It was a warm sunny Sunday afternoon heading into evening when I was out of a bike ride, maybe 50 miles from home and then the chain broke. I started to walk to the nearest station hoping to make the last train home, but it was miles away and, being a Sunday, I didn’t have much time.
After walking for maybe 30 minutes, which is not easy in cycling shoes, I heard the clip-clop of a horse approaching from behind. A turn to see a woman approaching on horse back. She’s wearing knee high black leather riding boots and white jodhpurs – oh my she has terrific thighs. My eyes move up to her navy polo shirt and onto her head, with long red, slightly greying hair neatly tied up under her riding helmet. Our eyes meet and her wry smile tells me she knows I’ve just checked her out. I feel my face turn red as she exaggeratedly returns the favour. My lycra shorts and top leaving little to the imagination. She must be about 20 years older than me, maybe mid 40s.
“Hi there, are you ok?” she asks in a cut-glass English accent. I explain about my bike and after she tells me there’s no way I’ll make the train on foot, I accept the offer of a ride, leaving my bike behind a hedge, to be collected later. “Have you ridden before, or would you like a leg hand getting up?” she asks. “Umm I think a hand up might be good – I haven’t been on a horse since I was about 5”. She dismounts and I can now see just how tall she is – a good few inches taller than me, probably getting on for 6′. She guides my left foot into the stirrup and before I know it, her hands are firmly on my butt. “Very good – on three… one… two… three”. She pushes and I find myself sitting on the saddle. “Slide back and I’ll come up in front of you” she commands and I soon find myself staring at her pert round bum before she lowers herself onto the saddle, pushing back against me.
“Ready to go?” she asks, but doesn’t wait for a response as the horse jerks into motion. I feel myself falling backwards – I reach out to stop my fall, grabbing the first things that come to hand – her tits. She gives me a sharp, but gentle tap on the butt with her riding crop “Hey! I don’t even know your name”. Once I’ve steadied myself I move my hands from her perky B-cups to her hips “I’m so sorry – I though I was going to fall. I’m Mike – I hope you can forgive me.” She looks back over her shoulder and grins “Don’t worry about it Mike. I’m Alice.”
We ride on across the fields, the sun getting lower in the sky and the shadows getting longer. I hold myself firmly against Alice’s hard body as we move together, following the horses motion. My arousal has been growing since the moment I set eyes on Alice and a full on boner is soon sandwiched between us, pressing firmly against the small of Alice’s back. Alice stands in the saddle for a moment and then wiggles her butt against my cock. “Glad you’re enjoying the ride Mike” she says with a giggle. “Umm yeah, sorry about that” I reply as I feel myself going bright red. She looks over her shoulder, sees that I’m bright red and grins “I’m not sure many men would be embarrassed about the size of that”, she pushes back once more.
We ride on, Alice giggling like a teenage girl as she deliberately wiggles her butt against my cock as she pleases. She then takes my left had and places it on her left tit. I’m not sure what’s going on, but I find her nipple rock hard as I start to have a better feel than before. I then find my right hand being moved too – she very deliberately tucks my fingers into the waistband of her jodhpurs. My heart is pounding in my chest, but I hesitate for some reason. Alice chastises me “Don’t be such a prude – Mike. Come on” and gives me another tap with her riding crop. I need no more encouragement and start to delve deeper. I soon realise she’s commando and my fingers follow her neatly trimmed pubic hair down to her dripping wet slit. I slip two fingers and get to work on her clit. Alice’s breathing quickens and she’s soon moaning gently.
I carry on working away until I feel a sharp shove to my side and find myself flying off the horse. I get a soft landing in a haystack and look up to see Alice looking down at me grinning. She jumps down to join me, immediately discarding her riding helmet before lifting off her polo shirt and getting to work on her bra. I kick off my shoes and start to strip off my cycling kit, checking out her toned torso as I do so. “Would you mind?” Alice asks holding out one of her shinny black leather riding boots, which I eagerly slip off. Once the other is also off, she unbuttons her jodhpurs right in front of me, clearly putting on a bit of a show as she peels them off. I’m mesmerised by her as I take in her fiery red landing strip and her gorgeous legs.
She stands naked before me for a few seconds, letting me take her in. She then steps forward and pushes me back into the hay. I’m soon looking up at her straddling me as she reaches behind as she guides my cock to her pussy. She takes my length in one and then starts to ride me, forcing me down into the hay with her superior strength. She knows what she’s doing and keeps me going as long as I can, backing me off when needed, but it’s not long before I lose it and fill her pussy with my spunk. She slides my cock out of her before moving up to my head – I’m soon looking up at the cream pie I just made as she lowers herself onto my face. I start to work her clit with my tongue, lapping up the mix of her juices and my spunk that’s covering my face and filling my mouth. I listen to her moaning increase as she sits on my face and grinds away against my tongue. It’s not long before she comes, her whole body tensing as the orgasm rips through it.
We lay in the hay for a few minutes, exhausted and watching the sun start to set. Alice tells me to get dressed as she starts to pull her jodhpurs back on. We’re soon back on the horse and making our way to Alice’s, which she tells me is not far away. A few minutes later we turn onto a long, tree-lined driveway leading down to a huge mansion. “Holy shit – is that yours?” I enquire and Alice confirms it is.
Alice heads around the back of the house to a stable block. She jumps down from the horse. She goes into the stables and emerges with the stable boy who holds the horse as she helps me down. “Johnson will take you up to the shower” Alice tells me as she leads the horse into the stables. Johnson leads me up through the back entrance to the house and into a huge bedroom, with panoramic views down the driveway and formal gardens. He shows me to the ensuite and tells me to put my cycling kit down the laundry chute.
Once done in the shower, I lay out naked on the bed, somewhat surprised to be sharing with a teddy bear, and wait for Alice to come and play, but end up dozing off to sleep as the sun finally drops below the horizon.
I wake up to a blowjob – my cock fully hard and being teased by a tongue. I lay back and enjoy it for a few moments before opening my eyes to find the room dimly lit and view dominated by thighs, butt cheeks and a freshly shaven pussy. I reach out, grasping her hips as I push my face between her legs. I slip my tongue into the super smooth pussy and start licking away, which elicits an almost girly moan. She sits back a little as I start to work away at her clit. She briefly sits forward and I comment “Alice you’re so smooth”. She climbs off me and after a moment of confusion I find myself looking at Alice’s teenage daughter. She’s every bit as elegant as her mother, but a touch more slender. “Shit, she didn’t tell you did she? I’m so sorry – you’re Mike, right? I’m Verity”. She hold our her hand, which seems a little weird, but I shake it none the less. “Umm nice to meet you. What did’t Alice… your Mum not tell me?” I enquire. “Oh just that you’re mine for the night” she replies. She smirks and then straddles my head and prepares to sit on my face, just like her mum had done a few hours earlier. I smile then immediately start lapping away at her smooth pussy lips.
Verity’s breathing starts to quicken and before long she’s moaning loudly. She keeps grinding away against my face for a little longer. She then gets off and I look across getting onto her hands and knees – she’s soon face-down, ass-up, looking back at me with a grin on her face. I move in behind her and slide my length into her tight slit in one go, which yields a loud squeal of delight. I start to fuck her slowly and gently. I keep going, thrusting in deeply as Verity pushes back.
“You don’t need to be so gentle Mike – she’s young, but she’s as strong as an ox”. I look across to see Alice standing by the bed wearing a short black silk robe. How long has she been watching from the shadows I wonder. I start to pound Verity harder, but Alice is not satisfied, “I know you can go harder than that Mike”. She then strikes me firmly on the ass with her riding crop. It stings like hell and I look across at Alice just as she strikes me again “Harder Mike, just like earlier”. I start to thrust as hard as I can to avoid another strike. Verity takes it well, moaning loudly each time I slam into her, but she doesn’t last too long and collapses onto the bed as she orgasms. I keep going for a the few seconds I need tip myself over the edge.
“Well done Mike” Alice says as she pats me on the arse and struts out of the room.
Source: reddit.com/r/sexystories/comments/dd4ijg/cougarmilfolderfmf_one_hell_of_a_ride
Good story, next chapter?