Crossdressing, Why Me? Ch. 04

Please bear with me whilst I set the scene, preamble and continue to detail my development. I hope you find them interesting and can relate to them. The "juicy bits" come later. The story I relate is once again based on experiences I honestly have had. I cannot promise the words spoken are exactly true though.

Even as I write my history I still question why I cross dress. One thought has come to me. I partially blame my mother. She already had my older brother, so she wanted a daughter. He was always her favourite, I never matched up. I lost count how many times she told me she didn't want another that I should have been female. Consequently I never truly felt as loved as I felt I should have been.

Looking back at early photos of me I had long hair, too long. She used to spend ages with me sitting next to her so she could brush it. Hours we spent like that over the years. Mind you I remember I enjoyed the attention. Even some of my clothes were a bit girly. Don't get me wrong I love wearing female underwear and outer clothes but I wonder if this is where it all started. If so thanks mum, I love it. It is an issue at times but mostly a true delight.

If you have read my previous reminiscences you will know that I had acquired a comprehensive range of lingerie. I wore it whenever I could, and still do, whether alone or sometimes under my man clothes to work. However, lingerie is called underwear for a reason. Usually in my flat it was all I was wearing because other than a satin housecoat I had nothing to wear over my lingerie.

I also had experienced some great and varied sex whilst wearing lingerie, as you may have already read, but I wanted more.

I also had quite a few sexual experiences where the women were totally unaware of the other me, my alter ego. I was always jealous though of what they were wearing. I wanted some of it.

The time had come when I wanted a female wardrobe. I needed some clothes to wear on top of my underwear. I wanted dresses, skirts, tops and blouses. I also had a burning desire for heels, tall sexy looking high heeled shoes and boots. I thought if only I could get the right clothes, and look convincing enough, I could go out fully en femme. If I could pass as female it would open a whole new way of life.

I feel sorry for well built or tall guys that want to cross dress. For them it must be so difficult to dress without being stared at outdoors as with those that are dark haired and need to shave often. Large feet and hands must make it difficult to pass as female too.

I knew what size in lingerie I liked to wear but back then I wasn't sure what outer clothing size to buy. I now know I am UK size 12 (USA 8) but love fitting in to a size 10 (USA 6) especially in panties. They hold me in beautifully. My statistics are 36" 30" 37" and only 5'6" tall. I am petite with small hands and feet which helps me pass.

At that time though I did not have a clue about sizing's so how did I go about buying clothes? I could barely walk in to a department store and explain I wanted female clothing for myself.

One day I had an idea. I would go to a charity shop that sold female clothes and say I was going to a party in drag. I thought that would be both credible and if it was the wrong fit the mistake would be inexpensive.

I went the next day to an Oxfam charity shop that sold second hand clothes. I found a middle aged sweet lady to help me. I explained what I wanted and why. She was totally unphased and told me it was surprising how many guys went in to buy women's clothing for themselves. She was marvelous, so helpful, giving me more assistance than she realised which was to stand me in good stead for the future.

What I wanted was a couple of choices of nice things. I wanted nothing slutty. I wanted nothing outstanding, things that wouldn't make me stand out. I wanted to be able to blend in and not stand out.

With her assistance I selected a pretty yellow dress with tiny flowers on it. It had short sleeves and the hemline was not too short. It was a size 12. It was lovely, so soft, lightweight and flimsy. Since the shop was empty she suggested I should pop in the cubicle and try it on. I never expected that. It fit like a glove. I loved it. It was the first time I had worn a dress since my Aunt Susan moved out. I was even wearing knickers (panties) which helped me enjoy the occasion.

I returned back in to the shopping area with what would be my dress, and now I knew the size I wanted, I looked for more items.

I found a dark grey pin striped tight fitting pencil line skirt in my size and a silky red button through blouse. I also found a black jacket that I could wear with both the dress or skirt.

I had selected my items with great care that first time. I wanted to fully experience and appreciate wearing female clothing of the most sensual fabrics and colours. Men's clothes are rough, bland and boring in colours and fabrics. Women get a greater choice and must get the best feelings within themselves whilst wearing their clothing. I wanted to experience those feelings.

Having paid a measly sum for my items I went off in search of completing my ensemble.

Next on my shopping list was shoes. I had already discovered that women's shoe size is one, or maybe one and a half, bigger than a man's. I longed for shoes with heels to enhance the totally femme feeling. I went in a shoe shop and made out that I was looking for my girl friend. I found some open toed ones in case they were a little small with a manageable three inch heel.

Excitedly, having finished my shop, I hurried home to try everything on in the comfort of my flat. I slipped in to sexy lingerie and put on my dress and for the first time ever, high heels! As we all know they take a bit of getting used to, but I quickly mastered them, and strutted round my flat. I stared at my transformation in the mirror, pleased with what I saw, my legs appeared so different because of my heels.

Dressed fully feminine now made me even more eager for company that would accept me for who I was. Before that could happen though I needed a wig and some make up. That was my task for the next shopping trip.

I went to Debenhams, a department store, where you can shop anonymously to purchase a make up set. It was complete with everything an aspiring girl might want but hell, not cheap!

Next I needed a wig and I knew of a shop in the town centre I had spotted. I had been past a few times and looked longingly through the window at their range. I apprehensively went in. A guy served me. I used the same excuse as before about going drag to a party. I took so long over selecting one I think he saw through my excuse. Anyway I settled for a shoulder length dark one. I almost ran home to change in to femme mode and put it on.

I ripped my clothes off and slipped on some of the sexiest lingerie I possessed. Then I pulled my sheer dress on over my head and stepped in to my heels. I sat in front of my mirror for ages applying make up for the first time, trying to do the best job I could. I felt like a teenage girl dressed sexily and wearing make up for the first time. After a while I was fairly pleased with the result. I certainly was after applying my lipstick! I was truly enjoying the feelings of how it felt to be a woman.

Finally I put my long haired wig on. Great, I felt great! I sat there just brushing my long beautiful hair for quite a while. I truly felt so female, except for my stiffening clitty, that is.

The next thing I did was switch my computer on and get to my favourite chatroom. On went the webcam and then for the first time I was public as dressed fully female.

Even though I was only on line I really enjoyed myself. I was with others like me, that appreciated me, dressed in my finery. I had a long conversation with a lovely CD called Michelle which ended up with me and her having a nice mutual slow and languid wank on cam as we chatted. This was good but I really wanted more. I wanted to go out dressed as a woman and then for it to lead to sex.

On Monday I was to drive a couple of hours up north to a business seminar to be held in a hotel. This presented me with an opportunity to take my new wardrobe out of doors. I had no plans except to be somewhere outdoors, other than in my flat, dressed en femme. I packed my new skirt, top, shoes and jacket along with some lingerie, false tits and make up in my car the night before.

The day dragged. I don't think I paid too much attention, my mind was full of later. Then my day finally finished. I hung around so I was one of the last to leave. I went to my car and grabbed my bag of girly bits. I returned indoors and went to the toilets. When the coast was clear I stole in to the ladies. Here to all intense and purposes I changed sex. I felt I had to be careful and quiet especially as a couple of women came in to the next cubicle for a pee.

I spent ages in there dressing and putting on my wig and make up. My heart was thumping. I was nervous going out en femme for the very first time. I had no where to go, nobody to see, just a long drive home but I was excited. I was also sexually aroused but any relief would have to wait.

When the bathroom was empty I sneaked out carrying my holdall containing my male clothing. As I was leaving out a side door to get in my car a guy appeared and held the door open for me. I smiled at him, if only he knew, and went off to find my car.

I felt exhilarated. In a strange way I felt free. Even though I was only to drive home dressed in female attire I was loving the experience. I stopped at traffic lights and was looked at by guys in the next car, smiled at, even winked at by one guy. They didn't appear to realise I was a guy. I was passing as female and truly loving it. I was openly ogled at by a horny truck driver so I blew him a kiss and smiled.

I got stuck in a traffic jam on the motorway home and as we crept along I felt I was being scrutinised by many other drivers. I know we all look into other's cars in traffic. I do. I look to see who they are and how fit and sexy the women look. I was experiencing it from the other viewpoint now and I loved it.

About half way through my journey, I had a full bladder, I needed to pee badly. Now this was going to be a test. I looked for some services, found some, and pulled in. I checked myself in my mirror (as many women do) and feeling that I was as convincing as I was going to be got out my car.

I went inside realising I needed the ladies not the gents. It was a proper pleasure to walk in there, find a cubicle, and do something simple like sit down in a skirt and have a pee. I went out to the washbasins, washed my hands, then left avoiding eye contact with the women. They were intent on what they were doing anyway and just ignored me.

Test passed. I was getting away with being en femme in public. I felt truly liberated. With a spring in my step I returned to my car. I realised though that I had overlooked not purchasing a handbag (purse). This was something I must put right as every woman goes everywhere with one.

The remainder of my journey home passed uneventfully except the broad grin I had on my face for two hundred miles. Stupidly I hadn't thought about how I might get in my flat without passing my neighbours. I had nowhere to change back into boring so seeings as it was after dark, I risked it. I got in undetected having had a lovely evening outside en femme. The trouble was now it was a need, more than a desire, it was to be part of me.

I slept dreaming contentedly that night in a sexy sheer satin nightie after masturbating with my favourite friends in a chatroom. In the morning as I readied for work I planned my evening. I thought to take a walk from work dressed as Suzie would be fun and more safe than doing it from my flat.

I packed my bag again but this time with my dress, bra, boobs, make up, wig and heels. I put on white tiny knickers and tights under my man clothing. I thought I would go out for a walk after work dressed en femme. I was the manager and the main key holder so once the staff had gone Suzie could come out to play.

I went out at lunchtime to buy a handbag to complete my outfit. The afternoon went exceedingly slowly but eventually the end of the workday arrived.

Once all the staff had gone I fetched my femme bag from the car, locked the door, and went to the ladies to dress. I was getting aroused, as always, dressing lovingly in my bra, dress, heels and wig. I applied my make up with a skill that was improving. I checked myself out, looking at my profile, at my tits, hair and complete feminine reflection. I was pleased with the result.

I had got better at walking in heels and feeling every bit a woman I walked towards the town centre hoping I should not see someone who may recognise me. I needn't have worried. In any case I don't think they would have recognised me.

Only once in all the times I have been out was I made. It was a shitty youngster who just shouted "man" at me followed by other unpleasantries A car driver honked his horn at me which startled me. I initially wondered why, then I realised I was dressed female! That pleased me.

Otherwise Suzie's excursion passed without incident. I was out for about an hour and enjoyed it so much decided to repeat it again soon. In fact I dressed as Suzie a couple of times a week after work which is when life became fun. I had been and purchased a couple more dresses and skirts to vary my wardrobe.

On one walk a guy spoke to me on his way past. It was only something simple regards a pleasant evening. I replied softly to him in almost a whisper. I had been practicing to talk like a woman.

I saw him a couple more times on my walks by the river at about the same time in the evening. Our chats became a little longer and more friendly.

I changed the days I went out walking as Suzie but not the times. I didn't want to be predictable for I know we are all creatures of habit and I didn't want to keep meeting the same people. I tried to walk as a female and I tried to walk with a purpose, as if I needed to be somewhere.

I saw the guy a few times. One evening and he asked if I would like to have a coffee with him. I answered yes. We sat on the river bank outside on a terrace chatting. He wanted to know about me, things like was I married or did I have a boyfriend and about my job. I nervously asked him a little about himself but he appeared reluctant to give much away saying he was much more interested in me. I wonder if he had realised i was a cross dresser. Was he bi too or had I convinced him I was a woman?

After finishing our coffees we slowly walked a while along the river bank. It was a pleasant warm evening and I was in no hurry to be anywhere. He put his arm around my waist. I snuggled into him enjoying the moment as he commented on liking my perfume.

We found ourselves at the back of a boat shed, whether by accident, or design on his part. He stopped walking and pulled me in to a full embrace asking if he could kiss me. Before I could answer we were tongue wrestling. I was breathless. He leant me against the wooden boathouse kissing me passionately.

In no time at all he was caressing my tits. I know silicone tits feel good to wear in a bra, which holds them firmly in place, but they must also have felt realistic to him because he kept massaging them as we kissed. I felt so like a woman must feel.

His dick was getting hard. I could feel it pressing against me. I was also getting turned on, partly because he was, but also because I was turning him on. My clitty was half awake but was being held firmly by my beautiful tight tiny white panties. His hand moved to my ass. He stroked it through my sheer dress and the feeling of him caressing my panties was getting me hornier. His finger gently searched my crack arousing me further.

After a while he moved his hand to the front and stroked my thighs which felt delightful through my dress and tights. His hand started to make it's way up my thigh under my dress. I pushed his hand away explaining that this was my time, the wrong week, for him to do anymore. I wanted to enjoy this as a female not as a cross dresser, anyway he would have had a hell of a surprise.

We both were getting turned on, and still passionately kissing, I felt for his ever hardening dick. I rubbed it slowly through his trousers and gently squeezed his balls. I unzipped him and put my hands inside. He never objected indeed was keen.

I reached inside and found his hard member. I lovingly teased it for him then slowly wanked it through his boxer shorts.

I could feel the dampness on the end of it. I decided to make him cum so I took it right out. He was still facing me with my back pressed against the boathouse wall. Nobody had been round the back throughout our embrace so I felt safe wanking it for him where we were.

I thought about giving him a blow job but thought it unwise. What we were doing was fairly discreet. I could hide what we were doing should anyone appear. I sensed he was getting near so moved my hand faster.

It was lovely wanking him. I was nearly getting as much out of it as he was. It didn't take too long before he splattered hot cum up the wall and over my hand. I looked him in the eye and licked my hand smiling and kissed him again.

He had a huge smile on his face and said next time he would like to fuck me. I said that would be nice wondering if I should tell him I was a cross dresser but decided to leave it for now. We agreed to meet up for a drink on Sunday at 8pm. I would tell him my secret then and if he still wanted me I'd take him to my flat.

As we parted I wondered if I had truly convinced him I was a woman. As convincing as I tried to be including voice and mannerisms surely something about me must have given the truth away. Had it?

On Saturday afternoon I went in to town but this time was dressed as a guy. I wanted to buy a ladies watch and a couple of bits of inexpensive jewelry to make Suzie more authentic.

I was surprised to spot my date for tomorrow in one of the shops, not that I saw him was the surprise, it was that he was with a woman and two children, a boy and a girl. He had his arm round her just like he had done with me. I have to be honest initially I was jealous. The children called him Daddy. That made my mind up I wouldn't be seeing him tomorrow. I may be what I am. I may be a bit of a bi slut but I am not a home wrecker.

My parents split up when I was young and I wasn't going to impose that on anyone else.

I went home in a bad mood. I was looking forward to the potential of having a guy in my flat tomorrow. Now it wasn't going to happen.

I dressed as Suzie in a sexy mini skirt, skimpy top and boots, fully made up with my wig on. I then went online to my favourite chatroom.

Once there I got chatting to my long time CD friend Michelle. I explained my woes to her. I explained about the guy I had sort of been seeing and about our experience at the rear of the boathouse. I told her everything that had happened. I informed her of our plans to meet and why I wasn't going to turn up and why. This caused my gloomy mood for which she sympathised.

We had talked many times previously about our desires, wishes and fantasies. Many of them were shared aspirations. We had partially undressed on web cam together and had masturbated together on many occasions dressed in our lingerie.

Then Michelle asked me if I fancied going over to see her at her place the following day. The trouble was she was over an hour and half away. What was there to lose? It would be sexy fun no doubt, so I decided to go to see her. We exchanged phone numbers and she later texted me her address along with a horny message.

I spent my evening preparing the clothes I wanted for tomorrow. I selected my outfit with care as I wanted to look and feel sexy but not to look or feel slutty. First I took out a new shortish black satin skirt with a split up the thigh. A pink chiffon button through blouse with black swirls on it plus of course the rest of my female accessories.