.  See it has happened and the world is still turning. Put pizzas in the oven whilst I change."  

We spoke about it the whole evening.  Victoria made it clear that sooner or later we were going out with me dressed and that it would be okay.  She had brought me a new present a beautiful new corset in beige. 

"Actually it is called 'nude' and it is more practical than either black or white because you can wear it with anything.  

The black would show through a light-coloured blouse and you can't wear the same one every day."  

I protested "But it's just for this week not every day although it does mean that I can alternate them."

"Of course, it's just for this week and whenever we play.  I would not expect you to wear it every day."  

"I won't be wearing it with my guy clothes."

"Oh we will see.  Tomorrow I would like you to be dressed in something very feminine, girly, whatever you like just go to town and we will have an evening devoted to each other."    

Chapter 28 - Thursday & Friday.  

When I got up the next day I dressed fairly casually so that I could get on with my work that had been interrupted the day before.  

I got lots done and by about 2.30pm knew that I had only about 2 to 3 hours of work left for the week.  I decided to leave that for the following day and went to change.  

I stripped, cleaned off the nail polish, and had a soak in a bubble bath. I spent a while thinking about my lifestyle.  I liked the clothes, the sex, the sharing with Victoria the not knowing what was around the corner. 

I also thought about the drawbacks.  Being found out would be humiliating and going out would increase that risk.  

I realized that Jess now knew and somehow that did not seem to be so bad on reflection. Victoria had threatened to take me out dressed but I dreaded it although I knew that it was coming sooner or later.  I had decided on the purple and white dress with the petticoats.  

It was very feminine perhaps a bit sissy but I wanted to impress Victoria.  I painted my fingers and toenails in a purple that matched the appliqué of the dress.  When that was dry I started on my make-up.  It was in light shades but colorful, with purple eye shadow and frosted pink lips. 

I found a pair of longish earrings with a purple stone.  I added one to my left ear lobe and managed to add the other into the same hole as the nose chain.  I added a neck chain and a couple of bracelets. 

 I used the blond wig, the first one that we had acquired for the pink 'sissy' outfit.  It looked okay, I went with the outfit but it was cheaper and nowhere near as good as the new black one.  

Next, I put on the new corset.  It was also boned and I managed to get it fairly tight before I went to make a cup of tea and put wine in the fridge to chill for later.  I went back to the bedroom and managed to tighten the corset by about another inch.  

Breathing was in shallow breaths.  Somehow I managed to put on a pair of sheer, very glossy stockings which I attached to the suspenders of the corset.  

I slipped into the nude heels that matched the stockings.  I could not help but admire my appearance in the long mirror.  I did have great legs and the corset helped the figure as did the breast forms of course.  

The outfit was lovely and very feminine but not something a normal woman would go out in unless it was something very special.  

It was not something a guy could go out in without it attracting huge attention and untold humiliation.  

It got me thinking again what if I did go out like that and people realized that I was a 'sissy' (I still had that thought in my mind) what would the consequences be afterward, assuming of course that I had not died of shame and humiliation?  Perhaps better not to think about it.

 Victoria was pleased and proud when she got home.  We enjoyed a light supper and some wine and then sat chatting.  

"I have loved coming home to you dressed this week.  I had wondered what it would be like and how I would feel about it.  

Now I know and I like it.  I think that you like it too."  

"Yes I do," I replied.  

"I had been thinking about it whilst getting ready.  

But you know that I cannot go to work dressed.  No one would want to work with me, I would be humiliated and what would your friends and work colleagues think?" 

 "I suspect that people would be more accepting that you give them credit for.  As for my friends, well they accept or not, that is their choice as it would be ours.  My work might be a little trickier to deal with but I'll worry about that if it ever happens."  

We sat in silence for about ten minutes.  

Then Victoria said, "There is a club for cross-dressers that meets once a month at a private room over a pub about twenty minutes away in Sheffield."  

I went pale and started to panic.  

"No Victoria please no I can't go out dressed, please"  

"Yes, you can.  This would be a club for men who also dress and for their partners.  They sometimes have talks or just social evenings where the members offer each other support.  

Occasionally they have a party evening, Christmas, and Halloween.  It would get us out and I'm sure that you would come to understand that you are not the only one, that the world would not end, and that you make a very feminine person.  I don't think you have any idea how convincing you look.  

Please say that we can go on Tuesday.  

With those pleading eyes, I could not agree right there and then but said that I would think about it over the weekend.  We went to bed soon after that. 

 I put on night clothes but left the corset, stockings, breasts forms (as they were attached anyway) make-up, and wig.  

Victoria was clearly feeling assertive and pushed me back on the bed.  We kissed hard.

She was also telling me how beautiful and how sexy I was and how much she loved me.  She went through how she loved my make-up, underwear, earrings, and everything else.  Of course, I could not feel any sensation from that.  

The next morning we did not mention the events of the previous night. As she was leaving Victoria said "Get dressed up nice for me again this evening.  I enjoyed last night.  Thank you and I love you very much."  

I sipped my coffee deep in thought.  Could I get my own breasts, how would that work, how could I function as a guy on a daily basis?  

Unless of course, they were small ones.  I dressed casually again and set to work.  

I got a lot done.  All of my work that paid my wages was completed. 

 I spent some time on my investments and they were going very well.  

I also checked out a number of blogs about feminization, sissies, cross-dressing, and even Tgirls. The Tgirls websites seemed to be mainly about pornography and that was not something that interested me but looking at some of them was astonishing.  They were beautiful. 

 Of course, there were plenty where it was obvious that they were guys but many of them would pass anywhere until they removed their panties.  Many had breasts, some from hormones, which made me shudder, and some from implants.  

Some of the implants did not look real but others really did.  And they were all sizes up to and including ridiculous.  Why was I looking at and even thinking about this? 

 I knew why, soon I was going to want them and I was certain that Victoria felt the same way.  I shuddered and turned off my computer.  I took my time dressing again and this time put on the 1950s style black and white dress with the black corset, stockings, the newest black wig, and black patent heels.  I felt great. 

 Victoria had sent a text to say that she was ordering Chinese takeaway for delivery at 7pm so no need to prepare anything.  I opened a bottle of white wine and sat reading.  Victoria arrived home at about 5.30pm and checked my outfit.  She approved and went to change.  She reappeared in a flared black skirt, and soft white sweater but also had on hosiery and a pair of low black heels.  

"I thought that I needed to stay smart given your outfit.  That look suits you, even with the nose chain.  Perhaps we need to check out similar outfits."  We chatted about the day and what we might do over the weekend.  Then the doorbell rang.  I checked my watch it was only 6.25pm.  "A bit early, I thought that you said 7" 

"I did say 7pm but I told our guest 6.30pm.  Right on time."  

"Guest?" I stuttered.  

"What guest?" 

In a very forceful tone, Victoria said "Go and answer the door.  I promised that I was going to push and this is a part of it.  It will be okay, I will not expose you.  Just go. Now."  

With that, trembling, I headed to the door dreading what I might find. I thought about running and refusing Victoria but realized that she probably knew what was for the best even if I was terrified.  I pulled open the door just a few inches and saw Jess standing there with a bottle of wine and a big smile.  

"We meet again Melissa.  Are you going to let me in again?" 

 I pulled open the door and she walked right in, up to Victoria, and handed her the wine.  

"Thank you for inviting me.  I feel very honored and I must say that 'she' looks beautiful, although I need to have a more detailed look of course. I hope that the wine is okay."  

I stood open mouthed at what had happened and then took in Jess.  Gone was the apprentice hairdresser and here was a stunning young woman, with a close-fitting blouse that showed off a nice, tasteful, cleavage, a short skirt, very short and high heels, very high heels, and endless legs. 

Her hair was no longer the brown with highlights that she had over the last few weeks.  Tonight it was red, very red, not natural, just red!  

I was stunned.  I thought that I knew her well but I had no idea that she looked like this when done up.  At work, she was very plain, clearly not the case this evening.   

"Perfect timing, lovely wine although you didn't have to. May I say that you look gorgeous, a bit of a change from the salon?"  

"Well after meeting Melissa the other day I felt that I had to up my game.  I rarely get dressed up.  My father disapproves of me looking glamorous, of fancy clothes, or even me going out in the evenings.  

I decided to change and get ready at the salon and come here directly.  I got one of the girls to do my hair color at lunchtime." 

 "You look stunning and the hair is certainly dramatic and going to get your attention. But come and sit down."  

Said Victoria.  We moved into the lounge and I sat at one end of the couch with Jess at the opposite end and Victoria on a single seat.  I was speechless, about Victoria inviting Jess and how Jess looked.  

"My Dad is going to go crazy.  I am out and he does not know where and he will not approve of the clothes or the hair.  He is a bit controlling."

  Victoria said, "I seem to recall that when you had been talking to Chris, I mean Missy, gets confusing sometimes, that you had mentioned that your Dad was quite strict with you."  

"Yes.  Since my Mum died eight years ago he has been lost, afraid for me, not really wanting me to grow up.  He did not want me to go to college or become a hairdresser.  

It took me all of my time to persuade him otherwise." 

 "But why?"  

"He wanted me to stay home and run after him.  Sooner or later he is going to get fired because he is often late for work, takes sick days, and frankly drinks far too much.  We don't really get along and I try to avoid him whenever I can.  The only male that I know and who treats me like a proper grown-up is Chris."  

For the first time since Jess arrived, I spluttered, "Male."  Both of them turned and looked at me and Jess said: "Oh I'm sorry but you know what I mean.  

You have been so nice to me since we first met and I value our conversations.  I wish that you were my brother."  Victoria also laughed "So you don't have a crush on him?  I know from Julie that you have a crush on someone."  

Jess blushed from head to toe and hung her head almost in tears. Victoria realized that she had said something to upset Jess and went to sit beside her.  She placed her hand under Jess's chin and said, "I'm so sorry Jess I did not mean to pry or to upset you. 

 What is wrong?  You are with friends.  Please tell us?"  You could see her summoning up the courage to speak. She took a deep breath "Please promise me that you will not share anything that I tell you with anyone else and that you will not be angry with me." 

 "Why would we be angry?  Of course, whatever you choose to tell us will remain between us.  After all, we have a few things that we would not like to be known about don't we?"  

"Okay. I have been out with a few boys, mainly behind my dad's back, but somehow it does not seem right.  I also seem to be more attracted to girls and one night I snogged a girl and it was great but I realized that for her it was just too much drink and a bit of a lark.  

I think I may be gay and of course, that would not go down well with Dad.  He hates anything vaguely gay or as he puts it 'poofters'.  Actually, he has a few other names as well." 

 "Wow.  That took some guts to share that with us and I promise that we will keep your secret and if there is some way that we can help you, the two of us, we will.  As for being angry, given our lifestyle that is unlikely."  

"Okay, now here comes the hard bit and the bit that might make you angry.  My crush." 

 "Yes, I'm guessing it's a girl but you don't have to tell us.  It's okay," soothed Victoria.  "You have shared a lot with me and been very kind, both of you, so it would be almost like lying if I chose not to tell you but I am nervous." 

 "You have no reason to be."  

"Actually I do.  It's you."  As she looked at Victoria directly. 

"Me?  But I'm not gay and I only know you from the salon and because Chris talks kindly about you."  

Jess took a deep breath.  

"I know that you are not gay, well I had no reason to believe that you were.  But I met you soon after I started working with Julie and you came in to get your hair done regularly and of course, you came in from time to time to see Julie and occasionally to see Chris.  I developed a crush, it's like a silly schoolgirl having a crush on a teacher." 

She took a deep breath and carried on.  

"You appear so confident, are successful at your job, always beautifully dressed and you are stunningly beautiful.  It so happens that you are always thoughtful to the staff and very kind.  It's embarrassing I'm so sorry."  

Victoria put her arm around Jess's shoulders.  

"Jess I am so sorry to have put pressure on you to admit that.  I wish that I could take it back.  But please I am not offended, slightly flattered and a bit embarrassed myself." 

 "Do you want me to go?"  

"Oh please no we don't want you to go.  Let's have a drink, something to eat, and chat and put that aside." 

The doorbell rang again and this time I just stood and went to answer it.  I was so lost in thought about what had just happened that I forgot how I was dressed.  It was the food and I had to go and get cash for a tip.  

It was not until I brought the food and plates into the lounge and saw Victoria and Jess laughing that I gave it any thought.  Now I was embarrassed.  We ate and we had a few glasses of wine. 

We talked about all sorts of things.  Victoria's job, my gaming design, and Jess's apprenticeship.  We did not mention my 'hobby'.  

The most difficult part was talking about Jess's father and how to manage that situation.  Realising that it was late we invited her to stay overnight but she said that she could not. Victoria insisted that she would call her father.

She did so and when he started to raise his voice so did Victoria.  Something must have calmed him down and he said that it would be okay.  We sat up late chatting like old friends.  

When we went to bed Victoria loaned Jess a nightdress, makeup remover, and everything that she would need before turning in.  

Victoria and I cuddled up and she whispered, "No sex tonight lover I don't think that I could with Jess here."  

"I agree.  She has had it much tougher than she let on.  I wish that there was some way that we could help her." 

 "She needs to find her own way but you can help by being the big brother that she needs.  Or perhaps big sister!"  

Chapter 29 - The Weekend.

It was 10 o'clock the next morning when Victoria woke.  She went to check on Jess who had just woken up herself.  Victoria pointed her in the right direction for a shower and loaned her some underwear, a sweater, and a pair of jeans.  I emerged wearing my skater skirt, sweater, a pair of low heels, and a black wig.  I was sitting at the dressing table as Jess walked past and saw me.  

"Hi.  Thanks for last night you were both very kind.  Not sure how my dad is going to be when I get home."  

She looked at me without make-up and then asked, "Can I do your make-up for you.  I don't get the chance to practice on others as much as I would like."  

I agreed, why not, there were very few secrets anymore.  Victoria came looking for us and found us almost finished.  She laughed when she saw what we were doing.  "Little sister doing big sister makeup."  Without thinking Jess blurted out, "I wish she was my sister.  Or brother depending on what day it is." 

 "I've got coffee and toast ready.  Then I'll get around to my make-up." 

 "Victoria, I'd love to do yours for you as well."  

The puppy dog eyes she used would have got her anything that she asked for. 

 "I'm sorry about the 'crush' and would love it if you were my big sister too." 

That made us all smile.  We had coffee and Jess did Victoria's makeup.  By the time she was finished, Victoria looked stunning.  It was a simple daytime look but she had done a few things differently from how Victoria normally did them.

 "Thank you Jess.  I am impressed.  You have a real skill there. Now I'm going to give you a lift home and you are going to introduce me to your Dad and I am going to charm him so that he does not get mad at you."  

"There is no need for that really."  

"Actually there is.  It may prove useful at some point for him to know who I am." 

When Victoria got back from taking Jess home she reported that things were okay.  "Her father is not that nice a man, had a terrible hangover, and was looking for a fight.  But I charmed him, I think.  

The house is dated but well kept and clearly Jess does a great job of keeping things clean and tidy.  She must work hard."  

"Thank you for doing that.  She is a really nice girl.  I've always liked her as you know but after last night I like her even more.  And she has great taste in women."  For that I got a cushion thrown at me.

 "She is actually really talented.  Your make-up and mine are stunning and simple.  I know that Julie rates her skills very highly as a hairdresser as well.  She also has a great way with the customers as I know from personal experience."  

"Yes, but you were getting preferential treatment."  That got a second cushion missile.    

We had a quiet weekend except for the bedroom where it was very far from quiet and where we spent a lot of time.  On Sunday evening we were lying in bed when Victoria said, "Well it's back to boy clothes tomorrow.  

Are you looking forward to it?"  

"No.  I have enjoyed it.  That nose chain was a bit annoying all the time but I got used to the clothes.  I never forgot what I was wearing but they seemed to be natural."  

"So what about Tuesday night and the club at Sheffield.  Are you up for it?"

 "Victoria.  I don't think that I can.  I lack the courage.  

"Okay.  I told you that I was going to push and this is it.  We are going, you are going to be dressed and that is final."  

The way that she said it made me realize that she had made up her mind and that there was little point in my arguing.  The next thing that she said shocked me even more. 

 "I'm going to call Jess and ask her to come with us.  It is known as a gay-friendly pub and this might help her.  I can speak to her father. Unless you would like to ask her?"  For the first time, I found courage.  

"I will speak to her at lunchtime tomorrow and see what she says."  "Well done you."