In for a Penny Ch. 01

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Tobias Highlander begins an unexpected journey.
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Myikael
Myikael
6 Followers

Tobias had been waiting at the bar for nearly two hours. Stood up again, he thought. He'd stopped looking for Beth, the brunette he was supposed to meet tonight, and paid more attention to his glass. When the bartender gave him that, "ready for another?" look Tobias just nodded and a fresh glass of draught appeared on the bar. He slid a bill across the bar then waved away the change. He couldn't really afford to be drinking much less tipping that much, he didn't want to be asked to leave. Last one, he thought, then I'm out of here.

The tap on his shoulder broke his reverie. He turned his head and looked straight into a pair of breasts. Not huge, not even big, but just right. His eyes moved up and he had to tip his head back to see her face. Nothing remarkable except, maybe, the dark pools of her eyes. And the smile, not quite perky, but bright and framed by full lips. Beauty didn't cross Tobias' mind, but the adjective, perfection, did. Except she was so tall.

"Are you Highlander? Tobias Highlander?" she asked with little inflection.

"Try it without the 'a', but yes, that's me." He didn't want to sound impressed, and he sure didn't want this woman to think he was snooty because he corrected how she pronounced his name, but his name was about all he had these days.

"Oh," she said, "Tobis Highlander?"

A straight face that made Tobias think an unflattering thought connected to her thick blond hair.

Her eyes ran over his face and made a special note of his eyes. In the poor light she had to guess they were a light blue and wondered if they darkened when he thought about sex.

"Tobias Highl'nder," he said hoping he didn't sound too stuffy. "No 'a' after the l. And you are...?"

The tall blond seemed to think about the way Tobias pronounced his name them barged ahead. "Beth asked me to find you and tell you she couldn't make it tonight," she said. "I'm Jennifer Talbot, and the 'a' is pronounced." She held out her right hand and not so much grinned than laughed with her face. Even her eyes were part of it. After Tobias shook her hand she fought the urge to brush the stray strands of milk chocolate colored hair back onto his head. Why did Beth blow this guy off, she wondered. He's cute.

"Well, if Beth isn't going to make it I guess it's time for me to shove off. Thanks for telling me. Jenny, right?" He was still looking up then discovered Jenny had effectively blocked his way off the stool. He avoided the temptation to look back at her breasts, but just barely.

"Oh, don't go," Jenny said in her best little girl voice. "Let me buy you a drink, at least so your night isn't a complete wash." She stayed close while she looked for the bartender who caught the look and approached her and Tobias.

"This will be last call," he told Jenny.

"Two Thomas Irish Whiskies, please," she said and only then did she step back a pace.

Tobias turned to say he'd stick with his beer but kept silent when he noticed the bartender was looking up, too. Tobias knew the guy was at least six feet tall, so looked back at Jenny and just barely managed to stop the obvious question.

Jenny was ready for it, but when the question didn't pop from between that man's luscious lips she was grateful for the silence and decided she was going to do her best to make him happy that her friend, Beth, had stood him up. He wasn't just cute he was a gentleman, just what she'd been looking for.

"Get a room or do it right here on the bar, I don't care, but pay for the drinks, first," the bartender said with a chuckle. When Jenny and Tobias kept staring at each other he rapped his knuckles on the bar.

A startled Jenny dug through her purse. When Tobias reached for his wallet she told him this round was hers, but if he wanted he could buy breakfast for both of them. He readily agreed and hoped he had enough cash. They downed their shots and Tobias couldn't believe how smooth it was. After putting their glasses back on the bar Jenny took Tobias' arm and gently guided him off the bar stool. At five feet, eight inches tall he wasn't dwarfed by her height but that didn't stop him from feeling a little intimidated by it. Jenny sensed that and smiled to herself.

Outside the bar Tobias stopped and pulled his arm free of Jenny's hand. He explained, painfully, that he wasn't just short of cash, but that he didn't have a car, or much of anything else. He told her he was currently crashing at a buddy's apartment until he could get back on his feet. If she didn't shy away from the being broke part she might take the rest of it without running for the hills.

"That's ok," she said and took his arm again. "We'll take my car, get some breakfast, then I'll drop you back at wherever your staying. Is that all right?" Her voice reflected her smile and the warmth calmed Tobias' worries, at least for now, but when he hesitated she went on. "I think you're cute and a gentleman, and, unlike Beth, those are some of the important things I like in my man. And you seem to be just a real nice guy." Some other night or some other man and she would have added, "And this is the least I can do to make up for Beth's bitchiness." She didn't want him thinking she was a mercy fuck or anything like that. She chose her bed partners with care and mercy was rarely on the menu.

Was she hitting on him? Teasing him? Tobias figured out she was probably just being nice. She was the kind of woman who was nice to everybody, but wanted to look up to the men she dated as much literally as figuratively. He was still curious about her height but made a guess at six-two and left it unsaid.

"Come on, Toby, I'm hungry. A girl as tall as me needs to eat regular meals, and I really want to spend some time with you, get to know you." She watched his remaining resistance melt away and, just to keep his mind where she wanted it told him, "And I'm six feet, three inches tall. Now you know my dark secret. Satisfied?"

When she laughed Tobias laughed with her. He accepted her offer of breakfast thinking he could use a good meal. Being broke sucked, and sponging off his friend was even worse. Might as well take her up on her offer before she, too disappeared from his life.

He expected a pickup truck or maybe an SUV, something big for such a big woman, so was surprised when she opened the passenger door of a relatively small hybrid. He got in and then watched Jenny get behind the wheel. The car fit her like a glove. Plenty of head and leg room and she slid in with no difficulty at all.

Breakfast was at a 24 hour chain restaurant known more for large portions and low prices than for high quality, but Jenny and Tobias were both hungry and took advantage of the bottomless coffee cups, too. They talked and laughed, but Tobias steered any questions about his past back to the present. He was pretty sure if he told her all his history she'd be gone in a flash. Without being aware of the change from dark to light, they finally finished breakfast.

"Look, Toby, I'm tired, and you already told me you don't really have your own place, so why don't you come home with me and crash a few hours on the couch? We'll both get some sleep, and then, if you want, I'll run you back to your friend's place."

"I don't know, Jenny. You've been nicer to me than any one has been for a long time, and I don't want you to think I'm just a bum looking for a place to sleep and a free meal." He struggled, now, wanting to accept but needing to be a man and take care of himself.

"Toby, I like you a lot," Jenny said and covered his hands with her own. "And I like being with you. It's easy to like people, but spending time with them can be rough, and I like spending time with you. So, we'd both gain." She locked her gaze on his eyes and whispered with a giggle, "But not sex."

The remark was so out of place Tobias laughed. "Aright, but just so you don't fall asleep at the wheel." He hesitated for just a second before adding conspiratorially, "And you remember the part about sex." He was comfortable with Jenny and, truth be told, did not want the evening to end. Not even in the daylight.

Tobias woke up to the smell of fresh coffee. He kept his eyes closed and let his nose tell him if there was any bacon or eggs. Receiving a negative response he opened his eyes and looked around trying to reorient himself. Strange apartment, strange couch, gave way to his memory of Jenny Talbot. Tall, gorgeous, and one of the nicest people he'd ever met, but he didn't hear her moving around so he sat up and looked again. All he saw or heard was emptiness. And the gurgle of a coffee maker spitting out the last drops of water.

The kitchen was small with a breakfast bar separating it from the combination living room and dining room. Without calling out Tobias got up from the sofa and made his way to the kitchen. There were two empty mugs beside the coffee maker so his filled one and then leaned back against the counter to enjoy the first sips. She made good coffee, but he thought it could stand to be stronger. His time in the Army had taught him coffee needed to be strong, especially for that first cup in the morning.

Morning? What time was it? He looked around for a clock, but it was his second scan that revealed the digital clock on her microwave. Just a few minutes past noon.

"Hello? Jenny?" No response so he walked back into the living room. "Jenny?" he called louder. It finally dawned on him that she'd probably left her apartment right after starting the coffee maker. Taking out trash? He could think of no logical reason for her to leave him alone in her apartment so he sat at the small round dining table. No way was he going to go snooping around. He could wait.

An hour late he realized he'd been dumped again. Jenny had gone out for the day so she wouldn't have to face him and tell him to take a hike. That didn't explain the fresh coffee, which was almost gone, now, but she'd probably made her decision while he snored and she prepared the pot. Well, it could have been worse. He finished the cup he was working on and decided to dump out the old and make a fresh pot for his hostess. Then he'd slip away and thumb back to Paul's apartment and she'd never have to put up with him again. Good plan.

He didn't like snooping, but had to open nearly every cupboard door to find coffee grounds and filters. Once everything was ready he wrote a note thanking Jenny for her hospitality and propped it against the coffee maker. The opening door startled him.

Jenny had two grocery bags in her hands and her eyes widened when she didn't see Tobias still asleep on the sofa. Then she looked into the kitchen, saw him there, and her face smiled. "Good morning, sleepy head. Or should I say, 'afternoon?'" When he didn't reply she asked, "How long have you been up?"

Coming out of his embarrassment at being caught he replied, "About half a pot. I was making you a fresh one before I got out of your hair." He turned the maker on and tried to slip between Jenny and the end of the counter. "Thanks for everything, Jenny."

"You're not getting out of here that easy," she pronounced and then sniffed the air. "Why didn't you take a shower? You smell like you spent the night in a smokey bar."

He felt like he'd just been called to the principal's office, and tried to explain. "I didn't want to go snooping around your apartment, or using your towels without asking first, and, don't have any of my personal gear here." He was almost afraid to look at Jenny. She was right, he should have, at least, taken a shower, but he'd been too intent on not violating her privacy. "Besides," he joked, "never know what unmentionables a guy might find hanging in beautiful woman's bathroom." They both laughed.

"That's why I was out. I ran down to the store and bought you a razor, some blades and shaving cream. Oh, and a tooth brush." She handed him one of the plastic bags. "Now, please, do me a favor and go clean up. I know you don't smoke, but you smell like an ash tray. Not quite peremptory, but a command never the less.

"Yes, Ma'am," Tobias joked and saluted her. He walked through the door Jenny told him hid the bathroom. He hadn't looked for it to urinate when he woke up, and now, after more than half a pot of coffee he was glad for the chance.

Soon he was standing under a stinging hot spray scrubbing himself. He wished for a plain bar of soap but found only a bottle of scented liquid body wash. The shampoo wasn't bad but it, too, had a vaguely feminine smell. When he stepped out of the shower he grabbed a towel, wiped himself dry, and then tied the terry cloth around his waist. He hadn't had a new blade in his razor at Paul's for more than a month so shaving with a sharp blade was a real treat. He didn't know why he bothered to shave as often as he did because his beard never had been heavy or thick, and he didn't think it ever would be. No beards or 'staches for guys like me, he told himself.

Finally finished, he looked in the mirror, ran his fingers through his hair to straighten it out a little, and then looked for his clothes. He was sure he'd just dropped everything on the bathroom floor, but the whole pile was gone, including his shoes. He hadn't heard anyone come into the bathroom, but he'd been preoccupied with enjoying the hot shower. He wrapped tightened the towel around his waist then opened the bathroom door.

"Hello? Jenny? Do you have my clothes?" No reply.

"Jenny?" He opened the door wider and listened? Then he stepped into the short hallway and walked the three paces into the living room. No Jenny.

If Tobias hadn't been holding onto the towel it would have fallen to the floor when Jenny raced back into her apartment.

She stopped and stared at her guest. Much more muscular than she'd imagined, but thinner, too, without any clothes. That should work out just right, she thought. His hair was still damp and looked to be matted so she figured he hadn't borrowed her hair brush or a comb. Well, no matter, it will give me an excuse to work on it a little, she thought.

"All cleaned up, I see, and you don't smell like a pack of pre smoked cigarettes anymore. In fact, I like the way you smell now." Jenny walked towards him and he didn't realize he was backing up. "Stand still, silly, I don't bite," she said. "Too often, anyway." That worked and got a smile from him just as his back touched the wall.

"Did you take my clothes?"

"Yes, they smelled terrible from all that cigarette smoke from last night, so I ran them down to the laundry room. I hope you don't mind too much, but I just don't like that smell in my apartment." She closed the gap and fussed with his hair for a few seconds. "Wait here, and I'll get a comb to take care of this rat's nest before it dries." Jenny was back as quickly as she'd disappeared into the bathroom.

Tobias stood still and let her comb his hair and thought he needed to get it cut so it wasn't such a mess. He closed his eyes and enjoyed the attention for just a second. It stopped as quickly as it started. Tobias felt strangely let down. Then he wondered what he was supposed to do while waiting for his clothes.

"I had an idea while stuffing your jeans into the washing machine, Toby," Jenny said. "If you're serious about a job, I might be able to help." She let the thought hang in the air unwilling to force the issue with her new friend.

"What do you have in mind?"

"Hold on a minute, Toby." Jenny waited just long enough. "You look silly with just that towel on. How about I get you some jeans to wear, and maybe a t shirt?"

"Sure." He hesitated at first then figured why not. Jeans and T's were just jeans and T's, right?

"Good, because I don't like talking business with half naked men." She laughed and Tobias tried to. "I'll be right back."

In less than a minute Jenny returned with some clean clothes. There was even a pair of boxers. When he turned to go to the bathroom to change Jenny stopped him.

"Just put them on, Toby. I won't look if that bothers you." She grinned, turned her back to him, and then walked towards the kitchen. He was more pliable than she'd planned.

"Hey, wait a minute," he said. "These are women's panties. There's no hole for my...". Now, how do I say 'cock' to this angel?

"Cock?" Jenny tried not to laugh. "Look, Toby, it's going to be little while before your clothes are clean and dry, and I can tell sitting around in just that towel will make you uncomfortable. But all I have is women's clothing, so I brought out the most masculine things I own. It's not like I'm asking you to try on one of my dresses."

Tobias returned to the bathroom despite Jenny's earlier pronouncement, where he pulled the boxers on. To his surprise the shorts didn't just fit, they hugged his hips and he felt the leg hems under his ass. He found the smooth nylon cupping his genitals almost erotic. He glanced in the mirror and thought the panties were masculine enough because the leg openings were the same length all the way around his thighs. He pulled the jeans on next and they, too, were close to the right waist size but a couple inches too long. He turned up the legs so he could see his feet. Last came the t-shirt and it seemed too small until he pulled it over his head and down his chest. It stretched and clung to his muscles like a second skin. He ran his hands against the fabric trying to figure out what it was. It was similar to the material of the panties Jenny loaned him but a little heavier and a lot shinier. No one's going to see it, he thought, but he blushed when he stepped out of the bathroom.

Jenny was in the kitchen leaning on the counter between the rooms and stared at him. She was still beautiful, her hair still yellow gold, and she was still a lot taller than him. But there was something in her smile he hadn't noticed before. A single word flashed through his mind. Predator. The thought was gone just as quickly as it appeared.

"I like that shirt on you, Toby," she said. "It fits you better than it does me." Again her sunshine bright smile eased his discomfort. "Have a seat and let me offer you a job."

Tobias sat on one of the two stools at the breakfast bar and Jenny handed him a cup of coffee and stayed on the kitchen side so she didn't spook him any further.

She explained to him that she ran a modeling agency and she really was looking for someone to keep her offices, studio and other rooms in presentable condition. He would be expected to perform minor building maintenance as well as some clean up duties between visits from the people who did the regular cleaning. She wrote something on a pad of paper then turned the pad so he could read it.

The number wouldn't make him rich, but he figured he could live on it if she let him work more than a few hours a day. She assured him he would be needed at least 40 hours per week, but a lot of that time would be after normal business hours. Many of her clients and models worked late and her studio often didn't close until nearly midnight. While he tried to think of a way to accept without seeming too eager, Jenny looked at the clock on the microwave.

"That load of laundry should be done, Toby. "Why don't you run down there and put the wet clothes in a drier?" Before he could refuse she told him the laundry room was just down the hall from her apartment.

"Dressed like this?" He emphasized his question by holding his hands out with palms up and scanning his torso.

"I have to use my bathroom," she said, "and the sooner that stuff gets dry the sooner you can change back into your man clothes." This time she giggled. "Besides, who's going to see you, and even if anyone did, they wouldn't know the difference between what you have on now and what's in the washing machine." She walked out of the kitchen and kissed Tobias cheek. "Please? Be a dear?" she wheedled.

Without waiting for a reply she headed for the bathroom.

Myikael
Myikael
6 Followers
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6 Comments
AnonymousAnonymousover 9 years ago
very interested

Your story is captivating. You're describing one of my most erotic fantasies. Please don't keep me waiting, even though I know how it ends; at least if it's anything like I dream about. I want to read your entire story. Please!

MyikaelMyikaelover 9 years agoAuthor
Thank you

Anonymous 1: I agree, I need an editor. If you're interested in making some more editorial comments I've posted this story for critiques at http://forum.literotica.com/showthread.php?t=1100815 .

The error you pointed out should read "...as...", not "...than...", has been changed, and will be submitted in a few days along with other necessary edits/revisions pointed out through the link above.

Thanks to all of your for reading. Chapter 2 is about half written and I hope to submit it next week.

We all have to start somewhere, and this it my start here on literotica.com, so sorry there's nothing more. But I'll try to keep you folks satisfied with a good story.

AnonymousAnonymousover 9 years ago
What on earth...

...does this mean?

" She held out her right hand and not so much grinned than laughed with her face. "

You need an editor.

wolf9696wolf9696over 9 years ago
liked it

hope you write more......just hope she is a top....and he doesn't get too sissified n cross dressed

SexymaxSexymaxover 9 years ago
More Please

Can you please continue this as its just getting interesting

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