Big City Success

Story Info
Compromises a small town girl makes to succeed.
2.5k words
3.97
45.8k
4

Part 1 of the 2 part series

Updated 10/29/2022
Created 02/03/2007
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
leann511
leann511
180 Followers

Jan moved to the big city a few years ago right after graduating from high school. Quickly she realized she should have found a job before moving.

"I'm really sorry; Miss Engels, but I've hired young people fresh from the farm on several occasions and about the time they reached the point where they could start paying back the cost of training, each one suddenly got homesick and went home."

"But I would never do that; I'll sign a contract if necessary."

"Then if you quit, I could sue you. For what, dear, the clothes on your back?"

At a fast food restaurant, she found some part time work. She had no place to stay except the backseat of her old car. The problem with that was finding a safe place to park it.

Jan lived like that for nearly a year, searching for a job all day, working sometimes in the evenings. Finally she realized that she couldn't go on. With frugality born of sheer desperation, she'd tried to set aside enough money for the gas it would take to get home, but she had managed only a few dollars. She'd have to call her mother collect, and ask her to wire enough money to get back. She dreaded making that call. She dreaded going back to everyone laughing at her and her big talk about moving to the city. A mile of crow was waiting for her to eat and every mouth filled with, "I told you so."

At a bus depot, she cleaned herself up as much as possible. She'd never realized what a luxury a bathroom was. So many things she'd taken for granted before she decided to move to the big city. She had one more interview set up last week by an employment agency. The job counselor had been enthusiastic about the mail room training position but Jan had let her hopes soar too many times from the super positive attitude of agents. Their job was to get you hyped up to be sure you showed up. She would keep that interview just to put off calling her mother one more day.

The address turned out to be a forty story building. The insurance company occupied two floors. The personnel office was on the fourth floor and she entered to find three young girls ahead of her. She was surprised because, in her job hunting experience, mail clerk jobs were usually sought after by young men, as though the title actually read "male clerk". The receptionist gave her some forms to fill out and she busied herself with that. The young ladies were summoned to an office and came out relatively quickly. Much before she expected it, the receptionist called her name.

Inside the very lushly appointed office, a woman of statuesque size and beauty met her at the door and extended her hand with a broad smile, "Good Morning, Ms Engels, I'm Ms Matthews; you're here about the mail clerk position?"

"Yes, I'm very impressed with this company and would very much like to get a starting position in some capacity."

"Well, the mail room is an entry level position but a bright and ambitious girl could quickly work her way up from there."

"That sounds just fine to me, exactly what I've been looking for."

"I think your application is in good order. You've been in the city long enough to show you're determined to stay."

"Yes, I've made up my mind to remain here."

"But you're probably tired of working for peanuts and living in flop houses."

"Well, I've had a difficult time..."

"Maybe you'd like to show me how much you want this job."

"Why, certainly, but how do you mean?"

"For one thing, I like young girls that I hire to sit in my lap during the interview."

Jan was aghast. She'd been so excited to believe that she had a legitimate job opportunity and now she was being asked to do something she thought was completely strange. Realizing why the other interviews had been so brief, she knew she should get up and leave. This was her final opportunity, the only chance of avoiding calling her mother and returning home in defeat. She could no longer afford her self-respect. Jan walked calmly to the woman and sat down in her lap, snuggling her rounded butt deeply into the lush curves of the woman's thighs.

"Oh, that's such a good girl," Ms Matthews talked with her hands all over her, on her hips, her thighs, her ass. "I think you have exactly what it takes to become an important asset to this company. Do you mind undoing a few buttons so I can see if you have nice tits?"

The next day, Jan was embarrassed about what she had done, showing her tits to that lecherous old woman, even letting her rub the front of her panties. Those feelings were eclipsed by her joy in finally finding a job. Ms Matthews had been so casual and relaxed, as though it was perfectly normal to hold her in her lap while they discussed her qualifications and the demands of the job. In the back of her mind, she had an uneasy feeling, as though the interview was a conditioning process for the requirements of working there.

Nonetheless, she donned her other presentable outfit and showed up for work at the appointed time. She was taken to the fifth floor, an entire level divided into little individual cubicles with walls only chest high. Each and every cubicle was occupied by a female, all of them exceptionally young and attractive.

She was led to the mail room and introduced to Lucy, the head worker in that section. She was the only older woman Jan came in contact with. Lucy introduced her to Stella, the other mail room employee and the one that did all the work. Jan went along with Stella for several days. They retrieved a sack of mail, twice daily, at the post office, sorted it and loaded it on carts according to a diagram. Jan discovered that the method facilitated delivery. As the rounds were made; each person's mail was next up on the cart. Stella kept up a barrage of comments about exactly what each person did and how they wanted their mail handled.

Jan made a few mistakes at the beginning and Stella lost patience with her once, the second time she committed the same error. "I'm going to get Ms Matthews," she declared in exasperation after bawling Jan out for five minutes.

Lucy came over to her as she struggled to contain her tears. "There, there, baby, don't be so upset. You're just learning. Everybody makes mistakes. Stella shouldn't bring Ms Matthews into it," the matronly woman said as she hugged Jan close to her ample bosom. Then, as if the thought suddenly occurred to her, the woman inserted her hand into her blouse and lifted out one huge titty. "Do you want to suck? It always makes the other girls feel better when they're in this kind of trouble."

Mortified, but the woman had her thinking it was common practice, Jan was so distraught that she took the woman's large nipple into her mouth and felt a warm contentment as she sucked on it.

"Don't worry, precious, it'll all be over in a little while. Ms Matthews is very strict but she's fair. She knows you can't learn it all immediately." Lucy placed her hand protectively over Jan's cheek and hugged her tightly against her. "You're such a sweet little girl, Mama loves for you to suck on her titty. You can do it any time you feel the need."

In Ms Matthews' office, Jan was worried that her career would be ended before it even began. Stella was there, too, brimming over with malicious anger.

"Oh, my dear, what have you done now?"

"She delivered Ms James mail to Ms Jones. This is the second time she's done it. I don't think she can even read," Stella replied before Jan could speak. "Ms Jones brought it to me and aired me out about stupid mistakes."

"Ms Jones is involved in a separation from her live-in, Ms Higginbottom. She's not in a very good frame of mind."

"Well, I don't think I should bear the brunt of her anger."

"Of course not, you go right on back to work and I will deal with Ms Engels. I'm sure she will be more careful after this."

Something in Ms Matthews' voice filled her with alarm but she felt a sudden surge of hope because, apparently, the woman did not plan to terminate her.

"Do...do you want me to sit in your lap?" Jan asked in an effort to appease the powerful woman after Stella stormed out of her office.

"Yes, dear, you may if you like."

Jan thankfully took her position, careful to wiggle her behind deeply into the woman's thighs, even tucking her tummy in abruptly to jerk her bottom downward into the woman's lush lap. She even pushed sideways several times to increase the contact with Ms Matthews' abdomen.

"With so many people involved in this altercation, I will be forced by company rules to discipline you," Ms Matthews explained as she placed her hand on Jan's hip and pulled her tighter against her abdomen, humping herself heartily against the girl.

"What will you have to do?"

"Well, the normal penalty is five strokes with the cane but since this is so early in your training, I can mitigate it to two, and give you a light spanking with my hand if you are cooperative."

Trying to appear very cooperative and helpful, Jan asked, "Do I need to take my panties off?"

"I'm afraid so, hon, rules from very high up, all discipline must be administered to a bare behind."

Allowing no reluctance to show, Jan lifted her skirt and slipped her panties down to her knees, then bent over to grab her ankles.

With a surge of arousal that would take three women to extinguish, Ms Matthews drew back the cane she'd taken from her desk and tapped it lightly against Jan's beautiful backside. Quickly the cane whistled back and slashed remorselessly into Jan's buttocks, wrenching a startled cry of anguish from the girl.

Jan gritted her teeth, steeling herself against the next one. It came just as quickly and just as mercilessly. She emitted a huge sob and tears flooded her cheeks. Then Ms Matthews pulled her firmly across her lap as she sat down. A brisk hand spanking ensued but it was nothing compared to the cane.

She dedicated herself to her job and learned to be extremely careful reading names. She showed such aptitude and learned so well that Stella was able to leave the department for a better position within two weeks. The girl was almost grateful to Jan and let her know that she was pleasantly surprised by how rapidly she's caught on. Standing beside her, she put her hand on Jan's butt and fondled it extensively in a gesture of acceptance. Jan had grown quite accustomed to such demonstrative acts from women that worked here and had stopped making a fuss about it long ago. She merely arched her back and jutted her ass out more.

Shortly after receiving her second paycheck and by selling her old car, she was able to move into an apartment but long hours of commuting were necessary because what she could afford was so far away from her work.

She was so relieved to finally get an apartment that she was content to spend all her free time there, fixing it up just the way she wanted it. When that was accomplished, she became restless and wanted to go out but was unsure of a safe place to go alone. She was completely intimidated by stories of muggings and rapes. So every evening, when she finished work, she trudged to and from the subway station. She realized she was relieved to be rid of the car, the upkeep and the eternal search for a place to park made it much more trouble than it was worth in the city. Her life settled into a rather dull routine and the thrill of succeeding in the city began to dissipate, having her own place to live even eventually lost most of its luster because of the loneliness. .

True to her promise, Ms Matthews hired a new trainee for the mail room and quickly promoted Jan to one of the cubicles where she was trained to receive, prepare, and transmit claims to the claims adjuster. She knew from there, she might become an adjuster. Linda, the young lady who worked in the next cubicle, was very helpful and friendly to her.

"Maybe you'd like to go out together some night?" she asked.

Jan could barely contain her eagerness as she accepted and they decided on the next Friday night. So excited she could hardly wait, she went on a shopping trip and splurged with her newly-acquired credit card on a dressy little black dress. The short skirt emphasized her legs and made her look and feel extremely desirable. She had her hair and nails done and was waiting anxiously Friday night for Linda to show up. She was sure she would have fun and find out a lot about where women went and what they did to have a good time in the big city.

Unlike her expectations, Linda took her to a supper club that featured a play she knew had been on Broadway but the leads were tired old TV has-beens. Jan was worried if she had enough money with her but Linda graciously paid for everything. Jan was very grateful to be out of her apartment and able to enjoy herself. She was a little concerned about Linda's attitude; the girl was very touchy-feely and spent the evening with her hand in Jan's lap, rubbing her thighs and even brushed her titties several times. She would wrap her arm around Jan's waist when they were walking and her hand would stray down to Jan's ass when Linda guided her with the pressure of her hand. Jan didn't know what to make of the girl's strange ways. She knew she was competent to find her way through a doorway on her own.

Jan was totally confused when they finally arrived back at her apartment and she told Linda what a nice time she had. Linda said very confidently, "Oh, honey, we're not finished yet. We're barely getting started." Then she put her arm around Jan's neck and calmly ushered her into her own apartment. "Get undressed while I fix us a drink."

Jan was thinking that Linda was merely inviting herself in for a sleepover or something so, to comply, she started undoing the buttons of her sexy black dress. "I'm sorry but I don't have any liquor here."

"Now why am I not surprised? I'd think a worldly sophisticate like you would have booze on every level surface. Just on a hunch, I happen to have a pint of Tennessee mash in my purse. Do you have any cokes?"

leann511
leann511
180 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousalmost 6 years ago
Not arousing at all

This was soo shitty, read half of it and creeped out.....

AnonymousAnonymousabout 17 years ago
Fascinating premise

Although the sudden end is a little odd. I wouldn't say no to more installments!

AnonymousAnonymousabout 17 years ago
Nice start!

I certainly hope that this is chapter one ... of many!

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Cheat Days Ch. 01 A confused wife discovers her repressed desires.in Lesbian Sex
Sunday School A soccer mom is obsessed with a young Sunday School teacherin Lesbian Sex
Halloween Party at Willamette Pretty college girl parties with decadent wealthy lesbians!in Lesbian Sex
Beyond Our Control Ch. 01 A failed date is the start of something new.in Lesbian Sex
Summer Humping Dry Humping with My Friend.in Lesbian Sex
More Stories