….. a few weeks after my last visit to Carol for a makeover I emailed her and enquired about availability for a makeover and escorted trip out in the evening. I had a knot in my stomach with excitement in anticipation. I arranged an early finish at work. Luckily my place of work had a private shower area and I took the opportunity to shower and fully shave my face and body before I left work to attend the appointment. As I often do I wore a nice bra and panty set with tights under my regular clothes to make me feel girly and get me in the mood. Not that I needed any encouragement. Carols place was a little out of town but I had my car with some overnight things and some personal girlie things of my own that I brought along. I liked to use my own B cup breast forms as they were a nice fit for my slender frame and some extra panties and stockings I liked.
On arriving at Carols I was a nervous wreck. I had dressed before but the thought of going out in public was off the scale in terms of excitement and terror. Carol was her usual friendly self and made me feel at home. She recommended we head into town to a nice quiet bar for a couple of drinks before moving onto a well know LBGT nite spot. Not eating any time we got to talking about what we would wear. I eventually settled on a lovely dark green halter neck top dress with sparkles and and some semi opaque tights and some heeled ankle boots. The excellent make up work and a mid length brunette wig made me the most passable I have ever seen myself. Carol
Made me transfer all my money, phone and cards into a small purse and handbag and helped me into a gorgeous mock fur jacket.
Before I knew it we were in the car and into the centre of town. My head was spinning from
Start to finish. Would I be spotted as a guy in drag? Would anyone say something to me? No nothing like that. Quite the opposite. Doorman smiled and called us ladies. Girls smiled and said hello. I had the most wonderful night. I ordered drinks at the bar. I danced on the dance floor. I even visited that most sacred of places , the ladies room. At one point I managed to loose Carol. I didn’t panic. I had had a few wines at this point and just indulged in some people watching until we found each other again. It was such a buzz in how I looked and how I felt. We returned home to Carols place and stayed up for a while before I retired to bed in a little satin nightie carol had thoughtfully laid out for me. Next morning I showered and went straight to work.
Since then I have been on several more escorted trips out ( I may write about them In more detail in separate blogs)
In the meantime
Though I did discover Tv chix website which led me to my first encounters as a sissy with men.
After years of dressing I knew a sissy yearning inside me was growing and it wasn’t enough to dress up anymore. I knew there was more to my journey than that. I knew forced feminisation humiliation and serving others was what would make me a complete sissy.
From my profile page on chix I reached out to others and got chatting to a dom guy who also
Liked to dress too. We chatted and exchanged messages and fantasies for months until one day I had opportunity to visit his home town with my work. We agreed to meet.
It was another nerve wracking affair! We agreed to
Meet in the hotel bar where I was staying. He would be in guy mode and I was to dress , as per his wishes, in a little black cocktail dress sheer stockings and heels. Full Make up and wig. My make up skills are not the best but I’ve had quite a bit of practice at this point and did my best work before I plucked up courage to leave my room at 9pm and head to the lift and down to hotel lobby and bar. He was waiting for me like a gentleman and we chatted for a couple of hours. It felt lovely to be treated like a lady. We eventually agreed to go back to my room as I linked his arm and headed to the lift. I poured a glass of wine for us both in the room and he asked me to take off my dress. He asked if I’d like to be tied up which I nervously agreed to. I was face down on the bed and blindfolded when I felt my panties being pulled to one side. Next thing I felt was some lube being squeezed inside my boi hole. Almost instantly I felt something warm and bulbous enter my hole. Forcing itself past the tightness and deep inside me. I had no time to react until it my sissy hole had greedily swallowed up his cock. He then proceeded to thrust repeatedly for another 10 to 15 mins until I felt his cock go super rigid and start throbbing with his cum. He had a condom on which I was thankful for. He lay on me for another minute and then silently untied my hands. He asked me to stay still until he had left the room. I heard him leave and untied my other bonds and blindfold. He had left is cum filled condom on my
Pillow. I was no longer a virgin. I was a real used sissy and I loved it.
I’ll get round to writing about other experiences in next blogs and hopefully about my experiences at the hands of Mistress Nicole
When it is safe to start my training.