Caroline's Solution

She carefully set the curved head of the penis onto the very tip of her protruding nub. The effect was instantaneous.

"Aaahhh! Gggodd! Oh, Gggoddd! Oh, Gggoddd!" Caroline dropped the vibrator while holding the dildo deep in her ass. Her tight hole gripping onto it near the base.

"Uuuhhh! Uuuuhhh!" Her powerful orgasm caused the dildo to shoot out from her body and land on the floor in front of her seat.

Again laughing, Caroline smiled and shook her head. "That took all of three minutes!" She took several deep breaths. "Wow!"

Never in her sexual life had she had so many intense, pain-free orgasms. This was special. It was new and exciting, and it was consistent. This new approach to her sexuality changed everything for Caroline.

Feeling relaxed and content, Caroline left all her sexual paraphernalia exactly where she had dropped it and curled up in bed for nap. After a good, hour-long rest, Caroline gleefully stripped her shirt and panties off. She wanted to try one of the butt plugs.

Sitting back in her masturbation chair, she coated the plug with a little lubricant then reached around and inserted the smallest, four inch one into her body. She could feel her sphincter open around the widest part, then close around the narrower base, holding it in place. She marveled at the effectiveness of the simple design.

She walked around her condominium naked; walked past her full-length mirror and turned around, 'You can barely tell it's in there!' She smiled, impressed with the discovery. 'I could wear this under my panties when I wear a skirt!' Her mind played out scenarios where she was in public wearing a plug. 'What a sexy little secret that would be!'

Monday arrived all too soon, and Caroline found herself squatting down at her desk at ten-thirty in the morning listening to Bob and Geoff.

"I'm done. Giving up on the dating scene for a while." It was Geoff apparently discussing his weekend with Bob.

"Yeah, what happened?"

"Nothing. Absolutely nothing," Geoff lamented.

"You mean you didn't get any responses to your ad requesting anal sex from hot-looking women?" Bob laughed at his own joke.

"Not funny, man. How about I got no messages, likes, or emails at all? Fuck it, Bob. I'm done for a while."

"I think if you would just put this ass fetish out your mind and just dated a woman you found interesting; you'd do better." Bob's tone became serious noting his friend's angst.

"I told you about that because I enjoy it more than vaginal, it's not like I have to have anal. I just like it a lot more than vaginal. I don't put anything about it in my profile."

"Well, that's good!" He chided.

"No, it's not 'good.' It means that women aren't interested in me, and there's nothing I did or said to warrant this lack of interest."

Trying to improve his friend's mood, Bob asked, "Hey, I've been meaning to ask you, how do you know if a woman wants anal without asking them outright? Wouldn't it scare them off to say, 'hey, do you want me to fuck you up the ass?'" Bob wanted to experiment with his girlfriend, Lisa, and wondered if Geoff had any insight about how to get the ball rolling.

"Quit messing with me, Bob."

"No, I'm serious. Like, how would I approach the topic with Lisa?"

With a deep sigh, he responded, "Sometimes it's clothing. A G-string or thinner-style thong can be a sign. I've dated a couple of women who went anal pretty quickly who wore those kinds of underwear. But more women are wearing these styles of underwear these days so that can't be the only thing to consider."

"Lisa has a few pair of thongs. Keep going."

"What I do is when I'm having sex, I reach around and touch her asshole. Just touch it, nothing else. I put my middle finger against it when she's on top or if I'm behind her. If she likes it, she'll usually say something, if she's indifferent, she may hold off until it happens again, then she may say something. If she doesn't like it, she'll probably tell you right then and there. Of course, all women are different."

Geoff continued, "A few women I've dated let me finger them a little but didn't seem to be into the idea of anal sex. Usually a really hot, sexual relationship will get around to discussing it at some point, you know?"

"That's good to know. I might try something this week." Bob looked at his watch, "I've got to go."

Caroline heard them both leave the breakroom, so she stopped pretending to fix her power strip against the wall and sat back in her chair, now pretending to read a draft she was supposed to have finished by lunch.

'That was a hot conversation. I wonder what I would have done if Stephen had touched my asshole when he was trying to have sex with me? At the time, I would probably have kicked him out of bed.'

Caroline sighed, then got back to the draft.

After a meeting with her supervisor after lunch, Caroline began to crave another orgasm. She was fantasizing about going home and getting her dildos out for some after-work fun.

On her way home, she dropped off some dry cleaning and glanced at the adult sex store she had visited over the weekend. 'Maybe I'll stop by.'

Without thinking about it further, she found herself in the store.

"Back so soon? How are you, Caroline?"

"Hi, Trudy!"

"Did everything work out alright with your selections?" Caroline appreciated Trudy's pleasant way of saying 'how are the dildos and butt plugs working for you?'

"Yes, just fine. Thank you for your help! I have another question, and I know it sounds naïve, but I really don't know who else to ask." Caroline approached the register.

"Go ahead, dear. What's on your mind?" Trudy put down her graphic novel.

"What's a 'G-string?'"

"A G-string is like a thong, only a lot thinner. We have some over here." Trudy walked around the sales counter to a circular clothing rack in the middle of the store.

She held up a lime-green garment that, at least to Caroline, looked like some sort of stringy contraption that a stripper might wear.

"This part is the front, and this part's the back." Trudy held it up by the sides to illustrate.

"That doesn't offer much protection, does it?" Caroline held the tiny thing in her hand.

"Well, you don't wear it during that time of the month, but protection is not what they're for. A lot of women wear them to avoid panty lines, or to just feel sexy." Trudy held the G-string up and turned it around, "you'd definitely need a trim to wear this one," she chuckled.

She turned around and lifted her shirt up a little. "See, I'm wearing one now."

Caroline observed a thin red cord sitting horizontally just above Trudy's hips with another red cord of the same size running vertically fastened with a small, gold ring disappearing below her jeans down between the cheeks of her butt.

"Oh! Yes, I see. That is considerably thinner than a thong." Caroline went back to looking at the other G-strings on the rack before she started to feel uncomfortable.

"Thank you. I'll look for my size."

Trudy went back to her place behind the register and returned to her novel.

After several minutes, Caroline returned with a handful of the miniscule underwear.

"Anything else I can help you with?" Trudy began removing the security magnets from the G-strings.

"No, and thanks again for being so helpful!"

On her drive home, Caroline questioned her purchase. 'Why did I buy these?' She picked up the black plastic bag and held them up as if examining them from the outside of the bag. 'Is it because of what Geoff said?' Despite her questionable motives for buying the under garments, she found that she couldn't wait to get home to try them on.

Naked in all but her new, lime-green G-string, Caroline turned before her full-length mirror and commented aloud, "Now I see why women like wearing these." She could feel the thin cord in the back, it pressed tightly against her anus and gave her a very naughty feeling.

"I like that!"

On a whim, she inserted her smallest plug and arranged the cord of the G-string so that it fit over the bottom of the plug.

"Oh, God. That's sexy." She said in a soft tone. Caroline put on a shorter, white skirt and a blue tank top with a sports bra and decided to pick up a few groceries at the store. She wanted to test out wearing her plug in a public setting.

The drive to the market was almost too stimulating to be safe. She had to fight the urge to pull over and fuck herself silly with the butt plug. Once in the store, she realized that it was more difficult walking around normally than she had thought. She didn't trust that the plug would stay in and regretted selecting the smallest one for her outing. 'One of the larger ones would have stayed in better,' she thought.

What Caroline didn't realize was that her sphincter was getting accustomed to having something stretch it out. As she finished her shopping, she realized she had been smiling the entire time she was in the store. She liked her new sex life, although she was beginning to feel the pangs of loneliness return. She wanted companionship. Dildoes were not a man. Sex or no sex, she missed the intimacy of a serious, monogamous relationship.

Caroline had three masturbation sessions between Saturday afternoon and Sunday evening, all producing monumental orgasms. During the last two, a thought fueled her excitement. 'I want to wear a plug and a G-string to work.'

Her decision was final. Tomorrow at work she would try it out. She packed her purse that night with two butt plugs- the medium and larger size and a regular pair of panties in case the G-string became uncomfortable.

She awoke earlier than usual for a Monday morning. After showering and completing her morning prep, she decided it would be best to insert the plug at work rather than have it inside her during her commute. She wore a form-fitting, grey pantsuit that would highlight her lack of panty lines. Her white, pullover blouse and black heels were the perfect complement to her outfit.

"Good morning, Caroline." Rachel, the office assistant for her editing department looked up at Caroline from her desk. "You're in a good mood today! Fun weekend?" She smiled.

"You could say that. How was yours?" Caroline paused as she spoke with the thirty-something brunette.

"By the look of it, not as fun as yours." Rachel's attention returned to her computer as Caroline continued on to her desk.

After booting up her computer, Caroline took her purse into the ladies' room and inserted the medium-sized plug into her awaiting ass.

"Ooh!" She was surprised at how good it felt as it slid inside. Caroline quickly covered her mouth with her hand, thankful that she was alone in the restroom.

'I like this. I wonder if anyone can see it?' She left the stall and turned in front of the half-mirror in front of the sink. You could see a small bump, if you looked closely enough, at the seat of her pants. This was an exciting sight to Caroline who felt like she was having anal sex in the office.

She left the ladies' room and took a stroll around the floor, practicing her walk and feeling sexual for the first time in years. She decided that the larger plug made all the difference in the world. She dropped off her sack lunch in the breakroom and settled into her desk to try and work.

'There's no way I can get much work done like this.' After ten minutes, she became so distracted by her plug that she had to make a quick trip to the restroom and remove it. Now finally able to concentrate, she finished up two articles for next week's deadline and reorganized her file drawer.

"Hey Bob, what's up."

Caroline could just make out Geoff's voice from the breakroom. She didn't want to miss the conversation, so she sat on the ground and took out a few files that she had already organized to pretend she was still sorting them. Just as she was flipping over the papers in the first file, she had a naughty thought.

'I wonder if Geoff would notice my thong if I were to bend over in front of him?'

Caroline's body shook with excitement at the thought of teasing her oblivious anal mentor. She took off her jacket and squatted on her feet as if she were picking something up in her heels. She reached her hand behind her and felt for the gap between her shirt, her G-string, and the waist of her pants. She smiled as she felt skin between all three garments. It would not only be noticeable, but obvious.

'That's it, I'm doing it!'

Caroline ventured into the breakroom.

"Hello gentleman," she greeted the two, who were to her relief, alone sitting near the refrigerator, in their usual manner.

"Hi there, Caroline." Bob and Geoff stopped talking and watched the gorgeous blonde enter the space.

Bob nudged Geoff with his elbow and nodded toward Caroline as she opened the door to the fridge. Geoff pointed at Caroline with his thumb and shook his head then put his hands together as if he were praying. The entire office knew Caroline was a religious person. Although Geoff found her irresistibly attractive, he didn't consider her as one with whom he would have any interests in common. Besides this, he considered Caroline out of his league. She was clearly a "10" and he had often categorized himself as a "6" or "7".

Geoff and Bob looked on nonetheless and made small talk with her.

"Good weekend, Caroline?" Geoff asked.

"It was okay. Boring." She turned around and smiled.

"You too, huh? There's a lot of that going around," Bob said.

The two men were still looking at the slender blonde when she squatted down moving her lunch from the top to the bottom shelf.

Geoff was first to see it. He hit Bob in the arm and motioned to Caroline's lime-green G-string wedged between the top of her butt cheeks. The two men were staring in disbelief, mouths open, eyes locked on the unexpected but extraordinarily sexy sight. Her G-string cord was clearly visible as was the very topmost part of her perfect ass.

Before either of the men could say another word, Caroline stood up, turned on her heel, and headed out of the breakroom back to her desk.

"Have a great day, guys," she said as she left.

"You too!" Geoff offered.

Caroline walked as fast as she could around the corner to her desk and dropped to the floor to hear what was said, hoping they had seen her sexy underwear.

They had.

"Are you kidding me? Jesus. I would have never guessed she would wear a thong like that," Bob said.

"That was definitely a G-string, my friend. I didn't think she was the type. Wow!"

"Well?" Bob asked.

"Well what? Oh...you mean because of the G-string you think she's into anal? Well, I'm definitely calling it a good sign, but the verdict is still out."

"Hey, why not ask her out, Geoff? Rachel says she's single."

"No way, man. She's like a runway model. She would never go out with me." Geoff looked into his coffee now feeling sorry for himself.

"You know, I saw a talk show a few years ago where they interviewed these insanely beautiful single women and asked them questions about dating. They all said that they get lots of catcalls when they are out alone in public, but they never get asked out. They said they thought it was because guys were too intimidated by their good looks." Bob was trying to give his friend a little courage.

"Yeah, I could see something like that being true. I don't know, maybe. I'll see if she has a profile on CitySingles. You know, Google her or something." Geoff and Bob left the breakroom.

Caroline felt her pussy become painful as she grew wet from overhearing the conversation.

'How informative,' she thought.

That night, Caroline researched the dating site CitySingles and placed a profile, then quickly deleted it. She sat back in her chair staring at the screen.

'This just isn't my style. Besides, I'm not sure what sort of man I want. I don't want someone like any of my past boyfriends. I'll probably need someone who is a bit on the wild side to go for the kind of sexual experience I now require.' She closed her browser and lie on her bed.

Caroline was so profoundly moved by her recent ability to have orgasms, and her new fondness for ass play that she could only think of having a boyfriend that knew what they were doing as far as anal sex was concerned.

For the first time, she considered Geoff as a potential suitor. Perhaps not a serious romantic choice, but someone she knew would certainly have an excellent understanding of how to meet her sexual needs.

She sprung up from her desk and rifled through her closet. She was thinking of a pair of thin nylon pants that were actually more like yoga pants but looked professional enough to wear at work.

"Here they are!" she declared aloud.

The next day at work, she wore a purple G-string and brought her largest butt plug. Her plan was simple. Be as obvious as possible without actually coming out and asking Geoff to go on a date.

***

"Finally, Ten-twenty. Break time!" Caroline had been anxiously looking at her watch all morning waiting for the time when Bob and Geoff would be in the breakroom. Something told her that after the show she gave them yesterday that they would be there at the exact time today.

She took her purse into the ladies' room and inserted her largest plug. She could have easily had an orgasm if she had inserted it a few more times. She shuddered at the sensation of the thick object expanding her hole.

Pulling her tight pants up, she saw the circular shape of the butt plug through the brown pants. 'Oh my God! He'll have to be blind not to notice!'

Caroline carefully made her way to her cubicle and listened at the intake.

"We should walk by her desk," Geoff suggested.

"I have a girlfriend, buddy. Maybe YOU should walk by her desk. Go for it, Geoff! At least flirt a little." Bob poured himself a cup of coffee and left the breakroom to return to his office, giving his friend the opportunity to talk to the lovely blonde.

Hearing the conversation, Caroline spun around her cubicle looking for her purse. She quickly rummaged through it and pulled out the Asstrolube lubricant that she used to lubricate her plug a few minutes earlier. She put it right next to her computer keyboard.

She slid her desk chair to the side and leaned over her desk as if she was reading a document. From her position, not only would Geoff be able to see her purple G-string, but he would see the protuberance in her pants created by the plug...and the lubricant sitting on her desk.

'I can't get any more obvious than this!' she thought.

Geoff had to ask the receptionist where Caroline's cubicle was. As he approached, he could just make out her blonde hair sticking up over the shorter partition walls. He rounded the left side and hung his hand at the top of the divider in an effort to appear casual.

The small bottle of Asstrolube was immediately apparent. As it happens, Geoff had used the product once, but found it too thick to his liking. As quickly as he noticed the bottle of anal lube, he set his eyes on the sexy sight of Caroline's G-string. Then the plug caught his attention.

His poorly restrained gasp alerted Caroline he had indeed wandered in looking for her.

"Oh, hey, Geoff. What's up?" Caroline looked back at him, then turned back around as if she was not quite finished with what she was doing.

"Hi Caroline. Um, pardon my being so forward, I like those slacks, but they look funny in the back." Geoff's heart felt like it was about come out of chest after uttering such a daring comment.

Caroline turned her head and smiled. "There's nothing funny about what's going on in the back," then reached her hand around and pushed the butt plug in a little more.

She looked over at the Asstrolube and quickly reached for it, "whoops." She grabbed it and stashed it in her purse.

"Looks like you're having a great morning, Caroline!" He was beaming, his eyes wide with interest.