Learning to Let Go is an 8 part continuous series; so if you were naughty and skipped ahead I urge you to start at the beginning or the following may make little sense.
Welcome to Part 8.
*****
2010
Jen's arsehole was tight, but not as much as I had expected, and the butt plug slowly slipped deeper and deeper inside her with relative ease until the last inch remained. I let her push it back out a little way before pressing forward up to the same point before she tensed up and my progress came to a halt.
"Are you ok Jennifer?" I asked softly.
"It's so big, Sir." I wished I had shown her its size before I started, but I didn't want to go backwards.
"You're doing very well. What a good little slut you are." Jen moaned softly and I felt her trying to push back to take more for me. "That's right, keep going; your arse looks so good being stretched like this."
"
Oh fuck... Sir... I can't... It's too big for me."
Shit, she only had a half inch left to go.
"Sir? Sir? It's hurting me."
Her panic was getting the better of her and I was sure I was right up against her limit. If she could just get this last little bit in...
With my other hand I slid my thumb between her pussy lips and found Jen's clit. She bucked instantly, and I gently started to caress it in the circular motion I knew she loved. The new sensation had completely distracted Jen from the plug in her arse; instead of pain, waves of pleasure washed over her. I had deliberately not touched her like this since the restaurant because I wanted this overwhelming effect later - although I had hoped to have her plugged first.
"Ohhhhhhfffuuuuuuck. Oh... fuck that's good!"
I didn't press any harder with the butt plug, I didn't want to distract Jen from the blissful feelings from her clit; but ever so slightly I relaxed the pressure my thumb had on her hard bud, dropping below a satisfactory threshold. Without realising she started to push back more, seeking pleasure, and I just braced my other hand as she started to impale herself on the plug. Slowly, by mere fractions she worked her hips backwards and I reduced the motion of my thumb so that she would wind her cunt against my hand; all the time accepting more of the plug.
"Let me cum, Sir!" She shouted at me and with a last effort I pushed the plug home.
"Holy fucking shit!"
She gasped. "It's
in
me.
It's in my arse.
" Jen was panting hard with understanding of what I had just done, and that I wasn't going to let her cum yet.
"Yes, Jennifer, your little bum is all full up. You've been such a wanton slut you didn't even figure it out. You must need to cum
very
badly?"
"Oh fuck" She whispered. "I was so close.
So close. So close.
"
"I know. How does the plug feel then, my little slut?"
"I feel so full, Sir."
"Do you like it Jennifer?"
"I
love
it Sir." My cock felt like it was going to tear through my jeans hearing her say that and I stood up and stroked it through the denim before pulling my phone from my back pocket. Quickly I clicked open the camera app and aimed it at Jen's raised arse. I actually took three pictures, but deleted the first two because the exposure was shit. I found that the act of working through this lighting difficulty, which would've been easy with a proper camera, calmed me down a little. I even stuck it through an editing app briefly just to bring the colours out. A quick visit into my settings and I turned off all the power saving options; selected the photo again - which would stay on the screen until I turned it off - and placed my phone against the box the restraints had come in so that it was blatantly in line with Jen's face.
"What do you think Jennifer?" She whimpered ever so slightly.
"I look like a slut Sir." I laughed and laughed at this.
"No, no; you
are
a slut, Jennifer. You think nice girls do this?" I pushed a finger into her cunt briefly and she cried out something that wasn't even a proper word. "If it looks like a slut, smells like a slut," I sniffed and then licked my fingers "and tastes like a slut.
Then it's a fucking slut, isn't it?
" I hissed.
"Yes Sir. Yes I am Sir.
I'm your slut Sir!
"
"Mmm that's very good. You understand now. There's two more items left in that bag though."
"Oh shit, oh shit, oh shit..."
She whispered over and over again.
"Do shut the fuck up will you,
please?
" I spat at her.
"Sorry! Sorry Sir! Oh fuck I'm..."
I put my head next to hers and yelled.
"SHUT. YOUR. NASTY. FUCKING. MOUTH. SLUT!" I slapped her pretty hard across the tops of her thighs, aware this would be equal pleasure and pain. She yelped but was silent after that except for her uncontrolled breathing. "Fucking hell but I can't even think with you going on and on; we've not even started your punishment yet..." Jen let out a tiny sound that was a cross between a squeak and a whimper. "That's right. I hadn't forgotten y'know? How long do you owe me Jennifer?"
"Forty minutes, Sir" She mumbled against the cushion.
"Sorry, how many?"
"
Forty minutes, Sir!"
Jen sobbed out loudly.
"Good memory." I said matter of factly. "Hey, why don't I get something out of the bag for you now?" Jen winced as I stepped over her. Picking up the bag I retrieved the penultimate item. "I have something I'd like you to wear. What do you think?" From my hand hung a black collar; there was little in the way of ornamentation, no studs or spikes, just four D-rings equally spaced around it.
"Oh God."
Was all she managed to whisper as I wrapped it around her petite neck, checking that it wasn't too tight, or her hair was tangled in it.
"Very nice Jennifer.
It really suits you
. Makes me want to fuck your throat while I hold it."
"Oh fuck... oh... fuck."
"But" I said "before we get to the fun stuff... I had better address the matters of your poor discipline." I met Jen's eyes and she looked genuinely terrified. "What in the world could that last thing in the box be?"
"I don't know, Sir."
"If you
knew
, it wouldn't be a fucking
guess
, would it you daft slut?
Guess
."
"Sir! I don't know, I don't fucking know, I don't..."
I smacked her arse so hard I could see the exact outline of all my fingers and Jen howled with pain.
"FUCKING GUESS!!"
"It's a whip. A fucking whip. Something to whip my arse with. Oh fucking hell Sir, please don't hurt me!"
I knelt down beside her and stroked her hair which made her try to flinch away but she couldn't easily move.
"Don't be ridiculous, Jennifer. As if I'd do that to you? Point of fact I'm not really good enough with a whip yet..." I tried to be as soothing as I could and Jen responded well by calming down a little. "You've got yourself all worked up over nothing, silly girl. It's just a sex toy that's all." Jen looked relieved, but said.
"Will it hurt me Sir? Is it big?" As I was there I decided to rub one of her nipples a little and she moaned loudly.
"No, no monstrous sized dildos or anything. It doesn't even go inside you Jennifer." She looked up at me confused.
"It doesn't?"
"Don't worry little slut, I'll make sure you're well and truly satisfied. Let's get it out hey?" Jumping up I picked up the box and the bag just fell away so that Jen could see the picture on the front.
"It's... it's a
microphone?
" I laughed.
"No, silly girl! This is a wand. It vibrates."
"On the outside?"
"
Oh yes."
I stripped the packaging from it with gusto; I'd used Hitachi wands lots of times before - had been on the receiving end of them too - and while they really looked very innocent I knew they were anything but. I placed it next to Jen's head and I could see her looking at it quizzically. "Hang on; they never give you a fucking long enough cord."
Jen had no choice but to wait and try to work out what was going to happen next. I hadn't done this intentionally - it was another fuck up that I hadn't had an extension lead ready, although I had a couple spare for DIY in the kitchen so it didn't matter. When I came back I was treated to the awesome sight of Jen's plugged arse pointing up in the air, and her cunt was leaking down both her thighs. My cock thumped hard, and I felt that knot in my stomach pull tighter.
Not yet
I told myself.
Once I had plugged the wand in and tested it on my arm I helped Jen open her legs. She couldn't do this by herself what with her wrists cuffed to her ankles, so I had to lift her by one of her shins at a time until her legs were wide open. I could tell as she moved the butt plug stimulated the inside of her arse by her little moans.
"That's
so
much better, isn't it?" I said.
I could fuck her so easily like this
I thought, but instead grabbed my phone and selected the timer function and entered the forty minutes she had earned herself. "So... are you ready?"
"Please tell me what this will do Sir?
Please?
"
"Hmm, ok fair enough." I caressed her beautiful back and hips while I made myself comfortable behind her. "Throughout the day I've been teasing you. There was that moment at the library, another at the restaurant, and finally again just now, when I touched that naughty cunt of yours." I tugged on the handle of the butt plug and Jen let out a long sigh. "But... you are quite ready, I suspect, to cum. Is that a correct assumption?"
"Yes Sir." Jen whispered back "I
need
to cum so bad, Sir."
"Well, had you been a well-behaved slut I'd have fucked you 'til you came all over me." She moaned even at the idea of it. "Unfortunately, because you're such a useless cunt, I now have to teach you a lesson."
"Please Sir, just fuck me?"
