Early day of a crossdressing sissy
When I was much, much younger I had a Saturday job in a small book shop. I was just trying to figure out who I was, I liked girls but I also liked to dress up in my sisters clothes, I did this on the rare occasions when the house was empty,
So back to my job in the book shop, the owner was Ian a good looking bloke in his forties. After a few weeks of working there we really got on well and I started to wonder what it would be like to be with a man while I was Grace, this is the name I gave my self when crossdressed. I donāt no why as he was happily married and nothing he said or did was in any way flirty to me.
When I had a chance I would dress up and imagine taking a his cock in my mouth, I came so hard and then felt so empty as it was just in my head. Weeks of this went by and the thought was consuming me. Then I came up with what I thought was a brilliant plan.
I told Ian that the following Saturday that is going to go to a fancy dress party after work. So the next Saturday came round and my heart was in my mouth and my stomach was doing cartwheels, I arrived at work with a bag of clothes and some makeup stolen from my sister.
At round Two in the afternoon when the shop gets quite quiet I asked Ian if would be ok to try on my fancy dress outfit to see if was ok, he agreed and of I went in to the store room.
I felt physically sick as I stripped and started putting on my sisters panties, she is a couple year younger than me so all her clothes ware quite tight on me, I had taken her school uniform that she wore short, so on me it was very short and tight, but the effect I felt was vey sexy, Then I started putting on some of the makeup, I was not skilled at this as I had never done it before but I had watch both my mother and sister do theirs and I was pleased with the look,
I had been in the store room for about twenty five minutes and called to see if all was ok? His voice made my jump out of my skin and when I called back it seemed to come out as a squeak, I looked at myself in the mirror and took some deep breathās, l told my self that this was the plan and it would be ok, I would tell Ian that all the boys would be going as school girls and would ask his opinion on the outfit, I he just laughed I could brush it of as just silly party.
So the time had come , I called Ian to come to the store room and give me verdict, my head was spinning.
He came in looked at me, his mouth opened but it took a few seconds for him to speak, Fucking hell you gorgeous! He said
i canāt believe itās you. Fuck if you were a real girl I be all over you.
But I look like one! I said, it went very quiet, I could feel the blood pumping in my head, I looked up at him with a very shy smile,
He looked at me and said, oh I donāt know about this James, Call me Grace. I said in a very small voice.
More to follow.
So back to my job in the book shop, the owner was Ian a good looking bloke in his forties. After a few weeks of working there we really got on well and I started to wonder what it would be like to be with a man while I was Grace, this is the name I gave my self when crossdressed. I donāt no why as he was happily married and nothing he said or did was in any way flirty to me.
When I had a chance I would dress up and imagine taking a his cock in my mouth, I came so hard and then felt so empty as it was just in my head. Weeks of this went by and the thought was consuming me. Then I came up with what I thought was a brilliant plan.
I told Ian that the following Saturday that is going to go to a fancy dress party after work. So the next Saturday came round and my heart was in my mouth and my stomach was doing cartwheels, I arrived at work with a bag of clothes and some makeup stolen from my sister.
At round Two in the afternoon when the shop gets quite quiet I asked Ian if would be ok to try on my fancy dress outfit to see if was ok, he agreed and of I went in to the store room.
I felt physically sick as I stripped and started putting on my sisters panties, she is a couple year younger than me so all her clothes ware quite tight on me, I had taken her school uniform that she wore short, so on me it was very short and tight, but the effect I felt was vey sexy, Then I started putting on some of the makeup, I was not skilled at this as I had never done it before but I had watch both my mother and sister do theirs and I was pleased with the look,
I had been in the store room for about twenty five minutes and called to see if all was ok? His voice made my jump out of my skin and when I called back it seemed to come out as a squeak, I looked at myself in the mirror and took some deep breathās, l told my self that this was the plan and it would be ok, I would tell Ian that all the boys would be going as school girls and would ask his opinion on the outfit, I he just laughed I could brush it of as just silly party.
So the time had come , I called Ian to come to the store room and give me verdict, my head was spinning.
He came in looked at me, his mouth opened but it took a few seconds for him to speak, Fucking hell you gorgeous! He said
i canāt believe itās you. Fuck if you were a real girl I be all over you.
But I look like one! I said, it went very quiet, I could feel the blood pumping in my head, I looked up at him with a very shy smile,
He looked at me and said, oh I donāt know about this James, Call me Grace. I said in a very small voice.
More to follow.
8 months ago
