I woke up a few times during the night. I felt Cass shift around once or twice, then in the middle of the night I felt Val pull her strap out of me and roll over. Other than that I had a good sleep. It felt incredible to have two beautiful women so close to me.

I woke up that monday morning to whispers. I couldn’t quite make them out. Just as I was trying to fall back asleep I feel Val’s strapon penetrate me. I immediately open my eyes and let out a moan. I see Cass staring at me.

“Good morning, my love. I had a fantastic sleep last night. We should do that again” Cass says to me softly. I look down and notice my cock is somehow still inside her. I can’t believe it didn’t slip out during the night.

“How did you sleep sandwiched between us? Any accidents?” Val says to me over my shoulder. She still has her strap up my butt.

“It was a bit rough, but I don’t think I did. Honestly the sleep was great besides a few interruptions”

“Let’s check” Cass says as she slides off of me. My dick is wet, but no come is on it. “Looks like you were a good boy”

“I had a dream about you last night.” Val whispers to me. “Cass was in it too”

“Do tell” Cass replies. She runs her hand gently around my stomach.

“Well I think you awoke a new side of me last night because I was fucking him in the ass and you were watching us. Actually you were kind of giving me pointers.” She laughs. “In the dream I was using a strapon, but I was getting pleasure from it too.”

“I come from my strapon all the time. Slave boy knows.” Cass pinches my butt. “If you want I can show you how”

Val smiles and I watch Cass lean over my body. She whispers in Val’s ear, but I can’t make it out. Val starts giggling.

“Oh you mean like this?” Val asks. I feel her start to slowly move the strapon inside me. The thrusts are very small and slowly. Her body starts grinding against my butt. I start to wiggle and realize my hands are still tied behind me.

“Yeah just like that. Do you feel anything?”

“I don’t know, a little?” Val replies

“Let’s roll him over and see if it’s easier from that angle.” Cass smacks my ass “come on roll over for us”

I do as I’m told. When Val was leaving with us yesterday I really thought she would be submissive to both of us. I did not expect to have yet another woman domming me.

“Perfect now start moving against him” Cass tells her.

I feel the strapon moving slowly again. Val moves her hips against my ass in a sensual motion. Its turning me on. I feel my hard cock moving against the soft sheets of the bed as she fucks me.

“Uh I think Im getting it” Val says as she lets out a moan. Her movements become more aggressive. I feel her strapon touch my prostate and moan loudly.

Val spanks my ass “that’s right, take my dick slut”. I give into her and she fucks me even harder.

“Mistress, can I come?” I yell out

“Absolutely not on my sheets.” Cass says as she stops Val.

“Turn him over. I’m not done” Val says as she pulls out of me.

“No, you’re done too Val. That’s enough for this morning.” Cass replies as she unbuckles the harness. I roll over on my back, cock throbbing in front of them. Precum drips from the tip.

“Please Mistress, I’ve been good, can I come?”

“No, you aren’t allowed” Cass slaps my cock. “Now I have to pee, Val do you want to come with?”

“Sure” Val replies. Cass picks up the panties from last night and puts them in my mouth.

“We’ll be right back. Be good please” she says to me as they walk away. I notice a big wet spot on the boxer briefs Val is wearing.

I calm down a bit and my dick gets soft. The ladies return and Cass starts going through her drawers.

“I had it in here somewhere. Oh yes here it is. You can grab his hands and I’ll put it on” Cass says in a matter of fact tone. I notice she has an icepack in her other hand.

“Okay come here slave boy.” Val grabs my shoulders and pulls me up off the bed “it’ll be easier if you just cooperate with us”

“Oh he knows the drill, he just doesn’t like it” Cass walks up to me with the chastity belt in one hand and an icepack in the other. Damnit I really have no way out of this. She presses the ice to my balls and my dick shrinks down.

“Wait, I have to pee first. Can we do it after that?”

Cass ignores me and slides it onto my cock. She closes the lock. “You can pee fine in the device. I’m sure Val would like to see it too” they both giggle.

“I’ve never seen male chastity in real life before. Kate keeps me in the belt all the time. The longest was a whole month.” Val says

“Well I think thats my plan for him this time. One month should start playing with his brain.” Cass laughs. I spit out the panties.

“Wait you can’t be serious. I can’t make it that long? That’s too long Cass” I start freaking out. Val bends over and looks me in the eyes.

“I thought the same thing the first time Kate did it to me, but as I told Cass in the bathroom, it really helped me reach a deeper level of submission.”

This was Val’s doing? Fuck, I never would have guessed her even meaner than Cass.

“Come on, you need to pee don’t you?” Cass says as she grabs my arm.

We enter the bathroom and I sit down reluctantly on the toilet. Both women stand over me.

“Don’t be shy” Val says.

I start to pee. It is the most humiliated I’ve felt since all this had began. I think back to how I got here and I can barely remember the normal life I had before Cass. This is my life now. I look up at the women watching me. For all the embarrassment, I still have no regrets. I love my new life.

I finish up and Cass flushes for me. I stand and Val pulls off the boxers, still wet from earlier.

“Here you can have your boxers back. I enjoyed them as you can see.” Val says as she hands them to me. I put them on and feel her wetness inside. It turns me on.

Cass and Val get dressed for the day. Cass decides to keep me in my underwear. We say our goodbyes to Val and Kate pulls up to give her a ride. She doesn’t say hi and drives off. Cass looks at me and smiles. This will be a long month.