Revenge is Sweet

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James certainly looked impressed when he answered the door to see "Helena" standing daintily on his doorstep, he was dressed in a blue shirt and navy slacks. Although he still didn't like James' personality and found him self absorbed, a part of Henry had to admit that he looked pretty good and he could begin to see why women like Sadie were attracted to him. James ushered Henry into the living room and Henry found himself suddenly very nervous. Although he had come to accept that as Helena he was really turned on by sucking James' cock and was really desperate to do it again, in the cold light of day, without any alcohol, he began to wonder whether he could sum up the nerve to do it. He sat demurely on James' sofa, his sofa as he recognised it from his previous life, with his legs crossed, the long, smooth shape of one leg dangling enticingly down to his pink sandals. James sat beside him and they engaged in awkward conversation for a while. Henry couldn't really look at him and his mind was blank for anything to say as he felt quietly embarrassed. He could tell that James didn't really know how to handle the situation, he wasn't that great at talking to women, Henry knew that from before, and they both knew that they were really here not for conversation but for sex and neither was quite sure how to initiate it.

Seeming to tire of his attempts to start conversation, James leant over and kissed Henry on the lips, forcing his tongue into Henry's mouth which involuntarily opened to allow James' tongue in. Henry was surprised and a little taken aback and for a moment could do nothing but let James' tongue invade his mouth. James seemed to take "Helena's" inactivity as a sign to continue and he leant over folly, pushing Henry back onto the sofa, and kissed him again, this time caressing his false breasts through his sweater. Once again, as he had in the bar, Henry found himself letting out an involuntary moan of pleasure at James' kiss and the closeness of his touch and was surprised to find his lips still reaching out for James' as James pulled away. He grinned in a leering way that reminded Henry of the barman the week before.

"You like that, don't you bitch?" he said and Henry astonished himself by nodding in agreement.

James was now unbuttoning his shirt to reveal the muscular chest that Henry hadn't seen since the day that he had caught James with his wife. Right now, while he was Helena, he felt a little thrill of excitement at seeing it and bent forward to start kissing James' chest leaving little pink lip marks on it. Meanwhile, James was violently pulling the tight pink sweater over Henry's head and he experienced a momentary worry that it would dislodge the blonde wisps of his wig and reveal his true identity, but he was fine. Henry now leant back on the sofa, dressed in just the grey pleated mini-skirt and the skimpy pink satin bra that was all that held his fake breasts in. James bent forward to kiss his lips again and as he did so this time Henry could feel his hands straying up his smooth thighs and inside the pleated mini-skirt towards the sexy pink satin panties and the secret they contained. Henry suddenly realised that if James got any further his secret would be revealed and his plan would be ruined. With his nerves now conquered by a more pressing desire he pushed James away from him and rapidly unzipped his pants and dropped them and James' boxers to the floor until James' athletic body was revealed, naked, before him with his firm, erect cock jutting out before it.

Henry got to his knees and began the same routine as in the bar the week before, slowly stroking James' shaft while planting soft kisses around his head, flicking out his tongue, he drew a string of pre-cum from James' cock and slurped it up like a string of spaghetti. Naomi had agreed to bring Sadie in around 4:00 that afternoon and it was barely gone three. Henry knew that things had gone far quicker than he had expected and if he was going to allow Sadie to catch them in the act then he would have to slow things down. So he began to playfully tease James' cock and balls with his tongue and pink manicured fingers, but James was having none of it. Holding Henry by the back of his blonde wispy wig he pushed his hard throbbing cock between Henry's lips, Henry offered little resistance as James shoved the full length of his cock down Henry's throat before withdrawing and thrusting his cock back into Henry's mouth. Although James had enjoyed the blowjob that Henry had given him in the bar, this time it was James that took total control, violently thrusting his cock into Henry's mouth while he held the back of Henry's head for leverage. Not that Henry was offering up too much resistance to this, as James' cock slid in and out of his mouth he found himself ever more turned on, moaning in pleasure as he used his free hands to caress his breasts through the thin pink satin of his bra while James groaned with joy himself and started to say things like:

"That's it you little slut, that's what you want isn't it bitch? You want my cock inside you don't you?" Henry could only moan appreciatively at this talk as James began to thrust his cock more and more vigorously into his waiting, anticipating mouth.

Henry was glad his cock was strapped down again as he knew this whole experience was turning him on, there was no point denying it now, he was loving taking this man's cock in his mouth, dressed as a sexy, slutty woman. It didn't take many more feverish thrusts into Henry's mouth to send James' over the edge. Once again, as he had done in the bar, he grunted as his cock twitched and spewed it's tasty warm juices deep down Henry's eagerly awaiting throat. This time Henry eagerly and slightly more skilfully managed to lap most of it up before letting James withdraw and spurt a little more across his face. He licked around his lips, savouring all the extra cum on his face, giving a big grin of pleasure at the experience that he had just had.

James had pushed Henry down to the floor now and was kissing along his neck and down towards the false silicone breasts encased in the pink satin bra, his cock was already growing hard with arousal once more and a flush of pride rushed through Henry's mind that as Helena he could have such an affect on men. Once more James began to stroke Henry's smooth, bare thigh, progressing up the grey skirt towards his pink satin panties and the surprise they contained. Henry realised that he would have to stop James now and reveal his secret, he was still incredibly turned on by all this and didn't want to do anything to break the moment but didn't know how James would react when he found out and so wanted to reveal it to him first. He pushed James back off him and stood up.

"There's something you should know about me," he purred in Helena's feminine voice, he was so used to using it and it felt so right to do so dressed like this that he didn't stop now.

He reached under the pleated grey skirt and pulled his panties down to his ankles, unstrapping his cock as he did so. He stepped out of the sexy little pink satin panties trimmed with white lace so now he was dressed in just the matching pink bra, the grey pleated mini-skirt and strappy pink shoes. Standing up straight, he lifted the grey mini-skirt to reveal his own cock, standing as erect as James'. James' face fell with shock for a moment but Henry noticed that his cock didn't but remained standing aroused and excited, if anything more so now.

"Helena, y. .you're a shemale?" he stammered as Henry realised that James still hadn't realised it was him but was instead assuming he'd picked up a shemale.

Henry realised that he could use this assumption. There was something he wanted right now, something he felt he needed to make his womanhood complete, he could no longer think about revenge, about Sadie. Such things didn't matter to him any longer, he had completely forgotten his reason for being here. All he wanted now, all he desired, was to feel James' firm hard cock inside him, all he wanted was for James to flick him like a woman.

"Does that bother you?" he purred, particularly enticingly.

James' cock was still quivering and erect and Henry leant down and began to stroke it as James gave a moan of pleasure, he didn't seem to be giving much resistance to being jerked off by a shemale so Henry moved on to giving his cock a quick suck, making sure to slobber on plenty of saliva, he knew that it would be needed to provide lubrication on his virgin ass. As James was offering no more resistance and indeed was moaning with pleasure, Henry decided to take the initiative and pushed James' naked body to the floor, his erect cock sticking up from his body. The situation of earlier was totally reversed as Henry now took the lead, spreading his smooth, feminine legs he sat himself astride James' athletic body and, hoisting his grey mini-skirt just a little, he began to lower his9ert ass onto James' large, erect cock. He gave a short, feminine squeal of pain as James' cock, however lubricated his saliva made it, squeezed into his tight virgin anus. Gradually, and painfully, he managed to impale himself totally on James' cock, Henry felt as if it was stuck right deep into him in a way that, although painful, made him, somehow complete and fulfilled. Slowly he slid himself back up James' cock until he felt a disappointing feel of emptiness in his ass, before ramming himself back down onto James' firm, hard member. The combined feeling of pain and total ecstasy as James' cock once more filled his ass was so astonishing he gave out a squeal of joy and almost felt himself cum right there. As the total extremes of pleasure and pain began to die down a little, he began to grind himself up and down on James' cock as if he was the kind of slut who had been riding men all her life. James, for his part, seemed no longer to care whether "Helena" was really a woman, he was having a great time and reached up to fondle Henry's pert, large false breasts through the thin satin bra. Henry moaned and screamed like a whore as he continued to grind down on James' cock:

"Fuck my ass you stud, fuck me like the slutty whore I am. I want your cock deep inside me," he screamed, "I want to be fucked like a woman."

As he could feel James growing towards a potential climax, Henry lifted his pleated mini-skirt further and began to jerk off his own throbbing cock in time with his riding James' until James, for the second time that afternoon, grunted with pleasure and let his cock explode, blowing a huge load of warm, sticky cum to fill Henry's ass. Prompted by James' own ejaculation and his stroking of his cock, Henry felt his cock twitch in his hand and explode, cumming right over his skirt and James' chest right up to James' face, Henry noticed a look of pleasure on James' face as he caught Henry's cum on his tongue and tasted it. It was the greatest pleasure of Henry's life so far, continuously spewing his cum all over James' hot, athletic body while his ass continued to be stimulated by James' cock inside it and the huge loads of cum James filled his ass with. Both of them continued to ejaculate for what seemed like forever before James' cock finally dropped, limp from Henry's ass.

"That was amazing Helena," James sighed as they lay on the living room carpet together, Henry lapping up his cum from his wife's lover's chest, "Your ass was sooo tight, it felt extraordinary. I've never cum like that before in my life."

Henry smiled and pulled James' face towards his, planting a deeply passionate kiss on James' lips, using his tongue to push his cum down James' throat. James offered no objections and, indeed seemed to enjoy the kiss very much. So much in fact that for the third time that afternoon his cock began to twitch and become erect.

"You think your orgasm was great," purred Henry, "You should try it my way!"

"What's it like?" said James, licking Henry's cum from around his lips, "What does it feel like?"

"Oh, it's the most intense pleasure in the world, you've never felt anything like it," suddenly Henry was struck with an idea, "Now's the time for you to find out," he purred.

James looked confused for a moment before he realised what Henry was suggesting and backed off a little, his face deeply anxious and nervy. His cock, however, had totally sprung to attention and it was this arousal, coupled with his own building excitement, that spurred Henry on.

"Trust me, it's amazing. And nobody would ever have to know," he could see James' will weakening, like himself a little earlier he could tell that James really wanted to experience this, so he took control once again, "Just get on your hands and knees."

James' will was clearly broken by his desire now as he got his athletic body onto all fours with his toned buns pointing in the air. Henry licked his lips in anticipation of pushing his cock between them. He spat on his hand and covered James' anus with saliva, then he slowly inserted his pink manicured finger up James' ass. James gave a hum of pleasure and his anus tightened around Henry's finger.

"Mmmm, Helena that feels good," he moaned.

"This is just my finger, you'll have to relax a little to let my cock in."

Henry withdrew his finger from James' ass and James' ass seemed to reach back up towards him, in need of being filled once more. Henry lifted his pleated skirt once more and spat on his hands, lubricating his cock with his saliva before positioning the head of it just about to enter James' ass. After a moment's pause he began to shove his trembling erect cock up into James' awaiting ass. James' virgin anus was so tight around Henry's cock that Henry felt far more stimulated than he ever had fucking a woman's pussy even though it was quite an effort to force his cock into James' ass. James gave a massive scream of pain and Henry could see tears in his eyes.

"Come on, if a dainty woman like me can take it surely a big strong guy like you can," Henry berated him, "Or maybe you don't want it anymore."

With that he withdrew his cock mostly from James' ass and, as he thought it would, James' ass rose to meet his cock, trying to fill the emptiness inside him.

"No, I want it Helena," he said, "I want your cock in my ass Helena, FUCK MEEEE!"

He screamed this last word in pleasure as Henry obliged his wishes, shoving his cock back, deep into James' ass. Soon, Henry was rhythmically thrusting in and out of James' ass, tearing into him with a force and vigour that James had fucked his face earlier that afternoon. The tears streaming down James' face were now tears of ecstasy as he moaned, groaned and yelped with pleasure. Henry meanwhile was almost as turned on by the tight grip of James' virgin ass around his erect cock. That grip only got tighter as James raced towards his orgasm, aided by nothing but the vigorous thrusts of Henry's cock into his ass, and began to scream out:

"I'm cumming, fuck me Helena, I'm cumming!"

And it was at that exact moment that the door swung open and in walked Naomi and Sadie, completely unaware of the shocking sight they were about to see. Caught up in the joy of the moment, Henry had completely forgotten his plan and their impending arrival and was caught as surprised as everyone else by their sudden appearance which was too late to do anything to stop his orgasm as his cock blew its warm, salty liquid up James' ass and James' own orgasm as he ejaculated all across his chest and the carpet. Naomi looked shocked for a moment at how far things had gone before her face re-arranged itself in a smirking grin directed at Henry. Sadie was far more shocked and for a while stood totally still, staring as if unable to believe her eyes. From her point of view, the sight she beheld would have been her lover James, naked, on his hands and knees, being flicked up the ass doggy style by a sexy blonde woman in a pink satin bra and grey pleated mini-skirt. As Henry withdrew from James' ass, his cock still dripping cum and walked across the room to put the tight pink wool sweater back on, James still knelt on the floor looking totally abashed and confused. Sadie strode over and slapped him across the face:

"What the fuck do you think you're doing you fag?" she yelled at him, "Pack up your things slutboy because I want you out of this house by this evening," with that she stormed out of the room, leaving James shell-shocked still crouched on the living room floor.

Still looking abashed, James turned to Henry, a pleading look in his eyes, "Helena. . ." was all he said. "Sorry James, but you're just not man enough for a woman like me," Henry smiled at him and handed him her discarded pink satin panties, "You can keep these as a memento of the day that I popped your cherry."

With that Henry and Naomi strode out of the living room and away from the house, leaving James humiliated, used, naked and stained in cum on the living room floor. Henry now realised his plan had worked better than he could ever have hoped, he'd got his revenge on Sadie, she'd had to break up with James, and on James, who Henry knew would never quite be the same again, and with all that he had broken with all the ties of his old life and launched himself into an exciting new world of sexual discovery.

THE END

Look out for Part 2, "Personal Assistance".

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B3ndoverB3ndover4 months ago

Not believable even for a fantasy storyteller

James19781984James1978198410 months ago

Loved it, I couldn't set it down had to read the whole thing at one sitting

CSXaviCSXavi11 months ago

"he'd got his revenge on Sadie, she'd had to break up with James"

No he didnt... She just dumped James, who given her track record. She was probably cheating on. So no skin of her back. Probably moved her lover in the day after.

AnonymousAnonymousabout 1 year ago

Well, what just happened? Oh, I got the gist of it but where was the real revenge? What happened with James afterwards?

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