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This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments, ideas and feedback are welcomed and sought after!

*****

Cynthia spent the first few days of the week getting Nicholas accustomed to anal orgasms. His protests we're quiet vocal when she informed him he would not be let out of his chastity cage during these attacks on his prostate. Not getting off was equally unacceptable to him, and so each evening his aunt would drop by and have him get on his hands and knees, pull his panties down and would dildo his ass. She quickly learned the right spots, the right thrust to get him to squirm and do whatever she would say. She would bring him to the edge, precum dribbling out of his cage while whispering more obscene and gay scenarios through his head. Once he finished dripping loads of cum onto the sheets below them she would have him lick it up directly, reminding him to get used to the taste.

On the second night, she coaxed him into thrusting against the dildo for his pleasure. Despite his claims at straightness, Nicholas was quickly losing that battle, because he was experiencing pleasure with things in his ass. He believed this to really be a deal, and he wanted to have sex with Cynthia but he at times was enjoying himself. Perhaps he simply liked anal play? But why was he so ashamed? He wasn't the things she was saying he was, didn't want to be. But it could feel good sometimes.

Still, things were odd for Nicholas. After his adventures this weekend, he felt like those looking at him knew what he had been up to. Never the most social, he felt the women at university were looking at him differently as well. He avoided making eye contact with people as much as he could get away with it. He would end up glancing downwards, often letting his eyes rest on the crotches of men he would interact with, imagining what his next evening would be like.

The third evening was a difficult one for Nicholas. With the dildo lubed up and lodged in his ass, pleasantly stretching him out, his aunt offered to have the cage removed. He had been playing along nicely and she was almost at the point of trusting him to only masturbate to what she allowed. But just to make sure she could trust him that much, he'd have to let a man fuck him. He argued, and she reminded him she had promised to give him the full gay experience. Surely he couldn't have that without actually having sex with a man? Nicholas did want to get out of his cage, and he wanted to get off, and with enough humiliation and need to orgasm he caved. His aunt had squealed and clapped about how much fun it would be as he licked up all the cum that had squirted through his cage onto the sheets.

That evening, after work he waited patiently for his aunt. It was strange to him how in such a short period of time he was now comfortable sitting on his bed in nothing but his chastity cage and panties waiting for his aunt to show up. She didn't keep him waiting long. When she did, she seemed happier than usual as she sat down beside him. She made quick work unlocking him as per her promise, then pulled out a tablet.

*quot;After this, I can totally trust you, Nicky. I know how horny a young faggot can get, and that must've been so hard. Now, ready to pick a man to take your anal virginity?*quot; loading up Craigslist.

Nicholas for the moment was just content to be unlocked. He briefly considered backing out with his penis free. Instead of waiting for an answer, Cynthia went ahead and went to straight to the casual encounters section, specifically for gay sex. She could see his eyes scan down the list of ads displayed in front of him. He could touch himself again and he wasn't going to stop now, he was starting to crave the shame, and want more of it.

*quot;How about this one?*quot; she asked, clicking on an ad *quot;Horny Man Needs Relief.*quot; A picture of the man's body was missing his face, but his physique was average at best, and his dick was equally average. Not that that would be a problem for Nicholas in the future, he'd have sex with men of all body types and lifestyles. Nicholas just shook his head. *quot;Are you sure you can afford to be so picky? You're just a faggot anyways.*quot; She watched his hand squeezing himself through the fabric of his panties. *quot;Or maybe you just want a certain type of man? Is there a type of man that turns you on, Nicky?*quot;

She browsed through many ads with him, gaging his reactions. She made sure to hit as many ends of the spectrum as possible from the guys who just wanted to get sucked off to those into leather and latex and BDSM. Special attention was paid to the postings with pictures. She wanted him to get used to naked men's bodies as much as possible, and associate them with feeling good. That staring at men's bodies and genitals was as natural as browsing through Tinder for girls. Eventually Cynthia guided him towards silivri escort one ad in particular, *quot;Cherrybuster*quot;

The man inside was in his forties, though his hair was still dark, as evidenced by a dark sheen of hair over his chest and stomach, as well as surrounding his cock. His posting listed that he enjoyed breaking in first time faggots and turning them out. While not the ideal muscular body, there was no doubt he was significantly more manly than Nicholas could ever be, the contrast was that stark. *quot;Now, that's a MAN, no doubt about it. I know he's not super muscular and all, but I think it'd be hot to see him fuck you. Would you like that? To make gay love with a real man? You're going to do it, if you want to honor our deal and keep your penis free. And that man seems to like playing with the new faggots like yourself.*quot;

Nicholas nodded his acceptance, lost in the feeling of the moment. It was sort of all for play, hopefully something she'd back out of as he played along. When she started to reply, and he understood this could and would really happen his penis stiffened painfully hard. She responded for him:

*quot;Hello, Cherrybuster,

I am a twenty two year old faggot in hiding. My aunt is helping me come to terms with accepting that I am a gay male. I've sucked a dick, but I would very much like to have my first full homosexual encounter with you. I promise to be very fuckable for you, my aunt made sure of that and would like to witness.

Just Another Faggot.*quot;

Nicholas blanched inside when she hit *quot;Send*quot;. How could he let a man fuck him? One almost twenty years older than him none the less! Did he want to fuck his aunt that badly? His little dick was so hard, squeezing it through the fabric of his panties. The dildo could feel good. The thought of being bent over and fucked rattled around inside his brain. How would the real thing feel? But he couldn't help but feel it made him lesser, that only faggots liked getting fucked, and he would be one then. But some men liked being pegged, having their girlfriends fuck them, so they weren't gay. Prostate orgasms felt good, liking them didn't make you gay, bi at best.

Cynthia noticed her nephew's discomfort. She had been marinating him homosexual activities and humiliation. He had definitely had an interest before she came a long, but nothing like what he was doing now. His free thoughts were filled with questions about his sexuality, cocks, his new freedom, being caged, wondering if he really liked men. He was not going to say no to anything she wanted, with the right push. Which was why she had made sure the ad that was replied to was a plant of hers. *quot;Cherrybuster*quot; was going to give her nephew a very memorable evening. He knew what to do, in detail, and was quite amenable to it.

It wasn't long before a response came. Definitely interested, though he would like to see a picture first. He shared another of his cock, his hand wrapped around the base. *quot;See? That's going to be your first cock Nicky! But he has to know we're real, so let's take him a picture!*quot;

Nicholas did as asked, and she had him stand up and with his dick tenting his panties she caught a favorable picture. She showed it to Nicholas, pointing out how gay he looked. The responses came quickly, and after a brief information exchange, he would come to Nicholas apartment in half an hour. He expected him to be clean and showered, as he would be.

Cynthia took this time to instruct him. She didn't let him touch himself anymore, she wanted him nice and horny by the time he arrived. She explained it was his job as a sissy faggot to make sure his man was pleased. She reminded him of his recent cock sucking experience as he may need to use those skills. She pretended not to know what this man would require of him and instead advised Nicholas to simply let the man lead and to follow. Nicholas nodded at the proper moments, wiggling as he couldn't touch himself. What he couldn't understand was his thought of having a man's penis in him, being fucked, was the extent of his imagination. And sure, that would happen, thought Cynthia. She wanted to make sure his first time was a thoroughly homosexual experience and far more than he had ever thought he would experience.

The time ticked down, and Cynthia made sure Nicholas stayed naked except for his panties. She smiled internally at how docile he had been today. She wondered what had gone through his head while he was hiding in the closet this past weekend. Once she had acquainted him to the dildo, he seemed more willing. Perhaps it was the extreme levels of shame she induced in him, the best and only sexual experiences he had up to that point and he wanted more. *quot;Remember, honey, I am going to make sure you get the full gay experience before you get a crack at my cunt. He knows you're new to being a faggot, but I made sure to know you were ready for a real man. No, don't try and deny it, those panties don't hide your şirinevler escort erection very well.*quot; She said.

When the time came, it was Cynthia who answered the door letting her confident in. Nicholas was sitting on the bed further behind her, eyes on the floor.

*quot;Damn, this is actually real. You ain't half bad either, lady.*quot; He said. His voice was deeper and a bit gravely. Cynthia grinned at him in response, *quot;Maybe some other time, but tonight's for my nephew. He took some time but when he saw your ad he told me it was time. He wanted to have a man inside him instead of a dildo. To try it, at least. I think he's more than just curious though.*quot;

Nicholas looked up as if to contradict her, he had never said any of that. Instead he saw Ben. He was in casual business slacks and a buttoned up blue shirt. He seemed solid, and perhaps a few inches taller than Nicholas himself, but took up more space. What he hadn't expected was a dark black moustache. His skin was slightly bronzed, and it looked as if he hadn't shaved in a couple of days. His nose was neither prominent nor understated and his eyes were blue under arched brows. He didn't look specifically old but neither did he look young. This man was going to fuck him. He resisted the urge to touch himself as his aunt had advised him.

Ben looked him in the eyes, looking him over. *quot;Well, aren't you one pretty little boy in panties.*quot; Chuckling, and Nicholas blushed. *quot;Well, stand up boy. Let me get a good look at you.*quot; Nicholas slowly complied, feeling awkward being stared at. Or lusted over, really. Clearly Ben liked what he saw, nodding in appreciation. He motioned for Nicholas to spin around as he stepped closer. The panties accented the natural curves of Nicholas ass, and Ben didn't hesitate to grab one of Nicholas cheeks, almost making him jump. He gave it a gentle squeeze.

*quot;Anyone ever tell you that you have a nice ass?*quot; he muttered under his breath. Nicholas didn't know what to say, no one had ever commented on his appearance, especially naked, and especially not another man.

*quot;Well, I can tell you no woman would've told him that. I smelled faggot on him, and if I can, so can others. He's had more luck with dick than with pussy, and deep down he knows there's a reason for that. I'm not sure he'd ever even be able to get a date.*quot; Cynthia said.

Ben let go of Nicholas' ass, moving around front of him, tipping his head up so he could look him in the eyes. *quot;Oh, I don't think he'd be able to seal the deal. But I think he's pretty for a faggot. Are you a pretty boy, faggot?*quot; Ben asked him.

Nicholas heart was pounding, he opened his mouth to respond and Ben took that moment to lean down and kiss Nicholas full on the lips. Nicholas' body stiffened as Ben's lips pushed into his. Ben let go of his head, slipping his arms around Nicholas. Nicholas had not been expecting this at all. This seemed far, far more gay than being fucked would be. He was embarrassed at how obviously aroused he was by it all. Ben, however, knew what he was doing. His hands slipped down Nicholas back, and Nicholas adjusted his head sideways. Ben's moustache was prickly and rubbed against him as he continued the kiss. Somehow, Nicholas responded, pushing back. He knew he shouldn't be kissing another man, especially when had hadn't even kissed a girl yet. The thought crossed his mind that he might never, what girl would want to kiss a homosexual man. His penis throbbed.

Ben broke the kiss, grinning. *quot;I think you liked that.*quot; And Nicholas blushed deeper than he ever had before. He didn't know if he liked it, but he knew he didn't dislike it. Even if it was from a strange man from Craigslist. Ben unbuttoned his shirt, tossing it on the floor. His chest was as advertised, dark hair matting his pectorals and down his stomach. He sat down on the edge of the bed, motioning Nicholas over in front of him. Ben simply reached out casually and fondled Nicholas balls with his hand through the panties. He closed his fist around the straining bump and Nicholas shivered. *quot;You sure seem to like me touching your dick. I've known some faggots in my time, and they all like other men touching their penises.*quot;

Nicholas' flush was staying pretty constant though this time it was fueled by shame as much as the feeling in his penis. Since he didn't know what to say, he said nothing. Ben stopped groping Nicholas' crotch, instead hooking his hand in the band of his panties, and tugging gently nearer. Ben opened his legs wider, *quot;Sit down.*quot; Patting the spot between his legs. Cynthia watched as her nephew obeyed, sitting himself on the edge of the bed. Ben placed his hands on Nicholas' hips and pulled him nice and close, so their bodies were touching.

With his hands roaming over Nicholas' body, how closely pressed together they were, Ben let his cock react. Nicholas' eyes widened when he felt something shift near his ass. He almost pulled away, but Ben held him in place. *quot;Sorry, şişli escort does that bother you?*quot; he asked innocently as his hand found its way inside Nicholas' panties.

Nicholas' could've answered, but his aunt chimed in his place.

*quot;Of course it doesn't. He's just very repressed. He only jerked off to gay porn in secret. He said he liked girls, but well... as you can see, I think he likes something else. I think he likes men. I think he likes men's bodies. Basically, I'm pretty sure he's a flaming homosexual.*quot; She responded.

She watched Nicholas face try to remain passive, but she could see his face tightening as she spoke, or as Ben's hand squeezed his penis while another hand idly played with one of his nipples. If they were just alone, she was certain he would be offering up all kinds of protests, but with a man there he couldn't bring himself to offer any resistance. Especially when it was starting to feel very nice. True, Nicholas had not imagined himself in this scenario, especially not with a man. He found himself arching his hips to push his penis against Ben's had even harder. The result was that Nicholas was grinding his ass against Ben's crotch and this wasn't going unnoticed.

Ben placed his hands on the front of Nicholas hips, his hands slipping down but not touching his genitals, massaging the insides of his thighs, *quot;That's a good faggot. Keep using your ass to get me hard.*quot; And Nicholas did just that. He tried to imagine how he'd want it done, and do that. He was surprised he hadn't cum already even from the friction of his panties against his penis. He was very warm and it just seemed so wrong. But he did enjoy it, feeling a bulge forming, and unthinkingly putting in effort.

Cynthia watched as Nicholas actively tried to turn Ben on. He would swerve his hips and placed his hands on Ben's thighs for leverage. Perhaps he had thought his first sexual experiences would be with a woman, more than likely. She wanted to establish positive male attention with him feeling good sexually. And the future shame that his first time was with a man, not a girl. Not even one he liked, just someone picked up from Craigslist because he felt inferior to him.

*quot;Go ahead, baby. It's ok for you to stop hiding. Why don't you ask Ben here for what he you wanted? That you wanted to be very fuckable for him? You want him to help you be homosexual? Would you like a little bit of dick now, darling?*quot; she asked.

Nicholas quietly said *quot;Yes, please.*quot; He could feel Ben's cock pushing against his pants, and he knew it was because of him. His own was throbbing from the excitement and the fact that he was enjoying the situation. He tried to imagine he was doing this with his aunt, what he would do to her, but kept getting pulled back into reality when he felt Ben's chest hair against his back or his hands on his hips. He knew what to do as Ben nudged him forward, off the bed. Nicholas' shakily dropped to his knees, scooting closer. He kneeled there, not moving until Ben spoke up *quot;Go ahead. Take it out. We all know you want to. Faggot.*quot; Ben's legs spread wider, as if to give him access. This wasn't any gayer than what he had already done, so that made it alright in Nicholas' mind.

Cynthia watched as her nephew reached up to unbuckle Ben's pants. She casually rubbed herself while they were engaged. Nicholas tugged the pants down, further and further to reveal a semi hard cock in a pair of briefs. Cynthia was surprised how emotional this was for her as well, she had actually managed to manipulate her nephew into pleasing a man. She found herself holding her breathe as Nicholas removed the briefs as well, gently reaching up to wrap his hand around Ben's cock.

Nicholas began simply by feeling Ben's cock. It was not fully hard but he could feel it filling in his hand. While he was squeezing and pumping Ben's cock, his aunt went ahead *quot;Make sure you get it nice and wet, cocksucker. You know where it's going to end up.*quot; She said knowingly.

Nicholas had to angle Ben's dick downwards a bit to get it to an angle he could wrap his lips around it. There was an intense male musk that filled Nicholas' nose. Remembering what he'd done with the first cock he'd sucked, he tried to replicate it here. He made sure his lips covered his teeth as he felt his mouth fill up with dick.

*quot;That's a good faggot. Keep sucking that dick.*quot; Ben praised him, running his hand through Nicholas's hair. Also controlling the rhythm, seeing how far Nicholas could take his six and a half inches as it swelled up. The only sound to be heard was Ben's praise and sucking sounds coming from Nicholas. Ben's dick seemed even harder than the first one he had sucked, and he wanted to do better. He let saliva pool in his mouth, a thick sheen starting to cover Ben's shaft. A couple of times Nicholas got close enough that he could clearly see Ben's leathery ball sack.

*quot;Would you like to try and tell me how you like women, now? Or is your mouth too full of dick?*quot; she mocked him. Ben held Nicholas' head down a bit, the drool seeping out around his dick. *quot;What do you want from Ben, Nicky? Do you want his sperm in you? Do you want a real man to fuck you? Do you want him to shoot his load deep inside you? Go ahead, it's ok to say it out loud. It feels good when you admit who you are.*quot;