Bedroom Windows Ch. 04

Story Info
Jennifer's fraternity flirting backfires.
6.2k words
4.62
152.4k
33

Part 4 of the 4 part series

Updated 10/27/2022
Created 04/26/2002
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Lou Davis sat silently behind his desk. Through his door he watched young Jennifer Bracken walk into the office, gingerly set her purse down on her desk and give a smiling hello to one of her co-workers. Lou’s eyes moved from her face down to her body. It was only last Friday when he had peeled the panties off of the very drunken beauty. He could still taste the sweetness of her pussy and its tightness as his large black cock had slipped inside.

He was actually surprised that she came to work. He figured by this time she would have quit out of embarrassment or had the cops arrest him. What he really hoped for was that she didn't remember a thing. He knew he had stupidly gone too far and put everything at risk for a little white pussy. He could only hope.

That hope, along with his raging hard-on seemed dashed a moment later when Jennifer stepped into his office, shut the door, looked him in the eye and said sternly "I need to talk to you, now."

Jennifer knew she had him. The look on his face told her he was already preparing mental excuses for what happened. She knew he wouldn't need them though.

She walked up to his desk. "I need you to promise me that you'll never let me drink that much again. I was up most of the night getting sick and only this morning do I feel even remotely like myself again." She smiled at him genuinely. "and if you ever buy me another shot I'll kick your ass."

Lou seemed to be in shock. He was barely able to respond when she thanked him for getting her home safe and made him promise to stop her from drinking next time. Lou sighed silent relief as she headed out of his office. As she walked back to her desk his eyes instinctively focused on her ass and wondered if any of his huge load was still inside her sweet little body. His hard-on returned as well as a big smile.

Jennifer sat at her desk trembling from excitement. She knew Lou thought he was busted and now he was realizing he had fucked her without her ever knowing. Perhaps even now he was planning on how to get her again. She loved that thought.

Her thoughts were soon interrupted by a disturbing phone call. Her mother. Dad was back in the hospital again and she would have to go out to Minnesota and help out. She called Mark at work and gave him the news. He said he would make flight arrangements for her. Lou was more than kind in giving her extended leave time on condition that he would get to take her out to lunch upon her return.

Mark. He had come home un-expectantly on Saturday even before she went to pick up Pop. So much for Pop's lucky night, for now anyway. She was surprised how disappointed she was on his early return and even more disappointed when Mark fucked her that night. It was so plain, so regular, so taken for granted. It was only when she recalled the image in the glass of Lou pumping away at her did she orgasm.

Minneapolis, a town where she grew up and knew well. She hadn't lived there since at 18 she and Mark moved away together. It always felt weird to be back.

She arrived late and when her mom picked her up at the airport they drove straight to the care center. They drove through some of the seedier parts of town and Jennifer stared out the window at the blinking lights of Minneapolis nightlife, mostly bars and strip joints. One extra glitzy strip joint's marquee had 'Amateur Week' blinking boldly. She wondered what it would be like to show complete strangers her body. A sexual shiver rushed through her body. She knew she would have to find out.

After spending several hours at the hospital, Jennifer and her mother drove home. Jennifer would have fallen straight to sleep if not for the wetness between her legs. Her fingers worked her clit as she imagined strange men slipping dollar bills into her g-string as they gawked at her creamy white tits with dirty dirty thoughts on their minds. Her body shook as she came and she bit her lip to avoid moaning out loud.

The next morning they headed back to see her dad. He had collapsed a few days ago and bruised his hips but would be able to go home in a week or two. In last nights drive Jennifer hadn't noticed that the care center was on the outskirts of the University of Minnesota campus.

Her Mom spoke up, "I'll show you where the bus let's off so you can stop by tonight. It will be a great relief to get back to work while you sit with dad." Her work consisted of bringing meals to the elderly and visiting the lonely until early evening and was glad to help.

After their visit they stopped by the mall for lunch. Since her mom just wanted to look at the latest purses they split up for a few. Shortly thereafter Jennifer found herself inside Frederick’s Lingerie. Thinking of the strip club she picked out a few outfits for fun, even trying one on, a black g-string with a semi see through top and a long black silk robe. She imagined the eyes watching. A few minutes later she walked out of the store with her new outfit along with a few pairs of sexy panties.

A few hours later Jennifer was standing naked in front of the mirror. She had just shaved her pussy bare except for a tiny triangle of soft blonde hair just above her slit. Again she wondered if men would really like her body. She felt her boobs and knew men liked them bigger but at a B-cup they were still nice and firm. She wasn't sure she had the courage to go up and dance in front of strangers, but would find out when and if the time came.

Derrick Wilson spotted her getting off the bus. He had just sat down on the grass after throwing the football with his frat mates. He watched the pre-occupied beauty walk slowly up the street looking around as though she was lost. A few seconds later he was walking next to her.

“You look a bit lost,” he said in an engaging tone.

Jennifer looked up at the handsome young man and smiled. Even though she knew where the care center was, she liked his attention and let him direct her to the front door.

“Dude, what are you doing?” blurted his friend to him a few minutes after Jennifer had disappeared inside the building.

“Gonna bag me a soccer mom my man.” He high-fived his buddy.

“But ain’t she married?”

“Married with two kiddies at home…five hundered miles from here. She’s all alone and in need to be Derricked”.

“oh yeah?”

“Twenty bucks says I have her panties pinned up on the board within a week.” He gloated.

“I’d like to see you win that bet.”

It was dark when Jennifer emerged from the care center. She gave Mark a quick call on her cell phone and gave him an update and that she was heading straight home to bed. She hung up and stared down the street to where the bus stop was. After a moment and a sigh she headed towards the stop. She clutched her large handbag that still contained her new outfit. As she approached the stop a taxi came into view. Without thinking her hand went up and the cab pulled over. A moment later she was headed to the other side of town. For a minute she thought about Derrick. She wasn’t sure why she lied about having kids to him but when he asked if she was a soccer mommy she couldn’t resist.

Slightly embarrassed Jennifer had the cabby drop her off a block away from the strip club. She entered the club trembling.

"12 dollar cover includes one drink" a young man blurted as he had said so many times before. Jennifer started to open her purse. The man reconsidered. "Or are you here to dance?" Jen nodded her head. The man looked her up and down quickly and then smiled. "Cool, you go this way." He hopped up and opened a different door. "Just go down this hall and through that door, they'll get you set up."

She slowly walked down the hall and entered a large room. Several young girls were sitting around smoking. A large woman came over to Jennifer with a clipboard. "Hi, I’m Roberta. You here for amateur night?" Jen nodded again.

"First name?"

"Jennifer"

"Stage Name?"

Jennifer thought for a moment. The best she could come up with was Lacey.

"Topless only, House gets fifty percent. You'll be on in twenty minutes along with Destiny over there."

Destiny gave her a smile and showed her to a seat next to her. She quickly pegged Jennifer as a newbie and Jen gave her the quick low-down on needing money in a hurry which Destiny immediately sympathized with her and introduced her to the other girls. Jennifer let her put her hair in pigtails and they all agreed it made her look much younger. After a bit of lipstick and tons of eyeliner Jennifer was ready as she ever could be.

Walter Jennings had already been in the club for a few hours nursing drinks and watching the regular titties dance by. He had thought about leaving until the announcer introduced the first amateur lady of the night. He watched Jennifer stumble out and his first thought was how stupid a name was Lacey for a girl wearing satin. He laughed to himself.

Jennifer was grateful that two other girls were dancing at the same time as having all eyes on her would have been too much. As it was, it took nearly ten minutes for her to lose her robe. A table full of businessmen finally persuaded her to step off the stage on to their table to dance. With only minutes left in her set and then men chanting “We want tits! We want tits!” did she finally unclasp her bra. Closing her eyes, she let it fall to the table amidst their cheers.

Walter watched the happenings with interest and a smile. The new girl had a nice body and a cute pert set of tits. He would need to get a closer look at them the next time she came out. But by the frightened look in her eye he wondered if she would be back.

Jennifer wondered as well. Back in the dressing room she sat with a frightened puppy look in her eyes. She wasn’t turned on at all. Perhaps this wasn’t what she thought it would be. Destiny sat down and handed her a rum and coke. They talked for a bit and Jennifer relaxed as the alcohol hit her system. Twenty minutes and a second drink gave her enough courage to give it another try.

Back on stage again, Jennifer was more prepared. She made her way from table to table enjoying the way the men looked at her and they way they eagerly slipped dollar bills into her g-string. At least two older men told her that they were in love with her. Another made her blush with his wish of gripping her ponytails like a motorcycle handlebar while she wrapped her lips around his cock.

Walter watched with anticipation. The young blonde was making her way to his table and she was looking better with every step she got closer. She also began to look more and more familiar. By the time she was on his table he swore he knew her, her eyes, her smile. He watched her short dance, marveling at her cute body and puffy nipples. After another moment the song ended and she took his dollars, thanked him and got off the table. Her voice rung a note in his head. Walter was pretty damn sure he knew who she was. And if this was the case it was an age old dream come true.

A few minutes later handed Roberta a bill and asked if Lacey’s name wouldn’t happen to be Jennifer.

“Oh yeah, Nice girl, dire straits, needs the money bad.”

When Jennifer got back to the dressing room she was much happier this time. She had done what she had wanted to do although the thrill wasn’t at all what she had hoped. She figured to grab a cab and head out.

Destiny came over to her and congratulated her on a great second run but added a warning.

“Stay away from the big bald guy he was eying you up and down. He’s nothing but a big perv and’ll stick his finger right up your snatch if you gave him half a second.”

Jennifer recalled him. “He seemed nice enough to me.”

“Oh, old Walter will screw with your mind if you let him. Hell he was just recently fired for making a pass at one of his students, the old fuck.”

“Students?”

“Yeah, used to be a guidance counselor over at central for years. Bet he perved on all the girls.”

“Huh.” Jen blurted in thought.

“Just stay away from him, k Jen? I gotta run and pick up my kid from his dads. Hope to see again soon. Luck.” She gave Jennifer a kiss on the cheek.

Jennifer watched her leave and sat down again. Now this was something different altogether. Mr. Walter Jennings. Yeah, she remembered him well although back then he had a full head of hair and a beard. It was no wonder she didn’t recognize him with clean shaven, bald headed look. Not to mention the 60 plus pounds he had put on. And yeah, he was a pervert. She could easily remember the few times in his office where his look would always drift downward to her chest. It had always made her feel uncomfortable but also always made her nipples get hard. Just like they were getting right now. Maybe she wouldn’t leave just yet.

As she made her way back to the stage she handed Roberta half the tips. Roberta grabbed her arm lightly.

“Hey, baldy seems to remember you. Give him a good show.”

When Jennifer came out for her third dance she was much more relaxed and at ease due to the alcohol and more than a little excited knowing her old guidance counselor would be ogling her, know exactly whose tits he was looking at. She knew he would want more of a show and she was going to give it to him. It was only a matter of minutes before she was down to her tiny leopard panties. Pretending not to notice Walter and the $5 laying on his table Jennifer made her way off the stage and around to the surrounding tables.

Walter watched and waited. He hoped she wouldn’t recognize him as it would surely freak her out and scare her away.

Jennifer had to make her way to the stage often as her panties were quickly loaded with bills as this time she was a bit more accommodating. She played with them even allowing a man in a suit that dropped a ten for her to place his face between her tits as she squeezed them together. Even the fingers that slide one-dollar bills into her panties felt good but what excited her was that he was watching, watching this innocent ex-cheerleader get dirty.

It was only minutes before her set was over that she stepped her tiny foot onto his table.

"It's about time!" Walter laughingly chided her. About time he got a close up view of her tits and ass he had so long coveted.

Once on the table, Jennifer got on her knees and began to caress her breasts while her hips gyrated slowly to the music. Up close she could see indeed it was Mr. Jennings. He may have looked totally different but those glasses and voice gave him away. He looked into her eyes and then exactly as he had done fourteen years ago let his eyes drop to her chest. Except this time there was no tube top, just her bare breasts for him to enjoy. Her hands slid down her legs and picked the five up off the table. Pulling the waistband of her panties out a few inches she tucked in the $5 and let it snap back. All the while Walter's eyes stared intently at her tits.

Jennifer rolled over and stuck her butt up in the air. When she looked back she slightly shocked that he had his face less than an inch from her ass. She felt him put his hands on her ankles, sending an electric quiver throughout her entire body. She quickly rolled over.

"I don't think you're allowed to do that." Jennifer blurted, sounding almost scared.

"Sorry, it was an, umm, accident" He smiled and threw down another five. "Keep going" He had regained his composure now.

Jennifer gladly started again, this time allowing him to put the five in her waistband. His fingers on her inner thigh again sent waves of pleasure through her body. She squeezed her tits right in front of his face.

Walter leaned in and whispered, "20 bucks, let's see the kootch." He slipped the twenty between her squeezed tits.

If it were anyone else in the bar, she would have left the table. Jennifer looked around. It was dark, loud and the two new dancers had most others attention.

Walter wasn't sure what she would do and was slightly surprised when she kept the twenty and laid back on the table. She put her feet on the table with her knees in the air and spread. Then he watched as the once young Jennifer Walsh, voted sweetheart of the year, slide her finger between her crotch and her panties and slowly pull them to the side exposing herself to him. A perfect slit, with lips seemingly swollen and a small tuft of blonde hair. He could barely think of half the ways he wanted to lick/suck/fuck her before she was off the table, leaving him with only a devilish smile.

Walter quickly made his way to the ATM machine.

Backstage Jennifer was all a quiver. She didn't even care about all the money she had. She took a deep breath and fought off the urge to massage her swollen clit. It was time to go now, head back home to bed where she would rub herself into oblivion. She knew she had made Walters' night, perhaps his week, month or year.

A few minutes later Roberta came over to her. Jennifer held up half the money for her.

"Not yet blondie. Gentleman wants a table dance with you."

"Which man?" As if she didn’t know."

"Large bald guy, curtain number three. You want it or not?"

Jennifer thought for a moment. She had already showed him everything. He wanted to see it again. This could be quite fun teasing him.

"Umm, yeah, sure, I guess"

Jennifer got back up and dressed in her original black satin outfit. She smiled at the thought of poor Walter drooling to see her body again.

Walter knew the rules. No touching. He didn't care. He knew she needed money and had already broken one rule by showing him her cunt for 20 bucks. What would she do for fifty, a hundred, two? He waited quietly on the soft velvet couch. He recalled the day in his office as he and the then 18 year-old Jennifer discuss career choices. He would never forget the white tube top she wore that day and how it hugged those cute little tits of hers. He could make out the shape of her nipples through the material. Oh how he wanted to jump to her chair and just pull down the top and suck on them. He had fucked Jennifer a hundred different ways in his fantasies that year. His thought was interrupted by the curtain being pulled back and a timid looking Jennifer walking in.

Jennifer looked around the small enclosed space. "Hello." she blurted nervously.

"Relax, I'm just trying to help you out, I know you need the money."

Jennifer looked at him sharply.

Walter grinned, "One of the girls mentioned it. I can tell you've never done anything like this before."

Jennifer looked down in false embarrassment. "Last resorts suck."

It was exactly what Walter wanted to hear. "Well, we'll see what we can do." he encouraged. "Just have some fun and dance for me for a few, I'll help you along." He knew she must be in some deep shit to have to resort to nude dancing, but he really didn't care a lick about her problems, he just wanted to get his hands on her tits. Nothing in the world like a fantasy coming to reality.

"You're very kind..."

"William, my name is William."

Jennifer perked up, "Well okay William"

Just then the music started. She took off her robe and tossed it on the couch. Walter tossed down a twenty. She began dancing for him.

"Now, off with the top" he said as he threw down ten. Jennifer closed her eyes as she undid the hooks behind her back and removed the bra. With one hand she tossed the bra on the couch while the other instinctively covered her breasts. Walter softly grabbed her elbow and pulled her arm from her chest. He let go when she obliged. At that moment he noticed the slim white band on her tanned finger. Poor little housewife out to save her pitiful hubby who at this moment had no idea how far she was going to help him. It would be farther than she would ever expect.

"Sorry, nerves" she said with a soft smile.

She continued to dance as seductively as she could. She wasn’t sure what was going to happen yet.

Walter tossed out another twenty. “Come closer, let me get a better look at your tits.”

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