Lessons Whilst Riding

This happened in the 1990's and is based on my own experience.

It was mid-June; I had just turned 19 and had recently completed my A levels at school from which we'd been allowed to do our own thing until the end of term. I was at a UK boarding school which suited my parents as my father's work took him all over the world, changing location nearly every year so boarding offered some stability to me. I can't say I loved it, it wasn't exactly Hogwarts, but I did have fun and over the 5 years I'd been there I had formed some great friendships.

One such friendship was with Andy, one of 8 Andy's in my year, so he was more commonly known as Tiny as he was tiny. The other Andy's all went by their nicknames rather than 'Andy'. Tiny's mum and dad were the landed gentry types, very down to earth and had agreed to let Tiny bring 3 friends over to their stately pile in Oxfordshire where, in return for helping around the estate, we got paid, a bedroom, fed and watered whilst worked there.

The invite was indefinite, and I was going to see how things went, possibly staying until mid-August when my family planned to go away. I was good around horses, so I volunteered to help there whilst the other 3 ended up working around the farm. By the end of the first week, we had all developed a good tan from being outside all day and we'd all leaned down or built-up muscle due to the labour we were putting in.

For my part, 'work' included mucking out the stables, moving hay bales, riding the 3 horses they had and then helping the other 3 lads if I was having a light day. Tiny's sisters were still away at school, so it was only his mum riding so, more of often than not, we'd ride out together twice a day, working all 4 horses in rotation.

I had no idea how old Tiny's mum was nor what her name was; she was Tiny's mum or Mrs X to me. Like Tiny she was petite, probably 5 ft 4, and looked stunning in her riding gear of jodhpurs, leather boots and a tight-fitting polo shirt with her long dark hair in a plat. I'd hazard a guess she was past 40 but the gym classes, riding and carefree lifestyle meant she was fit, toned and tanned, looking much younger than she probably was.

It was early on a sunny Monday morning and I was riding out with Mrs X, across the fields taking in the stunning view of the rolling countryside with pockets of mist lingering in the dips. The other view I was taking in was that of Mrs X's athletic bum bouncing up and down as she galloped ahead of me. Being an all-boys boarding school I was still a virgin, my only experiences with women being limited to the odd fumble or kiss at some events our school arranged with neighbouring all-girl schools. Seeing Mrs X's delicious rear bounce up and down in front me was all my lively imagination needed and, before long, I was uncomfortably hard with my cock pushing down the leg of my own jodhpurs. I'm reasonably well endowed but the dark blue of my jodhpurs meant it wasn't too obvious.

Mrs X decided she wanted to practice jumping a few low hedges, so we took a different route today, one that followed a stream and then took in a wood. I saw the hedge Mrs X was going for and decided it was too ambitious for me and the horse I had so I directed my horse to jump the nearby gate. I didn't see what happened, but I certainly heard her fall, curse loudly then shout me for help.

"Tom, oh fuck, I've really hurt myself."

Her horse was nearby so I tied both horses up before running over to see how she was. She didn't appear to be broken as I approached her, but I could see she was picking brambles from her arm.

"Are you OK," I asked as I knelt down near her.

"I think so. I'm covered in nettle stings and these bloody brambles. Can you check I'm not cut badly Tom?"

"Sure."

I picked the remaining brambles off her shoulders and back and had a look at where she'd torn her top, inspecting the cuts. Her legs looked ok, a bit soiled where she'd landed on her bum but otherwise OK.

"Your top is ruined, there's a massive tear up the back, but your skin looks fine, just scratched. Your bottom half looks ok, I guess we'll see how you are when you stand up."

"Thanks Tom, will you help me up so I can check my legs?"

I knelt down and put my right arm around her back and under her armpit, using my strength to help her stand up. During the movement upwards my arm worked through the tear in her polo shirt, ripping what was left of it apart so it was only held on by its arms. As she dusted herself off and tested her legs her polo shirt fell away revealing two pert breasts atop a tight torso. I didn't want to drop her, so I was still clinging on to her when I was caught like a rabbit in headlights looking down on this exquisite woman, naked from the trousers up.

Mrs X chose to preserve her decency by pressing her breasts into me as her shirt sides fell away, asking "Oh Tom, this is embarrassing. You'll have to stay here their whilst we figure out what to do."

"That's fine. You can have my shirt."

Whilst she was thinking through my offer my brain went in to overdrive and I could feel my prick start to grow, hoping that Mrs X didn't notice it pushing down between our legs which we pressed together.

She hadn't appeared to notice when she said, "That's very kind of you Tom and I'll think I'll accept your offer. I'm not sure the world wants to see me riding topless."

"I don't know about that Mrs X," I said, my brain managing to say what I was thinking much to my embarrassment. "I'm sorry Mrs X, that was rude of me."

"Tom don't worry. I'm flattered that a handsome young man thinks those things about me."

"I doubt you need me to tell you how stunning you look Mrs X, especially in your riding gear. You're clearly incredibly fit and... I'm sorry Mrs X, there goes my big mouth again. I'll give you my top so you can cover your modesty."

I stepped out of our embrace slightly and pulled my polo shirt off, moving towards Mrs X again to offer my shirt, my head pitched down to hide my embarrassment for speaking my mind. She took hold of the shirt and carried on closing the gap between us until her hand was on my chest, stroking my pecs lightly before moving her hand over my torso.

"You're quite the specimen Tom, handsome, muscled and a gentleman. I'd be lying if I said it hadn't given me a lift hearing you talk about me."

We were now pressed together such that my groin was pressed hard against her hip and, as her hand continued to explore my chest, my prick became rock hard. It was very intimate to be so close to a beautiful woman, to feel her breath on my face and neck, to smell her hair and to feel her warmth through her bare breasts as they touched my chest as she moved around.

"I should thank you for saving me Tom," she said, kissing me on the lips before I had chance to play down her statement of me saving her. Our kiss continued and now my tongue was involved in a duel with hers as she tossed my shirt to the floor and pulled my head down to hers. Our chests were now in full contact, and our groins pressed together as continued kissing and stroking each other. I kept my hands on her back and bum, thinking that was my safe limit, only for me to be shocked when she stuck her hand down my jodhpurs to grab my cock.

"Is that because of me?" She asked.

"It is Mrs X. You're very beautiful."

"You can touch me too Tom, if you'd like to."

I started by cupping one of her breasts with my right hand, my left staying on her firm buttock pulling us close so I could push my cock in to her hand that was now coiled around it. I could feel myself getting more and more excited, my senses overrun as I played with her lovely tits. I wanted to take full advantage on her offer to 'touch her' and, given she was wanking me gently, I followed suit and tried to push my hand down the front of her jodhpurs, but they were too tight.

"They zip on the side," which confirmed to me that I was granted full access.

I unzipped her then pushed her jodhpurs down to her knees, and then did the same to a g string she wore, leaving her standing in my arms bare chested and with her pussy and arse fully exposed.

I soon learnt that Mrs X had a bald, juicy pussy and that I'd correctly taken in where a woman's clit is from the chats at school. Mrs X seemed to be enjoying my gently fingering of her pussy as well as the strokes I gave her clit as she became increasingly wet down there. I felt my cock hit fresh air as she released the zip on my own trousers, pulling my cock towards her. So, there we were, in a wooded area wanking each other, a young man full of spunk and a middle-aged beauty brought together by a happy twist of fate.

"I'm pretty sure no one would her me Tom if I told you not to fuck me, hard, as you bent me over that fallen tree. I doubt they'd hear me as I screamed, ever so quietly, as you continued to cum then fuck me again and again. You could probably do anything you wanted to me I'm so tiny compared to you."

"Are you sure Mrs X? I don't think I could stop if I started."

Mrs X was holding my prick and walking us both towards the fallen tree, mumbling her funny little scene setter as we did so, "Tom, please don't, I'm so weak. I can't fight you and you are too big for my little pussy. Please don't fuck me Tom."

I watched as Mrs X kicked off her boots so she could fully remove her trousers which she then draped over the large tree truck that lay near us. She then bent herself over the trunk, opening herself into a wide stance before looking back at me and saying, "Please Tom."

I pushed my trousers down and then lifted her right leg up as I crouched down behind her bum. I kissed her ass checks before pushing my tongue between her legs, determined to taste her pussy, trying to tick off all the things I'd dreamed of in the past. She tasted amazing and I was clearly doing ok as her hand was soon grabbing my hair and pulling me in to her firmly as I flicked, licked and dabbed at her lips and clit, feeling how wet she now was.

"Oh god Tom, I'm cumming," was nearly enough to make my throbbing cock release its spunk on to the ground but I let the feeling pass as continued to tongue her through her climax. As she squirmed my tongue found her asshole through which I pressed my tongue which prompted another exclamation of, "Oh Tom, no one has even licked me there. Oh lord, that's amazing. Oh yes, please, more."

I had both my hands on her buttocks now, pulling them apart so I could see both her bum hole and pussy as I worshipped them with my mouth and tongue. I felt primal, feasting on this beautiful woman, as my hard cock touched the plants growing around the tree trunk as I crouched down. As Mrs X trembled through another climax, shouting "fuck me that was incredible," I decided I needed to do just that, fuck her, before I shoot my load on to the ground.

Pulling her leg up again I pointed my cock head on to her pussy lips, no hands needed to guide it I was that hard and pushed the head inside. Biting hard to stop myself cumming as I lost my virginity, I started pushing myself further and further into Mrs X.

"Oh God Tom, that feels amazing. So tight."

I couldn't talk and I was sweating now as I fought the urge to cum. In reality I think I managed 5 or 6 hard thrusts before I started cumming, harder than I ever have in my life. I didn't count how many times I ejaculated but it seemed to last forever as I pumped in to her each time I pulsed cum out. Once I finished cumming I stayed fully sheathed in Mrs X, my pubes pushed up against her asshole and my cock, still hard, throbbing and feeling the warm cum dribbling around us both.

"I felt every jet Tom. That was lovely. And you're still hard."

I leant in and kissed her neck and then cupped her breast as I started to fuck her again.

"Oh my, that's nice Tom."

I wanted to last longer this time so I could focus on experiencing all the amazing sensations I was experiencing. Her nipples were very hard as I played with them, concentrating on that for while in an attempt to distract myself from the feeling of her tight pussy stretched around me. I took a look down between us and nearly came when I saw my angry red cock withdraw, covered at the base in a white sticky mess. I pulled my cock fully out to see her pussy gaping wide open and dribbling slightly with my cum on the sides of her pussy lips. I thrust back in, eliciting a groan of approval as I pushed all of my cock in with one thrust.

"This is so good Tom. Keep fucking me, try and make me cum again if you can."

I knew I wasn't going to last forever so, if I was to meet this challenge, I needed to encourage her on. So, I reached round with my left hand so I could rub her clit whilst I pumped myself into her, driving with more vigour now as I relished the sight of her buttocks rippling slightly as I hammered myself home.

"That's it Tom, keep doing that. Oh god."

I was watching her bum intently now, the rippling buttock and her wet asshole, wishing my brain to capture and remember this scene forever. I must have been salivating at the sight before me as the next thing I noticed I was dribbling spit down on to her asshole.

"Oh Tom, that feels naughty," she said as my spit hit her squarely on her slightly open bum hole.

Using my thumb to push my spit around her anus made Mrs X groan deeply and I felt her tighten around me and cum as I pushed by thumb all the way up inside of her ass. She was bucking her ass back on to my thumb and her pussy on to my cock, moaning into her arm as she came hard.

I pulled out of her then turned her around so she was sat on the trunk, pulled her legs aside my waist as I thrust myself into her, cumming almost as I kissed her, my cock pumping her full of my cum again as I French kissed her.

Mrs X cupped my face in her hands as I continued to plough into her, slowing steadily as my climax faded away. I was still hard, amazingly, as I remained inside her as we made out.

"Tom, that was very special. Thank you."

"I don't think I'm finished yet Mrs X."

"Really Tom?"

"I'm still hard and you feel amazing."

"I'm going to get sore Tom if you keep fucking my pussy."

"That's a shame."

"I'm sorry Tom. We could try something else though."

"What did you have in mind Mrs X?" I asked, thinking a blow job would be another thing ticked off the bucket list.

"I was thinking I'd get you nice and wet and then let's see where else we can squeeze this delightful prick of yours."

Mrs X then got to her knees and took a good portion of my cock into her mouth, sucking me as she bobbed her head up and down my shaft. I'd never had a blowjob in my life before and, honestly, was now fighting to decide which felt better, pussy or mouth. The way Mrs X looked up at me as she sucked me was very erotic and I think she could tell I was spellbound as she started to show off her skills. She pushed me all the way into her throat until her eyes watered and then she used her tongue to tickle what we called our 'banjo string' at school (frenulum), her eyes willing me to cum as her tongue almost beckoned my climax to appear. It didn't, thankfully. I was achingly hard; the benefit of youth coupled with the pure eroticism of the situation I was now in.

Mrs X then pushed my cock between her boobs, squeezing them together around my cock so I could start fucking them. She was sucking or licking the head of my cock as it thrust through her tits. This looked great and was exciting but it wasn't a patch on fucking her mouth or pussy. I pulled her up, so we are face to face again. I kissed her, deeply, then looked her in the eye, "I'm going to fuck you again Mrs X, I've got to."

Seemingly resigned to her fate Mrs X grabbed her jodhpurs, tossed them to the ground with our other clothes. I was expecting her to lie down on them, but she surprised me when she got in to a 'doggy' position. I became super hard when I watched as she spat on her fingers then smeared the spit all around her arsehole, pushing in two fingers to the second knuckle, working her spit in to her tight anus.

"Spit on your knob Tom and, please, go steady."

She didn't need to tell me but the gravity of what was being offered to me hit me. I was going to fuck Mrs X's arse. Anal sex was probably the act most surrounded with mystique in our fanciful chats as boys at school. Claims by some to have had sex were generally accepted but anal sex was something none of us thought we'd ever have the chance of trying unless we found some strumpet with a huge sex drive.

I was about to have the third fuck of my life, all on the same day, and with the same amazing woman, my best mates mum, who was now pulling her buttocks apart to make her anus easier to penetrate.

I did as instructed and smeared my knob with a dollop of spit then pressed it on to her anus. Time slowed down as I tried to squeeze the hard head through her tiny ring, all whilst trying not to cum. Nothing was happening so I spat another load on to my knob and started pushing again on her backdoor. And then it happened, my entire cock head pushed through, Mrs X screeched "stop Tom, hold still," and I froze with my cock throbbing powerfully as Mrs X's ring tightly gripped me, slowing down the blood supply, causing the head to swell and throb. I was looking intently at the vision of my cock sticking into her very tight anus when my eyes caught Mrs X looking back at me, her slightly pained visage turning to a warm smile as she appreciated the intensity of this experience for me.

"Thank you, Tom. I needed to get used to you. Keep it moist with your spit, go slowly and," she smiled deeply as she said, "enjoy my tiny ass Tom."

I was shaking once I got fully inside her bum, shaking with a mixture of incredulity and the sheer magnitude of the experience. Mrs X's anus was so tight I had to work hard to push myself in and out which in turn caused sensations I'd not yet experienced to develop that took every ounce of willpower not to succumb to.

"Grab my hair Tom," I was instructed. I complied and then pulled her head towards me as I pumped her arse with my cock.

"That's it Tom. Show me who's boss. Ride me."

I took that last instruction literally and moved so I was crouched over her bum, rather than kneeling behind her. I was using my thighs to support myself and the ache they produced was a slight distraction from the pleasure.

"Harder Tom. Cum in my ass."

I felt like a stallion now, trying to breed my mare, pulling on her mane as I claimed Mrs X's anus.

"Please Tom, I'm nearly there."

I noticed that Mrs X had been fiddling with her clit whilst I was fucking her arse. I'd mistakenly thought she was giving me her ass for my pleasure only. I was wrong. This made me feel wronged. I slapped her bum subconsciously.

"Oh yes Tom, spank my arse."

Whack.

"Oh god, harder. Make it red Tom."

Whack, whack.

"Harder Tom."

I reached for the riding crop in the pile of cloths. "Should I?", I asked myself.

"Tom, spank me harder, please." She shouted.

Thwack, the riding crop made a bright, sharp crack as it found its mark on her buttock.

"FUCK. TOM. AGAIN."

I started cumming as I rained down 3 or 4 more passes of the crop which seemed to be all Mrs X needed to send her it to a climax so strong it looked like she was having a fit, my cocks spewing load after load into her bowels as she twitched and rolled about. Her movements eventually caused my cock to pull out of her arse, the final two ropes of cum splashing on to her back.

Mrs X was still moaning, in a good way, moments later as I looked at my cum dribbling out of her bum as I stroked her back. I'd gone soft now and the moment was starting to dawn on me as I looked at her beautiful form covered in the evidence of our union... my cum, her wet pussy, her red bum crossed with a few faint lines, my cum rolling out of her ass and then a glug of cum from her pussy, evidence of the two loads I'd pumped up there earlier.

Spanking a woman hadn't been on my bucket list so I was very surprised by the effect it had on me. That moment was probably the genesis of a lifelong love of it, something I am now keen only to do for the willing and where it enhances the experience of both. I used my finger to trace one of red lines the riding crop had made on Mrs X's bum, and then another line. I must have looked concerned as Mrs X spoke reassuringly, "I loved it Tom. I asked you to do it. And Tom," she asked me.

"Yes, Mrs X?"

"We will be doing this a lot whilst you are here. Is that, OK?"

"You mean the fucking?"

"I mean the fucking, the kissing, the licking and also the spanking. Is that, OK?"

"My father told me to do as I'm told here Mrs X." I said as I smiled on at her.

"Very good. I think it's a good job I fell off my horse as it's going to make explaining these marks a lot easier, if he even notices them."

~

And that event marked the abrupt end of my innocence, and what followed, until I started at University (I declined the chance of joining the family holiday) in September, was a summer being coached by Mrs X in the art of love making.