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Chapter 9 - Side story1 -Issei- (yaoi,NTR,Sissy)

My first work ever depicting the main cast of DxD ending up in various sexual situations. It will feature various niche fetishes as the story goes along with a conclusive ending as they get more corrupted.
The work is finished just needs some heavy editing. That i try to do to the best of my abilities.
Please read the tags as it will contain some very heavy content.

Chapter 9 - Side story1 -Issei- (yaoi,NTR,Sissy)

Chapter 9 - Side story1 -Issei- (yaoi,NTR,Sissy)
Issei sat inside his room alone, after the girls told her Rias was trapped. He at first blamed himself that he should have gone with them. He should have done more for them but he could not bring himself to really care for some reason. Well he knew the reason as he is nore blind or deaf. Their change didn't escape his notice. He still remembered at the sights when he spied on them numerous times. The memory of the girls being destroyed by that group of bums still sent shivers down his spine. And that was only one of the things Issei wished he never seen, but he really can't blame them only himself as he was not capable enough. Undressing he dispelled his concealment and stood before his mirror. As he looked in the mirror, he was reminded why. Gone were the young manly body and in it's place stood a womanly figure. At first he let his hair grow out as he found it cuter to have a long one. His long bangs framed his now feminine face perfectly, the high cheekbones, plump lips gave him the visage of a young beautiful woman. In his spare time he even learned how to put on some make up.

The sight before him turned him on more than anything else before. Running a hand through his chest, he let them rest on his now b-cup sized breasts. As the once renowned Oppai Dragon he had to admit that they were beautiful. They were perky and tender to his touch as he squezed them harder. The feminine moan that escaped from his lips only made his face redder. Running his hands further down through his slender waist he stopped at his ass and hips. They were so big that he would not find it out of place on Rias or any of the woman he knew. Bending forward he ran his hands along his juicy thights and long slender legs and brought his hands back to his penis. No matter how turned on he was it just refused to stand up anymore. In it's place was a yerning to be filled, that was a completely alien feeling for him at first but he managed to cope with it, thanks to Kiba and Gasper. Reaching under his bed he pulled out a box that contained a set of crimson lingerie with thight high stockings and a pair of 6 inch platform highheels with ankle straps. He quickly donned them as he started shaking with exitement. Seeing himself in the mirror shame and exitement washed over him as he thought about what the girls would think when they see him now. Knowing them they would propably invite him into one of their session, which he was not ready for at least not yet. From the bottom of the box he lifted out 2 sex toys and a bottle of lube. One of the toys were a 10 inch long black dildo completely life like that he ordered from one of the fallen angel companies, the advertisement said it was molded after a real porn stars dick. The other was a chastity cage which was barely 2 inch long. After he lubed his penis up he put on the cage. It was a very thight fit as it squezed his penis and balls. With everything in place he made sure he locked his door pulled in his curtains and started playing one of his recent recordings. As the video showed 3 girls walking through kuoh park, he started lubing up his dildo and asshole. Slowly he started lovering himself on the dildo pushing it's head through his entrance. Looking back at the monitor he cupped his breasts and started slowly moving up and down on his dildo. The sight of the 3 woman he loved being cornered inside that dirty toilet made his penis leak it's first drop of cum. Seeing them first rimming the homeless, sent a jolt up his spine as he started to bury his dildo deeper with every thrust. He started to ride his dildo harder when the first bum thrusted inside Rias. Her cry of joy filled him with a feeling of impotence as his penis shot his first jet of cum on the floor. Unable to touch his dick he changed postition to better simulate what Rias gone through. He stuck his dildo on the wall and started trusting back on it, to the rhythm of his girlfriend being fucked. Seekng the hobo trusting wilder, he angled the dildo towards his prostate and started battering it harder. When the bum cried out Issei trusted back on his dildo harder and let the pleasure wash over him. Just as he heard his girlfriends pussy being filled with another man's semen, his own climax washed over him as his penis shot jets of cum one after another. Just as the bum finished filling her up and pulled his dick out, his cum started trickling out of her vagina. At the sight he quickly got on his knees and started licking up the spilled seed from the floor. As gathered his seed inside his mouth, he imagined he licked the old men's cum out of her pussy. When he gathered all of his seed he sloshed it around in his mouth and swallowed it. The feeling of his own cum running down his throath made him burn with need again. Standing back up he started trusting on his dildo again. Looking at the timer of the video a jolt was sent up his spine. Looks like he is gonna by there for the whole night again.

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