Stranded in Heels Pt. 03

Story Info
Sarah meets Doug's family.
4.1k words
4.7
3.6k
4

Part 3 of the 4 part series

Updated 04/14/2024
Created 03/23/2024
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Fran_cd
Fran_cd
342 Followers

"So how much time to I have to get ready?" Sarah asked. Doug was pulling her big suitcase-on-wheels towards the bedroom while Sarah carried her overnight bag, her make-up case, and her shoe bag.

"You have plenty of time," he told her. "How long did you say you stayed at your friend's cabin at lake?"

"I went there Thursday afternoon, so two nights plus most of the day yesterday," Sarah told him.

"And you needed all this shi... stuff for that long?" he asked as he looked at all of her bags.

"I'd have brought more if I'd known I was going to be stuck here," she told him, laughing. "So, how long... in hours?"

"Hour and a half or so," he told her. "You don't have to rush, but you can't dawdle. I know how long women can take getting ready to go somewhere."

"You know how long normal women take," Sarah told him. "Women like me have to work a little harder at it."

Doug laughed. "Oh, yeah. I keep forgetting about that."

As soon as he was out of the room Sarah started taking her clothes out of the suitcase to hang them in the closet to de-wrinkle. She looked at each outfit, trying to decide which one would be perfect to wear to meet Doug's unsuspecting family. Fortunately she didn't always like to dress sexy... sometimes she liked feminine comfy-casual.

She stripped off her borrowed clothes and her bra and panties. Again Annie gave her an odd look when she took her wig off. This time she put the wig on a Styrofoam head from the suitcase and set it in the bathroom so the steam would, hopefully, renew some of her curls.

She ran a hand over her lower calves and felt stubble. 'Not bad, but shave anyway,' she thought to herself as she grabbed her razor, her body wash, her body scrubber and her moisturizing lotion from the make-up bag.

Sarah stood and let the warmth of the water envelop her body for a bit. She needed to relax. She'd been around people who didn't know she was actually a man many times over the years, and had never had any problems. As she thought about it, she realized that she wasn't worried that her being read by Doug's family would cause her problems... she was worried about it causing Doug problems.

She shook her head. 'He's a big boy,' she thought to herself. 'And he didn't have to include me in the lunch plans. He could have left me here with the dogs.' But she knew he couldn't do that. He was too much of a gentleman to do that. And a cute gentleman, at that... even if he was a couple of years younger than her.

She carefully shaved her legs and armpits and the small patch on her chest where hair wanted to grow. She also made sure her pubes and her ass crack were smooth. Before she rinsed she put a handful of soap in her hand and rubbed it around her small cock and balls. She didn't really jack off like most men... she rubbed her palm on her hard little dick until she felt the euphoria she needed and spurted a handful of her own cream into her hand. 'There,' she thought to herself. 'Maybe that will help to control those naughty thoughts about Doug!'

As she rinsed the soap from her body she inhaled the sexy fresh scent of the natural soap. She didn't use scented soap because she would soon spread a cucumber-melon lotion over most of her body.

The act of putting lotion on her legs and then her arms and finally her chest were a ritual she'd learned watching her mother after a shower. Before she was old enough to realize that she was not a girl she loved to watch the way her mother put the lotion in her hands, then almost lovingly applied it to her long, shapely legs, even up her inner thighs. And then after she put it on her shoulders and arms the put just a little more in her hands and rubbed it all around her breasts, using one hand to lift them so she could put the lotion in the crease under them with the other.

Of course, Sarah didn't have to do that part, but she still made lotioning her breasts a part of her ritual. While she waited for the lotion to soak in she leaned into the mirror to look closely at her face, looking for a stray hair that might need to be plucked. When she didn't find any she reached for her wig and adjusted it on her head, then used a pick and her fingers to fluff out the curls. She usually would wait until after she had her make-up on to put the wig on, but she didn't want to take a chance on Doug barging in and catching her without the wig.

Back in the bedroom she looked through her clothes, still trying to decide what to wear. She wanted to be stylish and feminine, but not sexy. She wanted to wear a pair of thin leg black pull-on pants and a 3/4 sleeve tunic, but when she pulled them out of the closet they were wrinkled from being in the suitcase. 'I'll just have to ask Doug to let me throw it in his dryer to fluff them out,' she thought to herself.

She went back to the suitcase and chose a light pink lace bra with matching spandex thong panties, and a pair of sheer black control top pantyhose. The wide thong on the panties nestled nicely between her round cheeks so she wouldn't have a panty line in her pants. She had thought about wearing just the hose without the panties, but she remembered last night when her hose were wet and cold and she wanted to take them off. She didn't want to run the risk of having to go commando around Doug's family, even if she was wearing pants! She put a wide feminine pad in the front of the panties to further smooth her 'pussy profile', as she and her friends called it.

She was standing in the bathroom in her bra, panties and hose, leaning over to start putting on her make-up, when Doug knocked on the door and opened it slightly.

"Sarah, I made a fresh pot of coffee if you want a cup," he called to her.

"Oh, that would be wonderful," she answered him.

"Are you decent?" he asked as he pushed the door a little further open.

"Not really, but if you have hot coffee come in anyway," she laughed.

She walked towards the door as it swung open. Doug stopped short and sloshed a little coffee out when he saw her. "Uh, well, almost decent," he laughed, trying not to stare.

Sarah saw him look at her crotch, where he was probably expecting a bulge. "Oh, come on, Doug. You have a mom and two sisters. Don't try to tell me they never ran around in their bras and panties and hose."

"Uh, yeah, but they were my mom and sisters," he blushed. "You're not."

"I'm sorry if I embarrassed you," she said as she took a sip of the coffee. "Oh! Do I detect a hint of bourbon in my coffee?"

Doug smiled. "Yeah. I thought you might be a little nervous about all this."

"A little nervous is an understatement," Sarah laughed. "Thank you for the shot of 'courage'."

"There's more if you need it," he said.

"You have a washer and dryer, don't you?" she asked.

"For clothes? Yeah, but you don't have time to do laundry before we go."

"Oh, I know that," Sarah laughed. "I just need to fluff my outfit. It's been in my suitcase for two days."

"Oh," Doug laughed. "Well, I can toss them in the dryer for you. I also have an iron and ironing board, but you have to do your own ironing."

"No ironing for me," Sarah laughed. "I'm a fluff 'em and wear 'em kind of girl." She handed the pants and tunic to him. "Thank you very much. I'll get them out when I'm done with my make-up."

Doug took the clothes from her without looking at them. He was again looking at her 'profile'. When he knew she caught him he blushed and turned to the door as Sarah turned to go back into the bathroom.

"Oh, Doug?" Sarah called before he was out the door. He turned to look at her. "Here's the other side," she giggled as she bent slightly at the waist and wiggled her hosed and thonged ass at him."

"Very nice," he said as he walked out without bothering to close the door.

Sarah smiled as she put her make-up on. She thought about what all had just happened. Doug was obviously curious about her body. And he had showered and shaved and put a clean western shirt with snaps and nice jeans. He looked good and he smelled good. She knew she shouldn't be thinking about it, but she hadn't had a good time with such a good-looking man in quite a few months. She felt a stirring and was glad she had the feminine pad in her panties and the control top hose over them.

She put a short robe on to go out to get her clothes. Doug was sitting at the breakfast bar with a cup of coffee. "Did you put a little bourbon in your coffee, too?" she asked as she went to the coffee pot.

Doug grinned. "Just a touch," he said.

Sarah poured her coffee, then took the pot to refill Doug's cup. "More bourbon?" she asked when she noticed the bottle sitting on the breakfast bar.

"Maybe just a little," he said, reaching for the bottle. Sarah set her cup down beside him, and he poured a little of it in her coffee, too.

"Ok, Doug, be honest with me. If it's making you nervous to take me to your mom's for lunch I don't have to go. I'll be just fine sitting around here and watching a chick flick on tv while you're gone."

"Oh, I'm not really nervous about taking you over there," he said, smiling at her. "I just don't want them to say something to embarrass you."

Sarah laughed. "That's funny," she told him. "Earlier I thought I was nervous about going, then I realized I'm worried about it causing problems for you if they read me."

He turned to look at her. "That's nice of you," he said, looking into her face. "But don't worry about me." Their faces were only a few feet apart. Sarah had to fight the urge to lean in and kiss him. She didn't know he was fighting the same urge.

"Uh, so where are my clothes?" she asked, turning away from him.

Doug coughed and cleared his throat. "Laundry room is right next to the door to the garage," he told her, pointing.

Doug watched her walk away, the image of her in just her bra, panties and hose still burning in his memory. He hadn't had a girlfriend in a while, and he hadn't even had a chance to get into town to have some fun with a woman in almost two months. He tried to stop thinking about having fun with Sarah. She wasn't even a woman! But when he saw her in just her underclothes, and he looked at her crotch and it looked like the crotch of a real woman, a sexy woman, his mind started going wild. He knew he needed to fight those urges... but he wasn't sure why.

Sarah nodded her head and walked that way. She could almost feel Doug's eyes on her ass as she walked away from him. She made sure it was pointed his way when she bent over to get her clothes out of the dryer.

She took her coffee and her clothes back to the bedroom, and minutes later came back fully dressed, earrings in, bracelets on, necklace laying just above the fairly low neckline of her top.

"Um, are those the 'snow boots' you were talking about?" He asked when he saw her shoes. He made air quotes with his fingers when he said it. Her shoes were black ankle boots with gold laces and a zipper up the inside. They had slightly pointed toes and two inch spike heels.

Sarah laughed. "No, these are the ones I will wear when we get to your mom and dad's house," she told him. "I'll wear my snow boots over there and change when I get there. I just wanted to make sure this whole outfit is ok. It's not too slutty for your mom with the heels, is it?"

Doug laughed. "No, you're not too slutty for my mom. In fact, you're probably more conservative than my mom will be."

"Good," Sarah smiled. "I don't want her to get the wrong impression of me. I'm a school teacher, you know? We have to watch our reputation."

Doug laughed. "You have no worries there. Oh, by the way, did I tell you that my sister is the principal at our local high school? She was one of those literature teachers we didn't like before she was a principal."

"Nice," Sarah said. "At least we'll have a little in common."

"And my brother-in-law, her husband, teaches Algebra I and Algebra II," Doug laughed.

"Wow. It gets better and better. By any chance were either of your parent's teachers?" Sarah asked.

Doug grinned and nodded. "Dad taught middle school science and coached football and basketball. He was able to take early retirement five years ago after he had a heart attack. Mom was the school secretary for most of the time me and my sisters were in school. When dad retired she decided to stay home and take care of him."

Sarah sighed and downed the rest of her coffee/bourbon. "This could be interesting," she said as she went to change into her snow boots and put her ankle boots in a bag.

The snow had stopped when Doug backed out of the garage in his big four-wheel drive truck. The dogs ran in and out of the garage door and bounced around watching them back out. "They don't understand why they can't go with us," he explained. "Usually when I use this truck I'm doing work around the place and they go with me."

"So are they just stuck outside in the cold while you're gone?" Sarah asked with a little edge in her voice.

"Relax," Doug laughed. "They'll go over to the barn and hang out with the rest of the animals. It's not as warm as in the house, but it's warm and dry and there's water. And they will be on guard if anyone or anything comes around that's not supposed to be here."

Sarah nodded. "Okay," she said. "As long as they can get warm."

Doug laughed. "I told you, they were bred for this weather. They love this."

Sarah sighed. "If you say so."

Doug smiled as he deftly maneuvered the truck on the slick roads. Sarah was able to look at the scenery for the first time without it snowing. I was idyllic, with the barbed wire fence and trees and fields covered with snow.

"This is beautiful!" she said softly.

"You should see it when it's not all covered with snow," Doug said proudly.

She looked over at him. "I'd like to, sometime," she said.

He nodded. "Okay."

Sarah's stomach fluttered when Doug pulled off the street in front of a long ranch-style house on the outskirts of the small town he called home. He looked at her and smiled. "You ready for this?"

Sarah smiled nervously and nodded. "I guess I have to be, don't I?"

Doug got out and came around to her side. The drive was mostly cleared of the snow, but still slick. She opened her door and put both feet out to slide out in what she hoped was a ladylike manner. Doug reached up to help her to make sure she didn't slip.

Sarah saw Doug's mother come out on the porch. "Don't you let her slip on that ice, Douglas!" she called to them.

She looked at him and smiled. "Yes, Douglas, don't you let me slip! And can you hand me that bag with my other shoes, please?"

"I'll do my best, mom," Doug laughed as they walked gingerly to the part of the sidewalk that was cleared and salted.

Sarah smiled at the woman as she walked onto the porch. "Hi, Mrs. Butler. I'm Sarah Thompson."

Mrs. Butler took both of Sarah's hands. "Hi, Sarah. Most folks around here call me Emma or Miss Emma. The ones that don't call me mom or grandma, that is. Did Douglas get your car out of the ditch? Is it wrecked bad? You're not hurt, are you?"

Sarah squeezed her hands and smiled. "Yes, my car is out of the ditch. No, it's not wrecked, I was going really slow when I slid off of the road. And, no, I'm not hurt. And I'd be honored to call you Miss Emma."

Emma nodded. "Good. You come on in here where it's warm." She held Sarah's hand and led her into the house.

As they walked in another woman turned and smiled. "Hi, Sarah, I'm Dani," she said. "Welcome to Sunday Dinner!"

"Hi, Dani," Sarah said. "I'm honored to be here. And thank you for the use of your coveralls and boots this morning."

"Oh, you're welcome," Dani laughed. "When Doug told me what was going on I knew you couldn't go get your car without them."

Emma still held Sarah's hand. "Sarah, this is my husband, Bob. A lot of folks still call him Coach." Bob stood and offered his hand to her. "Please, call me Bob," he said. "I haven't coached in years."

"Oh, but I know how it is," Sarah laughed. "Once a coach, always a coach."

"You sound like you know a coach," Bob smiled.

"She probably knows several," Doug said. "Sarah teaches high school in the city."

"Oh?" Dani said. "What district?"

"PC," Sarah said, naming one of the larger districts in the metro. "I've been at PC West for eight years."

"Oh, PC West," Bob said. "So we probably have some mutual friends."

"I'm sure we do," Sarah said, suddenly realizing that that could be a bad thing.

Sarah was introduced to Dani's husband Jimmy, who was watching a football game, and her two sons who were sitting in the floor leaning against a wall playing games on their tablets. Jimmy looked up and smiled and waved. The two boys barely acknowledged she was there.

Sarah stood by the door and slipped her feet out of her snow boots. Doug noticed that she had a toe ring on the middle toe of her right foot. Pretty women with pretty feet were a weakness for him. Sarah reached into her bag for her ankle boots and slipped her feet into them, then stooped down to zip them.

"Oh, those are cute," Dani said when she noticed what Sarah was doing. "But as you can see shoes are optional around here!" She looked down at her own stockinged feet.

Sarah noticed that Dani and Emma both were in their stocking feet and assumed they had come home from church and kicked their heels off.

"Well, as a guest I wouldn't feel comfortable," Sarah said. "But, thank you!"

"Okay, everyone, come to the table," Emma called to them. "Boys, if ya'll want to eat on tv trays you need to get them out."

"Yes, Grandma," they both said.

The meal was nice and the conversation pleasant. Dani and Jimmy asked Sarah about what she taught and were impressed when she told them. Jimmy said he'd like to get her input on how to teach a particular Algebra concept and they agreed to talk after the meal.

Dani started to clear the dishes, and Sarah reached to help her. "You don't have to do that," Dani said. But she didn't protest when Sarah started to carry dishes to the kitchen.

"So, does my brother know you're trans?" Dani asked quietly when she and Sarah were standing shoulder to shoulder at the sink.

A chill ran up Sarah's spine. "Yes," Sarah said. "He's pretty smart. He asked me if I was a man."

"How'd he react?" Dani asked.

"Pretty well, I'd say," Sarah told her. "He wanted to ask questions, and I let him."

Dani nodded. "Doesn't surprise me," she said. "He's usually pretty open-minded. So do you teach as a man or a woman?" Dani asked.

"Oh, a man," Sarah told her. "This is a lot of work. I don't want to have to do it every day," Sarah giggled."

"I know, right?" Dani said. "I hate having to put make-up on every morning."

They finished the dishes and joined the others in the living room.

"Sarah, I'm going to have to head back home to see to the animals soon," Doug told her.

Sarah nodded. "Okay. Between the stress of last night and that wonderful meal, I could use a nap!"

"Now Sarah, we have extra bedrooms here," Emma said. "You might feel more comfortable here with me and Bob."

"Oh, thank you so much, Miss Emma, but all of my stuff is at Doug's. And hopefully the roads are going to be clear enough for me to head back to the city tomorrow," Sarah said. "Besides, I have a guard dog at Doug's."

"Oh? Which one," Emma asked.

"Annie," Doug answered. "She's been right under Sarah's feet since we got there last night. Even slept in the guest room with her."

"Annie?" Dani asked, giggling.

Doug gave his sister a look. "I know she usually doesn't take up with women," he said. "But for some reason she likes Sarah."

Emma nodded. "She's a smart dog!" she said, smiling. She looked at Sarah. "She likes me, too."

"That's true," Dani said. "She won't have anything to do with me, but when mom is out there Annie is right with her wherever she goes."

"Well, I feel honored again," Sarah said, smiling. "And I feel totally safe staying in Doug's gorgeous home another night. He's been a perfect gentleman and a perfect host."

Fran_cd
Fran_cd
342 Followers
12