A friend in need ST110 (Part 1)


As Kris started to wake up he couldn’t help but feel like today was the day, he was going to go out to the shops and buy

himself a bra, panties and a dress, all on his own. When he go up he showered, freshly shaved, put on a pair of clean
knickers and a training bra.

At the shops his heart was pounding by now, as he approched the first shop he was really scared by now and asked the shop
assistant to help him find a dress for himself. She said
“Sure I’ll help a boy with dress hunting, what are you looking for?”
Kris replied “I’m looking for a dress that comes below the knee and will look lovley with my skin tone” with a blush
“Ok I think I have the perfect dress for that, come with me, my name is Lucy”
“I’m Kris, nice to meet you”
“I’m curious, your a boy why are you looking at dresses?” Lucy asked
“Well I love dresses and other girly things, like right now I’m wearing a training bra” Kris replied
“Are you?” Lucy said rhetoricaly “Well I love a boy to embrace his inner girl”

Once Kris found his dress he asked to try it on,
“Can I try it on, please?”
“As you asked so nicely, I’ll help you” Lucy said with a smile
While Kris was getting into the dress Lucy noted that he makes a beautiful girl and was determined to find out more
“So Kris, would you like to come back to my place?” Lucy offered
“I have to get a few more bits but I’d love to, where shall we meet?”
“I finish about 4, theres a coffee shop near by we could meet there”
“Ok see you then, thank you for the dress”
“aww thats ok sweet heart”

Next on Kris’ list was a bra and some knickers so it’s off to La Senza. Kris always dreaming of coming here now that he his,
he couldnt be happier, as he walked in he instanly saw the perfect bra and pantie set. it was red with a floral emrodded
overlay. He went up to a shop assistant and asked to be mesured for a bra, she was shocked at first but simply said
“Oh is it your first time sweetie, I can help you follow me”
Kris followed her to the back and told him ‘arms up’, she put the tape measure around his chest, then she measured his
brests. After that it was now time to buy his first proper bra.

When Kris was done shopping he looked at his watch and it was 3:30, so he had half an hour to go and buy some shoes, he
bought the cutest shoes. It was a low heel, red mary janes. He looked at his watch and it was 4 o’clock so he rushed to the
coffee shop and saw Lucy there. After coffee and a little chat it was off to Lucy’s house.

At Lucy’s house Kris told Lucy about his dreams and desires, they went in this order;
1. To be a giddy school girl
2. To be a ballerena
3. To be a cheerleader
4. To be a sissy maid
5. To be a baby girl
“Realy, wow I guess we could start you off a baby girl, then you can meture into a young woman, how’s that sound?”

To be continued…

Shopping trip 107 (Christmas)


This is my top all time fantasies 🙂

It’s coming to Christmas and sissy kris needs a dress for the Xmas party.

So when kris woke up and had breakfast in bed, then decided to have a bath, shaved and got dressed in a t-shirt and leggings with a 2 inch heel flats. Once out he went straight to Victoria street for some underwear. Then it was off to try on some dresses, first he went into next and asked the shop assistant that he was buying for himself and would like to try on some dresses and asked for her help. She must of known he was a boy. ‘my name is Clair’

Clair asked if he was what she expected and with a simple answer and that was ‘yes I am’
‘ok now we don’t get many people like you in our shop, now what are we looking for exactly?’
‘well I am looking for a knee-length, off the shoulder dress in red and some three inch heels’
‘wow for a guy you really know your clothes and red will definitely suite you, come this way’
‘can I quickly use your toilet’
‘sure follow me, do sit down I know you boys can be messy on the seat’ she said with a smile

Once I done my business it was time to try on the dress and shoes, in the changing room Claire help me into the dress.
‘you look beautiful’
‘thank you’ I replied
‘now let me help you take it off’
Once out of the dress we went and paid for it, Clair said that I can have it for free.
‘I’m not doing anything later why don’t you and I go to my place and we can have a little fashion show, how’s that sound?’
‘I’d love to, what time?’
‘I finish about 5 so come by then, or you can help me with the shop’

So when it was 5 o’clock we went back to her place and had a coffee and told me to follow her. So in the bedroom I was told to strip and put one of her nighties on including panties and a bra all in red, then we started to make out and had great sex.

‘so why don’t we go and get some coffee and then do some food shopping?’
‘I’d love to, but what will I wear?’
‘oh I have that one figured out. You can just wear my clothes from yesterday’
‘thank you Clare’
‘no worries’

The end

Look out for my next instalment of the ST stories