Ruby pulled the suspender elastic through my trousers and it snapped against my leg.
She looked at me with one eyebrow raised.
"Well", she asked with a wry smile on her face.
"Well what"? I replied trying to look innocent.
"Well young man, I'm no fool but I would say you are wearing stockings and suspenders under those trousers".
I sat there looking down like a naughty puppy, too scared to make eye contact.
"Stand up", she said, "Let me see".
"Drop your trousers Stuart", she said her voice quite firm.
I froze, I could feel my bottom lip trembling and I thought I might cry.
"Come on young man stop being a wussy and show me what you are wearing" she barked.
I undid my belt and fumbled with my button but my hands were shaking so much I couldn't undue it.
Ruby grabbed my trousers and pulled me closer.
"Do I have to undress you like your mother did"?
She undid my button and zip and pulled my trousers down to my ankles.
I thought she was going to go mad when she saw that I was wearing her daughters lingerie but she didn't.
"Are they my daughters"?
"Yes Ruby", I replied.
"Well, black is no good for your skin tone".
"Sorry", I replied.
"You are fair with pale skin, black is not your colour.
"Oh okay", I replied.
She went on, "You need soft, pastel colours, cool tones".
"Blush pink, champagne, peach, ivory, and silver maybe even powder blue"
"I like blue", I replied.
"I'm talking about baby blue lingerie not a football strip", she laughed.
"Come on, pull your trousers up my daughter has lots to choose from."
I pulled my trousers up and followed her up to the bedroom. Where she preceded to tell me about her daughter and how they had fallen out just before she moved to Spain.
"Do you think I'm a lush and a tart Stuart", she asked with a tear in her eye.
"No of course not Ruby", I replied.
"My daughter does"
For the first time Ruby showed her vulnerable side and she started weeping.
"Hold me Stuart, give me a hug"
I nervously put my arms around her and gave her a hug. I went to pull away but she pulled me closer.
I could feel her bosom rising and falling against my chest. Her perfume was strong. She was all women, the type that both attracted me and scared me at the same time.
It wasn't because I wanted to fuck her but because I wanted to be dominated perhaps even mothered by someone like Ruby.
It was all very confusing for a young man like myself. I couldn't decide if I fancied girls or just wanted to be one.
Ruby told me how she fell out with her daughter a few years ago over how much she drank and how many "uncles" came to visit.
Ruby pulled away, "I like sex Stuart, I like it a lot is that so wrong"
I reassured her that it was perfectly normal. She said that her daughter wasn't coming back so I could have the pick of her wardrobe if I wanted.
She pulled herself together and flung open the wardrobe doors. She told me I could have my pick of any of the clothes. There was a suitcase on the top shelf I could have that too.
She opened one of the drawers and pulled out a pale lilac bra with matching panties and suspender belt.
"This is more your colour try it on", she said.
She started undoing my shirt buttons.
I was quite embarrassed about my chest. At puberty I had developed little puffy breasts and hard pert nipples.
Ruby noticed straight away, "Oh my your chest looks like a pubescent girls".
I couldn't help but blush. It was one of the reasons I didn't really want to come to Torquay because I didn't want to strip off on the beach.
I told her that I always felt girly and how at infant school I preferred to play with the girls in the Wendy House rather than kick a ball around with the boys.
I told her how I would sit with my mum and chat while she put on her make-up and got ready for work. How I so wanted to wear nail varnish but mum said it was not for boys.
The time I wore some clear nail varnish to school and how a girl noticed and teased me all day.
Then I told her about my first proper girlfriend and how she cried when I couldn't stay hard long enough to make love to her.
Ruby listened and said, "Let's make you the best looking girl we can and later this evening we can go out and flirt with men".
"Gosh Ruby", I replied, "That's so scary but so exciting.
Ruby looked at my hair. I was growing it out as I wanted it permed like Kevin Keegan.
"I think we can do something with your hair to make it look more feminine. "I have a friend that cuts mine I'll ask her to come round and style yours."
I wasn't sure and I told Ruby, I didn't want anything permanent. She told me to stop being a wussy.
"Did I want to find out what it was like to be a girl or not".
"Yes", I replied "But I'm nervous and this is all happening so fast".
Ruby told me to go and have a shower and she would pick out an outfit for me. She was pretty sure that I was a size 12 the same as her daughter.
I did as I was told and went for my shower. |
