From Darker Places than I Want to Feel Ch. 01

So I find myself wandering through my catalog of stories looking for writing issues that happen when you are just starting out. I found a few, missed some too...probably.

Here's a story I first posted on Literotica in 2013, it explores the budding relationship between a college professor and a young woman who has lived a life full of challenges because 'she took the road less traveled.'

I thought, perhaps, readers might enjoy revisiting this story so I decided to repost it here. As always, characters in this account involved in sexual activity are above the age of eighteen and those of you under the age of consent are discouraged from reading this story due to adult language, situations, and content.

Thanks for reading and check out my bio page for more details.

For now, enjoy "From Darker Places than I Want To Feel - chapter 1."

*****

The Last Meeting.

"What?" she asked, glancing over as he added cream to his coffee.

"Nothing," he responded sullenly.

"Don't 'nothing' me, I can see something's wrong, it's written all over your face."

He sighed, stirring the cream in his coffee and looking out the window of the corner café. They chose this place as an escape from the drizzle and drip of rain outside. Besides, it was too cold and damp this morning for anyone to sit on swings in a park. A better day to stay wrapped up in a warm blanket and read.

But it was reading that got him into this funk in the first place, so today reading wasn't an option, at least not now.

"Come on, spill it," she insisted softly, reaching out with her hand to gently touch his.

He sighed again and turned back to her.

"I as reading a story online last night. It was several chapters long and at first it was really a sweet love story about a woman who was slowly bringing out her young husband's feminine side."

"Isn't that the kind of stuff you like? Love stories between two people who care about each other?"

"Yes, but that's not all. It's the fourth part that really got to me. It turned really dark and sinister. It was like a different person penned the last chapter of the story."

His eyes had a sadness to them that spoke volumes about him.

"The woman in the story turned into this terrible vile bitch. She was turning her lover/husband, who was totally devoted to her, into a sissy slave to be abused by someone else. There was no love, no remorse, nothing, just a coldness that was really disturbing. Her true self came out in the end when she claimed to be totally disgusted with the poor wretch. She just kept twisting and taunting him. She told him that she planned the whole charade with her old boyfriend from the start. She had been shagging the SOB on the side the whole time. Even while she was telling her husband how much she loved him, on their honeymoon no less!"

He paused a moment and sipped on his coffee as he looked away from Sarah's eyes and out the window once again.

"How can someone be so hateful? So treacherous, that they would conspire with such venomous deceit to destroy a young man's love and life? He was forever ruined as a result."

"Why didn't you just stop reading it?" she asked. Her smile was gentle and caring but her eyes belied a sense of worry and concern.

"I did. But not before the author managed to repulse me completely with verbal images that will stay with me far longer than I want."

He paused a moment to reflect on it again.

"I suppose if that was their intention then it worked. They managed to enrage me to the point that I wanted to reach through the computer monitor and strangle them. And by the comments that I read, many other readers reacted the same way."

"Did you post your own comment?"

"No, it wasn't worth it. The others said what I would have said and in some cases more eloquently."

Ryan pause again and smiled wistfully as he looked into Sarah's eyes.

"Thank you."

"For what?" she asked.

"For putting up with my rants. For answering my many questions, even the most personal and private ones that I asked. You really are a beautiful person."

"Well, finally, you've noticed!" she exclaimed with a huge grin. "It's about time."

"Oh, come on," he replied, "what I meant is that you really are a beautiful person on the inside too. Everyone can see how gorgeous you are on the outside. But it's what's inside your heart that really matters. Besides, I told you the first time we met how much I appreciated you opening up to me on such a personal level."

"Yeah, that was probably the most awkward meeting I've ever attended," she replied with a gentle smile.

"Yes it was, for both of us," he agreed.

"You were so naïve," she purred.

"I guess, in a way, I still am," he pondered out loud. "I still can't understand a person getting so much sexual gratification out of destroying another soul like that."

"You're still dwelling on that aren't you?" She replied with a tinge of worry.

He offered her a half-shrug and rested his chin on the palm of his hand.

"That's part of the complexity of the journey I suppose," she mused. "Once you take the path less traveled you have to escalate that sort of behavior until something, or someone, crashes and burns. You just have to let it go, Ryan. Thankfully there are very few people in the world like the one you described."

"Is that the price you pay for the depravity? The crashing and burning part?"

"I hope so."

Ryan glanced away again at a family who sat down in a booth nearby. The mother was fussing over two small children while the father cleaned up a spill under the table. It was all rather humorous and natural in the same moment. Ryan thought about that scene and then he thought about Sarah. Would she like to have had kids? He wondered.

He sighed. "What time is it?"

"Nearly noon, do you have to go somewhere?" She didn't want their meeting to end so soon.

"No, well yes, sort of, plus I just didn't want to take up your whole day, this being our last meeting and all. Where are your nephews?"

"With their mom, she had the day off." She was distracted by the thought of their last meeting and what it meant.

Sarah looked out the window and away from Ryan. She blinked back the moisture that was brimming in her eyes. She took a big breath and let it out slowly. She steadied herself, and then she turned to look at Ryan.

"I don't want this to be the last meeting," she whispered.

"What do you mean? You were the one who negotiated for us to meet only three times. I agreed, reluctantly, but managed to get you to accept the possibility of three more if our conversations got interesting, which they did. But you were very adamant about it not going beyond six."

"I know," she said softly. "So now I've changed my mind. It's a woman's prerogative you know."

That brought a wide wry smile to Ryan's face. His eyes twinkled in the brief splash of sunlight that streamed through the café window. Sarah smiled back then blushed a deep shade of crimson.

"Does this mean I get to ask you more questions?" he asked.

"Yes, but I get to ask you some too," she countered.

"Tit for Tat?"

"Exactly," she replied keenly.

"Okay, since I've been asking most of the questions lately," he replied, "today it's ladies' first."

Sarah thought for a moment then smiled coyly. "Would you go on a date with me?"

Ryan blinked a moment and looked at her carefully. "Is that your question?"

"Yes. There was a question mark on the end of the sentence wasn't there?"

"Hmm. You know I'm old enough to be your father, don't you?" He added a serious tone but Sarah could see the twinkle in his eye. It was obvious to anyone watching that he was as excited about the prospect of a date with her as she was.

"I think you're trying to dodge the question, Mr. Sullivan," she countered watching him intensely. Her eyes shone brightly.

Ryan studied her a moment longer and wondered how serious she was about all of this. Did she really want to go out on a date with him? She's nearly half my age. He remembered that she just listened to him rant on and on about trust and love and deceitful people. She must know how much it means to me. I suppose, what better time to ask than now?

Ryan knew he'd be a fool not to jump at the chance to go out with Sarah. She was gorgeous, drop-dead, runway model gorgeous; long brunette hair, falling in gentle curves that shaped a lovely face with sculpted eyebrows framing her hazel green eyes. Her slender build enhanced by her feminine curves and the pleated skirt belted at her narrow waist drew the attention of every man in the café.

He also knew he didn't have a snowball's chance in hell with her even if he did agree to date her. But that didn't matter. He really enjoyed her company no matter what the circumstances. He shrugged and smiled. Then he leaned across the booth towards Sarah. She sat there resting her chin on her folded arms. She was watching him closely.

"Yes, it's a date," he said, "for dinner and a movie. Tomorrow night. Six o'clock sharp. I'll pick you up at the swings in the park where we first met. What's you're next question?"

"I get more than one?"

"Of course, but only one more for now, I'm supposed to meet my friend Paul for a round of golf this afternoon. But from the looks of things I bet we call it off." He glanced once again out the window.

She smiled blissfully and popped her head up impishly.

"Do you have a girlfriend?"

He grinned and shook his head.

"My wife died a year ago, remember? Between work and my writing I haven't found the time for anything else, let alone a woman in my life."

"Good," she whispered softly then she got out of the booth. She leaned over and kissed him on the cheek with a light peck. "See you tomorrow night at six, bye."

She turned with a twirl of her skirt and was down the aisle and out the café door before Ryan could blink twice.

She was always good at finishing conversations before he wanted them to be over.

He sighed with a wry smile. He knew he really shouldn't keep seeing her, but he just couldn't resist her charm. It was the same impish charm that captured his heart over a month ago when he met her for the first time. It was in the neighborhood park outside of her apartment house.

At first he imagined what it would be like for her to be his daughter. He never had a daughter and the thought of one now after his wife died seemed to fill a huge hole in his life. Well, at least it made him feel needed again.

But as they continued to talk at their weekly rendezvous, it became apparent to Ryan that he was the shy, novice, and inexperienced one in the couple rather than her.

Her beauty was only a mask to hide emotions and experiences that lurked in darker places than he wanted to feel at first. But as they talked he began to understand who she was on a deeper level. To a certain extent, he was beginning to learn more about who he was as well.

He began to really care for Sarah. By their third meeting the word 'love' lurked in the shadowed recesses of his mind but he was afraid to give it much thought. Not because he felt that there was some sort of social pressure to reject someone like Sarah because of who or what she was. Or the fact that their age difference might appear ridiculous to some, like he was acting out some sort of twisted Lolita play. But because when his wife died he bottled up all the love he had in the world and the thought of opening his heart to another and the fear that it might be shattered again shook him to his core.

He sighed again as he watched the glass doors of the café open again. New customers, shivering from the damp and cold, were coming in to dry out.

Nearly three months ago he placed an advert in the local 'Craigslist' looking for someone who understood the cross-dressing/trans-gendered life style and was willing to answer some questions.

He explained that he was a local writer who was doing some research for a novel. Several people responded but when they turned out to be more interested in soliciting than answering questions, he became discouraged and turned them down. He was beginning to have doubts that anyone would be willing to help him when Sarah emailed him, answering his query.

He replied with his cellphone number and asked her to give him a call if she was still interested. She did the next day.

"Hello, is this Ryan Sullivan?" the feminine voice on the phone asked meekly.

"Yup, who's this?"

"This is Sarah Daniels. I sent you an email the other day responding to your ad on 'Craigslist'."

"Oh yeah, great! Thanks for calling me back," he replied quickly. "Um, I suppose, before we go any further, we should discuss what this is all about."

"That would help, Mr. Sullivan, I'm rather nervous about all of this as you can tell," she replied timidly.

"No problem, okay, here we go. I'm working on a novel about cross-dressers and the world of transgendered women living and working in mainstream America. You know, trying to work, shop, and live just like anybody else. But my biggest issue is my lack of a deeper understanding about the lifestyle. Sure, I read and hear things about it but many of those stories are just that, they're stories that are filled with fantasy and hyperbole meant to excite the imagination. There's nothing wrong with that, it's just not what I'm trying to do. I want to make my characters honest with themselves as well as with the reader. I thought that the best way I could do that was to ask someone who has experience in that world and so now we come to you."

"What would I have to do?" she asked, her voice was still riddled with uncertainty.

"Not much, really," he replied. "Just answer some questions, truthfully and honestly. And with as much candor as you are willing to offer. No one will know about you, I will never reveal the source of my information. Ever."

"Strictest confidence?" she asked.

"Absolutely, strictest confidence, always," he replied with sincerity.

"Okay. Can I think about it?"

"Of course. Let me know in a couple of days if you can?" he asked.

"I will," she replied sweetly. "Mr. Sullivan..."

"Please, call me Ryan," he interrupted her.

"Okay. Ryan, how old are you?"

"I'm fifty-six. I teach at a local college, recently widowed, and I live alone, well, except for a dog and two cats. My son has recently married and lives with his wife in Springfield where he works for an industrial designer. I own my home and drive a practical car. My hobbies are writing and occasionally I like to go to wine tastings. That about sums up my boring life."

"Thanks Ryan, I'll be in touch soon." And the connection went silent.

Two days later she called Ryan back and told him that she'd do it.

"But I have a few conditions," she added.

"I expected that you would, go ahead," he replied.

"We have to meet in a public place and it has to happen during the day."

"No problem," he replied.

"We will meet for two hours each time and we'll meet for just this month," she added.

"Okay."

"And we'll only meet three times," she said with a sense of determination.

"Hmm, I'm worried about that. With so little time it might limit me and if I have a question later that I hadn't considered earlier, I wouldn't be able to ask them with only three meetings."

Sarah paused a moment, the phone was silent. Ryan could sense that she wasn't willing to waiver easily on this point.

"How about this. We meet for three meetings for two hours each. The meetings happen only on Saturdays and we'll meet outside in a public place like a park or something. However," he paused a moment to add emphasis to his need for flexibility. "I reserve the right to negotiate additional meetings if I find our conversations interesting."

"How many meetings?" she asked tentatively.

"Up to three additional meetings. Does that sound agreeable?" he asked hopefully.

There was another pause.

"Okay, agreed," she replied firmly.

"Great. I live near the college. Where do you suggest we meet?"

"So do I. I have an apartment near Grosvenor Square."

"I'm not that far away from there as well. I could walk there easily," he said with growing enthusiasm.

"Perfect, I watch my nephews most Saturdays for my sister so that she can go to work. We can meet in the park near the center of the square if the weather holds. This should work out great. I'll see you next Saturday, okay?"

"Absolutely, see you then. One o'clock?" he asked.

"See you then," she said and the connection was closed.

Ryan groaned. She closed the connection so quickly he was unable to ask how to recognize her. He reopened his cellphone and quickly texted Sarah back.

'How will I recognize you?' He typed and hit the send key. Then he waited for her response.

'I'll be wearing a pink top,' she replied almost immediately.

Ryan smiled, jotted down the appointment time, and then he closed his cellphone. He set the cellphone aside and turned back to his computer.

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 to 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.