Where it happened: a bedroom
Langauge: english
Sex: Female
Rating: 3
Category: Straight
During summer when I was fifteen my older brother’s 20 year old friend came over when I was alone. I suppose he had caught me dressing in my sister’s clothes one day, but I wasn’t sure, cause he kept looking at me funny from that day onward. I didn’t know at the time I had attracted him in some way, I suppose I looked pretty.
Well I was in my boy clothes when he knocked and I knew it was him. When I opened the door I looked at him in uncomfortable silence, and then he asked if he could come in…I didn’t know what to say so I said sure, but why was he here when he knew my brother was up in Canada with my parents and sister?
He said he had come to see me, and confessed that he had come through the open door a few months ago looking for my brother and saw me in my bedroom with makeup on and wearing a dress. I was obviously embarrassed and started to plead not to tell my parents, as they would definately think I was a pervert.
He waved his hand and said don’t worry, and sheepishly added that he liked the way I looked, that I looked very pretty. I blushed some more. Now, I wasn’t gay and I was not attracted to boys. I told him so. But when I dressed up I did fantasize what it would be like to be with a boy as a girl…so suddenly that thought came through my mind and made me feel warm in the stomach.
He went on to say that he was not gay either, but there was just something about me that he couldn’t take off his mind. Being bold that he was, he asked me if I wanted to dress for him. I didn’t know what to say so in a surprisingly feminine voice I said “sure” and then went up stairs.
It took me at least a half an hour. Mostly because of nerves and purpose delays…but I stood there in the mirror in a black and white flower summer dress and my best effort yet with make-up. I felt pretty and feminine. I had never been with anyone, boy or girl, so I didn’t know what he was expecting, or what I was expecting…all I knew came from porn videos and had those thoughts in my head.
Anyways I slowly came down stairs with a red face and asked him “This is Samantha…how do I look?”.
“You look great…Samantha…just like I’d thought you’d look…beautiful!” Just what I was hoping to hear.
From that moment on I knew I was going to be a girl. We sat on the couch, kissing…first gently then more passionatly. His tongue in my mouth…then he kissed my cheek, my neck, my ears…I was breathing hard and I grabbed his bulging pants and unzipped them…then he pushed down on my head and I knew what he wanted me to do. I had trouble at first until I relaxed while I licked and sucked on his big penis. I could start to taste his salty cum but kept going until he told me he would come, and then did…in my mouth. I choked a little but managed to show him my open mouth filled with his sperm before I swallowed it. I still had alot on my face. I thought this was what I was supposed to do, as I had seen on the videos…boy he sure liked it and so did I.
Anyways I stayed as Samantha and we just lay on the couch holding each other until he was ready again…this time I wanted him to fuck me. No surprise he had lotion and condoms in his car, as he had come prepared. I told him I didn’t want a condom, and wanted him to cum inside me…I don’t know why. Anyways it was much harder this time and it really, really hurt; but he was gentle and asked me if he wanted to stop…I told him no because it also felt really, really good. He lay on top of me and fucked me for ten minutes with his big hands on my cheeks but wasn’t able to cum even though he stayed hard. So I got on my knees and started sucking him again, and then he came quickly, again in my mouth and face.
Anyways my family was gone for the next four days and I became his girlfriend for those four days, non-stop. Him fucking me in the ass still really hurt, so we only did that a couple more times, managing to cum inside me once. But I did let him fuck me in the mouth alot which I really liked.
Anyways it came to an end and we promised each other to meet in secret. We never did and he didn’t come by anymore after that. I only saw him once again, in the store, the following fall. Our eyes met and he looked away and left. In some way, my girl heart was broken but it did open a whole new world for me…eventually after I turned eighteen I moved out and started dressing as Samantha full time by the time I turned 19, and started to date boys again for the first time since then. When I turned 21 I had my surgury, and married my boyfriend and have been happily married for four years.
If it weren’t for those four wonderful days, would I have ever discovered Samantha?
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