He was not expecting to lose

James knew what he had to-do but he didn’t like it, he didn’t like the clothes, he didn’t like that it aroused him and mainly he didn’t like the fact he made that stupid bet. It was supposed to be a joke, his team could win easily and should have won, but still, they had lost. After the victory he would have let it slide just like he would expect his best friend to do in case James (or in this case Jamie) lost, but he didn’t, even though James begged him, what a prick. Prick r not, no excuses, a man stands by his word, it has to be done-James thought to himself.

And that’s how he ended up in his sister’s skirt and tank top with matching bra and panties underneath, he was told to shave as well but he didn’t needed to, the fact that he had long, soft, feminine hair and a girly face didn’t help much too.

After he put some make up on, he was also told to do so, he went to Rick’s house, Rick being his supposed best friend, as soon as he knocked on the door Rick told him to follow and they went to his room.”Alright Jamie, you look like a hottie, let me go get the lube and I’ll deal with ya in a few seconds” Rick said and then disappeared into the bathroom, leaving James waiting, in a mix of fear, excitement, arousal and mainly shame. It took a minute or two but Rick eventually found the lube bottle. Reluctantly James who was facing Rick turned around, his back facing his friend now and started to take off his panties, but Rick stopped him, “it’s not going to be that easy, first you gotta suck me” he said with a big grin. Jamie,(yes Jamie and not James, there was no point in trying to be James anymore) dropped to his knees, unzipped his friends pants and pulled down his boxers to find the biggest monster cock he’d ever seen, even though he’d never seen any besides his own, but still that thing was huge, and was not even fully erect yet.

He commited to it, his mouth wrapped around Ricks cock, he could see him laughing between gasps of pure emotion. While Rick seemed to be having a blast, Jamie didn’t like it at all, he didn’t like the taste of precum, he didn’t like the texture of his friend’s cock and he didn’t like that his lips were getting sore due to his efforts to wrap his mouth around Rick’s impressive instrument. He was not liking it at all, that is until Rick came, a huge load of white salty perfect juice was shot into his mouth as fast as a bullet, but that was only the first one, right after that many more came, one after, another big huge loads of that magic liquid entered Jamie’s mouth. He thought about spitting it out but decided it would be better to swallow just because he didn’t want to make a mess, the taste was a surprise, he didn’t like it, he loved it! After swallowing all of it, he got up, feeling a lot better and less ashamed of himself, somehow.”You still have some in the corner of your mouth, Jamie” Rick said mocking him, Jamie just licked his lips cleaning them of every last bit of cum.

Knowing what came next Jamie turned around, lifted his skirt a bit, just to show Rick that he knew he had curves and he liked it and started taking of his panties, very slowly almost as if he was teasing his friend, as soon as he got them of, he kissed them, marking them with a red lipstick kiss print and gave them to Rick, after that, he got his hands on the wall spread his legs and stood there waiting for Rick.

And that’s how James became Jamie.

Note: i forgot to ask but this is my first story and i would love to know what you think about it.
Hugs, Angie