Sandra Ottershaw Ponygirl 314 Ch. 01

Story Info
Summer ends for a young Ponygirl on a Cornish Island.
6.3k words
4.18
50.3k
4
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The scene, a small island among the stunningly beautiful Isles of Scilly in the Atlantic Ocean off the southwest tip of the Uk, its two thirty on a warm sunny afternoon with just enough breeze to send the waves crashing against the shore and Sandra, Ponygirl 314 stands patiently admiring the view as she awaits the arrival of the afternoon boat from the mainland.

=================================

"It's funny how you get stuck in a rut," Andy mused as the speedboat slammed into yet another wave sending the engine revs screaming, as they hurtled along leaving a foaming white wake across the azure sea stretching between the islands, islets and jagged rocks that flanked the approach to the island's tiny harbour.

"What's that sir?" Jake asked as he expertly swung the wheel sending the boat arrow straight through the gap between the rows of jagged granite rocks and away from the sandy beach and towards the old stone jetty.

Jake throttled the twin outboards back to a burbling idle and Andy looked across and grinned, "Nothing," he said with a grin, "Just saying how quickly you get used to all this."

"Couple more weeks sir," Jake said, "Season ends in October, then its back shoreside."

"Not going to South Africa?" Andy asked knowing the company freighter was due in just over a fortnight to move the whole operation down to near Capetown for the winter sun breaks the brits so loved.

"No, Pantomime in Blackpool for me," Jake replied, "Too hot in Africa."

The speedboat approached the Jetty which towered twenty feet and more above them as they wallowed in the slack water at the bottom of the tide, "It's slippery sir," Jake warned, "I could beach her on the sand if you prefer.

Andy surveyed the slippery worn granite steps, he wasn't as fit as he used to be, a few years before he had nearly been an Olympic standard rower, but that was at University and now at thirty two he had become risk averse.

"Yes, if you wouldn't mind," Andy agreed, "I'll square it with HQ if we can't get you off."

The motors howled to life again and Jake swung the sleek blue and white craft back though the rocks and around towards the beach before crashing through the surf to slide gracefully to a halt on the firm wet sand beyond.

"We've been spotted." Jake advised and he pointed to the beach edge where grass covered sand dunes defined the break between sea and the rocks beyond, a cart was approaching, no two carts, a woman in Jodhpurs and hacking jacket driving one and leading the other.

Andy stepped off the bows and jumped down onto the firm sand and slipped off the waterproofs before he took his backpack and briefcase from Jake and thanked him for the "Smooth" trip and then turned to watch the approaching cart.

The lead pony was well trained he decided, her thighs geometrically level as she high stepped down the beach, one of the older ponygirls he noted, twenty seven maybe? her skin aged prematurely from the constant exposure to sun and salty sea breezes, her scalp bronzed where the hair had been shaved to leave just the centre strip that became her mane and flowed down through a ring where the straps of her bridle.joined at the back of her head.

Sweat glistened on her naked breasts thrust up as always by the tight black corset and her crotch belt glistened wetly betraying the fact she had a dildo in place warming her up in case Andy chose to use her.

Her long latex hoof boots looked new and he saw she held the carts shafts in her hands, rigid spreaders keeping her wrists and elbows in place behind her back instead of the clincher many pony girls used.

"Jen," How are you?" Andy shouted to the woman in the jacket and jodhpurs.

"Going crazy of course, its ok for you back in Penzance." she said.

"London three days last week," he said, "Not all cider and pasties."

"No, it's a hard life, how's the Ferrari?" she asked.

"Still poorly, needs a cam belt whatever that is, eight thousand pounds." he admitted.

"That's more than my whole car cost!" Jen replied, "But you're here now and Terry wanted you to see the storm damage on the south path before we talk about staff."

"Fair enough," He agreed, "You brought me Silver star I see."

"Yes, I remember you were full of praise for her last time." Jen agreed.

"And what exactly is that?" he asked and pointed to the pony following behind.

"Three fourteen," she said, "We just need your approval to terminate her contract."

"Why?" he asked.

"Do you need to ask?" Jen said, "She's hopeless."

"Good shape, isn't she a runner, I mean wasn't she a runner?" he asked.

"Was, she's just bad tempered, won't train, oh she really is a nightmare." Jen insisted.

"Oh well, in that case she can run me out to the point," And suggested, "Has she got a current certificate?"

"Somewhere," Jen agreed, "But I brought Silver for you, your favourite!"

"No STD certificate though?" he asked.

"No, no certificate but she has loads of condoms." Jen suggested.

"You know I'm a bareback kind of guy," Andy insisted, "If its OK I'll check out the south path and take 314."

"Your decision," Jen agreed, "But seriously, I can't really trust her with punters."

"I'll risk it," Andy agreed, and then he looked down, "Can you take my bags?"

"Of course," Jen agreed so he tossed the backpack in the cart and handed Jen the briefcase before he took 314's reins and led her across the sands clear of Silver Star so Jen could ride away.

"You hurt your foot?" he asked as he saw a small tear in 314s rather tatty leather left boot, 314 stamped once.

"Does it hurt?" he asked, she stamped once.

"Has it been looked at?" he asked, she stamped twice, "Ah," he exclaimed, "Lets have a look then." and he unbuckled the straps holding her boot.

"Oh god," he exclaimed, 314 tried to look down but the stiff high collar around her neck prevented her, "When did you last wash your feet?"

He stood up, "Just a bruise but," he looked at her face, tears welled deep behind her blinkers, "Just a bruise."

Her stare unnerved him, "Lets get the other boot off, maybe you can take a short cut along the beach?" he suggested, "Through the surf?"

She stamped her booted right foot, "Yes barefoot," he agreed and unbuckled her right boot and slipped it off her dirty foot.

"Shall we?" he suggested as he threw her boots in the back of the light weight cart and climbed aboard shifting around so the minimum weight tugged on her belt, as her arms were folded across her back in a clincher unlike Silver Star who had spreaders and could take some of the weight in her hands.

"Walk on," he suggested, but left the reins attached to her bridle loose, "Along the beach in the surf maybe?"

She moved tentatively at first, then she began to run across the soft warm sand and down towards the wet wave washed sand and the surf, Jake watched as he waited for the tide to lift the beached speedboat off the beach, and then they were splashing through the surf.

Andy suddenly realised there was a downside to rushing through the surf as the salt water splashed up off her feet and splattered over his expensive suit but as she seemed to be enjoying herself he let her continue, until she stumbled and fell head first into a foot of water, he jumped off the cart immediately to let her get up, but she stayed down.

"Hey, get up, get up," he shouted as he splashed around in the salt water and tried to get his arms under her shoulders, the cart shafts were in the way and he found his weight on the shafts was holding her down. She was gasping, the bright red combined bit and ball gag was choking her, he grabbed her bridle and scrabbled at the buckles trying to undo it, finally it came away and he peeled the gag from her mouth and allowed her to sit back in the shafts among the lapping waves to get her breath back.

"Better?" he asked.

"Ughhh, Ugghh," she replied, "I can't," he grabbed at the buckles on the black leather collar that reached from her breast bone to her chin and pulled it off thinking it was restricting her breathing.

"Better?" he asked.

"Uggghh," she replied, "I think so."

Her blonde hair cascaded over her shoulders as her bridle fell away, Andy noted the sides of her head had not been shaved for weeks, months perhaps, "Can you stand?" he asked.

"Yes," she said and she tried to stand, and "No," she exclaimed, as she fell back again.

He reached for her belt, four buckles in a row down the front secured it and he quickly unfastened them and allowed the belt to fall away, leaving her almost naked except for her arm clincher, "You'll have to pull it by hand," he suggested and he slipped the zip down and tried to release the internal straps, everything was corroded and stiff so he struggled but finally the clincher fell away and he undid the two wrist to elbow straps, letting her arms dangle.

She screamed.

"What's wrong?"he asked.

"Cramp," she explained although it sounded more like "Cramb," after spending so long gagged.

"Can you pick up the cart," he asked.

"No, my arms numb." she admitted, "You'll have to help me."

"Oh well, I don't suppose it will make any difference I'm soaked anyway." Andy admitted and he grabbed the cart's shafts with his left hand and her arm with his right and started to guide them back to the waters edge.

"Thanks," she said.

"You got a name?" he asked stupidly, "Like of course you have, what's your name?"

"Sandra, Sandy," she said, "I've been 314 for months."

"You OK?" he asked.

"My arms," she said, "The circulation is coming back and it hurts!"

"It's ok, I did a season as a groom," Andy explained, "lets find somewhere to sit, a sand dune maybe, and I'll give you a massage."

"No, it's ok, really," she apologised, "I ought to get you to where the road is damaged."

"Not if you're in pain," Andy suggested, "Over there," he pointed to a gap in the lines of sand dunes, "OK."

They walked across the sunlit beach, the warmth rapidly dried her sun burned skin leaving strange pale marks where the straps and belts had been, while Andy's soaked and now ruined expensive jacket hung shapelessly and his soaked and ruined trousers flapped wetly around his legs.

They sat together, she sat first and he sat behind her, he noticed her soaking black corset deprived of the support of the wide belt had slipped away from her breasts "Might as well lose this," Andy suggested and he began to unlace the cords, but the knots were soaking wet and very tight and awkward so he took a swiss army knife from his inside pocket and began to cut through the laces one by one.

"Look you're not supposed to do that," she said.

"I'm head of HR," he laughed "I decide, oh I'm Andy Holdford by the way."

"Sandy and Andy, how predictable," she laughed as he threw her ruined corset aside leaving her completely naked but for her butt plug and tail.

"Sounds like some boring suburban couple," he admitted, "Two point four kids and a three year old volvo."

"You forgot the dog and the job in HR," she laughed.

"Can't have a dog, wouldn't be fair with travelling so much," Andy added, "Joking apart,"

as his hands strayed to her breasts.

"You're supposed to be massaging my arms," she reminded him.

"I think I'm supposed to be screwing you actually, to be pedantic," he suggested, "Using the handrail at the point, looking out over the Atlantic ocean."

"Yes," she said quietly.

"You don't sound too keen." he said.

"I'm always looking at the bloody ocean," she said, "Always from behind, half the time I don't know who's meat I have inside me, they always come too soon and then I have to drag them home in that bloody cart when what I really want is a real good old fashioned missionary fuck."

"Jen wants me to terminate your agreement," he said.

"Good!" she replied, "That makes two of us."

"But you'll lose thirty thousand pounds worth of accrued bonus." he explained using a ball park figure.

"I'll get my life back." she explained.

"Why not do South Africa and complete the contract next spring?" he queried.

"I want my life back I'm bored, the whole bloody Island is less than two miles long, I know every inch of track and path and I must know most of the individual blades of grass by name by now," she explained.

"I never even knew grass blades had names," he mused, "But fucks, a bit on the rare side?" he asked, "Is this your problem, frustrated."

"It doesn't help," she said, "It was ok for ages, you know, nothing to worry about at all, compared to Uni where I was flat out 24/7."

"Flat on your back screwing?" he asked.

"No working, and then I only scraped a two two." she complained, "What the hell is the use of that for getting a job."

"What subject?" he asked.

"Law," she admitted, "I know its boring but."

"Necessary," he agreed, "Hows your IT skills and typing?"

"Well they were ok, I haven't exactly had a lot of practice." she agreed.

"How are your arms now," he asked.

"Much better thanks," she agreed.

"Better get on then, will you show me the damaged path?" he asked.

"Look, I know this sounds crazy, but I need something to wear." she said.

"Why, what's different, your tits were hanging out over your corset and your vagina is all pumped up and rouged," he said.

"That's pony girl 314," she said, "Without my costume I'm back to being Sandra Ottershaw."

"No wonder they called you 314," he laughed and he swung his jacket from his shoulders, "Here have my jacket."

She took it gratefully but winced at the pain shooting through her arms as she slipped it on, it hung to half way down her thigh, "So where is this damaged path?"

She glanced at the cart and her discarded costume, the ostrich feathers from her head dress now soaked and covered in sand and completely ruined, "Pick it up on the way back," Andy suggested, "Shall we?"

She led him back to the path, a simple sandy path but defined and contained within concrete edging across the dunes and paved with York stone paving slabs across various small stone or concrete bridges over cracks and chasms in the hard granite rock that made this island.

The damage was serious, a twenty foot span of a concrete beam bridge tilted drunkenly where the foundations had been undermined by the ferocious waves driven by a high tide and a westerly gale, "It seems firm enough," Andy announced, "I think we can jack it back into position and underpin the foundations."

"Ah, what's the we about?" she asked.

"You pull the cart with the bags of cement and tools on?" he suggested, "Or what did you have in mind?"

"Oh," she said, "OK."

"Shall we carry on to the viewpoint?" he asked.

"Do you need to?" she asked.

"No but I want to, unless?" he asked.

"Unless?" she relied.

"Unless you want to fuck here instead?" her smile vanished. "Sorry, did I say the wrong thing?"

"This is Sandra!" she said, "You ask, ok."

"Well no, actually," Andy said, "If this relationship is going to work we fuck when I say so."

"Relationship?" she laughed cruelly, "Punter and prostitute, is that what we are?"

"Sorry, I thought you could transfer to the Penzance office, maybe, if you're bored, my secretary is leaving." he explained.

"And she drops her knickers at a click of the fingers?" she asked.

"He's called Justin and he was a pony boy until we phased them out." Andy explained, "Gay of course, and no, I'm not."

"Sorry," she replied.

"But essentially yes, same deal as here pay per fuck," he explained, "What do you think?"

"It depends," she said, "On how you perform, and over there in the dunes is nice and private."

She led the way to a hollow among the dunes, she had been taken there many weeks previously by a very wealthy client who wanted some privacy as first he whipped her until she sobbed in pain and then he had simply stood in front of her and masturbated as she knelt until his disgusting grey spunk splattered all over her face and in her hair making her feel completely worthless.

"Here?" she suggested and sat on the warm sand.

"Fine," he agreed and he knelt by her, his hands seeking her breasts and then sliding down her taut belly to the stubble where her unevenly shaved pubic hair had begun to grow, "You're not ready?" he asked.

"Sorry," she said, "Oh hell."

"Haven't you got one of those inflatable things?" he asked.

"It leaks," she said, "Sorry,"

"Hells bells," his erection was making a tent pole in his trousers, "OK, don't you dare tell anyone," he said and he bent down and began to lap at her swollen labia with his tongue, "Anything?" he asked, "You sure taste salty."

"I've been in the sea." she pointed out, "But, ah, yes, something."

"What the blazes!" he gasped.

"Its that inflatable bladder thing, it filled me, but it leaks," she said, "It's still in there, sorry."

"It's not your fault, it's your groom's fault." he said angrily.

"No she asked Jen for a new one but Jen said I wasn't worth bothering with," Sandy admitted, "Let me," she said and she gently teased the seven inch long rubber bladder with a bicycle schrader valve fitting on the end from deep inside her, "Horrible thing!"

"Yuck," Andy agreed.

"It's lovely when is hard but," Sandy said.

"I guess," he agreed, "You ready for my big red hot cock." he asked.

"Actually it looks very nice, not too big, I just hate those great big ones," she admitted.

"Thank heavens your gagged most of the time," he laughed, "Because lady that sure is not a good chat up line," but despite the slight it did reassure him as he peeled off his ruined suede shoes socks and trousers, and hitched up his shirt tails.

He got himself into position over her and pushed his cock at her swollen pussy lips, all the pony girls had this done, it somehow made them more equine, vacuum treatment first then collagen injected to keep the lips swollen but firm.

He looked at her face, it un nerved him, she was quite beautiful, and it was such a beautiful spot that it seemed he was with a lover not a paid ponygirl, a costumed prostitute.

He eased gently where he should have rammed his meat in hard, he looked into her eyes where properly he should have looked past her head to the sea views as he rammed her from behind and his mind wandered far away.

"Oh Jesus," Sandy squealed, "You can't be, cumming I mean!"

"Sorry, sorry," he apologised, "Oh god this never happens."

"What was that six thrusts, six thrusts, I haven't had a guy for six weeks and I get six thrusts, I thought you liked me!" she protested, "Jesus!"

"Look, sorry," he said, "Here, suck me, I'll be fine next time."

"Yuck, no way," she protested.

"You'd have to if I had asked for a ring gag," he reminded her.

"I kick, didn't Jen say?" she reminded him.

"Well I'm not going to get hard without am I?" he pointed out.

"Viagra?" she suggested.

"Jesus, I just got carried away ok?" he insisted, "Its beautiful here, you're beautiful,you know."

"Liar," she said then she relented, "OK you win," she said and she took his underpants from the pile of clothing and wiped his cock clean, it responded immediately to her touch, "See," she said and she kissed the top of his helmet where it protruded from his foreskin, "Good as new."

"Not quite," he said,"It's usually."

She opened her mouth wide and took the top two inches of his cock in her mouth and bit down gently, "Agghhh," he squealed.

"Is that better?" she asked, "I bite as well as kick."

"No, but that will have to do," he agreed and he began to undo his shirt, "Lie back, I want to feel your skin against mine."

She lay back and this time he lay down with her naked except for his gold fake Rolex watch, and as she parted her legs once more so he entered her gently yet firmly, "Better?" he asked.

"Nice," she agreed, "Now take your time ok." He began rocking rather than humping, again his mind drifted, "No!" she insisted, "You're not to, it's not fair."

12