The Break

I am a cosplayer. I've always enjoyed dressing up in costume as characters from tv, movies, and video games. As a man, I generally stuck to doing male characters. That said though, I've really wanted to cosplay as my favorite character from one of my long time addictions, League of Legends, for a long time now. The problem with that though is simple, my favorite character is a woman, Caitlyn. So, I never could pull that off believably, until now. You see, I recently told all of this to one of my close friends who is also a cosplayer since I was hoping she'd make a cosplay for Caitlyn and I could kind of live vicariously through her. Well, she was already half way through a different costume build and instead offered to help with makeup and making my body look the part so that I could actually cosplay as Caitlyn. I was hesitant at first but I trusted her and my desire to make the costume work lead me to accepting her help. So, I figured out what skin I wanted to emulate and settled on her pool party skin with the thought that I may as well go all out. I gathered the closest things I could find from stores around my house to make the costume and with a bit of help from Belle... drum role please!

Ta-Da!!! If I didn't know better I'd think that was actually a picture of a woman. Well, anyways, thank you all for reading and for all the love I've already gotten for the costume!

And with that posted to Twitter and Reddit I feel like it's time to enjoy our handiwork. With the costume still on and looking great I made my way to the pool to get some more pictures and then relax. That's when a man came up to me and asked if I'd like him to take some full body shots. Not really thinking anything of it I accepted handing him my camera. When he heard my voice, he seemed surprised, but he didn't say anything... at the time. After taking a few pictures we had this exchange.

"I could never understand how a man could be such a sissy."

"Annnnd, what is that supposed to mean?"

"Well, you're dressed as a woman, you're wearing makeup, and you have your penis tucked away."

"Ok... and? Just because I enjoy cosplaying and I happen to be cosplaying as a woman you think I'm a sissy? I'm not, I'm just comfortable with myself enough to dress however I like, in this case in a female costume."

"I'll pay you a thousand dollars, right here, right now, if you can prove that you're not just a little sissy in denial."

"I'll take that bet, how can I prove it?"

"Leave that to me."

With that he pulled out a stone from his pocket which almost seemed to glow a sickly green color and everything changed. We were suddenly in a hotel room without clothes and somehow, I had turned into a woman... well, almost a woman, I still had my penis. Before I could question anything though my body began to move on its own. I tried my best to resist my body's moves but nothing I did changed the fact that my body was approaching and then mounting the man. As I started to feel the head of his cock being positioned for insertion my anxiety grew exponentially, no part of me wanted this, I was straight, I wanted nothing to do with what my body was seemingly about to do. Despite my best efforts I couldn't seem to do anything in protest. Luckily though, it seemed like I had suddenly regained control, well, partial control, I could not decide to move but I wasn't getting any closer to losing my anal virginity. That's when he finally spoke.

"So, here's what's going to happen, you're going to ride my cock, whoever cums first loses. I you win, I'll give you your money and that'll be it, however, if I win, I get to do whatever I want with you."

As soon as he finished his statement all of my perceived control vanished, with no hesitation my body swiftly impaled itself on the man's cock and before almost pulling back off of his shaft only to repeat the process. I hated it. I hated what was happening. I didn't like it. That's what I told myself, but my body betrayed me, after only a few short minutes my penis was shooting off warm jets of cum while I experienced the most intense orgasm of my life.

"What do you know? Looks like you are a little sissy slut. Only a sissy would cum from being fucked in the ass."

I was still in complete shock and had so many questions, luckily, I could now ask them.

"What the fuck? Why do I have tits? Why do I sound like a woman? Why couldn't I control my body."

"Hush now my little sissy. All-"

"Don't call me a sissy, asshole! You did this, I don't know how but I know you did. You probably rigged it from the start, You probably made me cum with whatever you did to give me tits."

"I'm sorry sissy, but you can't talk to me like that anymore... as I'm sure you will soon discover."

As I went to hurl more insults and demands none of my words came out. Rather, I said "I'm sorry master, I promise I'll be a good girl from now on."

"That's better. now, to answer your questions. I used this." in his hand rested the same odd stone from before. "Long story short, this is magic, it allows me to do whatever I want, like this." As if on cue his cock grew longer and thicker.

"Now, in regards to our little bet, though, it was indeed a rigged game from the start, I did not cheat. Your inner sissy simply showed herself, as I knew she would. Now, for my winnings I'd love it if you finished what you started and suck me off until I feel satisfied."

Seven, I have been spectating some weird female version of my body for seven loads of this monster's cum. My body reacted to every load as if it was a gift from the gods showing it off before swallowing it and opening my mouth to both show what a good girl I was being and get ready for the next round. I don't know what I hate most about all of this, could it be the presence of his cock in my mouth? All the cum I've swallowed? What a slut I am being despite my complete lack of control? Or, that I'm starting to like it. With ever slimy load that slithers down my throat I seem to be experiencing another orgasm. I say seem because I haven't produced cum of my own since the fourth load I swallowed. I can also tell that with each ounce of this man's seed that's forced down my throat my mind and body are further feminizing. My penis is more of a clit now and I can even feel a slit forming just underneath it.

"You are doing so well sissy, you're already getting better at pleasing a man. I'm so proud of you taking back control and really going for it."

"What do you mean master? The stone is still in control."

"No sissy, It hasn't been in control since my second orgasm. Everything after that was all you!"

"Stop lying to me master."

"I'm not lying, in fact, how about this. I'm going to stand here with my cock inches from your slutty little mouth, and you get to decide what happens. You can either start up, what was it, round eight? or, you can walk your girlish body to the door and leave. If you leave now I'll reset everything, you'll be a 'man' again, and hell, i'll even fill your bank account with enough money to to buy four mansions every day for the rest of your life. Sound like a deal?"

I want to say I stood up and left the instant he quit talking, or even that I wasn't in control and couldn't. Neither of those options were true though. I sat there, staring at his cock for ten minutes. Ten full minutes. Every time the thought of leaving crossed my mind another though crept in behind. 'Have just one last taste.' 'It wasn't that bad.' 'You were starting to enjoy it.' I had two competing voices in my head and for ten minutes neither was gaining ground. Then, something broke.

In an instant everything became so clear. I never was a man, I was always a little sissy girl but I was too scared to show it. He brought the real me out, I was free, and most importantly, I had a nice big cock in front of me to play with. I didn't start sucking him off yet though, no, that wouldn't be good enough. I was mesmerized my the size, smell, texture, everything. Everything about it was amazing to me. I could remember every detail about it from when it was inside of me and nothing excited me more than giving in to my desires.

With no more inhibitions I gave his beautiful cock a few strokes before eagerly beginning my new life. This was the blowjob that made everything right. All those years I spent lying to myself about being a man were all worth it for this moment. I was so happy to finally be me and after I made him cum three more times my penis was completely gone, replaced by a tight little pussy that craved to be filled as much as my mouth did. After my transformation was complete the man told me to leave claiming he had no need for a needy cock slut. I did as I was told, mostly because he used to stone to make me, and left. I was sad I couldn't keep playing with his cock forever, but, soon enough, I found that my sadness was unwarranted. As it turns out, everyone only ever knew the female me apparently, that was a relief since I wouldn't have to explain my transformation to everyone and risk them thinking I'm crazy. And, as a great side product I was, let's say, much closer to a couple of my male friends than before.

In the end, my love of cosplaying fell by the wayside to make room for my love for all things cock. Who knows, maybe I'll be able to mix them some day, for now though, I've got a lot of catching up to do on behalf of all those wasted years as a man.

(Wow, another story already, I'm on a roll! Jokes aside, I enjoyed writing this and I hope you have enjoyed reading it. As a bit of an aside, I didn't cheat with the first picture, that really is a guy, I know, hard to believe but it's true. He's a professional League player who, with the help of his girlfriend, 'crossplays.' I don't know, I think it's kinda cool. Either way, I once again hope you enjoyed the story and I hope you have a good day. ^_^)