tagAnalTeaching Demi

Teaching Demi

bydansouthwest©

"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 staff at a time. When my previous staff retired I was gutted as she was an amazing worker and very good with the 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 college 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 then I was left trying to juggle two customers at the same time.

I had sat 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 as the front door to the shop was open and I was starting to hate the fact she was taking advantage of this situation.

However, unbeknown to her, last week I had installed a CCTV camera 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 now to 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 the fuck 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.

"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 don't give a fuck what your mum does to you. In fact I am not even going to pay you for this month. So bugger off," I usually never swear but the girl had brought the worse 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 bitch, you fucked up. I haven't given you a contract as yet and taking in to 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 realised suddenly I wasn't angry anymore but in fact watching Demi cry in front of me was starting to arouse me. I looked at her intently. She was around five foot five and around fifty five kilos. Her blond hair was put up in a pony tail and her bright blue 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 knee cap, and if I had seen her in the streets I would have probably mistaken her for a secretary or a school teacher.

"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 and my eyes ran over her body. 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 can't do that. 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 I think about it I do realise how badly I messed up. Please give me one more chance."

"I'm sorry but I can't think of you as a 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."

"That's a shame as that's not my problem You'll have to explain why you can't pay your rent to your mother when you get home. Now leave now please."

"Please no. Ok, I really will do anything you want, I really mean it. Anything! I have to have this job." She was now truly pleading with me.

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.

"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 blue eyes and nodded slowly almost in defeat.

"Now, hold on to the table and bend down," I instructed as I watched her intently.

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

"Straighten both your hands and hold on to the table edge. I do not want your hands to move unless I tell you to," I instructed her and waited until she followed my instructions.

I stood right behind her arse and pressed my erect cock through my pants on to her arse cheeks.

I heard another sob escape her throat as I moved my hips harder against the cheeks of her arse as I slowly dry humped her. Through 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 fun. She hadn't moved or said a word.

Realising she was actually going to let me do everything to her young body I started getting a bit more bold. I knelt down behind her and ran my hands over her naked calves before pushing her dress up. As soon as I pulled it up over her arse I was pleasantly surprised to find her not wearing any underwear.

But then as the dress went totally up I realised she was in fact wearing a very tiny black thong that had disappeared inside her arse crack.

I took hold of her thong from both sides and pulled it down to her ankles and told her to step out of it. I held the tiny garment on to my face and smelled it again, this time pressing the part that would have been on her 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 as I brought my face down to the same level as her arse.

"Now, let's see how your arsehole smells." Her sobs were getting louder as I grabbed hold of her buttocks and pried them open.

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

"Remember, no resistance, and no complaints."

That quickly shut her and I went back to admiring her tiny rose bud. She had done her best to shave around her hole and I wondered if her boyfriend did any of the things that I wanted to do to that hole.

I put my leg in-between hers and nudged them apart. She yielded to me and she parted her legs allowing me better access to both of her private holes.

I've always been as ass man and the fact I haven't had a new ass 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. Close inspection revealed she had done a poor job cleaning her arsehole after her recent bowel movement. There were tiny brown specks around her wrinkled hole.

"You really must learn to wipe properly." I took her thong and placed it on her arsehole and i proceeded to wipe her backdoor clean. "See you just wipe front to back until your stinky hole is clean. Not rocket science is it?" I continued tormenting her with my words as I pushed her black thong inside her arsehole as much as possible as I cleaned it.

"Now let's see how you smell and taste." I brought my nose right on to her anus opening and took a deep sniff. I used my thumbs to open up her asshole a bit more as I moved my nose around her tiny hole and inhaled her musky scent. Although I had cleaned her up well with her thong, the earthy musky smell was still clinging around her arsehole and it was turning me on tremendously.

"God you still stink but I must admit that I am starting to like your smell," 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 starting to drive me crazy, but at the same time I couldn't wait to taste her rear end either.

"Has anyone ever smelled your arsehole the way I am smelling it?".

"Oh God no. No one's ever touched me there!" She sobbed as she spoke without turning around.

"Well then you are going to find this very interesting," I told her as I stuck my tongue out and gave her arsehole a long lick.

"Oh God ewww stop," she yelped and tried to push her butt out as she felt my wet tongue on her anus opening.

"Quiet. Remember your promise."

I took this chance to spread her arse cheeks wide again with my hands and taste the area around her anus hole. It was definitely tangy as I expected and as I got closer and closer to her arsehole the taste was becoming bitter.

"Do you want me to guess what you had for breakfast?" I smirked in between the licks as I used my fingers to open up her arsehole, inserting my tongue deep in to her bowels without waiting for an answer from her.

"Oh God, this is so disgusting," she said with gritted teeth as my tongue went a couple of inches inside her virgin arsehole. I responded to her words by forcefully opening up her arsehole even further and tongue fucking her.

As I continued my attack on her anus opening I started noticing my chin was getting a bit wet and a quick check of her pussy lips with my finger confirmed she was actually getting worked up with my tongue up her arse.

"You can pretend to hate it but your pussy is saying otherwise," I told her a I pulled out of her arse and pushed my thumb into her soaking wet pussy.

She yelped at the sudden intrusion of my thumb inside her wet pussy. I grinned to myself as I realised how wet she was. Four years of various one night stands at university as well as numerous relationships so far, I knew my way around a vagina, so in no time my thumb located her G-spot and I started to stimulate it.

"Oh oh ah," Demi started to moan now as I continued playing with her G-spot. She was on the verge of cumming. Just as I thought she was about to have an orgasm I pulled my finger out.

"Oh no don't," she practically cried as I stopped all stimulation. To make it worse I also made sure her legs were nice and wide apart so she was not going to rub her thighs together and get off.

"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."

With that I stood up and unzipped my pants and pulled out my stiff cock. I placed it right at the entrance of her pussy lips and gently moved it around her vagina. However, every time she started to push her arse back trying to make me push my cock in, I moved away.

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

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

"Urgh!!" she yelled as I followed the first slap with another one. Her pale white skin turned red in record time. I grabbed my cock again and rubbed her pussy from behind.

"Please Dan push it in, I'm so close."

"That's better, but maybe I should leave your pussy alone and fuck you in your stinky arse instead," I told her as I moved my cock away from her pussy lips and on to the entrance of her backdoor.

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

"I'm not asking you, I'm telling you," I told her as I grabbed my cock and pushed it hard into the entrance of her arsehole.

"No no please stop that hurts," she screamed as I felt the mushroom head of my cock 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 want, 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. Either that or I just shove it in dry and make your arse bleed," It was not much of a deal but I was not in a very generous mood when it comes to a virgin arsehole.

"Yes yes that's fine. Please take it out It feels so weird," she was practically begging and probably didn't even think about what she had just agreed to.

"I'll hold you to that," I told her as I pulled away from her arsehole and shoved my dick into her soaking wet pussy in one smooth motion.

"Oh my fucking God," she yelled as I buried my cock to the hilt and started fucking her as I gripped her hips with my hands. By the second stroke I knew she was cumming as I felt a 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 older man can do so I decided to treat her to a proper fuck. I waited until she started calming down before reaching around her and locating her erect clit. As soon as I touched her erect clit I also positioned my cock inside her pussy at a position where it was directly stimulating her G-spot. Touching both her erogenous zones at the same time was too much for Demi as she screamed again and buckled under me as another orgasm took over her body. I had no idea if she's every 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 she buckled under me.

I stopped moving and let her ride her orgasm as I enjoyed the feel of her tight pussy around my cock. Although she'd already cum twice and my balls were becoming wet with her pussy juice that was dripping out she was still incredibly tight around my cock. The sensation of an eighteen year old pussy around your cock is something that just can't be explained by mere words!

"Please, my clit is so sensitive it hurts now," she practically begged as I continued stimulating her clit.

"I'm am going to be nice to you and do what you ask," I told her as I took my finger off her clit and gripped her hips as I slowly moved my cock in and out of her pussy.

"Thank you, thank you," she genuinely sounded grateful as I continued my slow fucking.

"Don't thank me just as yet as I have no intention in coming inside your sweet pussy. I'm going to try you arse again but as promised I'll take it easy, you just have to relax and do what I say ok," I instructed without stopping my fucking.

"Ok but please just be gentle."

I knew by then I had broken her!

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.

Reluctantly I pulled out of her tight pussy and she almost whimpered in disappointment.

"Don't worry if you are good, you'll feel full again in no time," I said as I patted her soft buttock before sitting down on the chair as I brought her arse to my eye level.

I squirted ample amount of the hand cream onto my fingers and thoroughly lubricated them before placing my middle finger on opening to 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 to look at me with her baby blue eyes.

"Reach behind you and spread your cheeks wide," I instructed as I waited for her to do what I had asked her. I could have done it myself but I was enjoying dominating Demi.

She hesitated a second before taking both her hands and holding her arse cheeks and pried them open.

"Good girl! Now gently bend your knees a tad."

Again she followed my instruction to a tee. I was glad the hidden CCTV camera was recording all this as Demi on the table with her hands spreading her arse cheeks as she bent her knees was something I never wanted to forget!

I placed my well lubricated middle finger on to the entrance of her anus before I gave her the next instruction.

"I'm going to push my finger in and this will feel weird but don't fight it, instead pretend you are taking a shit and push."

"Oh God no," my words must have mortified her.

"Listen I can push my finger in without warning you but I promised you I won't hurt you if you listen to me Do what I say as this finger is going in your arse whether you like it or not," I placed the middle finger on her arsehole and started pushing it in to the tight hole.

"Ok ok," she almost panicked before she bent her knees further almost to a squatting position as she tried pushing.

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