Joe's Story

[DaraJaney]

When Joe reached puberty he started looking at girls in a different way.  He had always thought they were stupid and couldn’t understand why any self-respecting boy would want to have anything to do with them.  But now he was beginning to see the attraction.



But for Joe there turned out to be a further attraction.  He began to be strangely interested in their skirts and dresses.  He would sit doing his homework in a front room by the window being constantly distracted whenever a schoolgirl passed by the gate.  He found that he particularly liked to see pleated skirts, especially above the knee, with nice white knee-high socks.



If he looked up and saw a girl with a really long skirt, or a straight skirt or with knee socks sagging at half mast, he would frown disapprovingly.  But why the hell should he be so fascinated by this?



He began noticing things that would never have impinged on his consciousness before.  A teen-age girl at church in a pretty yellow high-waisted dress that looked much too childish for her.  But he loved it.



Going to school in the morning he would look out for one girl in particular.  The local convent school had changed uniform from an old-fashioned green gymslip to blue sweater and skirt.  Most of the girls wore long skirts denying him any glimpse of bare knee.



But one girl who was in final year obviously didn’t want to bother with the expense of the new uniform and she still wore the gymslip which by now was well above her knee and barely contained her growing bosom.  He loved seeing the gymslip and wondered why he never appreciated it before, when all the girls wore it.



He also seemed to enjoy the idea of this older girl wearing a much more childish uniform than the younger girls around her.  He reckoned she was probably very embarrassed by this and must have been teased by the other girls since she stuck out like a sore thumb.



Joe began to wonder what it was like to wear a skirt or dress.  His older sister had left school by now but he hoped that there might be an old uniform in a trunk in the attic or somewhere.



He waited until everyone was out before checking through every trunk and suitcase in the attic.  No luck.  He did find a black skirt which was reasonably flared and a further search turned up some white knee socks.



He nervously stepped into the skirt and pulled it up over his trousers.  It zipped up at the back.  He unbuckled his belt, undid his fly and let the trousers drop to the floor.  He was strangely excited by all this.  He pulled of his trousers, shoes and socks and pulled on the knee socks.



There was an old wardrobe in the attic which had a mirror in the door and he looked at himself in it.  He couldn’t believe he was standing there in a skirt and white knee socks.  The idea would have horrified him only weeks before.  But he loved the feeling.  He ran his hands around the skirt and savoured it.



Over the following weeks he took every opportunity to sneak up to the attic and hunt for other girl’s clothes.  He found a blue plaid dress with a stiff white collar.  He took off his shirt and trousers for this.  He stepped into the dress, pulled it up and zipped himself in.  As he walked over to the mirror, he noticed something tickling his thighs.  He pulled up the skirt of the dress and found that there was a silky white underskirt built in.  This sent a shiver down his spine.



He hid this dress in his bedroom and every night took it under the bedclothes (just in case anyone might walk in) and pulled it on.  He got so excited at this.  He realised that there was a strange stiffness in his pee-pee.  His stomach felt really odd but it was all a very exciting feeling.



But he really wanted to know what it felt like to wear a skirt or dress outdoors.  So at night time he put on the black skirt and white knee socks and pulled his trousers up over them.  He went downstairs and out into the back garden.  He pulled off the trousers and felt the cool fresh air on his legs under the skirt for the first time.



He became more and more daring as weeks went by.  He went into the front garden, still under cover of darkness, crept towards the gate and, if there was no sign of anyone on the road, he would stand at the gate and enjoy the feeling of being out in a skirt.  He knew that if somebody came out of the house he would be caught cold.  If that happened he would be thoroughly mortified.  But it seemed to be worth the risk.



Eventually he was daring enough to walk out onto the footpath and go up and down ten yards or so.  Then he would do so while a car was driving past – with his back to the occupants.  He wondered if they would notice his boyish haircut or his boy’s shoes as they went past.



When summer came around and he was regulary left alone in the house, he would even go out in broad daylight as far as the gate, taking great care to make sure there was nobody around.  Then one day he saw some children a hundred yards down the road and he still walked out onto the footpath for a few seconds before disappearing back into the safety of the garden.



He began to wonder about wearing girl’s panties.  The idea revolted him at first but he eventually found himself inexorably drawn to the idea.  He found a pair of floral patterned and lace trimmed panties and pulled them up under his dress.  Now he wanted to wear panties every time.



While searching for more clothes he came across a pair of tights.  He dropped them back in disgust.  How could anyone wear such horrid things.  Well, it wasn’t long before he was trying them on too and going out into the garden in the dead of night wearing a dress, panties and tights.

[DaraJaney]

Joe’s voyage of discovery continued as he began to be excited by seeing TV programmes where someone was tied up.  This at least was an interest that could be shared with his friends.  Kids enjoyed tying each other up.  But what he really wanted was to be tied up while wearing a dress.



But it is difficult to tie oneself up.  He found that he could tie his wrists loosely and then bind them more closely together with a padlock.  He could tie his ankles together and then pull them up behind his back and padlock the ties to his wrists.  If he left the key on the floor on the other side of the room he would have to shuffle across while tied up to get it before he could free himself.  There was always the exciting possibility that he might not be able to reach the key and he would be stuck tied up.  But in reality he would have been mortified if he was caught like this.



He was always terrified of being caught.  One night he found a pleated tennis skirt in the attic.  He tried it on and was admiring himself in the mirror when his mother opened the door without knocking.  She just smiled when she saw him in the skirt and said nothing.



After that he took every precaution possible to avoid being caught.  He was fortunate that he often had the house to himself but he always had a chair propped up against the door and various other measures to ensure that if anyone came home unexpected, he had some escape route.



One night he tied himself up wearing a dress and suddenly felt very funny.  Next thing he wet himself.  Since he had never been given any sex education he didn’t realise what was happening.  Now every time he wore a dress his pen-is swelled up and his tummy felt funny.  He couldn’t go so far as to tie himself up or he would be sure to wet himself.



Eventually he realised that it wasn’t pee but some sticky white substance.  This was all very confusing.  At night sometimes he dreamt of wearing girl’s clothes and he would similarly wet the bed.



He became so concerned that he even mentioned these odd experiences to his mother.  He just told her that if he thought about certain things his member grew bigger.  But he wouldn’t tell her what it was he thought about.  She just told him not to think about those things.  Some chance!



The upside was that he now got a thrill from just thinking about it.  He lay in bed at night dreaming up all sorts of scenarios, some of them more far-fetched than others, where he would be forced to dress as a girl.



This wetting was becoming very awkward though.  It was very difficult to hide the consequences.  There was also the curious experience that every time he wet himself, he felt totally guilty about what he was doing and swore he was never going to do it again.  But inevitably within days he would be rummaging in the attic again hoping to find another pretty dress.



Things took another turn when he started getting turned on by the idea of being dressed like a baby.  He found an old white sheet and cut strips from it to improvise a nappy.



On one occasion relations who had a little boy were staying with them and they had a push-chair.  Joe snuck out late at night with his nappy on under his trousers.  He squeezed into the push-chair, one leg either side of the central strap.  He wrapped a chain around his ankles and locked it in place so that he couldn’t get out of the push-chair.  He had left the key twenty yards away so that he had to push himself in the chair to get to it.  About half way there he came in his nappy.



Of course he wondered what the hell was the cause of all this.  Why did he have these feelings that had to be unnatural?  He was aware of transvestites.  They turned up occasionally on TV chat-shows.  He would be dying to hear their story but his mother would always switch off anything like that.



Joe went to a boys-only school and he wasn’t an outgoing type so his contact with girls was minimal.  It really wasn’t until he went to college that his interests were aroused.  It was only then that he fully appreciated how his feelings about wearing girl’s clothes were similar to his sexual feelings for girls.



His activities at home became frustrated by a gradual clear-out of his sister’s old clothes.  He wasn’t half as excited about her current clothes – they weren’t anything like as pretty.



College, however, provided two annual opportunities to dress up – Halloween and Rag Week.  In his first year he didn’t have the nerve to take these golden opportunities but observed how many young men happily dressed up in drag and ran around in public without giving it a second thought.  For him though the stakes were high.  What if someone realised that he actually enjoyed it?  He couldn’t bear being outed.



By second year though he built up enough courage to ask one of his female class-mates if she had anything he might wear for Halloween.  To his delight she suggested a can-can dress that she had.



A gang of them arranged to meet in one house to get dressed.  The girls ran upstairs to a bedroom while he was sent into the living room to change.  He put on the dress, the black seamed tights and squeezed his feet into the biggest women’s shoes he could find.



The girls came down when he was ready and dragged him up to the bedroom where they worked on his make-up.  This was a whole new experience for him.  Not just lipstick and blush but they used eye-liners and mascara.  He was practically shaking as they transformed him.



He had to struggle to contain his excitement as he had his first experience of going out in public in drag.  They had to run for a bus and the girls laughed as he tried to run in the heels.  He loved it.  The bus driver made to grab at him as he passed by and generally he was the centre of attention.



When they arrived at the Halloween party they all flung the bags containing their normal clothes in a corner.  Oh how he secretly hoped that someone would steal his regular clothes and he would have no choice but to wear the dress home.



As the night wore on some of the tortures that women have to endure began to hit home.  The shoes were agony and mascara started getting in his eyes.  But it was all worth it and he had the time of his life.



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[DaraJaney]

As each Rag Week or Halloween came around he desperately wanted to dress up in drag again.  He realised that sooner or later someone would start wondering but the desire was too strong.

He was always dependent on some female friend to provide him with clothes and/or make-up.  Often they wanted to make him look as silly as possible whereas he wanted to look as pretty as possible but there was no way he could say that.

He also had to make sure that what he wore was not too revealing – he didn’t want any embarrassing bulge giving the game away.  The problem here was that the more exciting the outfit – the greater the danger.

Inevitably someone said “you always seem to dress up as a woman when there’s a fancy dress party – are you ok?”  He would desperately laugh it off but he knew he had to be careful.  Anyway once he was out of college the opportunities tailed off. 

When he started in paid employment, he moved out of home and into a house shared with three other guys.  He was now away from any source of female clothes.  These were frustrating times and he had to survive on what went on in his head.

He didn’t have much luck with the girls and wondered if his secret interest was responsible for this.  He couldn’t see how.  He was definitely attracted to girls and not boys.  But not many girls seemed to be attracted to him.

He was particularly intrigued by one girl who frequently mentioned male cross-dressing.  She only ever wore trousers and he wondered was she actually a female cross-dresser.  How could you tell?  Lots of women hated dresses.  It was just the way she kept mentioning cross-dressing that intrigued him.  He did get to date her a couple of time but he was really hopeless at that sort of thing and it didn’t get beyond that.

Eventually he did manage a relationship that lasted more than a few dates.  She liked wearing feminine clothes which pleased him.  On a few occasions he managed to pull on a skirt or a dress of hers when she was out at the shops or something.

To test the water one time he got out of the bed in the morning and put on her blouse for a “laugh”.  She didn’t find it funny so that put him off going any further.  But the relationship continued and he felt that he was going to have to come clean at some stage.

Next time he put on a blouse and skirt as she lay in the bed.  He didn’t try to make any laugh of it this time.  She knew he was serious and they talked about it all night.  Initially she seemed upset but he had to hope that she knew him well enough at this stage to realise that he was basically a decent person and that this was just a quirk.  He was relieved that she didn’t break it off.  But she didn’t want to have anything to do with it either.  Eventually the relationship broke up anyway for other reasons.

Over the years flat-mates came and went and they moved house frequently.  He eventually found himself in a mixed house.  The others were all from out of town originally and generally went home at the weekends.

He felt desperately guilty about rummaging in the girls’ drawers but he had no other opportunities at this time.  If he noticed black stockings drying on the clothes rack, he would be dying for the weekend to come around to go hunting for them.

He was very careful to try and leave everything back precisely where he got it and was terrified that he would be rumbled.  It would be bad enough to be exposed as a transvestite but he knew that they would never forgive the invasion of privacy.

Stockings were a real problem.  Unworn stockings had a shrivelled up kind of appearance that was difficult to restore after they had been worn.  He took care to use a condom when wearing their knickers to avoid the problem of rising damp.

It was only around this time that he was first able to dress fully from head to toe in women’s clothes – panties, bra, stockings and suspenders, blouse, skirt, sweater and shoes.

He became more interested in lingerie.  He found some magazines that advertised mail order lingerie.  But he didn’t have the nerve to use his own name and address and he would have to pay by cheque.  Then he thought that he could get a bank draft.

The office he worked in was just one of a number of businesses and flats in the one building and the post was left in the hallway everyday for people to take what was theirs.  There would often be unclaimed items from former occupants.  So he used the office address with a false name.

He nervously checked the post every day and eventually it arrived.  He was able to whisk it away without being seen.  He now actually owned black suspenders and stockings!  This was a new beginning.

The first sex shop appeared in town and he built up enough courage to go in and buy a sexy maid costume.  He wondered what he would say if he bumped into a friend in the shop – a friend who would know that he didn’t have a girlfriend.

This was fine as far as it went but he could only get sexy clothes by these means whereas he would also love to have some pretty clothes.  He would sometimes lie in bed at night despairing that he would never ever get to wear a beautiful dress with layers of petticoats for example.  Life was so unfair!

Then the internet arrived.

[DaraJaney]

Joe wondered, though, just how safe it was to search for cross-dressing stuff on the internet.  Surely someone somewhere could trace every site that you visited.  It took a while to build up the courage to type the word “transvestite” in to the search engine.  He half expected a SWAT team to smash through the windows and doors within seconds.



It turned out that there was lots of TV and CD stuff on the Internet.  He soon found sites selling adult-size “little girl” dresses.  They were expensive and he didn’t earn a lot but the temptation was too great.  His office had moved into its own building so he had no choice but to get them delivered to his home address.  He was usually home first in the evening so he reckoned he could whisk away any packages before anyone else would be there to ask awkward questions.



Soon he was the proud owner of a pink dress with lace trimmings and a net petticoat.  Then he ordered a voluminous chiffon petticoat from America.



It became clear to him that you could have just about anything you wanted made to order if you had enough money.  He bought a navy gymslip with a really short pleated skirt.  He couldn’t believe that he actually owned these clothes!



It was strange how particular his tastes were.  He ordered white knee-high socks but the pairs that arrived weren’t quite right.  They folded over at the top, which wasn’t to his taste, or they would be off-white.



He spotted white knee-highs that he liked in a local department store.  After many abortive attempts where he ran out of courage, he eventually took a pair up to the till and bought them.  The lady didn’t bat an eyelid.  He was easily old enough now to be a father and hoped that she would think he was buying them for his daughter.



He also found internet sites that sold adult-sized baby clothes.  He couldn’t believe that he could order cloth nappies and plastic pants as well as short frilly dresses and bonnets.



He wanted to wet his nappy.  It was difficult at first.  He would drink lots but even when he was bursting to go, his pen-is would stiffen at the thought of wetting his nappy and then he couldn’t do it.  He eventually learned to distract himself by reading something and then gently letting himself go.  He just loved that warm feeling as the pee spread around his nappy.



Feelings of guilt after his activities still persisted.  He would think he must be sick to want to wear a nappy and wet it.  But next time he would be trying to soil himself.  He found he needed to get down on his hands and knees or at least bend over before he could push a stool out into his nappy.



Despite having to deal with the soiled nappy, he just loved this experience and repeated the wettings and soilings whenever he could.



He got a better job and was able to afford fancier outfits.  Of course there was always the snag with mail-order that you didn’t get to try them on first and often costumes were disappointing when they arrived.



Still, he now owns a beautiful tiered baby dress short enough to show off a whole bumful of frilly bloomers, an Alice costume with frilled pinafore, a Dorothy costume and a variety of little-girl dresses, school uniforms, maids uniforms, cheerleader outfits, stockings, tights, petticoats and wigs of ringlets.



Within a few years his despair at never being able to wear what he really wanted to wear has been replaced with a wardrobe full of delightful dresses.  He thanked goodness for the Internet and all those people broad-minded enough to provide these beautiful outfits to whoever wants them.