How I Became Me - Sex Stories

How I Became Me

... expanding collection of shoes and boots. My socks and pants were moved to the bottom drawer whilst the top drawers were full of pretty knickers and tights. When Mum brought home my first training bra I was a little embarrassed but couldn’t wait to try it on. With a little tissue padding it gave me a hint of cleavage to go beneath a figure hugging dress. As a special birthday treat Mum took me shopping. I was now 16 and was nearly as tall as Mum. “Anna, take of that dress and put on a pair of jeans, we’re going to buy you your first pair of heels.” “Oh, thank you Mum. But how can we do that. Wouldn’t it look strange with a boy trying on women’s shoes?” “Don’t worry. Our feet our nearly the same size now. I’ll try them on. If they fit me, they should be fine for you.” At the shopping centre, Mum let me choose the shoes I wanted and then asked the sales assistant to bring her a pair to try on. As I watched Mum slide the shoes on to her feet, I couldn’t wait to get them home and practise walking around the house in them. “How do they look son?” “Very sexy Mum.” “Good,” turning to the assistant, “We’ll take them.” And I walked out of the shop carrying my first pair of heels. “Of course when a lady is wearing high heels, to be properly elegant, she shouldn’t be wearing tights, she should be in stockings.” “But I don’t have any stockings Mum.” By the time we got home I was carrying my new shoes in one bag and another bag with a lacy, black suspender belt and a silk pink one. We’d ...

... also bought three pairs of stockings – a pair of seamed barely black stockings, a pair of 7 denier nude stockings and a pair of white fishnets. I was so keen to try out my new shoes, I pulled my jeans off and without removing my socks I tried them on. I loved the way they stretched my calf muscles and my butt checks felt firmer than usual. “Oh Anna! Where are your knickers? I can’t believe you went out shopping with me dressed like that.” Mum had always been relaxed with nudity around the house. When I was dressed as Anna she had no qualms about me walking in to the bathroom whilst she was in the shower, but it had been a whilst since she had seen how puberty was affecting my body. “Sorry Mum. So what do you think? Do you like the effect this shoes have on me?” “Well they certainly make the best of your legs … and it looks like they’ve got you a little excited!” I looked down and realised what she meant. My cock was poking straight out quite proudly. “Go upstairs and sort yourself out. We can’t have you walking around like that and put on a pair of knickers. Why don’t you replace those socks with those new stockings? If you need a hand adjusting them, just shout down.” So I went upstairs, sorted out my erection and tried my first pair of stockings to go with the new shoes. When July and Macy got home they complimented me on my more mature look. They gave me a few tips on walking in heels and took great pleasure on watching my wobbling attempts to walk demurely. “You need some ...