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.

IsaacNewton IsaacNewton
60 Responses Feb 5, 2008

What a beautiful opening to this part of your life - very very envious

I agree with you.Louise CD

Great feelings and emotions your share here.I feel you in your text.
Louise Cd

what a beautifull story, its what only a few have only dreamed of really happening and dream of secretly.were you able to stay in touch with her or her sister and ever return for visits? surely you must have yearned for their company over the years im sure. thanks for sharing it was an endearing letter.xo howlin.

Many thanks - your account confirms what a "frustrated housewife" told me - many women long for a man with whom they can share their love of their clothes - better still if they are into sharing sensuous vintage lingerie.

Beautiful story. I wonder if that box was really in the hallway "just incidently"?

I would like to have been in your position. What a wonderful way to find out about yourself. Iwas just starting to have ideas along these lines in the late 1970s, but I had to find out by myself :(

I loved your story and please write about the land lady's sister and the hot time's you and her had dressing up to play.

what a wonderful woman,your lucky to have found her

Great story, please tell us more.

Love this story, feel free to add to it whenever you can.

Great story. I would enjoy that very much. Thanks for sharing.

I just wish that I had had a landy similar to yours. You only need a little encouragement. I for one would love top hear some of the 'mother- daughter' stories please. Have a great time.

A wonderful story and so very well written. I do hope that you honor us with many more of your experiences.

i adored the story and u were that gurl ! so special .<br />

That was a nice story.

The only thing that could be better than the story is experiencing the real thing. Please write more.

What a great story. Was there much sex with the landlady?

This was a wonderful story and just the kind I love to read. I look forwarf to more. Diane

that is an awesome stories kinda wishedit happened to me.

Wonderful, wonderful story, please write more, love Steffi xx

Fantastic story! Even now it would be wonderful to be dressed by such an understanding lady. not to mention , having a sexy sister, what a combination! So many guys seem to be with a partner who maybe does'nt mind' but it would be so much better if it became the "norm" rather than almost a favour. Love to hear some other stories you mentioned.

Loved the story. Such a pity that you can't indulge these days. Oh what a time could be had with an enthusiastic partner!

What goes around comes around.<br />
Recently my wife found my wardrobe of clothes I came home to fins she had everything laid out on the bed.Saying I knew you were interested in female clothes but had no idea it was so important to you. Why have you not told me about the urge to dress up.<br />
I could only stammer that I was afraid I would lose you, as I love you so much.<br />
What is your girl name I said carolyn. I want to see you fully dressed everything makeup hair shoes ,you must have some ive not found yet.Get ready and meet me in the lounge.With those words echoing in my head I prepared for I did not know what.<br />
Showered shaved body hair too all gone. Then white bra panties suspender belt tan stockings <br />
kne length satin slip Just alight make up pink eyeshadow brown mascara blusher and lipstick to match. then a pale pink nylon logsleeve pol neck blouse and a black skirt knee length a wide black patent belt nipped my waist in. Shoes black patent 3 " heel. I did not want to be too startling at this first outing to her was not to scare her. I was so afraid of her reaction. <br />
No doubt she had seen the more sexy extreme outfits that I like too.<br />
tentavely i mad eway to the lounge where she was waiting a neutral look on her face .I was ordered to walk around and pose so she could see all. I showed he rht eunderwear everything .<br />
Cant say I approve she said but do you go out dressed like this. I had to admit I had when she was not around.<br />
You will stop doing that right now she demanded I will tolerate you dressing up some times but you keep it private.<br />
My relief of her not throwing me out or leaving herself was such arelief I agreed to all she asked .<br />
I have to say that she has changed her dressing style to be more upmarket aven sexy says I will not be upstaged by you.<br />
I am happy eith the arrangement and get to dress more and more as the months pass.<br />
She says she doesnt feel threatened by my femmininnity.<br />
So I am very careful not to upset her.

How fortunate for you, Carolyn!

Wonderful land lady. Thank you for sharing. I look forward to reading more.

A great story, thanks for sharing!<br />
You were very fortunate, to meet such an understanding and openminded woman.<br />
<br />
Please write more if you have time.<br />
<br />
<br />

I know the feeling, had a neighbor just like that!

Absolutely LOVED your story, it is like a cross dresser's fantasie story. <br />
<br />
You said that you don't have time now, families grow and what have you. The future will find you dressing some, with 99.99 % of people it never leaves.<br />
Good luck

A dream come true. You were so fortunate.

What a great life you fell into! Please write more. You write in a very pleasing and enjoyable manner. How has your dressing grown and changed over the years?

thank you and uplifting story thats u take care

WONDERFUL story. LOVED it. i had a similar experieince. lucky you tho. share more stories about your adventures? sounds amazing. NEVER boring. thanx for sharing this one.

I can relate top your story so well as I had a landlady who took me in hand with dressing etc for a wonderful 2 years.<br />
I have never lost the urge to dress and do so asoften as I can.<br />
Such a pity you cant indulge I sympathise with you.

wonderful story and memory... loved the rich detail and emotion! I was fortunate to enjoy similar adventures with my mother...

This is indeed a wonderful story. How lucky for you!! Yes, Please I would luv to see some more stories about you going out crossdressed!!! Jamie

I'm jealous and hot now!

What a fantastic story and well written, it touched my heart.<br />
What a wonderful woman she was to you. you are blessed.<br />
<br />
The bit that jumped out to me is when you said 'I felt so snug, warm and feminine dressed like this'<br />
I get that feeling as well.<br />
<br />
What feelings did you get when you seen yourself for the first time in a reflection of a shop window while you where out dressed up.<br />
<br />
These memories are to treasure forever.

Such a wonderful story. Like all the previous comments I wish it would've happened to me also. It is truly a shame you currently aren't able to indulge your femininity! I well remember that "empty" feeling one has when only able to dress in the "yucky" clothing made for the male gender! I went through a 25 year period of forced abstinence also and actually had forgotten my feminine needs-desires. Once our children were finished with college, married and out of the house my wife decided she no longer wanted to have physical sexual activity. It was about this time my employer asked me to travel periodically on overnight and sometimes week long business trips. I'm here to say that my feminine needs came back like an explosion my first night away alone in a hotel. How wonderful that there was a huge mall connected to this hotel so I was able to purchase a silky, dual la<x>yered, nylon floor length negligee/peignoir set with a huge sweeping full skirted gown and robe in a very pretty pale pink. Next I guessed (correctly it turned out) at a white nylon satin strapless bra and a 1/2 dozen silky panties. This blew my expense allowance for this trip! Back in my room I eagerly tried everything on and luxuriated and slept every evening in my pink negligee and bra stuffed with my socks. Panties were worn every day under male pants. I've shared this with you to give you hope that you will be able to "dress" again. While my wife did discover my femme things and absolutely hates the idea I am a "closeted" partial crossdresser at the age of 70!

loved your story,what a dream come true

this is great story... i hope to meet such a lady one day

What a wonderful experience for you .I love dressing but never had anyone to encourage me or help me to perfect my femme look

What a wonderful story. Some of us have a great luck....

My mother use to buy me panties, once she knew I like to wear them. She bought me a pink babydoll nightie with some of the money I had saved.

Please ad more stories! I would love to have a woman dressing me.

Great story, and what a lovely introduction to cross dressing it must have been.

Hi dear, everyboy has his own story and yours is marvelous. It is hard not to be jealous so I will console myself and get dressed

A truelly great story. thanks for sharing it with us. It would have been lost otherwise.

you lucky guy

nice story dear

wish it had been me

lovely story. saddly I only get to dress when my wife and kids are away.

lovely story. saddly I only get to dress when my wife and kids are away.

Like all the others, I am sooo envious. Your landlady was absolutely perfect. Did you ever kiss her? I would have loved her dearly. I do wonder about the sexual issue you mentioned regarding your landlady's sister. I would also love to hear about your trips about the city as mother and daughter. Your tale is so interesting and so well told.

that story is the best one and i wish i had more confidence in me to dress all the time

Wonderful story. I wish it had happened to me !

I thought it to be a wonderful story. One that for me personally would only be a dream or fantasy. Thank you so much for sharing. Hugs

Now that you've told us there are more interesting stories, you cannot cut people off cold! Send them on, when you can

thats amost faboulous story if only it had happened to me when I went to university I may not have as many hang ups as I have now

I wish I had that tpye of experience in my life

oh my, thats so amazing. what a great experience, would love to hear more esp about the landlay's sister

No, sadly I rarely get to indulge. Kids, disinterested partner, mortgage etc. They all combine. So I reflect on better times. Memories can be a refuge.