Beverly’s Obsession

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Tem 19, 2022 // By:analsex // No Comment

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(This story is a continuation of the story Plan B. If you want to know more about these characters read that one first. Otherwise, enjoy.)

There had not been a day since it happened that Beverly had not thought about what she had seen. Now, every time she thought about it her pussy got wet. Really wet. I mean, let’s be honest, Beverly had watched porn before. But she had never watched two people have actual sex before, in real life, in person, right in front of her; especially when some of the sex was anal sex! It dominated her waking thoughts. She wondered how it must feel. She wondered what sort of orgasm it would induce, if any. Would it hurt? Would it damage her butthole? How does one even begin? These were the questions that always popped into Beverly’s head when she thought about the unknown world of anal sex. So, she Googled it.

Beverly’s search carried her into the vast and varied world of cyberspace where she learned a great deal about a great deal more than she had intended to learn. Still, while she became more knowledgeable, her curiosity was not satisfied. So, she continued to explore. But now her exploration wandered into the realm of porn; anal sex videos, to be specific, and the studying of the performers’ technique and body language. She paid attention to the non-verbal cues that body language and facial expressions offered. She tried to determine if the female performers really enjoyed being fucked in the ass or was it all simply good acting. Again, a sense of frustration from not knowing left her unsatisfied.

One morning in the shower as Beverly distributed the soapy lather all over her naked body, she became aware of how hard and sensitive her nipples had become. She twisted them roughly with her fingers and enjoyed the warm buzzing that rumbled deep in her vagina. Her right hand instinctively slid down her body where her fingers caressed the fleshy folds of her pussy. She felt it swell and open as she teased it. Her index finger and ring finger deftly splayed her labia as her middle finger, her fuck finger, mashed her clit back and forth against her pelvis. Almost immediately Beverly began to shudder.

It was not all that unusual for Beverly to masturbate in the shower, especially when Dan, her husband, had been out of town for a week on a three-week business trip. She missed the morning sex on Hump Day, the only weekday they engaged in morning sex. He would have taken her doggie style. She would have moaned her orgasm into the pillow she clutched as he slid his fat thumb into her asshole. God, she loved when he did that. She hoped one day she would be brave enough to take his big ol’ dick in her tight little butt-hole. But she just wasn’t sure.

Grabbing her ass cheeks with both hands, Beverly pulled the fleshy globes apart and enjoyed the sensation of water trickling into the crack of her ass. She marveled at how the rivulets of water teased her asshole with the unpredictability of a probing tongue. She let go of one cheek and stuffed two fingers into her tightening pussy and imagined her husband’s fat penis filling her vagina. Using the hand that still held her butt cheeks open, Beverly slid the tip of her little finger around and around her puckered anus until, with a little exhale and squeal, she slid the entire digit into her asshole, all the way past her second knuckle. In her mind, it was her husband’s massive cock that slid into her virgin asshole. The fingers stuffed in her pussy could just barely feel the tip of the pinky stuffed in her asshole. Gently they rubbed against one another as she fucked herself closer to orgasm.

Soon, Beverly’s knees buckled, and a massive orgasm enveloped her. She reflexively pulled her fingers from her pussy and steadied herself in the slippery shower, trembling and moaning as the water cascaded over her bowed head. Her butt hole rhythmically flexed around the finger still buried in her anus as her orgasm continued to pulse through her body. As she slowly shook her head and regained her composure, she again wondered what a huge fucking cock would do to her when she had this type of reaction from just a little finger. Squeezing the muscles that would evacuate her bowels, Beverly slid her finger from her anus with a moan. It was at that moment that Beverly realized that she had an anal sex obsession. She now understood that, at this point, the only thing that would satisfy her would be to experience anal sex.

Now that she had decided that she was going to experience anal sex, she still didn’t quite know how to, exactly, specifically, explicitly, proceed. She wanted a consultant. She needed a consultant. The only person she knew who engaged in anal sex and would have a working knowledge of how to proceed was her eighteen-year-old babysitter, Amy Ferguson. But asking Amy Ferguson for advice concerning anal sex would be problematic on many levels. For one thing, she would probably have to confess to Amy for having spied on her that time when Amy’s fuck buddy, Marcus, had fucked Amy in Beverly’s living room. You know that voyeuristic moment I spoke of earlier that güvenilir bahis is now dominating Beverly’s waking thoughts and making her panties wet? Yeah, that one.

And then there is the age thing that made things kind of weird. Ten years is a long time, but it didn’t seem that way to Beverly. She knew that the ten years between eighteen and twenty-eight were probably more significant than the ten years between twenty-eight and thirty-eight. Yet, here she was, the older, more experienced big-sister type seeking advice from a neophyte. It made Beverly feel rather ashamed that she didn’t know more about anal sex, personally. Was that something she should have explored in college?

And what about the “creep” factor? How would Amy’s mother feel if “some perverted woman” in the neighborhood, for whom her daughter babysits, was initiating conversations about anal sex? How would she, Beverly, feel if this were her own daughter who had been approached by some woman she may be working for in the neighborhood for information on the ins and outs of anal sex? She began to worry that maybe this all wasn’t such a good idea. And then, that image of Marcus sliding his huge black cock deep into Amy Ferguson’s asshole invaded Beverly’s train of thought.

“Fuck it,” Beverly decided out loud with a smirk. “If my daughter had been letting some boy fuck her in the ass in ‘some woman’s house,’ on ‘some woman’s couch,’ I guess her discussing anal sex with a neighbor would be the least of my worries.”

Beverly decided she would confront Amy about what she had witnessed and use it as leverage in extorting some highly coveted anal sex training in return. Good old black mail.

Mrs. Beverly McClain was stooping so low as to black mail a high school student just to get what she wanted; what she needed. She longed for someone to coach her on how to accept a fully erect penis in her virgin ass, and if this was what she had to do to make that happen, then so be it. Such was the nature of Beverly’s obsession.

One Saturday in late June, Beverly had dropped her daughter off with her parents for a two-week visit; a break from mothering that she looked forward to every summer. That same Saturday, Beverly told Amy and her husband that she had been invited to a jewelry showcase party that evening from 6:00-9:00 P.M. She had planned for Amy to babysit her two-year-old daughter, Olivia, but we all know now that that had just been a ruse, part of her plot to extort information from Amy. Dan was still out of town on his business trip and would be for two more weeks. Beverly had decided to confront Amy when she arrived that evening to babysit.

Much to Beverly’s delight, Amy had committed a major faux pas in her ability to remain stealthy about her deviant lifestyle. Beverly found the empty gold foil packet that had once held a condom stuffed in the seat cushions of her living room couch. This gave Beverly the entre she desired when confronting Amy.

Amy let her backpack slide from her shoulder as she entered the McClain’s house. She pushed the door closed behind her and stopped dead in her tracks. She couldn’t figure out why Mrs. McClain was sitting on the stairs and waiving an empty, gold-foiled condom wrapper in front of her face.

“Amy Ferguson,” said Beverly using her best “disappointed mother” voice. “What is this?”

“I swear Mrs. McClain,” gushed Amy. “Marcus brought that from home! I’d never take one of Dan’s, I mean Mr. McClain’s without asking!”

“One of Dan’s?” exclaimed Beverly, both stunned and confused. Dan had condoms? Why would Dan need condoms?

“I wouldn’t even help myself to one of your tampons without asking first,” pled Amy, her face full of genuine concern.

Beverly was now a little disappointed at Amy’s attempt to play ‘little-miss-innocent’ with that tampon comment, and before she knew it, she had blurted it out.

“Oh, really? Just like you asked permission for your chocolate fuck buddy to come into my house, when I’m not there, and fuck you on my couch?”

The words rang like a bell, and like a bell, they lingered in the air until the vibration that caused the ringing stopped. Both women stared at each other through the silence; Amy wearing a wide-eyed expression of guilt, while Beverly raised an inquiring eyebrow. And just like that, the atmosphere changed. Amy realized what Beverly’s accusation revealed.

“Oh my god! You little pervert!” squealed Amy, smiling with incredulous glee. “I knew someone was watching us! You watched Marcus fucking me in the living room, didn’t you, you little pervert!”

Beverly could no longer keep a straight face and looked at the floor with an embarrassing grin. She couldn’t bring herself to look at Amy. She was so busted.

“I know, I’m sorry,” explained Beverly smiling sheepishly. She pulled her hair back behind both ears and bravely looked back into Amy’s eyes. She decided she should just own this one. “We couldn’t stop watching and we didn’t want to scare you,”

“Wait! What? We?” This time Amy’s voice cracked with incredulity. “Dan? I mean Mr. McClain…watched güvenilir bahis siteleri too? Whaaaaat?”

“Yeah, and he was fucking me while we watched you guys fuck,” continued Beverly, almost reliving the excitement she had felt watching the wanton couple.

“Stop…! No..!” squealed Amy putting both hands to her face. “You fucking perverts!”

“Oh, you have no idea,” smiled Beverly, now feeling as if she were conversing with an old friend, a peer.

“Oh my god, I love it!” exclaimed Amy. “I baby sit for a couple of fucking perverts!”

“And my fucking babysitter is a little anal slut!” giggled Beverly as she teased Amy back.

“You know it, girl,” grinned Amy while holding up her hand for a high five.

“But I gotta say, Ms. McClain, sometimes, even though it feels so good, it’s too much work to get ready for it, you know? It’s just too much trouble.”

“Well, not exactly.” Beverly’s expression, though smiling, grew more earnest. “I’ve never had anal sex.”

Now it was Amy’s turn to be stunned and confused.

“Shut up! No way! Wow!” exclaimed Amy. Then her wide-eyed smile suddenly transformed into an expression of deep concern. “Aw, Mrs. McClain…,” consoled Amy with a reassuring caress of Beverly’s forearm.

“Please. Call me Beverly,” said Beverly as she realized that their relationship had suddenly changed very dramatically.

“Aw, Bev,” sighed Amy compassionately, though with a playful touch of sarcasm in her voice. She gathered Beverly in her arms in a warm, tender embrace. “We can’t have that, can we?”

Beverly’s mouth hung open slightly as she literally studied Amy’s actions. This eighteen-year-old was more mature and put together than most of Beverly’s friends! Who knew?

“Can you help me?” asked Beverly dramatically, in mock distress, confident that she had finally found her coach.

“Of course, baby,” said Amy as she led Beverly to the couch and sat down beside her, all the while holding her hand in a comforting, reassuring manner.

Beverly began to relax and feel at ease with the choice she had just made in allowing Amy to coach her in the ways of anal sex. She liked Amy’s youth and vivacious personality. Hell, she liked everything about Amy.

“I just don’t know exactly what to do,” explained Beverly. “I mean, I went online and everything but, I guess I want to be able to ask someone specific questions, you know.”

“Totes,” said Amy who was listening intently to her new friend’s situation. “I’m glad you asked for help before trying to take a cock as big as Dan’s anally.”

Beverly paused, tilted her head sideways, and narrowed her eyes at Amy.

“How do you know how big Dan’s cock is?” asked Beverly accusingly.

“Oh, please Bev,” complained Amy. “As if a cock like that could ever be hidden, especially when it’s hard.”

Beverly sat with her mouth wide open in disbelief.

“You must know Dan checks me out every time I come over here, right?” asked Amy. “I love watching him try to hide his erection! I have the same effect on the boys at school, not to mention the faculty.”

Amy smiled confidently. Beverly realized that there was a lot about Amy that reminded her of her younger self, though she wished she had been half as confident as Amy when she was eighteen.

Amy paused and looked around the room as if searching for something. “Where is Olivia, and don’t you have a jewelry showcase to get to?”

Beverly simply smiled. Now it was Amy’s turn to be confused.

“Well, I sent Olivia to spend two weeks with my parents and the jewelry showcase was an excuse to get you over here so I could get you to help me learn how to have anal sex,” explained Beverly.

“And Dan?”

“He’s away on business for the next two weeks.”

“Well, aren’t you a lucky mommy!” chirped Amy. “That’s good because it gives us plenty of time to prep and practice.”

“I can’t wait to get started,” squealed Beverly as she grabbed both of Amy’s hands and squeezed them in her excitement.

“This is going to be fun,” said Amy, sharing in Beverley’s excitement. “We’ll prep this coming Saturday for practice, and then again the following Saturday in preparation for Dan’s homecoming! He’ll be so surprised!”

“I know, right?” exclaimed Beverly, continuing to pull on Amy’s hands with glee. “What do I need to do first?”

“First, you need to go to the drugstore and buy six bottles of Fleet enemas and a big bag of Skittles.”

“Ok…,” said Beverly with a questioning tone.

“You may want to use a drugstore on the other side of town if you feel self-conscious,” added Amy.

“What are the Skittles for?”

“Well, this is the hard part,” explained Amy. “You should only eat fruits and vegetables between now and Wednesday. Your last meal will be Wednesday, so you’ll have 48 hours to get all of the shit out of your system.”

Beverly’s eyes widened.

“If you get hungry Thursday or Friday, munch on a few Skittles. They’re all sugar and won’t leave much behind to have to eliminate.”

“I guess my figure will benefit iddaa siteleri from this journey as well,” reasoned Beverly. Both women chuckled.

“I’ll come over next Saturday night at 7:00 to show you how to prep,” instructed Amy. “I’ll tell my parents that you want me to babysit.”

“Thank you so much,” said Beverly.

“No worries, Bev,” smiled Amy. “See you next Saturday!”

As you can imagine, the week between last Saturday and next Saturday was a difficult one for Beverly. Without her husband and daughter, her life was terribly empty. Thankfully, Beverly kept herself occupied with Spring cleaning chores, rearranging closets, cleaning up files on her computer to the point where, by the time Saturday did arrive, she felt good about herself and all that she had accomplished.

At 7:00 sharp the doorbell rang and in walked Amy in her standard outfit — a blue Oxford shirt tied under her boobs to expose her flat tummy and belly button ring, a pair of frayed Daisey Dukes worn so low on her waist that the top of her butt crack was visible, and a pair of cheap, rubber flip flops. She dropped her backpack by the door as usual, but this time the two women embraced each other warmly like old friends.

“Ready?” asked Amy.

“Ready,” replied Beverly.

Amy held Beverly’s hand as she guided her student into the kitchen.

“First, we fill the electric kettle and boil some water to take upstairs with us,” explained Amy. “We’re going to dump those Fleet bottles and fill them with the boiled water. We don’t need the enema chemicals and the boiled water is sterile.”

“See, that’s the kind of information you just can’t get by just Googling it,” complained Beverly.

“Bev, I told you, I got you,” said Amy with a smile.

Once the water had boiled the women climbed the stairs to the master bathroom. Amy placed the kettle on the vanity behind the Fleet bottles Beverly had neatly lined up between the double-sinks. She then turned on the shower and began unbuttoning her shirt.

“It’s time to shower and shave,” said Amy as she walked out of the bathroom and laid her shirt on the bed next to her backpack. From it, she pulled out two, pink butt-plugs, each about the size of a small Jalapeno pepper. Next, she pulled out two black butt-plugs, each shaped like a three-dimensional spade as found on playing cards. Then, like a sword from its scabbard, like Mary Poppins from her carpet bag, Amy drew a chocolate-brown, ten-inch rubber dildo that wiggled and bent from its sheer weight and length.

Beverly looked on nervously, quite unsure of what to do. She watched as Amy tied her shoulder-length, blond hair into a knot high upon the back of her head, then pull a clear shower cap from her backpack to cover her hair. She saw Amy un-hook her bra and free her perky, C-cup breasts. She marveled at the way Amy’s narrow waist flared dramatically into curvy hips and a bubble butt that was perched high on shapely legs as she hooked her thumbs into the waistband of her panties and shorts, whisking both garments from her body to the floor.

“Well, don’t just stand there,” said Amy as she walked back into the bathroom. “Get un-dressed.”

Beverly inhaled deeply through her nose and pulled her T-shirt over her head. Her white bra strained to corral her DD-cup breasts. She let her breath out slowly as she pulled her un-clasped bra down her arms and let her titties lay proudly on her chest.

“Damn, girl,” said Amy with a smile. “You’ve got some world-class titties there!”

All Beverly could do was blush and turn her back as she rolled her yoga pants and panties down her tanned legs.

“And an ass that would make a Kardashian jealous!” said Amy as she grabbed two handfuls of Beverly’s abundant booty.

“Stop,” screeched Beverly as she swatted Amy’s hands away.

“Get your shower cap,” said Amy. “We don’t have time to blow-dry hair this evening.”

Beverly tied her hair into a knot high on the back of her head just as Amy had done. She then bent to retrieve a shower cap from one of the doors under the vanity. Amy was still fixated on Beverly’s curvaceous ass and could not resist caressing both glorious cheeks as they presented themselves to her as Beverly bent at the waist.

“I hope my ass looks this good once I reach 28.”

“And had a kid,” Beverly quickly added. Both women again giggled as they stepped into the shower.

As if they’d been showering together since birth, Amy and Beverly washed and caressed each other’s body. They both appreciated having someone to wash their backs. Their silence made the process seem almost ritualistic. They smiled at each other as they proceeded. Finally, Amy broke the silence.

“Now this is how I wash my butt,” she explained spinning around and pointing her pert backside at Beverly. She dragged the bar of soap back and forth in her butt crack until the entire crevice was filled with foamy bubbles.

“At this point, I slide my little finger into my butthole as far as it will go and slowly pull it out, and then I slide my middle finger into my butthole as far as it will go and slowly pull it out, and finally, I push my thumb all the way into my butthole and let it stay there until it feels comfortable,” said Amy, demonstrating each action as she described it. Beverly was glued to every action.

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