Teaching Demi Ch. 02

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For Women

This is a continuation of my story Teaching Demi 01. I strongly suggest you read that first before reading this episode. As always, any feedbacks and comments will be appreciated. The story includes anal sex, so if it is not your cup of tea please do not read further.

“Ouch put more cream please Dan,” whimpered Demi as I tried slipping my erect cock inside her tight arsehole as she stood there bending over that desk again, with her skirt pulled up.

Since that fateful day when I confronted her about her work ethics and took her anal virginity, this has become quite a routine almost every day after work.

Apart from enjoying this young girl’s tight poop chute, I was also loving the control I was having over her. I was consumed with the need to see her bent over submissively on the table as my cock disappeared inside her hot fragrant bowels. Knowing that she went back home to her boyfriend while my cum seeped through her arsehole just made the whole experience more exciting. 

Even during working hours, whenever possible, I would run my hands over her tight body as she stood there obediently letting me have my way with her.  

I also strongly suspected my actions throughout the day were turning her on just as much. Usually this is confirmed when I plunge my cock inside her pussy to lubricate it before I take her arse. 

Not only is she willing and ready to go each evening, I find her pussy and her panties soaking as soon as I slide them down her slender legs. 

As I enjoyed the now familiar friction my uncircumcised cock feels when the mushroom head slips past her sphincter muscle, I grabbed her hair and pulled her back roughly towards me.

“I’m addicted to your arse Demi and don’t forget I decide if we need more lube or not,” and to prove a point I roughly pushed my cock in as her sphincter muscle quickly gave up its feeble resistance and the bulbous part of my cock barged inside her hot anal tunnel. 

“Urgh…,” she whimpered but shut her eyes, bit her lips and gave an extra wiggle that she had learnt necessary to accommodate my cock inside her backdoor, with minimal pain. 

I was almost disappointed that she did not complain as I pulled myself out and spat generously on my cock before grabbing her hips and roughly pulled her towards me until her arse swallowed my stiff cock to the hilt. That earned a loud moan from her as she twisted her hips and matched my strokes as I slowly sodomised her. 

I leaned forward and using my hand I turned her face towards me and covered her mouth with mine. She willingly parted her lips as my tongue quickly slipped between her luscious lips. Although in this position neither one of us could move, we both enjoyed the sensation of her anal muscles gripping my cock tightly as I mauled her mouth with my tongue. 

I reached around and started diddling her engorged clit as we swapped saliva and tongue fucked each other. A few minutes of stimulating her clit, with my cock firmly buried in her tight arse, had Demi screaming out in to my mouth as a powerful orgasm took over her. 

“Oh, oomph yes!!” she moaned in to my mouth as she pushed herself on my fingers as she rode her orgasm. Her action also increased the pressure on my cock that was surprisingly still latched inside her anus as she thrashed around.   

I knew I could not wait any longer as I started feeling that very familiar tingling feeling near my balls. So, I reluctantly pulled away from her mouth and grabbed her by her shoulders and fucked her hard and fast racing towards an explosive orgasm of my own.

“Fuck yes,” I bellowed as with one final push I deposited my seeds deep in to her hot bowels.

I continued moving inside her tight arsehole until I felt my balls empty and my cock started to soften. I pulled out of Demi’s now very slippery arse with a satisfied grunt. Just before her tight backdoor shut, I noticed my cum ooze out of her hole with her natural brown fluids.

“Now that is how each working day should finish, I’ll see you tomorrow at 9.00,” I informed her with a satisfied grin as I admired her well fucked bottom as I wiped my well used cock on her black panties. 

As I watched her meekly stand up and subconsciously rub her abused arsehole while picking up her panties, I felt my loins stir again.


By the time the first month passed, any remaining resistance Demi showed had completely disappeared and she had become my very own plaything. She had grown so accustomed to our frequent sex sessions nothing surprised her anymore.  I thoroughly enjoyed fucking this beautiful little minx to my heart’s, or should I say my cock’s content; but annoyingly, even though bending her over the edge of the table worked for us, I was getting frustrated with the lack of space at my shop and I could not wait to get her on to a proper bed. 

As luck would have it, our yearly trade show was around the corner and as this usually happens in Birmingham, this was the perfect opportunity to get ataşehir escort her in a room with me.

After thinking of what’s the best way to approach Demi, I decided to confront her straight in the morning as soon as she walked in at 8.45 am.

“Demi, lock the door behind you and come up with me please,”. 

She looked at me in surprise as I normally don’t ask her upstairs until late in the afternoon, just before we shut shop.

“Listen, apart from what we’ve been doing upstairs I am actually starting to see a massive improvement in your work and I want to reward you,”.

As soon as I said reward, I could see her visibly looking excited.

“I don’t want to give you a pay rise as just as yet, but I am going to put you on a bonus scheme where a percentage of your sales will come back to you each month,”.

“In order to give you a fighting chance of selling more so we both can make more money; I need to send you for some further training of our products. With the trade show in Birmingham over this weekend I think it will be good for you to spend a couple of days over there,”.

I smiled at her as she looked excited and visibly pleased with the idea of more money each month, but then I saw her face drop as the reality sunk in. 

“Oh, that’s great Dan but I am not sure I can afford the train ticket as well as a hotel this close to the show,” she pointed out sadly.

“Oh well, I understand but it’s a really good opportunity that you should not miss. Just drive with me and I’ll treat you to a nice hotel room,” I said not showing my excitement.

“Oh, umm I’ll have to ask my Boyfriend and Mum about this,” she did not sound convinced so I decided to go back to my original tactic.

“Listen Demi, you are becoming a good employee, but if you want to progress in life and earn more money it’s time you made your decisions and not rely on others, I don’t easily give opportunities like this and do you really want to miss such a great chance?”.

“No no I definitely want to go…It’s just that my boyfriend can be quite jealous,” her voice trailed.

Well with the things I do to you, he should be!  I quietly laughed inside as I started getting turned on looking at her pleading face.

“Forget about your loser boyfriend and focus on your career Demi, you don’t want to live for the rest of your life in your mum’s house, do you? With the right training you have the ability to become my manager and run the whole shop. Can you imagine the commission you’ll earn each month if that happens?”.

No, of course not and yes you are right, I need to think about myself. I’ll come with you, Thank you so much for the opportunity Dan,”.

Game-Set-Match I thought to myself as that went a lot easier than I thought it would. 

“Well now that’s settled let’s focus on something else before we open the shop eh” I said as I stood up and unbuckled my pants.

There was virtually no hesitation as she sprung up and moved towards the table to bend over.

I think I surprised us both as I pulled her fiercely towards me and kissed her hard on her lips.

“You may have a boyfriend but when I want you, you come to me understood?” I whispered in her ears as I kissed her passionately running my hands all over her plump arse cheeks.

“Yes Dan, I’m yours,” she moaned as my now very hard cock pressed in to her belly. 

Her sexy lips parted as my tongue barged in and sucked on her mouth. My hands were placed firmly on her arse, kneading her plump cheeks as I mauled her lips. Her lipstick was ruined and I probably had it all over my face but that hardly bothered me as I dry humped her standing up as she melted in my arms. 

“On your Knees looking at me Demi,” I ordered as I pulled my pants and boxers down and gave my fully erect cock a couple of strokes looking at her expectantly. 

She got on her knees and opened her mouth to suck me, but I pulled back.

“No not your mouth, stick your tongue out instead,” I ordered as I pulled my foreskin back and rubbed the bulbous head on her wet tongue. 

She knelt there motionless with her tongue out like a good girl as I continued moving my cock up and down on her tongue.

I looked in to her hazel brown eyes as I fisted my cock rubbing the sensitive mushroom head all over her pink tongue. Every often I would gently part her lips and push the bulbous head inside her wet mouth and lubricate it before pulling it out and wanking on her tongue.

Her playful tongue licked up and down my shaft as I took my time stroking my cock.  I grabbed her by her hair and directed her mouth to my balls as I continued jerking off. I groaned in pleasure as she sucked gently on my balls.

The constant stimulation of my nether region and the submissive nature of Demi had me reaching boiling level very quickly. 

“Now open wide,” I ordered as I approached my first orgasm of the day. 

Like a good employee she quickly parted her lips as I started fucking her face with my cock. kadıköy escort bayan Although I was very excited, I did my best not to push too hard and fucked her mouth with just half the length. She barely gagged as she sucked like her life depended on it, while breathing deeply through her mouth. 

“Here it comes, make sure you swallow it all,” I warned her as I started to move my hips faster. 

“Oh yes!!” I groaned as the first spurt hit the back of Demi’s throat, like a trooper she swallowed quickly and opened her mouth again as the second and third squirt quickly followed. 

I continued fisting my cock as Demi’s mouth milked me dry with ease.

Finally, as my balls fully emptied, I pulled back with a satisfied moan.

“You are soon becoming my favourite Demi,” I smiled at her as I pulled my pants up and made myself decent to go downstairs. 

She looked at me proudly as she stood up with a spring in her legs and followed me downstairs. 


It was all arranged for the trip and I asked her to pack her bag for 2 nights as we decided to drive straight from work on the Friday evening.

Although I’ve fucked her numerous times and cum in all three of her holes’ countless times, I was very excited for the weekend. Looking at her all agitated and on edge all day on Friday, I could see we both shared the same thoughts. 

I did not fuck Demi after work as I had other plans on the road. She looked visibly disappointed that I did not ask her to come upstairs as we quickly shut the shop, and set the alarm, before getting in my car. 

The start of the journey was uneventful as I was busy negotiating the London traffic. By the time we hit the motorway it had considerably got darker, so I stopped at the first service stop on the M1 and grabbed each of us a drink.

As we came back to the car and Demi started to put the seat belt on, I stopped her.

“Before you put your seat belt on pull your panties down and give it to me,” I ordered her as I looked at her. 

She hesitated for a second but as soon as she saw the look on my face, she quickly pulled her panties down and handed them over.

Just as I suspected her cotton panties were soaking where her pussy rested. 

“Nice,” I whispered out loud as I brought them to my nose and inhaled the musky smell that I had grown to love. 

As she sat their fidgeting, I reached over and parted her legs wide. Unceremoniously, I Pushed my middle finger inside her wet pussy as my lips found hers.

“Mmmm,” she moaned in to my mouth as I fingered her in the middle of the car park. The thrill of getting caught was evident on Demi’s face as she started humping my fingers enthusiastically. 

A part of me wanted to be an arsehole and pull away but instead I shoved another finger in and started to finger her in earnest as I sucked on her tongue. Realising she was approaching her orgasm quickly I located her clit and diddled it with my thumb and as predicted that set her off. 

“Urghhh!!” she moaned loudly in to my mouth as her orgasm took over her body. I could see her erect nipples almost threatened to burst through her dress as she rode her orgasm. 

Finally, she calmed down as I eased by fingers off her well fingered pussy and brought them to our mouth.

I sucked one finger dry and offered the other one to her, credit to her she took it like a trooper and sucked her own pussy juice. 

Reluctantly with one final kiss I pulled away from her sexy plump lips and started the car with a painful hard on and brought us back on to the motorway.

Once on the road however, I quickly activated cruise control and set the speed at 60 M/ph and moved the vehicle to the slow lane. 

Demi was still recovering from her orgasm as I unzipped my pants and fished my erect cock out.

I grabbed her hand that was nearest to me and brought it to my exposed cock. 

She understood what I wanted and moved as close as possible to my seat and started jerking my cock as I kept my eyes on the road. By now I was leaking pre-cum steadily and she used her fingers to spread it all over my sensitive mushroom head and started to jerk my cock faster.

“Not that fast, slow down,” I mentioned to her with gritted teeth as the sensation was too much.

She slowed down the movement but gripped my cock harder and slowly pulled my foreskin up and down while stimulating the pee-hole with her thumb frequently. 

An animalistic grunt escaped my throat involuntarily as I struggled to keep my eyes open from what felt like all of the blood rushing to my cock. 

The fear of getting caught, or worse crashing the car, with the sensation I was getting due to the expert hand job given by Demi was racing me towards my impeded finish. 

Just five minutes of this painfully slow wank left me on the edge of a seriously powerful orgasm. Throwing caution to the wind I grabbed her by her hair and pulled her face to my crotch. Credit to Demi, without escort maltepe letting go of my cock she unbuckled her seatbelt with her free hand and scooted up and took my cock all the way in to her mouth. As soon as my sensitive head touched the back of her throat, I lost it and yelled as I ejaculated hard.

“Fuck!!,” I grunted as I pumped Demi’s stomach full of my sperm.

“Oomph oomph,” she moaned as she continued sucking until I could not take the sensation anymore and I gently pushed her away. 

“That was amazing and it’s a miracle I did not crash the car,” I grinned at her as I did not bother zipping up my pants and switched back to manual drive and sped up to Birmingham. 

The rest of the two hours passed uneventfully as I probably broke many speed limits and got to our hotel in record time. 

Unbeknown to Demi I had booked a room with a large Kingsize bed for the next two nights with a luxurious bathroom suite. 

Once checked in, I let Demi look around as I made a few phone calls. As someone who travels a lot nothing surprised me too much about hotels, but it was evident from Demi’s face she did not get to stay in luxurious hotels often and she was in awe of everything. By the time I opened the door to our hotel room and ushered her in, her jaw was on the floor as she looked around in awe. 

As I enjoyed her astonishment, I realised in a strange way I was getting fond of her. 

Maybe because of the nearly daily fucking or the fact she literally said yes to every perverse request without putting up any fight these days, I was under the impression I was going to get bored of her soon; but surprisingly I started to realise I was almost getting addicted to dominating her and taking her at will. 

I did not know if the reality had set in for Demi regarding the sleeping arrangement as clearly there was only one room with one bed there but if it did, she did not show it as she popped her shoes and socks off and looked around just in total wonder.

Finally I had Demi in a room with a bed! I wanted to do so many things at the same time but instead I think I surprised both of us as I pulled her to me and kissed her passionately. 

Demi simply melted in my arms as she opened her mouth and let my tongue in. As we French kissed fervently, my hands as usual soon found her plump arse cheeks and groped her shamelessly. With our clothes still on, I pushed her gently on to the bed and quickly got on top of her. 

She involuntarily opened her legs as my hard on rested firmly on top of her skirt covered crotch. I ran my hands over her smooth legs just enjoying the feeling of soft smooth skin all the way to her plump hips, with no resistance, as I remembered her panties were still in my car. 

I quickly moved my fingers to her groin and found her sopping wet pussy just leaking lubrication. 

“About time I see you naked,” I whispered in her ears as I stood up and dragged her skirt off her. She sat up and quickly pulled her blouse off. I stopped her from unhooking her bra ,as I wanted to do it instead ,and reached behind her and unhooked her silky bra. Finally, her voluptuous breasts were in full display. Experience showed me that her breasts were probably a healthy D cup, and owning to her age and probably how horny she was, there was virtually no sagging in her magnificent boobs. I ran my fingers over her warm and succulent looking breasts before resting my fingers on her erect burgundy-coloured nipples that stuck out like gumdrops.

Subconsciously her hands went to cover her exposed breasts, but a quick swat from me and she very quickly moved her hands away and pushed her breasts proudly as my eyes feasted on her tight body. 

Unable to stand any longer I pulled my sweater off exposing my muscular chest and abs to her for the first time. Her hands automatically traced my muscular midriff before she fumbled awkwardly with the belt of my trouser. I helped her by unbuckling the belt and Demi pushed my trouser and boxer shorts lower exposing my erect manhood. The awkward positions weren’t particularly erotic so I quickly hopped out of the bed and pulled my pants and socks off. 

Finally, as naked as the day we were born I approached her and got on top of Demi. As my lips found her lips my cock grazed her moist slit. 

My tongue parted her lips and started exploring her mouth. 

“God, your body is so unbelievably hot,” I whispered in to her mouth as I took turn sucking on her plump lower lip and her wet sexy tongue. 

“You are driving me crazy Dan,” she moaned in reply as our mouths mauled each other. Our hands explored each other’s naked body as her hips subconsciously grated under me in heat. 

 I grabbed her hands and got them over her head while my lips moved from her sexy lips to her sensitive neck.

“Urghhh!!,” she groaned in pleasure as I licked her neck and sucked on her earlobe. 

“Please Dan, I am ready,” Demi begged me to fill her hole. 

“Not so fast, the night is still young,” I assured my young lover as I travelled south and gently licked her voluptuous bosom before firmly sucking on her upright nipple.

“Oh God, suck them hard,” she whimpered as I teased her mercilessly and took turns on her tits sucking on them like a hungry new born. 

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