Teaching Demi Ch. 01

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Dan teaches his staff a lesson she won't forget anytime soon.
4.9k words
4.27
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Part 1 of the 3 part series

Updated 06/10/2023
Created 02/26/2021
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Demi!!

Where the fuck is that girl again???

*****

I run a small boutique in London, and just like most independent business owners I can afford to hire only one member of staff at a time. When my previous employee retired, I was gutted as not only was she an amazing worker, she was also very good with men who would literally buy anything she suggested.

When I hired Demi to replace her, I was a bit unsure as she was only eighteen and fresh out of high school with no solid work experience. However, she dressed impressively and spoke politely at the interview, and against my better judgment I decided to offer her the job.

Fast forward a month and I was at a point I was going to kill her! What could she be doing upstairs again??

From the first week of her employment, I started noticing she would disappear upstairs where the toilets and staff room are for at least ten minutes at a time. By the second week I was convinced she either had IBS or was on the phone. What was really annoying was she would wait until I was occupied with a customer before running upstairs. This left me in a very vulnerable position because if another customer walked in at the same time, I was left trying to juggle two customers at the same time.

I sat her down and explained to her a number of times why I need her downstairs with me when I am with a customer, however it felt like it was falling on deaf ears as she kept on making the same mistake. She knew very well that I wouldn't come upstairs after her when the front door to the shop was open, and I was starting to hate the fact she was taking advantage of this situation.

Unbeknown to her, last week I had a CCTV camera installed upstairs.

This particular day I had had enough! The customer I had been with for nearly twenty minutes suddenly decided she had to bring her husband in for a "second opinion", and as I struggled to do my best not to look disappointed, I noticed another customer who had been patiently waiting to be served walking out too. So instead of having two potential sales I had lost both, and this tipped me over the boiling point.

As soon as my customer walked out, I checked my phone to look at the camera and sure enough Demi was quietly sitting on a chair playing with her phone. I quickly locked the front door, closed the shop, and decided to finally confront her.

"What the fuck are you doing upstairs Demi?" I screamed at her as soon as I walked upstairs. She did not expect me there and simply yelped and tried hiding her phone behind her back.

"I'm busting my balls downstairs and you are sitting here on your arse playing with your phone? Are you fucking kidding me?" I spat out as I glared at her.

"No, it's not like that Dan, I had an upset tummy so I was in the toilet all this time, and I just came out now to quickly check my phone before I come down to help you," she stammered as she looked at me fearfully.

"I was not born yesterday and I have given you enough warnings. Pack your stuff and get out. I never want to see you again." I noticed her whole body was shaking like a leaf.

"No please give me another chance. My mum would kill me if she knew I lost this job. I've already promised her rent money for the next six months." She was tearing up as she realised how badly she had screwed up.

"I don't give a damn what your mother thinks Demi. In fact, I am not even going to pay you for this month. Off you go." I am usually never this cruel, but this girl was bringing the worst out of me.

"What??? No, you can't do that, I have worked for a month. You owe me my salary," she was almost hysterical by now.

"Listen you little bitch, you fucked up. I haven't given you a contract as yet and taking into fact you haven't done a single sale this month I have no reason to pay you. Now get out so I can actually employ someone capable of helping me.

"No, no please Dan. Don't do this, I always thought you were a great guy and I know I screwed up. But please don't sack me. I'll do anything for you to give me another chance." The tears were flowing freely now as she started begging me.

I took a deep breath to calm myself down and assessed the situation. I suddenly realised I wasn't angry anymore, but watching Demi cry in front of me was in fact starting to arouse me.

I looked at her intently. At around five foot five and probably just over 120 pounds, with all the right areas filled up nicely, her body looked like it was built for sex. Her brunette hair was put up in a ponytail and her brown eyes that were full of tears at present, were usually playful. For eighteen years old she definitely knew how to dress up to look mature. The grey sleeveless dress she was wearing came all the way to her kneecap, and if I had seen her in the streets, I would have probably mistaken her for a secretary or a school teacher.

"Ok let's talk about this, what do you mean anything?" I asked her as I walked towards her. My tone not as harsh as before.

"I do mean anything. I will work double hard and not even take lunch. Please just don't fire me."

"I don't mean your work. You said you'll do anything for me. Did you mean that?"She swallowed hard as I moved very close to her as my eyes ran over her body before looking straight into her eyes.

Suddenly she realised what I was trying to imply, and she looked at me in shock.

"I am not going to sleep with you for my job!" She yelled as she took a step back almost looking horrified.

"I thought you said anything Demi,".

"I can't do that Dan. I have a boyfriend and I love him very much. Please try to understand." She was openly sobbing now.

I should have felt sorry for her, but her vulnerable state was simply turning me on. So instead of threatening her I decided to reason with her.

"Listen to me Demi. It's just not working here for you. You should have thought about how important this job is to you before you started sitting upstairs on the fucking toilet or spending time texting your friends. I have given you several warnings!"

"Yes, I know and now that I think about it, I do realise how badly I messed up, but please Dan, give me one more chance."

"I'm sorry but I can't think of you as staff anymore. When you said you will do anything, it made me realise how attractive you actually are, and the only way you are going to keep this job is by doing more than your job role."

"No please Dan. Don't make me do this. I have only been with my boyfriend and I want to marry him."

"I am not making you do anything Demi, and your boyfriend is not my problem. You'll just have to explain to your mother why you can't pay your rent when you get home. Now leave please."

I took a step back and sat on the chair as I enjoyed her dilemma.

"Please no I can't do that Dan, she will kill me... If I say yes, it will be a onetime thing, right?"

I watched her intently as I thought about how best to approach this situation.

I didn't simply want to fuck her but instead I wanted to own her body and do everything I wanted to do with it. The last time I had an eighteen-year-old was back at college and just thinking of that tight pussy and arse was turning me on tremendously.

"I can't make any promises Demi, but we can see about that." I was not going to let her off the hook that easy.

"Ok, I really will do anything you want, I really mean it. Anything! I have to have this job." It sounded like she was almost talking to herself more than to me.

"Ok, tell you what, I'll give you one last chance. From now on your "upstairs duties" are going to be different. You are going to do everything I say without a single word of complaint. If at any point you refuse to do what I say or complain in any way I am throwing you out and nothing you say will ever make me change my mind. Is that clear?"

She looked at me through those big brown eyes and nodded slowly almost in defeat.

"Now, come over here and hold onto the table and bend down," I instructed as I watched her intently.

She let out a sob before she slowly went towards the table and bent over with her arse sticking up and her boobs resting on the tabletop. The scene from the movie "The Secretary" came to my mind as I walked behind her and admired her shapely arse from behind.

"That's very good Demi," I told her as I admired her peachy bottom that was sticking out beautifully.

"Now be a good girl and straighten both your hands and hold on to the table edge. I do not want your hands to move unless I tell you to please," I instructed her and waited until she followed my instructions.

Once satisfied with her position, I reached out and ran my hands over her back before resting them on her plump arse cheeks. A gasp escaped her lips, and I could see her legs were starting to tremble.

"What a hot sexy bottom you have," I told her truthfully as my hands cupped her cheeks and kneaded them firmly. With both my hands firmly holding on to her bottom I leaned down and gave it a quick kiss.

Demi let out an airy moan as I took time moving my lips all over her arse. My cock began to grow rapidly as my eyes and lips feasted on her ample backside. Unable to wait any longer, I stood up and pressed myself on her.

I heard a whimper escape her throat as I positioned my painfully erect cock right at the middle of her arse crack and slowly dry humped her. Via my actions I was daring her to disobey me and either move her hands or say something, but instead she remained quiet and let me have my way. In-fact I suspected she was starting to get turned on as my hard-on pushed itself deep between her plump arse cheeks.

Realising she was actually going to let me do everything to her young body, I had to control my excitement, as I pulled away from her and knelt down behind her and ran my hands over her naked calves. As I pushed her dress up all the way over her arse, her flawless juicy arse cheeks came to view. I nearly growled in excitement as I admired the very thin strip of silky pink fabric that was resting between her plump cheeks.

I took hold of her thong panties by the sides and pulled them down her legs and ordered her to step out of them. I held the tiny garment on to my nose and smelled her, pressing the part that would have been on her pussy and arsehole right under my nose. It was definitely a lot muskier and earthier than what I expected, but this just aroused me further.

I quickly pulled up a chair behind her naked bottom and sat down, bringing my face down to the same level as her arse.

"Your panties smell wonderful Demi, but let's see how you actually smell." Her breath quickened and she let out a gasp as I grabbed hold of her buttocks firmly and pried them open.

"Oh no," for the first time she spoke as my hands pried her arse cheeks open and I stared at her tight brown pucker hole.

"Remember, no resistance, and no complaints."

That quickly shut her up and I went back to admiring her tiny rose bud. She had done her best to shave around her holes and I wondered if her boyfriend did any of the things that I wanted to do to them. I put my legs in-between hers and nudged them apart. She yielded to me and she parted her legs allowing me better access to both her private holes. Her winking brown hole looked ridiculously pretty and tight while her juicy pussy lips were plump and moist. As soon as I saw the wetness around her pussy, I knew she was enjoying this probably just as much as I was.

I've always been an arse man and the fact I haven't had a new arse in a while was making this whole episode a lot more exciting for me. With both my hands firmly on her plump cheeks I spread them as wide as I could before bringing my face towards her nether region. After a very close inspection of her bottom, I stuck my tongue out and found the entrance of her pussy.

"Urgh!!" An animalistic moan escaped Demi's lips as my tongue explored her lovehole teasing and tasting her excitement. Not just stopping there, my tongue traced its way from her pussy to her perineum and firmly rested on the entrance of her tight arse hole.

"Oh, that feels strange," she said with gritted teeth as I used my thumbs to open up her arsehole a bit more and placed my nose there inhaling her musky scent. The earthy smell filled with her pheromones was proving to be a big turn on as I felt my cock threatening to explode without me touching it.

"God I am loving tasting you and smelling you Demi," I told her as I continued prying her arsehole open with my fingers and pushed my nose deeper in to her bowels. The intimate smell of this young girl was sending me into sexual overdrive.

"Has anyone ever done this to you before?" I asked her as my nose was deeply inside her bunghole.

"Oh God no. No one's ever touched me there!" She moaned with her face firmly looking away from me.

"Good I am going to show you what true pleasure is," I told her as I stuck my tongue out and gave her arsehole a long lick before pushing my tongue as deep as possible into her anus.

"Oh God!! Ewww!! No!!" she yelped and feebly tried to push her arse out as she felt my wet tongue poking her anus.

"Quiet. Remember your promise."

Although I badly wanted to taste her backdoor, I could feel Demi was still not sure about the anal invasion so I quietly went back to her pussy and started eating her out.

"Oh yeah." Not only did that loosen her up quickly, there was less complaint as my tongue occasionally wondered back on to her arsehole.

"Your body is driving me crazy Demi," I whispered as I unbuckled by trousers and freed my painfully erect cock. I quietly started jerking off as I continued eating both her holes out.

"Oh God, this is so disgusting," she moaned with gritted teeth as she felt my tongue forcefully open her arsehole and slipped a couple of inches inside her. However, her body contradicted her words as she pushed her arse back at me, and I gladly responded by opening up her arsehole even further and slipping my tongue as far as possible.

"You can pretend to hate it but your pussy is saying otherwise," I informed her as I pushed my thumb into her soaking wet pussy.

She yelped at the sudden intrusion, but I ignored her and buried my thumb to the hilt. Four years of various one-night stands at university as well as numerous relationships so far, I knew my way around a vagina, and in no time my thumb located her G-spot and I started to stimulate it.

"Oh, oh ah," the moans from Demi started getting louder as I continued playing with her G-spot. I could see she was on the verge of cumming as she started to move her hips frantically while fucking herself on my thumb. Just as I thought she was about to have an orgasm I pulled my finger out.

"Oh, fuck nooooo don't!!" she practically cried as I stopped all stimulation.

"Oh yes. If you want to cum, you'll have to beg me."

"Fuck you."

"Fuck me? Oh, absolutely you will, but before that you are going to beg me."

I stood up and pulled my pants off and placed my erect cock right at the entrance of her pussy lips and rubbed the bulbous head all over the entrance of her wet pussy. After a few seconds she realised I was just teasing her and she tried to push her arse back in frustration.

"Damn it Dan, just push it in," she whimpered as I teased her mercilessly.

"You can be a lot more polite than that Dami," and without any warning I pulled back and slapped her naked buttock hard.

"Urgh!!" she yelled as I followed the first slap with another one. I felt a bit sorry for her as her pale white skin turned red, but I could also see her pussy was leaking buckets.

"Let's try that again," I grabbed my cock again and teased her pussy from behind.

"Please Dan push it in, I'm so close." She begged as I pulled back the skin of my uncircumcised cock and sunk an inch of it inside her pussy.

"That's better, but maybe I should leave your pussy alone and fuck you in your beautiful arse instead," I told her as I pulled my cock out and rested the head on the entrance of her backdoor.

"Please no. I've never had anything in there."

"I'm not asking you for your permission Demi," I told her as I grabbed my cock and pushed it firmly into the entrance of her arsehole.

"No, no ,please stop, that hurts," she screamed as I felt my mushroom head starting to expand her sphincter.

"Don't you dare take your hands off that table," I warned her as I held her by her hips and enjoyed the heat I was feeling on my cock. I was so tempted to just push the whole thing at one go but I did not want to hurt her either.

"Tell you what Demi, I'll make you a deal. I am going to leave your arse alone for now as long as you promise to let me prepare it later with lubricant before I fuck you. I promise you; you'll be begging for it after that,".

"Yes, yes, that's fine. Please take it out. It feels so weird." She did not sound very convinced, but I aimed to change her mind soon.

"I'll hold you to that," I told her as I pulled away from her arsehole and pushed myself back in to her sopping pussy. She was so wet I literally found no resistance and her pussy gobbled all of my eight-inch rod steel in one smooth push.

"Oh my fucking God," she yelled as her arse pushed back trying to take in as much as possible. I held still and just enjoyed watching her fuck herself on my cock.

"Urgh!!" Just a few seconds later Demi let out a scream as she slammed her arse back on my thighs and I felt a sudden gush of liquid around my cock. I was almost worried she had peed herself before realising she was just having an explosive orgasm.

I wanted to show this young girl what an experienced guy can do. So, I waited until she started calming down before reaching around her and locating her erect clit. As soon as I touched her engorged clit, I also positioned my cock inside her creamy cunt directly stimulating her G-spot. Tormenting both her erogenous zones at the same time was too much for Demi.

"Ahh fucking hell!" she screamed again and buckled under me as another orgasm took over her body. I had no idea if she's ever had a multiple orgasm but I felt like I was riding a rodeo horse as I did my best to continue diddling her clit as I felt her inner pussy muscles quiver around my cock.

I couldn't believe how snug and tight her vaginal tunnel felt around me, even after a few explosive orgasms that ripped through her body.

As I continued stimulating her engorged clit, she feebly grabbed my hand and tried pushing it away.

"Please, my clit is so sensitive it hurts now," she practically begged.

"I'm going to be nice to you and give your clit a break," I told her as I took my fingers off her clit and gripped her hips firmly as I gently fucked her pussy.

"Did you enjoy that Demi?" I asked her as I started picking up my pace.

"Urgh urgh ya, I've never cum twice like this, ever," she replied tiredly as her body slumped on the table as I fucked her from behind.

"Well, I am happy to hear that, but I have no intention in coming inside your sweet pussy. I'm going to try your arse again but as promised I'll take it easy; you just have to relax and do what I say ok," I instructed as I pulled out of her thoroughly fucked cunt.

"Ok... but please just be gentle."I was glad she was turned away from me as I had a massive shit eating grin as I realised, I was going to sodomize this beautiful young girl and take her anal virginity.I looked around and saw her bag on the table. Without asking for her permission, I reached for it and opened up. I located a tube of hand cream she had and pulled it out.

"I am going to make sure you are going to enjoy this," I said as I patted her soft buttock as I knelt down and opened up her arse cheeks. I squirted an ample amount of the hand cream onto my fingers and thoroughly lubricated them before placing my middle finger on the entrance of her arsehole.

"I'm going to slip my finger inside your arse and make it slippery, but I can only do this properly if you help me. If done properly it won't hurt you, trust me," Not sure if she trusted my words but she turned back and gave me a slight nod and looked fearfully with those big brown eyes.

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