tagTranssexuals & CrossdressersDarker Places Than I Want To Feel Ch. 02

Darker Places Than I Want To Feel Ch. 02


Thanks for taking the time to read my stories. If you're new to this series it would be best if you went back to the first chapter to understand some of the dynamics in this unique relationship. I hope you enjoy this latest chapter of From Darker Places Than I Want To Feel...



Ryan woke up early Sunday morning and opened the blinds on his bedroom window. It was raining. Today was the first time he was going out with someone since his wife died. Today he was going on a date with Sarah. He stopped in the bathroom and gazed at the mirror. He looked a bit haggard. Maybe it was the late night he put in worrying about what was going to happen tonight. Is this crazy? Am I crazy? What would others think? What would they say behind my back?

'He must be out with his daughter; a beautiful woman like her would never go on a date an old guy like that. She must be his daughter.' Or they would whisper, 'could she be a pro? She must be with a guy like that. Look at how slutty she's dressed.'

Ryan had no idea how she was going to be dressed but it didn't matter. He shook the nasty thoughts out of his head. She was beautiful. She asked him out on a date, end of story.

"Fuck'em, fuck'em all."

He decided to clean his apartment. Cleaning things always pushed the dark thoughts out of his mind. Cleaning helped him get through his wife's cancer, cleaning, and cleaning, and more cleaning. He cleaned until the finish was worn off the kitchen counters. It had been a long, slow, and painful journey for her. He decided to start with his office first.

By mid-afternoon the rain picked up again. It dribbled and dripped for most of the morning then started to pour about two o'clock. Ryan had spent most of the day sorting through stacks of old papers and file folders from previous semesters. They needed tossing out. He picked up a stuffed garbage bag filled with discarded paper when his phone chirped. He had a new text message and it was from Sarah.

'Hi, it's yucky out so come to my apartment building and I'll buzz you in. See you in an hour.'

"An hour!?" He glanced at the desk clock. "Crap, I need to get ready." Ryan dropped the garbage bag, a job for another day, and rushed to the back of his apartment to take a shower and dress. The nagging thoughts began again but he shook them off. He really liked being with Sarah and finally he was beginning to believe that he didn't give a fuck what anyone else thought about it. She was a beautiful woman and he was damn lucky to be on a date with her anywhere.


Ryan walked up to the apartment house and pushed the buzzer. Then he looked up to see Sarah looking out the front window of her third floor apartment. She waved to him. He smiled and waved back. A moment later he heard Sarah's voice on the speaker and a buzzer releasing the outer door. "Come on up, I'll be ready in a minute."

Ryan walked up the three flights of stairs to Sarah's apartment, the one she was sharing with her older sister Anna and her two nephews. This was the place where Sarah, after three years of surviving on the street, was finally safe. It took a brutal beating by some twisted pervert to finally convince her to accept her sister's offer, even with all the conditions. Anna demanded that she stop living on the streets. She told her that she couldn't do tricks anymore; she needed to find a real job. And she couldn't tell her nephews the truth about who she was, at least not yet. Anna didn't think that they were old enough yet to understand that their Aunt Sarah used to be their Uncle Simon.

Ryan reached the third floor and knocked on the apartment door. Bobby, Sarah's youngest nephew opened the door.

"Hi Bobby, is Sarah ready?"

"Yup, she'll be right out. You're supposed to wait on the couch." Bobby closed the door behind Ryan and locked both locks as Ryan walked over and sat down on the sofa. Bobby ran back to sit in front of the television. He picked up his game controller and pushed play.

A moment later Sarah walked out of the bedroom hallway wearing a cashmere sweater dress with a simple gold chain necklace and matching earrings. Black patent leather heels and dark hose finished the look.

Ryan stood as she walked towards the couch. "You look lovely tonight." This was a far cry from the baggy pants and ragged t-shirt she wore the first time they met.

She smiled demurely. "Thank you."

"Shall we go? We have a reservation for seven."

"Let me tell Anna we're leaving." She turned and walked to the hallway. "Anna, we're going."

"Just a moment, let me see you off," Anna shouted back from the back bedroom. She walked briskly towards the living room with a huge smile on her face. "Hello Ryan, it's nice to see you again." Anna was shorter than her younger sister but still taller than average. She was slender, her short brunette hair flipped behind her as she walked, and her smile was ever present.

"It's good to see you too." For Ryan, Anna was his teammate in the battle to save Sarah. He took comfort in the fact that she was there to help and she often reminded him of that fact.

"How's the writing going? Have you got an agent yet?"

"The writing is going okay but the agent business is a lot tougher than I thought it would be. Nobody seems to be interested in what I'm writing about. At least I still have my day job," he said with a chuckle. "Patience and courage are two sides of the same coin as the old saying goes."

"Yes they are. I've read that it takes a while to find the right person willing to listen to what you have to say. If there's anything I can do just let me know."

"Thanks Anna, I will." Ryan smiled then turned to Sarah and took her hand. "We should go."

"Bye sis, see you later this evening."


"Bye Aunt Sarah," Bobby said barely able to pull his eyes away from his video game.

As the door closed Ryan could hear Anna. "Bobby have you finished your homework?"


Ryan was amazed at how beautiful she looked as he listened to the click of her heels against the sidewalk pavement. Even though she was dressed rather conservatively, her dress clung to her feminine shape and accentuated her curves the way it hugged her body. She was, indeed, remarkably beautiful.

The latest rain shower left tiny puddles on the sidewalk and even though most of it had stopped a while ago, large drops still fell from the trees overhead. He opened his umbrella like a tiny shelter as they walked to his car.

He glanced over several times and watched her as she negotiated several small puddles along the way. She glanced back at him and he blushed when she caught him sneaking a peek at her. She laughed and entwined her arm in his, pulling him closer to her. That made his heart race faster and he secretly took several large breaths to calm it down.

The restaurant was an upscale Japanese steakhouse called Shogun near the downtown area. She had never eaten sushi before but she told him she liked seafood so he knew she'd like the place. After the waiter, dressed in full yukuta, ushered them to a traditional Japanese table they both knelt down and got as comfortable as one could for a western couple sitting on cushions on the floor.

"This is different," she whispered with a smirk.

"If you're uncomfortable we can go," he offered with an earnest look.

"No, no, it's okay. I think it's going to be fun. Just doing it in a dress is a bit odd. And you're going to have to show me how to use these." She pulled up a pair of chopsticks with both hands and started stabbing at her napkin.

"Here, like this," he chuckle as he demonstrated how to hold them. "If it's too much they do have forks if you want."

"I'll keep that in mind but for now I'm up for the adventure."

Ryan picked up his menu and scanned the offerings. He'd been there before; he knew what he was going to order.

"What's good?" She asked peeking over the top of her menu.

"Just about everything but if you're not into raw fish, then you can steer clear of those dishes by looking for the tiny raw symbol by the description."

"Oh, I see it, okay. What are you getting?"

"A sushi platter, it's what I usually get." He tilted her menu and pointed to the description on the left.

"That looks good, I'll order that too."

"They have Kobe beef here if you're interested."

"Nope, just the sushi platter. I'm not into beef that comes from cows who aren't free range."

"How did you know that?"

"I'm not a dummy, Mr. Sullivan, I read."

"Miss Davies, you continue to amaze me every day," he said gazing at his menu again.

She smiled demurely and stuck her nose back into the menu then she slowly lowered it and looked at Ryan with a winsome smile.

He felt like she was watching him so he looked up. "What?"

She shrugged. "Nothing." She buried her nose in the menu again.

"Okay, you'll tell me when you're ready to tell me."

She sighed and nodded. "I've wanted to tell you something for the longest time but I've never found the courage until now."

"What brought this on?"

"Something you said in the apartment about patience and courage." She peeked over the top of her menu again. "You don't know this but the day we first talked on the phone I was planning to kill myself that night. I had the pills and everything."

All of the color dropped out of Ryan's face. He sat there stunned.

"Your call saved me," she said tilting her head and smiling shyly. "I never thanked you for that. So, thank you."

Ryan nodded then reached across the table and took her hand. "I'm glad you're still here."

Sarah blushed scarlet and dropped her eyes.

A woman arrived dressed in a traditional kimono. She knelt down beside the table and asked if they were ready to order. Ryan looked up and gestured to Sarah who ordered the sushi platter.

"And I'll have the same," he said handing his menu to the woman who nodded and left.

They sat quietly for a few minutes looking at their surroundings. The restaurant was tastefully decorated in traditional Japanese art. Sarah pointed out a couple of screens in particular. "Some of the screens depict traditional Kabuki wood block prints from the Edo period. And over there is a reproduction of a traditional shogun warrior in full battle armor. It was more for show that actual combat although it's not a bad reproduction."

"How do you know so much about Japanese culture?" Ryan asked leaning around to get a closer look at the battle armor.

"When I wasn't working before I moved in with my sister I spent a lot of time in the library," she said with a subtle smile. "Life can get pretty boring when all you do is wait for someone to call."

Ryan's mouth dropped open and then he closed it while shaking his head and chuckling. "I was just thinking how amusing social prejudices and misconceptions are. Amused and disgusted at the same time. Did you graduate from high school?"

"Just barely. I was incredibly bored. All they did was repeat what they said before in grade school and middle school. I get it, the Roman Empire expanded to Hadrian's Wall. Got it. The political destruction of the Tokugawa shogunate in Japan at the end of the Edo period was the direct result of actions by Commodore Perry and the clash of western culture. Okay, got it, let's move on to something new. But no, they just keep going over and over the same stuff. I got bored. I nearly quit but my sister made me finish."

Ryan rested his chin in his hands as he listened to her with a wry smile on his face.


"You're probably smarter than most of the kids I teach at the university. Want to go back to school?"

"Only if I learn something new. If I'm bored, I'm gone."

"I'll see what can be done. Brains and beauty, that's a dangerous combination."

"Only for a criminal."

A waiter brought their dinner and he picked up his chopsticks to point out a few things for her.

"I usually pour a little of this to dip my sushi into." Ryan took a small saucer from the corner of the table and poured a some soy sauce into it. "And the ginger, yes, that stuff there, goes nice over some of the rolls. It helps clean the palate like wine does for western dishes. Oh, be careful of that stuff," he said pointing with his chopsticks at a small green lump of wasabi, "that stuff is wicked hot."

"Really? I like hot stuff."

"Well if that's the case then I've seen some folks mash the wasabi into their soy sauce. Yes, like that. Be careful, it's really hot."

"Or you're being a big wuss." She dipped a roll into her soy sauce and popped into her mouth. "Oh fuck, that's hot!" Sarah downed her cup of tea in one gulp. Several people at other tables glanced over at her as she fanned her mouth with her hand. She wasn't sure if their attention was drawn because of her actions or the word "fuck". She decided it was probably the word knowing Japanese culture like she did.

"Could we have some more tea please?" Ryan asked a passing waiter who nodded and disappeared. Sarah fanned her mouth as they waited for more tea. Then Ryan offered her his cup and she downed that in one gulp too.

"Crap, that is hot." She reached across and smacked his shoulder playfully. "Stop laughing."

"I'm trying not to but I told you so."

"I know but I'm stubborn, remember? I need to use the restroom." She got up awkwardly and dashed off in the direction of the back of the restaurant while Ryan turned back to his meal.

He thought of her comment about being stubborn and remembered the first day he met her. He had done a little background research into transgendered issues before he met her that day and he discovered some sobering statistics.


He scrolled down the webpage on his cellphone. 'If you are a transgender person, there's a seventy percent chance that you will consider killing yourself. If you are a transgender person, there's a fifty percent chance that you will attempt it. If you are a transgender person, there's a thirty percent chance that you will succeed. The facts don't lie.' He closed the browser on his cellphone and sighed. She was late.

He looked down at his shoes as he leaned against a guardrail. Tiny dust devils swirled across the playground as the autumn leaves danced in the wind. Why was she late? This was going to be their first meeting but he was getting worried. Maybe she decided it wasn't worth it after all. He'd been waiting for twenty minutes for her to show up. The playground she mentioned was easy enough to find. Maybe he misunderstood. Maybe she thinks I'm too old, but I told her all about me over the phone. He kicked a small rock near his toe and it scooted across the dusty playground to land at the feet of a young woman standing twenty feet from him.

"Hey. You Ryan? I'm Sarah." She was dressed in baggy sweatpants and a t-shirt that looked a bit ragged, well-worn running shoes, and a baseball cap pulled down to partially cover her eyes. Ryan stood up and waved shyly.

He leaned forward and offered his hand but she stood motionless. "Hi, yes, I'm Ryan, you must be Sarah. Thanks for coming to meet me." He sat back against the railing and shoved his neglected hand back into his pocket.

"Bobby, you and Michael can play on the swings over there. I'll be right here, okay?"

"Okay Aunt Sarah." The two young boys who looked to be no more than ten and nine raced across the park to the swings.

"So, what do you want to talk about?" Sarah asked with a guarded tone that bristled with hostility. She was nothing like the girl he talked to on the phone. It was like she was putting on an act, trying to look mean. It set him back a bit to adjust to her new demeanor.

"Well, like I said on the phone, I would like to talk to you about your life. What it was like to live the way you did. And maybe to share a few details about your experiences."

"Nothing much to say," she said taking a few steps closer and speaking softer. "I fucked guys and they fucked me. End of story."

Ryan assumed that she lowered her voice and moved closer so that the boys couldn't overhear her so he dismissed the obvious threatening overtone. "Can you tell me a little bit about it?"

She shoved her hands in her pockets and shrugged her shoulders. She leaned closer to him again with a subtle sneer. "Sure. I fucked them in the mouth. I fucked them in the ass. I even let a dozen frat boys fuck me when they paid me extra. My mouth and ass were dripping with cum. I loved it, fucking loved it. One time I even tied a couple of boys up and gagged them so nobody could hear them scream while I fucked them. They loved it. Have you ever been gagged and raped? How about I do it to you? Would you like that?"

Ryan stood up and walked a few steps away from Sarah then he turned and stared at her. "If you're trying to shock me, don't bother. If this is some kind of game you like playing, I'm not interested."

Sarah walked towards him seductively. Well as seductive as she could in baggy clothes without makeup. She put a hand on his chest and began to rub him all over. She glanced over her shoulder to make sure her nephews couldn't see her then she started to slip her hand down his pants.

"Is this what you want instead baby? You want a little action?" She stood back and slapped him hard on the face. "Or maybe you're into a little S&M play? Huh? I can do a little Fifty Shades on your ass as soon as the boys head back inside."

Ryan stood like a statue and stared at her. She moved closer and pulled her hand back to slap him again but he didn't flinch, he just stood there. She grabbed his chin and held his face close to hers as he continued to stare at her.

"Well, do you?" she sneered as she stared into his eyes.

Ryan thought about what had just taken place. At first she tried to be mean and angry, then she tried to seduce him. Now she was hitting him, trying to tempt him into some sort of twisted S&M play. Was she doing all of this to try to get a rise out of him? Or did she just see him as another 'trick' to be fucked and discarded? It was very confusing at first. It was if she wanted him to beat her...as if that was the only way she knew how to behave.

"Be quiet and take your hands off of me."

Sarah backed off a few steps and glared at him.

"If this is your response to what we agreed upon then we're through before we even get started. I came here to meet you and talk to you honestly about your life and your experiences. If you see it like some sort of game then we have nothing further to discuss. But if you want to do this, like you said you did, then you need to stop the bullshit and be honest with yourself and with me."

"As frightening as it sounds, you are just going to have to trust me. I won't beat you; I won't try to fuck you. I just want to talk to you honestly and openly about your life. I know it might be a bit daunting; perhaps more distressing than anything you've ever done before." He paused a moment. She dropped her eyes and began to shake her head slowly.

"Because to be brutally honest with yourself, to drop all the pretenses and peal back all the bullshit that we wrap around us in order to protect ourselves from the truth of who we really are, is terrifying. You can say no at anytime and it's over. I will walk away and we will never speak again. That's the only control I'm willing to give you. Is that what you want?"

* * *

Sarah looked down at her feet and nudged a rock with her toe. She looked up and squinted in the afternoon sun then she shielded her eyes and looked at Ryan. She felt like shit for acting the way she did. Deep down inside she knew that she needed this more than he did. Somehow, she knew that talking about her life with Ryan, a complete stranger willing to listen, was exactly what would keep her alive. And she wanted to be alive. Maybe it would help her exorcise all the demons that clouded her mind, the ones that wanted her to end it like she planned to do before she met him. She turned her head and sighed. I'm so fucking stupid, she thought with a grimace.

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