After experimenting with crossdressing, I had the urge to go further.
It was a Friday evening, the house was empty and I grabbed the opportunity.
I had a hot shower washing my body with some feminine shower gel, lucky I didn’t have too much hair over my body but made the most and shaved what little I had. Getting out of the shower and wrapped in a robe, I sat at the dressing table, dried and styled my hair. I applied my makeup and proceeded to paint my nails. It was then I put on the matching underwear, a black lace bra, silk panties with matching garter and stockings. Then came the silk blue blouse and black pencil skirt that I loved so much. This was finished off by 4-inch sandals.
I stood back, looked in the mirror and felt so womanly. I walked through the house feeling very sexy, growing in confidence. I opened the door to the side of the house and stepped out.
What a rush as I walked along the path and around the side of the house, loving the sound of my heels clicking on the path.
It was then my world changed forever. Jon, a very close friend of the family, arrived unannounced.
Jon saw me and called out, he had clearly not recognised me. I ran past him and back into the house, heart in mouth, tears building, knowing that I had been caught. Jon followed as I locked myself in the bedroom, fearful of what he would say.
Jon called from behind the locked door; he had worked out who I was.
“Please open the door, stop crying,” he said. I pressed against the door as he tried the lock.
“No, please, please go away,” I sobbed.
“Open the door, it’s okay, it’s our secret,” he said. I believed Jon. He was always kind, honest and very generous to our family.
“Again, please let me in. We need to talk,” he said. As I opened the door, Jon stepped in to see my tear-stained face with mascara running down my cheek. Jon opened his arms and I instinctively fell into them sobbing, saying how sorry I was, begging him to not tell.
“It’s okay,” he whispered, “it’s our secret”.
He held me, then pushed me back looking into my eyes and said, “Stop crying, you’re spoiling that beautiful face.”
He told me to sit on the bed where he joined me, holding my hand, and reassured me that it would be our secret.
He asked if I liked dressing and said I looked beautiful.
“Please, please don’t tell, will you?” I repeated. Jon said I should be who I needed to be and if I wanted, he could help me. He then suggested I get out of the clothes and makeup and go back to my male clothes before anyone else came home. I did as Jon said. He helped himself to a coffee and waited for me in the lounge.
Still very afraid of what Jon would say, I joined him in the lounge.
He told me he thought I looked stunning and asked if I thought I was gay. It hadn’t occurred to me. At that point, I simply wanted to be me and look as feminine as possible. We talked and he suggested I stay with him during the long holiday, something I had done previously so it would not seem unusual to the family. It was then that Jon asked if I wanted to be dressed as a girl or young man for my stay. I looked at him and he said there was no pressure and I could let him know when I felt comfortable.
A week passed and Jon arrived to pick me up. We drove to his apartment, making small talk as we drove. We pulled into his garage and got out of the car. Going up in the lift, Jon said he had bought some things I could wear only if I felt the need. Excited, I went into the bedroom and found clothes hanging in the wardrobe very similar to those he’d caught me wearing the week before. The urge was too strong and I dressed, putting on the clothes with full makeup.
Walking into the lounge, Jon was sitting on the sofa. He looked around and said, “Wow! You look beautiful, what’s your name?”
It was at that point I realised I never had a feminine name.
“Samantha… Sam,” I stuttered.
“Hi Sam, may I say you look gorgeous? Come sit here. I’d like to get to know you.”
And that’s when it got interesting.
We sat and chatted and as Jon kept paying me compliments, I realised his hand was holding mine. He offered to take me shopping to buy a special wardrobe of clothes and shoes to be kept when I wanted to be Sam. The excitement made me do something I would never have considered before. I kissed Jon and said, “Thank you”, for his kindness and understanding.
Jon tenderly kissed me back. The kisses became more intense as Jon pulled me closer. My hands moved to wrap around his neck as we lay back on the sofa, Jon taking control, he kissed my neck. My mind was racing, breathing more heavily as he explored my body with his hands. I could feel his cock growing, getting harder. I wanted it now more than ever. Jon unbuttoned my blouse and pulled the bra away to find my nipples, where he proceeded to suck and gently nibbled on them.
Fuck, I was horny. I fumbled at his belt and he took the hint but not before asking if I was sure. I was sure. I’d never been so sure in all my life. I wanted this. I wanted Jon and wanted to feel his growing cock. As Jon stood to take off his jeans, I could see his cock pressing against his trunks. I bit my lip, looking at his cock straining through the material. I looked up at Jon as my hand moved up to unleash his glorious cock. It sprang out, and I licked my lips.
