Initiation Night at Upper Bournemouth Saddle Club III

INITIATION NIGHT AT THE UPPER BOURNEMOUTH SADDLE CLUB III

Winona was a trifle bit nervous but you wouldn’t be able to discern it by looking at her.

Jasmin was aware she was a bit off but she put it down to the fact that the young girl was reticent to display all of her feminine charms to the general public. At least, to all the members of the Upper Bournemouth Saddle Club. They were passing Candy’s room on their way to the training hall and were joined by the beautiful and delicious Candy wearing only her riding boots and a twist in her hair. The simple elastic twist managed to keep her flowing tresses up in a sensuous “pony” tail.

Candy was attired just like Jasmin and Winona wearing only her boots as they were instructed by the hawk-eyed Mrs. Finch. She walked in front of them with her scrumptious arse cheeks swaying left and right in a carefully choreographed dance of temptation.

Jasmin saw Winona touch her nipple as she looked longingly at Candy’s swinging bottom only inches in front of her. She had a touch of jealousy but smiled instead and slapped Candy’s lovely tush with her impetuous hand just to see Winona’s reaction.

Winona’s frown and protective aura let Jasmin know the young girl was totally infatuated with the naughty Candy Buckmaster, pampered heir of the famed libertine, Sir Jeffrey “Lord” Buckmaster. Sir Jeffrey was reputed to be a major financial supporter of the Upper Bournemouth Saddle Club matched in his generosity by only Jasmin’s own father. Winona was not certain exactly which country Jasmin’s family came from, but she was certain it was nowhere near this quiet corner of the British Isles.

The training hall was more crowded than ever before.

The six novices were all complete with the arrival of Candy, Jasmin and Winona. The six mentor guides of experienced Saddle Club “girl” riders were also present. They were wearing scanty sports bras with holes cut out to expose their various assorted nipples as well as the skimpiest of thongs to cover their feminine parts rubbing on the saddle. A couple of them were joking about the odd spiked ball at the back of #6’s rider mentor’s boots. Winona trembled because she recognized it immediately as a training “spur” used to urge mounts to renewed efforts without the danger of marking them or causing injury. She had never personally used one on any of her mounts because she knew how painful they were to the animals she loved so very much. All of the mentor girls looked at Winona and giggled and laughed because they know she was in store for an interesting “ride”.

Mrs. Finch was there with her ever-present riding whip and she tapped it impatiently against her own leg waiting for the race to begin. She forewarned them that the girl who came in dead last would be treated to a “special session” on the top of her wooden table. Winona was not at all certain if she would win the race, but she vowed she would not be the last to cross the finish line.

The applicant novices lined up facing the gallery.

Winona saw Jasmin’s father peering at her intently. He was a kindly looking older gentleman with a full beard and robes of a flowing nature that hid his bodily shape from public view. She found herself wondering if he wore any type of binding on his man-stick or if it was just bouncing around under there as free as a bird.

She knew her father would not be present because he never stooped to get involved in any of her activities. In a way, she was thankful because she had a sense of innate humiliation in her participation in the ceremonies. Strangely, she felt the familiar trickle between her legs that signaled her arousal at the coming ordeal.

Mrs. Finch told the girls to turn around and bend over.

“Listen carefully, girls, in keeping with the traditions of the club, you will all be wearing Saddle Club “tails” for this race. If you complete the race regardless of in which position, you will keep your tail to signify that you are a lifelong Saddle Club member and entitled to all privileges and benefits thereof.”

The professionally dressed older woman held up 6 long horse tails with a definite thick tapered butt plug to be inserted into each mount’s tiny brown eye. Candy smiled because she was inclined to enjoy any kind of activity “back there”. Winona shuddered a little bit but tried not to let it show. One thing she absolutely could not stand was ridicule of any kind.

Each of the Saddle Club mentors approached the “mounts” with a gob of jellied lubricant to ready the path for Mrs. Finch’s insertions.

Winona looked up at into her mentor’s eyes. She could see the slightly apologetic glance and then felt the delicate fingers probe her virginal rosebud and push the gooey substance right up into her rectal channel. She stifled her gasp of indignation and willed her anus to open up for the protective shield of lubricant.

The progress of Mrs. Finch down the line of girls was sporadically marked by gasps of violated privacy in the most secret of female holes and the laughter and chuckling of the gallery at each individual completed insertion. As she was #6, Winona was the last to receive the flag of perverted submission. She was pleasantly surprised when the thick butt plug found its home inside her quivering brown eye with little difficulty and the weight of the long tail triggered a satisfying sense of orgasmic anticipation inside her female slit.

The saddling was done with efficiency and many “ooows” and “ahhhs” from the gallery. Winona took the padded bit and the reins in her mouth and tossed her head when her mentor pulled her pony tail to show her who was in charge. Her belly was heaving something fierce and her female juices were starting to flow like she was getting ready to spread her legs for a handsome young prince with a long thick cock.

At a signal from Mrs. Finch, the six mentors mounted the new applicants and took up their reins to control their direction.

Winona was very happy that her mentor was actually lighter than Candy and she felt that she could easily handle her weight without any difficulty. The touch of the spiked heels into her lower belly and right on her pubic mound reminded Winona that she would have to be very responsive to the demands of her rider. She wanted to win but uppermost in her mind was her determination to not be last. She was certain the girl who finished last would be treated to a long-lasting correction from Mrs. Finch and she did not want to be that girl.

All the mounts had slide pads on their knees and even mitts that protected their hands from injury on the waxed wooden floors.

The girl in #1 position cried out in distress and the entire gallery laughed to see her steam splash down on the waxed floor. Two female aides ran forward to mop it up and dry the area before they started. A wet floor would be very dangerous for any of the participants. Winona felt sympathetic urges of her own but restrained it and held it in for after the race. She did not want any observer to be laughing at her weaknesses.

Mrs. Finch held the school bell high.

The race was ready to begin.

Winona’s rider pulled her head up high and tapped her hard on her flank with her riding whip the second the bell rang out. She scampered as quickly as she could to the first turn but she was only in third place when they got there. The turn slowed her down a bit and when they came to the straight away at the side of the hall, she had dropped back to fourth place. Her rider was not pleased and slammed her spiked heels hard into her soft belly with a vengeance. Winona looked straight ahead and got into a good rhythm that took her back up to second place before the next turn. Going into the next to last straight section, she had fallen back to third place but there was a long gap between her and the next closest mount. She could feel the sweat and the female juices pouring down the insides of her legs. Her rider leaned forward and Winona felt the touch of her nipples rubbing the skin of her back. Now she knew why the nipples were exposed. The sensitive nipples were aroused and hard.

Going into the last turn, Winona was suddenly in first place. She was more motivated by the touch of her rider’s nipples than the flick of the whip or the digging spur of the spiked heels. The bouncing motion of the girl pushing the saddle down on her back made her want to win the race for the beautiful mentor.

She could feel hot air on her flank.

Winona did not have to turn around to know it was Candy breathing hard on her behind. She was torn between wanting to win the race for her mentor and allowing the beautiful Candy to beat her out at the finish.

They were neck and neck approaching the finish line.

Winona could see Candy out of the corner of her eye. She could see her mentor whipping her hard and driving her heels into her soft and delicate tummy. The sweat was flying off her racing body.

Winona’s mentor leaned low and rubbed her nipples on her rippling shoulder muscles. That was all the urging she needed. She flew across the finish line in first place with a record time that beat the old record from some thirty years ago.

She remembered her mentor rubbing her down to cool her off. The sight of poor Jasmin being led off to Mrs. Finch’s office for her last place finish correction lesson was disconcerting but her room-mate was so bloody exhausted that she put up no resistance at all.

Candy was pleased with second place. Her father was not.

Lord Jeffrey came down and instead of congratulating his daughter on her second place finish; he moved behind Winona and allowed his fingers to explore her still trembling flanks. She was so tired; she could not even muster an objection to his inquisitive expedition. She gasped when he yanked out the well seated butt plug tail. Winona was certain her brown eye was wide open and gaped after the long ride with the inserted plug but was unable to hide her shame from the older man’s eyes.

“You will dine with my daughter and I tonight, young Miss Winona, I want to find out what drove you to win that race. She should have won. I trained her for this and she is above all, a winner.”

Winona found that the thought of many rumors of Sir Jeffrey’s sexual prowess made her pussy juice squirt at the touch of his fingers on her sweating rump. She just nodded her head in submission to his statement and reached out to comfort her friend Candy. Candy was fully aware of her father’s displeasure and she felt sad that she was unable to feed his desire for her to excel at any cost.

When Jasmin finally made it back to the room, Winona saw she was mortified at coming in last. The visible results of Mrs. Finch’s ministrations made her run to the bathroom to get a soothing salve for her bottom and legs.

“Push your bottom up, honey, mama is going to take care of you real nice!”

Jasmin was purring with emotion and opened her legs for Winona’s fingers.

“That’s nice, mommy, right there. Put some right there, please!”

After she tended to Jasmin’s tattered bottom, Winona spooned her and rocked her into a restful sleep. She looked down at the sleeping girl and closed the bedroom door.