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Life changing day

"How we got to knowing each other"

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First of all, i am Afrikaans speaking but writing my story in English.

Cross dress surprise.

I love to cross dress when i am in the mood, which is easy and often as i stay all alone in a 3-bedroom house all private on a farm.

This is the story of a day i would not change for anything.

I am all excited and pleased with myself waiting for a fellow cross dressing friend all dressed up and ready for a nice day. Waitng patently for an hour to pass for a nice day having a few drinks and a braai (bbq) with my cross dressing friend who's always up to fun and surprises. Suddenly, my doorbell rang, and i am all happy he came over sooner than later. i did not even bother to check and just ripped the door open to welcome him.

Well, to my surprice, it was not him!!!! But a beautiful young lady i knew from the shop nearby whom i had over to my place a few weeks earlier for drinks and just a visit to know each other better, nothing really sparked between us. But I'm always happy to see and have a little chat. I told her the day before that she is welcome anytime if she feels like it. Damn i expected a call, not just show up.......

I don't know who was more in shock, but it turned out it was me indeed. She had the first words after she looked my over and me just standing there, not knowing where to look or should run to. "My my my well don't you just stand there and not let me in you sexy gurl" is all i heard. Her eyes were all sparkling, and she smiled from heaven.

I just showed her in without words and closed the door to shy to turn around. Her hand suddenly on my shoulder and in a sexy voice telling me not to be embarrassed and just be who i am. I turned around and looked at her then only saw she was all sexy dressed in a mini and tight top make-up on and looking hot as hell. All i could get out was wel you sure look a lot more sexy than i want to look. I was expecting someone else and not her. And just at that moment, my phone rang on the table. As i walked in my new sexy heels to answer, she said, " i see someone needs training around here." Well, it turned out it was my friend to cancel due to some work crissis he had to go sort out.

I put the phone down and turned around, asking her, "Training?". She said well it would be her pleasure, and she would not mind a bit to help me." She pointed out a few mistakes she saw in my clothing and pantyhose. And how i walked, but the big thing is make-up that should be done all over with her help. I felt very much at piece with her tone of voice, as if saying i am here for you dont stress.

Well, i gladly thanked her, and before i could ask her, she said it would stay a secret between us as long as i want. She gave me a really affectioned hug and a soft kiss on my lips. Well now how about a drink and then we can go and re do your sexy face she said. And as we had a drink, it turned out to be another three chating talking openly about my double life as a bi-sexual guy. And more spesificaly about "Jenny" siting infront of her.

Then to the bedroom and straight to the on suite bathroom and as i washed my face off, she said she could not find my make-up. I realised suddenly that it was put back in the draw with all my sex toys. I told her i will get it and she told me in a stern voice "no tell me i will see what you have and need" well she opened the draw i told her and as i came into the room all my toy's lingerie and make-up was packed out on the bed with her sitting there.

She told me that i really have a nice collection of everything and she wich she had some of the same. And then ordered me to sit in front of the dresing table. She really went out of her way, showing and explaining how and why with every step of make-up. Damn i saw myself transforming into some really hot chick with beautiful lips. Then, as i stood up, she made me stand and undressed me to just my bra,panty,carter, and stockings. I could not help myself and had an erection that i could feel pounding like a heartbeat in my panty. She just gave me a sexy smile softly rubing my sissy clit and said before your dress come back on that will need to get soft and tuged away. She then re adjusted my bra and breast forms and turned me to the mirror explaining the adjustment. Then pointed the pin stripe of my stockings not being neat and straight at the back of my leg and corrected it for me. Then i had to walk up and down the room for her and she realy helped me with patiance in my new stiletto hi heels. As she started to be pleased she made me walk all the way down the hall through the living room to the front door and back correcting me as needed. On the 3rd time back she gave me a sexy long kiss and praised me learning so quick and not complaining about critic. As i looked at her with pride in myself she said i must go pour as a drink and wait for her at my bar. Well not long then she called me back to the room with the drinks. As i walked in i noticed she striped down to just her lingerie and had put the stap-on from my toy collection on. Breathlees i just froze up nothing to say and my erection full on throbing again. As she looked me up and down she said "well Jenny my dear you sure look pretty sexy now". She stepped towards me and took her drink and my hand and led me back to the bar area. She asked me why i look so shocked about the strap on cauce it is mine and i must want someone to wear it else i would not have it. That just made me blush and nod my head in aproval. We had another drink and then she got off her bar stool and droped to her knees infront of me and slipped my throbing 4 1/2 inch sissy cock free from my panty. Playing with it then started sucking me like i never felt before in just a minute i blew my load with her not waisting a drop not leaving a trace of cum as she swallowed all. I pulled her to her feet and kissed her pasionatly long and loveingly. Then i said i almost figured you were going to peg me till i cum tonight but you realy surprised me good. I told her that i love eating pussy to get a lady to orgasm. And then attempted to remove the strap on. Boy was i wrong she shoved me away and slaped me hard on the cheek. "How dare you remove my un used cock you little slut" she screemed at me. " go to your room now" i just turned and walked best i could like she showed me with her behind me. As i entered the room she slaped my ass realy hard that i jumped up and yeled sorry for me being so stupid. She put her arms round me holding me tight and said i will forgive you this time just bend over and let me cool that slap off. As i did as told she went to the bathroom and i just stood there bend over the bed on my feet arms on the bed. She came back behind me and put a cold wet cloth on my ass cheek and held it there whispering in my ear "you feeling better now sissy gurl". I thanked her and wanted to turn around butt she said stay just like you are. She took her handbag and pulled out a tube off lubricant and said now you will be a real little girl for me. Pulled my panty off and ordered me to lay on my back on the bed. She then put lube all over her strap on cock and told me to open up my legs wide and high. She lubed my sissy pussy up good using one and then two fingers at a time. Then kissed me passionatly again before slowly sliding in me bit by bit realy carefully and with my cumfort as her priority. She saw when i got used and cumfy then slowly began moving back till almost out then back in and every time a bit faster till i started moving aswell to pick up the pace. She then leaned forward taking my face in her hands kissing me and thust harder and faster every time. She fucked me for i think about 15 minutes

Damn i could see the pleasure it gave her and how it aroused her till she had an orgasm quivering in my arms and inside me with her cock. As she got up we noticed i also had an orgasm as your bellys were full of my cum. Damn i never even felt myself blowing cum as she fucked me so good and pasionatly.

And now she has become my best girlfrend and mentor as to cross dresing. She even got me wigs and took me out to the local pubs few times as her girlfrend without anybody reganising me.

One off the days i will be ready to dress and go on my own.

And just maybe one day i will be able to see her totaly naked to see how all off her looks like and even get to fuck her. I have never seen her in less than a panty and bra. But for now she fucks me on every date we have. And i realy don't want sex with another woman. I only have her and my cross dresing frend as sexual pertners. And boy he can fuck realy good and lets me fuck him good aswell. But that is a story for another day.

Xxx

Jenny.

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Written by Jenny

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