A Cross Dressing Experience - First

Bill had been up in Brisbane seeing some cousins and was now getting on the train to return home to Sydney. The train left Roma Street train station, Brisbane at 10.04 am, so bill arrived early with his cousins John, Meredith who had 1 daughter Abbey who was 16 and 2 sons Mike who was 13 and Steve who was 9. John was told by Meredith to drop me and the family off at the station entrance, and then go and park the car. On entering the station, Bill saw a big clock high in the air that said 9.30am, this was good as I had 34 minutes to check in and get a coffee and morning snack.
Eventually it was 5 minutes to ten, and we walked over to platform two and along to carriage ‘C’- which was Bill’s carriage. Bill put his bag and pillow on his seat- 34 and went back to the carriage door to say good by to his cousins. The train departed on time which was uncommon, and bill sat in his seat having waved to his cousins as the train pulled out. Once comfortable bill saw on the empty seat next to him was a magazine – cross dressing monthly. Bill was a completely straight guy who had nothing better to do and started flicking through the magazine and looking at the pictures. As bill got to about half way a mid-30’s woman looked at him from across the isle, and said “so do you enjoy wearing a dress?”
Bill replied with,” well actually I have never done it”
The mid- 30’s woman said “ahh well we really need to change that then, and where are you going to”
Bill replied with “ahh, central station Sydney.“     
The mid-30s woman said “ahh good so we have until 12pm tonight ahh good and will do 935kms in the process- this is Australia.”
Bill didn’t know what to say, what had he got himself into, he didn’t know
The woman said to bill “my name is Amanda and I think we should go and get a sleeper cabin together so we can have some privacy.”  
Bill and Amanda went to the food cart to find out if they could get a sleeper carriage.
The country link officer checked the seating plan, ahh yes we have a sleeper carriage for you, 
We paid the remaining amount and gave up our old seats as we wouldn’t be needing them anymore- thus making the sleeper a bit cheaper.
We went straight to the sleeper carriage and once inside the lady said right into the shower and shave your legs, underarm hair and general arm hair.“
“O ok bill” said in a nervous voice
Once complete bill came out with the towel around his waist and Amanda said to him “if you are going to be a boy girl you really should start wearing towels above your boobs and if there is a spair wrap your hair in a towel also.
Bill said “year thanks”
Bill got dry and put on a pair of footy shorts and t- shirt. Then Amanda said to him, so ok I reckon with you we need to put on makeup, a bra, pantyhose, slip and a dress and some heals.
“Gosh- that will make me look like a woman” said Bill
“Year and that’s the idea isn’t it” said Amanda
Bill was speechless- he was not sure what to do or say anymore.
So sit down here and look at the mirror while I do your make up,
Amanda did eye shadow, mascara, and lipstick on Bills face.
She then handed him a bonds pink rear strap on bra which he tried with no luck to put on- so Amanda turned him around and did it for him.
Amanda then gave him some pink pantyhose to put on and got some black ones and showed him how to put them on,
As bill began to slip his left foot into the left leg of the panty hoes it felt very soft and smooth and comfortable- this made bill rather excited and he got the pantyhose on as quick as possible
Amanda then put the slip on bill and then helped bill with the dress, it was a long pink dress with purple ruffles all through it and it had short sleeves and the neck line was rather highly cut. This meant that the dress covered most of bills neck, it also buttoned up at the back.
Once bill had the dress on, Amanda gave bill some 4 inch, shinny silver high heals, bill put them on and Amanda had to help him with the buckle, then Amanda pulled out a black long wig and put it on bill, she styled it in a girls style with 2 pink hair bands- one platted pig tail in each.
On completion Amanda pulled out a red thin, lightweight coat and gave it to bill to put on, once he had it on- he really looked like a girl.
“Right so today your name is not bill but Lucy,” said Amanda who was struggling to think this was actually a guy.
Amanda also gave bill a lesson on how to wiggle her hips like a girl which with a bit of practise was able to do quite well at.
Then Amanda sat down and bill looked in the mirror and smiled and swirled around.
Then they both heard an announcement over the speaker system that all those travellers interested in receiving lunch should wait for a crew attendant to come around with cards, for the different types of meals and that meals could be picked up in 50 minutes from the food car.
Lucy thought to herself gosh its lunch time already- how time flies she thought
Amanda on the other hand said “oh good we can each get a lunch order and you lucy can go and pick them up” lucy was not interested in walking outside looking like this but with some persuasion from Amanda did not have a choice in the matter
Amanda said- no one knows you on the train lucy and heck u do not look the slightest thing like a guy,
Then they heard nock nock nock on the door
Who could that be Lucy thought to herself?
Amanda said, “Try your best to speak and move like a girl and will you Lucy and get the door.”
Lucy was shocked but Amanda had a look on her face of do as I say or you will regret it. It was the lunch man, Lucy got lasagne and Amanda requested the salad once got there tickets and said thankyou and closed the door- Amanda said so how did that feel
“Oh alright I guess” said Lucy.
“Only alright” said Amanda,” either that guy wasn’t thinking straight or he just didn’t care, but he had no idea that you were a boy.” 
Oh good said Lucy as she relaxed. 
Lucy and Amanda continued to work on how Lucy carried herself until they heard that “lunch orders can now be picked up from the food cart” over the PA system.
Amanda said that’s your cue and remember what we have been practising.
Lucy went to the food cart, there were 5 people in front of her so she had to wait a bit for an elderly man in his 70’s, a mother and her daughter [or at least that’s what it looked like], a boy who looked and sounded to be about 14 and man who looked to be either rather hung over or on some kind of drug [s]. Eventually Lucy got to the counter and said 1 lasanga and one salad please and gave the attendant her tickets. she then asked for a cup of black coffee with 2 sugars. She then also gave the attendant money for the lunches and coffee and slowly wandered back to her sleeper where they ate lunch, Amanda wanted to know how she went at getting the lunches.
“Well I don’t believe I received any bad or glaring looks” she said,
“ahh well that’s good” said Amanda
Then they heard over the PA system that Tarree would be the next stop and that Countrylink requested that all passengers departing the train at Taree please prepare to do so. Taree will be the next stop thankyou. “
Lucy said “oh so we are slowly making our way down the coast and into Sydney”
“Yes we are” said Amanda “and thus all the more reason why we need to continue practising how you should behave in public.” 
They continued practising for another 2 hours and then went and sat in the public gallery for an hour and a half, looking out the window and chatting with other passengers until dinner time.
At dinner time Amanda decided that they should go and sit in the dining room in car B, for dinner. Amanda fixed up Lucy make up, freshened her self up before they headed down to car B for dinner, where Lucy had the lobster, Amanda had the roast beef and vegetables for dinner. Once they had finished dinner they returned to their sleeper where they discussed the future once off the train. It was decided that Lucy and Amanda should swap mobile numbers in case bill’s parents would not allow bill to wear a skirt/ dress/ panty hoes and make up around the house. Amanda then had a 2 hour nap while she waited for the train to get in to central station at 3 minutes past mid night,
Lucy on the other hand decided that as she was so good at looking and being feminie that she would return to the gallery to look out the window and enjoy the view, as it was after 10 pm, no one was in the gallery to chat to and so lucy sat there in silence just looking out the window at the moon and sights near and next too the railway line.
At 11.30 Lucy returned to the sleeper and woke Amanda and they changed Lucy back into Bill, who also had to not only pack her own bag but also pack up Amanda’s to say thank you for a beautiful day.   
And then finally they heard the train doors close as they left Strathfield station. Once moving they also heard over the speaker system that the next stop will be central where this train will terminate and all passengers must depart from the train Thank you. 
Once off the train at central station Bill’s father was there waiting to pick him up,
“How was your trip” he said
Oh long and boring dad I stupidly forgot to buy a book to read and they sold nothing on the train.
Oh said bill’s dad Harry whose sister is Meredith from Brisbane
Once at home bill brushed his teeth and went to sleep
The following morning bill’s father went off to work in the city,
Bill’s sister Josephine went off too university at Sydney university. 
Bill’s mother had taken 2 weeks leave from work after a very busy time not long before bill went to Brisbane.
Bill got up at 10am and had some weat-bix for breakfast and his mom walked in and asked him “so how was Brisbane”
“Oh good” said bill in a rather down and depressed voice
Bill’s mum Louise looked at bill, hey honey, “what’s wrong?”   
“Ok” said bill “Brisbane was good mum, but yesterday on the train home a lady made me dress up as a girl for the entire day.”
“Ok honey you must feel mortified do you want to see a doctor or somebody about it” said his mum Louise
“ No, mum what I would really like to do is to dress up as a girl here at home when dad is out of the house. “
“Ohhh” said louise, “well I guess I will have to think about it but I certainly would not say no.”
“Ohh good” said bill “because it makes me so comfortable, and I enjoy doing it, and its really only clothing nothing permanent” 
“Oh well that makes me feel better” said louise
Thanks mum
2 weeks latter Louise walked in to bills room while his father was down the street walking one Saturday morning buying a paper
“Hey bill,”
“Yes Mum” said bill
“I have thought about you wearing dresses around the house and done some research on the internet and have decided that I don’t have a problem with it. They seem to say on the net that it brings boys and their mothers closer together and it keeps boys under control.”
“Ohh” said bill
So bill and Louise and Josephine went to bondi junction to the mall to buy bill some new clothes and make up to wear around the house while his father was not home. They bought 4 dresses, some makeup, 3 bra’s a few pantyhose and some high heels. 
On return from Bondi they found a note on the kitchen table that said “sorry guys I have been called into the city on work- it was urgent I hope to be home around 4- 4.30pm. Louise looked at her watch well its only 11am now that gives bill plenty of time to dress up in his new clothes.
They were all excited, bill ran upstairs and quickly put on his bra, panty hoes and wig and then got a blue dress and put it on and went down stairs to see if louise or joesphine could do his makeup.
He entered the TV room to find on the couch a pink long dress with buttons at the back that was big enough for him and then Lousie and joesphine entered the room and Lousie said “no bill you can’t wear that dress you need to wear this pink one”
Ok mummy he said and he slipped off his dress and he began putting on his new dress then joesphine started to help him do the buttons up at the back and once he had it on he looked rather pretty joesphine did his makeup and bill slipped on some high heels.
He looked very much like a girl, as Lousie and joesphine admired him, “all we need now is a name said Josephine.”
Bill shot up with Lucy and lousie and joesphine looked at each other and agreed yes Lucy was a pretty and fine name for there knew daughter/ sister.
Then they heard a nock at the door- joeshine went and ansered it. It was Charlie, one of bills friends. “Is bill right to come to the mall” he said
Joesphine, being very carful not to open the door to far looked around at Lucy and lousie and they were both shaking there heads in disagreement. Joesphine told Charlie no sorry bill is sick in bead with the flu and you wouldn’t want to see him in risk of catching it yourself Ok said Charlie but bill wanted to go to the mall. He tried to get the pink dress off but couldn’t. The door was closed by Josephine, and bill kept trying sorry Lucy but once you are in that dress you can’t get out of it by yourself” said Louise.
“Oh” said bill “but I want to go to the mall with Charlie,”
“Well not until your room is clean” said Louise
Lucy turned around and went upstairs and started cleaning her room, soon after that lunch time rolled around and Lucy was called down stairs by her mum for lunch.
They sat down at the table to eat lunch and during lunch Louise said “this is going to be quiet fun having 2 daughters”
Yes said Josephine “this is going to fun having a sister and a brother” 
After lunch Lucy returned to her room to continue cleaning it up. Eventually her father returned home from the city- as he got the train home and then walked, and Lucy was playing music and her room was on the back side of the house she did not see, or hear her father, Harry had come home from work in the city.
Lucy went down stairs to see if it were possible if Lucy could get a pink donna cover for her birthday in 3 weeks time to find her father immediately at the bottom of the stairs.
“And who is this may I ask” said Harry.” Harry this is your knew girl boy called Lucy, but when not dressed as a girl its only the standard bill.”
“Ohhh” said her father “and when did this all start” said Harry
“Ahh on the train home from Brisbane I was forced to dress as a girl by a lady dad” said Lucy.
“Ohh” said harry
“Yes and I noticed something was up when he was depressed the day after he got home and he told me and its really only clothing and makeup” said Louise
“Right” said Harry
Then Josephine appeared and said year and mum and I appreciate having another girl in the house at times and it means her bed room is kept spotless.
“Well it looks like there are a number of benefits and if it stays inside the house no negative effects, we will just have to remember where we are when we speak to you lucy/ bill” said her father
  “So does that mean you don’t have a problem with it dad” said Lucy
Well I do said Harry but I reckon I will get over them with time and seeing you dressed like that said harry
“Ohhhh gooooooooodddddddie” said Lucy
From that day on when inside bill was actually Lucy and the family lived a much happier, cleaner and closer lifestyle than beforehand. 
I don’t know all the American cities very well at all and it is safe to assume that Americans and others don’t know the Australian cities and towns well at all either so here is a quick rundown. I also find when I Google something in reference to the USA, I find 2 or 3 of the same place- which makes it rather complicated to find out, understand where the story is coming from ect.
These places are all on the east coast of Australia
Brisbane- state capital of Queensland [or QLD for short]
Roma street- is where long distance trains depart from in Brisbane, Not being from Queensland I don’t think there is a suburb called Roma street but there may be a street somewhere nearby called Roma street as Roma is a  big town in central Queensland.
Taree- is a big town in NSW, on the railway line
Sydney- is the capital of New South Wales [or NSW for short]. NSW is the oldest state in Australia I think, its certainly a state – Sydney and Brisbane have sporting matches against each other all the time and so do QLD and NSW.
Strathfield- is a main station on the inner west, south, western and north shore, New Castle and Central Coast Railway lines, Strathfield is probably a suburb of Sydney- when in Sydney I don’t spend much if any time near there.
Central is clearly the central most station of the Sydney railway system and the original NSW railways system but is now basically the centre of passenger transport for the Australian railway system. Central is also on the southern end of the original Sydney CBD, today Sydney also has other business districts such as North Sydney, Parramatta, Chatswood- these are all big suburbs, all on railway lines [thank god]
Bondi Junction is a suburb on the southern side of Sydney on the coast which has a big mall known as a Westfield’s- they have a heap of specialty stores as well as the general larger brand name stores as well.
If you Google Sydney, Brisbane and zoom in on the map you will get an understanding of where these places are and thus a better understanding of the storyline
In Sydney we have cityrail- so if you want Google Cityrail + Sydney and our metropolitan railway system for Sydney will come up- and thus a better understanding of where Bondi junction and central and Strathfield are.
tightskins tightskins
26-30, M
4 Responses Jan 1, 2012

This is not a story but a dream to live such a day ....
Wonderful story ...

I was a boy like to dress up as a girl that is what i wanted to be i like wearing dresses, pantyhoses, panties, wedding dresses, cocktail dresses, nightgowns, pj's, high heels, lingeries, leggings, tights, bathing suits especially bikini's, and fishnets.

thanks year I completely agree- I would love to see boys having to wear dresses for a summer or something to complete high school.

thanks for the likes all <br />
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for those who were wondering this is unfortunatley a fictional story- but if u read my above comment from the 3rd jan 2012 you will understand where I got the idea from

Love the story.

thankyou- its my first story. The inspiration for this came from me getting the train down to the big city- and reading stories off www.petticoatdisciplinemonthly.com and wondering what would happen if another cross dresser realised what I was reading and made me cross dress [which I would have no problem with]. SO thus I decided to write a story about it as I have not read such a story and I think its always good to read something different than the last story that you read.