Strider Gets Her TailbyBoxlicker101©
Her tail! Of course! All the other ponygirls parading outside had tails so, of course, she had to have one too. Tara had seen those appendages waving and bobbing, and had assumed they were somehow attached to the harnesses, and she hadn't thought about the absence of hers until that moment. Strider wanted to get her tail, so she could go out and be chosen by a master and join the other ponygirls in the field, but Tara was very reluctant. It was quite obvious to her that what the outfitter wanted to do was to shove that carrot-shaped thing into her ass, and she balked at that, and held her cheeks tightly clamped together.
The outfitter could feel her reluctance, and it was not something he was unused to. "C'mon, Girl," he cajoled her. "It won't hurt, and once you have your beautiful tail, you can join the other ponygirls in the field and prance and strut and have fun. You can't go out without it, though."
The bad memories involved a former boyfriend. Tara surrendered her cherry to him while still in high school, and they went steady for two years. The previous May, shortly after her eighteenth birthday, he persuaded her to have anal intercourse with him, telling her it would be fun, and not hurt at all. That was a lie. It had been painful from the first penetration and, when she pleaded with him to stop and take his cock out, he ignored her, and continued fucking her ass until he ejaculated into her. She was sore for a week, hardly able to walk or sit, and had to miss a parade and leading cheers at an important track meet. That was the last time she had anything to do with that no-good bastard, and Tara vowed to never again let a man use her like that.
Strider really wanted to go out and do the prancing and having fun that the outfitter had talked about and, if it meant having a tail shoved into her ass, then that was what would happen. She could hear the audience, which must have gotten bigger since she left, and they were applauding and loudly cheering. They weren't cheering for her, although they should have been. Strider was deprived of that, because she was still inside, struggling with wanting to be a ponygirl, but not wanting to wear a tail, even though all the others were wearing them with no problems.
The outfitter seemed to be close to giving up on completing the conversion of the young woman to a ponygirl. "Well, Girl, if you don't want to, you don't have to. We won't force anybody to do anything. I'll have to take all the gear off you though." His hand went to one of the buckles as if to start the divesting.
Abruptly, Strider realized her very strong desire to be a ponygirl that afternoon, and how she wanted the tail to be inserted. In fact, she would invite it. With the bit in her mouth, Strider couldn't speak to the man, and badly needed to find another way to tell him to go ahead with it. She needed to tell him before he started taking away her shiny red leather harness and bridle and even the bit that she was growing quite fond of. There was a way to do that without speaking, but she would have to move quickly. Strider twisted her wrists and pulled them loose from the elastic bindings of the belt around her waist. When they were free, she reached back and spread her cheeks wide apart, mutely telling the man to insert the tail in her ass.
He understood her silent plea. "Good girl," he crooned. "Good ponygirl."
The outfitter added more of the lubricant to the middle finger of his right hand and poked it into the ponygirl's ass to spread it. There was really no need to do that. The tip of the butt plug that was fastened to the tail was narrow enough to easily fit into her without lubrication but, like most men, he enjoyed playing with the pretty pink booty of a sexy young woman. He inserted the tip into the small hole that Strider was holding open and began carefully imbedding the tail, twisting it back and forth while he pushed. His eyes carefully watched for any problem, such as loose skin, because he knew that such an insertion could be quite painful if anything went wrong, especially with an inexperienced ponygirl.
While his right hand was busy working the tail into Strider's ass, his left hand reached around and, as if needed for leverage, lightly squeezed one of her breasts. It felt wonderful, firm and supple and vibrant and covered with exquisitely soft, smooth skin. When he lightly tweaked her nipple between his fingers, he was happy to feel it was erect, as was the other one when he moved his hand to fondle the second of the twin treasures. The man really loved his job.
Strider didn't mind having her breasts fondled. After all, ponygirls didn't object to being touched by their masters and, for the time being at least, her master was the man who had dressed her in her beautiful tack and was inserting her beautiful tail for her. Tara was apprehensive about the pain she was still expecting to feel at any second, and was wondering why it hadn't started yet. Shortly after the penetration began, there had been a very slight amount of pain, but that had only lasted a few seconds. Tara even had to admit to herself that the trivial discomfort had quickly evolved into pleasure. Strider was actually enjoying having her ass filled, and not just because the tail would complete the transformation of her into a ponygirl. That was the main reason, but she was actually deriving a lot of pleasure from being crammed by the carrot-shaped object, and it felt even better as it went in deeper and her ass was spread wider.
Finally, the entire tapered part of the butt plug was in place, and Strider's anal sphincter closed around its base. It would stay there until the event ended, and would have to be removed by the same outfitter or someone else, who would have to work her sphincter around it with his fingers and pull it free. With Strider completely a ponygirl, he let go of her breasts and stroked all around her ass for a final time, even letting his fingers curl under her crotch to touch her pussy. It was dripping wet, which was the usual condition of a ponygirl after her tail was inserted.
He scooped up as much of the fluid as he could with his fingers and licked them off. It was delicious, as he had expected. That was what he loved the most about his job. Although having the sexy young ponygirl across his lap, where he could fondle her freely was delightful, he was anxious for her to get up and leave so he could go and masturbate. Outfitting desirable young women as pony girls was an extremely arousing job, and the last one had been the hottest of all.
"Okay, Strider Girl, you're all set. Go out and wow them, Ponygirl. Put your wrists back in the restraints first, though."
Even before climbing off the man's lap, she whinnied her appreciation as best she could with the bit in her mouth. Once on her feet, Strider turned toward the exit and, after securing her wrists again, started toward it. She whinnied again, and tossed her head, feeling her dark brown mane flowing around her face, but not blocking her sight. Raising her legs even higher than Strutter had been doing, and thumping her bare feet onto the cement floor, Strider started toward the exit, with her head high and her breasts thrust out.
She felt good about herself. She felt good about everything, even the tail that was swinging from side to side and sending more pleasure swirling through her body, and juices trickling from her pussy down her legs. She felt good about her beautiful and shiny red leather tack that looked so good against her skin and mane. Strider was eager to be selected by some lucky master who would put her through her paces to repeated standing ovations, and help her outshine all the other ponygirls in the field. That day was going to be one of the best of her life.
Thank you for reading this story. I hope you had as much fun as Strider and the other ponygirls will be having. I like writing stories on Literotica, but I like it a lot more when I know that people are reading and enjoying them, and I appreciate it when readers take the time to express their opinions by voting. Like most authors on Literotica, I practically live for feedback from readers, either public comments or email to me. Such feedback, whether praise or criticism, helps me to write more and better stories, and I respond to it whenever I can.