My next door neighbour when I was growing up was Mrs Jones. She was a fairly young divorced lady in her early thirties, a little chubby but her face was beautiful and she always dressed incredibly sexily.

I remember noticing her clothing when I first saw her. She would always wear short skirts and dresses with pantyhose and a pair of little heels. I adored the outfits that she wore and would often watch her from my bedroom window.

This was during my teens when I was around sixteen or seventeen. I got a paper round to make some money which meant I would often walk up to her house and past her bedroom window.  A few weeks passed by and I had only seen her once on my round, in the garden wearing some mini cutoff shorts and a shirt which she had tied around her stomach, exposing her cleavage. 

I decided to change my route so that her house would be the last one I delivered to. A couple of nights went by without a change until late one evening as I walked past her window, there she was, getting undressed. 

She saw me instantly, covering her boobs with her hands, standing basically naked except for a pair of pants and some sheer pantyhose. I blushed and turned away walking up to her door and posting the newspaper through the mailbox. 

I heard her open the door as I walked off down the path.

"Hey, come back here, I want to talk with you!" She called out. 

"Don't be shy, come on."

I wandered back my face red with embarrassment. She invited me in and made me a glass of chocolate milkshake. We sat for a while and she asked how long I had been admiring her. I came clean with her explaining how I had always liked her clothing and how she dressed.

She sent me home but asked me to visit her house early the next day so we could talk some more. She was really nice and made me feel good. I had never found a woman I could talk to so openly before and it felt really special to share my thoughts and feelings. 

The next day I ditched my paper round and went straight to her house. I rang the doorbell in anticipation, delighted to see Mrs Jones meet me at the door with a big smile. She was wearing a tight black suit dress, pantyhose and some cute black ankle boots. 

She made some milk and cookies and we sat and talked about clothes for a long time. I asked her questions about lingerie, what a basque was, how to put on stockings, what heels go with what outfit. She was keen to teach me all about dressing in women's clothing. 

It was getting late and I had to go home. She hugged me goodbye and told me she would have a surprise ready for me tomorrow. I asked what it was, but she wouldn't tell me.

When I got home, my family were all watching tv in the front room. I walked into the kitchen and saw a shopping catalogue on the table. I felt an urge to flick to the ladies clothing section and began browsing looking at all the outfits.

I daydreamed about all the different types of dresses and nighties, shoes, skirts, stockings and sexy lingerie. My cock was digging into my flies and clearly protruding through my trousers. 

I snatched the catalogue and ran into my room, whipping my dick out and tugging at it as I sifted through the pages. I was so turned on pretending I was going to buy all the different garments and dress up like Mrs Jones. 

My cock exploded shooting streams of hot sticky cum halfway across the room. This was my first memory of cumming and I loved it! All night I dreamed of dressing in girls clothing, imagining all the outfits I could wear. 

In the morning, I snuck out early and headed next door. I wandered past the window and saw Mrs Jones getting dressed. I was mesmerized as I watched her adorn her brassiere. She turned, winked at me and pointed to the door. 

As I entered the house I noticed a collection of bags on the kitchen table. Mrs Jones had been shopping and told me to take the bags to her room and choose an outfit. My eyes lit up as I grabbed hold of the bags and skipped to her room. Upon opening the bags, I discovered a large range of clothing including several bra and panties, skirts, tops, stockings, shoes and wigs.

I picked up a pink pair of panties and slid them on over my stiff cock, then I slipped on a brassiere and a pair of pantyhose, rolling them up my legs the way she had described. I didn't have much of any hair on my legs and the feeling of nylon smooth against my skin made my dick even harder.

On the bed, I had noticed an elegant white bodycon dress. I pulled it up my legs and over my bum, feeling my cock rub against the fabric inside my panties. A shiver ran up my spine, and a tingling sensation as I looked in the mirror at my own body in this sexy outfit. I wandered back to the bed and saw a pair of pink pointed court shoes and a brunette curly wig.

I adjusted the wig in the mirror and took a step back, staring at the sexy girl that stood before me. I couldn't quite get used to the heels and lost my balance a few times almost falling onto the bed. I heard a knock at the door and Mrs Jones voice softly speak.

"How are you getting on, baby girl?"

"Ok, I think?" I replied. She entered the room her mouth a gaze as she stared and smiled at me. Finally, she spoke again.

"You look so beautiful, baby girl. I always wanted a daughter but my ex-husband didn't want to have any kids. Oh my... you really are so cute! Come with me, I want you to help with dinner."

I followed her back to the kitchen, watching her walk and trying to mimic her movements. I had started to get the hang of the heels as I helped her prepare the food. We sat and ate, talking about clothes, shoes, hair and makeup. She said she would help me to become a real girl and that I could come over to her house any time to dress up. 

After the food, I helped her wash and dry the dishes. We sat down and talked some more until it became dark outside. I had to go home but I didn't want to go back to being a boy. She told me I could keep the panties and bra and wear them underneath my clothing so I could feel a little more girly.

When I got home I went straight to bed. I rubbed my legs together and ran my hands over my body feeling the soft panties and silky bra. My cock was rock hard and I couldn't help but jerk off in my panties, filling them with my sticky cum. In the morning I woke up feeling different. I knew something had changed and no longer felt like a boy.

From that moment on, every day after school I would visit Mrs Jones to dress up and help her with the chores. It felt so freeing to wander around her house dressed like a girl, pretending I was a girl, thinking I was a girl. We even came up with a new name for me, Tatiana. I always loved this name and as I grew older I began to think of myself as this new person.

I had started to change over two years and by the time I finished school I had began to think of myself as Tatiana more and more. I grew my hair long and stopped cutting my fingernails. Mrs Jones had taught me how to shave and wear makeup so that I looked more feminine and we would often take pictures or make videos of me.

I had become a little bit of an exhibitionist and loved posing for the camera every chance that I got, feeling a sense of confidence as I strutted around her house. One day after one of our photo shoots, Mrs Jones invited me to go shopping with her. I had never left the house dressed up and was really nervous about being seen by someone I knew.

She reassured me and told me we would go out of town to a mall in the next city. I had let her choose my outfit which she had done very well. She had picked out a floral frilly hem dress which accentuated my curves and hid my penis. We stepped out of the car and we walked towards the shipping mall, heading for the ladies clothing stores.

A few men stared at us, but she told me they probably just wanted to fuck us, which made me smile. When we got to the first store, a woman greeted us and asked if we needed any help. Mrs Jones did most of the talking, asking if they had different colours of dresses and what size heels they had in store.

We picked up a few different items and heading to the dressing rooms. None of the female staff blinked an eye as I wandered into the ladies changing room and I remember feeling really naughty as I tried on the various outfits. After choosing a few to take home, we paid the clerk and then as we were leaving she said something I'll never forget.

"I hope you and your daughter have a great day!"

From that moment on I knew I would be living the rest of my life as Tatiana.