Chance of a Lifetime

[DaraJaney]

Denis walked down the centre of the shopping arcade and slowed his pace when he came to “Sweet Secrets” so that he could get a good look.  The shop was packed full of ladies’ frillies – petticoats, stockings, lingerie, floral dresses.  He was fascinated by them.



Every day he found an excuse to wander down the arcade and catch glimpses of the wonderful clothes.  He never had a sister and his mother had no interest in feminine clothes but he could never take his eyes off a full skirt or short pleated skirts.



He had to be careful that nobody noticed his unusual interest.  He would glance sideways as he slowly walked past, desperately trying to get a good look but aware that if he stopped and stared somebody might wonder if he was a little too interested.  He would be mortified if anyone found out.  If his school pals got any inkling that he liked girly things, his life would be over.



If a shop assistant looked at him curiously, he would look away immediately but blush profusely.  When that happened he would try to stay away for days but he would always be drawn back.



This Saturday he was passing by and the shop owner came out.  “Young man!”  She stood in front of him so that he could not pass by.  He was surely rumbled.  His face flushed.  “Would you like to earn a little money?”  He was visibly relieved.  “Eh, yes of course.”  “Well come in here with me.”



His stomach did a somersault.  He was getting a chance to walk into the shop of his dreams!  He followed her towards the counter at the back.  To do so, he had to walk through rows of dresses and past rails full of suspender belts, basques etc.  His arms brushed off outer layers of organza petticoats and sent a shiver down his spine.



He was goggle-eyed and desperately trying to look cool.  The shop owner, Ms. Von Trapp, turned around and smiled at him.  “I just need somebody to put in a few hours at weekends to handle the stores – you know, unpack goods and put them on display.  None of us ladies on the staff can afford to muck about back there.”  They were always dressed up to the nines to advertise their outfits.



Denis was speechless.  He was actually being handed a reason to be in this shop every weekend.  But he was terrified that his real passion for frilly things might be exposed.  Temptation was too much though and he accepted.



His first job was to unload a small van into the store room.  He had to clear some space and carry the large boxes in.  It took a couple of hours and it was almost closing time.



“Could you come back in the morning and unpack those boxes?  We don’t open until lunch time on Sundays.”  She held out a pair of keys to him.  He nearly wet himself.  He was being given an opportunity to have the shop and the store room all to himself for a whole morning!  He just nodded in speechless agreement.

[DaraJaney]

The next morning he woke at 6am.  He was sick with anticipation.  He figured that he might as well head down to the store as soon as he had breakfast.  The sooner he got down there, the more time he would have to himself.  He was out before his mother got up.



He unlocked the door and entered the store.  The arcade was otherwise deserted.  He mooched around the merchandise but was still terrified that somebody would walk past and see him.



He went into the store room.  He was totally safe from prying eyes here.  He opened some of the boxes that he had to unpack.  The first contained frilly panties of a variety of sizes.



He quickly stripped off and pulled a large pair on.  He briefly wondered if it would be obvious that somebody had worn them but the temptation was overpowering and he just put them on.  His enormous erection was obvious.  A little wet patch developed and he realised that he was going to have to take the panties away with him afterwards.  He figured that they wouldn’t miss one pair.



The next box contained white suspender belts and he put one on around his waist.  He was almost shaking as he searched for appropriate stockings.



This was complete fantasyland for him.  He pulled a white lace-top stocking up one leg.  He stretched one strap from the suspender belt to the stocking top.  It took a few attempts but eventually the little button held.  He twisted to do the other one up towards the back.  Soon he had both stockings on.  He walked up and down and was so excited by the feeling of the stockings stretching and easing back with each step.



Next he found a pettislip.  He pulled it over his head, put his arms through and pulled the multiple layers of petticoats down.  He stood in front of a mirror.  The petticoats stood out beautifully.  There was just a glimpse of the lace-tops of his stockings when the petticoats swayed.  He tugged them down modestly.  He was so turned on!



There were so many dresses to choose from.  In the end, he went for a cerise coc-ktail dress that sat perfectly on his petticoats.  He completed his outfit with shoes with a small heel and white gloves and put some colourful necklaces on.



He walked back and forth and thrilled at the petticoats swishing against his stockings.  He twirled and watched the layers flutter about him.  This was just incredible!



Suddenly, he heard somebody out in the shop.  He froze.  He could hear the footsteps walking towards the store room door.  He nearly threw up.  He couldn’t let anybody see him like this!  He desperately tried to reach the door handle first so he could hold it closed but the heels prevented him from running and he scampered as best he could.  But the door handle turned.

[DaraJaney]

The door opened and Ms. Von Trapp looked in.  She smiled as she looked him up and down.  Denis was horrified.  His one and only chance in his life to try these clothes on and he is immediately rumbled.  He was just relieved that his erection was well hidden below the layers of petticoats.



“I thought so!”  She calmly walked in and closed the door behind her.  Denis clutched his skirts nervously.  â€śI saw you passing by every day and I could see that you were fascinated by the clothes.  Well, well.”  She chuckled as she walked around him looking him up and down.  What was she going to do to him?



“I’m sorry”, he mumbled and reached towards the zip of his dress.  â€śIt’s ok”, she assured him.  He stopped and slowly lowered his arms.  â€śYou just need a few adjustments and you’ll look so pretty.”



Denis was taken aback by this.  She went to the other door which led towards the staff room and toilets.  Since all the regular staff were female, the staff room was full of women’s things and looked like a ladies’ dressing room.



Over the next hour she helped him shave his legs and chest, apply make-up and lipstick and even styled his hair with clips and slides and he did look quite impressive.  But she wasn’t finished.



She coaxed him into a corset with bra-cups and laced him into a much more feminine figure.  He could hardly breathe but she selected a coc-ktail dress with a tight fitting bodice and full skirt and the look was amazing.



Once again, Denis was flouncing up and down the store room, stealing glances in mirrors.  She had selected four-inch heels.  He tottered dangerously at first but was already getting used to them.



He hardly noticed the time go by he was so excited and turned-on but suddenly it was noon and he heard footsteps out in the shop again.  â€śOh that’ll be Marjorie”, Ms. Von Trapp explained nonchalantly.  Denis was once more frozen to the spot at the prospect of another lady seeming him all dressed up.  The door opened and Marjorie walked in.



“Oh!”  She stopped in surprise and then looked towards her boss for an explanation.  â€śThis is Denise who is joining us in the shop at weekends.”  Marjorie smiled and held out her hand.  There was no sign that she thought he was a boy.  Denis relaxed a little but he was still extremely nervous at being unexpectedly dressed in a corset, coc-ktail dress and stockings and suspenders in front of two ladies he had never met before this weekend.



“Help me bring these out please Denise”, Ms Von Trapp asked, bringing a collection of hangers out into the shop.  Denis had little option but to take the other set and follow her out into the shop and the certainty of being seen by passers by.



He walked out into the shop, eyeing the arcade nervously.  There were people strolling up and down.  Suddenly three young women entered the store giggling at the display of lingerie and that was it.  Denis was now out in public dressed up in women’s clothing and make-up.  He was so hard!

[DaraJaney]

Ms. Von Trapp kept him busy going back and forth.  He was part thrilled but part terrified that somebody would recognise him.  His feet were aching quite a bit from the unfamiliar high-heels.



He pottered about until two o’clock when Ms. Von Trapp asked Marjorie to watch the shop.  â€śWe’ll go for a bite to eat.”  She handed Denis a small jacket and walked out of the shop.  He had no choice but to follow.  Just a couple of hours ago he was privately dressed up in the store room and she had somehow managed to manoeuvre him into going right out and about in public.  He never had any choice in any of this.



His flamboyant outfit got plenty of looks.  His boss walked quickly and he did his best to scamper along behind.  She went towards the front entrance to the arcade.  There were cafes across the road.  Now he was out in the open air and his petticoats swirled in the wind.  He gave a little yelp as the breeze blew up around the tops of his stockings.  Ms. Von Trapp turned to look back and smiled.



He was somewhat relieved to get into the cafĂ© but many heads turned as he entered.  His heels clicked loudly on the tiles drawing further attention.  It took a few attempts at sitting down before he got his petticoats properly swept under his bottom.  The hem of his dress was well up his legs even sitting down and he was terrified that somebody opposite would be able to see the lace tops of his stockings.  Whenever he thought about this he went hard again.



He spent the rest of the afternoon helping around the shop and it was only when Ms. Von Trapp sent Marjorie home that he was able to go back into the staff room and undress.  It was thrilling to have been able to wear that stuff but he was so relieved to be able to step out of his high heels.



For a minute, his feet maintained their curved shape from the shoes and he had to rock back and forth a few times in order to ease them back onto the flat.  Then when he had removed his dress and pettislip, he was able to unlace his corset and let out a deep breath.



Ms. Von Trapp helped him to remove his make up and restore his hair.  â€śWhy don’t you come around to my house tomorrow evening?  I have some other things that might interest you.”



Denis walked home unable to believe what had just happened.  Lying in bed that night, he couldn’t decide whether to reminisce about the day’s events or dream about what the following day might bring.  He tossed and turned and eventually pleasured himself to the sweet memories.

[DaraJaney]

On Monday evening, he entered Ms. Von Trapp’s elegant house.  She led him upstairs and into a girl’s bedroom.  He hadn’t seen anything like it except maybe in movies set in the 50s.  She opened a wardrobe and revealed a large collection of girl’s dresses in all sorts of pretty colours.  They were all extravagantly decorated with lace and had full flared skirts.



They looked like they were designed for an eight-year old but they were much larger in size.  Ms. Von Trapp ran her fingers tantalisingly along the row of skirts and turned towards him.  â€śYou like?”  Denis was almost salivating.  He didn’t want to admit that these very sissy dresses appealed to him but once again temptation and the arousal got the better of him.



Within the hour he was dressed in a pink polka dot frock with a white starched pinafore.  He wore white tights and pink pettipants that were only barely covered by his short dress.  She had tied a pair of pink ribbons in his hair.



He stood in front of the mirror admiring himself when she handed him a large doll in a very frilly Victorian dress with bloomers.  She gave him a brochure of little girl’s clothes and explained that she had to head out for a moment.



He got about an hour to himself.  He alternated between leafing through the brochure admiring the pretty dresses and flouncing around in front of the mirror, trying to see how much he could bend over without his frilly pettipants being seen – not very far as it turned out.  Occasionally, he would rub himself and come close to orgasm.



Ms. Von Trapp returned as he was standing in front of the mirror clutching his doll.  â€śYou know, this is a very special mirror” she said reaching towards a knob on the wall beside it.  Denis watched her as she turned the knob.  The effect on the mirror was like opening a set of blinds.  Suddenly he saw his mother on the other side of the glass looking him up and down.



He squirmed in embarrassment and his knees rubbed together and he became so aware of his tights.  He stood completely upright hoping that she would not see his frilly panties.  He paced nervously around the room as his mother came around and in the door.  He was dying for his erection to go down although once again the layers of petticoats would probably save him.



There wasn’t much he could say.  She had seen him quite happily flouncing around in a very sissy dress and holding a doll very willingly.  Ms Von Trapp explained to her that it was surprisingly common for boys to be interested in this.  Denis shifted uncomfortably amongst his petticoats.



“Is it something he will get over or tire of”, his mother asked hopefully.  â€śWell why don’t we let him stay here for a few days and find out?” Ms Von Trapp suggested.  Denis was thrilled at the prospect of being able to try all the dresses but more than a bit concerned about dressing like this full time – even for a few days.  He wasn’t sure if he would like that.  This was the first time he even tried it.  He couldn’t remember where he had left his boy’s clothes in the excitement but there was no sign of them anywhere.



But he was so turned on at the prospect that he couldn’t reject it either.  His silence was taken by his mother as consent.  â€śFine.  He can wear all the frilly panties he wants and we’ll see.”



Denis had a fantastic few days wearing a number of different dresses each day but he was always more than a little nervous about there being no trousers in sight if he changed his mind.



Ms. Von Trapp noticed him reading Alice in Wonderland and paying special attention to the illustrations.  She got him an Alice costume and he loved the kingfisher blue dress, the white pinafore with pink trim, his white tights and black t-bar shoes.



Another day she produced a full Bo Peep costume.  He stood looking at the blue and white dress and the full length bloomers with long rows of lace at the ends of the legs.  Even compared to what he had worn so far it was so sissyish that he was embarrassed but Ms Von Trapp knew that he would never be able to refuse, it was such a turn-on for him.  She had seen it all before.



A mob cap and crook completed his costume.  He stood in front of the mirror mortified by the huge skirt and the frilly bloomers but he had the biggest erection ever.

[DaraJaney]

On the Thursday Ms Von Trapp introduced a new dress.  It was powder blue and flared from breast level.  It seemed almost babyish to him but he was once again powerless to resist.  It came with a matching pair of panties with lace trim and rows across the bottom.  The sleeves were puffed out and the lace trim on his panties was visible in the mirror unless he specifically tugged his dress down as far as it would go.  What he didn’t know was that from any other vantage point the lower row of lace on his panties was fully visible.  There were also little blue lace-trimmed ankle socks.



She showed him a Shirley Temple movie and watched his face light up.  That was all it took to coax him into the red polka dot toddler dress.  Then she produced the oddest looking thing.  It was an electric appliance with dozens of thin metal pins.  He wondered was he about to be tortured!  But within a couple of hours he had a head full of tightly pressed ringlets.



His mother came to visit again and her eyebrows were well raised when she saw him in the Shirley Temple dress complete with his ringlets although she made no specific comment.  The next couple of days he got to wear similarly ultra short, very flared dresses in peach and lavender.  Both had similarly matching panties and ankle socks.



One day he came up the stairs and noticed an open door at the end of the corridor.  The room was decorated even more prettily than his room.  He went along the corridor for a better look.



He pushed open the door and saw that it was a nursery - obviously for a baby girl.  It was decorated in a very old-fashioned way with wooden play-pen, cot and high-chair.  There was a rocking horse by the window.



In the corner was a changing table.  Denis walked over and put his hand on the pile of fluffy white cotton nappies.  His erection stiffened further.  He was surprised himself.



“Do you like the room?” Ms Von Trapp said suddenly behind him.  Denis swung around expecting to be scolded for snooping around.  Once again, he had an inexplicable fascination with all of this.  She walked towards him smiling.  A puzzled look came over his face.  He looked around the room.  It was hard to tell because it seemed to be so consistent but he couldn’t help feeling that the furniture was all very large for a baby.



“Shall I put you in a nappy”, she asked.  He was shocked but felt a thrill of excitement.  â€śJust to see what it’s like”, she added giving him enough rope to hang himself.  This time he put up a show of reluctance - but eventually conceded – “just out of curiosity.”  Ms. Von Trapp smiled knowingly as she closed the nursery door.



Thirty minutes later Denis waddled across the room towards the play-pen, his legs bowed by the thick nappy, tightly enclosed within the elasticated plastic pants.  His legs looked quite chubby in the thick wool-knit pink tights.  His nursery print dress only covered the top half of his nappy and came with matching frilly panties and bonnet.



She had popped a large pink soother into his mouth and pinned it to his dress.  His pink fleece booties slid a little on the polished wooden floor.  He went into the play-pen and plonked down amongst the cuddly toys.  She let him play there for a while before producing a large baby bottle of milk.



She brought him from his pen to the high-chair.  When he sat up she pulled straps over his arms and chest before swinging the tray down in front of him.  She removed his soother and pushed the teat of his bottle into his mouth.



He suc-ked for a couple of minutes before she withdrew the teat.  He looked up at her wondering why she had taken it out.  The level of milk in the bottle hardly seemed to have gone down at all.  Suddenly he burped.  The look of surprise had hardly left his face before she pushed the teat in again.  Eventually she left him to hold the bottle up himself and it took him ages to finish it all.  He learnt that he did have to take breaks now and then to burp.

[deewet69]

I love your story and writting.   Can't wait to read more.   Deewet