A Little Help From the Landlady
It was the late seventies and I was 16. I had to move towns to complete my university entrance years (11 and 12). My parents found board with a divorcee, a lady in her 40's living alone in a large house in a well-to-do suburb. She was very kind although a little highly strung at times, testament to difficult times prior to separation I think.
Anyway, it all started with a box of clothes which had been placed in the hallway downstairs, outside my room. I had noticed it over a number of days, including the folded tweed skirt suit on the top. For some reason, I developed the desire to try it on and so, one night, after my landlady had retired upstairs, I grabbed the box and took it into my room. Donning the outfit, I had erotic sensations which included an emission. I felt immediate guilt and returned everything to its proper place, vowing never to repeat this episode.
The next evening during mealtime, my landlady asked me if I had touched the items in the box. It was so sudden, so unexpected that I froze, unable to choke out a response. This I think was taken as a confession. She quickly changed the subject and we talked about other things.
The next evening, whilst watching television, she asked me straight out whether I liked 'pretty things'. I stammered out some sort of reply, a guarded affirmative but non-committal. After a pause she told me to follow her. We ascended the stairs and entered her room, which I had hitherto never frequented. Bidding me to sit beside her on the bed, she asked whether I had ever dressed as a girl. I answered that I had not. She asked whether I had ever wondered what it would be like. I simply nodded. Without further ado, she said she would like to give me that opportunity. Sensing my agreement, indeed probably my excitment, she told me to go *****, shower and return in a pair of silky pink panties which she now placed in my hand.
At 16 I had little body hair and was pretty smooth and slender. Once clean, I found that the panties fitted me perfectly, barring the tell-tale and increasing bulge at the front. I returned to her room and she immediately fitted me with a matching bra, assisting me with the hook and adjusting the straps to fit. She inserted 'chicken fillets' to give me some shape (her daughter's she said - who was currently working as a Nanny in Belguim) then helped me put on some pantyhose. I shivered as she rolled them up, explainng to me the method I should use when doing so myself.
Soon a white, lacy fronted blouse was passed to me. I struggled initially - the buttons being reversed! Then, to my surprise, she produced the grey 3 piece skirt suit from downstairs. The below the knee skirt fitted snuggly, although she noted a little bit more hip and tush wouldn't go astray, an issue she would address a few weeks later via a padded panty. We both laughed, easing some of the building tension that had become apparent. The waist coat was next and fitted nicely over the top of the belt of the skirt. All the time she fiddled and adjusted to get the best fit possible.
At this point, she sat me down and applied a tiny bit of eyeliner, mascara, blusher and lippy. Nothing extravagant, but enough to give me a girlish, feminine look. Looking into the mirror, I was surprised by the effect but even more so when she produced a small 'Bob' type wig and brushed it into place. A watch, a bracelet, small clipon earrings and a matching necklace completed things before I stood and she helped me into the jacket.
The reflection in the full length mirrow by the wardrobe was stunning. I simply couldn't get my head around what I had been transformed into. She guessed my surprise and hugged me from behind. She said that I had turned out far beyond what she had anticipated!
She pondered on footwear for a moment. At this point, I came out of my shell and admitted that I had always fancied high heeled knee high boots. I never understood the attraction, but it was very real. She smiled and nodded, saying they would be perfect. From the wardrobe she produced her own black knee high's with the stiletto heel!! And what a great fit!
The boots, once zippered up snuggly about my calves, disappeared beneath the skirt (to this day I love that effect and believe that boots are far sexier with longer rather than shorter skirts). Initally, I tottered about awkwardly but then soon adapted to the need for smaller, shorter steps. I loved the smooth sway of the hips that heels invoked.
She took me by the hand and led me downstairs; fixed us both a wine and led me out onto the balconey overlooking the river valley. I felt so snug, warm and feminine dressed like this. I finally found myself chatting openly and honestly with my landlady, revelling in the situation. She too seemed happier than I had hitherto known her - perhaps it was the loneliness of the past few years, but she now treated me like kin, gently offering hints, bestowing flattering comments and encouraging me to 'be myself completely'.
This went on for the remainder of my boarding time with her. When I got home from college each day she would have an outfit laid out upon the bed, not necessarily glamorous (although there were times she saw fit to do so) but feminine and comfortable. Dresses, skirts, polar necked tops, blouses, shoes with 1 or 2 inch heels were standard. Correctly matching underwear with nylons were insisted upon. Thus attired, I would complete my homework and study until called for dinner.
She tutored me in doing my own makeup, hair and nails. Moreover, she insisted that about the house I 'do it properly'. She took great pride in her second 'daughter', the one that her ex had nothing to do with!!!
We had many small adventures together; she concocting a number of scenarios with us posing as mother and daughter in public. Several of them could easily be written up as stories within themselves! (Let me know if anyone thinks its worth it. I don't want to bore you all).
When I finally graduated/completed my studies, she made a huge fuss by purchasing a lovely evening gown with all the trimmings. She took me to dinner at the best restaurant in town, accompanied by her sister (who had become an enthusiastic and - in a sexual sense - active party to the arrangement, although my landlady never knew). Anyway, It was a lovely evening; laughs were had, tears were shed and profuse thanks passed either way.
I still think of her and miss her dearly. She opened a door to a place which has produced so many many pleasant memories and I am so grateful.