He began to enjoy his cocksucking, the queasy feeling it gave him in his stomach, the pleasure from having his mouth full, the smell that reminded him of his new outlook on life.
The next weekend, Cynthia called her nephew over in the afternoon. It was time to start preparing him for the next phase in her ever growing plans. She knew that Nicholas mind was focused on the massive shift in his place in life and the heaps of gay sex he was constantly having. The link in his mind between shame and arousal, between humiliation and orgasms and all the physical sensations was constantly in his thoughts, which kept him occupied. The two of them enjoyed a pair of joints as they talked about Nicholas most recent week. She noticed he seemed much more comfortable when he talked about sucking cock in general or being on the receiving end of an anal assault. It was becoming normal, and he even mentioned some new prospects at school he was interested in.
Once they finished with the weed, she had him follow her into her bedroom. Nicholas was more than familiar with the room where so much had happened, and quickly noticed several large paper bags by the dresser. Cynthia walked over to her nightstand and asked him to remove his clothes, even his panties as she fished around. This was slightly unnerving for Nicholas, wondering what his aunt had in mind for him, his fear of what might be coming only serving as fuel for his excitement, and he quickly complied.
By the time he was completely disrobed, Cynthia had found what she was looking for, his chastity cage. He was instantly aware of all the orgasms he had this past month, and very much did not want to give them up. Cynthia couldn’t help notice the wariness on his part, laughing softly, “Honey, turn around and look in the mirror.” Nicholas did as requested, remembering the last time he had been ordered to look in that mirror. Remembering how gay he looked, and how embarrassed he had been at the time. From his current point of view, that had been ages ago, a different person.
Cynthia stood next to him, “Well, you definitely look faggy, especially all hairless. But, I’m going to be taking some pictures and video of you. I’m sure you’re getting plenty of offers on Grindr and Craigslist, but I think we can do a little better. You’ve definitely done a very good job of being a good little faggot, so I’m going to help you with the next part.” She said, handing him his chastity cage. “Go ahead, put it on. I certainly don’t need to see it.” Nicholas didn’t know what to expect, he usually was allowed to masturbate in front of her he thought glumly as he slipped it on, locking it in place and giving her back the key. He knew he didn’t need to ask, she would take joy in spelling it out for him.
“You’ve definitely been very homosexual, sucking all those dicks, your little late night adventures. But you’re not just any faggot, you’re a sissy faggot. You really enjoyed your evening with Jake, didn’t you? What did you tell me you liked about it so much?” she quizzed him.
Nicholas found his hands covering his caged penis for some reason and answered “Well, I liked worshipping him.”
Cynthia nodded at him, “That’s right. You really liked having a man to please. You were so excited you blew your load the second you were touched. You’re definitely a sissy! But you don’t much look like one, so we’re going to fix that a bit.” She said, reaching into one of the bags and pulling out some lingerie.
This was completely new to Nicholas personally. He had seen it in porn before, but he hadn’t really given it any thought recently. He wore panties, and he enjoyed it. That’s just how it was. “I’m sure your partners find you a fine fuck, after all I did turn you into what you are… That doesn’t bother you, does it?” she asked.
Nicholas took a moment to respond, chafing at his cage. She knew what she had said would turn him on, and answered, “It doesn’t anymore. Thank you for making me gay.” He said, hoping he would please her enough to let him out today.
For a change, this was not what Cynthia had been expecting. It had been over a month since she had gotten him to admit to his new sexual orientation, and he had never expressed thanks. Was he really thanking her for what she had done? But she knew she had a job to do, even though she wanted to reward him, well…. He’d just be rewarded a different way.
“You’re welcome, sweetheart, I really enjoyed it too. I just love the way that you now adore men and want to please them. Those men are far better than you though, and you might need to put in some effort to let them use you, especially if you’re going to spurt so quickly. Any random boy can be a faggot, but not all can be sissy faggots. For that you really, really need to love men.” She left it hanging.
“I do, I love them.” He whispered the admission quietly.
“Do you, really? Do you like how they make you feel when you can play with their cocks? Did you enjoy sleeping in the man’s arms? Or showing off your tattoo to Jake? You certainly were excited about all the kissing, and licking, right? And all those fuckings, don’t you cum good every time?” Nicholas nodded his head up and down to each question.
She handed him a new pair of panties, “Special made, nephew.” Nicholas took it in his hands. It was a lighter shade of purple, but it had a hole in the front. He slipped them on, tugging them up and over his butt. With some adjusting, he was able to make it so his cock cage slipped through the hole, shining brightly. She rummaged in the bag, pulling out a darker purple mesh garter and stockings, passing those over too.
“When us women want to put on a show for our men, we do stuff like this. And since that’s the space you occupy in their life, I thought it would be a good idea for you to do some of the same things, like dressing up for your man.” She said as he slipped the lingerie on. It took him a while, as he had never worn anything quite like that before. He positioned himself to see as much as possible in the mirror, twisting and adjusting to get things the way were supposed to in his mind.
His aunt lit another joint for them to share, standing beside him. She handed it over, and he inhaled. “See, now isn’t that better? Wouldn’t it make you happy if a boy dressed up for you?” Nicholas exhaled, his eyes somewhat red, nodding, “I guess so.”
Nicholas took in his image in the mirror. While you couldn’t see his tattoo from the front, the silver rings through his nipples were clear, and he had to admit that he did not look half bad in the garter belt and stockings. His eyes lingered on his chastity cage proudly on display through the hole in his panties. He looked at himself in the mirror, fingering the ring in his lower lip as well. For a moment he wondered at the sheer absurdity of what his situation had become. As if he could not reconcile who he had been and who he now was, not as it was being reflected right back into his eyes. His penis was already brushing up against his cage.
“There, isn’t that a bit more like the sissy faggot pornography you enjoy?” she asked, flipping through her phone, finding one of the earliest pictures of she had taken of him, showing it to him. “Remember then?” she chuckled, “Hadn’t even had a cock in you then, and look at you now.”
He did just that. Nicholas had a sort of lopsided smile as he looked at himself in mirror, his cage shifting. Damn, he wanted to play with himself. Even he had to admit he looked like a sissy faggot, twisting sideways trying to catch a glance at his “Faggot” tattoo, but he could barely make out the first letter and part of the color of the fire. “I guess I do look pretty gay.” He ventured.
Cynthia nodded, snapping a quick picture. “Yes, yes you do. Still plenty of work to be done there. But for now, you’re going to have to work on being a better sissy. Remember, pussy isn’t your thing anymore. You like men, and sure lots of casual gay sex is normal for a homo like you, but if you really want to please a man, you’re going to have to do better.”
Over the next half hour or so she taught Nicholas how to pose, how to act more seductively. Pictures of him blowing kisses, just the right angle to tilt his head and smile. Him bent over on all fours proudly displaying his ass, one of him on his back, legs lifted and spread while he pulled on his nipple rings and licked his lips. Part way through, she produced a larger curved dildo with no a pair of balls and a solid case, taking pictures of him sucking on it, running his tongue along it and eventually balls deep in his throat. It was a new sort of erotic to Nicholas, as he could not touch himself yet could not become fully aroused either due to his cage. His head was swimming because of the weed, and he found himself both ashamed and proud at how was starting to enjoy it.
However, Cynthia had no intentions of stopping there. She figured she had many possibilities for the types of gay fetish sex Nicholas would end up with, but she very much wanted to reinforce that her nephew’s place was to actively attract and please men, especially sexually. She wanted him to have to settle for anonymous encounters when what he really wanted was to be used by men, to get the only sexual pleasure he would ever have again come from males.
To that end, she began taking videos of him. She would record him with pouty lips as he asked for a “real man” to let him be their cumdumpster. Another on his knees, mouth open and waiting. She had him get on his hands and knees on the bed, capturing his tattoo on the video as she had him turn back and smile at her. Her personal favorite was when she panned up his body, making sure to capture all of him, his stuffed chastity cage clearly visible, then focusing in on his face as he said “Hi, I’m Nicky. I’d really like it if you used me. I promise to be the little faggot you could hope for. I’ll kiss and suck and lick and fuck, I can give you a lap dance or I’d love to eat your ass.”
It had taken several attempts, as Nicholas stuttered over the words, or pausing for a moment. She paused him for a moment, and had him add at the end that he only got off from pleasing men, and that he’d be locked up until they met. It took many more tries, and as Cynthia insured him that he would indeed be locked away until the following weekend, which both dampened his enthusiasm and caused immense frustration, but in the end, she had quite an appealing set of pictures and videos.
Nicholas eventually sat down on the bed, and she tossed him the dildo as well as some lube. He looked up at her, and she looked back down at him, “What? I wasn’t kidding. You’re locked in there. It’s not like you haven’t had orgasms from having your prostate hammered. If you want to get off this week, that’s how it’s going to happen. You blow your load way too quickly anyways. You’ve been humping away without any care to doing your job properly, so you’re going to have to learn how to really please a man with that boy pussy of yours.”
Nicholas eventually settled lying on his back, propped up by pillows. One hand was wet with lube, coating his plastic friend. She had him pull his panties to one side and use his fingers to awkwardly prepare his hole. “Go on, slide it in there.” And Nicholas began inserting the slick dildo into his ass. He was instantly aware of the difference between it and the real thing. He missed the warmth, the muscular hardness, even as he was barely in.
“I’m going to have such a nice surprise for you next weekend, baby. But until then, it’s anal orgasms only for you. Go ahead, get it in there good.” She said, as Nicholas slowly pushed more of the dildo into his anal passage. His arm kept bumping into his garter and cage as he had to curl up, humiliated. He was used to being able to touch himself, and some of his partners had even reciprocated orally, though none had wanted him to fuck them, and now he was pathetically reduced to needing to diddle himself with plastic while wearing women’s lingerie to get off. His dick throbbed painfully against the cage.
Once it was all the way in, he could feel it pushing into his prostate, even before the balls hit his ass. He shifted his weight, pulling it out a couple of inches before starting to build a slow rhythm. “Use your ass. You can squeeze it, and grind it and lots more. This one can’t throb and pulse, but if it did, the only chance you’re going to have to is to get off before you finish making it soft.”
Nicholas looked down at himself as he pleasured his ass. It was a first for him, and the awkwardness of the situation made it difficult for him. He had gotten so used to having a male partner that this simply felt humiliating, using a dildo to pleasure himself. He had never had or wanted to use a toy back when he was straight. Cynthia continued, “Go on, pump it in there nice and good. It’s their pleasure that matters, and some of them will leave you physically unfulfilled. And that’s OK, you’re a sissy faggot. If a nice, big burly man packs your ass with his cum, even if you get off or not, it’s your job to clean him up and make him happy.”
Nicholas was really having a go at himself, the slick noise getting louder as he pumped his ass with the dildo, filling himself all the way to the base. It felt great when he rubbed it into his prostate, which he was going to need as he couldn’t touch his penis. “Maybe if you do a good enough job, you could get a boyfriend. I don’t think the monogamous life is one for you, and most of your lovers would probably be ashamed to be seen with someone as flamingly homosexual as you are, but who knows? Would you like that? Holding a guy’s hand in public? Being his arm candy? Maybe he’d even kiss you in public. And there’s plenty of clubs that cater to your kind. Doesn’t that make you want to be the prettiest little gay boy?”
Nicholas simply whimpered, tensing with the dildo lodged deep in his ass. He could feel his cum leaking out of his penis, dripping onto his cage, and he just kept wiggling his ass. It wasn’t as satisfying as when he could play with his penis or those rare times when a partner sucked on it, but it was better than nothing. His aunt gave him a knowing smirk. “You do look pretty cute like that, dressed up with a dildo jammed in you and your child sized penis locked away in your cage. I bought plenty of those special panties for you, in some very nice pastels. But, I think I’ll get a picture of you like this too.” She said, grabbing her phone again. “Smile!” she said, and Nicholas was able to muster a full smile, like he was genuinely happy. Perhaps he was, on some level, she thought. For the camera, it certainly locked that way.
She let him get dressed after, putting his lingerie and new panties in their bags, as well as several tubes of lube and his new dildo. She also tossed in several ounces of marijuana, as she assumed he would be consuming quite a bit this coming week.
Once he was fully dressed, she brought him out to the kitchen. “So, go ahead and keep your class mates pleased. I know there’s not that much time between classes, fitting in a full fuck might be difficult, but don’t let that stop you. If they just want their cocks sucked, go right ahead, you just won’t be able to play with yourself. The better you get it, the more you can turn them on and let them use you, the more likely you’ll be able to have a nice little cummy.” She explained.
Nicholas nodded, obediently. He didn’t really have an option, and he found he was disturbed by not being able to bring himself to orgasm naturally and pleased that he would still be able to play with dicks. The realization disgusted even him.
“I know your last semester is ending soon, and you really should be studying, but I think I’ll pick some partners for you every night this week. It’s not like you were alone most evenings last week, anyways. We got some pretty good pictures and video today, so I think it shouldn’t be too hard for me to find some men to help you have some fun new gay experiences. I’m starting to think you have a preference for older men, so I’ll see what I can find you.” She said.
Nicholas simply nodded. Right now, he just wanted to rest. His head was still hazy, and he had done so much already, he didn’t see a problem. Another part of him simply thought she was right, he had enjoyed his times with men more than fifteen years older than he was. He knew he was gay now, but it still somehow felt wrong and he felt shame at what he had done, and would be doing. And another, small but important part of him was simply and purely excited at how the prospect made him feel.
What Cynthia failed to mention was that her nephew would likely need to make good use of his dildo for the next week. If he couldn’t get off before his lover of the moment did, maybe he could rouse a second or third attempt from them. He could always use the dildo on himself after they left. She wanted to insure he was desperate and horny enough to be thoroughly incentivized to learn how to use everything he could do to please a man.
Nicholas spent much of the next evening learning how to get off with his dildo. He had tried earlier that day with a quick Grindr hook up, but his efforts to please this particular man had resulted in a fairly quick orgasm before he pulled out, leaving Nicholas unsatisfied. It was not easy, and sometimes he would just give up, it was somehow different from when his aunt was doing her thing. Later in the afternoon a school acquaintance had stopped by for a quick blowjob, and even though Nicholas had happily offered his ass up, it got no attention.
So, he did some research, and found a local erotic store that had a quality dildo for himself. He had settled one that moderately thick and seven inches in length, with a slight curve. Most importantly, the base was solid and the base could use suction to lock on to a surface if needed. He had blushed when buying it at the store, the girl behind the counter he assumed knew what it was for. She knew he was, and that thrilled him.
He found after some trying, the ledge of his bathtub was at a good height for him to ride the dildo. He could control it well enough to build a good rhythm, and push all the way into his prostate. The bonus was the positioning left him directly facing his mirror. Most of the time, he kept his eyes closed as he masturbated, but the sight of himself riding a dildo was too shameful to not look at. Sometimes, he would pose in the mirror, trying to replicate things he had seen when gay pornography had been his hidden secret. He would kiss at himself in the mirror, or tug on his nipple rings while biting his lower lip, and would moan when the need hit him.
When Cynthia caught this on her cameras, she would rewatch these little sessions over and over until her pussy was raw and sore from cumming so much. Things like this were just a reminder that she had truly and permanently and completely changed his sexual orientation. Not only that, he was enjoying it. The more he let himself go, the more he was ashamed of himself. He may have grown up knowing and being taught that he liked girls, wanted to have relationships with them, sex… and now he couldn’t even grow erect for one. Now he was just another dirty little faggot, that couldn’t be denied. He knew she had done this to him, destroyed his heterosexuality and spoon fed him nothing but gayer and more humiliating and pathetic circumstances, and he liked it enough to milk himself until cum leaked out his cage while he got off on what he was, and probably still becoming.
After one of her many orgasms, she began the work of building Nicholas’ encounters for the next week. He was going to be in for quite a surprise next weekend.