Room and Board Ch. 02.5.

And so they talked. Catching up jovially and lovingly for the first 20 minutes. Finally, Robb let spill a little of what had been going on.

"Wait...guys?" Anne's eyes widened in disbelief on Robb's phone screen.

"Yeah, it's just..."

"Robb, this is OK. We agreed on an open relationship. I just feel bad you hid this part of you."

"Well, I didn't know it was there until I tried..." Robb sheepishly responded.

She giggled, still wide-eyed. "That's so fucking hot. Do they suck you and stuff?"

"It's kinda...the other way around..."

"WHOA!!! Oh my!"

And so Robb explained it all from beginning to end, how the teens turned him, to Dr. Frederick, to what he did last night.

"Holy shit, baby! Look at you! I'm proud of you for exploring like this. BUT, I'm not really thrilled with them bossing you around and making you wear the...cage..or whatever...are you sure you're OK with all of this?"

"It's coming off soon...I wasn't at first...but I really like it now. I kind of like...the bossiness...I don't know" he replied, equally mortified and relieved that it was all coming out.

"Do you, you know...still love and want to be with me?" She said with a wry smile.

"What? Of course! I love you. This stuff....it's just...fun, I guess."

"Good. Then as far as I'm concerned nothing has changed between us." She smiled before adding "can I...see the thingy on your dick?"

Robb shimmied out of his pants, revealing panties and caged cock.

"Oooh, good taste" she cooed about his panties. "I honestly like the shaved smooth look. It's sexy" she giggled. "So, with that thing...can you still...cum?"

"I do sometimes...when they...you know..."

"OH wow...you need to send me vids like I do"

"I don't..."

"Cmon, after all I've sent you? Be fair. Do it now." Her face went from horny smile to controlling.

Robb sent her the video of him getting fucked by Dr. Frederick, explaining he made him say that stuff for effect.

"OH MY GOD!!! Look at you! Holy shit, Robby baby." She said, clearly playing with herself.

She watched the video in its entirety, eyes wide, and feeling herself up.

She grinned and spoke "let's fuck around. Do you have any toys you can use?"

"Yeah, baby"

"Get one and some lube. Lose your clothes." It was a blatant command and Robb obeyed.

Robb scrambled to comply and when he returned he saw Anne completely nude with her legs up on her desk. She looked so fucking hot. He wished he could be with her now.

"Position yourself just like me, baby"

He complied, lubing up his dildo as she slipped hers in. Soon, they were both fucking each other while maintaining eye contact and moaning in unison.

"OH yeah, baby. I miss you so much. I want to see you cum." She moaned.

Robb rammed his dildo in as he pinched his nipples. The fact he was doing this for his girlfriend added new dimensions to the humiliation kink he was on. He felt ready to bust.

She came first. He loved watching her legs tremble and her head fall back. It was so fucking hot.

He kept on in earnest but couldn't bring himself over the edge.

She smiled into the camera and said "come on baby, do it, I know you can."

From what he had told her and the fact that he was in a chastity cage, wearing panties, etc told Anne a lot about what would get her boyfriend off fast. She wanted to see it.

"FUCK your PUSSY for me, bitch. Get it all in there. Yeah, yeah, that's right. Keep going, BITCH!"

Robb blushed and moaned. He was unsure of this development. Was he doomed to be everyone's bitch? But the feeling in his pussy was too much. He would submit.

He started long dicking himself and felt it building. He involuntarily started moaning in his feminine voice, completely debasing himself in front of Anne.

"YES! YES! Keep going, babe! I can tell you're close! Cum! Fuck your sloppy slut ass!!!"

Robb came hard. Another threshold had been crossed. Anne smiled and clapped as continued to milk his prostate all while moaning like he was Riley Reid. He shoved it all the way in and fell back into his seat completely exhausted.

"Wow...i...wow..still can't believe it, babe. So...so..fucking hot. Going to have to change up some plans for when you visit. Please...bring all this with you. I want you just the way you are. No more hiding. I fucking love you."

Robb replied as much. He felt humiliated but very unburdened. It was a relief that she now knew and still wanted to be with him. Deep down, he was also appreciative that he essentially had a greenlight to continue on his path of being a femboy bitch. He was too far gone. He no longer wanted to stop.

Exiting out of the chat window, he eyed a new message from Dr. Frederick.

"Friendly reminder to be ready and outside waiting for me tonight. And I mean ready. Prelubed. Dressed in your best."

Robb sighed and moved the dildo in and out slowly. What could possibly be in store for him now?