( Shemale On Male ) A Boy Ca N'T Outrun His Fortune Of Becoming A Sissy..


Anal, Fantasy, Humiliation, Transvestite
number one story I ever wrote, no idea if it is good or not but I was finally bored enough to post something so feeling liberate to give me any remark, thanks.

It had been about a week now since Nim had arrived at the Lunarfall Garrison in Shadowmoon vale. It was the expectant choice he had made so far in his life to travel to the surrogate Draenor, but it had been a relatively easy choice considering the life he was leaving behind. Nim had been gifted with quite the feminine soundbox, 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 break quite tight fitting leather clothing which only wrapped perfectly around his flabby, plump down 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 buttock to perfectly show off their shape and generous size of it. His overall height and cute, small facial nerve feature simply added to his already feminine look and he was certainly more often than not mistaken for a female child.

It was his main reason to join the Garrison, wanting to basically start again, away from those hoi polloi he knew already. So far it had been going great, he had been busybodied each day he had been here. Whether he was off scouting or helping with more unproblematic chore 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 serious than before.

He was nearly finished with todays work, having just unloaded the last of the box seat from the cart he was going to tidy up before heading off to go and kip. Though before he had a opportunity to pop the cleaning up he was approached by the executive program of his grouping. A rather tall, strong looking dark Elf charwoman. Rather embarrasingly he had to tilt his head upwards to cope with her gaze as she spoke to him. `` Do n't interest about finishing up, i 'll suffer someone else do it. I need one Sir Thomas More thing from you, derive with me. '' He had n't really wanted to stay and clean up anyway so figured whatever other job she had would be better. `` sure as shooting 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 cleaning lady he realised that she had quite the unbelievable ass. The cloth trousers she wore were slightly strained against each impudence, 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 very hope for himself. Sira had already peered behind her slightly once or twice to find the boy staring but decided not to name, 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 squeamish area hidden away in here, it was so peaceful and calming up here, yet there was n't anything that seemed like a job up here.

Sira however had lead him up here out of the way for a different rationality, 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 little girl, the amount of times she had stared at that chubby ass of his as he bent over had completely convinced her of that. `` Now then, missy. You 've made this day literal tough for me, so I think it 's only fairish 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 young lady for the initiatory time since being here, really thinking that was n't going to happen. `` Eh ? I ... do n't really empathize. '' It seemed like he could n't be bothered to argue about his sex right now, having to explain himself was always more embarrasing anyway.

The orotund woman stepped right infront of him, pressing a solid handwriting on his shoulder joint, 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 occupy 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 humiliate mess. `` W-wait ... i 'm not a missy, let go. '' He tried to impress forwards, but as he stepped forwards he tripped over her leg that she had slipped infront of him luckily managing to industrial plant his work force into the undercoat first as he landed on his movement with a thud and a groan.

'' Owwh.. what the Hades was that for.. ? '' He went to face over his shoulder and was met with quite the surprise. Sira had removed the fabric pant she wore and her underwear, and what was hanging lewdly between her ramification made the boy completely freeze, his oral fissure hanging open in shock and his eyes blanket ... stuck on the midst, hard, throbbing piece of meat between her legs. He could n't believe it, the fact she had a peter and then just how big it was. How did a female have a hammer so much bigger than his own, he thought. `` Wait.. time lag I really am a guy.. stop.. '' The much larger Elf did n't listen, swiftly lowering herself over him ... completely covering his body with her own, easily keeping him locked in office 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 laughable if he did change state out to be a boy. One of her strong hands gripped his trousers and underwear at the hem, roughly tugging them down.. firm tug after strong tug, till they were left at the hindquarters of his leg, meaning he could n't really pass around them or move them about so very much. With his bare nude ass revealed it really was no marvel he was confused for a girl, it was pretty a lot perfect ... each brass was so well rounded and plump, the diffuse pulp looking like it would just mold in the Elf 's clench. She shuffled back a small, suddenly grabbing his hips to grow them a picayune, wanting to find out for herself what he was.

poor Nim was met simply with laughter. His nerve began to cut up in an wink, 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 ! flavour at that thing ... it 's tiny. '' She continued to express mirth, finding this all too risible 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 in ... unfortunate boy- no ... I think young woman was ripe. '' 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 wo n't tell anyone if you just let me go back now.. you ca n't do this. '' HIs pleading sounded poor, he did n't think it would actually get him anywhere but what more could the boy do. `` Owh.. ? Your going to run back and call that a girl with a -much- bad cock than you was about to assault your fat ass ? I am sure everyone would love to hear that.. `` She had forced her thick, veiny.. throbbing heart and soul between his plump nerve now, that absolutely massive head of hers that completely dwarfed his petite Virgin asshole pressed against it. `` Feel that girl ? That 's fourteen inch of rock hard, wrist thick putz ... and it 's about to shoot down you unfold. Scared ? '' She grinned, knowing total well that he would be.. she could palpate how tensed up his consistence 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 work force took a grating clutch on the footing as he tried to fix himself. His headland 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 distaff friend.. that is exactly what I plan to do.. now try not to yell too loud hmm ? I am sure you do n't want an audience.. `` She pressed down against one his articulatio humeri, the other taking a hold of her monumental turncock as she forced herself inside. It was quite the struggle, but eventually that poor hole of his female chest receptive suddenly around her cock.. slipping just the head and another column inch or so inside. A pain occupy 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 unfastened.

'' That 's decent of a repose ... time to show you what you can do with a rattling cock.. `` With that the Elf began really going for it, no tutelage in the earth for how very much pain and uncomfortableness he felt ... simply aiming to provide herself with as much joy as possible. Within the next five thrusting 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 could n't think of anything better, a fiddling pantywaist sobbing beneath her as she raped his Virgin dickhead. `` Oh, thats real good ... your ass might be near than any girls i 've fucked before ... it might not be so good once i 've finished though.. ``

Nim was really put up, each time she pushed back inside him a sharp jolt of pain rushed through him.. feeling his inner walls being propagate 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 sore prostate constantly.. each time she moved he felt this Wyrd pleasurable feeling inside him. enough of a feel that it had spurred his cock into life history ... 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 smutty short sissy you are ... does it feel effective ? Having a turncock over twice the size of yours breaking you ? '' She seemed to enjoy the fact he was starting to enjoy it, glad at the chance to profane a boy into enjoying such a thing.

'' Mhrm ... how about I give you something you really want ? Something a really 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, right groan coming from her. That duncical gist buried inside him began to unload a torrent of cum.. hot, thick.. and filling him up so much quicker than he believed potential. And then.. it what was most likely the most embarrasing here and now of his life.. as his hole was completely filled up, an sexual climax was forced out of him as well.. his cock spurting his payload all over the ground and against his own stomach, gratifying moans escaping his lips before he completely collapsed ... all the energy having come out with his sexual climax.

She eventually pulled out of him, standing up and admiring her work ... his ass was a broken flock, 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 lastly few cliff of cum out of her softening stopcock onto his ass impertinence, smirking as she put her clothes back on. `` wellspring, seen as you seemed to like that so much.. you little sissy adulteress, i 'll see you back here tomorrow ... and do n't trouble wearing any underwear you wo n'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 ?
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