My story started when I used to try on my sisters panties and wear them around the house when everyone was gone. This led to cross dressing when I left home at age seventeen. I did finish school but took care of a friends apartment and dog when he was gone during the week. I dressed as a girl when their most of the time since it was just me. No one visited so I was pretty safe not being found out.
One hot summer day I was only in my panties setting watching TV. I did not here anyone enter the house, suddenly I realized someone standing to one side of the room looking at me. I pulled a pillow over my lap as I turned to see who it was. Thinking it was my friend Kevin who came home early and caught me in my panties. To my surprise it was a friend of Kevin’s that I met once. Standing taller than me and at least ten years my senior, well built with dark tan skin, he looked every bit a man to me.
Shyly I clutched the pillow and looked down as he broke the silence and said, I hope I did not startle you. I could not help but see you are wearing some lovely panties. He asked if he could get a better look at them? As if in a trans I looked at him as he walked over to me and held out his hand for me to grab. Not saying a word. Scared to the point of shaking he put his hands on my shoulder and told me to relax. He then had me turn around slowly to look me over. He then grabbed my ass and squeezed it gently saying “Nice”.
He then asked if Kevin was around and I finally squeaked out “no”. He is gone all week I said. He told me to tell him that Bob stopped by. He complemented me on my panties again then left. I was still shaking from the encounter, at the same time felt thrilled that I had been seen in panties. I thought about it the rest of the day and became excited about it. I jacked off the rest of the week reliving the incident over and over in my mind.
Two weeks latter Bob called and said he would be over in twenty minutes or so. I was in my shirt and shorts so I quickly picked up the place making sure my girly clothing where put away. Bob was knocking at the door by that time. He came in and was looking more masculine than I remembered him. He asked how I was doing and if I had on my panties under my shorts. I told him I did not have them on and asked what he wanted. He told me that he would like to have seen me in my girly clothing. He asked if I would go put some on for him while he waited. Getting aroused at the thought of being seen cross dressed gave me an erection. Bob assured me it was alright and that my secret would be safe with him.
Knowing I still was not comfortable with the idea, he told me that he would pick me up that coming Saturday and to have my lingerie on under my clothes. I did as instructed and waited nervously for him to arrive that Saturday. He showed up on time and I got in the car and he took me to his place. Once there he told me to take my cloths of so he could see my lingerie. I did as I was told knowing that this was going to end in sex. He was impressed at what I was wearing, camisole top, garter belt and stockings, and white lacy panties. My erection was obvious as it tented my panties. Bob came over a caressed my cock and balls through the panties and told me to drop to my knees. Knowing what was coming next made me even harder as he took his cock out. Seeing such a handsome cock made me feel as if I was in a trance. I opened my mouth and Bob stuck his big cock in, I sucked it until he filled my mouth. Gaging he held my head until I swallowed it all. I new that my life had changed forever.
Bob and I kept our friendship to our selves not telling anyone. He took my virginity a week later when I visited. I would go over to his place and spend the night some times during the week. He started buying me lingerie and outfits for me to wear when I was around him. This continued all that year, one day he took me to a female friend of his who showed me how to put on makeup. Over time I made many visits to her house to perfect my makeup. Once I learned the task which was months and months of practice, Bob took me out in public for the first time. I felt nervous but excited at the same time. He told me I looked lovely and we went to a night club in the city. Over time I became more confident in my dressing and looks. Bob was all man and treated me as the girl I whished I could be.
I moved in with Bob a year and half later and became his girlfriend dressing as a girl 24/7. Everyone who saw me thought I was a girl because I looked so feminine. We lived together for several years then one day Bob shocked me by asking if I would marry him. I accepted and became his wife six months later, lucky enough to live in a state where it was legal. That was three years ago and Bob has asked if I wanted breast implants about a week ago. This is something I have dreamed about since I started cross dressing. We talked about it and I told him that I would like to try and grow my own breasts naturally first. He has scheduled the first of my doctor appointments for next week. I can hardly wait, my cock gets hard thinking about it. Bob is happy that I am so thrilled at the idea.
SM (Sissy Maker)