Thanks to Literotica member, Smoothed for his help with editing.

*****

Caroline Eriksson had the best cubicle on the entire floor at the office. It didn’t have windows, or a comfortable sofa, or nice plants. It wasn’t large and spacious or decorated any more nicely than the others. None of those reasons were why it was the best. It was best because of the gossip. The back of her cubicle was a shared wall that backed up to the breakroom. There was an air intake grate just under her desk, and another that matched it in the other side. From her place, she could hear even the quietest of conversations with only minimal effort.

She had been the first to hear of pregnancies, new romances, and failed marriages. She was the first to hear of her co-worker’s son, Jack, passing away, and she knew about her ex-boss, Chuck, and the affair he was having with the receptionist. She heard all the office gossip first-hand. Of course, Caroline never did anything with the information. She considered herself a good Christian and never spread rumors, or shared in any gossip, but it made her job of editing copy for a nationally circulated news magazine a little more interesting.

Caroline’s strong religious beliefs motivated her to serve those in need within her community. She tutored abused women at the shelter, taught Sunday school to first graders, and she regularly donated to the local homeless shelter. But despite her beliefs, and her commitment to service, she was a very lonely woman.

Caroline’s mother and father were born in Sweden and Caroline had a stereotypical, Swedish-blonde look to her: long, straight pure-blonde hair with a luxurious, natural sheen and bright, blue eyes; she had an almost angelic appearance. Her perfectly proportioned, tall and slender frame, made her stand out in a crowd. She had a rare and remarkable beauty. Yet with all of her natural gifts, Caroline still had trouble holding on to boyfriends.

“You don’t want to have sex, Caroline!” She could still hear Stephen’s cold, critical words as he broke off their two-month relationship. “You say you do, but you don’t. You have some serious issues.” On that night, he slammed the door to her townhouse and never called or texted her again. Despite her repeated explanation of her condition, he thought her problem was purely psychological.

There was nothing psychological about it. Caroline suffered from vulvodynia; a chronic condition that makes intercourse painful for women. For Caroline, this meant that she did not enjoy sex due to the pain that she experienced anytime a man tried to enter her vagina. No matter how hard she tried to deal with the discomfort, or what position she attempted to use during intercourse, she could not avoid the excruciating pain that accompanied penetration. As a result, her condition made it extremely difficult to achieve any sort of orgasm, even clitoral. Most would find it impossible to imagine a life without the ability to have an orgasm on a regular, or even semi-regular basis, but this was Caroline’s life. Her orgasms came at a price: an intense, burning, cutting, vaginal pain.

Caroline correctly attributed her difficulty in keeping long term relationships to her condition. It is extraordinarily difficult to find a man who did not want to have sex. At twenty-eight years old, Caroline has had a total of four lovers, all men whom she loved, and who could not handle a sexless relationship, even with such a beauty as Caroline.

On one particularly frustrating Monday morning at work, Caroline sat at her desk, depressed from a weekend of chocolate and romantic movies, listening to Bob Hesse and another employee whose voice she could not readily recognize talking in the break room.

“…then what happened?” Bob was asking questions of the other man.

“She said I was disgusting, that I was a pervert,” he answered quietly.

“A pervert. Man, that’s rough.” Bob’s voice grew even more quiet, making it difficult for Caroline to hear. “Just because you wanted to try something new?”

“It’s tough to find a woman…” The man’s sentence was cut short.

“Good morning, gentleman.” Caroline’s supervisor, Laura just walked into the break room.

“Hi Laura. How was your weekend?” Bob and the unknown man stopped their conversation mid-stream and shared pleasantries with Laura.

Caroline was dying to hear the rest of the conversation and listened intently for the sounds of Laura leaving the room.

The conversation resumed when the two men were alone.

“…it’s tough to find a woman…go on.” Bob encouraged.

“…who likes anal. You would think more women would be into it by now, you know?”

“Yeah, well, I don’t know. I’ve never had a girlfriend that was into anal, not that I’m not interested in it, I just don’t bring it up.” Bob shared. “I guess you just have to meet the right woman. Why is it so important to you, anyway? What’s wrong with just, you know, regular sex?” Bob asked.

“It’s just canlı bahis a preference. I love the feel. It’s tighter, feels warmer, it’s sexier to me. Damn. It’s late, I’ve got to get back to work.”

Caroline was disturbed by what she heard, partly because of her views on sodomy, but also because she didn’t know who the other man was in the breakroom. She left her cubicle and walked quickly around the corner to see if she could get a look at the man who was speaking with Bob.

It was too late. They had both disappeared into the sea of cubicles on the other side. She looked at the clock, it was just after ten-thirty.

That week, Caroline monitored the breakroom conversations, to see if she could hear the two men’s voices. She also looked more carefully at the dozens of men who worked in her office. Could she tell if a man was a sexual deviant by the look on his face? She tried to determine who was the “sodomite” as she scanned the breakroom during lunch, but without result. After four days of investigation, she was no closer to solving her mystery than she was when she first heard the lewd conversation on Monday.

Finally, on Friday, she heard Bob’s familiar laugh while working in her quiet cubicle and paid close attention to the conversation he was having with the still unknown man.

“Let me guess, still single, right?” Bob asked.

“I can’t exactly place an ad that says looking for a girlfriend who enjoys anal sex, can I?”

“Well, you could, but I shudder to think what you would get,” Bob joked.

Caroline recognized the man’s voice this time, it belonged to Geoff Jones, one of the vice presidents in marketing. She had talked with him a few times and recalls feeling uncomfortable around him. She didn’t think he was all that handsome either. As Caroline remembered, he was slightly shorter than she was, brown hair, average build, nothing special. Now she had a real reason to stay away from this guy.

Caroline closed her eyes tightly and shook her head to rid her mind of the thought of Geoff Jones wanting anal sex from some poor, desperate woman. She busied herself with work for the rest of the day. Thank god it was Friday.

***

At home, she realized that she had exactly nothing planned for the entire weekend. Her neat, well-decorated townhouse seemed quieter and lonelier on the weekends. She watched a movie and went to bed early for lack of anything else to do.

On Saturday morning, she ran her usual three miles, did some shopping, and looked on the Christian Singles website for profiles of potential suitors. She also cried three times, which was good for a Saturday. Sunday was almost a repeat of the day before, only she at least had church that morning. Caroline was still mourning the romantic loss of her last boyfriend who grew bored and frustrated with the lack of sex and the go-nowhere, extended make out sessions, which was the only sexual activity, save for the occasional blow job, that she could provide. Caroline couldn’t help it; she was forced to deal with the consequences of her condition. She went back to the online dating website on Sunday night. As she stared blankly at the screen scrolling through the litany of handsome and available Christian men, she inhaled deeply and gave a long sigh. It was not reasonable to expect a man to date her seriously and at the same time not want to have sex. Even if they abstained, there was no guarantee that her condition wouldn’t persist into their married life. How would they make love as a husband and wife? How would she have children?

***

Four long, dull days had passed at work and Caroline was relieved that she had heard nothing more about Geoff’s anal obsession. She was now forced to listen to the office slut, Chloe, complaining loudly about her boyfriend cheating on her to a friend she was talking to on the phone. Bob and Geoff came in as the woman ended the call. She must have immediately left the break room as the two friends began talking about sex again. It sounded as though Geoff was in the middle of giving Bob instructions.

“Preparation is everything. You can’t just shove it in her. It takes time to get her ready. You have to talk about it. Stretching her ass, a little at a time, and some vaginal stimulation is very helpful. It makes the difference between a ‘no’ and a ‘go’. Use a dildo, or a plug, something like that, well in advance of when you actually try to penetrate her.”

“Thank you, Dr. Geoff.” Bob chided his friend.

Caroline shuddered as she began to understand what the two crude men were talking about.

‘They’re talking about it again. Oh my god. That’s disgusting!’ Not wanting to miss out on any of the disturbing details, Caroline opened her side desk drawer and leaned down as if she were looking for something to get her ears closer to the air intake that connected to the breakroom.

“Have you ever had a girlfriend that was into it as much as you are? It sounds like you’re too particular. Most women aren’t bahis siteleri even going to admit they like that until you’ve been dating for a while, you know?” Bob was always amazed at how picky Geoff was with women, given the fact that he didn’t consider him that great a catch to begin with.

“Do you remember my telling you about Deanna? She had broken off her engagement and I dated her before she got back together with her fiancée.”

“Yes, I remember you saying something about her.” Bob took a sip of coffee and looked at his watch.

Caroline looked around briefly to make sure no one was watching her extended search in her drawer.

“Well, we had a very sexual relationship, and when she had her period, she still wanted sex, so we started doing it anally. Her period had come and gone, and she still wanted it in the ass every time…and we had sex several times per week for three months during the time we dated.” Geoff slid his chair back and crossed his arms.

“How did she cum? I don’t get it.” Bob became more curious after Geoff’s last claim.

“For the first few times, she rubbed herself, you know, then, she began having orgasms anally.”

“Damn, that’s hot.” Bob looked off to the side, imagining the situation.

“Hey, I’ve got to go. See you around.” Caroline heard the room become quiet before a woman in heels walked in and used the sink.

She thought briefly about telling someone, like Mary, her human resource officer, but realized that she would be revealing her secret source of gossip, and it may be discovered that she had been spying on her co-workers and secretly listening to their conversations. No, she had to keep this quiet. Besides, regardless of her moral objections to the content of their discussion, Bob and Geoff were under the impression that they were in a private setting when they had their conversations.

Caroline’s face was red from hearing such graphic, nasty details coming from the breakroom. She couldn’t focus on her work, so she decided she would take a walk down to the other side of the expansive office floor.

Caroline faked a smile and said hello to the several people she passed as she made her way through the cubicles to the marketing division. She would probably not have smiled at all had she seen the several men turn around to watch her strut down the hallway. Her long, muscular legs and toned, firm butt were the result of good genes and spending good money on a personal trainer, and the subject of many a male co-worker’s fantasy. She always wore tighter-fitting clothes to accentuate these features. She was single after all. Today, she wore a tight, dark grey business skirt and white button-down blouse.

Crossing the lounge area that separated the administration wing from the marketing wing, she slowed her pace as she walked by Geoff’s office. The door was open and the walls around the door were glass, allowing her to see inside. For some reason, she wanted to look at Geoff now that she knew his twisted secret.

‘There’s that foul man.’ Geoff was in his office module standing behind his desk, looking out the exterior window talking on his cell phone. He turned to face the room but did not notice Caroline glaring at him on the other side of the glass wall separating his office from the rest of the floor.

‘Who does he think he is? All he likes is anal sex? That’s disgusting. He’s probably an atheist too.’ Caroline lingered in the hallway, pretending to read from a company memo left on a vacant desk across from the door to Geoff’s office.

She was sizing him up. He wasn’t quite as short as she remembered, but she still had a couple of inches on him with her heels on. His dark, brown hair was combed back, no part. He dressed fairly well, not a slob, but not an office hipster either. As he turned around, she took in his face, relatively handsome, in proportion, but not someone you would go crazy about. Not someone she would look twice at if he were on the street. He was on the nicer side of average, she thought.

Caroline frowned at him pretending to read the memo and continued walking. ‘I don’t want him to think I’m interested. Yuck!’

***

After her session with her personal trainer, Caroline celebrated her Friday by returning home and enjoying an extra-long, hot shower. She used a natural sea sponge to scrub her smooth skin, as she always did, but that particular evening, she hung her sponge on the hook under the shower head and spread body wash on her hands to wash her bottom. This was unusual for her as she normally used a washcloth for that area. She hated to admit to herself that after hearing the conversation between Bob and that perverted Geoff that she was curious, but she was. She was very curious.

Caroline spread the slippery liquid soap all along her long, toned legs and buttocks, luxuriating in the sleek feel of her blemish-free, baby-soft skin. Arranging her hands on the sides of her ass, she separated one of her firm, round cheeks, bahis şirketleri having to grasp it closer to her body so it wouldn’t slip away from her under her soapy hands. Arching her back and causing her butt to jut upwards, she used her right middle finger to delicately spread soap up and down her crack, barely running her finger over her sphincter.

She hadn’t really paid too much attention to her butt before, other than giving it a thorough cleaning each day with a washcloth. She always viewed it as serving a utilitarian function, never erotic. Today was different. With all of Geoff’s disgusting talk about anal this, and ass that, she had anal sex on her mind, although it was buried deep down, underneath all her wholesome values, it was still there, motivating her current actions. Geoff’s words clearly had an effect upon her.

Now finished with her cursory cleaning, she used the tip of her middle finger to circle around her tight, pink virgin asshole, causing a small shudder to run down her spine. She never was so purposeful about touching her ass as she was in that moment. In a crazy impulse, she gently slid her finger inside her tight hole to her first knuckle. She felt slight resistance, then a loosening, then a tight clamp around the digit.

“Oooh!” The sensation surprised her.

“That’s okay, I guess,” Caroline observed aloud, keeping the tip of her finger inside her.

She wiggled her finger around a little, feeling the sides of her tight hole and the smooth tissue at the entrance to her rectum, then pushed more inside her, now up to her middle knuckle. She pulled her finger out and looked at it, not knowing what to expect, but cleanliness was foremost on her mind. Finding nothing but a less soapy finger, she inserted it again, this time faster, just to see what it was like doing so in one motion.

Her raised ass jiggled as she slid her middle finger back into her asshole.

“Oooh!”

Caroline was surprised at how stimulating it was, and not in an unpleasant way at all. She removed her finger again and washed it off, then applied more soap and inserted it into her asshole again. This time she made a few penetrations using the entire length of her middle finger. Slowly pushing in, and then up deeper into her rectum. She felt the warm, slippery texture, and was surprised to discover that the sensation was not only pleasant but gave her a mildly thrilling shiver.

Washing herself off again, she ended her shower, dried and dressed in a short, black T-shirt and her white, bedtime panties. She sat up on her bed brushing her long, straight blonde hair thinking about what Geoff had said that day:

“…she began having orgasms anally.”

After her experiment in the shower, she could imagine that it might just be possible. Her ass was sensitive, and she felt sexually stimulated in a deep way, almost what she had read about when she was in college about having a G-spot orgasm, which she had never experienced.

Caroline hadn’t enjoyed an orgasm in several months. She was tired of the whole process she had to go through to achieve one. Normally, she would need to take a few ibuprofen tablets several minutes before trying, and she used a little lidocaine to numb her vaginal tissue all the way up to the base of her clit. Often times the lidocaine numbed her too much and made the effort more labored than it should be. The result was always the same: her orgasm was barely worth the pain and discomfort she experienced trying to achieve it.

All the talk she heard from Bob and Geoff had put the thought of an anal orgasm into her head, and she was having a difficult time ignoring the thoughts of having a climax. After her continual failure to remove the thought from her mind, she suddenly got a burst of sexual energy. A wave of arousal rushed over her and made her mind race with sexual thoughts.

She was going to try it.

Now almost delirious with excitement, she began to think about the logistics of anal penetration. ‘I will need a lubricant for sure…Vaseline, I have some Vaseline, and I have baby oil.’

Becoming giddy with anticipation, Caroline got up out of bed and grabbed the lubricants from her bathroom cabinet.

‘A little wine wouldn’t hurt!’

She hurried to the kitchen and opened a bottle of wine, carrying it back to her bedroom with a stemless wineglass.

Pouring herself a full glass of the shiraz, she peeled her duvet back to her sheets and lay down. Caroline inhaled deeply, then took a few, large sips of the strong, red wine.

As she reached for the Vaseline, she realized that this could be a messy process, so she leapt up from her bed and grabbed a box of tissues. While in the bathroom, she noticed her round brush laying on the vanity. She always thought the long, solid handle looked phallic, and it was, quite phallic; perfectly smooth, polished, varnished wood…she grabbed it too.

Caroline settled onto her bed and spread her long legs wide. She had to lean back more than what she was used to in order to access her ass as she lay down. Dabbing some Vaseline from the plastic jar, she lightly smashed the gel into her clenched sphincter, then spread it around the entrance.