Jane091
06-06-2012, 06:35 PM
Well today was not the first time I've crossdressed (I have managed to wear some of my mum's clothing when alone in the house) but today was the first time that I've actually worn whole outfits (without female underwear sadly) AND makeup.
Those who read my previous thread will remember me talking about my female friend and our shopping expedition together, unfortunately that was months ago and due to various reasons and seemingly like the gods were themselves conspiring against me it was only today that I was finally able to go to her apartment.
We hung about for a bit and then finally she asked the question of did I want to dress, it was a bit awkward at first she told me to just take whatever I wanted out of her wardrobe but her light was broken and I couldn't see properly but eventually we managed to find the black dress and the tights which I had bought before and she also pulled out other dresses, tops, skirts and belts for me to try on.
She left the room when I put on the black dress and the tights and I have to admit I felt rather silly when I showed myself to her but she was very complimentary especially about my figure.
She made me feel at ease, I tried on various outfits my favourite being this short sparkly blue dress which looked great on me (if you were ignoring my neck upwards ha ha) especially when she got tissue paper for me to stuff down the front for boobs. She also put makeup on me but it wasn't much just some foundation, blush and lipstick, only the lipstick was really noticeable but I saw some potential if I had a proper makeover and sorted out my hair I may actually pass. She also gave me a necklace and some wrist jewellery to wear. In terms of footwear I tried both high heels and boots which also had heels, have to say it was very strange wearing heels and whilst I didn't fall over it was hard to walk in them.
This whole experience lasted about an hour, I was able to easily remove the makeup and went back to boy mode. I am eternally grateful for her for letting me have this experience but she definitely enjoyed having her own dress up doll.
Those who read my previous thread will remember me talking about my female friend and our shopping expedition together, unfortunately that was months ago and due to various reasons and seemingly like the gods were themselves conspiring against me it was only today that I was finally able to go to her apartment.
We hung about for a bit and then finally she asked the question of did I want to dress, it was a bit awkward at first she told me to just take whatever I wanted out of her wardrobe but her light was broken and I couldn't see properly but eventually we managed to find the black dress and the tights which I had bought before and she also pulled out other dresses, tops, skirts and belts for me to try on.
She left the room when I put on the black dress and the tights and I have to admit I felt rather silly when I showed myself to her but she was very complimentary especially about my figure.
She made me feel at ease, I tried on various outfits my favourite being this short sparkly blue dress which looked great on me (if you were ignoring my neck upwards ha ha) especially when she got tissue paper for me to stuff down the front for boobs. She also put makeup on me but it wasn't much just some foundation, blush and lipstick, only the lipstick was really noticeable but I saw some potential if I had a proper makeover and sorted out my hair I may actually pass. She also gave me a necklace and some wrist jewellery to wear. In terms of footwear I tried both high heels and boots which also had heels, have to say it was very strange wearing heels and whilst I didn't fall over it was hard to walk in them.
This whole experience lasted about an hour, I was able to easily remove the makeup and went back to boy mode. I am eternally grateful for her for letting me have this experience but she definitely enjoyed having her own dress up doll.