tagCelebrities & Fan FictionEverybody Loves Raymond: Debra Does the Babysitter

Everybody Loves Raymond: Debra Does the Babysitter


(fictional story about fictional characters)


Just when Debra Barone thought she had reached the breaking point (or should it be "breakdown" point); she got a reprieve. For weeks she had been trying to pry their former babysitter Lisa away from the Parkers, so she could have a desperately needed night out; and Lisa had finally agreed to supervise the Barone children (twins Michael and Geoffrey, and daughter Ally) on Saturday night. Lisa had been the best babysitter they had ever had; the kids adored her; she never minded when Debra asked her to stay later; and she always seemed to involve the kids in some sort of educational entertainment. She was a freshman in college, majoring in child psychology; so she was an absolute wiz with the children. Unfortunately, she had gotten so popular with the kids, that Debra had gotten jealous, and told Lisa that they no longer needed her services. The Parkers had immediately latched onto her as their exclusive sitter. Almost instantly, Debra regretted her actions. Sure, she could always ask her meddling mother-in-law Marie to baby sit. Her in-laws lived right across the street , and were always ready to help out with the kids; but then Marie always had a way of making Debra feel like a bad mother for leaving the children. Marie was very subtle about her criticisms; always disguising them as compliments...but they were always hurtful comments at heart. Debra would rather not deal with Marie if she could help it. It was no wonder that Marie's two sons were such a mixed up psychological mess.

Ray, Debra's husband, was a sportswriter for NY Newsday; and craved his mother's approval above everything else. In that sense he was a real "momma's boy." He wouldn't contradict his mother's opinion if his life depended on it. His older brother Robert, a sergeant with the NYPD, was even worse because he had an additional inferiority complex when it came to Ray. Marie had them both in the palm of her hand and enjoyed controlling their lives, like pulling the strings on marionettes. Marie's husband Frank was a crude, primitive man whose main joys in life were watching TV and eating. He had provided virtually no parenting for his sons, and yet held them firmly under his thumb. This was Debra's life ...and she had no one but herself to blame because it was she who had convinced Ray to move across the street from them when she became pregnant with the twins.

Debra couldn't pinpoint it, but there was another reason she was happy about Lisa returning as their babysitter: she felt strangely attracted to her. Whenever Lisa was in the room, Debra had a curious tingling in the pit of her stomach, and in her crotch. Sometimes after Lisa had gone home, Debra would lay awake in bed wondering what she looked like naked. Imagining how soft and smooth her teenage skin would feel to the touch. She didn't want to admit it, but she knew there was a sexual attraction there. She had never had any lesbian tendencies before...well, there was that one time in college when she had kissed a fellow student, but she had attended an all-female college, and they had been playing "truth or dare." Why was she having these feelings now; and why were they about Lisa? Was it because Lisa seemed so innocent and vulnerable; or was it because she appeared so fresh and inexperienced?

She knew Lisa was attractive, in the All-American girl sense. She truly epitomized the girl-next-door stereotype. She was probably just over five feet tall, with long curly dark hair. Her body seemed very petite, but her breasts were large for her frame, and jiggled nicely in her blouse. Debra shook her head and realized she was sitting at the kitchen table fantasizing about the breasts of her kids babysitter. She began to scold herself, but her scorn was short-lived, as Frank and Marie burst through the kitchen door for another of their unscheduled (and uninvited) visits. "Why the hell don't I ever lock that door," Debra thought to herself for the hundredth time.

She and Ray had arranged a "dinner and a movie" double date with their friends Bernie and Linda Gruenfelder for Saturday night, and Debra was completely excited about an entire night away from the house (and her in-laws). As she drew the water for a hot bath and poured a cap full of bath oil into the steaming tub, Debra thought about how the oil kept her skin soft, and lamented that even with the oil, she just knew that her skin was not as soft as Lisa's was naturally. There she was thinking about Lisa again...what was her problem. After submerging in the soothing water, Debra lay there letting the warmth relax her body. She marveled at how her tremendous breasts kind of floated on the surface. She was very proud of her breasts, and they certainly gathered their share of attention from Ray's friends. When pregnant with the twins, they had grown to a full 38 D; and had remained that size even after their birth. Ray had nicknamed them "Barnes & Noble." Her nipples had darkened from their former rosy pink, to a light shade of brown; and they did have a very slight sag to them now; but they were still her best feature. As she applied body-wash to her hands and caressed her breasts; her nipples enlarged to the size of gumdrops.

"Mmmm, that's nice," she breathed, as she pinched them. She slowly lowered her hands down her ,still relatively flat, tummy; past her belly button; and followed the line of her bright red "landing strip" all the way to her slit. Her pussy lips were quite prominent, and she rolled the flaps of her labia between her fingers.

She was about to get more serious, when she heard Ray from the other side of the bathroom door shout, " you about done in there Deb? I have to go, and you don't want to be in there when I do."

"That's my husband...pure class," she thought to herself. She yelled back, "I'll be out in a few. You can always use the kids bathroom, you know."

"No, they won't allow me in there any more," he responded. He continued, " ha, good job getting Lisa back from the Parkers. That Bill Parker is such a goody-two-shoes, I bet he rinses his recyclables before putting them in the bin."

"Ray, I rinse our recyclables too; and Lisa is only back for one night, unless we can convince her otherwise," Debra answered.

"Yeah, but everybody knows you're a goody-two-shoes," Ray laughed.

"If you only knew the thoughts I'm having about our babysitter, " she mused to herself, as she finished washing and arose out of the tub. As the cooling water dripped off her naked body, Debra couldn't resist a quick look in the full length mirror on the back of the door. She was beginning to get a tiny bit of a droop in her ass cheeks, but her legs were still firm and shapely. All in all, she was pleased with what the reflection showed her. After dressing quickly, she prepared some microwave (Marie would have a stroke) mac and cheese for the kids dinner. The doorbell rang at precisely six o'clock, and Debra knew it must be Lisa. As she went to open the door, she suddenly felt flushed and nervous. The feeling increased when they greeted each other with a perfunctory hug, and she felt Lisa's breasts brush momentarily against her own. Lisa was dressed in a plain white blouse and plaid skirt; reminding Debra of a Catholic school girl's uniform...something she was very familiar with. After exchanging pleasantries, the Barones left for their night out; and Lisa began helping the kids with their homework.

The Barones and Gruenfelders decided to see an early movie and have dinner afterward that night so they could take their time and enjoy the food. They were having such a pleasant time that Debra called home and asked Lisa if she would mind staying a little later. Lisa, as usual, was agreeable as long as Ray would give her a ride home because her bus stopped running at midnight. Debra had a couple more glasses of wine than usual that night and was feeling quite tipsy when they arrived home. She told Ray to wait in the car and she would sent Lisa right out. Lisa was so involved in what she was doing that she never heard Debra open or close the kitchen door. When Debra stepped into the living room she saw Lisa sitting back on the sofa; her skirt up around her thighs; her plain white panties down around her ankles; and her hands in her crotch. The TV displayed the faint images and wavy lines that Ray got when he tried to watch the scrambled porn channels. Debra stopped dead in her tracks, and the movement caught Lisa's attention. Her face grew scarlet, and she shoved her skirt back down, as she stammered for something to say.

"I'm so sorry Mrs. Barone...the kids are all al seep...I just don't know what came over me...I'm so sorry," she pleaded, tears forming in her blue eyes.

Despite her intoxicated and shocked condition, Debra thought quickly and responded, "well you should be sorry young lady. Doing something like this with my children in the house." Debra suddenly realized that she was not only aroused at what she had seen, but she now had the upper hand. "Unless you want me to tell the Parkers about their good little babysitter; you will agree to sit with our kids whenever I ask...and you will be here Monday morning wearing the same clothes, at exactly nine o'clock to discuss this," she announced.

As she reached down under her skirt to pull up her panties, Lisa readily agreed to the conditions. She quickly gathered up her things and went to the car where Raymond was waiting. Debra flopped down on the sofa, completely drained and out of breath. She changed the TV channel and sat back to think about what had just transpired. She was totally in charge now...Lisa was completely at her mercy. Her mind was flooded with images and ideas for their Monday meeting. Did she dare instigate any of the scenarios she was concocting? Was she bold enough to cross the line of sexuality with Lisa? She thought of Lisa sitting there in the very same spot on the sofa, playing with herself. Debra hadn't been able to actually see between Lisa's legs; but there was no mistaking what she had been doing. Debra's head was spinning from the alcohol, and now from the possibilities awaiting her. She lay in bed that night unable to sleep; daydreaming about the unlimited possibilities of her situation. She was in a position of ultimate power over another adult probably for the first time in her life. As she finally drifted off to sleep, she thought of Monday morning, and a huge smile swept across her face.

Sunday seemed to drag by in slow motion for Debra. They had invited Marie and Frank to brunch, and, as usual, Marie had criticized every dish that Debra placed on the table. Frank had no complaints; he just shoveled everything set in front of him into his mouth. The kids seemed to be especially annoying all day, and Ray was just his normal lump of flesh. Debra supposed she was also easily agitated because she was so nervous about tomorrow. She had decided to take a firm, direct stance with Lisa from the start. The truth was, she could never bring herself to discuss the delicate situation with the Parkers; but she must never confess this to Lisa. She knew she had to maintain the upper hand, and not let Lisa sense her weakness. She must make sure Lisa knew the dire, long term consequences if she didn't obey her commands.

As soon as Ray left for work, and the kids boarded the school bus on Monday morning; Debra gathered a few items and took them up to the bedroom. She found that she was shaking with a combination of fear and anticipation. Under her pink terrycloth bath robe, she was wearing the flimsiest, sheerest bra and thong panties that she owned. They were black lace and she had purchased them a couple years ago for a special occasion; but had never taken them out of her drawer until today. Her large brown areola were plainly visible through the sheer lace, and the thong barely covered her slit; leaving her bright red landing strip exposed. Before she had a chance to reconsider her plans, the doorbell rang; startling her so badly she almost wet herself.

"Its now or never," she told herself as she descended the stairs to the living room. She gathered her composure, rehearsed a stern look on her face, and opened the door to find Lisa cowering on the doorstep. She couldn't believe how cute Lisa looked in her school-girl outfit, with that sheepish look on her face. Debra scowled, and firmly announced, "glad to see you're punctual Lisa; now come inside and we'll get started."

Lisa weakly replied, " thank you Mrs. Barone...get started with what?"

"Why, your punishment and chance for redemption, of course. If you want that whole incident to remain our secret, you will follow my directions without hesitation or refusal...is that clear ," Debra replied.

"Yes, Mrs. Barone...anything you say," Lisa surrendered.

Debra closed and locked the front door, as Lisa stood in the living room awaiting her punishment.

"We will begin in the bedroom, so march on up there now," Debra instructed.

With a quizzical look on her face, Lisa mounted the stairs in front of Debra. Debra followed a few steps behind so she could admire Lisa's legs as they disappeared up under her plaid skirt. Once inside the bedroom she normally shared with Ray, Debra ordered Lisa to completely disrobe.

"What...take my clothes off...what do you mean," asked a puzzled Lisa.

"That had better be the last time you question my orders; or I head straight to the phone to call the Parkers, and your parents," said Debra, raising her voice. Her heart was racing; she couldn't believe she was actually pulling off the stern act.

Lisa's lower lip began to tremble, and Debra was afraid she was going to cry; but she instead began to unbutton her plain white blouse. When she was finished, she lowered it off her shoulders tossed it onto a nearby chair. Her rather plain lace bra was the next item to go, as she reached the clasp behind her and the straps fell down her arms. Her breasts were perfectly round B cups, with cute pink nipples slightly on the top of the mounds. Her areola were very puffy and inviting, and Debra couldn't help thinking that they would fit perfectly in her mouth. She nodded for Lisa to continue; and Lisa unzipped the side of her plaid skirt, before letting it drop to the floor. To Debra's surprise, this revealed Lisa was wearing bright red, totally sheer bikini panties.

As she began to lower them, Debra stepped forward, saying, "no, let me."

Debra dropped to her knees in front of Lisa, grasped each side of her panties, and slowly pulled them down her pale legs. As Lisa stepped out of them, Debra noticed that although Lisa did not shave her pubic area; it was very neatly trimmed. She had trimmed her hair into a distinct V shape, and had cropped the hairs very short, so that her slit was plainly visible. Debra's face was even with Lisa's pussy, and she observed that moisture had formed on her puffy pussy mound. As Debra stood, she trailed her hand lightly against Lisa's mound; causing her to shiver and goose-bumps to form on Lisa's skin.

Debra backed a few steps away from Lisa, facing her, and deliberately shrugged her robe from her shoulders, allowing it to pool at her feet. She could have sworn she saw Lisa lick her lips as she unclasped her sheer bra and tossed it aside, baring her magnificent breasts. They were a full 38 D, and she was most proud of them. Debra reached down to her sides, untied the tiny thong, and let it drop to the floor; revealing her pussy.

"Mrs. Barone, I never realized your breasts were so large...they're spectacular," Lisa ventured.

"Thank you Lisa, you may now lick my nipples," answered Debra , in a business-like tone.

Lisa willingly advanced toward Debra; dipped her head; and lovingly touched just the very tip of Debra's left nipple with the end of her tongue. Debra shivered at this first intimate touch, and felt weak-kneed as Lisa began to lick her entire breast. Lisa cupped Debra's impressive tit in both hands, as if serving it to herself, and suckled at the gumdrop sized nipple. She gently took the rosy nipple between her teeth and nibbled. Lisa repeated this procedure with the right breast, noticing how engorged the nipples had become. Debra stood silent as she felt wetness form between her legs. It was as if Lisa was worshipping her body, and she loved it. Lisa didn't wait for further instructions, as she began licking her way down the center of Debra's trembling body; running her hands down Debra's sides as she descended to her knees. When Lisa had kneeled in front of her, Debra ceremoniously spread her feet apart, giving Lisa access to her moist pussy. Lisa nuzzled her face into Debra's crotch, her brown hair tickling Debra's thighs, and teasingly drew her tongue from the bottom of Debra's slit, all the way to the top; where Debra's clit was already beginning to make an appearance. She reached up with both hands, and used her thumbs to spread Debra's damp cunt lips apart, revealing her pink inner flesh.

Debra was afraid her knees were going to give out, as Lisa wasted no more time, and slid her tongue deep into her pussy. As Lisa fucked her with her tongue, Debra purred and grabbed Lisa's head, holding it in place between her legs. She looked down and saw the erotic sight of Lisa's face wedged in her crotch, completely covered in her juices. Lisa quickly withdrew her tongue, and nibbled on Debra's clit as she jammed two fingers into her soaking slit.

Debra's knees buckled as she groaned, " oh my God that's good." She held Lisa's head firmly in her crotch, almost smothering her, as her body shuddered in orgasm. If she hadn't used Lisa's body to steady herself, she would have collapsed onto the floor.

Lisa gently pulled away from Debra's grip, and stood up; putting her arms around Debra's soft body and placing her lips on Debra's. They kissed tenderly and gently at first; then it evolved into a passionate, urgent embrace, their arms tightening around each other. Debra could taste her own cum on Lisa's lips, and it excited her. They broke their embrace,and taking her by the hand, Debra led Lisa to the bed; where they both climbed onto the center. They sat facing each other, their legs outstretched and intertwined. Debra reached out her hands, and for the first time in her life, began to fondle another woman's breasts. Lisa's tits were small compared to her own, but were perfect handfuls; and her extremely puffy areola were very exciting. Her nipples hard like pencil erasers, almost pointed toward the ceiling. Debra leaned forward and suckled at first one rosy pink nipple, then the other. She ground her left nipple between her teeth, probably harder that she should, and watched Lisa close her eyes and bite her lower lip.

Debra sat back and casually asked, "you're not a virgin, are you?"

Lisa shyly responded, "no, but I've never been with a man."

Debra continued, "the reason I asked..." and she leaned over to the bedside table to retrieve an object she had placed there earlier. It was a fourteen inch pepperoni stick, a Waldbaums special, still encased in plastic. She had already spread a condom over each end, and was now squirting baby oil over its entire length. "I thought we could share," Debra continued.

Lisa's eyes brightened as she answered, "that's very resourceful, Mrs. Barone."

Debra loved the way Lisa's legs felt intertwined with her own, and although she had entered into this relationship wanting to punish her, she was beginning to feel extremely attracted to Lisa. Debra scooted her body closer to Lisa until their crotches were only about a foot apart. She held the improvised cock in both hands, nudging it against Lisa's slit. Lisa reached down with both hands and spread her lips wide apart, as Debra gradually slid the rod into Lisa's cunt.

As the cock went deeper, Lisa put both hands flat on the bed behind her for support, as she loudly moaned, "mmmmm."

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