Awkward Anal

Authors note.

This story is about a mother helping her daughter with anal sex for medical reasons. I'm not a doctor so please seek medical advice if you or others have any of the symptoms. Remember not every tummy ache requires anal, no matter how sexy she is.

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Emma woke with a strange pain deep inside her. Each movement seemed to make it worse, even getting out of bed was painful. She felt the need to vacate her bowels and limped to the bathroom. What should have been a simple task was both impossible and agonising. Emma knew something was wrong. Had she inadvertently swallowed something that had stuck or was it cancer?

She was a reserved teen who was struggling with anxiety. Her recent 18th birthday a few days ago had passed largely unmarked, bar a quiet meal with family. Perhaps she had swallowed a fish bone, no, she just knew it was more serious.

Emma called her mother upstairs and explained the situation. She could see her daughter was in distress and helped her to the car. Given the area of pain, her father was given little information other than they needed to go to the hospital. After a lengthy wait, Emma found herself being gently prodded and questioned by a female doctor.

"Have you been able to go to the toilet before this morning?"

"I've not needed to for a few days. This morning was very painful and nothing came out."

"Have you inserted any foreign objects recently?"

The thought of such a thing had never entered her mind, she shook her head and said, "No." She felt the doctor didn't believe her.

Emma was sent for an x-ray and after another long wait recalled to the doctor's office. The pain was getting worse but at least the doctor would know she hadn't lost something up there.

"There's no foreign object but there is an issue. I'll need to insert a small camera if that's ok?"

Emma lay on her side with her skirt lifted. A cold blob of gel touched her anus followed by a wriggly feeling as the doctor fed the narrow flexible tube inside. She gritted her teeth as inch by inch it worked its way up. The doctor stared at a monitor for a moment before calling in her colleague. Emma knew that was never a good sign.

"I think we better get you into surgery. You appear to have a blockage caused by a digestive tract abnormality."

"Cancer?"

"No, no, but we'll have to release the pressure and get a specialist's opinion."

Emma woke a few hours later, the stabbing pain had gone only to be replaced with a scratchy itch. She was glad it was over so fast, she'd have hated to have dwelled on it for days. But what was it and why had it come on so fast?

After a short rest, she was taken to meet a consultant. He was an elderly man and was accompanied by two younger female doctors.

"First of all, apologize for keeping you in the dark but given the urgency, surgery had to come first. The good news is we've cleared the blockage but unfortunately, it's going to be a recurring issue."

He produced the X-ray and pointed to an area deep within her rectum. Emma didn't really know what she was looking at.

"Your condition is extremely rare and to be honest we don't know what causes it. There have only been a few cases worldwide. For some reason, this area by the rectosigmoid junction has the tendency to seal itself with a membrane."

"But it's never happened before."

"We know little about it. Untreated the build-up of faecal matter can cause it to tear with a lot of pain and there's always the high risk of poisoning due to retention."

"I can't keep having surgery, isn't there a pill or something?"

The consultant looked briefly at his colleagues, "There is one known effective preventive measure. We don't know how it works but it does. You need to have anal sex about once a week."

"Pardon?" replied Emma, "You've got to be kidding me?"

"It was discovered in Brazil 50 years ago after a man was sent to prison. He found it kept him flowing and his case drew attention. Doctors suggested it to other patients and it's had a 100% success rate."

"But can't I just stick a suppository up there or something?" Neither appealed but they sounded more logical than anal sex.

"Unfortunately not. There's been some limited research into other methods but it seems that only penis in rectum stimulation works. Do you have a partner?"

Emma felt she had walked into a tacky porn scenario. Any second he was going to whip his dick out to cure her. This can't be real. She looked at the other doctors silently begging for a second opinion. One answered her plea, but it wasn't the answer she sought.

"Tests with sex toys have shown to make the matter worse. All we know is there's something on penis skin or fresh semen that prevents tissue growth."

"So I can't even use a condom? Can't I just stick some up like you do with cows?"

"It needs to be fresh unfortunately and combined with movement."

Emma still couldn't believe what she was hearing, she'd definitely have to google this but perhaps keep it off Facebook.

"When would I have to start?"

"I'd give it two weeks for the surgery to heal then engage in full anal sex with your partner."

Emma never had a partner but didn't want to say. Her heart was already racing at the thought of anal sex. What was she going to tell her parents? She dreaded even asking for a ride let alone telling them this. They weren't bad parents, Emma just felt awkward asking for anything. Did she need to tell them? Where was she going to get a volunteer?

Her mother met her in the hotel lobby, she was relieved her daughter's operation only required day surgery but could detect she was stressed. Experience had taught her not to push and Emma would open up in time. Time wasn't a luxury Emma had yet she wanted to delay the conversation at least ten years. Dad? Well, there was no chance she could bring herself to tell him.

"Mum, could you pull over somewhere before we get home," she asked staring out of the window. Her mother spotted a quiet layby slipped in and switched off the engine.

Emma couldn't look at her, "Mum, I've got this weird rare condition where I keep sealing up inside." Her mother sighed gently but didn't interrupt.

"The consultant says there's no cure but I can prevent relapses," she paused for a few seconds, took a deep breath, "But I've got to have anal sex once a week."

Her mother sighed once more, "It's genetic, your grandmother had it too. I got lucky and I was hoping it would skip you too. We'll sort you out don't worry."

"Do we have to tell Dad?"

"No, we'll tell him it was an ulcer, he doesn't need to know. We'll have the house to ourselves after church tomorrow. We can discuss it properly then, don't worry."

Emma's mum, Denise, thought long and hard over the next two days. She had yet to see her daughter hold hands with a guy and knew her anxiety must be in overdrive. Sure more confident girls could just sign up to an app but not Emma. She knew from her own premarital days that most guys weren't exactly skilled at anal. The last thing Emma needed now was some inconsiderate jerk ploughing her ass.

There was only one logical course of action, she had to test out potential anal partners for her daughter until she found her confidence. But where? It wasn't like she could just put an ad in the church newsletter. There were of course plenty of sex apps but she had only heard bad things about the men who lurked there.

"No harm in looking," she thought to herself. She signed up to a popular hook-up app and put she had an 'interest in anal' in her profile complete with a borrowed photo. Should anyone suitable appear she could always rejoin with a more honest profile but for now she just wanted to test the waters and let it run for 24 hours.

But what of her husband? For him, anal was a special treat he was lucky to get once in a while. But now she was to offer her ass to all and sundry. It wasn't that she didn't enjoy anal, just she enjoyed vaginal a lot more and anal was a useful tool to get what she wanted. Ideally, she would like Emma to first experience anal in the safety of her own bed with the security of her parents close by. The poor girl was already eaten up by the fact she had to do it and the extra stress of being in a strange environment would be cruel to push upon her.

She'd have to discuss it with him but for now, Emma's anxiety was her priority. It was time for a mother-daughter chat. She headed upstairs and tapped on her daughter's bedroom door.

"Do you mind if we have a little chat?"

Emma put her book down. The 'birds and the bees' chat with your parents was never a comfortable one but she knew she was in for the advanced version.

"I guess you've got some concerns. Thought it a good idea to have a mother-daughter chat before your dad gets home. Don't worry about him I'll break the news to him."

"I'm not sure if I can go through with it mum. Not just the physical but, you know, being the type of girl who does anal."

"It's more common than you think, it's just not talked about so much. Truth is even if you didn't have this condition you'd probably do it sooner or later."

Emma paused a while, "Even you?"

Denise nodded, "Even me. And probably all your friends' mums too."

Emma wasn't totally convinced, it sounded like something you told a child about eating vegetables, "Eat your sprouts and you'll grow up to be a princess."

"Yeah, but it's one thing with your husband, this is completely different. I'd feel like a whore. I'm not sure I can just lie back and think of England."

"Do you mind if I ask if you've been intimate with a guy before?"

Emma shook her head.

"It's ok, nothing to be ashamed of. Not even a kiss under the stairs at a party?"

"Not the type of game my friends play Mum."

An idea formulated in Denise's mind but that could wait for now. "You know, anals not real sex. You'll still have your virginity, kinda like a little loophole."

Emma wasn't sure a future husband would be convinced and she was fully aware it was a 'little hole'.

"Is it going to hurt? Mum."

Denise knew it was a possibility, even with the best preparation. She didn't want to lie but had to balance it against persuading her daughter to bend over.

"Sometimes it can be a little uncomfortable, but you know, it can be enjoyable too. It's like any ride. You can have a smooth journey with lovely scenery or you can be on a rackety bus stuck behind a bike going past a scrap yard."

"Do you like it or just do it because Dad makes you?"

"They with the hole makes the rules, always remember that."

"But it's an exit, not an entrance."

"A door's a door regardless of the sign above it."

"When you say uncomfortable, what do you mean?"

"It's hard to describe, it's kinda like an internal squishy wobbly sensation. I'll be honest, it can wobble a bit too much but most of the time it's kinda nice."

"So it's still intimate?"

"That's not a bad thing you know? Even dancing could be considered intimate. Don't be ashamed if you find it pleasurable."

"How long will he be inside me?"

"How long is a piece of string? Some guys only last a few seconds others a fair while. There's no telling."

"It's the thought of a man enjoying me that's getting to me too. I know he'll be looking at me like I'm a backdoor whore."

"Unless you act like one he won't judge. Yes, he'll get a lot of pleasure from it but believe me he'll be grateful, not judgmental. You know, your dad wasn't my first back door experience, I'd been with a few others."

"Does he know?"

"No, never felt the need to tell him. That's the thing about sex, what you divulge is entirely up to you."

"So past boyfriends then?" said Emma, well aware of her single status.

"Not always, I was seduced my first time.

Used to love those romantic movies back then, still do I guess. Had a head full of starry romantic notions of being swept off my feet. Then one night, I was 18, I met this guy on a night out. Handsome, charming, read me like a book and knew exactly how to play me. I kinda got swept along with the whole thing and ended up going to his place. I knew I shouldn't but alcohol clouds inhibitions."

Emma was gobsmacked at her mother's irresponsibility, "Did you know what you were doing?"

"I was young but not totally naive. Told him I was keeping myself and he told me he wanted to take me down an alternate path. Dumb I know, but I just wanted him."

"You were in love?"

"I thought so at the time but in reality, I was just smitten by a player."

"Weren't you scared? I'd be terrified doing that?"

"Everyone's frightened the first time. I know it sounds kinda daft but you go into a sort of hypnotic state where you kinda surrender. I gave myself to him and he made love to me."

"Didn't it hurt?"

"I'll be honest, I could have done with a little more lube and a bit more loosening up but I wouldn't say it hurt, more a unique experience." Denise didn't want to give a thrust-by-thrust account.

"Did you regret it?"

"Felt pretty good at the time, left me with a satisfied feeling. So no I didn't regret it."

In reality, Denise was pissed off he gave her a false name and number and was never seen again.

The weekend soon arrived, and it was time the plan that was swirling around Denise's head was put into action. She knew what needed to be done and had mentally explored every possible avenue. This plan wasn't ideal, non were, but it was the best option.

She didn't want to warn Emma of her idea, she wouldn't come if she did. Instead, she simply invited her for a quiet meal and a drink in a nearby seaside town. It was a pub Denise had been in with her friends a few times but it was new to Emma. In truth it wasn't her favourite place, yes the food was good but it had a reputation as a pickup bar and guys trying their luck could be annoying.

Denise tried to take her daughter's mind off things with idle gossip as they worked their way through a plate of surf and turf. But at the back of her mind, she knew once the food was gone and the drinking started it would only be a matter of time before the men came. Emma wasn't ready for anal, but Denise knew just the thing to chip away at her anxiety.

As they sipped their post-meal drinks Denise subtly scoured the bar. It wasn't long before she spotted a guy bouncing from girl to girl unable to learn from rejection. She gave him that look that said don't bother approaching. It was a simple technique, catch their eye, eye them up and down like you were pricing up an antique, stopping your gaze momentary on their crotch before breaking their hearts with the subtlest of head shakes.

It was important to gently discourage unwanted attention. Making a scene was both unladylike and would scare off more desirable approaches. Her head would shake four times before two guys headed their way. A smile replaced the headshake.

"Not seen you two in here before, you on holiday?" asked one of them.

He was fairly good-looking, probably late 20s early 30s with short but styled hair. Denise liked a man with a proper haircut, she always considered a straight fringe to be a sign of criminality. Emma had once played the 'don't judge a book' card but once showed that 90% of men in police mug shots have the same haircut she had to agree.

"No don't live too far, just fancied a change from our local," replied Denise.

The other guy noticed both of their glasses were nearly empty, "Can we get you another?"

Denise quickly accepted before Emma had a chance to ruin things. He was a bit younger by a few years with a non-threatening appearance thanks to his boyish looks and mop of curly blonde hair. Emma was never a great socialiser so Denise knew she had to be the one to keep the guys interested.

It was a game she knew well, be attentive at first with a touch of I might go further conveyed with little more than the right tone or tiniest of flirtatious gesture. Emma restricted herself to the bare minimum as usual. Drink followed drink and with each Denise came a tad more flirty. Emma felt uncomfortable accepting the drinks but Denise knew they weren't free.

The time came for the guys to check if their investment had paid off or if it was money down the drain, "So how you girls getting home tonight?" asked the eldest.

Denise knew what he meant was, "Can we come with you?" She knew that was out of the question. "We're getting picked up later, but I could do with some fresh air."

"Fancy a walk along the promenade?" he suggested. Denise knew outside of the holiday season it would be very quiet at night there.

They walked about 3 minutes side by side before each girl felt an arm slide over their back in a hooking motion. Denise knew they were testing the waters and prayed Emma wouldn't break free. Emma wasn't exactly in her element but felt doing so would be more awkward especially since her mother hadn't shaken her guy off.

A flight of stone steps ran parallel to the sea wall and down to the beach. Denise felt herself being guided towards them. Experience had taught her when a guy leads you somewhere like that he wants a bit of fun. Away from the street lights in the shadows, he proved her right.

He turned to face her, took both of her hands in his and stepped close. She looked up at his face, tilted her head to the side and accepted his kiss. Emma wanted to scream, "What about dad?" but panicked and clammed up. Her guy, the younger blonde made his own move quickly swirling her around to face him. His arms wrapped around her, his hands on her pert posterior. A little squeeze and he pulled her close.

This was it, she was about to be kissed, god she wanted to shove and flee but how? Her own mother was right there wrestling lips. She closed her eyes as he leaned forward. His lips touched hers gently prising them apart. "It's only a kiss, I'm ok," she said to comfort herself as he softly sucked upon her lips. His tongue began to trace the inside of her lips occasionally briefly darting to her teeth. She didn't respond in kind. His hands remained firmly on her buttcheeks holding them like a little stool and as their bodies pressed she felt him grow.

Denise too had felt her man grow, but in her hand, as she fondled him. The night air was filled with the sound of a zipper heading south. He put his back to the wall as Denise lowered herself to sit on her knees. He reached down to unbuckle his belt and as the metal jangled Emma's guy turned to see what was going on.

Emma had not seen a cock before bar pictures. Now she looked on in horror as one sprang out inches from her mother's face. Innocent as she was, Emma knew exactly why her mother was squatting down. Was this another example of 'not real sex' one that doesn't count? She doubted her mother would be debating it with Dad.

Excited by what was seeing, the blonde guy thought he'd push his luck and with a flick of his thumb unloosened his jeans. Emma's heart thudded against her chest. Surely her mother would stop it now? She can't surely be expecting her to follow suit? As his hard cock appeared her mother said nothing but side nodded in its direction with a 'go on' motion before embracing her guy's cock between her lips.

Emma wanted to vomit. She knew her mother must be trying to make her more comfortable with guys but couldn't she have started off with letting her practice on a banana first? Her own guy was now looking at her expectantly. If she could not do this, how could she endure anal?

Nervously she stepped forward and lowered herself to one knee. She couldn't bare to look him in the eye, yet looking at his twitching tool was no easier. It was no thicker than the average size banana and a lot smaller. She tried telling herself to think of it as such, a banana, but she couldn't.

Her ran his fingers through her auburn hair and gently pushed her down. The tip touched her lips, "Jesus fuck," she thought as she reluctantly parted her lips and lowered her head. Slowly the head passed between her lips prising her mouth open scraping softly against her teeth until a good portion rested upon her tongue.