Amanda Pleases Herself

Amanda Pleases Herself

Divorced and seeking pleasure

Toys and masturbation

Dildos, vibrators, anal, lesbian

Disclaimer: All people having sex in this story are over 18. Any resemblance to anyone living or dead is a coincidence.

Amanda sat eating a microwave pasta entrée as she opened her laptop. She was curious about something that had come up in a meeting today. The VP of sales had informed them that they had a new marketing company flogging their products. One of the team members had asked what their new flogger looked like. It got a good laugh from most of the people in the room but a few, including Amanda, had blank faces.

She Googled flogger and was surprised at the sites that came up. Most were for sex toy or BDSM sites. Even more curious, she clicked on one and it opened to show her leather whips. As she read, she learned that they were also called cat o' nine tails, or simply a cat. She smiled ruefully and was going to leave the site when she spotted a huge, oddly shaped dildo. As she read, she discovered that it was made for anal penetration.

To her surprise, she was turned on by the thought of something going in her butt. Her ex had never been one to experiment and had not really cared for any kind of sex, truth be told. Amanda found she was squirming in her seat, rubbing her ass against the chair. She hurriedly removed her skirt then pulled down her pantyhose and panties. She reached around and rubbed a finger around her bottom hole. It felt good until she tried to insert a finger in her dry pucker. She pulled her panties and hose up and went to her bedroom.

She sat on the bed and removed all her clothes. Naked, she laid on her side and pumped some lotion onto her hand then rubbed it into her butt crack. She left a little extra right in the center, slowly working a finger around the rim before inserting it. Her sphincter loosened and let her finger glide into her rectum. She moaned at the new sensations she felt. Why the hell have I never played with my butt hole she wondered.

She brought her other hand to her pussy and was surprised at how wet she had become from playing with her ass. After a few minutes of playing she inserted a second finger in both her holes. It felt wonderful to be massaging her two most intimate openings at the same time. It wasn't enough to make her come, however.

She got out of bed and rushed into the bathroom to retrieve a towel and her dildo. She laid the towel on the bed then laid down on her side. She was going to use the dildo on her pussy while fingering her ass, then changed her mind. Rolling onto her back she put lotion on the fake dick and raised her hips so she could position the toy to penetrate her ass. She eased herself down, feeling it burn as it started to expand her sphincter. She whimpered at the first-time pain then suddenly, it was in her. She continued to lower her butt until she was flat on the bed. she marveled at how full she felt. She spread her legs enough to get her whole hand on her crotch and started working three fingers into her sex. It didn't take long at all before she brought herself to a very satisfying orgasm. She could feel a bigger one building and started slapping her pussy and rubbing her clit. She came and squirted fluid out onto the towel. Her hips lifted off the bed and the dildo shot out of her ass when her pussy muscles contracted. She laid there panting and chuckling to herself, if only I had a video of that toy exploding from my bum, she thought.

When Amanda had recovered, she cleaned herself and the toy. Putting on a bathrobe she spent the next two hours looking for interesting things on the various sex sites she found. In the end she made three purchases before showering and heading to bed.

It took four long days for her order to arrive. She found she was more excited than a kid at Christmas. Her first gift to herself was a weighted silicone butt plug. It was two inches in diameter and the body was four inches long. It had a large T handle and weighed nearly a pound. This was the one she had specifically ordered to wear at work. It would be exquisite torture to have to hold the weight in while she moved around the office.

Her next present was a sixteen-inch long cock shaped dildo with three bulges in the shaft. The head was an inch and a half, the first bulge was two inches, the second was two and a half and the third a whopping three inches. It had a suction cup attached so she could stick it to the bottom of the tub. It would let her bounce her ass on it to her heart's content.

Her last item was a pink U-shaped vibrator that was made to hit your G spot and clitoris at the same time. It had a wireless remote that would be ideal for using at work.

It was only seven p.m. but Amanda couldn't wait any longer. She wet the suction cup, sticking it to the bottom of the bathtub. Starting the water, she took off her clothes. After dumping some bubble bath in the water, she giggled as the tub filled and the bubbly water rose up to cover the monster cock.

She was so excited she was shaking at the mere thought of that monster invading her tight ass. Well, she thought to herself, my ass won't be tight for very long. Squirting some lube onto her hand, she massaged it into her sphincter. Brushing the bubbles from the dildo Amanda added lube to the head and shaft sticking out of the water.

She stepped into the tub and holding the sides eased her ass onto the huge toy. She shuddered when it touched her ass and she nearly lost control of her arms. She laughed nervously at the thought of falling ass first and ramming the fake cock up her little butt.

Letting herself down increased the pressure on her pucker until she thought she would have to give up. She let out a breath and tried to push out at the same time as letting herself down. Her sphincter opened and the entire fat head of the dildo entered her ass. She was so surprised she relaxed her arms a bit too much and she sank down until her ass hit the first bulge.

Amanda paused, breathing hard and trying to adjust. This was further than anything had ever been in her butt before. She breathed out again and let most of her weight rest on the first bulge of the monster dildo. Her ass seemed to open on its own and soon the first bulge was safely buried in her.

Instead of resting she kept letting herself down. When her butt touched the second bulge, she let all her weight down. It wouldn't go in any farther and she whimpered and panted. She rested her arms for a moment then rose up until her sphincter pulled against the first bulge. Amy let her full weight fall. Her butt hit the second bulge and it stretched but wouldn't go in. It felt so good and hurt so nicely at the same time.

She contented herself with rising and falling with six inches of fat cock in her ass. Not bad for the first time she thought. She would let her sore butt have a day off then wear the weighted plug to work. When she came home after having that fat plug in her all day, she would be able to take the second bulge, maybe even the third. She fingered her clit and came, thinking about how much it would hurt to have the entire sixteen inches up her butt.

Amanda got up an hour earlier than normal the next morning. If she was going to have a huge, weighted plug in her ass all day she needed to be cleaned out. She gave herself an enema and was satisfied it had done its job.

Amanda greased the blunt nosed toy up and then spread a generous amount on, and in, her rectum. She closed the lid on the toilet and holding the plug upright sat down on it. It slowly stretched her sphincter, hurting her more and more as it slipped into her. She nearly gave up at one point, the pain was so intense. Just as she was going to back off, she realized she was closer to the toilet than she had been. She reached a hand behind her and felt that only two inches of the fat body remained. This knowledge let her relax and sink the rest of the plug into her ass. It was a huge relief to have the whole body in her rectum. Her ring slowly closed around the small shaft and the T handle fit snugly in her ass crack.

She found she was panting from the effort it took to get the plug in her butt. She stood up and the plug slid out of her the length of the short shaft. She instinctively clamped her legs together and tightened her ass muscles. She gradually relaxed her muscles and soon realized that the plug wouldn't come out on its own. It did put a lot of pressure on her anal ring that felt incredible. She chose a pair of bikini panties that were too small to wear comfortably, thinking they might help hold the plug in.

She sat down on the toilet to pull them on and nearly had an orgasm. The handle hit the seat and shoved the toy back in all the way. With shaking hands, she pulled the panties up her legs then gingerly stood to pull them up the rest of the way. The weight slid out again and tried to push the panties off.

Amanda took a few tentative steps, marveling at how the weight stimulated not only her ass, but her pussy as well. She stepped into the long, loose skirt she had picked out. After tucking her white blouse into the skirt, she slowly sat down to slip into her high heels. Standing, the plug obeyed the laws of gravity and slid down, with the high heels tightening her calves and butt it felt completely different.

The drive to work was an interesting one. Just working the floor pedals shifted the heavy plug in her and put an utterly delightful pressure against her G spot. Of course, there were no parking spaces close to the door. She had to walk nearly a block to her building. She was panting and had to stop just outside the doors to recover from two orgasms.

Amanda had the elevator to herself and she used the opportunity to lift her skirt and rub her clit through her panties. She came just as the elevator stopped, giving her a few seconds to compose herself. As she walked to her office, she could feel the moisture leaking into her panties.

Her secretary Ramona brought in her coffee, mail, and phone messages. It was a busy morning and she nearly forgot about her toy until she stood up to retrieve a file. Amanda had to hang onto her desk for a moment to let the rush of excitement pass. Her first few steps were agonizing trying to make sure the plug stayed in her ass. She found the file and sat down slowly. When the toy was firmly seated in her ass, she scooted her desk chair to the right so she could watch out the door for anyone coming toward her office.

Pulling her skirt up and exposing the still wet crotch of her panties to the air felt divine. Slipping her hand down the front of the tight panties she inserted two fingers into her vagina. It felt much tighter than normal, she could feel the back of her fingers pressing against the fat plug and it excited her to the point she only lasted thirty seconds before letting loose. Thick fluid coated the fingers and she glanced out the door before putting them in her mouth and licking off the tasty treat.

She spent the rest of the morning concentrating on her job. Occasionally she would bring her hand to her nose and sniff the faint odor that lingered on them. When Ramona brought her lunch order and put it in front of her she wrinkled her nose, then recognizing the aroma of hot pussy, smiled and winked at Amy before swaying her hips outrageously as she left the room.

Amanda should have been embarrassed at having been found out like that, but her pussy and ass, hell her whole body, felt too good to care about it. By two p.m. she had finished her work and used the last three hours to find any excuse to stand up and walk around. By five she had come three more times. On her way out the door her secretary very pointedly asked her if there weren't anything she needed some help with. Ramona seemed disappointed when Amy smiled and said no, go ahead and go home.

Amanda stood to go and felt the wet fabric of her skirt on the back of her thighs. She had to wait nearly a half hour before everyone else had gone. She went to the women's restroom and took off her skirt. There was a huge wet spot that showed up plainly on the blue material. Washing the wet area in the sink and using paper towels to blot it dry worked fairly well. She held it under the hot air hand dryer until she was satisfied no one would notice that the skirt was still a little damp.

The long walk to her car produced an orgasm so strong she had to stop and wait for it to finish before she could move. As Amanda started walking, she knew she would come again before she got to her car. This time when it hit she kept walking, it took nearly a minute to get to her car and she came the entire time. She had to lean over and rest on her car hood to recover enough to make her shaking legs obey her.

When her ass hit the seat, she laughed to herself. So much for all the work at drying her skirt, it felt as if she were sitting in a puddle. Concentrating on her driving, she made it home safely.

In the house she stripped on the way to the bathroom. She started the tub then leaned over the vanity and pulled on the T handle. Her ass resisted her efforts to dislodge the plug. She pulled harder and cried out at the pain. After resting a moment, she lubed her fingers and slid them into her butt around the small shaft.

Now well lubricated she squatted on the bathroom floor and pushed out as hard as she could while giving it a firm steady pull. Her sphincter opened and the huge plug squirted out of her ass. Standing up and moving made her feel empty, she missed the fullness. Well, she thought, in a minute I'll be even fuller.

Amanda pushed the long dildo into the tub bottom and climbed in, surprised at how shaky her arms were. She laughed to herself thinking, well, fifteen orgasms in a day will do that to you.

When the large head of the fake cock touched her asshole, she didn't hesitate, sinking down, the head popped right in, continuing her descent the first bulge proved to be no barrier. Her sphincter was stretching around the second bulge in seconds. Pausing after taking a deep breath, she let her weight fall onto that larger bulge. Grudgingly her ass opened and accepted the increased girth. When her asshole clamped down on the shaft under the second knot, she felt her stomach. The tip of the monster was right behind her belly button. She had over a foot of huge fake cock in her ass. She rotated her hips while holding her hand on her belly feeling the large end of the toy stir her guts.

Amanda was eager to try for the whole thing in her hot ass. She rose all the way off the mock cock and spread a handful of the lube on and in her ass, then let some dribble over the head of the toy. She sat down hard, ramming the toy in to the third bulge in one try.

Pausing to pant for a moment she settled onto the largest part of the dildo. She could feel her asshole stretching and almost willed the thing to spread her ass. When half the bulge was in she forced her butt down and it swallowed the huge diameter. She found herself sitting on the bottom of the tub and panting loudly. She could feel her rapid heartbeat in the ring of muscle surrounding the huge dick and moaned at the pain, pressure and extreme pleasure it produced.

After regaining her composure, she started moving her hips on the toy. She brought herself to the brink and stopped. God, she thought anything that feels this good should have a name. In a flash it hit her, the only appropriate name for the dong was Max.

Feeling for the head she found it was nearly under her rib cage. How in the hell had her ass been pushed this far out of shape? She didn't know, but life would never be the same, of that she was sure. She began to ride Max seriously and once her orgasms started, they kept coming. Pulling off the dildo she sprayed the wall of the tub with her pussy juice, then whimpering at the empty feeling in her ass, quickly jammed herself back down.

Amanda used her foot to open the tub stop and drained the water from the tub. Now she could squirt everywhere with Max still deep in her bowel. She kept coming until she was shaking so badly, she couldn't move anymore. She lay in the empty tub shuddering and twitching until she got cold. She considered filling the tub again but when she moved, she thought getting the toy out of her abused ass was probably a good idea. Trying to lift her hips up, the combination of her weak limbs and the largest knot wouldn't allow it.

Reaching between her legs she got a fingernail under the suction cup, releasing its seal. She managed to get her feet under her and got to her knees. She squatted in the tub and used the same removal technique as she had on the weighted plug. Gripping the suction cup, she pulled and pushed out. Her asshole stretched over the widest point and then pop, pop, pop the three bulges came out and Max laid there in the bottom of the tub. Amanda wearily climbed out and knelt next to the tub. Reaching over she opened a door under the vanity and pulled out cleaning supplies. After thoroughly washing the toy, she cleaned the tub of the lubricant residue.

Standing up and looking in the mirror, she was surprised at how matted her hair was. She had to wash the sweat and mascara from her face before going to bed. She would shower in the morning. On the way to her bed she giggled at how tenderly she was walking. Lying on her side she reached back and fit two fingers in her ass without touching any skin. Amanda thought she better give her ass a day of rest before trying any new tricks.

Waking the next morning she reached to see if her butt had closed. It had, but her sheets were a mess from the lube that had seeped out of her before it had. She stood up and winced at the pain in her rectum. In the bathroom she saw Max standing at attention on the edge of the tub. My god, was that whole thing really up my ass?

Despite all the attention her pussy had gotten in the last day Amanda was somewhat amused to find she had to rub out a quick one while in the shower. She was nearly out the door when she smiled and went back to the bedroom and slipped her vibrator and remote into her purse. In case of an emergency, of course.

When she sat at her desk, Ramona came around and stood next to her. Setting her coffee and mail on the desk she bent down and made a show of inhaling deeply. Catching only a hint of Chanel No. 5, she seemed disappointed.

Amanda smiled and said, "Better luck next time."

The morning passed quickly and after lunch Amanda was looking forward to a quiet afternoon to end the workweek. Ramona stuck her head in the door and said, "Monthly budget meeting in ten minutes, boss."

Amanda groaned saying, "I was hoping everyone forgot. Ted Danvers is the most singularly boring person on the planet."

"Yes, but the memo said it would be a short meeting," Ramona said encouragingly.

Blowing Ramona a raspberry, she said, "That means only two hours of listening to him drone."

Gathering a notebook and pen, she started for the door then went back for her purse. In the restroom she sat in a stall, pulled her panties down and inserted the new U vibrator. She practiced with the remote, finding that on the low setting she couldn't hear anything but still felt a pleasant buzzing sensation deep in her pussy. She thumbed the remote to turn on the clitoral stimulator end of the vibe but was disappointed that it was so loud. She wouldn't be able to use that part in the meeting at all.

Amanda stood, finding out that her panties held the toy tight to her crotch. She smiled at the feeling in her pussy when she walked. She couldn't wait to try the weighted dildo and this vibe at the same time. Maybe she would practice using both over the weekend.

Taking a seat at the far end of the conference table, she had an empty chair on either side of her. The meeting was only ten minutes old when she casually reached a hand into her purse. She made sure she hit the right button and was rewarded by a silent vibration in her hot pussy. As time went on it became harder and harder to concentrate on what was happening in the meeting. She was very aware of what was happening in her crotch, however. The people sitting on either side of her were nearly asleep, so she tried turning the power up a notch. It gave her a bit of a jolt, but she still couldn't hear a thing over the ambient noise of the room.