(Shemale on Male) A boy can't outrun his fate of becoming a sissy..

First story I ever wrote, no idea if it is good or not but I was finally bored enough to post something so feel free to give me any comments, thanks.

It had been about a week now since Nim had arrived at the Lunarfall Garrison in Shadowmoon Valley. It was the biggest choice he had made so far in his life to travel to the alternate Draenor, but it had been a relatively easy choice considering the life he was leaving behind. Nim had been gifted with quite the feminine body, so much so it had begun to get extremely tiring of constantly being mistaken for or picked on for being so lady-like. It was mostly from behind that his gender was mistaken for a female, choosing to wear quite tight fitting leather clothing which only wrapped perfectly around his soft, plump flesh. His hips being described as child-bearing if he was able to do so, the leather trousers he wore squeezing each of his plump ass cheeks to perfectly show off their shape and generous size. His overall height and cute, small facial features simply added to his already feminine look and he was certainly more often than not mistaken for a girl.

It was his main reason to join the Garrison, wanting to basically start again, away from those people he knew already. So far it had been going great, he had been busy each day he had been here. Whether he was off scouting or helping with more simple tasks around the Garrison he enjoyed it all. And though he had noticed several lecherous gazes his way not a single person had actually said anything to him about it, so it was far better than before.

He was nearly finished with todays work, having just unloaded the last of the boxes from the cart he was going to tidy up before heading off to go and sleep. Though before he had a chance to start the cleaning up he was approached by the supervisor of his group. A rather tall, strong looking Night Elf woman. Rather embarrasingly he had to tilt his head upwards to meet her gaze as she spoke to him. "Don't worry about finishing up, i'll have someone else do it. I need one more thing from you, come with me." He hadn't really wanted to stay and clean up anyway so figured whatever other job she had would be better. "Sure urh miss?" She began to walk away, motioning for him to follow. "You can call me Sira."

He followed on, and after just a few seconds of being behind the woman he realised that she had quite the incredible ass. The cloth trousers she wore were slightly strained against each cheek, and he thought for a while about how great it would be to be able to get with someone like that, but he had no real hope for himself. Sira had already peered behind her slightly once or twice to notice the boys staring but decided not to mention, perhaps expecting it. She had lead them up a small little path up into one of the hills in the Garrison, leading up to the top of a small pond which lead down into a few small waterfalls. He was quite surprised to find there was such a nice area hidden away in here, it was so peaceful and calming up here, yet there wasn't anything that seemed like a job up here.

Sira however had lead him up here out of the way for a different reason, she had been watching him work all day, quite lazily lounging around whilst everyone she was supervising worked. She had infact assumed Nim was a girl, the amount of times she had stared at that plump ass of his as he bent over had completely convinced her of that. "Now then, girl. You've made this day real tough for me, so I think it's only fair you help relieve me of all that stress I have built up because of you." He was confused, but thought mostly about the fact he had just been called a girl for the first time since being here, really thinking that wasn't going to happen. "Eh? I don't really understand." It seemed like he couldn't be bothered to argue about his gender right now, having to explain himself was always more embarrasing anyway.

The larger woman stepped right infront of him, pressing a firm hand on his shoulder, swiftly spinning him around before he could even realise what was going on. The boy suddenly tensed up as he felt a strong groping on one of his ass cheeks, figuring that she took him up here for sex, he began to worry mostly about the fact that when she realises he was a boy she would most likely mock and ridicule him before sending him back to the barracks a humiliated mess. "W-wait i'm not a girl, let go." He tried to move forwards, but as he stepped forwards he tripped over her leg that she had slipped infront of him luckily managing to plant his hands into the ground first as he landed on his front with a thud and a groan.

"Owwh.. what the hell was that for.. ?" He went to look over his shoulder and was met with quite the surprise. Sira had removed the cloth trousers she wore and her underwear, and what was hanging lewdly between her legs made the boy completely freeze, his mouth hanging open in shock and his eyes wide stuck on the thick, hard, throbbing piece of meat between her legs. He couldn't believe it, the fact she had a cock and then just how big it was. How did a female have a cock so much bigger than his own, he thought. "Wait.. wait I really am a guy.. stop.." The much larger Elf didn't listen, swiftly lowering herself over him completely covering his body with her own, easily keeping him locked in place against the ground.

"Now then -girl- i've been dying for a piece of this ass all day " She persisted in calling him girl whether he was or not, simply because he looked like one and she thought it would be even more amusing if he did turn out to be a boy. One of her strong hands gripped his trousers and underwear at the hem, roughly tugging them down.. strong tug after strong tug, till they were left at the bottom of his legs, meaning he couldn't really spread them or move them about so much. With his bare naked ass revealed it really was no wonder he was confused for a girl, it was pretty much perfect each cheek was so well rounded and plump, the soft flesh looking like it would just mould in the Elf's grip. She shuffled back a little, suddenly grabbing his hips to raise them a little, wanting to find out for herself what he was.

Poor Nim was met simply with laughter. His cheeks began to burn up in an instant, feeling the heat and colour rush to them as she so obviously was laughing at his cock. "Haha, what is that Oh my, you were right about you being a boy but only just! Look at that thing it's tiny." She continued to laugh, finding this all too amusing as she reached one of her hands to his flaccid cock.. flicking it slightly with the back of her fingers. "What's that three of four inches unfortunate boy- no I think girl was right." She sent a harsh slap against one his ass cheeks, sending him flat against the ground once more. His cock pressed up against his body. She looked down at the red mark appearing on his ass before leaning over him once more, and he felt a large hot presence pushing up between his ass cheeks.

"Please let me go, I won't tell anyone if you just let me go back now.. you can't do this." HIs pleading sounded pathetic, he didn't think it would actually get him anywhere but what more could the boy do. "Owh..? Your going to run back and claim that a girl with a -much- bigger cock than you was about to rape your fat ass? I am sure everyone would love to hear that.. " She had forced her thick, veiny.. throbbing meat between his plump cheeks now, that absolutely massive head of hers that completely dwarfed his tiny virgin asshole pressed against it. "Feel that girl? That's fourteen inches of rock hard, wrist thick cock and it's about to tear you open. Scared?" She grinned, knowing full well that he would be.. she could feel how tensed up his body was, and it made her just more excited to rip him open.

He knew it was coming, and knew there was nothing he could do to stop it he wondered how something so big was going to fit in his ass, and his hands took a rough grip on the ground as he tried to prepare himself. His head lowered as he pleaded with her once more. "Please I never did that before.. that is way too big, you are going to break me.." She smirked, pressing firmly against his hole just not quite enough to gain entry. "Well my little female friend.. that is exactly what I plan to do.. now try not to scream too loud hmm? I am sure you don't want an audience.. " She pressed down against one his shoulders, the other taking a hold of her massive cock as she forced herself inside. It was quite the struggle, but eventually that poor hole of his bust open suddenly around her cock.. slipping just the head and another inch or so inside. A pain filled groan was forced from his lips, a tear already coming down from one of his eyes as he struggle with the pain of his ass being bust open.

"That's enough of a rest time to show you what you can do with a real cock.. " With that the Elf began really going for it, no care in the world for how much pain and discomfort he felt simply aiming to provide herself with as much pleasure as possible. Within the next five thrusts she had already buried herself completely inside, the huge cum filled balls she had smacking lewdly against his ass cheeks each time she hilted inside. She couldn't think of anything better, a little sissy sobbing beneath her as she raped his virgin asshole. "Oh, thats real good your ass might be better than any girls i've fucked before it might not be so good once i've finished though.. "

Nim was really suffering, each time she pushed back inside him a sharp jolt of pain rushed through him.. feeling his inner walls being spread apart so far over and over again. Yet there was another sensation as well that massive cock of hers was roughly grinding over his seemingly sensitive prostate constantly.. each time she moved he felt this weird pleasurable feeling inside him. Enough of a feeling that it had spurred his cock into life growing to nearly six inches. Sira too had seemed to notice the changes in the sounds of his groaning, it was becoming slightly less pain filled and almost like he was enjoying it at times. "Whats that? Are you starting to enjoy having your ass raped? What a nasty little sissy you are does it feel good? Having a cock over twice the sizes of yours breaking you?" She seemed to enjoy the fact he was starting to enjoy it, glad at the chance to corrupt a boy into enjoying such a thing.

"Mhrm how about I give you something you really want? Something a real little sissy like you desires.. ?" Within a few seconds it was clear what she meant, thrusting herself inside one more time.. with a loud slap of her balls against his ass cheeks and a loud, powerful groan coming from her. That thick meat buried inside him began to unload a torrent of cum.. hot, thick.. and filling him up so much quicker than he believed possible. And then.. it what was most likely the most embarrasing moment of his life.. as his hole was completely filled up, an orgasm was forced out of him as well.. his cock spurting his load all over the ground and against his own stomach, pleasurable moans escaping his lips before he completely collapsed all the energy having come out with his orgasm.

She eventually pulled out of him, standing up and admiring her work his ass was a broken mess, left gaping.. you could see the cum filling his ass completely, oozing out of him and dribbling over his own balls lewdly. She squeezed a last few drops of cum out of her softening cock onto his ass cheeks, smirking as she put her clothes back on. "Well, seen as you seemed to like that so much.. you little sissy slut, i'll see you back here tomorrow and don't bother wearing any underwear you won't be needing that." With that she left him there, broken exhausted, humiliated but mostly confused. How had he possibly ended up enjoying that and would he really willingly bring himself back tomorrow?