Ever since he was young, Jamie had known deep down that he had always been different to the other boys at school.
Growing up, he would continue to explore his fantasies further and further until one day his sister Sydney caught on and everything wou...
(Jamie's POV) 15 minutes had passed since I'd texted Sam and we had just heard the doorbell ring. "Answer it sissy" demanded Sydney and, yet again, I did exactly as she said and opened the door to let Sam in.
"Oh FUCK" exclaimed Sam as he saw his lifelong friend fully dressed up as a girl for the first time "What th-" he struggled for words to describe me.
Without saying a thing, I pulled him inside, shut the front door and led him to my sisters room where Sydney lay on the bed still in only her underwear and see through silk black robe.
(Narrator POV) "Oh FUCKKKK" exclaimed Sam yet again, with a boner pressed against the front of his joggers which may have been from either Jamie or Sydney at this point. Sydney stood up and locked us inside the room with her, before demanding Sam to strip naked to which he obeyed out of fear, revealing his tiny penis.
"Hello Sammy now you may be wondering what's going on here and why I've brought you here, well you see it turns out that my brother Jamie is a little sissy and I've been thinking that it's about time he made a new girl friend you see." She said cheerfully.
"So I thought who better than little Sammy, the boy who cums in class and will do whatever I say because he thinks I'm pretty" she said before stamping on his foot, causing him to quiver to the floor.
"Jamie will pick out an outfit for you and I'm going to do your makeup, so you better sit still, or else I will be telling people all about how you slept with my brother when he dressed up as a girl for you" she threatened.
"B-but that's never happened" Sam whimpered.
"Well who are people going to believe Sammy? Especially when I show them all the pictures I have of you two together like this right now" Sydney said.
"Ok fine" muttered a defeated Sam, who knew his fate was to be the same as Jamie's.
(Jamie's POV) I made my way over to the closet and picked out a black top, along with a matching black bra and thong, as well as a short pleated skirt for my childhood friend Sam who was sat naked on the end of the bed.
"Man I'm sorry about this but we've got no choice, put these on" I said, to which Sam just nodded and did so.
Once he was fully dressed he made his way over to Sydney so she could do his makeup. I sat where Sam had been on the end of the bed and watched for the next 30 minutes as Sydney feminised his once boyish face. As soon as she had finished the makeup, Sydney rushed to her draw and pulled out a brand new long blonde wig I hadn't yet seen, before putting it in position on Sam's head. The look was complete and I couldn't help but think about how attractive my friend was looking. As he turned and looked in the mirror for the first time I heard a gasp, as he posed for the camera.
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"Oh my gosh I love it" Sam said, clearly struggling to contain his excitement.
"I knew you would" remarked Sydney, as always proud of her work
I was shocked to hear that Sam enjoyed dressing up as a girl just as I did and it really just made the whole day even better than it had been already.
