Caroline's Solution

"Yeah, you could say that. I'm a little behind, but not too backed up if you know what I mean." Caroline was enjoying the not-so-subtle innuendo.

"Well, like I always like to say, it all seems to work out in the end." Geoff grinned proudly at his ability to keep the inuendo going.

All the planning that went into her sexy wardrobe, and especially the stimulation she was receiving from the anal plug, had caused Caroline a near frenzied level of arousal. She had never felt so turned on, and here she was talking to a man who had picked up on all the anal-related clues she was giving. She was primed.

It was under these conditions that Caroline made the boldest statement of her entire life.

"Speaking of working out in the end, I know someone who needs a workout in her end."

She wore a sly smile as her sultry eyes looked down to Geoff's crotch.

Geoff paused with his mouth wide open, then looked down sheepishly and laughed. "Okay, okay. God damn it. Bob put you up to this, didn't he? Shit. I should have known." He shook his head and looked around the office again.

"I was hoping for a workout, not a prank," Caroline said as she turned around and stuck her butt out. "Push it in a little, will you please?"

Geoff's smile left his face. 'Holy Jesus, this is for real?' He simply could not believe this was happening.

Cautiously, he took three steps into the cubicle area and used two fingers to push the round end of the plug further into Caroline's ass.

"Ummm," she whispered quietly, "God, that feels good."

Caroline turned around and crossed her arms. "Well?"

Geoff had never been so flustered in all his life. Nor had he ever met a woman as attractive as Caroline, yet so comfortable flirting with him. His high level of discomfort got the better of him.

"Well..." He looked at his watch. I've got a conference call I have to prepare for. Uh...See you around."

Caroline watched dumbfounded as Geoff walked out of her cubicle and out of sight.

'Wow. That was going so well too! I must have come on too strong.' Caroline was perceptive enough to see exactly what had happened. In her sexually aroused, aggressive state, she did in fact, come on too strong and caught him completely off guard. She would have to adjust her approach a good deal. Her first experiment with being a forward woman failed to achieve the results she had hoped for.

The next day, Bob and Geoff were in the break room together.

"So, what happened? Did you ask her out? Flirt? Anything?"

"We talked for a few minutes, nothing special."

"Are you going to ask her out or what?" Bob's voice was raised a pitch. He sounded excited.

"I'm thinking about tomorrow."

"Good luck!"

Caroline heard most of their exchange and realized at that moment that her hunch was right. She had intimidated Geoff. She also realized that he could be trusted. He never mentioned the sexual banter or her wearing a plug to his friend.

Later that night and after a long masturbation session, she decided she needed to tell Geoff about her problem and not try to go about having a relationship in the usual manner. She also felt she needed to apologize. Her behavior was out of character for her and she felt like she was being a tease.

***

The next morning, as she was marking up a copy of an article, Caroline felt someone standing behind her. It was Geoff.

"Hey Caroline. Do you have a sec?"

She put her work down. "Sure thing. What's up?"

"Look, Caroline, I don't know if you're aware of your reputation around the office, but everyone thinks you're a religious fanatic. That's why I was more than a little surprised by your remarks, or suggestions or whatever it was you did the other day. You have to tell me now if this is some sort of joke or something."

She motioned Geoff further into her cubicle. Whispering, Caroline responded, "Okay, I'll tell you what this is all about. A few weeks ago, I happened to hear part of a conversation you had with Bob. Let's just say that after that conversation, I know what you like, sexually. And...I like that too. Why don't we go out and get something to eat tonight and talk it over?"

Geoff was flush. All the energy and effort he had put into his search for a woman who was cool with anal sex and here she just falls into his lap. Not even to mention a woman of Caroline's physical beauty.

"You mean about what I like to do with my girlfriends?" Geoff stammered.

"Yes. That's what I heard," she confirmed. "So, why don't we go out and talk about it. I'm not comfortable talking about this at work."

He nodded his approval. "Absolutely. Tonight. Yes." Geoff paused, but wanted to sound confident, so he followed up with, "Why don't we meet at Sandstone. Do you know where that is?"

"Yes, it's on Atwater Street, near the park." She knew the place. It was nice.

"Right. How about seven?" Caroline was carefully examining Geoff's clothing, his physique, sizing him up. 'He should do,' she thought.

"Seven it is. See you then." Geoff abruptly left Caroline's cubicle.

Caroline had worn the bigger plug again in order to keep herself ready, but it was too distracting to work in. She ducked into the restroom to take it out.

Removing her plug took a little doing. Her sphincter had tightened over the narrow, tapered part and didn't want to give it up. She quickly cleaned it in the sink while she still had the bathroom to herself, then wrapped it in toilet paper and shoved it deep into her purse.

The rest of the day was spent daydreaming about her date with Geoff that night. She seemed to be wearing a constant smile, not so much as a result of thinking about Geoff, but more of how sexually direct she had been with the man. She really wanted this and based upon all the conversations she had overheard over the past few weeks, Geoff seemed like he would make a good friend with benefits.

Caroline went straight home after work and took a shower. She used copious amounts of liquid soap to clean her ass. She marveled at how elastic her sphincter had become and knew she was ready. Whether it would happen tonight or not relied heavily on how Geoff presented himself at dinner.

Geoff arrived at Sandstone with five minutes to spare. As it was a Thursday night, he was able to easily get a table near the front window, so he could see Caroline arrive.

A woman like Caroline was once in a lifetime, and although he was by no means ready to marry, she was the type of girl men took seriously. She was definitely marriage material.

He saw her walk from across the street, her long legs showcased nicely by her white shorts, her bouncy breasts, braless in a red stretchy top. Her pitch-blonde hair she wore in a ponytail, made her impossible to miss.

He left the table to greet her at the door.

"Hey there!" she let Geoff kiss her on the cheek.

"So, you're for real. I'm very pleasantly surprised," Geoff said.

"Here I am. Very real."

"I already have a table." Geoff escorted Caroline to their table.

"So!" Geoff put his hands up and smiled.

"So!" Caroline laughed.

"How long have we worked in the same office now?" Geoff asked.

"It must be at least three years. I think you were there before I was hired."

"Yes, I think I would have remembered you if you were there before me." Geoff was trying to contain his smile but having a difficult time. There was still a part of him that didn't believe Caroline was serious.

The couple opened their menus.

"You said you wanted to discuss something about...my interests?" Geoff was dying to discover what the gorgeous blonde had to say.

"Yes, I do. Geoff, I don't know you very well, but there is a very private, very personal reason why I did what I did the other day. I feel I need to share this with you before we begin our evening."

Geoff could not believe this was happening to him. He rarely caught breaks like this in any area of his life, but especially not with women.

"I'm all ears Caroline. What you share will stay between you and me, you have my word."

"Good. The rumors you've heard about me are true. I am a very religious person. I don't date around, and I don't fool around. I've never dated anyone from work, so discretion is very important to me."

"Absolutely. Me too." Geoff nodded.

The waiter arrived at their table. "I'll be right with you."

Caroline waited for him to leave, then continued.

"I have a condition, sort of a physical disorder you could say, one that is relatively rare. This isn't easy for me, so here it goes," Caroline lowered her voice, "I can't have vaginal intercourse due to this condition. My genitalia is perfectly normal, but any physical contact with it causes me excruciating pain. This pain is so intense that it has prevented me from having vaginal sex with boyfriends and has made any future hope of marriage and having kids very bleak." She looked around to be sure no one could hear what she was saying.

"My last serious relationship ended because of this. He just couldn't commit to a relationship with me knowing that we may never be able to have sex."

Geoff sat with a stunned look on his face. He nodded for her to continue.

"It has been a curse. Anyway, a few weeks ago I was about to go into the breakroom when I accidently overheard part of your conversation with Bob about anal sex." (Caroline lied about where she overheard the conversation to avoid any potential problems with her purposely eavesdropping on her fellow employees through the air intake in the wall).

Geoff smiled. "Wow! I thought I was being extraordinarily cautious."

"It's okay, you thought the conversation was private, I shouldn't have listened. So, anyway, I decided to try, you know, stimulating myself anally."

Geoff could feel an erection coming on.

"It was awkward at first, but with some experimentation with a few new toys, I discovered that I could...satisfy myself anally."

The waiter returned to their table. Geoff coughed nervously, then ordered a bottle of Merlot. Once the waiter was gone, Geoff commented, "So that's where the plug comes in."

"Yes. I feel sexually liberated, Geoff. All of my orgasms up to a couple of weeks ago had been very painful. My condition has caused me a great deal of physical and emotional suffering and now, I have discovered a real alternative that has changed my life completely."

"Caroline, that is such an amazing story. It's not at all what I was expecting to hear."

Caroline thought Geoff looked shocked, but in a good way. There was a light in his eyes that gave her a good feeling.

"I miss having a romantic partner, and I've never had a boyfriend I could have sex with. But recently, my attitude about sex has completely changed. But there was a new problem; how do I go about dating men when I know going into the relationship that I can only have anal sex? I mean, sure I can give oral, and that was what carried my relationships along as long as they lasted, but what does that do for me?" She laughed.

Caroline felt a tremendous weight had been lifted from her. She was finally able to share what had been troubling her, and her solution with another person, and one who would understand the pleasure of what she had recently discovered.

Geoff coughed again, then cleared his throat. "Sorry, this conversation is a bit more... frank than I'm used to having on a first date. I'm good. Ah...here's the wine."

The waiter poured their wine and took their order. They both ordered a sliced steak salad.

"If you don't mind my asking, where do I fit into this? I mean, why me?" he asked.

"I'll be honest, you really weren't on my radar until I overheard the conversation. I don't date guys from work, period. But you gave me hope. You dispensed advice and I tested your advice, and it worked. I know it was unintentional, but I felt I knew you would understand and even appreciate my newly discovered pleasure better than some other guy I may have had something else in common with."

"I think I like where this is going." He smiled.

Caroline continued, "Well, think about it. I can ONLY have anal sex. How am I going to broach that subject with a prospective boyfriend? And if I could, what if they just aren't that into anal?"

"You're right. I know a lot of guys who are indifferent to anal sex or dislike it altogether. You have a valid point."

"I'm sorry, I know I'm taking a lot for granted. You may not be interested in me or my weird anatomical problems. I'm assuming a lot."

After several clarifying questions, and a discussion about the nature of vulvodynia, their meals arrived, and they began to eat their salads.

"Caroline, you are hands-down the most beautiful woman in the office. All the guys say as much. It would be like winning the lottery to be able to date you. And the fact that you like anal sex? Good Lord."

Geoff looked at his salad and shook his head.

"That makes me happy to hear you say that. I know this is an unusual conversation to have with someone you don't even really know."

"It is a breath of fresh air, Caroline. I couldn't make this up if I tried. Do you mind if I ask a few more questions? Personal questions?"

"Not at all." Caroline was nearly finished with her salad.

"Did you purposely wear that plug just for my sake?"

"Yes." Caroline smiled deviously.

"And bending down showing me your G-string?"

"Yep. It's completely out of character for me, but you have to understand what I have been going through. Try to imagine that every time you touched your penis you experienced an intense, excruciating pain. Try masturbating or having sex through this pain. Imagine this beginning when you were around 13 years old, around the beginning of puberty. Now fast forward. You're twenty-eight years old and the condition persists. What effect do you think such a condition would have on you physically? Emotionally? Socially?"

"I can't imagine, Caroline. Not even hypothetically." Geoff had a difficult time trying to be sympathetic sitting across from such a sexy, beautiful woman.

"That's what I've been going through and a few weeks ago, that all changed when I had my first anal orgasm, thanks largely to your words I overheard in the breakroom. It was a life-changing experience."

The waiter returned and suggested dessert. Caroline asked for the check.

"Hey now, let me get this Caroline," Geoff objected.

"I believe I asked you out, it's my treat. You can get the next one."

"Okay, I can do that! So..."

Caroline grinned like a mischievous schoolgirl.

"So...? Back to my place?" She extended her leg under the table and rubbed his thigh with her bare foot.

Geoff swallowed hard. "Uh, yeah! That would be amazing!"

"Why don't I ride with you. My townhouse is two blocks from here. I walked."

Caroline took Geoff's hand as they left the restaurant. She smiled to herself thinking back at her week thus far. So bold, so uncharacteristic of anything she had ever done. She felt a dark chapter in her life was ending and a new exciting one was about to begin.

Geoff parked the car and the two walked quickly to Caroline's townhouse.

"Nice place!" Geoff looked around the beautifully decorated first floor.

"Have a seat. I'm getting some wine."

Caroline returned with glasses and a bottle.

Geoff was sitting looking rather nervous on the couch in her living room.

"Do you mind?" She handed Geoff the corkscrew and bottle and sat back waiting for him to pour.

Caroline removed her sandals and was running her hands along her long legs. She sighed as she took the glass of shiraz from Geoff.

"Thank you."

"Here's to your new outlook," Geoff toasted.

Caroline laughed, "Here, here!"

Caroline moved closer to Geoff, legs touching. She decided it was now his time to lead. She had already spoke more frankly and used more graphic detail than she ever had before with any man. She felt a tremendous sense of relief at having shared all that she had with him. Now, as she sat with her legs tucked under her body, she angled herself toward him.

Geoff finished his wine quickly, Caroline followed suit. He poured them both another glass.

For as fast and loose as Caroline was acting, Geoff could tell this wasn't a one-night stand to her. That was what was so strange. She acted and spoke as if she had made a decision and that his being there seemingly about to have sex, anal sex, was just a foregone conclusion.

He didn't mind, especially not with a woman as attractive as Caroline, but he was having a difficult time adjusting to the reality of what was unfolding before him.

It was close to eight-thirty on a work night. He needed to move this along in order to have as much time with her as possible. Geoff made his move and leaned in for a kiss.

Caroline eagerly received him. She felt comfortable and relaxed. He was a little tight-lipped at first, undoubtedly nervous from having her share so much of her expectations with him, but he loosened up and after a few moments, she was enjoying a delicious, open-mouthed kiss. She thought of how nice it was to be able to kiss a man who knew her situation beforehand. Free from the anxiety that came with the knowledge that she would have to tell her lover that she couldn't have sex, usually at the most inopportune moment.

Geoff wasn't sure how to take her aggressive approach, he still didn't know what to expect, but the kiss was a good sign. Geoff was a good kisser and valued that in a woman. Caroline was becoming very aroused and he could sense this by her assertive tongue and writhing body.

"Mmm," she moaned as she felt his hand gently squeeze her breast. She was becoming wet, and she began to feel what it was like to expect a pleasurable sexual experience. For so many years, this would be the point where she would begin to feel disappointment. Distressed in the knowledge that she would not be able to see a passionate feeling to its sexual fruition. Now she had a legitimate outlet. One that she had already tried and tested.

Caroline felt she was squirming in her seat. She ached for Geoff to be deeply imbedded in her ass. She found herself hoping that his penis was neither too large nor too small. Her understanding of her body was nearly a science now. She knew what she could handle, something around seven inches, and on the thick side, and she also knew what she would feel less than satisfied with, something under five inches.

Geoff's kissing was more heated. He worked his way down to her neck as he caressed her arms. He reminded himself not go near her pussy. This thought caused him to pull back slightly and made him unsure of himself. At that moment Caroline stood up and declared, "I'm ready."

She reached down and took his hand escorting him up the carpeted staircase to her room.

Caroline had already thought about how this first experience would go. She wasn't expecting it to be romantic. She was still viewing anal sex as a graphic, even deviant act. She had accepted the fact that if she was going to have painless orgasms that they could only be anally achieved so she had been able to quiet any feelings of guilt about the subject.

Geoff and Caroline continued kissing on her bed, but Geoff, as turned on as he was, wasn't feeling the sort of passion that he normally would expect from an encounter with such a beautiful woman. It felt as though they needed to have sex before they could progress with any relationship. It was a strange twist, one that if someone else had presented to him, he would probably express admiration for their unique stroke of luck.

Geoff lifted her stretchy-tight, red shirt from her body. Her pert, full breasts sprung free and jiggled on her chest. 'Damn, she's perfect,' he thought. Caroline slid out of her shorts and slipped off her thong as she watched Geoff remove his clothes. She anxiously awaited the penis reveal.