And he pays for it.

Rachel and Jessica locked eyes as the pair contemplated the request that Deedee had placed on them. It was obvious that neither was entirely comfortable leaving the furious woman with Trent, yet they knew it was not really their place as well. Jessica’s eyes pleaded with Rachel’s. A slow breath in was all it took for Rachel to come to a decision. “We are sorry that the evening did not go as you wanted it ladies. Thank you for inviting us back to your house. We hope that the next time we are together it will work out better for all four of us.”

Jessica’s eyes darted between the two more dominant women in the room as she realized that this was going to be her exit. In a rare act of defiance she leaned in and whispered into Trent’s ear softly. “Being a girl is amazing babes. Stop fighting it, stop fighting her.” The sound of Rachel clearing her throat was enough for Jessica to slip away and stand up. The pair of women stood and looked down at Trent and Deedee as the two were still locked in the odd position with Trent’s head trapped between Deedee’s legs as she sat on the couch.

Taking hold of Jessica’s hand, Rachel led the pair towards the front door. As the pair stepped out into the evening air, Rachel turned back towards Deedee and spoke one more time. “If you need us for anything Deedee, Jessica and I will be at her house for the rest of the evening.” With those final words the door closed behind her and the sound of heels on concrete faded away.

Deedee’s eyes had never strayed from Trent’s made up face through the whole process. She hadn’t flinched even when Jessica leaned in and said whatever had been on her mind to the feminized boy. For his part, Trent’s eyes were cast down into the tangle of skin that was Deedee’s legs around his throat and the large round shape of his breast forms in the black dress. The tension in the air continued to grow as the silence stretched between them.

Deedee’s attention was purely focused on the feminine figure of her son in front of her. The past few hours had caused a bubble of frustration that felt like it was about to be relieved, only to have that chance snatched away from her at the last moment. She felt like she had tried everything to show Tiffany what life could be like. No, what it should be like. She had given her everything she could think of. Make out sessions with her dream girl, kept the men from her, even sent her shopping for whatever she wanted. She knew the lust in her mind was clouding her judgment, she even knew that she might regret this later, but it wouldn’t stop what was about to happen.

Her jaw set as she finally spoke up. “Tiffany, you are going to be a good girl for me. Otherwise everyone is going to find out just how bad of a girl you have been. Am I making myself clear?” Her tone was sharp and clipped as she spoke. It was clear that the love and tenderness of the past two days had finally been lost.

Trent nodded slowly without looking up. He knew that no matter what he couldn’t let those images get out. Yes, there were people that knew about this, but not many. It was up to him to keep the number as low as possible.

“That is not enough Tiffany. I want to hear you say it.” Deedee reached down and took his chin in her hands and pulled his eyes up to meet hers. “Tell me, or I video call Brittany and show her exactly what her little boyfriend is up to.”

Trent felt even more trapped than he had moments ago. Again, he was amazed at how swiftly Deedee’s emotions had done a 180 degree turn. Only minutes ago she had been loving, doting, even caring. Now she seemed calculated and hurtful. None of it made sense to him, but he felt like he had ****. His darkly painted lips opened and his jaw worked as he tried to say the words. No sound came out as his mind fumbled around exactly what she wanted him to say.

A sneer spread across Deedee’s face as she watched him. She was almost impressed by how he seemed willing to comply but was unable to do what she was demanding of him. “I see.” Unwinding her legs from around his neck, she placed one on either side. “Perhaps a demonstration?”

The next thing Trent heard was the dialing noise of her phone. Fear blossomed in his eyes and the wall that had blocked his words snapped open. The words tumbled from his mouth in that ridiculous accent that she was so fond of hearing from him. “Like, I’ll be a good girl for you Deedee.”

Deedee sucked at her teeth and shook her head. “Too late.” The hand that didn’t hold her phone reached down and pulled the tight white skirt of her dress up enough for her hard cock to pop up. Once again, Trent found himself face to face with her erection.

Fear and shock warred on his face as he heard the phone call finally being picked up. “Deedee? What’s up?” Brittany’s voice came through the speakerphone loud and clear. Other noises seemed to join as well. The loud thump of bass heavy music from another room, along with a voice that Trent couldn’t place.

“What does Double D want? Thought she and her little girlfriend were all busy.” The deep voice certainly didn’t belong to anyone that Trent could think of that Brittany or he spent time around. Deedee on the other hand seemed to know exactly who it was.

“Hey Brit, hey Jax honey. Hope you two are getting along. Say, Brittany, have you heard from Trent?” Deedee reached over and slipped her hand around the base of her cock. One leg slipped up around the back of Trent’s head and her perfectly smooth calf pulled him closer in, his face now pressing up against her groin. The length of her 7 inch cock rested along the side of his nose, her balls hanging just below his chin.

“Not lately. Why? Is everything ok?” Frustration seemed to war with fear as Brittany spoke up.

“Well, I wanted to talk about him with you. Everything is fine but…” Deedee nodded down towards he cock and Trent suddenly understood the message she was sending. He would need to please her now to make this call go away. Leaning back enough to give himself room. He tentatively reached up and took hold of her cock again. The sight of his long nailed hand wrapped around her girthy shaft seemed pornographic enough that it felt like he was watching a porno from the POV of the feminine star.

The deep voice spoke up again as the sound from Deedee’s voice fell away. “Why we gotta talk about this pussy again? Jessica told me that little bitch was mean as fuck to you Double D. And Brittany here all dressed up cute. Seems like this motherfucker ain’t worth the air he breathes.”

Brittany sighed and spoke up trying to defend her boyfriend. “Look Jax, Trent has a lot of stress right now.” All four of them could hear the lameness of the reply. Getting ready to stroke the cock in his hand, Trent froze as he realized who was on the other end of the line with his girlfriend. The tall black man who had hit on him yesterday while he had been learning to walk in heels appeared in his mind.

“Fuck that. None of that shit gives his ass the right to be transphobic. Not only that, but what kind of fucking pussy ignores his girl like this? Girl, you way too pretty to be treated like that.” Brittany’s giggle came through the phone clearly.

Deedee spoke up again. “He certainly has been finding the wrong way to use his mouth lately hasn’t he? No, see Brittany, I found something out about him. Some pictures on his phone looked like…” Trent knew he had to stop the conversation. Acting as quickly as he could he flopped his tongue out and began to lick the lock hard shaft in his hand. He could taste the moisturizer that Deedee used as he felt the hard yet soft feeling of the cock against his tongue.

“Looked like what Deedee?” Now Brittany’s voice was beginning to sound angry and annoyed. She had always been a bit worried that Trent would cheat on her. Trent could remember their conversations where she had been sure that she wasn’t good enough for him. Knowing it had been difficult to find a girl to actually date him, Trent had leaned into that belief and constantly told her about fictional interactions to make himself seem more popular with women.

Deedee smiled as Tiffany began to bathe her dick in long strokes with his tongue. “I don’t know Brittany. I guess, well, I’m just worried that he isn’t doing the right things. He really needs to make a decision. Either go at something all the way or give up and let it all happen. Does that make sense?” Trent’s eyes were locked onto Deedee’s as he struggled to understand the double meaning of her words. So focused on trying to understand what the words meant for him at that moment, he failed to think of what they meant for Brittany.

“Are you telling me that he is cheating on me?” The hurt in Brittany’s voice was palpable. “I can’t fucking believe that asshole!”

Deedee hurriedly spoke up as she felt Tiffany’s tongue continue to bathe her in spit. “Now now, I’m not sure honey. I think maybe I misunderstood. But I will say, you don’t seem surprised by the thought of him cheating on you.” Reaching her other hand down, she wove her fingers into the hair on Tiffany’s head and took a firm grip. “Maybe he is just unfocused and needs to really get to the point. You know? Take a big gulp of reality and swallow that down?”

Finally the double entendres that Deedee continued to use pierced the fear in his mind and Trent lapped his way to the top of the cock and opened his painted lips. Wrapping his mouth around the head of her cock, he let his tongue play along the slit. The taste of something salty began to appear as he realized that he had crossed a line that could never be uncrossed. He was now officially a cocksucker. A part of him wanted to bite down, to rebel against the **** that was being poured over him, but he knew that would only make it worse.

Chewing on her bottom lip to keep from moaning at the feeling of Tiffany’s darkly painted lips taking in her cockhead, Deedee was only barely listening to the response that Brittany gave as the girl began to speak again. “I don’t know Deedee, he just always seems to be so mad at me.”

Jax’s voice joined the conversation, his tone held a not inconsiderable amount of annoyance and anger that were clearly directed Trent’s way. “Look Britt, if this dude wants to ditch you, to treat you like shit then I say you forget about him. We can chill tonight and you can hang here with me.” Something clearly then happened between the tall dark skinned man and Brittany as she giggled and there was a moment of silence.

Finally, a breathless Brittany spoke up again. “Umm, I think Jax is right Deedee, I’m gonna stay here. If Trent wants to spend time with someone else, then I’ll do the same. If you see him, tell him to call me, but not tonight.”

Deedee finally grabbed enough control over her own mind as the pleasure continued to inundate her senses and addressed the words she had only barely understood. “Will do honey, don’t do anything I wouldn’t. Not that that is hard though, sounds like something else might be though.” With that, her thumb pressed down on the end call button and the phone was discarded off to the side as her second hand reached down and grabbed another handful of Tiffany’s woven in locks.

Meanwhile, Trent had done his best to zone out and forget the call that had happened above him. He knew Deedee was using the conversation to humiliate and threaten him, but the only thing he could do about it was follow along with her demands for now. So he focused on the horrible task in front of him. Only, as he began to really try and do better, he found that parts of him found pleasure in the act. While he had always hated going down on Brittany, this seemed totally different. Licking Brittany had always felt like a chore, something he didn’t understand. She would constantly be giving him pointers, telling him what to do. With this though, he knew exactly what a cock wanted to feel good.

It was simple to take the knowledge of what he liked and what he saw in porn and combine the two in an attempt to get this over with quickly. He knew better than to try shoving the whole thing down his gullet, so he used a hand at the base to create a block so that even if Deedee got controlling, he wouldn’t be **** to take the head into his throat. It also allowed him to jack her off a bit as each upward bob of his head brought his fist up as well.

For her part Deedee watched as he seemed to get into the blowjob. She had expected to have to be more forceful with the inexperienced fellator, but was pleasantly surprised when he began to apply skills that had taken her longer to learn. Her eyes rolled back in her head as the days of teasing by the stunning blonde combined with his skill at servicing her and she felt herself begin to contract up in what she felt was much too short of a time. While there was a part of her that wanted to cum all over his face, she knew that might be pushing it.

Tightening her grip, she pulled with all her **** and pushed her hips up, shoving as much of her cock as possible as deeply as possible into Tiffany’s mouth. The long wearing lipstick left dark rings around the cock to show just how deeply it had been taken before, this last shove pushing just past them enough that Trent gagged for the first time. The feeling of his gag and the sound of it was enough to push Deedee over the edge and her cock began to spurt into his mouth.

The first jet slammed into the back of his throat, the second followed it quickly. Realizing he had ****, especially if didn’t want to drown in the cum, Trent swallowed reflexively. The warm slimy liquid in his mouth fell down his throat as more and more kept pouring from the dick buried inside of him. Unable to fully contain all of it, some began to pour from the corners of his lips. With a final burst, the last shot almost dribbled out of Deedee’s spent cock as she released her son’s long blonde hair and collapsed back onto the sofa.

With nothing holding him in place, Trent collapsed back as well. Falling back from his kneeling position, he landed roughly on the hard floor. The sharp sting of the floor on his ass combined with the dull feeling of the plug pushing up inside of him brought a feeling of pleasure that he didn’t want. A thought crossed his mind briefly before he shoved it into the deepest hole in his psyche. The thought was a simple one, one of pleasure at a job well done. One of feeling proud that he had been able to make her cum so quickly and forcefully. Even as he shoved that thought down, another appeared.

Brittany had always complained about the taste of cum, saying the texture was even worse. Trent somehow found himself feeling the opposite way. There was something about it that he enjoyed. The feeling of that seemed so wrong to him, but it was an unshakeable sense. Closing his eyes, he sat there with Deedee’s deflating cock in front of him and simply tried to not think about what had just occurred.

Deedee’s bright eyes opened as she came to from the burst of bliss that a long overdue orgasm brought about. Her gaze took in Tiffany as the girl curled up into herself and seemed to try and shut out the world. Deedee could feel the post nut clarity beginning to set in. Thankfully, reacting to it was something that had been trained out of her by Chloe. In a sissy, post nut clarity was a dangerous thing, it led to bouts of regret and disobedience. It was the reason that most people caged girls like her. Chloe had opted for the harder task of training it out of her toy.

With the training in place, Deedee shut off the part of her mind that wanted to analyze what had just happened. Instead, she began to go about moving past it. Standing up, she reached down and pulled a shell shocked Tiffany up to his heeled feet. Trent’s almost catatonic state made it so that he followed her commands and actions without thinking. The rest of the evening was taken up by the pair showering and cleaning up. It was quiet without soft instructions from Deedee to Tiffany, Tiffany following along as she tried not to process what had happened. Falling down into bed, the completely exhausted pair fell asleep quickly.