Are You Trying Turning Me Into A Sissy

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Chapter 4:  Victoria.

On Monday morning I had a meeting in a city some distance away so I set off for the station and a 90-minute journey.  

My employers prefer us to travel by rail whenever possible and they are prepared to pay for first-class travel, I suppose in the hope that we can get some work done during the journey.  I prepared for my meeting and had a coffee during the first part of the journey then I relaxed and turned my thoughts to the weekend and the last few weeks.  

I am an attractive, professional woman with a good career, making a decent salary.  I enjoyed dressing well and knew how to use my assets to my best advantage. I was coming to realize that I was actually pretty hot.  My husband is a lovely man, intelligent, very attractive, attentive, and loving.  

He is not a macho man, actually a slight build, and he has a feminine side that was part of the attraction.  However, I did not consider him to be in any way effeminate.  It puzzled me why his being dressed in women's underwear turned us both on so much but hey-ho we were enjoying it and not doing any harm.  

I have never been so sexually satisfied but I wanted it to carry on and I was enjoying taking the lead.  

We shared things and made joint decisions, he was not subservient, at least, he had not been until recently.  I know that I did not want to turn him into an effeminate man but feminising him was different.  I did not want him to change sex.  

Where was it going?  I stared out of the window for some time watching the scenery but not really taking it in.  I may even have nodded off for a minute or two. Then I sat up straight, my eyes opened wide.  Suddenly something he had said weeks ago sprang into my head: 'The day that you get me in a pair of nude 15 denier gloss tights and heels you can call me a sissy and I won't complain' at least that was what he meant.  That was it, I was going to get him to dress up as a sissy! My very own sissy! 

 I took the meeting by storm, landed a new contract, and probably earned some extra commission.  I had a wonderful husband and sex that no one should have any right to expect.  I called my office to report on the meeting and let them know I was heading straight home.  

I had just over an hour to fill before my train.  I headed for a department store opposite the railway station.  I bought some more panties, a couple of camisoles, a large supply of hosiery (no nude 15 denier glossy tights, yet) a black nightdress and robe set similar to the one Chris had worn over the weekend, and a shorter nightdress that would just cover panties.  I also found a pair of mules, bedroom mules, and seduction mules.  

The sort of thing no one would wear outside the house, in Chris's size.  When I arrived home Chris was already there making dinner preparations.  He saw the bags, raised an eyebrow questioningly but said nothing.  "Just replenishing stocks pet," I said.  

 Chapter 5:  Things moved on a little further.

I was puzzled about what the bags contained but it was clear that Victoria was not going to tell me about the contents or show me until she was ready.  

I think that I knew what the bags would contain.  More panties, hosiery, almost certainly another suspender belt, and probably a nightie or robe (or both).  A man wearing women's underwear was not something that was accepted as okay, I had thought that it was wrong, but I knew I loved the feeling of the clothes  Nothing! Nothing that evening. 

Yes, we went to bed, yes I wore knickers and hold-ups.  She wore hold-ups.  We had sex, long, lovely sex with our hosiery-covered legs sliding against each other.  After I had cum I ate her out.  

Actually, I asked her to kneel over me so that I could eat her. She seemed reluctant for a few seconds, she was not convinced that me eating my own cum was right but I asked and I know that she loved it. We went to sleep and I still had no idea what was in the bags.  

The next morning I asked her. Her reply: "Mind your own business, all in good time."

  It was the same that evening, nothing, not a hint.  Wednesday is the same, sex is great but not a hint.  I realized that it was likely to be Friday before I found out.  Worse on Thursday she claimed that she was tired and there was no sex.  How many days since that happened?  During this week of course I was wearing panties and hosiery, mainly 60 denier tights.  

I was pretty much working at my office above the salon and had very little contact with anyone else.  Jess came up to see me on her breaks a couple of times and I'm sure that she was checking to see what I was wearing.  

It was embarrassing but I suppose a man wearing tights should be embarrassed.  

On Friday evening I was home first and started the dinner.  

A chicken salad with some cold, dry white wine.  Victoria arrived about 5.30pm and it was clear that she had had a hard day.  I handed her a glass of wine.  "Darling you are an angel, I'll have some of this and then go and shower, I need to chill out.  Can dinner wait for a while?"  

"Of course, it's a salad, won't get cold!"  I sat on a kitchen stool leafing through one of Victoria's magazines. There was an article about men who wear women's clothes!  I got a few lines down when I heard Victoria coming and dropped the magazine like a hot potato.  

Why had she never told me about it, what did it say?  Then she came into the kitchen.  She was wearing her hair up and had redone her make up, heavier than she usually wore.  She was wearing a maroon basque, that had taken inches off her waist and which just supported and covered her nipples, matching panties, barely black stockings, and a pair of patent black heels that were higher than I had seen before.  Over all of that she wore a negligee that was sheer and in any case not tied.  My tongue hit the floor.  She was staggering and I stuttered that out.  "Why thank you, kind sir."  

"I wish that I had changed now." 

 She replied, "I think that would be a good idea.  Go have a shower and I will leave something for you on the bed.  Then you can stop asking what was in the bags."  I showered quickly.  

Sex was happening tonight that was obvious, but I felt that it was going to be special.  

I tried and went to bed almost trembling with anticipation.  The most beautiful nightdress with matching French panties in black silk with white embroidery pattern on the legs of the panties and on the chest of the nightdress.  There was a matching suspender belt with 6 straps and it was very deep.  A pair of very fine, black glossy stockings, a pair of black lace gloves and a pair of shoes, no heels, no. 

They were black gloss mules trimmed with a feather and had a two-inch heel, surely not?  I stared at the heels as I pulled on the other items.  The night dress came to mid-calf and had a slit to the top of the legs.  I hadn't noticed the sheer matching wrap but slipped it on and tied the belt loosely at my waist.  Then I stepped into the shoes.  

They fit, everything fitted perfectly.  I stood up straight, whoa, my weight distribution had altered and it took me a few minutes to get used to it.  Moving was tricky too.  I reached the lounge where Victoria was.  "Oh, wow, you look so sexy, my god your legs are incredible.  I love the look, do you?"  "Yes, I do. You bought all of this for me?"  

"Of course. The night dress of mine that you wore was too tight and in any case, I need it.  You needed the rest, how does it all feel?"  "It feels so sensuous, sexy. The shoes, why the shoes?"  "Remember the weekend of the dance?  

You went to the kitchen to get a drink and the next day stayed in the nightdress.  You had bare feet. That's not right and in any case, have you seen what those two inches do for your legs?"  "It's getting serious, I still feel that it's not right for a guy to wear women's clothes."

  "Look, you love it, I love it and you.  I'm sure that most people would think it's odd but they don't know and it's not as if we are going out like this."  

"You look hot, a new outfit and the shoes, I love them."  

"You looking all hot means I need to up my game or you will be sexier than me.  The shoes are something else aren't they?"  "You have always been hot and don't need much help, but yes you are sexy in that.  I love the shoes too."  "You're not jealous of the heels are you?"  "No of course not and in any case I could never stand in them."  "Don't say never, one day maybe I will get you in a pair."  

"I doubt that."  

We enjoyed a quiet meal and later snuggled on the couch.  Later on I slid down to the floor separated Victoria's legs and went to work.  I took nearly 40 minutes to bring her to climax and then we went to bed. The sex was crazy, we were at it for ages and fell asleep absolutely spent.  The rest of the weekend was spent in much the same way, lots of sex and lots of lace and nylon.  I practiced in the heels until I was comfortable.  We loved each other.    On Sunday evening Victoria and I were lounging with the TV on when she said, "I would like to make a bet."  

"Okay, on what game and what's the prize?" I replied.  "You can pick a game this week.  You can pick the consequences for me if you win." 

 "Really, any limits? Pierce your nipples?"  "Where did that come from?  Would you really want me to get my nipples pierced? Rings or barbell?"  "I saw a picture in an article in your magazine and thought it looked hot.  Rings I think."  "Wow. I would do that for you if you really wanted it although it's not something I would have chosen myself." 

 "I would not want you to do it just for me."  

"You have done lots that I have asked.  What else did you see in the magazine?"  "I saw an article about crossdressers but I did not get chance to read more than a few lines" 

 "I've read it.  Very interesting.  There are many more men wearing women's underwear and clothes than you would think.  I got a few ideas and that's why I want the bet.  I want to try something.  

I don't want to tell you what is involved, you will find it challenging and probably slightly humiliating initially but I'm sure it will take us to a new level of fun.  As for the article, I would prefer that you don't read anymore, at least for now."  

"Now I'm intrigued and a little scared.  But, don't bet, let's just assume that you won and we'll do whatever it is because I love you and trust you." 

 "You are a lovely man.  Thank you.  It will take me a week or so to get it organized."  

"Okay." 

 "Do you really want me to get my nipples pierced?" and she winced.  "Only if you want to."  

"I think that I will leave the piercing for now."   

A sissy emerges  The next two weeks passed relatively quietly as far as sexual adventures go.  We had social events, jobs around the house, and lots to keep us busy.  We had plenty of great sex.  

I wore underwear every day and a nightie several evenings.  There was a tension.  Something big was coming soon and I was a bit nervous.  Thursday at breakfast Victoria looked me in the eyes and said: "I want you to get away sharp tomorrow.  I plan on taking a half day and will be here by 4 at the latest."  

"I can get away soon after two"  

"I that case, come home take a long bubble bath, and shave, closely, everywhere!"  "Okay, what's happening?" 

 "That would be telling.  You'll see tomorrow."  

I left my office just after two and headed home for a long bubble bath. I used some of Victoria's bath oil, scented, but I guessed whatever was going to happen involved me wearing something feminine.  

When Victoria arrived she suggested some pink polish on my toes and a glass of wine to let them dry before we really got started.  I was wearing a black silk wrap and asked, "So what do you have in mind?"  

"You will need to wait and see. In a couple of hours, you will know but for part of the time when getting you ready you will be wearing a pair of glasses that will prevent you from seeing most of it until it's done."  

That made me swallow hard.  What did she intend?  "This may be difficult for you but just remember that I love you."  

In the bedroom, Victoria handed me a pair of glossy 10 denier neutral colored tights which I put on.  They were very fine and sensuous as they slid up my legs with no panties underneath.  

She handed me the pink silk panties with the lace decoration that had been amongst the first purchases that she had made several months ago.  That was followed by the matching camisole.  I got the feeling that whatever was to follow was going to be quite feminine.  With tights and underwear on Victoria started on my fingernails.  

There was lots of sanding, shaping, and then false nails.  She applied three coats of pink polish and a clear coat.  The nails were beyond the end of my fingers by over half an inch and it was clear right away that they were going to take some getting used to.  With a towel over the dressing table mirror, she started work on make-up.  I was not that surprised by this turn of events but it still showed that this was moving things to a much higher level than had been the case up until now.  Victoria plucked a small number of stray eyebrow hairs to 'tidy them up a little'.  That made me more nervous than anything to this point but she really only removed a very small number. 

"One day I'd like to give them a lot more definition," she said and I felt myself shudder.  

After the foundation came eye shadow, blusher, and mascara.  Then more mascara and the comment "Nice lashes, next time we'll add some false ones" I didn't know what to think false lashes and a 'next time.'  Lip liner followed and then she filled in the lips themselves with a very shiny pink.  

'Girly' was my only thought.  I have to admit that the feeling of the makeup was not unpleasant but the lipstick felt really nice. It was hard, very hard.  Victoria produced a pair of very feminine OTT sun glass that she slipped on "Don't want you to see any more until we are done and the big reveal" she said.  Well, I wasn't going to see anything as the lenses had been made opaque. 

 Looking down I could just see below the bottom of the frames but it wasn't worth the effort I wasn't going to get any clues about the finished me.  "I need to do your shoes now" as Victoria lifted my right foot.  

I thought it was odd for a few seconds as it was not shoes that she was fitting, but then I realized that it was some sort of short, ankle-length sock.  Then the shoe, clearly it had a heel which was obvious when the shoe was on and I put my foot back down.  It was higher than the bedroom slippers.  

A sock and shoe were added to the other foot.  Next came a pair of gloves.  I could feel that they were made of lace and fingerless, it would have been a waste to cover those nails.  

They were short, just up to the wrist, and the very little that I could see revealed that they were pink as well as everything else.  After a minute of two fiddling with something in a wrapping Victoria then came across and asked me to put my head forward.  

A wig! A wig, oh my goodness this was serious.  I don't know why it surprised me but it shook me, what also shook me was the shudder through my body.  I could feel that it was long, touching my shoulders and curly and from a couple of stay strands that fell across my face below the glasses I saw that it was blonde, really blonde! 

 It took a few minutes of adjustment to get it sitting correctly, a bit of combing, and a couple of pins to fix in place before Victoria was satisfied.  She then added a pair of clip-on earrings and they must have been quite long as they brushed my neck.  

"This is looking good and turning me on so much I could drag you to the bed, but that would just be a waste.  Please stand up."  

I rose and it took me a little time to find my balance in the higher heels. A little more rustling of paper and Victoria was beside me.  Put your hand on my shoulder and raise your right foot a bit.  She guided something (a dress?) under my foot and then told me to raise the other foot. 

 As I stood she bent down behind me and started to raise the garment up my legs.  It came up quite a long way, maybe this was just a top, but why put it on from the bottom.  

As whatever it was settled it my waist it was obvious that it was a dress but a short one as I could feel the bottom of it halfway up my thighs. 

 "Bring your arms forward," said Victoria as she guided my hands into the sleeves.  It was silky and had lots of lace.  

She moved behind as she pulled the garment up and adjusted it at my throat, it had a collar that stood up slightly and was close fitting, but not tight at the throat. She pulled up the zipper and adjusted a fastener at the back of the neck.  

She stepped back and moved around adjusting the garment which was obviously a dress and which I could see, even from my restricted view was also pink.  No surprise really.  

I was trembling and realized I could not wait to see the result.  Victoria whispered, "I think that is amazing, I am so pleased and I love you so much. 

 Take a couple of steps this way towards the mirror and I'll remove the glasses so that you can see.  Before I do I warn you that you may find this a bit difficult."  

"What do you mean?" I stuttered.  

"Well, you'll see in a second."  

And she removed the glasses and stood to one side.  I blinked for a second then looked, I was puzzled and looked at Victoria and then back to the image in the mirror.  I had wondered where the hell I was, I had not realized for a second or two that the person in front of me was me. It was a girl, not me!  

It was me, oh it was me. I uttered the immortal words.  

"I'm a sissy!  You've made me a sissy!"  I shook as I said it.  I was angry, well for two seconds, then I was aroused, then I blushed, then I started to swoon and Victoria sat me on the end of our bed.  There was concern all over her face 

"Are you okay?  I warned that it would be a shock."  

"Sissy," was all that I could say.  

"I want to have another look," I said as I stood up.  I started at the top.  Blonde shoulder-length curls. 

 A pink silky dress with lots of lace, lots of lace, that fit close about the throat, short sleeves in lace and it finished mid-thigh with a skirt that flared, a lot, because of the amount of fabric in it.  Lace, pink fingerless gloves with pink talons.  

Shiny, shiny legs ended with pink lacy ankle socks that had a frill and patent pink peep toe court shoes with a three-inch heel and a huge bow on the side.  I realized that had a small platform as well.  

As I worked my way back up I checked my face.  I looked good, I looked different, I looked girly, I looked pretty, how could I look pretty I'm a guy?  

Well, I did not look much like a guy.  Then something clicked - glossy tights and high heels.  I remembered saying that months ago, I could not recall exactly why but I recall it.  

"I'm a sissy."  

Victoria had been quiet whilst she watched me examining myself.  "Yes, my sissy. 

Come on let's go downstairs, get a glass of wine, and talk. I'll explain" I blushed red everywhere.  

We sat in the lounge, me on the couch and Victoria on a footstool in front of me.  She was looking me directly in the face.  I, on the other hand, was embarrassed, slightly ashamed and it was difficult to look at her directly for any length of time.  

"I told you that you would find this challenging and I see that it is. I always regretted calling you a sissy because I saw that it hurt you. The day that you wore tights for the first time you were the one who made the comment about glossy tights and heels and calling yourself a sissy.  

I swore to myself that day that I would never call you that again unless you said it. But I never forgot what you said."  

"I loved what we were doing and have done since then.  I am so proud of you and your openness and willingness to experiment.  I know that you sometimes think that it is wrong, or taboo.  

But I like it, I love our games, I love what you wear and I love the outcomes, especially in the bedroom."  

"The weekend that we went to the dinner you agreed to shave and wear stockings I was impressed and loved it.  

I loved what we did that night and the fact that you slipped on my robe.  I knew then that I loved you so much, that I loved seeing you in those clothes, and that you loved the feelings they gave you." 

 "When I was on the train the Monday morning after that I was reflecting on our weekend and how much I had enjoyed it when your statement popped into my head.  I decided then that I was going to get you some more items, nighties, robes, heels, and stuff because we would both enjoy it. I also decided that I was going to dress you like this, not the exact outfit but a sissy outfit."  

"Please don't cry.  You said that you were a 'sissy' although I knew that you would.  It is what I wanted and I knew that there would have to be this conversation."  

"I'm sorry but this is humiliating.  You married a man, I was never macho but not a sissy," I replied as tears continued to roll down my cheeks.  

"I knew that you would have a degree of humiliation and we spoke about it and the fact that I wanted to push you and you agreed.  I loved you and still love you.  

No, you were never a macho man but that was not what I wanted.  I loved you for you, your sensitivity appealed to me.  This is, and everything else is, between us and no one else.  I was not going to take you out or invite people over to laugh at you. When you saw yourself dressed as you are, you did not run off or pull the clothes off or tell me that you hated it did you?"  

"No, I suppose not," I replied.  

"Now, let me ask you a couple of questions. Do you enjoy the feel of the clothes?"  

"Yes, I do." 

 "Do you enjoy the feel of the makeup?"  

"Yes."  

"Do you think that you looked pretty?  

Remember that when you first looked you did not realize, for a second or two, that it was you." 

 "Yes."  

I felt so embarrassed admitting this.  

"Are you aroused?"  

Oh my, I don't think that I realized how aroused I was. 

"Yes," I admitted shamefacedly.  

"I knew that and I'm dripping wet as well. I would like you to wear that outfit until Sunday evening, except in bed and I've got nighties for that.  Then on Sunday evening we will remove everything and chat about it. 

 I know you will struggle but go with me and on Sunday evening if you decide this is too much we don't have to do anything like it again. Okay?" 

 "Okay." 

 "Now, I have some snacks, some more wine then we'll have an early night and tomorrow you can practice in those heels, you walk like a gunslinger!"  

With that, she reached over and kissed me.  

"Now let's fix the makeup and get the wine." 

 We cuddled for the rest of the evening with some music on in the background.  We did not say much to each other or any consequence.  We talked about the makeup and the clothes and where Victoria had purchased them.  

I was aware that we were both turned on and I slipped onto the floor, pushed her knees apart, slipped down her panties, and savored her for a long time.  She was ecstatically clutching the arms of the chair as she came several times.  After a period of recuperation, we went to bed.  

"Remove the dress, panties, and shoes then slip this on" as she handed me a pink silk baby doll that was not long enough to cover any of my boy bits.  

She stripped and came back from the bathroom wearing but a pair of pink glittery hold-up stockings for just a moment I was jealous. She pushed me back onto the bed, leaving me lying back she slipped over the top swallowed me inside her, and rode me energetically.  

I saw her smile down at me still fully made up and bewigged.  We made love, for quite a time.  

 Clearly, she wanted me to clean her up and so I did relishing her love.  We fell asleep soon after.