Tally-ho! - 1. Chapter 1

Casey Winthrop wasn’t gay.

The other exercises riders, all male, would argue against that statement but Tia knew otherwise. Gay guys don’t look at women the way Casey Winthrop looked at her. No, Casey may not be gay but he was hiding a secret. Tia was pretty sure she’d discovered that secret in the old tack room of the barn.

She’d thought long and hard over those looks Casey gave her. They’d sparked an answering heat in her only Casey never saw this. As soon as she caught him watching her with that peculiar combination of curiosity and admiration and longing, he’d glance away. She’d thought long and hard about her discovery in that tack room too, that graveyard for bridles, harnesses and saddles. She suspected the secret he kept also prevented him from acting on whatever curiosity she held for him.

It was this suspicion that had her crossing the wide lawn that separated the horse training facility at Winthrop Stables from the family house. Nothing wrong with a few secrets. Everyone had them. But secrets shouldn’t hold a person back from the things they really want. Things they need.

Her riding boots sounded heavily on the porch steps. A moment later, she delivered four sharp raps on the wood frame of the screen door. Bea Hatchett, the housekeeper, answered. The woman looked much like her name with a long face and narrow, protruding nose.

“Good morning, Bea. I’m here to see Casey.“ Tia always used her best manners with the woman. She could be cantankerously protective of the Winthrop children, which even at the age of 22 she still considered Casey to be.

“Well, maybe he’s not here. Maybe he’s gone down to Elmwood Stakes with everyone else. Come to think of it, what are you doing here, girl? They didn’t all leave you behind now, did they?”

“Yes ma’am. Mr. Winthrop wanted someone here since not all the horses traveled. Worked out best for me to stay since I live on the property anyway. Casey didn’t join them. He said he needed to study this week and there’d be too many distractions at Elmwood. Could you check on him, please?”

“Seems he might not welcome you as a distraction either,” The housekeeper sniffed but she retreated into the house to look for Casey. Tia was not invited inside.

She didn’t mind. While she waited on the home’s gracious wrap around porch, she looked over the Pennsylvania countryside. The Winthrop family owned a judicious amount of the land she surveyed. Somewhere beyond the two rolling hills on the far side of the barn was a shallow stream and beyond that was a fence marking the property line with the Chandler property. Once the Chandler lands were traversed a similar fence would mark the boundary of the next tidy estate and the one beyond that.

Low fences. All of them. This was fox hunting country and by agreement and tradition the owners of these estates granted trespass rights in support of the local obsession. Eight months out of the year, on Wednesdays and Saturdays, these hills and forests and streams hosted the mad dash of hounds and hunters and the spectators who gathered on the hillsides to watch them. There was a fox too, Tia knew, though participants seemed more concerned with the chase than the kill.

Casey’s father, Charles Winthrop, trained steeplechasers. The barn and adjoining facilities were state-of-the-art. Tia counted herself lucky to have been hired as an exercise rider here, particularly since the position included small living quarters above the barn and boarding for her horse, Blue.

“Tia? Bea said I’d find you here.”

Tia watched Casey walk across the porch to join her at the railing, looking more comfortable than a lazy Sunday morning. Slender, with pale skin and dark hair that he kept trimmed close, he moved with an unconscious efficiency. Dust, dirt, wrinkles never seemed to attach themselves to him, not even when he mucked out a stall. He was always precise, fine, measured. He was that way now, wearing a pressed, yellow button down shirt and jeans. He was about her height, but she was tall so that didn’t necessarily make him a small man. His feet were bare and as he leaned against the railing next to her, she noticed he held a book and was marking his place with a finger.

“Hey Casey. I thought, if you have a couple hours, I’d see if you wanted to go for a ride. Everyone’s gone down to Elmwood Stakes. Chores are done so I have the rest of the day free and seeing as how we are the only two left – except for Bea - I thought we could go for a pleasure ride, eat lunch on the trail.”

She’d rambled on with the invitation, she realized. She hadn’t felt nervous, though she’d never approached Casey this way before, hadn’t at all doubted her plan for the day until he was standing in front of her, looking so cool, so undisturbed, so collected. So untroubled by his secret. A flicker of doubt crossed her mind. She forced herself to stand still as she awaited his response, to not shift her weight from foot to foot.

He took his time answering, thinking things through in that determined way of his. He looked at her, eyes inscrutable, and for the first time, she asked herself what he might see in her. Like him, she was slender but the work with the horses and the barnyard labor had given her arms and shoulders a breadth and definition she didn’t normally carry. She was pleased with the effect; it redefined her body, gave her an extra swagger when she walked. Last week in town, she’d twice been addressed as “Young Man” by shopkeepers viewing her in profile.

They had stuttered and blushed their “oh, pardon me...” and “ I meant to say…” and “I didn’t see you have…”

“…breasts.” Tia would think, mentally finishing the sentence for them when their words trailed off. No mistaking she was a girl when faced full on, but with her boyish haircut and new musculature and neutral attire, she was often mistaken for male. She enjoyed the charade. Enjoyed their discomfiture.

But Casey Winthrop knew she was a girl and he still looked at her, well, like he did. Like he was curious about her, as if he wanted her to notice him. She was curious about him too.

“Sounds fun, Tia.” Casey smiled his acceptance. “I figured you’d be looking for a day off, that is, a day to enjoy on your own. You sure you want company?”

“Yes, I’ve been looking forward to riding with no particular plan, no exercise routine, just for pleasure.” Tia thought about the other types of riding that could be for pleasure. If she was right about Casey and could get him to trust her, they would get to that too.

“I’ll have Bea pack a lunch while I change into riding gear.”

“No need.” Tia detained him when he moved towards the door. “Just pull on some boots. I’ll bring the horses around. I’ve already taken care of everything.”

“You have?”

“Yes, I’ve planned everything for you.” She thought he may have swayed a bit at this statement, felt the movement beneath her hand where it lay on his arm. His eyes deepened and for the first time that day she caught the longing she sometimes saw hidden there. “Meet me out front here when you’re ready.”

They rode silently at first, walking their horses along a well-worn bridle path through the woods. Casey was on Lunar Eclipse, a beautiful thoroughbred who stood over 16 hands. Eclipse was a former flat track horse who’d never won. Casey had rescued him from auction as a three year old and with some patient re-training, the two of them had racked up a modest string of victories on the steeplechase circuit.

Tia was on Blue, a Morgan Welsh cross she’d acquired while taking her training as an exercise rider in Kentucky. The silence and the walking were welcome on her part. It had been years since she’d ridden side saddle and the change in center of gravity was taking more adjustment than she remembered. Casey and Eclipse were behind them on the single track. She wished she could see him, better gauge his reaction to the saddle. It certainly had taken him aback when he first saw it, as she knew it would.

She’d been holding the reins of both horses when he’d come out of the house. He’d been blushingly pleased when she’d offered him a leg up onto Eclipse. She’d made a show of walking around the horse, double checking the cinch and the length of the stirrups.

“You good?” She’d rested a hand on his leg, felt the muscles flexing beneath it.

“Yes, perfect.”

It wasn’t until she’d walked Blue over to the steps so that she could more easily mount that he’d noticed the side saddle. His eyes had slid away from it, away from her. He’d made no comment on the unusual choice as they commenced their ride. She knew, then, that she’d guessed right. He’d recognized the saddle.

She straightened her back and squared herself, searching for that connection with Blue, wanting to match Casey’s easy equitation. She was conscious of him behind her, watching as she led the way beneath the canopy of trees.

“You’re a California girl, aren’t you?” Casey called up to her. “What did you think of your first Pennsylvania winter?”

“I loved it, actually. At least I started loving it after I got some thermal breeches.”

“Do you miss it?”

“California? No. I was ready to move. What about you?”

Tia knew he’d been a student at Cal Poly, that he had abruptly announced last December that he was leaving the campus and planned to finish up the last semester of his degree from home.

“I don’t have any reason to miss California. You must have experienced some homesickness though. You didn’t leave anyone behind? Someone special that you miss?” The path through the woods widened enough that Casey was able to pull his horse alongside her.

“I have a friend at Oberlin. We were close in high school but we both knew it wouldn’t last.”

“Boyfriend? Girlfriend?”

“Interesting question.“ Tia did her best to deadpan the response. “Our junior year of high school Alix self-described as a cisgendered, asexual panromantic. By the time we graduated, he’d settled on tentatively trans two-spirit, pansexual, fancy queer. Personally, I think he’ll ultimately decide to simply be bisexual, but it was fun hanging with him while he figured it out.”

The path opened into one of the rolling green fields as she finished speaking. She snuck a look at Casey and was gratified to see the surprise on his face. “Should we breeze them out?”

Without waiting for an answer, she press Blue into a canter. Moments later she heard Eclipse thundering behind. She expected Casey to take off on the more powerful horse, but he rode just behind them, a bit off to the side.

“You’re doing great!” he yelled. She knew he’d noticed her skill on the side saddle and took a ridiculous amount of pleasure from his compliment. It was different, more dangerous, than riding astride. The thrill was enlivening.

When they reached the next stand of trees, they again found themselves riding abreast.

“That was beautiful. Unusual to see a side saddle in use these days.”

“One of the rainy day tasks in my job description is to go through all the gear in the old tack room, inventory it, fix it up best I can.”

“I hadn’t realized.”

“Funny thing is, when I found this saddle, it had already been fixed up.”

“You don’t say.”

“Yep, it’s been well cared for just sitting in that back room under a thin saddle blanket. Can’t help wondering how it got that way.”

“Just where are we heading, anyway?” Casey’s change of topic was abrupt, and Tia let the subject of the saddle slide for now.

“Out to the old playhouse. Our lunch is waiting for us.”

“Home away from home for my sisters. They spent hours there playing dress-up, make believe.”

The playhouse was a miniature castle, a life size dollhouse built for children who enjoy a privileged upbringing.

“What about you? Didn’t you join them?” Tia was curious about the family dynamics which she’d observed mostly between father and son. The mother had died some years ago and both sisters were married and raising families in Connecticut. While there was no outright conflict between Casey and the senior Winthrop, their relationship was far from close. They interacted with one another with business-like curtness. Charles Winthrop was warm and gregarious with his employees; the chilled relationship with Casey had fed the rumors of Casey being gay. Why else would the man be so distant with his own son?

“They were much older than me. I’d ride out here on my own when I got old enough, but mostly it was a place for me to read.”

“Well, now your father has turned it into a year round storehouse and a warming hut in the winter. It’s a relief to break here in the middle of the morning workout in January.”

They pulled up at the small structure which had been outfitted with plumbing as well as heating and cooling. “I’ll get our picnic set up. You see to the horses.”

When he returned from watering the horses, Casey took in the extravagant picnic she’d laid out in the shade of a tree but said nothing, seating himself cross legged on the blanket. She’d stocked their provisions the previous day, having spent a sizeable chunk of her grocery budget on ordering the local market to pack up sandwiches, fruit, cheese, beverages and sweets. Not sure what Casey would like, she’d requested a variety. There was much more than two people could eat in one meal.

“Go ahead,” she gestured to the food next to them. “Eat up.”

Long fingers selected a wrapped half sandwich and peeled back the paper. Tia watched the careful, precise movements.

“Mind if I ask you a couple questions?” Casey bit into the sandwich.

Tia shook her head, busily loading up a plate with fruit salad and chips.

“How old are you?”

That wasn’t what she’d expected. How old do you think I am? She wanted to ask. Instead she answered directly. “Nineteen.”

He nodded, as if that confirmed something, then, “Are we on a date?”

He chewed slowly, awaiting her answer, not giving anything away.

Did he want this to be a date? She waited for him to swallow, reached an arm out to stop him as he lifted the sandwich for another bite. Silently Tia removed it from his hands, set it aside. Tia loved this about him, the way her watched her, let her take the lead, let her direct his actions. His compliance thrilled her. Kneeling beside him, she grasped his chin and tilted his head brushing his lips with hers. “Yes, I would like to think we’re on a date.”

His tongue darted out to lick his lips, capturing the lingering taste of her as she pulled away. It was the most erotic thing she’d ever seen. He let out a little laugh. “I wasn’t sure you’d noticed me. At least, not as anything more than the owner’s son. A fag son at that. That’s what they all say, isn’t it?”

“Most of them wouldn’t use the pejorative so flagrantly, but yes, consensus is that you’re gay.”

“Guess we’re perfect for one another since they all think you’re a lesbian.” Then, as if suddenly worried she’d take offense, “It’s probably your hair. It’s so short. And you’re tall. You don’t wear make-up, but why would you around the barn? So don’t think…”

But Tia was openly laughing now. “Frankly Casey, the people who call me a dyke aren’t that far from the truth. I mean, it’s not like regular guys go for me. They don’t interest me either. Remember I told you about Alix? Guys like that are more my type.”

She almost dove back in for a deeper kiss but forced herself to sit back and pick up her plate of food. Casey looked confused, as if he was now trying to figure out where he fit into this scenario. She waited to see if he would say something. Reveal something more about himself. But he remained silent until she started a neutral line of conversation.

“Tell me what it was like growing up here on the Winthrop farm.”

So, he described his life as the late child to older parents. The family business and recreation both focused on horses. His father hoped to pass on operations of the business to one of his children. She reciprocated with stories of growing up in a family of tenant farmers on a dairy farm in northern California. The position as an exercise rider for his father was a stepping stone to her ultimate dream of becoming a professional jockey.

“Where did you learn to ride aside? Not a skill I expected to see in a tomboy such as yourself.”

Casey was reclined on the blanket, resting on one elbow as he questioned her.

“The woman next to the dairy had a hobby farm with a couple horses. I use to stand at the fence line and watch her working them. One day she invited me in. That’s where I first learned to ride. She taught me loads, including how to sit aside.

One thing that tomboys figure out early on is that people who designate activities as “girls only” or “boys only” are often wrong. I loved horses, wanted to learn everything about them. Still do.”

“A wise philosophy, the girl-boy thing. I guess I can see why that fellow you mentioned, Alix, was a friend of yours.”

Tia smiled to herself. Strange to hear Alix described simply as a “fellow.”

“I’m just myself. I think everyone should just be themselves. Should be allowed that.” She stretched alongside Casey, the tree providing shade from the rising warmth of the spring day. He still seemed unsure around her. More comfortable, certainly. He didn’t avoid her eyes anymore and their conversation was coming more easily.

But, he was still holding back, not fully engaged. She had the sense that Casey was thinking furiously about something even as they talked. Like he was trying to work out a difficult math problem and discuss riding technique at the same time. She traced fingers up his leg, stopped at the hipbone.

This time when she leaned forward for a kiss, he caught her and rolled backward. She ended up sprawled across him. He let her control the kiss, its depth, its length. When she raised her head, he was heavy lidded. She could feel him thickly against her hip, but even now there was a reserve about him. A waiting cautiousness. What did she need to do to earn his trust, to prove his secrets were safe with her?

She pushed herself to her feet and extended a hand to lever him upwards. “C’mon. I have a surprise for you. Back in the playhouse. I think you’ll like it.”

“This whole day has been a surprise. “ He went along with her willingly as she pulled him back to the playhouse, sun glinting off his hair. As they walked, she chattered on about all the riding equipment she’d found abandoned in the barn’s old tack room, much of it antique.

“I found some interesting items there, more interesting than the side saddle even, and brought them out here thinking we might have some fun.”

He slowed his pace and dropped her hand but continued moving forward. The playfulness of a moment ago was gone. He looked like a man making his way to a firing squad. Suddenly, she wanted to call him back. Call the rest of the afternoon off.

“Casey, maybe…” she scurried next to him. “Maybe we should just remount and ride back now. The stuff in the playhouse isn’t that important.”

She reached out to pull at his arm, but he shrugged her off. “No, Tia, let’s see what you have in there. Let’s see what you found. You’ve been pushing for this all day, have obviously had it planned longer than that. I want to know what’s behind all this elaborate effort on my behalf.”

They entered, blinked to adjust their eyes to the dimness. The front room was nothing but plastic containers of water, leftover firewood from the winter, benches and a first aid kit. After a quick scan of the room, Casey moved towards the back of the structure, ducking through a shortened doorway.

Two Victorian era riding habits hung by the window in the rear room. They were the heavy, elaborate threads worn by women who rode aside back in the day, velvet with satin trim and a short train to fan over the horse’s haunches. Both looked rich, were luxurious to the touch.

Casey stared at them, unmoving. His silence unnerved Tia and she hastened to fill it.

“I found them in a trunk. They’re reproductions. Costumes. Maybe Winthrop Farms served as a movie set at one time? Anyway, they’re still old, though not actually Victorian. I brought them here because, because...I thought…see, Alix, my friend, he’d visit over at my house and sometimes he’d try on my clothes, use my make-up. Just for fun. It was campy. A drag act. He could have fun like that with me.”

Tia stopped. She knew she wasn’t making sense. Casey still hadn’t spoken, but he did move, finally reaching a hand forward to trace the satin trim of one of the riding habits with a finger.

Tia drew a deep breath and started again. “I’m a light sleeper. The floodlight mounted over the barn’s back entrance – the one with motion sensors - is right next to the window in my sleeping quarters. When it kicks on at night, I wake up. I know you’ve been visiting the barn in the middle of the night, Casey.

I know you found those dresses and that side saddle in the tack room long before I did. I know you’ve been taking one of the horses out at night.”

Casey turned sad eyes on her. He’d shrunk as she spoke, head lowering as she recounted his secrets. “I guess I’m pretty obvious, huh? Not so clever as I thought.”

She slipped an arm around his waist, was relieved when he didn’t resist. “You were not obvious at all. Even after finding all the clues in the tack room I don’t think I would have put it together if it weren’t for my friend Alix.”

He leaned more heavily against her, his arm coming across her waist so that they were linked at the hip, side by side. “It’s not quite like that for me, Tia.”

His long, narrow fingers again pet the fabric of the riding habit. “I’m not that pan-gendered, multisexual whatever that you mentioned. I do imagine myself as a woman, imagine myself in flirty skirts and high boots and snug sweaters, looking hip and sporty. I have a woman’s soul, Tia.”

Tia swallowed. Alix had never spoken quite like that, as if he were a woman. He’d been all about the fluidity, about gender as a drag act, whether it was male drag or female. She’d been so clever, thinking a small town girl like herself recognized what Casey was going through but he was a whole different flavor of queer. She wondered how far he’d take the woman thing. She imagined him dressed up, transformed, features fully gentled into femininity and still felt that same, urgent quickening between her legs. Clearly whatever appeal he held for her wasn’t going to be easily diminished.

“So now that you know a little more about me, are we still on a date?” Casey interrupted her thoughts with the hopeful question.

“We’re absolutely on a date, my girl. Can I say that?”

Casey nodded. “I think I could get used to hearing that. And I should tell you that you look very handsome today. Smashing.”

“Thank you,” Tia gave Casey a little bow. “So what do you say? Shall we finish our ride this afternoon? You riding Blue and me riding Eclipse? And what about the women’s habit. Yea or Nay?”

Casey’s small smile grew bigger, easier as she spoke. “You really are something else, Tia.”

Once more she launched him into the saddle, this time to ride aside on Blue. He’d decided to remain in male attire, not comfortable wearing women’s clothing so openly in the daytime, even on the deserted estate. He settled in easily and she made some adjustments to the stirrup. “We’re lucky the saddle fits. Who have you been riding at night? Certainly not Eclipse. He’s much too large.”

“Mind the Gap. The old girl was shocked, I’m sure, to find herself chosen over all the younger thoroughbreds in the barn. I think she enjoyed coming out of retirement for a few hours a week.”

Tia chuckled as she lowered the stirrup so that she could mount Eclipse. Once she was situated they moved off, this time across the open pastureland. They again fell into the easy conversation of lunch. Tia enjoyed riding Eclipse, particularly the height the horse gave her over Casey when he was on Blue.

She watched him, surprised at his awkward equitation in the side saddle. He clearly had some familiarity with it, but he was unnaturally stiff. She tried giving him some pointers, but he only looked more ungainly.

“You’re not relaxed. And square up in the saddle, just as if you were astride.”

He frowned. “I don’t know why I can’t get this.”

“You’ve just picked up some bad habits is all. You’re going to have to trust me to break them.”

“I do trust you.”

Tia guided Eclipse close to Blue and leaned down, catching Casey’s lips in a kiss. He responded, moving his mouth under hers enthusiastically. Only the impatient shifting of the horses drew them apart. “Let’s try a faster gait.”

They pressed their mounts forward. Casey started finding his form in the side saddle at the faster speed.

The sun had dropped and the watercolors of evening surrounded them as they walked the horses back to the playhouse. Once there, they silently they tended to the horses, then entered to collect the remains of their meal and tidy the place.

“Are you going to leave these here overnight?”

Tia ducked into the adjoining room to find Casey again eyeing the women’s riding habits with admiration.

“Did I tell you how stunning you looked on Blue by the end of the ride? Gorgeous. Perfection. You were the definition of elegant beauty on that side saddle today.”

“Yes. You did mention that once or twice, but tell me again. I don’t think I’ll ever hear that enough.”

Tia stepped closer and brushed a light kiss to the back of Casey’s neck, felt the loosening of his frame, his pliability under her hands.

“You’re perfect, my girl. Now...as you’ve noted, I put a lot of planning into this day…”

Casey’s breathing had deepened. He remained facing away from Tia as she continued caressing his back. One of her hands rested on his side, just below the ribcage. With the other, she withdrew an item from her pocket and held it in front of him. “I came prepared for the night too, if you’re interested.”

His breath caught and then deepened again. His hand closed over the foil covered condom in her palm. “You really go for it, don't you? Tally-ho! and all that. I've never met anyone quite like you."

"Is that a yes or a no?" Tia held her breath, not sure if he'd just complimented her or not.

"Yes. I'm interested."

He turned and caught her up against him even as she moved to do the same. Their mouths fell on each other, eager and open. They traded dominance or maybe desperation, taking turns with attentions that elicited shivers and sighs and groans. They sank down to the cheap plywood floors of the playhouse. Tia had planned to use a ground cloth brought for the picnic or maybe a saddle blanket if they got this far.

As it transpired, they didn’t bother to seek out either, instead spreading out the velvet riding habits on the floor. Tia separated herself from him only long enough to stand and strip off her riding boots and pants and pull the same off Casey. When she returned, she knelt over him, watched his eyes grow heavy and deep as she covered him, drew him inside.

They lay on their sides afterwards, each seeking to balance their bodies on the relative softness of the dresses. Casey drew the pads of his fingers along her arm and shoulder, tracing the defined musculature. The fingers ended up in the short locks of her hair and tugged her forward for another kiss. “I would say your ravishment of me was an unqualified success.”

Tia smirked. “I hate to tell you this mister, but as a woman, you’re easy. Loose. A floozy.”

Casey chuckled. “I’m the woman of my dreams then.”

Tia laughed and pinched his rear. They grew silent, Casey seeming to doze lightly in the gathering darkness. Tia thought back over the day, back over all she now knew about Casey. There was more to him than she’d thought and she was anxious to have one more question answered. She’d wondered at it all afternoon, but it was easier to ask the question into the darkness.

“Casey?”

“Hmmm.”

“You talked about being the woman of your dreams. Do you think you ever will? Do that? Everything that’s involved with becoming a woman? I don’t even know what that would be…hormones and surgery and tons more, I imagine.”

Casey stared into the darkness, continuing to lightly stroke her arm. “Yes. I’ve thought about all that. Came really close to starting the process in college. That’s why things are so strained with my father, by the way. He found out about some purchases I’d made and I decided to come clean when he asked his questions.”

“Oh. Wow.”

“I don’t know what I’m going to do about it all, Tia. Some days I can hardly think about anything else except being a woman. Not just roleplaying at midnight, but living as a woman all the time. 24/7.

Then I’ll go days, even weeks, with hardly a thought in that direction. I don’t know how things are going to turn out for me.”

Tia was quiet for a long time then leaned over and gently brushed Casey’s lips. “I hope I’m around to see whatever it is you decide to do.”

He stood and pulled her to her feet. “We should think about heading back.”

She winced a bit as she moved to collect her clothing. “Just so there’s no confusion, I’m calling the side saddle on the way home. I think I’ve had enough of riding astride for the day.”

This time it was Casey’s arms circling her as she started to dress. “Did I tell you what a handsome, stately figure you cut on that horse?”

Tia grinned and answered his question with a kiss.

It was a very late, very dark ride when they finally led the horses back along the bridle path to the house.