Stranded in Heels Pt. 02

Sarah looked over her cup as she took a bigger drink of her coffee/bourbon. Here it was. The moment of truth. She hoped her voice sounded calmer and cooler than her stomach felt.

"Well, by most definitions of what a man is, no I'm not a man. But... I am male. I live most of my life as a male. I work as a male. But no matter how I'm dressed, I am Sarah. I consider myself to be a transgender woman. I've felt that way since I was very young, I just didn't know what it was called until I was in high school."

"So what tipped you off?" Sarah asked. "I mean, I know I'm no beauty queen, but I thought I was doing a pretty good job of passing tonight.

"Passing?" Doug asked.

"Looking like a real woman," Sarah explained.

"Oh, you are," Doug said. "You are very pretty, and you look like a real woman. It was Annie," he said, nodding to the dog.

"Annie?" Sarah asked.

Doug laughed. "I told you, she doesn't like women, but she likes you. That made me look a little closer. I still couldn't tell for sure, so I had to ask."

Sarah reached down to pet Annie's head again. "You big old tattletale!" she laughed. Annie's tail wagged. "Well, at least you had to ask. If it hadn't been for Annie, would you have asked?"

Doug shook his head. "Probably not. Like I said, you look like a very real very pretty woman to me. You need another cup of coffee?" he asked as he stood up.

Sarah drained her cup then put her hand over the top of it. "No, I've had enough coffee, and definitely enough bourbon," she said. "Did you say you have hot chocolate?"

"Hot chocolate it is," Doug said. "You won't be offended if I have more bourbon?"

"Not at all," Sarah said. "Just because I'm a lightweight doesn't mean you have to be."

Sarah sat silent, watching as he poured hot water over the packaged cocoa and then some bourbon, without coffee this time, in his cup.

"So, you were talking about your friends and your party at the lake and how you all didn't have dates," Doug said as he set her cup on the bar in front of her. "Um, all, uh, ladies like you?"

Sarah nodded. "Yes. All ladies like me."

Doug nodded and sipped on his drink, staring out the window into the darkness.

"Listen, if this is making you uncomfortable I'll finish my hot chocolate and go to bed. Tomorrow morning you can take me back out to my car and help me get it up on the road and I'll be on my way," she said.

Doug shook his head. "You don't make me uncomfortable. I have questions and I don't want to be rude."

Sarah laughed. "Honey, you can ask me any question you want. You won't hurt my feelings. Believe me, I've heard them all."

"So, um, you have all male, uh, parts? And they all work?" Doug blushed as he asked it.

Sarah giggled. "Yes, I have all the parts, and they all work. And I don't plan to do anything to change that."

"So, you mean, no surgeries, or taking female hormones and such?"

"Well, I do take some female hormones," Sarah admitted. "I started them about a year ago. A light regimen prescribed by a doctor, which will hopefully cause my boobs and nipples and hips to grow and give me more of a feminine figure."

Doug raised his eyebrows and looked at Sarah's chest. "They seem to be working."

Sarah laughed. She unbuttoned the top button on her satin blouse and reached in to pull a c-cup sized silicone breast form out. "Now you can say you've seen my left tit," she giggled as she held it up for him to see before she stuffed it back into the cup of her lace bra.

Doug laughed with her. "So I have," he said. "Ok, so have the hormones had any effect on you?"

"My breasts are a little puffy, and my nipples are definitely bigger and more sensitive than they were a year ago," Sarah told him.

Doug nodded. "Okay. What about, um, down below?"

"There have been some small changes. I wasn't exactly a stud before," Sarah giggled.

Doug laughed. "Okay. I won't ask any more about that. Well, except... uh, does it still get, uh..."

Sarah laughed. "Yes, it will still get hard, it just takes a little more work than it did before the hormones. And, yes, I can still have an orgasm and I still ejaculate, but it's not as much and it doesn't shoot out like it used to, but it still feels good, maybe even better."

"Wow, you are not bashful about talking about it," Doug laughed.

"No, I'm not," Sarah said. "To be honest, there's a lot of misconception about trans-women in the world, and when I find someone who is asking honest questions and seems genuinely interested in the answers I will answer them. So, like I said, ask away."

"Ok, for sex...?"

"I don't have casual sexual encounters," Sarah told him. "I know a lot of people think trans-women, or all gay or bi people, are just cock hungry sluts looking for a dick to suck. I'm not that way, nor are most of my friends. I do love sex with both men and woman when the time and the feeling are right."

Doug raised an eyebrow and smiled. "At the same time?"

Sarah laughed. "While that has happened a few times it's not my norm," she said. "I'm usually a one on one type person."

"Do you have a preference?" Doug asked.

"Yes. I prefer men. Maybe because it's easier for me. There's not that many women out there looking to date a lady like me... or me in my male mode. And, pleasing a man makes me feel like a woman, and, well, I like that," Sarah told him.

Doug nodded. "Makes sense." He drained his drink and stood up. "Well, Sarah, I need to be up early to check on the animals again. There will be coffee in the carafe. If you get up while I'm outside help yourself. I'll fix us some breakfast when I come back in."

Sarah smiled. "Okay. Thank you for the bourbon and the coffee. It really warmed me up! Um, Doug, could I trouble you for one more thing?"

He stopped and looked at her. "Sure."

"Well, all of my night clothes are in my suitcase, in my car. Do you have a t-shirt I could sleep in?"

Doug smiled. "Sure. Come on. Time for you to see the master suite."

Sarah and all three dogs followed him down the hallway. Sarah whistled when they walked into the big room. It was even bigger than the room she would sleep in and had a little add-on sitting room. There was a fireplace in one outside wall, and the other was all windows. There was a big rug in front of the fireplace where two of the dogs settled as soon as they walked in.

Doug opened a drawer and pulled out a white v-neck t-shirt. "Will this work?" he asked.

Sarah took the shirt and held it up to her body. "I think I have a dress shorter than this," she laughed. "Yes, it's perfect. Thank you." She turned to leave the room. "Good night, Doug. Sleep well."

"You, too," Doug smiled.

Sarah stopped in the hallway and looked back at Annie. "You coming with me?" Annie's tail wagged as she followed Sarah towards the other bedroom.

Sarah went into the bathroom in 'her' bedroom to wash her face. She hated to wash all of her make-up off since she didn't have anything to put back on in the morning, but she didn't want to get make-up smears on the nice pillow cases on Doug's bed. She also hated that Doug would see her in the morning without make-up, and that might scare him!

Annie cocked her head and looked at Sarah when she took her wig off and laid it carefully on the nightstand. "At least my hair will look good in the morning," she said to the dog.

Sarah snuggled in under the heavy blankets on the bed while Annie settled down on the rug beside the bed. Annie's tail wagged a few times when Sarah said "Night night, Annie."

Sarah opened her eyes and looked around, trying to remember where she was. Slowly the events of the previous day and night came back to her. She sat up on the side of the bed and reached for her wig.

"Good morning, Annie," she said to the dog who still lay on the rug beside the bed. She went to the bathroom to pee and put her wig on. She looked at her face and frowned. She hated for Doug to see her with no make-up, but it couldn't be helped.

She looked down at the t-shirt she'd slept in, trying to decide whether or not she should put her blouse and skirt back on. The t-shirt reached to the middle of her thighs, about the same as most of her nightgowns. She decided go get some coffee in the t-shirt.

The house was quiet. Doug must still be out taking care of his animals. She poured herself a cup of coffee and sat at the breakfast bar and looked at her phone. She had a message from Danielle that had come in last night. "Okay, honey. Thank you. xoxo"

She noticed her purse still on the breakfast bar where she'd left it last night. That was unusual for her. Normally she would take her purse to the bedroom with her. That she left it on the bar indicated she had felt very comfortable with Doug when she went to bed.

She smiled when she remembered that she had a lipstick and some matte powder in the purse. She patted some of the powder on her face to at least get rid of the shine, then used the tiny mirror in the compact to put some color on her lips. On a whim she put a dot of red lipstick on each of her cheeks and rubbed it in to give her cheeks some color. She looked at herself in the tiny mirror and smiled. It wasn't as good as last night, but it was better!

When she went to get her second cup of coffee she decided to see what Doug had to cook for breakfast. She wasn't sure why, but she felt comfortable checking out his refrigerator and cupboards.

She found bacon and eggs and a frying pan and put them on the counter next to the stove. She found the bread and the toaster. She found the utensils she would need to make Doug a hearty breakfast. She decided to start the bacon. After she put it in the pan on the stove she reached up into the cupboard to get some plates and glasses. She had to reach over her head for the glasses.

She heard the door open, and then a whistle. "Whoa, nice! That's not what I expected to see when I walked back into the house!"

"Thank you," she said. She realized the t-shirt had pulled up when she was reaching for the glasses, exposing her panty covered butt. She blushed and pulled the shirt down. "I'm sorry. I didn't mean to flash you. I thought I would start some breakfast, if you're okay with me cooking for you, that is. How do you want your eggs cooked?"

"I'm totally okay with the flash," Doug laughed. "And I'm even more okay with you cooking for me. I'll take my eggs over medium, please."

He peeled his coveralls off and left them by the door. He leaned against the breakfast bar to watch her cook, enjoying the view of her long legs and pretty feet and the occasional glimpse of her panties.

"You want bourbon in your coffee this morning?" Sarah asked as she poured coffee into his cup and put it on the breakfast bar. "So it's not snowing as hard?"

"No bourbon in my coffee this time," Doug laughed. "Not as hard, but still coming down. And it's changing to sleet. I moved my other truck to the barn so you can park yours in the garage when we get it out of the ditch."

"Wait, what?" Sarah asked. She turned around to look at him. "I don't need to park in your garage. I'm going to head back into town when we get my car out."

Doug shook his head. "You're not going anywhere today," he said. "The turnpike is still closed."

"So when are they going to get it open?" she asked. "I really need to get back to the city to get ready for work."

"Not sure when they'll get it open," he told her. "I've got a cb radio in my truck. While I was moving it over to the barn I talked to some truckers up at the turnpike entrance. Nothing is moving. The turnpike is refreezing so fast they've stopped trying to clear it. If this does turn to sleet it could last a few days."

Sarah sighed. "I guess I need to get in touch with my principal and let her know what's going on."

Sarah noticed the bulge in the front of Doug's jeans that wasn't there when he first came back in the house. Doug saw her glance at it.

"Probably not going to be an issue," Doug said as he turned to face the breakfast bar to sip his coffee. He thought he noticed a smirk on Sarah's face when she glanced at the front of his jeans. "They're getting it worse in the city than we are here. I doubt they'll be having school for the next few days. Uh, listen, I'm going to go find some sweats for you to wear. I'm sure your legs must be cold."

Sarah shrugged. "I'm fine. It's pretty warm here in the kitchen."

"Uh, well, still, um, you need to put some pants on," he said as he walked down the hallway.

Sarah smiled. She thought she knew why he wanted her to put some pants on. 'Hmmm,' she thought to herself. 'This might be an interesting few days!'

She was just putting their plates on the breakfast bar when he came back with a pair of elastic waist sweat pants.

"These will be a little big on you, but they have a string so you can cinch them up maybe they won't fall down," he said. He put the sweats on her barstool and sat down in front of the plate she'd made for him.

"I'm sure they'll be fine," she smiled. She turned to the side and crossed her legs so that Doug had a good view of her toned upper thighs. "I hope you're okay with having a houseguest for a few days."

"I don't think I have a choice, do I?" he laughed. "I can't very well kick you out in this storm."

She shrugged as she started to eat. "It's not that far to my friend's cabin on the lake," she said. "You could always take me back down there."

Doug shook his head. "I'd rather not try to do that much driving in this mess," he told her. "Great breakfast, thank you," he said. "I'm okay with having a houseguest for a few days."

When Sarah finished eating she put the sweat pants on and started to gather the dishes. She grabbed the coffee pot and refilled Doug's cup.

"If you'll put those in the sink I'll rinse them and put them in the dishwasher later," he told her.

"It'll only take me a minute to take care of them," she said. She felt very feminine and domestic taking care of the dishes while Doug sat at the table and enjoyed his coffee. "So your big truck will be able to pull my car up on the road? Will I be able to drive it to here, or will you have to pull me?"

Doug shook his head. "I'm going to use a tractor to get your car out of the ditch. It gets better traction in the snow and it has a bucket so I can clear the road so you can just drive back here."

Sarah finished with the last of the dishes and turned to look at him. "So are we ready to go?"

"In the bedroom where you slept, in the closet there's a pair of insulated coveralls that should fit you," Doug told her. "They're my sister's. You and her are about the same size."

"And she won't mind me borrowing her clothes?" Sarah asked.

Doug shook his head. "I called her when I was out in the barn and told her what's going on. I told her you don't really have any gear for getting out in this weather. She's okay with you wearing her coveralls and the knee high rubber boots that are in the closet, too."

"That's very nice of her," Sarah said. "Tell her I said thank you."

"You can tell her yourself," Doug smiled. "She'll be joining us for Sunday dinner at my mom's house later."

"What do you mean, joining us?" Sarah asked.

"Well, my mom always makes a big dinner after church on Sunday, and we all eat there. I also talked to mom and told her about you and she said there'll be plenty of food for one more," Doug explained.

"When you say you told her about me..." Sarah said.

"I told her a nice lady slid off of the road and I helped her out and now she's stuck until the weather clears some," Doug told her. "She said that maybe you'd be more comfortable staying with her and my dad until it's safe for you to drive home," he smiled.

"Um, I think I'd rather stay here if you don't mind," Sarah said.

Doug nodded. "I don't mind. Not sure what my mom will think, but I won't mind," he laughed.

"Oh, I didn't think about that!" Sarah said. "Is your mom going to think I'm a slut?"

"Probably," he laughed. "But she won't say anything. So, I'm going to get you a sweat shirt and some long socks to wear under the coveralls. We need to get moving if we're going to get your car back here in time to get ready to go for dinner."

"Oh my god yes!" Sarah said. "I'm going to need to shower and put on make-up and..." She stopped and looked at Doug. "She and your sister are expecting you to bring a woman, right?"

Doug laughed and nodded. "Yes. You're going to need to get all dolled up for it."

"Then we need to get going! Come on! Let's move!"

"So, who besides your mom and dad and sister will be there for lunch?" Sarah asked when they were in the tractor heading to get her car.

"My sister's husband and her two kids. They're 12 and14, both boys. They'll spend most of their time on their tablets while they're there. My other sister and her husband will come if she's off work. She's a nurse at the hospital in Chickasha."

"Will any of them make a fuss if they read me?" Sarah asked.

"I'm guessing that means if they figure out you're a guy," Doug said. "And in answer to your question, I don't think so. I'm not sure what the boys might say, but I don't think they'll pay any attention to you. The others will wonder and wait until they can talk to me in private to ask me about you."

Sarah watched as Doug quickly cleaned a path around her car, then hooked a tow rope to it. "Start it up and put it in neutral," he told her. "Turn your wheels to steer to follow me. When we get you up on the road I'll stop and take the rope off. I'll clear the road and you can follow me back to the house."

Sarah breathed a big sigh of relief when she pulled her car into the empty space in Doug's garage. Even with Doug clearing the way with the tractor the road was treacherously slick. There was no way she could even think about driving back to the city today.