Dressing With An Old Friend
by Malcolm (UK)
It was 1970s I was 18 and a bit of a loner. I had tried without success to find a girlfriend but always felt inhibited and awkward around girls, lived with my parents and had a secret, I was a closet crossdresser.
I had gotten into when messing about with my school friend Steven round at his place. We had tried on some of his sister’s bras and panties. It got as far as jerking off together.
We did it a couple of more times until he went to another school and we lost touch. I hadn't seen him since we were 13. I continued to sneak my sister's undies and even tried on dresses when everyone was out.
I was in town with nothing much to do when I bumped into my old friend. We went to a cafe and chatted about old times but neither of us mentioning 'that' subject. He now had his own place in town and I accepted his invitation to go see it.
It was a nice flat above some shops. As we chatted I wondered if I should say something. He hadn't so far, maybe he had forgotten about it.
'Do you still wear panties?' he suddenly blurted out.
'Yes' I answered relieved to have it out in the open.
'Me too' he smiled and we both giggled.
'Follow me' he said and led me into a bedroom.
It was decorated in reds pinks and lilacs rather over the top with drapes and cushions on a large bed. He opened a drawer full of panties bras and other lingerie. On a dressing table I saw makeup, powders, lipstick and so on.
I was agog at all this stuff, like I had entered another world.
He watched me smiling. 'Well what do you think Malcolm?'
'It's amazing' was all I kept saying.
He laughed 'So do you want to dress up with me?'
'Oh yes I'd love it'.
'Good, let’s get rid of our nasty male clothes' he said in an effeminate voice.
I followed suit 'Oh yes, horrid rough boy clothes, Yeuk.'
As we undressed I realised Steven had been wearing black panties stockings and suspenders all this time.
When offered I chose a bra panty suspender set in lilac. We giggled as he helped me dresss, both of us now had erections and we made jokes about it. Steven put on a shiny black cocktail dress.
He took out pink satin frock suggesting it would suit me. The time just flew past as 'Stephanie' as he liked to be called did our makeup. The crowning glory was when 'she' produced two wigs, a black bob for him, and blonde curls for me.
'I think your more the sissy type malcolm' he observed .
I had never thought about the different aspects of crossdressing before but I realised Stephanie was right.
'I used to have another sissy girlfriend but she moved on' Stephanie said as she took out a chain choker and fastened it around my neck. I stared at myself in the mirror and the word sissy now adorning my neck.
Stephanie kissed my neck and ran his hand down my front stroking my crotch.
'Wait here a while' he said and disappeared into the lounge. I thought I heard her on the phone. I was left to revel in the transformation I had undergone. I fingered the collar and the metal 'sissy' emblazoned on it.
'I need a coffee, come through' Stephanie's call snapped me out of it.
I went through stepping carefully in the pink heels she had chosen for me. I paraded about a bit and then we sat and talked as we finished our drinks. Stephanie moved in close and kissed me on the lips.
'You're so pretty my sissy, do you like it?'
'Yes thank you, I've never dressed fully before.'
'Feels natural, doesn’t it?'
I was startled by the sound of the doorbell.
'It's ok, I've just got someone who'd like to meet you'.................
Do you want to share your incest/taboo stories? Simply click here to Submit A Story