How Far Will I Go

It was gross. Disgusting. How could he ask that of me?

Toeing the line months ago about it seemed to be enough to satisfy both our needs for that, but then today he says I'm going to just do it? As if.

There was zero chance in hell I was going to record myself doing that. Just because listening to him talk about it got me off during lunch, doesn't mean I need to bring this to the next level. He says it'll be fun though, at least for him it will be. For me? I can't imagine being anything other than shy and embarrassed.

And wet.

Okay so maybe it'll be a little fun. But not much, right? I'm not going to become one of those people that want to do this all the time, right? Surely, he has this idea of how it will go and reality won't live up to it.

How exciting can it possibly be for him to watch me pee? That's today's big question. He said I'll do it, because he asked. He's right. I will. There is even some suggestion I might thank him for letting me record myself and send it to him.

--20 min later--

Well. It happened.

I did it. And I thanked him.

Because at the end of the day, this isn't about the act of. It's about the control. It's about pushing personal boundaries and seeing how far I will go to please him. To obey him.

I guess we learned today... that that's pretty far.

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"The big game is on later!! Go Team!" I was so excited that we finally made it to the playoffs. This was going to be our year. Finally. I looked at him with a smile on my face full of hope and happy but nervous energy.

He just looked at me. Smirking. That was when I knew he had plans for me.

"Oh yes, Go Team....", he mock-cheered for my benefit. "But you know what would make this game fun?"

My eyebrows raised as I thought over his question. The answer was obvious. "What else could make it fun but some stiff competition and a win? Victory at last!"

He chuckled and went off to the bedroom and just left me standing there, wondering what he was about to do. He must have left his phone on the charger in there or something. I went to get my boots on so we could head over to his parents for the big game. I didn't want to be late.

He came striding into our foyer with heavy steps and reached out to stop me from putting my coat on. "Don't put that coat on yet. You're wearing something extra today", his voice sounded normal enough. I wondered if he had gotten me a new set of earrings for our team. He pulled out from behind his back my bra. This was no ordinary bra though, this was my uncomfortable one- the dreaded tack bra.

"You can't POSSIBLY want me wearing that today when we are at your parents'! It's going to be an all day thing! What if I need to take it off cause it hurts?! I don't want them seeing my boobs just hanging like that! You KNOW my nipples are always hard after that. No Sir, no." I stomped my foot and gave him a very unamused face.

Next thing I knew, he had pulled me down onto his lap on the bench near the door. "You know I would never put you in a situation that was too uncomfortable for you. Can't wear it all day? That's fine. I've got your sports bra in my pocket. I will always take care of you. I just want to have a little fun today. Don't even pretend you don't like a little pain with your pleasure. The game is going to be fantastic. Don't you want to feel even more aware during all of it? Soak in all the plays with your senses heightened? Baby..."

And that's when I remembered who he was. He wasn't some moron who just wanted to have kinky fun and not take responsibility afterwards. Or some inexperienced dom who didn't know that the bra will eventually get too much for me today. This was my sir. I trusted him so far, why not trust him again?

I nodded at him and stood. He pulled my jersey off and undid my front-clasp bra. The cold air fanned across my breasts and my nipples started to harden. Sighing, I took the tack bra from him and worked it on as gently as I possibly could with the tacks already starting to dig into my skin. It hit me then that there wasn't going to be a way to avoid the pain, so instead I leaned into it. Just like every time he had flogged me, spanked me, slapped my mouth... leaning into the pain made it so much better.

His left hand slipped into my leggings. The feel of his fingers pushing up into me made me squirm even more. The bra began to feel tighter as my nipples hardened, making the tacks dig further.

"There we are. You're all ready for the game now. At least, you feel ready to me." He grinned and stood up, grabbing my hand to lead me out to the car, and to what will be a Very Long Day.

———————————-

"But I neeeeeed to!! Please!!" I could not wait any longer. The teasing had been going on for days. The subtle hinting about how he wanted to make me beg for it. The voice notes while I was working, just him moaning for me and making me think about what he's doing without me.

He chuckled then let the smile sit there on his face. It morphed into one I knew well; he was going to give me only part of what I wanted. There would be no fucking today, but if I behaved there might be an orgasm for me. That smile was his worst smile when I was in this desperate state.

"Pick up the pen. Good. Now, I want you to fill your little hole with it." God, why does he have to make me Want to put a pen in my pussy. What an odd request, but coming from him it is somehow normal. I did what he asked, only flinching slightly as it bumped against my slick walls.

"That's sexy as hell. My good little toy filling her hole." He rubbed the top of my head in a way I couldn't tell if he was patronizing me or genuinely proud. I decided he was being sweet to me and leaned into his hand waiting for my next instruction. The need to cum was beginning to grow into something unbearable. She could feel the wetness start to slide down the pen.

"Now here's the really fun part. Don't even touch it." My eyes that I hadn't even realized I closed, suddenly shot open and a look of horror was painted across my face. Of course, this made him laugh. Resigning myself to his whims, I clenched around the pen to try and make this cruel and unusual not-a-punishment-but-still-mean task more fun and satisfying for myself.

"Just picture it sliding in and out. Fast and hard, just like my fingers, fucking you mercilessly", his voice became softer and I strained to listen to him. His voice had become my sole focus. "My fingers... fast, hard, grabbing inside you. Feel it. Feel my fingers like the pen, thrusting fast and hard. Feel yourself clenching around your little pen, pet? Good girl. Now, I want you to cum. Right now. Cum for me."

I let go. I clenched and imagined his fingers drilling into me, filling me. Hooking right up to my g-spot. The pen wasn't there in my mind's eye. I came. Hard. Drops falling to the floor in front of him. He watched me lose it over a freaking pen.

I sighed. There will be no living with him after this.