My Life As A Crossdresser First Part

It started as I mentioned in a previous story with my piano/drama teacher when I was 17 - up til that point I had been a fairly normal ,if bi-sexually inclined teenager,
He opened up a whole new world of experiences for me so much so that I started to do it at home and family places whenever I could.
My fathers sister was 20 years older than me and lived about 10miles away in another town in her own house ( she was single and had never married- my sister and I suspected she was Lesbian, but had no real proof ) and we would stay with her on occasion sometimes together but more frequently it would just be me.
Aunt Anne was a a voluptuous woman who liked to dress well and had a lot of lovely clothes always welcomed us either together or singly to stay over with her, which we did on a regular basis ( she was our only relative)
On this occasion I went on my own as my sister was away with her friends on holiday in Spain...Aunt Anne greeted me off the train and as I was almost 18 took me to a local hotel for lunch, which consisted of quite a few drinks too!!!
On returning to her house a few hours later I was a little drunk and feeling a bit woozy, so she insisted on me lying down in my room for a couple of hours,as she closed the bedroom door she said she was going down the road to her friends house and would leave the number on the table if I needed her.
I slept for an hour or so, then got up to go to the toilet, passing her room on the way I saw the door ajar and peeked was empty of course- but I suddenly had the urge to see her underwear ( having seen some in the wash basket in the bathroom) cautiously I entered and went to the drawers beside her bed and eased them open in the 3rd drawer down I found panties,tights...AND stockings!!! - it was gold dust to me...I pulled out a pair of very sheer black panties and held them to my nose,loving the feeling of them and getting a huge erection at the same time!!!!
I delved further and found some shiny black hold up stockings with which I rubbed myself.... Unable to resist,I slipped on the stockings and panties and stood in front of her mirror then wanked off ..
It was wonderful and so erotic I came like a fountain all over the glass- then panic overtook me and I quickly got tsome tissues to clean up before putting the lingerie back where I found it .
Even though I thought I was thorough ,I must have missed some because Anne approached me the next day,asking if I had been in her first I denied all knowledge of it , but she persisted and eventually I confessed that I had been in there....
In my underwear drawers she asked gently....
I nodded unable to speak with the shame of being discovered !!
I knew someone had been in, I'm just glad it was'nt a stranger she said quietly
Do you like my undies Charles? She went on
Again I nodded to her
I was so embarassed I could barely speak,but when I did it all gushed out i told her all about my experiences with my piano teacher and how he had introduced me to women's clothing....then with some mild persuasion I told her I was also bi-sexual....she did'nt seem shocked at anything I said. And was very reassuring to me saying that it would be ok to do it whilst I was there ( but my dad would'ntt be so understanding!!! ) - I think I knew that because he was so straight laced!! -the upshot was that after a short while ,she invited me up to her room to look at some 'things' I might like .... Sure enough she had the drawers I had gone through open and was picking things out for me to look at, including the black panties I had worn
'I suppose you'll be wanting these Charles' she smiled at me
I managed to say 'yes please'
'I knew they had been worn ' she went on
Eventually she had sorted out a small pile of sexy lingerie for me to use - but there was a bigger shock to come...
'Why don't you try some on for me?'
'You mean now?' I replied getting excited
'Yes why not , then I can help if you
I took the pile of lingerie back to my room and with shaking hands selected the black panties,sheer hold ups and a lacy black bra.....I was getting hard just touching them...mmmmm
Anne called through 'are you ready yet'
'Won't be a minute ' I managed to reply
Feverishly I ******** off and drew on the stockings, my **** was aching by now !!!
Then with a little difficulty I put on the bra just before getting the panties on.
Anne came through the door as I stood up straight and remarked that I really suited black,being fair skinned
There was no way I could hide my huge erection and she commented on how big I was these days!!!
I looked at myself in the full length mirror and managed to smile.... To be continued

Sucker55 Sucker55
51-55, M
10 Responses Dec 15, 2012

Oh my!! I'm intensely turned on!!! Mmm!! Lovely story!!

wow very hot...please tell what happened next

VERY sexy story! Thanks for sharing.

Not into to dressing myself but a very sexy story and I would have dressed for her too. What a wonderful and understanding Aunt.

u have me all big and drippy in my panties

Great story, I used to wear my Aunts knickers and she caught me.

mmmmm yummy i wish i had an aunt like yours.

She was a very special lady

WOW!! cool aunt!!!

Yes indeed she is very cool

wow.............sounds like heaven on earth!

Great story and Aunt's are so understanding and obliging.