Caroline's Solution

She couldn't deny her excitement. She had suddenly, over the course of about thirty minutes, worked herself up into a sexual frenzy that she had never experienced before. She took her left hand and finished her glass of wine as her right stuck up awkwardly in the air, now set aside for the single purpose of penetrating her ass.

She carefully poured another large glass of wine and took a deep breath. Feeling the warm glow of the shiraz, she hiked her legs up higher and further apart to expose more of her ass for her finger to explore. Without any further experimentation or half-measures, she penetrated herself using her middle finger until it was entirely inside her ass. Pulling and pushing it in and out, produced a very sensual feeling. She liked it when she did it in the shower, but it was even better while relaxing on her bed. After a few minutes of using her finger, her repeated penetrations soon became insufficient to maintain the same level of stimulation.

Pulling her finger out and finding it to be clean, she wiped it with a tissue and got up to wash her hand. She prepared a soapy washcloth in the bathroom and wrung it out, so she wouldn't have to get up again. Slightly frustrated in her current position, she took two more large gulps of wine as she thought about repositioning herself for better access to her butt.

While she stood drinking her wine, she looked in the mirror at her body and noticed in the reflection the padded chair she had in the corner of the room. Taking it to the other side where she had the full-length mirror, she set the chair directly in front, facing it. Her excitement grew as her rearrangement of her bedroom furniture quickly turned into a sexual ritual. A ritual that she knew would culminate in her first anal masturbation session.

She lay a towel down on the chair, gathered her supplies and sat down about three feet away from the mirror.

'Oh my gosh, this is so kinky!' she thought. She sat with her ass hanging slightly off the edge of the chair and spread her legs apart, then hooked each on a chair arm. Her perfect asshole was now much more easily accessible and graphically on display in the mirror. Clutching her leg behind her left knee with her left hand, she used her right middle finger to run circles using increasing pressure around her tight hole.

'This is a much better position.' She toyed with herself, inserting her middle finger inside, then drawing it out half-way, and back in again. She increased her tempo and discovered she needed a lubricant that would allow her finger to slide without as much resistance. The baby oil did the trick. Using it, she was able to glide her middle finger in and out with a much faster pace and with less drag against her rectum and anal ring.

After several minutes, she arrived, once again, at the place where her middle finger wasn't producing the same level of stimulation as it was when she first started. She used more oil and combined both her index and middle finger in a sort of one on top of the other approach and began working them into her ass. It worked, she got them both comfortably inside, and was able move them both in and out after a few times. She stuck her two fingers deep inside of her and looked at the lewd image in the mirror. Her heart beat loudly in her chest. "Oh god!"

She soon increased her pace and was now wanting a deeper, more filling experience.

Wiping her hands off with her washcloth, she reached down and grabbed her brush. Her hands trembling with excitement, Caroline coated the handle with what was too much Vaseline, held the bristle end in her right hand and very slowly began to open herself up to the very first foreign object she had ever had up her ass.

The tapered tip entered effortlessly, but it expanded to a more expansive girth toward the middle that caused her to stop, frozen with about two inches inserted into her. She gawked at the sight of the oak-colored brush handle sticking into her body. It was both thrilling and perverse to her. She also noticed that as she took her focus off of trying to penetrate herself, her anus relaxed and seemed to welcome more of the wooden handle into her body. She used the opportunity to slide more of the five-inch handle into her until she had what she estimated to be four, relatively thick inches sticking into her ass.

She was impressed by how much progress she had made in such a short amount of time and realized that her bottom was far more accepting of sexual play than she had ever thought possible. She also had to admit that this was an unexpected outcome to her experiment. Leaving the brush handle in her ass was providing her more pleasure than she could have imagined, and given her slow, meticulous approach, she hadn't hurt herself or made a mess. Even now, as she stared at herself with the brush sticking out of her ass, she was turned on. She felt that an anal orgasm could indeed be possible.

Caroline was getting extremely aroused, but she didn't want the experience to end painfully, so she dared not try to touch her clit directly. Instead, she began to fuck herself in the ass with the brush handle. The thrusts began soft and slow, then, as her stimulation increased, she began increasing her speed and depth. Soon she was grabbing the bristle-end tightly and fucking herself much harder than she had when she first began. Her thrusts utilized the entire handle of the brush. The slapping and squishy noises she was making brought her near to climax.

She was further stimulated by the obscene thought that entered her mind: 'I'm fucking my butt with a wooden brush handle!'

As the brush handle entered her more deeply each time, the side of her forearm began to graze the very tip of her extended clit.

"Oh my God!" She exclaimed loudly. It was a soft enough touch to produce a pleasurable response without any pain. Her arm only grazed the tip of her swollen clitoris. It happened again, then again.

"Oh...yes...yes...YES!" The fourth time she glanced against her clit she had a tremor-inducing orgasm. As she looked at the thick, wooden brush handle embedded in her ass, and her legs spread more widely than she had ever had before, her body tensed, flexed, and then thrashed violently.

"Ummmmm...Ooooh!...Aaaahhh! Ggggggodddddd!" Her powerful orgasm overtook her body and mind. She was flooded with a pleasure she had never thought even possible. Caroline was immediately taken to another place, another world. Her eyes fluttered and she saw purple and red dots speckle her vision.

"Unnnn!"

She started laughing. It was a large, booming, laughter of pent-up sexual release.

"That was crazy!" She smiled at her reflection in the mirror.

As her climax subsided, she released the brush and watched it shoot out of her ass and drop onto the floor, in that brief moment, she watched her asshole wink at her; closing itself tightly, then opening up to the size of the brush handle, then closing up again. She thought this was the most obscene, and yet strangely sexy thing she had ever seen.

Caroline started laughing again, still looking at herself in the mirror, her legs now together and placed on the ground, she leaned back and stretched her arms over her head, smiling a huge, satisfied grin.

'It wasn't totally an anal orgasm but having the brush in me really changed the quality of it. I felt it in my butt!' Caroline sipped on her wine and began to clean and replace the items she had collected. Her sleep that night was restful and luxurious. Curiously, Caroline's religious objections to her own adventures in sodomy did not surface as she fell fast asleep.

Caroline had a very relaxing, yet productive weekend working on a draft of an article she should have finished Friday and enjoying her time with her friends at church. She felt a little tender from her first anal experiment, so she decided to give her butt a rest.

That week at work, she heard nothing from Bob or Geoff in the breakroom. She was considerably happier than usual as her orgasm that past weekend had cheered her up considerably. She felt invigorated, and more than just a little bit naughty.

On that Friday, Caroline had an intense anal session with her brush and was able to have another orgasm much the same way she had the previous weekend. She was delighted that she was capable of having consistent orgasms with her newfound interest. Her stance on the evils of sodomy had been nearly pushed out of her mind.

The next day, Caroline awoke refreshed and feeling alive. Last night's orgasm helped to improve her overall mood. She went for a short run ending at the coffee shop for a well-deserved latte. On her walk back to her townhouse, she could feel a difference in her ass; she felt looser, more relaxed, and she could swear that she was walking with more sway to her hips. She smiled and wondered how often she could masturbate like she was with the same fantastic results.

'I wonder if my bottom can take having my hairbrush handle in it every day?' She wondered.

In the shower, Caroline cautiously reached her hand around and played with her sphincter. It was a little sensitive, but not at all hurt or sore like she would have imagined. As she was washing herself, she kept reaching around and putting her middle finger deep inside her. It slipped in much easier now. She was still surprised that she had discovered something so pleasurable that she once found to be so utterly repulsive.

Caroline wasn't happy about the source of her new discovery: Geoff. She recollected that it was his words that guided her during that first night of anal play, although she wasn't entirely conscious of it at the time.

She remembered him saying:

"Preparation is everything. You can't just shove it in her. It takes time to get her ready...stretching her ass, a little at a time, and some stimulation is very helpful..."

She took his advice and it worked. As she thought about the other parts to his conversation, she began to consider that perhaps she had been too judgmental toward him.

'Maybe he wasn't so bad after all. Maybe he's not actually a pervert,' she conceded.

After her shower, Caroline planned to run some errands that day: drop off her dry cleaning, return a dress, pick up a few groceries; the usual Saturday chores. While at the dry cleaners, she saw a colorful sign blinking in the shopping strip across the street that caught her eye: "Cupid's Adult Novelties." It was a new store in the new series of shops that couldn't be more than a few months old. After placing her clothes in the back of her car, she made a quick dash across the street to the new store.

She nervously pushed the metal handle and entered. To her relief, there was a woman behind the counter, and no one else in the store. The place itself was rectangular-shaped and stocked full of various sexual products. There were racks of gift items like penis candles for cakes, crude party games and favors, lubricants, and other sex related items along the walls. The books and DVD's were toward the back and lingerie occupied the racks in the center of the store. Caroline didn't immediately recognize or understand all that she saw.

She didn't know exactly what she was looking for, but she remembered that last part of what Geoff had said about dildos and plugs. Ultimately, she was looking for something that she could use instead of the brush handle, something more manageable, more comfortable, maybe even a bit larger, and more penis-looking.

Caroline stood frozen at the entrance to the store until a voice woke her from her daze.

"Do you need some help?" The woman behind the counter looked to be in her forties and had a short, bleached-blonde men's style haircut. Caroline assumed she was a lesbian.

"Oh! No. My god." Caroline laughed uncomfortably. She was just now aware that it was the first time she had ever stepped foot inside a shop like this.

"Sweetie, why don't you do yourself a favor and just tell me what you're looking for. There's no judgement here." The woman smiled warmly, putting Caroline's apprehensions at ease.

"Well, I was looking for something for...I like...no, I would like..."

The woman crossed her arms waiting patiently for Caroline's nervousness to subside.

Caroline blushed deeply, but since she was already in the store, she thought she might as well just come out with it. "Do you have something like a dildo or a plug for anal sex?" Caroline shrugged her shoulders and left them in the upward position squinting her eyes in a state of frozen embarrassment.

The woman's reaction couldn't have been more nonchalant.

"Over here." She stepped around from behind the counter and led Caroline toward the middle of the store, then to the back, against the wall. All sorts of toys were hung on a display board in clear plastic packages and boxes with plastic windows.

She pointed, "These are the plugs. Here are the vibrators and dildos, most are dual-purpose, but the ones that have a firmer surface are better for anal. We have different lubes up front. If you have any questions, just let me know." She smiled and turned, walking back to the register.

Caroline stared up at the black pegboard with dozens of dildos and packages of butt plugs. She was instantly overwhelmed. The different sizes, colors, materials, and shapes. Vibrating or not? Remote control or manual? Natural skin-colored: black, brown, or white? Artificial colored: pink, purple, silver, or clear? She decided she needed to think very clearly about what she was doing so she wouldn't have to embarrass herself by having to make a return trip. She also assumed they didn't take exchanges or offer refunds.

She decided she wanted to get a dildo first, as that was the most important to her mind and her new sexual interests. She was looking at the plugs and couldn't figure how to use one or even what purpose it served, so she focused on the dildos. She wanted to get something she could use on a regular basis, as well as something to be used maybe only now and then, perhaps something larger for special occasions.

Caroline's nervousness turned to sexual excitement as she began to envision each dildo and how she would use it.

She selected a hard, white skin-color, six-inch vibrating dildo that was submersible and had variable speeds to it. She thought it could serve as her regular one. She chose a life-like, white skin colored, thicker, seven-inch dildo to be used for every now and then, or if she wanted to move to something bigger. It too had a vibrating feature and even had veins running around it like a real penis.

Now that she had two dildos selected, she went back to the confusing butt-plug section. She still didn't know how they should be used so she picked up a random plug and quietly approached the salesperson, feeling especially awkward carrying the plastic packages containing the dildos through the store.

"Can you help me select a plug, please?" Caroline winced.

"Okay, let me see what you've got there." The brusque woman grabbed Caroline's dildo selections and looked at them.

"These are good for both vaginal and anal." She put them on the counter. "Okay, a plug is usually used to give you constant stimulation while doing something else, like if you want to be stimulated anally while you were being penetrated vaginally, you know?"

Caroline wanted to run out of the store. She had never had such a sexually descriptive conversation with a stranger.

"People also use them to help prepare them to take something larger in the near future. To get loosened up a bit so it's not so uncomfortable later."

"Oh!" Caroline was speechless and considering all this new information.

"See the sort of diamond shape?" The woman pointed to the plastic object in the see-through package, "It tapers to this flat disk at the bottom so that it doesn't go any further. It's shaped so it stays in. Hell, you could walk around with it inside you and not worry about anyone knowing, or about it coming out." She chuckled softly as she considered the object.

Caroline felt her face flushing red again.

"The largest dildo you bought is seven inches long and five inches in circumference, so use the thickness part of the dildo to help estimate the correct size for a plug. Try a five-inch thickness, one that doesn't go too deep. That should be good." She walked back around the counter and resumed reading her book, as if this was a conversation she had all the time.

"Thank you." Caroline went back and chose a three-pack of black-colored butt plugs that included 4, 5, and 6-inch diameters. They looked too big, but given the woman's advice, they were the right choice.

She quickly picked up a large bottle of lubricant and took the plugs to the counter.

"You did alright for your first time!" The woman was smiling awkwardly trying to be friendly.

"Is it that obvious?" Caroline turned red again.

"Oh, Sweetie, it's all right. That's what I'm here for. In fact," she reached out her hand for Caroline to shake, "I'm Trudy."

Caroline returned her firm grip. "Caroline."

"I manage the place. We get a lot of women in here, a few men, but the owners are female, and we try to make it comfortable and safe for women to come in without a bunch of men loitering about."

"That's nice to know, thanks!"

Caroline took her bag of toys across the street and back to her car, finished her errands, and once home, excitedly took her second shower of the day. She felt she needed to give herself a good cleaning now that she had her new toys.

In a red tank top and a white pair of panties, she began to set up her masturbation area.

She moved her chair in front of the mirror and placed a towel over the seat. Then she opened the dildo and plugs and washed them before setting them on a table that she slid over next to her chair. Her lubricant and wash cloth ready, all she needed now was her wine.

She felt extra naughty since she was about to use a dildo on herself for the very first time, and the fact that she was going to use it anally, and even during the day, made her shake with anticipation.

Caroline sat with her legs spread wide, each one hanging over the padded arm of the chair. Her hips were angled upwards, so she could see the reflection of her asshole in the mirror. She smoothed on the lubricant she bought on her smaller dildo and teased herself by rubbing the realistic-looking phallus against her pink sphincter.

"Ummm." She loved the build-up, and the heady arousal thinking of what she was about to do.

She used her left hand to spread her cheek further away from the other and slowly guided the dildo through the tight ring of her forbidden opening until the artificial head disappeared within.

She panted, waited, and slid more inside herself. This was different than the brush. Although it didn't look much larger than her wooden friend, it felt much wider. The feeling was incredible. The dildo felt more life-like, it felt much better than the perfectly straight, cylindrical brush handle. It looked sexier too. After waiting a few more moments, she continued until she was at the hilt. She could feel the increased girth stretching her wider than the brush handle did. The additional length gave her a more stimulated feeling than the brush.

"This is a lot better!" she said.

'Oh God. This is so exciting!' she thought. She drew the artificial penis in and out of her body slowly, then more rapidly, until she was fucking herself with a slow, steady rhythm. The sight of the flesh-colored penis disappearing into her asshole was thrilling. She left the dildo embedded in her ass and reached over to get the larger one.

Switching in on, to its lowest vibrator setting, she settled her body into position. Caroline used her right hand to steadily pump her ass and held the vibrating dildo in her left bringing it down ever so gently to barely touch her engorged clit.