Chapter Five: Question
[Warning: Heavy Themes of Mind Break and Non-Consent]
As Ian woke up again, it occurred to him that he had spent the last two days doing nothing except fucking and sleeping. That was probably by design. Better to keep them asleep when their master didn’t have them busy, no time for plans. Ian then realized he had changed clothes since passing out.
Ian groaned and put his face in his hands. Both him and Alex were wearing dark red silk night gowns with black lace, that went just passed their asses. Light from the window showed that it was a little passed sunrise now. It meant that there could be a whole host of new triggers that he and Alex had no way to prepare for.
There was a knock at the door, and Ian went over to look through the peep hole. Before he could, his hand automatically unlocked the door. It opened and Izzy walked in with a big smile. This time she was wearing yoga pants and a long sleeve sweatshirt. “Morning sleepy heads! It’s a bit chilly out there today so I suggest wearing coats when we go out. Luckily I brought some really cute ones for you” ian looked down at the suitcase she dragged in, and gasped in surprise.
There was a visible bulge at the crotch of Izzy’s pants.
What horrified him wasn’t it’s existence, but what it could mean for him and Alex. Ian took a step back. Izzy looked confused for a moment, looked down, and laughed. “Oh sweetie, it’s going to be so much fun watching master break you”
Alex was still on the bed as Izzy walked into the room. She placed the suitcase next to Alex and opened it up, revealing a wide variety of clothes. “This is my own stuff, so pick something you like and we’ll go shopping. Master gave me his card so we’ll be allowed to get you two cuties a full wardrobe.”
Ian decided now wasn’t the time for arguing. Alex must have thought differently. “What, so you’re our babysitter now?”
Izzy shrugged and sat at the desk. “Basically, but not for the reason you’re thinking. Master just wants me to get you two all prettied up before he gets here”
Ian looked through the clothes and used Alex’s confidence to bolster his”Oh? And what makes you think we’ll go with you? You can’t drag us there” It was dumb, almost goading her to try something. But if they were hypnotized while shopping, was it really them? Ian’s new worst case plan was to keep his real self intact by forcing their master to hypnotize him at every opportunity. He needed to share it with Alex later.
Izzy giggled. “Do you wanna be tranced so badly?” She raised a hand and snapped a finger
Ian’s dick immediately became erect, and he felt arousal building in him. The same happened to Alex. Ian chuckled “Master gave you some triggers then?”
Izzy shook her head “Maybe, but that wasn’t one. You two just love getting tranced so much that snapping makes you horny”
Both Ian and Alex blushed and went silent. It was a sobering realization how dependant their bodies were getting on this. Ian decided that the skinny jeans and tank top would be his best bet. He was actually surprised that anything like this was presented as an option. They had woken up clean even after the nights events, so Ian assumed they had been showered while under a trance.
“Oh those jeans come with this” Izzy said, hovering over his shoulder. Ian jumped back in surprise, and saw that she was holding a neon green thong I’m her right hand. “And the tank top comes with this” In her left hand she held a bra with bits just barely large enough to cover his nipples.
Ian grumbled and took the items, slipping the thong over his legs. Of course it fit perfectly, bringing doubt to izzy’s claim that this used to be hers. She kept have known their sizes. Ian threw off the night gown and tried to figure out how to put the small bra on.
Izzy giggled “let me help.” She slipped around behind him, pulling the bra tight on his chest and clasping it with ease. She spanked him suddenly, and Ian squeaked in surprise. A small wet spot had already formed at the tip of his erection.
Alex went with a blue sundress with white flowers on it. When he saw Ian’s raised eyebrow, he blushed and looked away. “Look man, clothes like these make it harder to be recognized.”
Ian wasnt sure about the logic there, but he didn’t argue. Once they were both dressed, Izzy pulled out a makeup bag from the suitcase. “Now Ian and Alex don’t have any experience with makeup, but Nia and Alexa do, so instead of teaching you guys, I’m just gonna save some time”
Before Ian could ask what she meant, the world skipped. Ian realized he was sitting in the passenger seat of his car, and Izzy was driving. Izzy laughed. “Sorry, I forgot to bring you two back. Nia and Alexa are just so much fun to talk with.”
Ian looked back at Alex, who was just as shaken by the sudden shift as him. Ian gasped. Alex was wearing a full face of makeup, and Ian could only assume he was doing the same. Red lips, black eye shadow, and eyelashes suspiciously long enough to be fake.
Ian leaned back in his seat and closed his eyes. “Where are we going first Izzy?”
Izzy stopped at a red light. “First clothes, then I want to visit your hairdresser, which is at the same mall.”
Ian wanted to put his face in his hands but couldn’t risk smearing the make up. What ever the embarrassment, it concealed his identity.
They arrived at the mall, and Izzy parked. She led them inside and through the shops, all the way to a very expensive looking store. The trip there Ian could feel the eyes of every man and woman on him. He cursed himself for wearing the skinny jeans. They hugged his ass tightly, and the thongs straps went over his hips, advertising exactly what type of underwear he was wearing.
Inside the store, Izzy began running around excitedly, throwing things into a cart. “You two go wait by the changing room” she said while eyeing a skirt “I’ll be over there in a sec”
Ian and Alex obliged. Once they got there, they immediately took advantage to speak without her supervision. Alex looked around to make sure she wasn’t near. “What should we do now? Izzy is going to be breathing down our necks.”
Ian thought for a moment. “Izzy will probably leave us alone tonight to be with Master on the computer right?”
Alex nodded “Most likely, unless he has something special planned”
“Either way” Ian whispered “We should buy a safe, one that opens on a timer”
Alex raised an eyebrow “Why?”
Ian held up his phone “We put these, your laptop, any cords to the desktop, and lock it for the night. It’s a longshot but maybe missing a night will help us get our minds back”
Alex was silent for a couples moments before speaking “Alright. We can have it delivered. We just need Izzy to be distracted long enough for us to buy it”
Ian looked around “Now might be the best-”
“Alright cuties, let’s get to it!” Izzy came around through the racks of clothes with a cart filled with items.
Ian swore under his breath. Izzy shoved a set of clothes into each of their arms, and pushed them into the changing rooms to try them on.
Reluctantly Ian did as he was told. Ian looked at the clothes and sighed. He held a set of black tights, a business skirt, as well as other items of clothing to give a feminine formal suit. What kind of places was Izzy expecting them to go?
Ian caught himself staring at his ass through the tights in the mirror. He shook his head. The master wouldn’t break him. He would find a way out, and fuck his girlfriend.
Ian’s eyes widened. He hadn’t texted Destinee a single time in the past couple days. Strangelt, she hadn’t texted him either.. If she got angry, she may show up at his dorm. Ian had no idea what Izzy and master would do.
Ian put it our of his mind for now. First, breaking the spell. He stepped our of the changing room, wearing the outfit. It had a black jacket, and a small back tie that hung loosely around the white button up shirt.
Izzy stared at him for a moment, hand on her chin. “Hmm, I don’t think that skirt is short enough. Ma’am!” Izzy called a worker over and spun Ian around.
Ian blushed as the female worker stared at him from behind. Izzy spoke while grabbing Ian’s legs “Im thinking we need one that goes just below here” Izzy grabbed just below his ass, and Ian had to hold in his gasp.
Izzy handed him a new set of clothes, and he went back inside the room. The next two hours followed a similar pattern of being showed off to the workers, with questions of tighter, looser, more skin, and other ways to further humiliate the two.
By the end of it, Ian was beginning to feel desperately horny. His balls ached, and his cock would not get soft. He hated how much he loved to be showed off like that.
Luckily, the humiliation had given then a chance. The amount of clothes Izzy had picked had her busy at the counter. Ian looked at Alex, who nodded. He ran off, and Ian waited with baited breath.
Ten minutes later, Alex returned. He gave Ian a thumbs up, and Ian sighed in relief. It was a small victory, but a victory none the less.
They left the store, and Ian couldn’t help but shiver as more eyes raked across his body. The experience in the store had only heightened his arousal, and awakened the exhibitionist in him. His erection pushed through his skinny jeans, and for a moment he wished he had worn a dress like Alex.
Izzy led them inside of the hairdressers shop. A very attractive middle aged woman greeted them. She hugged Izzy tightly to her chest “Hello my dear! Anthony finally let you take charge?”
Ian and Alex looked at eachother. So that was the name of the man tormenting them.
Izzy nodded through the hug and pulled away. “Yes ma’am. Now he wants these two to have some wigs ready”
Ian took a step back “Wigs?”
Izzy nodded “Yep. Until you hair gets long enough master wants you two to wear them.”
The woman giggled “Awe look at you Izzy, taking charge, I remember it like it was just yesterday, Anthony posting all those pictures of you embarrassed at his house”
Izzy blushed “As I was saying, can you get their wigs?”
The woman blew her a kiss and grabbed the wigs. Both matched the hair colors of Alex and Ian, and looked like they would reach below their shoulders. She put them into two bags and handed them to Izzy. “How’s the preparations on the new house?”
Izzy shrugged “I don’t know, I think Teela is I’m charge of that. But it should be ready for the house party on Saturday.”
The woman clapped her hands together “Sounds great! I’ll be sure to bring my boys and some treats with me”
Izzy nodded and waved goodbye as they left the store. Ian looked at her. “How many hypnotists live in this area?”
Izzy rubbed her chin. “More then you think. They keep linking up and moving near eachother. Common interests make good friends and all that”
———–
Back in the dorm, it was a long wait for the safe to arrive. Ian was nervous that it would arrive either too soon or too late. Too soon and Izzy would see it, too late and they would already be under. Luckily Izzy left to go deal with some other business, and the safe arrived not too long after.
Ian and Alex quickly put all of their technology in the safe, and set the timer for 8 the next morning. Ian laid down on the bed. “Thank God. Maybe this will be a step in the right direction”
Alex nodded, massaging his feet, sore from the heels he had to wear. “It better be, I have no idea what we’ll do otherwise”
The countdown to when master normally tranced them started. Each minute felt like an hour. Ian hoped there wasn’t any automatic triggers, but even if there was, there was no way to contact the master until the safe opened.
The clock struck 5, and Ian and Alex held their breath for a moment. Nothing happened. Then nothing happened for another five minutes. Ian smiled at Alex. “We’ve done it, we’ve-” Ian fell to his knees. His hips convulsed with the most intense arousal, and need for contact he had ever felt. Alex did the same, rolling on the bed, and holding his thighs as he thrusted into the air.
Ian grabbed at his own ass, desperately trying to use his fingers to satisfy its need to be filled. Nothing worked. Ian stood up quickly and ran to the bed, almost jumping on top of Alex. Ian pushed his ass against Alex’s thrusting hips, and Alex slammed his cock into him. It brought neither of them relief. No matter how fast Alex thrusted, or how hard Ian squeezed, it couldn’t satisfy the need.
They mawled eachother, licking and sucking anywhere they could. Ian had no idea how long they were like that, before the door opened and they looked up from their pile of desperation.
Izzy looked down at them, shaking her head. “You guys really aren’t that smart are you? You get hard at just a snap of the fingers, did you think you could go a night without a session.”
She pulled out two clipboards and two pens. “I have a way to help you, but first you need to sign this”
Ian and Alex took no time to read, they signed and kneeled expectantly at her feet, panting. Izzy giggled and placed a dildo in front of each of them. “Now this dildo is special sweeties. It’s been made to match that of a very special person. Our masters delicious cock. It should tide you over while I go punish someone for your mistake tonight.” Ian barely noticed the camera she was setting up directly in front of them.
Ian saw through the haze for a moment “Punish? Who?”
Izzy smirked down at him. “We were going to leave Destinee alone silly, but after this? It looks like Mr.Ferguson is gonna have a new toy”
Ian shook his head weakly, but his eyes never left the dildo “No, no goddamn it”
Izzy laughed as she left “You can stop me, you just have to get passed that toy there. HAVE FUUUN”
Ian stood up.
And immediately crouched over the dildo, hid ass swallowing it in one go.
Nirvana. Absolute ecstasy. Like the shirt before, it was only a taste of what their master would give them. Ian’s mouth was open in an O, and his tongue fell out. He started bouncing on it, giggling as his cock bounced up and down.
It was pointless. No matter how hard he fought, he always ended up back here. Feminine and horny, unable to fight the urges that were terrifyingly his own. Ian looked at the camera, still bouncing. How did he always forget? Why did he think he could fight once the pleasure ended?
Maybe he needed reminding. Ian put his hands behind his head, and smiled into the camera. “See Ian? This is us, a Stupid. Cock-loving. Toy” Ian slammed his ass down with every word. Ian descended into a series of humiliating actions. He pinched his own nipples. He slapped his ass. He pretended to suck a dick, two dicks. He did am ahegao face with two piece signs. Everything building up into a final orgasm, that sprayed up and over him, covering his face and chest.
Ian began licking it up off of his fingers, giggling as the camera continued to film.
*End of Chapter Five*
Source: reddit.com/r/eroticliterature/comments/s18bk9/drivein_blues_chapter_five_gayhypnosisfeminization