Ivan's Point of View
I lock the door with Stevie inside. God, she looks so fucking sexy naked with her arms bound to the bed. Tonight I will push her and find her limits. I will make up a game plan on training her once I am done learning her about her tonight.
I start walking to the office to register Stevie. I think of how hot it was to see Stevie react to me fingering her at dinner, then again with Grant in the hall. Grant and I have shared many women together. Stevie will be no different.
After registering Stevie as longtime guest of mine I race back to the room. It took longer than I expected. I unlock the door, and she is still there, naked, and bound. She looks annoyed.
"What the fuck?! You bind me then just leave me here? I want to leave. Uncuff me now." She demands.
I chuckle. "You will not speak to me that way. Do you not remember what happened a short time ago when you spoke to me like that at dinner?" I ask her. "Look around Dove, I have many instruments to punish you with here. Like that." I point at the bench. She gulps loudly. I walk over and unbind her wrists. I grab her face, "Stand up and bend over that bench." She stares at me, wide eyed. "Now." I leave no room for argument. She obliges.
I walk over to her. I bind her ankles first, then her wrists. I run my hand over her ass. I walk to the wall and grab a flogger. "You will receive 10 smacks for your outburst. You will respect me." I say. Smack. "Count them for me."
"One." She whimpers out. In the future, she will be louder with the counting. Smack. Smack.
"Two. Three." She whispers. I can hear her begin to cry. Smack. Smack. "Four. Five."
I run my hand over the reddening cheeks. I can feel her body reacting to the flogging. Smack. Smack. Smack.
"Seven. Eight."
Smack. Smack.
"Nine. Ten." She manages to get out. She is crying still.
She is so wet. I grab the aloe gel and rub it on her ass and upper thighs. I stick my fingers into her soaking pussy. She moans. I start moving my fingers around. I then starts moving them in and out slowly. She moans a little louder. "Tell me, have you ever had anal?" Looking at her ass like this. I want in there soon. I don't wait for an answer, I slowly move my fingers in that direction.
"No." She tells me. When I slowly insert just the tip of my middle finger she grunts. "Don't. I don't want to." She let's out in one breath.
"Trust me. You'll love it soon enough." I remove my finger. She audibly releases her breath. I smile inwardly, she thinks I'm stopping. I walk to the shelf. I grab the vibrator and the lube. I turn the vibrator and I insert it into her pussy. She moans quietly. I place lube in her ass and slowly enter two fingers. She tenses. "Relax, Dove. It'll be easier if you relax." I coax her. I move my fingers in circles. She doesn't relax. I play with the vibrator a bit to distract her from what I'm doing to her ass. She begins to moan to the vibrator, I take the opportunity to press my fingers in to the second knuckles. She tenses a bit more. I start thrusting them, and moving them in circles. I also move the vibrator once more. I move my fingers in more. "How does this feel Dove?" I ask her as I scissor my fingers.
"I...I-I don't know..." She moans out.
"Do you still hate it?" I ask as I begin to thrust my fingers in and out.
"I..." Stevie begins. I increase the speed. I remove the vibrator as well. "I..." She starts again.
"I need an answer Stevie. If I don't get one," I tell her as I add a third finger.
"It feel different." She cuts me off answering me. "I don't hate it." She continues.
"Good." I tell her. I remove my fingers. I walk over to the shelves an remove a purple and pink butt plug. And grab a condom from the night stand. I place the condom in my pocket. I walk back to Stevie. God she looks sexy as hell bent over the bench. I lube up the butt plug. I place the tip right at the entrance. "This will be bigger than my fingers. Do not tense up, all you'll have to do is stay relaxed and open. It will feel very good once it's in. I will reward you if you follow my directions." I tell her. I run my hands over her pink ass cheeks, my fingers run over her pussy lips, I can hear Stevies breath hitch. I take that opportunity to press the tip in.
"Ahh." I hear Stevie. "Please..." She starts.
I move the plug a little further in. "Please what?" I ask. I reach my free hand up and begin to play with her nipple. I kiss her on her hip.
"Please..." She says again. "Please...please stop." Stevie begs.
"Do you really want to stop?" I ask. I release her nipple and move the fingers to her pussy. She is more wet now. "Your body disagrees." I press my fingers inside her slick slit. She groans just a little. "Relax now my Dove." I demanded of her. I heard her release her breath once more. "Inhale now. Then, when I begin to push the plug in, exhale." I instruct.
Just as I told her to do, Stevie exhaled as I move the plug all the way in to the stopper. I move it around a little and she moans. I place my fingers into her slit, and she moans louder. "Very good, Dove. Now, for your reward." I tell her. I remove my fingers. I move around and remove the binds from her. "Stand up Dove." When she does I can see the conflict in her eyes. She doesn't want to like it, but her body does. I can also see the slight discomfort as her body is getting used to the foreign object. I guide her back to the bed. I place her face down on the bed.