Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 33 by RachelDaws RachelDaws

Who else wishes they could be in that room?

Not Trent

Deedee’s heels carried her into the house quickly, with Trent following along behind more slowly as he spent time thinking of what exactly he had seen and done on the car ride home. Walking into the living room, he looked up to see Deedee puttering around the living area as she straightened things like she would for any pair of visitors. The bulge pushing out against the front of her tight skirt that showed she was still feeling the enjoyment from his attentions in the car was the only that made her look anything other than a milf preparing for company.

Standing in the intersection of the hallway, Trent tried to understand his own feelings at the incredible events of the last few hours, let alone the last two days. He could feel his own desire like a stack of papers that kept having layers added to it. With the cage keeping him from being able to touch himself, there was no way to remove from the stack. This combined with all the new sensations was starting to overwhelm him. Closing his eyes, he stood there with his hands clasped in front of him and his feet together trying to find some way to think clearly.

A knock at the door interrupted his thoughts. He knew what he would see as they entered the door but there was something different about seeing the pair of women now that he knew what was between their legs. He stared at the group of three women as they stood near the door and chatted about something he couldn’t quite hear. It wasn’t that they were excluding him, just that he felt separate. Studying them, he looked for anything that would give away what he knew. Outside of the obvious bump in Deedee’s dress that she still hadn’t done anything about, he couldn’t spot a thing. He could see them grouped up, giggling and chatting like there was nothing odd about four people who used to be men all dressed up and parading around like they were doing.

That thought managed to snag his attention as it filtered through. He had just grouped himself up with them again. Sure, he looked like them, was dressed like them, even was caged like Jessica, but certainly he wasn’t like them. There was a tiny voice that he did his best to ignore that squeaked out that he could be like them if he wanted. His tongue flicked out between his dark painted lips as he stood there watching them. The voice he tried to quash managed to wyrm its way out of his grip and asked a different question. Why didn’t he want to be like them?

Fear spiked through the boy’s mind as he searched but found no answer to the question. He could feel the follow up questions building up behind the unanswerable one, the pressure exerting in his mind slamming up against the haze of lust that he seemed to exist under permanently. Trent’s breathing became shallow and increased in speed as his heart rate spiked. His mind railed at itself as he tried to establish that he was a man, that he had been born a man, he loved sex with women. He shouted the images and thoughts into the void and saw them fail to gain purchase. His sphincter gripped around the plug still held deep in him, the responding nerves in his brain firing off more pleasure spikes. He looked down at the outfit he had selected for himself and he felt the pride of looking good. It seemed like for every thought that tried to establish his manhood, there was somehow an opposite reaction that tried to establish his femininity.

“Tiffany dear, don’t be like that, come here honey.” Deedee’s voice called him over. While the war within him had been raging, the girls had settled onto the couches. Rachel and Jessica were sitting side by side on the large couch while Deedee was patting the seat next to her on the matching love seat. “Come sit. Jessica was just about to tell us the story about her dessert.”

Seeing the conflict in the boy’s face, Jessica grinned and leapt to her heels. “You were there, you have to come help me tell the story!” Running over she grabbed his hand and pulled him back towards the group. While Trent was certainly more steady on his heels than he had any right to be, he was still no match for Jessica. Dragging him along whether he wanted it or not, pulled him into the center of the room.

Trent looked around and saw Deedee and Rachel watching him. Both of the older women had reassuring smiles on their faces. Jessica’s own exuberance was infectious as always. “So like, there me and Tiffany were, making out.” Before he could react, Jessica pulled Trent up against her and shoved her tongue into his mouth. For the second time that day, Trent realized that Jessica somehow tasted different. The scene from the car ride back to the house flashed into his mind and he realized he must be tasting Rachel. Still, with the beautiful blonde’s hands all over him he didn’t push back from the kiss.

The pair of women seated at the couches cheered Tiffany and Jessica on as they made out. Jessica continued the teasing she had inflicted upon Tiffany at the restaurant, playing with her plug and her nipples sporadically. Trent was having a hard time catching his breath as they separated enough for Jessica to continue her story. He knew Jessica was saying something to the other two, but none of the words registered as he continued to kiss on her neck and rub his smooth legs against hers.

Jessica’s mouth returned to Tiffany’s as the pair began to lose themselves in each other again. With Trent’s eyes closed he focused on the feelings that Jessica was bringing to him. The embers of desire that had existed all weekend long were being flamed by finally getting to makeout with the woman of his dreams. Her hands seemed to be everywhere, one was cupping the soft mound of his ass, another toyed with his right breast, he could feel her fingers intertwining his as they held hands, he could feel her hand holding the back of his neck as they made out. Slowly, even through lust induced haze, he began to notice that he had counted far more than a single pair of hands. As he pulled back from the last kiss, he opened his eyes.

Pulling herself up against his back was Deedee, she leaned in and placed her own lips against his, her tongue slipping inside of him. A tiny portion of his brain fought at the pleasure that was being shoveled onto him. He knew they were manipulating him. A much larger part of his mind asked if that was such a bad thing. He had never felt pleasure like he had today. Had never felt desired like he had over the past forty-eight hours. Even with Deedee’s rod smashed in between the globes of his ass he groaned into his father’s feminized mouth as he began to crave each new sensation. Trent felt hands maneuvering him around to face Deedee as Jessica pressed up against his back. Without breaking their kiss, Deedee and Trent found themselves breast to breast and tongue to tongue.

From the couch Rachel’s smile was one of happiness. She loved watching Jessica work. There was something so pure in the woman’s love of sex. Something about her beautiful little slut that oozes sensuality, yet was innocent enough to drive a person’s desires to control her. It was a heady mix, one that she would never tire of watching go to work in the sexual corruption of those around her. Catching Jessica’s eye with a single crooked finger, she motioned for the blonde to come join her on the couch and leave the two together.

Jessica slowly disentangled herself and slunk over to kneel down at Rachel’s high heel clad feet. Leaning in, she kissed softly at her Mistresses soft legs and gazed up at Rachel with adoration. Looking down into Jessica’s eyes, Rachel felt a wolfish grin take over the happy smile that Jessica’s actions had borne. “Deedee, come sit with me.” Her voice had shifted, the raspy sensuality had shifted to something harder, more demanding.

Deedee’s ears perked up at the command that had been issued. A year’s worth of training had her slowly disengaging from her object of desire and making her way to the couch before she even realized that she had followed an order. “Tiffany, come sit with Jessica.” Deedee’s gaze took in the scene as Jessica kneeled at Rachel’s feet. She could see where this was headed, she could feel a part of her telling her that Tiffany wasn’t ready for this. A nagging part of her said that he never would be if she didn’t do something about it. The split second decision to trust Rachel saw her slipping down onto the couch next to the dominant blonde haired woman.

Trent stood in the center of the room lost. A moment ago he had been enjoying the feelings of Deedee as the pair of them embraced. He felt almost drunk on the pleasure that he was feeling. Before that it had been the pair of them. Two of the most beautiful women he had ever seen. Instead, now he stood lonely and confused as they surrounded someone new. “Tiffany, come sit with Jessica honey. Let her help you.”

Jumping at the chance to be a part of those sensations again, he stepped over towards them and dropped to the ground next to Jessica carefully. Confused at how he should join them, he watched for a moment. Jessica leaned forward and kissed her Mistress's legs again before taking her hands and pulling on them gently. Even in his muddled state, Trent could see that it was less of a demand that she part her knees and open up to Jessica and more of a request. As Rachel’s knees parted, Jessica motioned to the crossed smooth knees in front of him. “Copy me Tiffany babe. Like before.”

Trent could feel his mouth go dry as he realized what was happening. He looked up into Deedee’s eyes and saw the desire reflected back at him. Suddenly, Jessica was leaning in to whisper into his ear. “Just follow my lead. Let Tiffany take over.”

Trent paused and looked around the room. Closing his eyes, he drew resolve from somewhere deep within. “No.”

There was no hint of the valley girl. Even his posture shifted. Hearing the word, Rachel’s face hardened and she shook her head sadly. In contrast, Deedee went from cautiously happy, to angry almost instantly. She was tired of being rejected after trying so many different things. She wanted nothing more than to do this the nice way. Each time she tried, he did nothing but rebuff her. Tease her till she was so close to her objective and then stop. With each rejection it got harder and more painful for her to deal with. Jessica, seeing the shift in the two other women, leaned away and tried to distance herself from whatever was about to happen.

Deedee reached over and pulled her phone from the purse that sat next to her. As she searched through her phone she spoke up. “I tried Tiffany. I was lenient, I was nice.” She took a deep breath and let it out. “I was so proud of the way you took that plug up your ass. Of how nice our little makeout sessions have gone. But you just won’t go softly will you? You refuse to take part in this, even if you can see that it is the right thing for you. Fine, let’s do this the hard way.”

Turning her phone around she showed him the pictures she had taken of him that first night. Of him laying there wearing her panties, the cage clearly visible. Another of a cock laying across his cheek and him kissing along it. And finally, an image of the head of a cock buried between his lips as they sealed around it. With each image, Trent felt fear slip deeper and deeper inside of him. He could feel the lusty fog lifting slowly as he began to put two and two together. He had seen that cock before. He recognized Deedee’s bed. There could only have been one person that had done this to him.

Deedee watched as she saw him start to lean back from the phone in fear as the realizations set in. Not wanting him to run away from her, her right leg lashed out and wrapped around the back of his neck. Pulling him in, she braced his neck in a loose triangle formed of her smooth legs. To the side, Jessica’s eyes had gotten huge. She began to stand up only for Rachel’s hand to motion for her to stay. Rachel’s own face had taken on a look of respect as she watched the confrontation.

Trent’s tears began to streak down his face, his dark makeup following along the path down his cheeks. “Why? Dad, why?” He stared at the **** he knew would be used against him. He knew he didn’t have a way to fight against this, not with the situation he found himself in.

Fury took over Deedee’s visage as she glared down at her son’s pleading form. She had expected him to strike her, to try and pull himself free, but yet again he showed that he didn’t have the backbone to stand up for himself. He only had enough backbone not to do what she wanted him to do. Turning, she looked at Rachel and Jessica. “Ladies, I appreciate everything you have done today, but I think it might be time for you to leave. Trent and I need to talk…”

Trent done fucked up now...

Want to support CHYOA?
Disable your Ad Blocker! Thanks :)