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."
