A humorous story about the world’s most anal retentive couple, trying anal sex. Yes, that’s it. Fuck my asshole with your big dick. Give me that dick, deep in my ass!” Rebecca said,

“Darling, I had the most unusual of thoughts last night, while I was redoing my sock drawer. Just as I had re-rolled all the gray socks and arranged them according to their respective light wavelengths, I found myself daydreaming. Daydreaming in a sexual way, as a matter of fact.” said Charles. Charles was 33, enjoying a successful career as a CPA, drove a BMW that he washed on Fridays, Sundays, Tuesdays, and only if it needed it, Thursdays too. Everything in Charles’ life was immaculate and well organized.

“There you go again. Last year it was the same thing!” Rebecca huffed. Rebecca was a Nurse Anesthetist, 100 percent sure she was actually smarter than all the Anesthesiologists she worked with at the hospital, and angry and bitter about that, and quite a few other things too. Including Charles’ sex drive of late. The longstanding assumption of Saturday evening intercourse after both taking long showers, requiring him to shave, putting on robes, then having quick intercourse (with a condom of course, to avoid any kind of gooey liquidy mess) in the dark didn’t seem enough for him any more. Once, he put his tongue in her mouth while kissing, and she was still furious about that. How barbaric and disgusting, using the tongue during a kiss. Had she indeed married a sex maniac?

Still, she humored him. One of his previous endeavors had actually made life easier on her. A few years back, he came home with some far-fetched idea to shave the pubic area. But in a stroke of genius, Rebecca had Charles shave himself also, and the clean look pleased Rebecca. To the point of requiring Charles to remove all his body hair via laser. No more disgusting leg hair, pubic hair, or chest hair to have to see and feel. Sex on Saturday nights had almost become as sterile as Rebecca liked it, but she knew that Charles liked things orderly and immaculate as well.

“Very well, what is it this time, Charles?” Rebecca asked.

“Well Boopsie” (Boopsie is Charles’ nickname for Rebecca. Like most things, Rebecca detested this too, but it sounded fancy, so she tolerated it), “I was thinking about anal intercourse, actually. I’ve done some research; it can be quite sterile, with a few precautionary steps.”

“Anal intercourse? What’s gotten into you? That’s revolting and unclean!” Rebecca snapped. Secretly, she was a little intrigued, but her standard operating procedure was to demean and belittle every new idea at first. It’s what she was known for. That, and wanting things clean and orderly.

“Don’t jump to conclusions, darling. Remember how we both ended up enjoying the cleanliness of being always showered and shaven?” Charles attempted to reason. He was uneasy about bringing up such a big topic with Rebecca, but he knew it was worth a try. He resented not being allowed to ever touch her without a hot shower and shave first, but also knew that appealing to her sense of order and symmetry was his best chance. “I’ve read that with condoms plus adequate preparatory steps, it is very clean and sterile. Why, I bet if we tried it, I’d be happy for weeks!” Now Charles felt guilty, but he also knew that if he offered asking for sex less frequently, that may also tip the scales in his favor.

“Fine, I will listen. What have you discovered?”

“Well, there are dreadful people out there, who do all sorts of unclean things, such as not using condoms, not showering and shaving before hand, and you won’t believe this, some people even lick one another’s anal sphincters!” Charles said with dramatic flair. Actually, one time he saw Rebecca’s anal sphincter, and he caught himself staring. He continues to explain: “But I’ve read a few articles, even found a website called ‘SexStories’. I found a lot of very useful information. Although the consensus is that preparing with an enema is overkill, and even not recommended, we both know that it is the only truly clean way to proceed. I believe it’s wise to apply it over an hour in advance. Then, with ample lubrication, I believe that K-Y Jelly is the best choice, in spite of their foray into indecency with heated and scented versions, and gentle insertion, it is quite a pleasurable experience for both.

“Well, print out the articles, and of course, categorize and index them as well. As always, create a “pro’s” and “con’s” column. I’ll consider it.” Rebecca said. In fact, she was quite intrigued by the idea. She even felt a twitch in her private area, which rarely happened. She didn’t want to appear filthy, but in fact, she had once inserted a finger momentarily into her anus while showering, and had quite liked it. She stopped herself from proceeding further at the time, but now that Charles was bringing it up, perhaps she would consider it.

They spoke no more of it, and proceeded with their lives for a few days. At work, one of the more crass Anesthesiologists had always made repeated references to anal intercourse in the most vulgar of ways, but now Rebecca was more curious than ever. From his musings, she knew it could be quite pleasurable, although she also knew the Anesthesiologist probably didn’t care whether the female involved was enjoying it. She knew of all the health risks of course, being in the medical profession, but also knew that with some precautions plus her extra level of cleanliness, those could be mitigated. And she knew Charles was very excited too. She had seen him eagerly working on the documentation she had asked of him, and she saw the three-ring binder getting more and more filled with papers, colored dividers, and color coded tabs.

That evening, Charles presented her the fruits of his labor. It was a 3 inch thick 3 ring binder, filled with articles and documents, with a summary document up front with page references. He had done quite a good job, although she noticed on page 5 of the summary document, Charles had made a grammatical error. Nonetheless, she kept reading, and after a few hours was convinced. Obviously, the enema was a requirement, but Charles would have to be far far away during that application process. She came up with a plan of her own.

“Charles, dear, I’ve decided to agree to this. Here’s how we’ll do it. I’m afraid you’re going to have to be gone most of the day Saturday in anticipation of this. You’ll have to purchase two unscented enemas from the store, I recommend driving over to the South side of town to purchase them, it’s an hour each way, probably far enough. Return with them by about 10 in the morning, and then you will have to leave for the remainder of the day. I suggest going to work or something. At 4:45 p.m., I will apply these things in the spare bath at the other end of the house” (Rebecca felt dirty referring to the enemas) “and of course, you shall need to be far far away when this happens. I believe at approximately 6 p.m., I will have completely evacuated my bowels, at which point, of course, I will spray down the entire bathroom with bleach and leave it soaking in. You may return home at 8 p.m., at which point you will shower, shave everywhere, put on your robe, and we shall engage in this act.” Rebecca remembered that they normally eat dinner 1 hour before engaging in intercourse, but since this was an out of the ordinary event, they would need to modify their plans. “Perhaps you should purchase yourself your Tofurkey sandwich and eat at the office before coming home. I don’t want to complicate this event with any dining complications”.

“Very well, darling. I think this will be quite pleasing.” Charles was beside himself with arousal, even though it was Thursday. Thursday, he thought to himself. Then he remembered, the infernal lawn service had been at the office earlier that day, so this was going to be one of those Thursdays requiring a car wash. He would take care of that shortly, and that would clear his mind of all these primitive feelings he was having.

Saturday at 5:45 a.m., Charles’ alarm rang. He sprang out of bed, ready to get the day started. He went through is normal routine, including of course flossing his teeth using the plastic flossing device he special ordered from Sweden, shaving, buffing his nails, and of course, fully wiping down the bathroom after finishing. By 7:00, he was on the road to pick up the enemas and the condoms. He checked his log book, for the stores he had previously been to when having to purchase condoms. He had them indexed and had the spreadsheet in front of him, by date and location, so that he would never go to the same store twice. The next store to go to, where he previously had not been, was the Walgreens on South East 125th street, all the way on the other side of town. Charles chuckled to himself, at all the fools who simply go to the same store near their homes each time. It was going to be a 75 minute drive each way, and Charles happily embarked on his journey. He reminisced about the time that one employee had apparently transferred to a new store, so even with all his efforts, the same person actually saw him purchasing condoms at one store, then another.

Eventually Charles arrived, and to his dismay, several cars, more so than expected, were in the parking lot. Charles had planned for this, because he was accustomed to having to wait in the parking lot until there were few cars in the parking lot. Sometimes, he had to go in to the store and leave several times, to ensure that nobody was near him in line while purchasing.

This day was similar, except people kept coming and coming, so the store never emptied to Charles’ satisfaction. Finally, out of frustration, he decided “I’m going in. Damn them all to hell, if they see me buying KY jelly and condoms and enemas.” He huffily walked in, and having already researched the store, knew where to go. One thing caught him off guard, the first time in 3 years: The condoms were locked in a case, a sign of the much poorer neighborhood that the store was in. He was going to have to get a store clerk to help him, his worst nightmare. But no, it got worse. He walked to the next aisle where a clerk was stocking toothpaste, and she was an extremely attractive woman, a tall brunette, about his age, but clearly not of his social stature.

She’d worked there for years though, and knew the look people had when they needed condoms, adult incontinence diapers, and enemas. Each person had their own particular flavor of awkward embarrassment. “May I help you sir?” she asked, pretending she didn’t know what he was about to ask. She had to admit he was attractive, clearly out of place for this part of town. Well dressed, fit, nice looking. She’d do him, she thought to herself. And not just because he looks like he has money.

“Yes. Um. Well, um, I need something over in the next aisle.” Charles was mortified, but too much was at stake. Every bone in his body said to leave, but he had been planning this for so long, he needed the condoms and the enema, and the damn condoms were locked away.

“Oh, certainly.” He was standing right in the middle of the aisle, blocking her path somewhat, and she was in a mischievous mood. She decided to squeeze past him (which she had to), but also to brush her breasts against his shoulder (which she didn’t have to do).

Charles, being Charles, had no idea what had just happened. He wanted condoms out of the lock box, and wanted to shrivel up and disappear out of embarrassment. The very attractive store clerk was hitting on him, and he was completely oblivious. By now, they had walked to the aisle with the condoms, and were standing in front of the locked case with the condoms. Charles pointed at the ones he normally got, and stammered, “I need three of those boxes, please”.

By now, the clerk knew he was so nervous, that she could really tease him mercilessly. Even though he was cute. “No problem, those are nice. You look like you might need the Bigg Maxx ones though, are you sure these will be big enough?” She almost felt guilty, but the look on his face was priceless. “Also, I like the ribbed kind myself; the added stimulation really feels good inside me. Who’s the lucky girl?”

“Um… Uhh..” Charles was babbling, unable to get a word out.

“It’s OK, my lips are sealed. But these feel really good for the woman, trust me. Ok, tell you what, get the two boxes you are buying, but you HAVE to try these. I promise, the lucky lady will love these on you.” She winked, and leaned up to Charles’ ear, and whispered “Well, that is if you HAVE to use them. Personally, I’d take you, no condom. Your hot cum deep inside me would be way better.” she softly said, letting her lip touch his earlobe as she whispered. “My name is Tracie.”

Tracie had an interesting background. In another existence, she would have been a Doctor or Lawyer herself. She was brilliant, and had been a straight A student all through school. But even with the full ride scholarship she had earned, she had been forced by circumstance to drop out of college in her first semester to take care of her younger siblings, and realistically, her parents as well. She harbored a little resentment at the way her life had played out, and running into people from better lots in life always stirred up her thoughts of what might have been.

“I also need two fleet enemas please. And… uh.. K.Y. jelly, the plain kind” Charles blurted out clumsily. By now he knew that he was being propositioned, but he had no clue how to react. First, he was still anal-retentive and super uptight Charles, and this woman was up to his social standards. Plus, he was just clueless at what to say.

“Ohhh, interesting! Now you have me wondering about you though. This is an interesting combination. As long as you don’t ask for feathers next, we’ll be just fine”, Tracie quipped.

“No, no feathers.” Charles joked. And Tracie laughed. This was a first; Charles actually joked and flirted successfully.

“Good.” Tracie said. “Anything else I can do for you? Anything at all?”

“No, this was all I needed, thank you.” Charles said.

“Are you sure about that? Lone Ranger Masks? Handcuffs?” she joked.

“No, this was all I needed, thank you very much.”

“No blowjob in the storeroom right there, right now?” Tracie said, pointing to the storeroom door at the back of the store. “No cumming in my mouth? No having me swallow your hot cum? You’re sure you don’t need that?” Tracie said, and reached out and gave Charles a rub on the bulge in his pants. “Follow me.” she said, tugging him gently through his pants by his now erect penis..

Charles couldn’t believe what was happening, but he walked to the storeroom door and within moments of walking through, Tracie had pushed the door shut, and was undoing his belt buckle. How she did it so fast, he had no idea, but she had undone his belt, the button on his pants, his zipper, and tugged his pants down in a moment, and she took his cock deep into her mouth. She popped him out of her mouth momentarily to say, “Normally, I wouldn’t have to make it this fast.”, then she took his entire length into her mouth, then momentarily removed her mouth and continued, “But I’m on the clock.” then she proceeded to bob her head up and down Charles’s shaft. Now Charles wasn’t exactly the type who normally prolonged things, so in just a few moments, Charles was exploding deep inside Tracie’s mouth, who under the circumstances was happy that it happened so quickly. She was at work and on the clock. She played with his cum inside her mouth for a moment, and then happily swallowed, making a spectacle out of it for Charles’ benefit. Then she took a moment to lick his balls, then said, “Ok, back to work for me!” She wrote her phone number on one of the boxes of condoms, and said “Call me. We’ll do this right next time. I get off at 10 tonight, long shift for me today. And if your wife’s hot, maybe I’d lick her pussy too.”

Charles managed to finish paying for his goods, and left the store to head home, puzzled at what had just happened. Back to the real world, he had to get home, and then spend the day away from home, while Rebecca cleansed herself for anal intercourse.

Charles got home, and there was a note in the notebook on the kitchen counter, where Rebecca always left instructions. “Leave the items on the counter in the spare bathroom. Get home at 8 p.m., and when you get home, go to the shower and clean up.” Charles complied, then headed out. He would spend the rest of the day at work.

Rebecca waited for Charles to leave, then began planning her day. She had her weekly pedicure already planned, and decided she would eat an early lunch, knowing she would be cleansing herself later. She was feeling quite excited, in spite of everything. Then she heard the infernal sound of the yard man, mowing her lawn. She had noticed him a time or two, and noticed that he was always looking at her. She also thought that under all that infernal dirt, grime, and long hair, that he was probably quite attractive. She looked out the back window, and saw him mowing her back yard. He was sweaty and disgusting, she thought to herself, all outside in the heat and all those grass shavings everywhere. He happened to look up at the door just then, and did a double take. Rebecca realized that in her distraction, she had actually not tied the sash in her robe, and the yard man probably had seen full frontal nudity, her breasts and her private area.

Normally, she would have recoiled in horror, but something about this day was different. She looked straight at him, and flipped the robe off of her shoulders, letting it fall to the ground. She went to the door, opened it, and motioned him to come over. He came willingly, looking a bit puzzled. In three years of being her yard man, she had never done anything but rudely tell him what to do or what he had done wrong the last time he mowed. He came through the door, and to Rebecca, he smelled horrible. Yet for some reason, she sat back on her prized leather ottoman, opened her legs, and propped her heels up on the edge. The yard man, she though his name was Phil or Bill or something like that, she had never really cared, tore off his shirt and stepped out of his pants, and in a moment was mounting her like a sweaty beast. Rebecca had never allowed Charles, nor any man ever to have intercourse with her without showering and shaving first, yet here she was allowing a man-beast covered in sweat and mud and grass clippings and who smelled terrible to mount her, and without even a condom. Yet his arms were strong, and he had her under him, pinned, and he was thrusting his penis deep and hard into her, like some animal. And on top of everything, he didn’t stop. Charles normally would have been done within his usual 75 seconds, yet this beast of a yard man was thrusting in and out of her, and continued doing it for longer than any man had ever done before. She glanced at the clock at the 5 minute mark, and realized this man was still hard, and hadn’t flinched then fallen over asleep yet, and was giving no signs of that. He was holding her under him, and his penis was stimulating her in a way she had only felt once before. Suddenly, a wave of prickly tingles engulfed her entire body, and she experienced a massive eruption of pleasure, combined with a dizzy happy feeling. She was actually having an orgasm, her head spinning, lasting what seemed like an eternity, only ended by the feeling of a gushing heat inside her privates. She realized that for the first time since that despicable first time back in college, this man was ejaculating into her vagina. And yet it just felt good, even as she realized his semen was probably spilling out of her and onto the fabric of her ottoman. Revolting, yet for some reason, pleasurable too, from Rebecca’s perspective.

Eventually, both she and the beastly yard man came down from their high, and he got up. “Yes, very well. Don’t forget to finish the edging.” Rebecca said, as she returned to her form.

“No problem.” the yard man said, but before he left, he took the back of her head in his palms, and pulled her head to his, and he kissed her and stuck his tongue deep into her mouth. “I’ll take care of that edging for you. Just make sure you’re home alone this time every Saturday.” and with that, he walked out the door to finish his mowing.

Rebecca confused at what had just happened, got off her feet, locked the door, closed the blinds, and returned to reality. She was going to have to shower, a long hot shower, clean up the ottoman, and continue to prepare for the evening of decadence with Charles.

At 4:45, she inserted the enema, and having read and memorized the instructions, applied it accordingly. She had read enough that she knew it would be a bit uncomfortable, but that she would have a large bowel movement soon enough, at which point she would be well evacuated. She waited around and sure enough, had her bowel movement, followed by her cleaning frenzy to erase any evidence that any human had ever defecated in that bathroom.

She thought about Charles, and knew he would be home at 8, that he would be showering by 8:04, and that he would be coming through the bedroom door in his robe by 8:15, clean shaven, showered, and ready for their weekly intercourse. Except this time, they were going to try anal intercourse.

She had two glasses of wine while waiting, and lay in her bed. She had of course washed her robe from the morning in hot water, twice, and was wearing it. But again, she had it undone. She thought of what was about to happen, and about the dreadful yard man. She felt a tingle in her private area, and yet another first, she reached down and rubbed herself with her index finger. Then a second finger. And before she knew it, like an animal, she had three fingers actually inserted into her vagina. What ever had gotten into her? The alcohol made it a blur, but she did reach a second shuddering orgasm in a single day, more than in the past five years combined.

The next thing Rebecca knew, she was hearing noises from the shower. She must have dosed off, because Charles was in the shower, she looked over at the clock, and it was 8:14. Then the 4 flipped into a 5 and it was 8:15. She heard the clacking sound the shower made as the water turned off, and remembered that she needed to call the plumber to fix that. Then within a few moments, Charles came out of the bathroom, in his matching robe. He had in his hand a tube of K.Y. Jelly, and was apparently reading the instructions. “Are you ready, darling?” he asked.

“I suppose. Let’s get this over with.” she said. She was still pretending she had no interest in this, but in fact, had been thinking about it all day. She rolled over onto her stomach, letting a frustrated sounding sigh out as she did. Charles was surprised that her robe had been undone, but said nothing. He pulled the fabric up, exposing Rebecca’s bottom. It certainly was a nice bottom, and for the first time, Charles was facing the prospect of anal intercourse. He was quite hard, and he stepped out of his robe. He had put the condom onto his penis in the bathroom in advance, as he always did. Modesty first, he always said, and applying it in the bathroom avoided any of that business of Rebecca watching him put it on.

“That’s a different condom than normal, isn’t it Charles?” Rebecca noticed.

“Yes. Oddly enough, I ended up being forced to have a lengthy conversation regarding condoms with the Walgreen’s clerk. This one came highly recommended.” Charles replied. He decided this was not the time to discuss every aspect of his encounter with Tracie. And if Rebecca didn’t ask whether the clerk was a male or a female right now, he certainly wouldn’t mention it himself.

“Hmm.” Rebecca responded. That sounded very much unlike Charles. She imagined how amusing that must have been.

He opened the tube of K.Y. jelly, carefully placing the cap on the bedside table, liquid end up to avoid leaving any marks. He squeezed some K.Y. onto his erect penis, and immediately realized he was going to have to touch the K.Y. jelly with his hand. “Dash it all.” He thought to himself, as he generously applied the jelly to his condom covered penis. He ended up with a little too much, and nowhere to wipe off the excess. He certainly wasn’t going to soil his robe with the jelly, then he looked down at Rebecca’s bottom. “Darling, I think I should put some of this on you beforehand.” he said. He had never actually touched her sphincter before. He almost did once, by accident, but Rebecca had slapped his hand hard enough that he never did again.

“Very well.” Rebecca said, and Charles reached down and applied the remaining K.Y. jelly from his finger between Rebecca’s cheeks, getting to actually properly touch her anus for the first time ever.

Charles climbed on top of Rebecca, and positioned himself above her, his erect penis pressing against Rebecca’s anus. “Ready, darling?” he asked. Rebecca mumbled something, and Charles proceeded to press his penis against Rebecca’s anus. It was tight, very tight, and not a lot happened. Charles remembered reading somewhere, to do very short strokes, not to insert, but just to spread the lubricant around, and that seemed to work. Every miniscule stroke resulted in his penis going just the tiniest bit further, and Rebecca actually was also making circular wiggling motions to help. Charles was fascinated by the tightness, and between the two of them, it wasn’t long before Charles’ penis had actually penetrated Rebecca’s sphincter.

“Everything OK, darling?” he asked.

“Yes, dear. Keep going.”

“Very well.” Charles said, and continued. By this point, the part of Charles’ penis with the biggest circumference had already entered Rebecca’s anus, and Charles knew that the hardest part was over. He could now start doing longer thrusts into Rebecca’s anus, and Rebecca seemed to be complicit with this. Charles knew to himself, that he was officially having anal intercourse with Rebecca, and it felt very pleasurable. Almost animalistic, Charles thought to himself.

“How does it feel, darling?” he asked.

“Mmm.” Rebecca replied, almost sounding as if she was enjoying it.

“You like it then, my darling?” Charles said, still thrusting, but still mostly a gentle motion.

“You can go harder, dear.” Rebecca said.

“Like this, darling?” Charles said meekly, as he started thrusting more vigorously.

“Yes, just like that. Harder though. You may go a lot harder.”

“Like this darling?” Charles said again, this time moderately harder.

Rebecca was enjoying it, but also remembering the filthy yard man from earlier. “Much much harder, Charles. Much harder.”

Charles was trying, but had never actually had hard vigorous sex in his life. He just didn’t know how to give it to a girl.

“Fuck my god dam ass hard, you piece of shit. Give me that dick. Give it to me hard!” Rebecca blurted. Oh my god, she had never said anything like that in her entire life. She imagined the shocked look on Charles’ face, but believe it or not, he didn’t seem to mind.

“Oh, you want it hard in your ass, do you? You’re going to get it. I’m going to vigorously insert my penis into your anus, then I’m going to ejaculate inside your anal orifice!” Charles said. Then he realized, this is what those erotica articles he had read called talking dirty. Too late, almost comically, he added, “Slut!” But he meant well. And he actually did start really ramming his cock deep and hard into Rebecca’s ass.

“Yes, that’s it. Fuck my asshole with your big dick. Give me that dick, deep in my ass!” Rebecca said,

“Fuck this; I’m taking the condom off.” Charles said. He was proud that he used a profane word in the correct context, and he popped his cock out long enough to grasp the condom (with his bare fingers!) and pull it off. Doubly proud of his new found ability to have intercourse like a commoner, he also smeared the K.Y. jelly from the condom onto his bare penis, and then slipped his penis back onto Rebecca’s ass. “You want my bare cock in that ass, don’t you, you cock whore?” Charles said.

“God yes, give it to me. Give it to me hard then cum deep in my hot ass. Fill my hot ass your cum!” Rebecca said.

And with that, with images of Tracie the store clerk swallowing his cum, and Rebecca in turn with the thoughts of the yard man’s cum in her, they both came hard. Charles released a hot burst of his cum deep into Rebecca’s anus. Wait… into Rebecca’s hot ass, he thought to himself, then he flopped onto his side in exhaustion.

Rebecca was happy too. Even with the filth, and even as she reached for a handful of Kleenex to hold against her bottom to prevent any further mess, she was somehow, unimaginably, enjoying the feeling of hot cum dripping out of her body, in spite of knowing she and Charles would be scrubbing and bleaching for hours as a result of this. Her mind raced to how the yard man’s cum dripping out of her pussy and Charles’ cum oozing out of her ass at the same time would feel.

But next to the Kleenex box, was Charles’ box of condoms. Rebecca wondered to herself why there was a phone number for someone named Tracie written on the box. What exactly had happened during that condom conversation, she began to wonder. She remembered a particularly sexy brunette she had seen at Walgreen’s once, and the puzzling desire to kiss her that she had felt. What was coming over the two of them? And why was the “i” in Tracie dotted with a heart, anyway?