I barely slept the night after the last session, not only was the chastity locked very tightly, I was so hurt and felt hopeless knowing that I would be a virgin for the rest of my life like Ella said.
After the 2nd day I called her to beg her to unlock me because the strain was on my mind the entire time, I was feeling discomfort 24/7. She didn't take any of my calls and sent them straight to voicemail.
I opted to texting because I realised that she wasn't going to take my call.
Me: Please can we set up an appointment at your office? You locked it too tight.
Ella: Locked what too tight?
Me: The cage...
Ella: What cage? Be specific ;)
Me: The chastity cage on my penis.
Ella: Oh you mean the cage on your small and pathetic shrimp dick? You knew the consequences of jerking off. You have to endure the pain.
Me: Nathan said that you'd go easy on me...
Ella: Oh wow, cashing in the chips you have with him already? Well you have to talk with him then, it's his promise to keep. As for now I am firm on you suffering pain until next week at least and probably a while longer after that. Permanent chastity is something that I'm studying and I think it's something your life is suited for.
Me: You can't be serious, please don't say that.
Ella: Let's not get ahead of ourselves, there is still much to dissect in your psychological state before you're ready for permanent chastity and forever sex free pussy free virgin life. I'll give you my boyfriends number and you can text him asking him for help so I ease up on your torture. This conversation is over. Don't text me about this anymore.
After she gave me his number I didn't respond. I felt that to a small degree I liked taking orders and that I was part of her plan, it made me feel as if I mattered to her a little.
Me:Hey Nathan it's me. Ella gave me your number so I could ask you for help. You promised me that you'd talk to her on taking it easy on me but she locked the cage very tight and I'm in pain. Can you please talk to her?
After two hours he responded
Nathan: I talked to her and you can come in her office tomorrow at 12. You owe me.
I hated the idea that "I owed him" but the pain was constant and too much to handle.
The next day I was at her office entrance sharp at 12. I knocked and Nathan opened the door making me worried but I had no choice. I entered the room where Ella was waiting on the love seat where we had our first session. She was fully dressed and gave zero slutty or sexual vibes. She had her glasses on and when I sat across from her she took out my key hanging on her necklace under her blouse.
"Today I will be a bit more off hands in my approach, it's going to be mainly between you two. I think you are ready for more homo erotic interaction." Ella started the session.
I looked a bit puzzled but knew that nothing good was going to happen. She would make me pay a steep price to loosen my lock.
"I'll offer you a deal, you do as I say and take part enthusiastically in todays session and I will unlock you, let you cum and lock you back with no strain, you will be comfortable." Ella made her offer.
"I'll do whatever you want." I instantly took her up on the offer.
"Good, then both of you take your clothes off to begin with" Ella say still and remained fully clothed while me and her man got naked. His cock was flaccid and not excited, mine was locked tight and swollen in its cage. The contrast was so immense as always.
Nathan sat next to Ella and spread his legs widely, I sat across from them waiting for what came next.
Ella handed me and her stud cards with questions written on them. "You will both ask questions back and forth and answer them truthfully, at the end you will get your reward as promised" Ella's hand went between her lovers legs and she started pumping him to life "You are only allowed to look at him or his cock, don't look away and don't look at me."
As two men with different sizes given to them sat naked with Ella stroking the more gifted one Nathan spoke up "I guess I'll ask first then, how did the last kiss taste from the last session? The one after I came on her face."
"It tasted like you, I could only taste your cum, I at least got to kiss her which means a lot to me." I focused on looking him in the eyes but so also want to look away due to shame but I couldn't look to Ella because of the rules, I knew that his cock was my only choice, I noticed how he wasn't hard yet as Ella was jerking him at a steady pace.
It was my turn to ask and I looked at the first card and read it "Do you see me as a man after our shared experiences together?"
"I don't, I think you're a sissy faggot." He said as Ella jerked him harder. I was starting to get used to insults like that so much so that it barely bothered me compared to how much it turned me on.
"I was informed that you didn't learn anything from the last session and you explained to her why you can't match up to me sexually, look at me and tell me why." Nathan slouched himself in the couch making his cock stick out as he was erect with Ella stroking him long.
I looked directly as his stiff cock and said "You're thicker, much thicker, your cock is so sexy, your balls are huge and it makes women excited when you slap them with your nuts while fucking, I've seen them react to it." I was aroused and rock hard inside my cage.
Watching Ella's hand glide on his dick I noticed it became wet, she poured lube making the handjob slippery. His cock was shiny and looked juicy.
"Go on, tell me more." Nathan Instructed me to praise him while a clothed woman was jerking him, two naked men talking about cock with a beautiful woman completely dressed listening intently.
"You're really long and stay hard, I feel really inadequate when you stay hard for an hour tearing her pussy apart while I cum in a few strokes. And I don't want to cum, I want to keep watching and jerking but I can't hold my load like you do." I explained.
"Do...do you like the way I suck your massive cock?" It took me a moment to wrap my mind around what she wanted me to ask out loud.
"I like it more when a woman does it but you've gotten better at it. In the future I want you to suck harder and lick my balls more. And also make sure to ask me if I like it and what else I want, pleasure me." He then turned to his girlfriend and said "Do you like how he's looking at my cock babe? He's such a faggot, I bet he wished that I was his gay boyfriend and fucked his mouth daily." Ella giggled and looked at me making sure I kept staring at the cock her hand was wrapped around.