Ch, Ch, Ch, Cherry!

Leaning slightly back Amanda pressed her back into Derrick, feeling his own chest rise and fall as he breathed. She felt at ease as he had both hands wrapped around her waist from behind and clasping over her stomach as he leaned against the stable’s wooden red painted wall. She only half listened as Carl went on at length about how his son only knew what he taught him and how he brought him into this world and if he kept giving him lip he would send him out of it. The old man didn’t have any malice in his voice and it wasn’t something she ever would joke about, but his son, a full grown man in his mid thirties, didn't seem much bothered by it all as he finished buckling the saddle on the horse that Candi was to be riding.

Most of Amanda’s attention was on Bailey, who was just outside the stables with her green wide eyes full of tears as they watched one of the ranch hands bring over a brownish red horse. Without looking away from the platinum blonde girl, Amanda reached up with her hand to place her palm on her boyfriend's cheek. “Thank you for doing this.” She said, pressing her lips into a line as she held back her own emotions. Bailey had never been incredibly open about himself, but she knew that he had fancied himself a little bit of a cowboy. He wasn’t one, but she never spoiled the illusions he had when he talked about helping breaking in a fillie, a young female horse that he got to name Cherry after their coloring. She imagined it was Bailey’s father that did the breaking in, but just had Bailey help. The more she did learn about his past, made her wonder though, his parents put a lot on his shoulders and made Bailey grow up faster than any child should. The loss of his parents, one after the other had devastated him, he almost completely shut down and even offers of sex, something she knew he was always up for hadn’t had the impact she thought.

Here now, she saw Bailey getting a piece of that childhood back that he… she wanted and needed. Closure that was unfulfilled has come all thanks to the Connors. Bailey had actually opened up to Candi, a friendship that had started as Bailey just needing to keep her company had turned into something she was sure was deeper than their own in some ways. The family from California had not just listened to Bailey talk about what they had and lost, but put in no small effort to reunite Bailey with what was lost, even if it was just for an afternoon. Cherry was a bridge between Bailey Andrew Smith and Bailey Ann Best and she felt blessed to see someone she loved look so content.

Pressing his hands together in a praying motion and holding his touching index fingers to his lips Bailey watched his pony, who was not so small now, a full grown mare, be walked closer to him. Bailey had to hold in the desire to run to his old horse, wanting to hug it and terrified she wouldn’t recognize him. It had been years and he looked so much different, now, even smelled different. There was no chance of Cherry recognizing him by scent, the last time she had seen him, he had been covered in sweat from a day out in the sun making sure all the horses got fed and now… now he smelled like strawberries and cream.

“Here you go miss.” Hector the hispanic ranch hand said as he approached the girl who looked to be dressed the part of how she thought a cowgirl should dress. “I understand Cherry here used to belong to you?”

Without taking his eyes off the horse Bailey nodded to his question, reaching into his pocket to grab one of the marble sized chalky mints he had ready. Holding his hand out with the mint at the center of his palm Bailey had an eager smile on his face. “Do you remember me girl? It's me Bailey… I look like, a little different, but it's meee.”

Hector eyed the girl up once more in her tight jeans that were doing great things for her rear end and her perfectly made up face that she did just to go riding and imagined she meant she had gone from some ugly duckling to someone that wouldn’t be safe walking alone into a bunk house at night. “You look fine to me.” He said with what he hoped was a charming smile.

The smile on Bailey’s face grew in volume, the joy present easily touching his eyes as they filled with tears yet again. ‘OMG I just redid my eyes… like, come on I don’t want Cherry seeing my cry!’ Bailey thought as his heart felt light enough to fly, when his old horse moved another step forward to nuzzle her head into him. Giving the worker only a small piece of his attention Bailey glanced over to him and then back to who was important. It wasn’t that he didn’t think the guy wasn’t important, he just wasn’t Cherry. With how big Bailey’s smile was, when he turned it on Hector, even for a second to him at least it felt like a connection as the girl smiled back at him for his compliment.

With his old horse so close, Bailey took both sides of Cherry’s head, gently hugging her and closing his eyes as he rested his own hair against hers. Bailey could feel the warmth of the horse's breath as it breathed in and out, its muzzle rested against his breasts. “I love you Cherry, I miss you so much!” He freely admitted.

Feeling exhilarated, Bailey walked over to the open side of the stables, its doors wide open, Bailey still had the type of smile on his face that would cause muscle fatigue to someone not so practiced at the activity. “This is her! This is Cherry!” Bailey declared to the others.

Candi had just been about to give the man saddling the horse she was to ride a lecture about being cruel to animals with how he pressed his knee into its side as it tightened the saddle when she turned to see her friend the happiest she had ever seen her. “Awww, love it, love it, love it!” She said, taking a breath. “I’m suuuper glad you got to see Cherry again, buuuuuut don’t like let this guy put the saddle on her or he will kick her in the side.” The smile on her face sliding away for just a heartbeat as she shook her head slightly and glared at the over tall and broad shoulders man that had been prepping the horse for her.

“Miss, I’m tellin ya, I didn’t kick or hurt him one bit. Scout here is a good riding horse, but he aint no fond of being saddled.”

“So you hit him?” She glared at the man once more before rubbing the her hand on the neck of the horse. “Poor Scout, I’m sorry he is so mean.”

With a giggle Bailey shook his head enough to cause the single brain to dance about. “No, like Candi sometimes horses take in a deep breath.” Bailey said before doing just that and puffing his chest out and holding his hands to the side, while standing on the balls of his feet to give the impression of being bigger. Bailey only held it for a second before deflating and tilting his head slightly to the side as he looked at Candi. “So you have to like push on them a bit otherwise the saddle will be loose.”

Carl, who had taken a break from giving his eldest son grief when the young short haired platinum blonde girl seemed happy to harass him, slapping a hand across his thigh. “That, that right there is right. Ed, take a lesson from gal right there. You don’t tell paying customers they are wrong and argue, take the time and explain. I know I didn’t teach you one bit of manners, but I figured you might have picked up a thing or two from your Ma.”

His patience starting to slip Edward gave his father a flat look. “You want me to finish up here or do you think you could do a bit of work.”

“Boy, I have done plenty.” Carl started to say before he heard the girl who had been giving his son grief speak up again.

Narrowing her eyes, the upset expression on Candi’s face faded to a look of curiosity. “Ed, you like work at a stables and your name is Mr. Ed?”

With a look of mischief the elderly man gave the girl a smile and a wink. “Named him after a horse I did.”

“You did not! Edward is your middle name, I was named after you, don’t be fillin their heads with your nonsense.”

The exchange had been enough Bailey found himself giggling as he stood next to Candi who had started the laughing fit.

“Now, now, come on girls. Be nice and tell Ed here that you are sorry and appreciate what he is doing.” Derrick walked away from the comfort of leaning on a wall on a wonderful, holding an even more wonderful woman.

The owner's son waved his hand in the air. “It aint no bother, your daughter here can stand near Scout and I will get the rest of our gang together for ya.” He then turned his head to his father. “Unless you wanna help?”

“I am helpin! Without me you wouldn’t be here to do it.”

Soon enough everyone was outside the barn, sitting in their saddles atop their assigned horses. Bailey reached down and patted the side of Cherry’s neck, while Candi looked incredibly unsure of herself. She held onto the reins in one hand like she had been told, the other gripping the horn on the saddle with a white knuckle grip and pressing her legs into the sides of her house Scout. Her actions causing the horse to move about, shake their head making Candi sway even more.

Fear gripping her Candi closed her eyes tight, both hands moving to the horn on the saddle positive she was about to fall to the ground. She could stand a ladder. It wasn't like her fear of heights was crazy, but she had no idea how Bailey or even her daddy was sitting still. Her horse, Scout, seemed to hate her and wanted her off. ‘Don’t fall, don’t fall, don’t fall!’ She told herself over and over again.

“Candi, Candi, HEY!” Bailey said, trying to get his friends’ attention. When he saw her open just one eye and even then only partially he continued. “It’s like fine, I promise.”

“He like, wants me off! I shouldn’t be riding, I can totally wait in the car!” Candi said as Ed moved over next to her to take Scount’s reins into his own hands and try to calm the horse down.

“Miss, Candi was it? Just need to calm down, you be calm and so will Scout. Calm, calm… Shhhhh.”

Snapping open both eyes Candi pinched her lips together as she looked at the cowboy hat wearing man. “I’m not an animal and I can’t help it if the horse wants to throw me off!”

Trying to make up for the tactless Candi’s father spoke up. “Candace, he didn’t mean it like that princess, he is just trying to help. Look at me honey, this is maybe my third time riding and Jasper here is calm.” When talking to the owner, Carl, Derrick had told them Bailey had at least a little riding experience and the rest of them were novices. He had rode once or twice back in his youth at a summer camp, but how long ago he didn’t think it was much worth mentioning then, but seeing is daughter struggle he wanted to help the best he could.

Moving his horse Bailey made it so he was parallel and facing his scared friend. “Are you squeezing your legs?” He asked gently.

“Yes! I don’t like want to fall off!” The teen girl said not willing to give up her grip on the horse.

“Alright like umm…” Bailey thought for a second. “Remember the float that gil had at the water park the one that looked like a pink donkey?” He asked, nodding his head. “Like, what would happen if they squeezed their legs together when they were in the water? They would like sink or totally get a wedgie. You are making your horse nervous because you are doing that to him, well like kinda.”

With more than a little hesitation Candi tried to relax her body, positive the second she did the horse was going to throw her off its back, but as she did nothing happened. “Am… am I like doing it?” She asked through clenched teeth.

“You are doing great sweetheart, Amanda said cheerfully, wanting to encourage the girl, while the employee helping had a not so helpful reply.

“Doing it alright, now you are sitting fine. Think you can keep that up when we move?”

With Candi mastering the ability to sit on a saddled horse when it wasn’t moving the group pressed on, starting to move deeper into the property and heading in the direction of a riding trail. It was here that Ed ran into a different problem, he was paying extra attention to the pretty young thing that had obviously never sat a horse before when the other teen took off. He had them all at a steady walk and she had done past a trot and went to a canter. “Hey now! No riding ahead, you gotta stay with the group!” he said before swearing under his breath, hoping the girl didn’t pick up more speed and fall off and hurt herself. The last thing his family needed was some people coming here and getting hurt and suing them. The paperwork said they weren’t liable, but his father hadn’t had no lawyer look at it.

Wanting to feel the wind blow past him Bailey urged Cherry to pick up the pace, so he could feel alive. Feel alive like he had galloping about on Cherry many years ago or even riding his motorcycle. Things now were different and as he picked up his pace he felt the horse moving under him like he remembered but this time he was wearing a prosthetic that had been build to respond to physical stimulus and has his crotch pressed into the moving saddle he felt the vibrator wrapped around his imprisoned penis come to love. “Ah, oh… oh, OH!” With each series of buzzes the breath in Bailey’s lungs came more ragged as his eyes grew wider. “Oh my god, like need to stop.” Bailey said, making no move to slow his pace.

Feeling his body shake in delight, Bailey did what he told Candi not to do and pressed his legs more into his horse, causing Cherry to break into a gallop as it thought its rider wanted to run. Bailey had no problem staying in the saddle, but as the pace increased so did the stimulation as his body rocked back and forth and up and down on the saddle. Focus on where he was going fell to the wayside as did thoughts of slowly down, let alone stopping. The wind was whipping by him, his braided hair danced in the wind as his hidden male member started to leak as quickly the precum turned into an eruption and his body felt wracked with pleasure.

With being so focused on himself internally Bailey hadn’t noticed Ed catching up to him and taking the reins to slow them more and more down. With a small but continent smile Bailey looked at the Ed, taking him in for the first time. Tall, broad shoulders with a squared jaw and piercing blue eyes. Bailey thought he looked every inch the cowboy his father was… probably more so. Looking at him and feeling the way he was, Bailey thought of the experience with riding on the back of his old bike and how much stronger Ed looked than Liam… Liam who at this second probably was getting some of his first lessons on how to walk in heels.

“You can’t be doing that now, you do that again and we are done. You hear me?”

His panties wet from his own cum Bailey felt like he was slowly floating down from cloud nine and could use a nap. “You… you like look strong.” The feminized man said absentmindedly, giving voice to his thoughts and thinking how unfair it was.

“Ahhh, What?” The confused rancher said as the green eyed girl looked at him dreamily.

“Hmm?” Bailey asked before blinking a few times, giving the man he was looking at the impression he was batting his eyes at him. “Oh umm, I didn’t mean to say that out loud.”

“Okay.” He said with only a slight accent. “How bout we walk, and I do mean walk back to the group. Later… if your good the two of us can pick up the pace.”

Remembering the feeling he just had, Bailey rocked his hips, he knew it couldn’t have been that long since he got off… not since… his thoughts went to August’s lips around one of his nipples and despite just getting off noticed how stiff his nipple felt. The ride had been exhilarating, but the feminine aspects on his chest had bounced around the bra he had chosen to wear doing little to hold them in place and one had slipped free from the bra. It wasn’t like he was exposed, but with a light blush to his cheeks he still had to adjust himself and without his mouth checking in with his brain he responded to the statement about being good. “I’m a good girl and proud.”

Raising an eyebrow he looked at the girl questioningly, thinking how she was probably around half his age and probably five pounds of trouble in a one pound sack. “Good… good to hear it miss, lets just get back to the group.”

“Okay… but like can you not call me miss?” Bailey asked, the man using it was a constant reminder of how he looked. “Just like call me Bailey.”

Diverting his full attention away from the flirting girl he gave a nod. “Yep, can do.” Ed said wanting to pick up the pace so he wasn’t left alone with the pretty young thing who he was now convinced had run off just to get them alone.