Why?

By Samantha Jay
© December 2001

Well I don't really know where to begin. I started 'dressing' at an early age. Don't ask me why because I just don't know. I never told anyone and was always careful, I am an only child so I didn't have any sisters to force me. At first it was only bras and by the time I went to secondary school I had stopped doing it (fear of being found out I suppose) and so thought that I had grown out of it. I suppose even then I had realized that it wasn't a 'normal' thing to do.

Well I did the usual male things drinking, driving too fast and ogling girls except... I realised I wasn't just looking at the breasts or legs, but at the clothes. What type of bra, did the knickers match, were they stockings or tights. Not being handsome (or rich) girls didn't seem interested in me and I didn't really have many (okay any) girlfriends.

I tended to stay at home and read books, usually about electronics or sci-fi. No it didn't help me too much with my exams, I was an average student, but I suppose I could have been called a geek, but that word didn't exist back then.

Well I started to work away from home; travelling all over the country and one day plucked up courage and bought my very own bra. I went into a large department store and picked a box off the rack. I went back to my hotel room and opened the package. What a disaster... it didn't fit! What an idiot, I didn't know my size... hey I was a large and wore sixteen inch collar shirts. How do you convert that into thirty-four or thirty-six and what the hell's the B or C got to do with it. Well I couldn't go back to that store so I junked the bra and package, not in my hotel room but in a waste bin far away from where I was staying or working. You see, as every one of us knows, you have to be careful because people just don't understand (at least not in the UK).

Anyway it was a couple of months (and a different town) that I strolled into another well known store and brought another bra, I had measured myself by then, but as I still didn't know what B or C or even DD meant picked up the first one I could see (thirty-six B). It was a plain black one; I seem to have a thing about black bras. Well it actually fitted and with a pair of rolled up underpants in each cup I had a bust. After a few days of 'happiness' I lost my nerve and junked that bra, also far away from my location.

I couldn't understand the ups and downs. The ups of wearing bras and the downs of I am a man why am I wearing female clothes (albeit just a bra). Also I didn't understand why I kept going back and buying more. I slowly realised that wearing these clothes was addictive and that I was hooked. It didn't matter how many times I vowed to quit and threw the bras away after a few months I was desperate to wear another one. No I didn't need to 'dress' every day, but at least every other week and I also realized that I didn't mind the addiction.

Then one day I actually went and brought a one-piece swimsuit. It was blue and was size eighteen (a guess) and by now I had a flat of my own so that I could store things, okay for store read HIDE. By now I was getting adventurous and brought another bra but this time I brought some knickers, you guessed it they were black. I wasn't wearing anything else feminine... yet.

I found myself working in a city that was hosting an ideal home exhibition; you know the type of thing... knives that never need sharpening, tape that invisibly mended holes the size of a bus and gadgets that no home could function without. And there tucked away in a corner was a wig stall. Well I passed that stall from all directions scanning the crowd and the stall. How busy was it, did anyone hang around, how bored was the assistant and then with shaking knees walked onto it. There was no turning back and I bought a long Auburn wig. I stashed this quickly into my backpack and meandered around the stalls, going into crowds, darting down side aisles. I kept this up for about five minutes to shake off anyone following me.

My paranoia was such that I even took three different bus routes back to the hotel...hey MI5 had nothing on me. Finally I got to my hotel room and took out the wig and promptly put it on backwards. Well there were no instructions on the polythene and I had never worn one before. So, at least I had long hair (down to my shoulders) but I was still unattractive. This is real life man, there is no way that anyone could call me attractive (except a blind man on a galloping horse) passable maybe but not attractive.

It was around this time that I bought my first pair of tights.

After a couple of years (I was twenty-five by then) I met a good-looking (to me anyway) girl at a local singles club and I started dating. This was my first experience with the opposite sex and boy was I (how can I put it) crap.

Being a loner, I had never taken a girl out and so didn't know how to behave or even what to do. But I learnt and yes I threw all my stuff away including the wig. After going steady for a couple of years I popped the question. We had grown together and so it seemed the most logical thing to do. We married and I discovered sex (I told you I had no experience). I had not 'dressed' for about three years and although the urge was still there I thought that I was suppressing it okay. Life was fine and sex was good. Then I bought another bra (my partner and I were and still are different sizes) and found places to hide it.

Then one day (I can't remember how it happened) I asked my partner to make up my face. We were in bed at the time and she did so and I then recovered my bra from its hiding place and then made love to my partner. Note the wording I made love to not had sex with. In the morning my partner asked the question. "Are you gay?"

This seems to be the usual reaction to men dressing. Nobody asks a woman if she is a lesbian if she is wearing trousers. A skirt is part of the Scottish national dress but don't say that to a Glaswegian unless you want to find out how wonderful the experience of eating food through a straw is. It's called a KILT. And they are NOT gay.

But I digress. So we sat in bed and discussed my 'need to dress'. Fortunately I had judged my partner correctly and she accepted it. It's a part of ME and she loved ME and she married ME and more importantly she wanted to stay with ME. Having a partner who at least doesn't object is one of the best things in the world. I would not go out dressed; I am and will probably never be good enough, but its good just to be able to do it at home.

So I had partially left the closet although no one else knew. My partner helped me and started teaching me things that girls learn like what B or C or even DD mean. She also bought some clothes for me you know... dresses, skirts, blouses, stockings you get the picture.

I remember going into a store with my partner and looking at skirts and blouses. It was strange, I knew they were for me and was so excited, but on the other hand apprehensive. I had never gone that far, how would I look?

That night I changed, wearing a black bra (still filled out with rolled up underpants), black knickers and black tights (my legs seemed to look better in tights or stockings) I put on the blouse (hey the buttons are on the wrong side) and stepped into the skirt and pulled the zip up.

After putting on a blonde wig (why do we nearly always pick blonde) and slipping into flat-heeled court shoes I walked into the living room. It was strange walking in a skirt for the first time. For those unlucky people who haven't tried it, it's like walking with your legs tied together. The amount you move your legs is determined by the diameter and length of the skirt. It's obvious when you think about it, but if you never experience it you never think about it.

She didn't laugh and wasn't shocked and she helped me with what was my first 'full dress'.

She also started getting matching clothes (nighties, underwear that sort of stuff) and we have wild passionate nights of lovemaking. Then I hit upon specialist shops. I found one not too far from one of the locations that I had to visit and so, with my usual paranoia, staked out the shop.

I drove past at different times checking the area, seeing how busy the road was, and whether there was an escape route into another shop if I lost my nerve. I may have had one stocking clad leg out of the closet, but there was no way NO WAY I was going to expose my secret to anyone who might know me or a friend of mine or a friend of a friend of a... you get the picture.

It took a long time for me to cross the threshold of that shop (under cover of darkness of course), but what an Aladdin's cave. As it was close to Christmas, I wanted to buy clothes for both of us, so as well as silicon breast forms (unfortunately without nipples) and complete schoolgirl uniforms for both of us.

My partner was overjoyed with the clothes and loved the feel of my breasts and, that night, we reached new highs in our lovemaking. I am planning another 'clandestine' visit to another specialist shop, with all my careful checking, to put right the omissions I made on my first visit.

I will buy the nipples, adhesive and one of the artificial vaginas (that ought to blow my partner's mind when she discovers I have no penis during our lovemaking). I am mindful that I appear to be getting the lion's share of the pleasure and so will get her some things (vests and underpants) so that we can have a 'male/female' session instead of 'female/female' one.

It is something we have discussed in the past, I believe I understand her needs and my partner understands my phobias. I would like to get her a realistic penis, but I am worried (as well as curious) about being penetrated. I would like to know what it is like and I have to give more back to my understanding partner.

That is not to say that she doesn't enjoy it now, but I must try to be less frightened, but the unknown scares me to death. However I must overcome my phobia.

We also plan to go somewhere together where I can 'dress' for longer (like a weekend), but this will be just the two of us. Having an understanding partner (or even an understanding girlfriend) means that it is easier buying things and it makes it easier to live. There are women out there who do understand.

My fondest memory I have is of Samantha giving my three-month-old daughter a bottle late one night. She was cradling the baby against her breast gently encouraging the baby to drink and talking softly. I will never ever be able to thank my partner enough for allowing me to share that pleasure. I only did it once but once was enough. It was GREAT!

I mainly dress before going to bed (having a kid is a great way of curtailing cross-dressing) and we have both discovered that our lovemaking is different.

Although I haven't fully surrendered myself to my feminine side yet (see above), I know that I must try. We also want to try some of the more tarty styles... mini skirts, knee high boots, tight jumpers that sort of thing, but being middle aged and with both of us with what you could call after pregnancy bulge, it will probably be more funny than serious, but, hey, we will be pleasing just ourselves so, who cares?

I never really had the Bridal fantasy, but I would like to know how it feels to be pregnant. It comes from trying to share and understand what my partner went through (I know I can't fully, but I would at least try to sample some of the 'discomfort' that I had put her through) and also I have this wild idea of trying to find out how two heavily pregnant females would have sex with each other. I imagine with great tenderness.

I can honestly say that our marriage hasn't been better and our lovemaking (see I still say lovemaking instead of sex) is never dull or boring.

Having discovered on-line fiction I have found that most of it is FEMDOM, SISSY, MAGIC or SCI-FI (this is not a criticism just an observation since different things appeal to different people) with just a little of what appeals to me... simple cross-dressing male to female maybe forced but not necessary real life.

Stories like "A Lakeland Visit", "The Hit" (where can I get a Bunny Costume), "Kristine Kyncaid" and "Cross-dressing Club" (this one woke me up to my partner needs) to name just four.

I am a male and want to stay a male, however I also like to masquerade as a female from time to time and fantasise that I can pass for one even though I know that I can't. I have noticed that when my job really stresses me out a change to my feminine persona is better than any tranquillisers.

Also, there is a very good on-line TG community not just for transsexuals, but also for all aspects of gender issues. They have tips (I found out how to tuck), chat rooms where you can talk to people anywhere in the world (hey Julie could be the guy next door), on-line fiction pandering to all tastes (storysite.org and fictionmania.com to mention two of the best).

The ability to correspond with like-minded people (I would like to thank Karen Anne Summerfield for her encouragement here and she writes some great stories, make the cheque payable to cash, Karen).

There are sites that give help and advice for anyone who wants to transition where you will get all the gritty realism, SRS is not all fun and happiness, sometimes it can be lonely and hard and for a very few unlucky women it doesn't solve their problems, just brings new ones.

There are also sites, which give advice on how to come out and how to break the news to your partners. There are lots of sites put together by TS and TVs (shit some of the pictures are so good it makes me jealous I was and am nowhere near as good as that and they are better looking than some of the real girls I have known, life is so unfair). Most of the sites have links to others so I will leave it to you to explore (Hey, you found this one didn't you?).

Why have I written this? Shirley Ann Sometimes wrote a story called, "My Husband", and it got me thinking that maybe in my poor humble way that I may help someone come to terms with his need. I would have liked to put my partner's side, but she would have a fit if she knew I had written this.

As Gail says in "My Husband", 'If its okay in thirty years, he can wait till then'. I don't think that in my lifetime I, and others like me, will be regarded as anything other than perverts and so for my partner and child's sake I always act like a spy when I go to buy anything from speciality shops, always pay cash.

On-line I will let Samantha speak for me. After all, she's a lovely, caring and understanding woman who is always willing to help with advice from her limited experience (just like me really).