Dressing in secret to finally venturing out and meeting Simon
Growing up I cross-dressed in secret and only when I knew no one would be home but not being able to dress fully was something I had to accept. I finally got the chance to go the whole way clothes makeup etc while my parents went away for 2 weeks.
My first few attempts at makeup were a disaster then after chatting to a friend she suggested I look search makeup tutorials on the web and after that Chloe’s makeup was getting better.
Finally, I was able to get my own place and was soon stocking it with girly clothes dresses shoes the works and another good tip I got was get the best makeup you can afford which I did.
I was spending most of the time at home dressed as Chloe and the only people who knew my secret was a very close friend Katrina who befriended me online and also dressed and being a few years older at 33 to my tender age of 19. She had years more experience than me and was always happy to give me help and advice with my look and deportment, over time my look was improving.
The next step was for Chloe to venture out dressed this was something that scared me and something I couldn’t do from where I lived, so I would take what I needed and stay with Katrina. The first time I got to her front door where i bottled it eventually I got the courage and took my first tentative steps outside wearing a knee length dress stockings and boots with a jacket full makeup and a dark shoulder length wig. Walking down the street everyone who I passed I was sure they were going to say something but not one negative comment to be honest no one batted an eye lid a few people did take a second look but just carried on. Katrina was giving words of encouragement and I was soon enjoying myself the breeze around my legs as I walked along. I was on cloud 9 when we got back to her house and was warned that there will be times when people see who and what you are and then you will see how shallow some people are.
Over the next few months my confidence grew, and I cannot say it was all plain sailing I did get abuse while outside dressed but on the plus side I did receive some positive comments as well, to the point where we got chatting to a couple of guys who bought the coffee and some innocent flirting. It was after they guys had left Sylvia, admitted she had arranged for them to meet us both something she did to help with my confidence after which it had just had a massive boost. I was soon spending time out dressed sometimes with Katrina or on my own.
Katrina and I had drinks together to celebrate my 20th birthday and as we were leaving the bar, we had to pass a group of youths who started with the abuse “Look cock in a frock” and being called other names it was then I felt myself falling one of them had pushed me over Katrina who was ahead of me was coming back when a hand grabbed me and a voice “Let me help you up” I was still shaken and this guy introduced himself as Simon and was asking if I was ok they youths had gone. Simon kept asking if I was ok and if I needed anything. Katrina was helping me to the door when Simon asked for my mobile number I just looked at him and he said “Its so I can call you tomorrow to see if your ok” so I gave him my number and went home.
Next day Simon rang me I had forgotten I had given him my number and didn’t know who it was until he explained what had happened, we chatted for a while and he asked if I wanted to meet up for a coffee Katrina who could hear the call was mouthing “Yes go for it” so eventually I agreed. After I finished the call Katrina was there saying he fancies you. I met Simon in the shopping centre food court we chatted for ages the time flew by. As I was leaving, he asked if I would be free on Friday night asking why he said he would like to take me out for a meal and how could I refuse so I agreed.
Katrina was over the moon when I told her and started to organise what I should wear. Getting ready for my first date as Chloe butterflies in my stomach There was no way I was going to miss this I liked Simon. I wore a halter dress and strappy heels, full makeup and the usual shoulder length wig and to finish a short jacket over my shoulders.
I had arranged to meet Simon outside at the restaraunt as I didn’t want him to know where I lived. He greeted me with a kiss to the cheek and complimented on my appearance. We enjoyed a 3 course meal and wine and plenty of chatting after which he asked if I wanted to go to a bar for a drink or would I like the drink at his place, I said his place would be fine.
I was stood looking at one of the painting in his apartment when I felt his hands on my waist and kisses on my neck pulling my hips into him I felt his hardness pushing against me I was rubbing by ass against it and it felt good. I turned round facing Simon my hand on his crotch massaging his cock through his trousers, then undoing his trousers letting the fall to the floor my hand was inside is pants his cock was average size it was hard in my hand and I was slowly wanking him as he was pulling off his pants then eventually getting them down he kicked them away with his trousers and now I could see his cock erect in my hand.
I went down and holding his cock let my tongue brush over the head I could taste the pre cum and took it into my mouth sucking it hard while massaging the shaft and balls then licking down his shaft and taking his balls one at a time into my mouth before taking the cock back into my mouth sucking and wanking him it wasn’t long until he unloaded at thick warm cum load into my mouth. I swallowed most of it, it tasted good better than some I have tasted.
We moved to the bed where I was face down he lubed my ass and then I felt him enter me his cock slid straight in it felt so good it had been quite some time since I had felt a cock inside me and I was loving this sensation again, his deep hard thrusts getting faster slowing down teasing my ass he eventually emptied another load inside me in all I sucked and he fucked quite a few times that night and fell asleep in his arms.
When I woke in the morning his arm was round me I could feel his limp cock against my ass and my moving woke him up I started to play with his cock and soon had him hard so I could ride him and feel him deep inside me sliding up and down on him till I felt the cum filling me up I sat there with his cock going limp inside me which eventually came out with a trail of cum onto his stomach.
After breakfast and yet another fuck bent over the kitchen table I got cleaned up dressed and let him take me home now I wasn’t worried about him knowing where I lived he was welcome to come round anytime.
I had to fill Katrina in on all the details which she loved listening to it all.