Learning to Let Go Pt. 08

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?"

"Shut, Up. You've ruined my enjoyment also. I've got to spend forty minutes doing this now when I could've been fucking you instead. Don't think this isn't hard for me too you naughty little girl." I pushed a finger into her pussy and she shuddered. "I could have my cock in here already if you hadn't been such a bad girl. So, you managed to knock up forty minutes. For forty minutes I'm going to use this want to stimulate your clit. I'll tell you now; you're going to love it, but... I'm not going to let you cum."

"What? How?"

"Every time you get close I'm going to pull away Jennifer."

"Oh my God..."

"Ready slut?"

"Don't do this... Sir... oh fuck..." I hit the on button and put the wand at a low setting and paused to clear my thoughts. This always got intense and I wondered if I could do it or if she'd turn me on to the point I'd end up fucking her senseless. I reached over and hit the start button on my phone and the numbers instantly started dropping.

I placed the big white dome directly onto Jen's clit.

It was like she'd been electrocuted.

"Ohmygodohmygod... HOW IS IT DOING THAAAAAT?" Jen was screaming, literally screaming, and her hips bucked and thrashed. "Fucking hell. Fucking hell. Fucking hell. OH GOD I'M..." But she didn't cum because I removed the toy from her body.

"That didn't last long Jennifer. Only three minutes." I reached over and stopped the clock

"Wha - what are you doing?" She didn't call me "Sir" but it didn't matter, she was going to forget all of that soon anyway.

"Sorry?"

"You stopped the timer?"

"Oh I see... Sorry, but the time when you're calming down doesn't count towards your forty minutes - thirty-seven now."

"You fucker." I put the wand back on her skin but this time kept it away from her clit and let it vibrate against her cunt hole sending pulses through her body. The Hitachi easily had enough power that the sensations would reach her clit but nowhere near as strongly. "Oh... Ohhhhhhhhh, yes... yes..." Jen's eyes fluttered half open as she cooed softly. With my other hand I gently pumped the base of the butt plug in her arse. "Oh god but that's good..." I let the numbers count down a couple of minutes before shifting the wand's head closer to Jen's clit. "Jesus... Shit... that's... that's fucking amazing."

I smiled to myself and let her have some time to really build her orgasm. She must know what'll happen I thought, but then remembered back to my own experiences and how logical thought seemed to go out the window. My hand slipped down a little further and again the wands powerful head rested against Jen's clit.

"Don't take it away! Don't! Please! I need to..." Of course, I let the wand fall away and paused the timer. "Fuck! FUCK! FUCKING LET ME CUM!" I couldn't help laughing.

"Listen you slut, you've still got a whole half an hour before you can cum."

"I... I... can't do it... I can't fucking DO it!"

"Ok then." I stood up. "I'm going to get a drink."

"What the fuck?"

"Let me know when you want to cum little slut." I could see the terror in her face as she realised she had to go through this if she wanted to cum at all.

"Wait... Sir... Oh fuck... wait Sir!" I spun on my heel and snatched up the wand and flicked it to a higher setting and then jammed it into her cunt. Her whole body shook.

"Don't ever fucking piss me about again you stupid bitch!" I snarled at her.

"I'm sorry... aaaaargh I'm fucking so sorry Sir!" I pulled the wand off her and her body, which had been bow-string taut, and she sunk down onto the floor, her chest heaving. "Holy shit... Holy fucking shit..." Switching the vibrator down again I set it to a deep pulse and pushed it right up under the butt plug and hit the timer.

Jen let go of a low growl, and pushed her arse back against it wanting more, so I knocked up the intensity a notch. "Huggghhh god yes." She was trying to use the head of the want to push the plug in, so I reached up and gently started to pull on it. "oh fuck, oh, oh fuck..." It popped out of her tight sphincter "Aaaaauuuuuuwwwww... Put it back in me Sir... Please!"

Scooping some lube from around her arse I pushed a large globule of it down her slightly dilated hole and pressed the rubber spike back inside her. "Aaah! Fuck yes!" I loved how her hips thrust back, wanting it. I pulled again, it came out easier this time but she still moaned "No Sir... no... a slut like me needs it... I... fucking need it!" I spent a little time teasing her with it; not quite pushing it in all the way and letting her try and push her arse back further, my hands not offering the resistance to force it inside her.

"You need to push much harder little slut." I whispered, completely enthralled with her movements. "Go on, try and fuck it you filthy bitch." She started to buck as hard as I have ever seen anyone trussed like that move. It was fucking extraordinary - her core muscles lifting her entire upper body up and her thighs driving her arse back onto the plug. All the time grunting;

"Want it... want it... Want ...it" I stopped playing around and let her take the rubber into herself while simultaneously pushing the wand back onto her clit. "AAAAAAAAAAGGHHHHH FUUUUUUUUCK..." It only took twenty to thirty seconds before I had to take it away before she came. "You cunt... YOU FUCKING CUNT!" She shouted. I just reached over and hit the stop button on the phone.

"You're doing so well Jennifer. Wow but you're really impressing me."

"Fuck off." She spat. I laughed and put the wand up to her mouth.

"Lick it slut."

"No."

"Oh dear... now that's very naughty." Jen's eyes widened in panic.

"Shit. No! I'm sorry, I'm sorry, I'm really fucking sorry!"

"Bit late to be sorry young lady. Christ... I don't know how to make this better. And I was going easy on you too..."

"Sir! Sir! I'll do anything" FUCKING ANYTHING! Just don't... not more of this... pleases!"

"Gotta be honest; I was thinking about resetting the clock..." Jen started sobbing.

"Fuck no... please... No...anything... anything."

"I thought girls liked a lot of attention though... Don't you like a bit of foreplay Jennifer?"

"No... no... no... no... no..."

"God and look; you got down to twelve minutes there. I can't believe we have to start all over again." She was just mumbling into the cushion and I noticed it was covered in saliva that had run out of mouth with her unable to do anything about it. "Look... tell you what" I said standing up straight "what about if you do something nice for me, and maybe I'll let you off ok?"

"Yes Sir, yes Sir! Undo me and I'll do anything you want to you. Tell me and I'll do it!" I shook my head remembering how I had told Nikki a very similar thing years ago. Fuck I was innocent then.

"Sorry but you're staying there. You've still got twelve minutes - I'm not letting you off those." Her face dropped "But I promise I won't add on any more." I pulled my t-shirt over my head and dropped my jeans and shorts. It felt fucking fantastic to finally release my cock and I stroked it in front of Jen. "There's no reason why I can't cum, I'm not the naughty one around here." She eyed my cock, watching my hand move slowly up and down.

"Are you going to fuck me now Sir?"

"Absolutely not. You'd cum straight away - I'm not a fucking idiot Jennifer."

"Then..."

"Then I'm going to fuck my slut's pretty little mouth."

"Oh God..." I positioned myself next to her face and lifted her upper body by her collar until her mouth was lined up with my shaft. She was being partially choked like this, which was the point, and although I could see fear apparent in her expression she was already trying to get the head of it in her mouth.

"Good girl" I said changing my grip to support her more and guided her head on to me. Fuck... this was amazing and also, I was already so close to my own orgasm... it wasn't going to take me much and I didn't intend to hold back at all. Jen was trying to force her mouth on me harder and harder, but she was sideways on to me and it wasn't really working - again, it didn't matter, I just enjoyed watching her body strain to please me. "That's right Jennifer; fuck you are a nasty bitch aren't you?"

She looked up at me then and, I don't know, it was like she really was a different person. She'd changed. Her expression was... not... assertive? I knew then, inside her head she'd submitted, she'd gone through it all and had finally just... let go. I breathed a little easier then because I really did think I had gone too far a couple of times but no, she accepted it all and now just wanted to please me by being whatever I wanted; and right now I wanted a slut, and so, she was. Her head bobbed back and forth frantically trying to make me cum and I was so damn close it wouldn't take too much more. I grabbed her head with both hands.

"You're going to take this like the slut you are." I growled at her and started to fuck Jen's face. She squeezed her eyes shut and sucked on my cock as hard as she could while I thrust myself into her as far as I dared. Jen had never managed to deep throat a guy and I didn't try to make her now, but I did push right up to the back of her mouth making her gag and gasp. "Yeah, you filthy bitch... fucking... fucking take it!" The strain in my body beginning to collect at the base of my dick and I felt the tell-tale yearning for relief drive my hips forward, "Yes, yesss, YESSSSSS!" I pull Jen's face against my stomach and pumped wads of cum into her mouth. She could barely breathe let alone swallow and cum leaked out down her chin. I pulled out and wiped my spunk covered dick all over her face as she gasped, choking slightly. "That was very fucking good." I said exhaling. Jen didn't say anything as I placed her head back on the cushion. She was a real filthy fucking mess now. "You didn't like that Jennifer?" I asked.