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Learning to Ride

Riding Lessons of Different Kinds

I have to watch my girlfriend ride horses. It is dull, I won’t lie to you. I’m not one for standing around, listening to some high and mighty bitch bark orders at my girl telling her to sit up straight, she’s not doing it quite right, etc., etc. It makes her feel inferior—useless, even, and this results in us driving home in silence. We then have a row, the Sunday is ruined, more so by the fact that the day before she would have joined me at the football, which is always way better. It pains her to admit it, but we always have a really great time at the games. I have asked her to drop the riding lessons countless times, but my Suzy is not a quitter and she will not give up until she has mastered whatever new-fangled idea she has jumped on.

This whole fucking fiasco of a routine, which rudely interferes with my Sunday morning hangovers, can only be slightly comforted with the sight of Maria, the one and only girl on the entire planet that my girlfriend claims to hate with intense passion.

I remember the first day she arrived at the stables while we were there. As I watched her mount I was aware that I was full on staring, yet I could not turn my eyes away. Even harder to ignore was my massive boner pushing its way out. With her whip in her hand, she was the ultimate temptress. The crystal-embedded head glistened in her hand, her grip strong around the metal thread braided shaft. I should have felt guilty that I was paying her so much attention. The way I reasoned with it was that being here was much less of a bore with her around. It wasn’t long before I was proven right, in more ways than one.

Everything about her looked young, rich, and wild. She was loud and reckless when she spoke, caring little of upsetting her horse or anyone in near proximity. She looked perfectly groomed yet crazy at the same time. Sharp, blue eyes and deep olive skin which could only be achieved from eight holidays a year to Barbados, courtesy of daddy darling. I could certainly see where the resentment was justified from Suzy’s point of view, but Maria was a breathtaking sight all the same. She had an almost sickeningly large sense of confidence for a girl so young. At just 18, she seemed so much older in the way she feared nothing, no one, and had no trouble speaking downwardly to anyone she took a negative view of.

I knew this would end badly, but I couldn’t stop looking at her. She had the longest, blondest, shiniest hair I had ever seen and it looked beautifully disheveled like she’d just woken up that way, but perfect all the same. She oozed effortless sophistication and class. She was dressed in bespoke jodhpurs of navy and lilac dogtooth which clung to her peach behind like a second skin. Her boots were Burberry, black with military medal and equestrian loop detail at the back, covered by her half chaps of black nubuck and suede. My girlfriend had talked about this girl in bitter, intricate detail. “She turns up in her pretentious riding get-up acting like she owns the place.” It was probably inappropriate of me to point out that she was, in fact, the stable owner's daughter, but all the same, I did it anyway and, yes, another row broke out.

The day it all kicked off was an extremely quiet day. There was only my girlfriend and I there. As we conversed with Mrs. Pickering about the lesson ahead, I heard a scream from the stables. We all heard it. Mrs. Pickering suggested I go and check it out while she told my girlfriend to mount and prepare to begin.

With trepidation, I headed over to the stables. I had no idea what I might be faced with. I stood tall and looked around the land for potential weapons in case the screams belonged to someone being attacked. Of course, this was not a movie, so there were no convenient weaponry randomly lying around. I cursed myself for being a bit of a twat and continued to walk, back straight, giving me an extra couple of inches in height, which would of course have made all the difference, should there have been some mad raving lunatic waving a machete amongst the hay.

As I neared the stable, everything became eerily quiet. I didn’t like this one bit. The screams I had heard less than a few minutes ago had dissipated into nothing at all. I heard no cries, no whispers even, and I started to think that I imagined the screams, only changing my mind when I remembered that my girlfriend and Mrs. Pickering had heard them, too.

I took a quick look around the fields and surrounding landscapes and, in the distance, I could see Suzy had mastered the canter. She had been complaining that her rhythm was out of sync with her horse and feared she may never get it right. The sight of her now gracefully motioning across the rolling hillsides beyond made me smile and I couldn’t help but wonder if she would ride me with the same enthusiasm when we returned home that evening. I figured it was the least she owed me after making me endure this shit week in week out.

On entering the barn, I did not find myself greeted with a chaos worthy of becoming a crime scene. There was no sign of a fight, of someone being harmed, no disruption to the order of things, just a very sly looking Maria with a large smile spread across her face. I could not work out why we had heard screams when everything seemed to be just fine.

She smiled the most wicked of smiles. I was confused. 

“I heard screaming” I said. 

This was met with raucous laughter, which served just to throw me further off kilter. She was enjoying herself and I could make no sense of what was going on. 

“You were meant to hear me...” she trailed off and erupted into further fits of hysterics. She was beginning to look a lot less attractive and a lot more a like a headcase bitch. She was sat on a rectangular stack of hay with a sway in her body and, as I looked closer, I could see a bottle of Merlot half drunk by her side. She looked almost maniacal, struggling to hold up her upper body and continuing to laugh aloud, yet I was still failing to get the joke.

“Sit,” she said, patting the bale to her side. “Have some wine, go on, go ahead...” 

She was so arrogant and sure that I would do as she ordered it made me sick. Feeling quite angry about the whole situation and pissed off at her inability to calm herself down and speak coherently, I took the bottle and drank down a large amount of the contents. 

“Look, I really don’t know what is going on here,” I said. I wanted to give her a slap for thinking she could talk to me like a lame arse piece of shit, but instead, predictably, I am a lame arse piece of shit and I clumsily walked right ahead and sat down as she instructed. In my mind I cursed myself for being a twat for the second time that day. My dick must have been making me fucking stupid and I could only come to the conclusion that it would be in my best interest to get laid soon. Being close to her and being able to view the floor behind her I could see that this was not her first bottle, as two more empties laid cack-handedly on the hay. 

“I think we need to sober you up before your mother finds you in can you please tell me what is going on?”

“My mother” she retorts, “who cares about that bitch!” 

She leant back against the bales and rested her head against them. She had the most deviant smile on her face, which made her look incredibly sexy, and with her back arching slightly, her breasts were pushing forwards, stretching the material of her t shirt so much so that I could make out the intricate lace detail of her bra underneath. Before I had a chance to begin guessing which colour she might be wearing, she continued to speak. 

“She wants you, you know. At my 18th Birthday, that cougar tramp had the pleasure of embarrassing me in front of all of my friends, delighting in informing them that the 'new sap’s boyfriend is ripe for the picking.'” She quoted her mother in the dialect and accent of her which made me laugh. It was spot on! 

“I don’t understand what you mean?” I said. I’m not completely stupid but I was enjoying where this revelation was leading, so I probed further. 

“Oh, come on!” Maria said, “My mother is desperate to make you her next notch on the bedpost. She has a string of young men a quarter of her age on her agenda and you’re next!” 

I blushed slightly and she could see that I was aroused, much to my shame. She laughed aloud again, making me feel about two inches tall. When she finally stopped laughing at me, she went quiet and whispered, “You see, the thing is, I daren’t date any men in the village for a fear that they have already slept with my mother. My guess is that you haven’t yet which leaves you a sure thing. You are my only hope at getting some fun in my life.”

She leaned in close, stinking of red wine and cigarettes, brought her merlot stained lips real close to my face and kissed my top lip so gently and seductively I could be forgiven for wondering if they actually touched mine at all. She was beautiful, even as a drunk wreck and even with every screaming alarm ringing out in my mind to stop this now. I was unable to resist. She kissed me again and this time, I felt it. Not because it was good, though. This time it felt desperate and clumsy. Her breath was stale from the chain smoking while we’d been talking and her hands were all over me, tugging at my shirt and fumbling around my jeans, trying to grab a handful of dick. Her amateur style and neediness was pathetic and off-putting, but at the same time, I was unable to ignore the heavy weight of my balls needing to get some release. The more I thought about it though, the more I found myself getting hard and horny. Here was this whiny little bitch giving me the big “I am” and yet now, when it came down to it, she’d gotten awkward. Time for me to take a bit of action. 

“You wanna see my dick?” I said, “You’re gonna have to ask real nicely.” 

She looked at me like she had never been challenged before, one eye raised and about to let out a giggle. 

“I mean it,” I said as I grabbed her right wrist and squeezed it tight, pulling her away from the zip of my jeans. A glaze of submission appeared in her eyes. I’ve seen it before in Suzy. Those rare occasions where we have been out and she’s gotten herself so wasted on booze that she’ll give me this look once we’re home, then flip herself around so she’s facing away from me. Be it in the kitchen over the worktop or lying down in bed, she allows me these times, and only these times, to shag her up the arse.

Maria glanced down towards her wrist, which I still had a tight hold of. Looking back at me straight in the eyes, she tilted her head to the side all cocky and said “Yeah, OK big guy, if it makes you happy, I want to see your dick. Now stop playing around...” 

She tried to free her hand, but I squeezed tighter and replied “Now that is no way to ask is it?” 

I felt like some fucking hot shot mother fucker at this moment and knew she’d cave. Christ, she was so up for it. I could have made her beg for hours. Thing was, I needed it too, and we didn’t have much time. 

“I want you naked,” I say “Now." She looked startled at my sudden authoritative tone, yet she clearly loved it. Without hesitation, she began to slowly undress. She stumbled a few times trying to squeeze out of her jodhpurs but it didn’t stop me from undoing my zip and taking my cock in my hand, giving it a good tugging as she looked on. She tried to look sultry and nonchalant, but she was hungry to be fucked. I could tell.

She lifted her top above her head and I grew solid at the sight of her perfect tits swelling over the top of her lilac satin and lace bra. The colour next to her olive skin had me ready to pop. She might be a stuck up, tragic little piece but, man, did she look hot and ready for a pumping in just her underwear and long hair draping over one shoulder. I so wanted to put my aching cock head in her nasty little mouth, but she refused. Instead, she stepped back and lay herself back on the bales and spread her legs wide, real wide, like she might split in half. Her briefs were such transparent lace that it was easy to see she was shaved. I walked towards her and went to mount her in the missionary position, ready to nail her to the hay, but she sat up suddenly and slobbered all over my face. I’m pretty sure she thought she was kissing me passionately, and by the sounds of her moans, it was obvious she was getting turned on. She clasped her hands tight around the back of my neck so I was unable to pull free. I figured the only way to distract myself from her inexperienced and over-lubricated tongue was to get on with it.

I wriggled my jeans lower and gave them a helping push downwards with both hands. I removed her tiny briefs and played with her cunt lips between my fingers for a few mere moments, more to check she was wet than to give her any real satisfaction. She was moist and ready, but as I tried to drill in, she was super tight. I’d have to go slow, which pissed me off a bit as that wasn’t how I wanted it to be. I just wanted to nail this little bitch, shoot my load, and be on my way. My bulging head was making her pant as I pushed slowly down. 

“Take it all, bitch,” I found myself saying, and in submissive response, she wrapped her legs around my back in an attempt to pull me in deeper. It didn’t happen at first, but after a few more thrusts, I was in, right up to my balls. My badass dick was planted deep in this little bitch’s pussy and it felt good. It wasn’t comfortable for my knees, they scraped at the hay underneath, and I didn’t have the balance right or support I needed to prevent me from squashing her, so I had to sort of rest myself up on one arm. Still looking down at her screwed up, drunk little face contorting into a fast-approaching build to climax was enough to feel my dick pumping pretty much all by itself. Although I’d not thought it possible, her cunt tightened further around my dick and threw us both into a loud, sweaty, grunting orgasm, in unison.

It was over quickly and even though I had shot my load and she had a smile spread so wide, as if she’d received the ride of her life, I felt nothing apart from smug. I looked around in the hope I could get cleaned up somehow, but there was nothing, no outside tap on the side of the stable. I let my dick drip dry and got dressed quickly. Looking at my watch, I realised I only had fifteen minutes before Suzy’s lesson ended and I had to get back to wait for her.

I got back to the training field in good time to see Suzy gliding back up the hill, her steed still firmly under her control and moving at a gentle pace. As she got closer, I could see she looked pleased with herself. She looked pretty with her big, triumphant smile bringing a glow to her cheeks. I felt bad for thinking that this had been a more exciting day for both of us and wondering if riding days might not be so tedious from now on. Mrs. Pickering was by the horse’s side, walking with pride and seemingly impressed for once with Suzy’s achievements. All in all, it was turning out to be a great day. The sun was shining and I was figuring that Suzy and I could spend the afternoon in a local country pub, whiling away a few hours and perhaps enjoying a steak and ale pie before heading home for an early night in front of the TV. As they both neared with the horse, Mrs. Pickering was the first to speak. “Nathan, hi, was everything OK?” 

Unsure what she meant, I just stared awkwardly for what felt like a long time, but probably wasn’t. 

“The the barn? What was it?” Shit, now if I had been clever, I might have thought about an answer for this already. 

“Oh, it was Maria. She fell and she’s fine now, I think. Nothing to worry about.” Thankfully, she appeared to have bought it. “

Nathan, I’ve had an idea,” Suzy stepped in, relieving the strange atmosphere which may have only been felt by me, but it was still tense, all the same. “If you could ride, too, we could ride together and it would save you the boredom of standing around...won’t you please consider it? We could take a couple of horses through the fields together and...well it would just be really great for me, please?” 

Suzy and I had had this conversation before countless times, but this time I caved. She looked so sweet right now and I was beginning to feel like a bit of a jerk that, in my twisted mind, I felt I could redeem myself by giving her something back. 

“Ok lets do it,” I said. 


"Yes, really”. Suzy squealed with delight in such a childlike manner I felt like I had betrayed the trust of someone who depended on me to look after her. 

“Why don’t you have your introduction session now?” Came Mrs. Pickering’s voice from behind us, “I’ve no one else booked in. We can get you up to speed and ready to ride with Suzy next week. She’s not too far ahead of you that you won’t catch up, haha!” Man she was nasty. But my Suzy did not rise to it. 

“You know what, babe, it is actually a fantastic idea. I’ll go home, change, do the food shopping, and pick you up in a couple of hours?”

If you could have seen her naive, unadulterated little eyes at this moment, you would have given her anything she wanted, just as I did. I agreed to stay on and at least have a look round and get signed up, but as soon as I watched Suzy head towards the car, I began to feel uneasy. I can’t tell you why but something deep in my gut didn’t feel right.

“Come on then,” Mrs Pickering barked, making me jump a foot high from my own skin and waking me from my anxious state. Without looking back to check I was following, she turned on her heels and walked ahead towards her office in the building at the entrance to the stables. Like a pathetic little puppy dog, I followed obediently, wondering how on earth she had managed to keep her boots so shiny and immaculate looking whilst being out teaching my Suzy.

Walking into her office, the uneasy feeling returned, and yet I still couldn’t explain why. I took a seat as she began to rifle through her filing cabinet for what I assumed were papers to sign. Instead, she pulled out a bottle of whisky and two glasses. “I think you and I need to have a little chat,” she said. 

“What about?” I replied feebly. It had already been a quite confusing yet exciting morning and I was starting to feel a headache coming on from the merlot I had knocked back with Maria, and the beginnings of a bad conscience from lying to Suzy. 

“I want to show you what I know from this morning. While Suzy was doing such a fine job of practising her trot, I had the chance to pop back here and check the security cameras to make sure everything was OK in the barn." From sitting in her huge leather bound chair she motioned her PC around to face me.

With horror, I stared at the footage appearing on the small computer screen before me. She had the whole thing on tape and was now smiling in front of me with such control I felt terrified at what she might be capable of. If she called the police, I could lose my job as a youth worker. I hardly think I would be seen as a respectable, trustworthy man of authority with a responsibility for the welfare of teenagers after this. My poor girlfriend, Suzy. I had been such a fool. She would never forgive me. In a stern, deep voice, Mrs. Pickering addressed me. 

“It would appear you find my daughter irresistible.” She looked me deep in the eyes. 

“No, Mrs. Pickering. I mean yes, oh look, I really don’t know what came over me. I went there to see if she was in danger, but she wasn’t. Far from it. In fact, she was upset, and drunk. Not that I took advantage, I mean, but she needed comforting, then she seduced me, as you can see. Oh it was a terrible, terrible mistake..."  I trailed off with my pathetic excuses with little left to say except “Are you going to tell the police?” 

“Oh, far from it, sweet boy,” she replied. This was one scary woman. She wasn’t old—perhaps 50 at worst, but she was an authoritarian; a lady of power, married to the richest man in the village, and a force to be reckoned with. Her hair was jet black and severely tied back into an old-fashioned bun. She had pale skin and cheekbones which could carve ice, and her lips were blood red, with long talon nails to match. She looked terrifying in a floor length leather black coat and spike heels attached to boots of a length I could not decipher due to being masked behind the coat. She had the tiniest figure, with narrow shoulders and small breasts. So slim was she, I mused that it may be possible to remove the coat to reveal nothing but a skeleton. But she was fierce looking alright, and right now, she had me backed into an uncomfortable corner with no way out.

“What I want to know is why would a handsome boy like you go for such a young, naive, pathetic specimen like her?” I could barely believe my ears and felt a huge overwhelming urge to protect Maria. 

“Mrs Pickering, with all due respect, that is your daughter. Why would you speak about her in such a way?” 

With one eyebrow slightly arched, Mrs Pickering leaned in close and calmly and slowly said, “That girl is trouble.”

“Even so," I continued, as I started to feel a real dislike for this nasty woman who could speak so vile of her own flesh and blood, “How you can be so wicked about your own...” 

“DAUGHTER?” she barked interruptedly. “You have no idea. If you do not want me to call the police, sweet boy, you are going to have to cooperate. I need pleasing,” she said as she began to unbutton the long vampiresque cloak which adorned her tiny body. 

Once every button was slowly unbuttoned, she gradually let the leather slide over the back of her shoulders, lower down her arms, and drop gently onto the desk behind her. Her eyes stayed fixed on mine the whole time as she lifted herself up to perch her minute bottom on the edge of the desk and slowly spread her legs wide. I was surprised to see her virtually naked underneath except for black bra, briefs of lace, and a heavy looking black and red leather boned underbust corset. The length of her boots were now not a mystery. They reached the middle of her thighs, and the closeness of the leather to her skin turned my cock to rock. 

“Now, boy, it would please me greatly if you would come and rest yourself on your knees in front of my little cunt. I want to look down upon you while you taste and smell a real woman, and you must convince me, boy that you are keen to learn the art of serving your mistress." 

I don’t know what it was about this woman, but I actually wanted to do whatever she said with an overwhelming desire to impress her. I needed her approval, even under her cruel bribe. I was scared of her and the way she called me boy. Her lust for young men half her age both unnerved and excited me. It was hard to imagine anyone had ever refused orders from her, and it was that kind of power which I was finding intoxicating.

I somehow motioned myself across the room in a trance-like state. I felt lustful, tinged with a real fear of not hitting the mark. I had never had my abilities questioned before and felt that I was about to be put to a test I would not pass. Even so, I wanted to so badly. This nasty, controlling, vile woman had me completely at her mercy, and yet it didn’t insult me in the same way that Maria’s arrogance had repelled me. Mrs. Pickering deserved respect, somehow. She was perfectly groomed to the finer details, each nail painted with precision, her strong make-up immaculate. She smelt good too; a heavy musky scent which had to be something expensive. Unlike Maria, she wouldn’t buckle under my touch and I felt it may be my turn to lose it under pressure.

I found myself at a foot distance from her, unsure of what to do with myself. I felt like such a useless lump. Where had my entire big guy attitude gone? Instead, I felt exactly like the boy she wanted me to be; foolish and awkward and awaiting instruction. I looked into her eyes for some kind of guidance, but she just stared back with a calm expression and a cold nondescript half-smile, which gave away nothing. Eventually her smile turned to mild annoyance. 

“What is it boy? Are you not attracted to me?” 

“Oh no, it’s not that, not at all. I mean, you’re sexy, beautiful.....” I sounded like such a loser. 

“Then come closer, my boy. Show me your love for me, your need to serve me." She closed her eyes and leaned her head back, as if waiting for something amazing to happen. I knelt down and took a hold of one of her leather clad ankles, feeling the cold material against my palm. I lifted her leg over my shoulder so her knee was against my face and with my other hand, I began to massage, stroke, and squeeze her thigh. 

“Oh yes, boy, that is a good start, oh, use those hands, boy. Serve me, impress me,” Her encouragement turned me into a grateful slave. The more she praised me, the harder I tried. I ran my tongue along the underside of the top of her boot, which seemed to send her wild. 

“Again, boy. Use me, devour me.” 

I felt like my cock had taken on a whole new form of solidity, desperate to drill this woman. This was a whole new experience of lust. I could think of nothing but needing to make her wild, make her want me, feel my drill, make her come. I was terrified I might lose my load in my pants. She was so hot and still leaning back, putting all of her trust into me to provide her with pleasure. She was giving me the control, and yet I was completely at her mercy. I threw her other leg over my other shoulder, turning my head from side to side to nibble both of her tight, sculpted thighs while feeling the cold leather encased around my neck. Her heels began to press into my lower back as she became more turned on. 

“Oh, you are good boy, you are so very good at looking after your mistress...oh god yes...Mistress is so pleased with your progress.” 

I became hungrier with every word I received from her, so grateful of her praise. I began to bite her thighs a little harder which was met with equal appreciation. 

“Yes, boy, yes...oh yes,” She began to sway her head a little and I was convinced that she was edging her cunt closer towards my face. I began to nibble the outer lace of her panties. They were wet. I pulled the material into my mouth and sucked the juice from them. I pulled them to one side with my hand and licked her outer cunt lips with the flat of my tongue. 

“Oh...mmmmm...yes, boy, yes, oh yes.” She was definitely edging closer, I had no doubt in my mind of that now. I buried my face completely inside her, sucking her lips and probing hard and deep with my tongue, pulling her sweet cunt wide with my fingers. I motioned one hand away and began rubbing the skin above her clit in furious little circles. This always drove Suzy crazy and was now having the same unstoppable effect on Mrs. Pickering. 

“Oh boy, you must slow down, no, stop, oh, oh, oh...”

For the first time, I was ignoring her instruction. While worrying what the repercussions might bring, I was unable to resist the temptation to increase the tremor in her legs, heighten the moans from her mouth and swallow the juices now running freely from her cunt. Like a feeding puppy, I lapped, nibbled, and drank hard until her whole body convulsed and her vocals became loud and heavy. Her legs locked hard around me and tensed for a few moments, then relaxed, and I heard her sigh deeply.

It was quiet for a moment and then she spoke. “Oh, my dear boy, you didn’t obey your mistress. You were unable to control your juvenile lust. What am I going to do with you?” I felt completely strange. I was scared of her, yet fully erect in my pants. I stood and watched in slow motion as she arose from the desk and dressed herself slowly back into the long coat, staring at me while doing up each button. She glanced down at my fully hard dick pointing from within my jeans and began to laugh. “It looks like you are going to need some training, my boy. You will come back each week and we will send your young sap away when your riding sessions are finished so we can continue your lessons in here.”

It became apparent to me then that this was not over. She did not want to rid me of my job or destroy my relationship with Suzy. No, in fact, what she wanted could be worse, because now she had me as her slave, forever in her debt.

As I walked out into the fresh air, I was just in time to see my Suzy driving up towards me. She was smiling, obviously still happy at my consent to join her in riding here each weekend. She slowed down to a complete stop by my side and I climbed in. The drive home was surreal. She gabbled away about a trolley war she had with an old lady in the supermarket and laughed at how she had been asked for ID for cigarettes. All the while, I was just concentrating on not saying something stupid and praying that I didn’t smell of pussy.

Read next: Fantasy
Ava Sheridon
Ava Sheridon

Professional Dominatrix in the south east. Writer of real life and erotic fiction.

Passionate about food, ethical living, zero waste, mental health, helping others, singing, reading, running, music, alternative therapies, crystal healing.

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Learning to Ride
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