Awkward Anal

He let out a hushed satisfied sigh and twitched his cock in her still mouth. The taste was not as she expected, slightly meaty and sweet and not as unbearable as she imagined. A rock of her head made it glide back and forth making him twitch even more, his hands moved to her shoulders gently squeezing them like two bike handlebars.

Emma gulped as her head bobbed slowly, the increased suction seemed to draw him deeper into her mouth. "Right, bob, suck, bob, suck, keep it simple, you can get through this," she told herself. His cock seemed to dance as it slid back and forth skating on her palate. He groaned and gripped her shoulders tighter. Emma knew at least she was doing something right.

Physically it was more effort than she ever gave it credit for. Breathing wasn't that easy and her knee upon the sand itched. Apart from still being scared, and spooked by every rustle, emotionally she felt like a puppy trying to please it's owner.

"Oh fuck yes," he whispered, digging his nails into her shoulders as his breathing intensified. Suddenly his cock bounced up in two sharp twitches, he pushed his hips forward driving it to the back of her mouth. Emma Coughed and pulled back. His legs trembled and with a groan his pulsating cock sprayed her tonsils. It was disgusting, gooey, slimey like rancid egg white with a salty soapy taste. He pulled out and she spat what little she hadn't swallowed on the beach.

Her mother had long finished and had been watching the whole time. Emma didn't know if she should feel disgusted or thankful. The guys quickly made their excuses and left. Denise handed her daughter a can of coke from her handbag as they started their way to the taxi rank and a quiet journey home.

Emma lay in bed and despite 3 cans of Coke the taste still lingered. Perhaps it was all in her head. Every breath seemed to bring back the heady cum odour to remind her of what she did. As she lay trying to get her head around what had happened her mother was busy checking out her. hookup app as her husband snored his head off

500 messages. She quickly noticed a lot of them weren't even in the same country. Others could barely construct a sentence or were just creepy losers. Perhaps there was a diamond among the rough but she couldn't be arsed to wade through the shitpile. Her daughter deserved better than 30-year-old virgins whose only sexual experience was wanking into a crispy sock. It was no good, she needed her husband's help and couldn't get put it off much longer. Tomorrow was the day she'd break the news.

Emma set off after breakfast leaving her parents alone, this was it, Denise broke the bad news.

"What the fuck, fuck, fuck," he loudly replied shaking his head, " You've got to be fucking kidding me."

"It's anal or constant surgery, could even prove fatal. I hate the idea just as much but what can we do?"

"Shit, why haven't I heard of this? Isn't there a charity or something? Couldn't I just, you know give her a little pot of mine she could dip her finger in or something?"

"Doesn't work that way. Apparently only full anal sex works. No one knows why?"

"Christ she's uneasy sitting next to a guy on a bus never mind this."

Denise thought it wise not to break the news of last night, "I've been racking my brains out, how do we find a guy to do her?"

"She's a girl offering anal for fuck sake, they'll be queuing up."

"She's already going to pieces over this, do we really want some dickhead giving her a bad time and making it worse?"

"Well, I can't do her."

"I wasn't suggesting that," snapped Denise.

"I know, it's just a lot to get my head around. Have you looked online?"

"I looked on a hookup site, trust me you wouldn't let any of them near her. Don't you know anyone who'd be discrete and gentle?"

"What about her cousin? That's not incest if it's up there is it?"

"I've no idea but it would make family get-togethers awkward."

"And this is once a week? So we need a few backup guys just in case one's busy?"

"Let's concentrate on finding the first, don't you have a mate or something who owes you a favour?"

"I know a few lads, but come on, how am I supposed to ask them? What do we even want from this dick donor?"

"Just someone who isn't going to rip her rectum and can keep his mouth shut. You've watched enough porn, you know how anal can be with the wrong guy? "

"You seem to enjoy it though?"

"That's different, you know what your doing."

"What if a guy lay under a blanket with his dick through a hole and she rode him at her own pace?"

"I thought of that but riding a dick isn't as easy as you think. It's better to lie and take it."

"But how we supposed to know if he's any good? Not like we come with a licence or work record. Don't you girls talk about this stuff? Share notes?"

"Not my age group." Denise took a breath, the next question was going to be even harder, "I know it sounds horrid, but what if I test-drived potential candidates? You pick them and I, you know?"

"I'm not comfortable with that."

"Neither am I but what's the alternative? Do you want to hear her screaming when some inexperienced cunt ploughs her?"

He quietly shook his head and asked for time to think about it before leaving for work. Denise was pleased she got it off her chest but felt no far forward.

Emma returned late afternoon. Denise thought it would be a good idea to talk a little bit more. It had to be pushed or Emma would keep putting it off.

"About last night, I know it was wrong to put you in that position but."

Emma cut her off, "I know why you did it but I'd rather not talk about it."

"Fair enough, but there's still the issue of anal. I've had a word with your father. He's accepted it but there's still a few issues. Don't worry."

Emma was slightly relieved her father was ok, if ok was the right word. But she still faced the actual act itself. "But what guy? I don't want a random guy from a pub."

"I know, we're looking into other safer possibilities. Tell me, have you ever looked into anal before? Even just out of curiosity? "

Emma shook her head, "No, always thought it was something weirdos did."

"It's a healthy part of any relationship, weirdo or not. I've found a video I'd like to sit and watch with you."

Denise had searched long and hard for a non-threatening unscary sex act. It wasn't easy but she managed to find one. Emma wasn't particularly excited about watching with mother but at least she wasn't between her parents like that time in the cinema.

"It's only a few minutes long, just to give you an idea of what you can expect, " with that, she clicked play on her laptop.

A naked couple appeared on the screen, they looked late twenties and pretty ordinary. Denise began to narrate, "Now, they're nude but if you don't want to be that's ok. Lubrication is important but you can do that yourself, you don't have to have him finger you like that."

Emma cringed as she stared at a close-up of a finger disappearing, "I hope he doesn't bite his fingernails. Why is there no poop on his finger?

"It's called personal hygiene, it's important to be clean down there. Now here comes the penetration. Watch her face."

The lady gave a surprised expression, one you may expect from a mild shock-like sticking your foot into cold water or receiving a cheeky slap on the bum.

"See, that didn't look too bad did it?"

"She's probably used to it."

"You'll get used to it too, even first time, it's never as bad as you expect. Now that position is called pronebone, it's good but you might want to have a think about what's best for you. Now look, he's not going crazy, just slow steady strokes, he's not hurting her."

"But he could if he wanted?"

"That's why we're going to make sure you get the right guy. Notice how she's enjoying it. Lots of girls do. Don't be ashamed if you do."

Emma had to admit that the girl seemed to be getting pleasure from it, but that could be acting. He seemed to be happier than she was.

"Now watch he's going to cum any minute. Look a quick tremble and it's over. That doesn't look too scary, does it? "

"Bungee jumping doesn't look scary when other people do it either."

"I know your worried that's why I bought you this." She reached into her bag and pulled out a purple dildo. Apart from the unnatural colour, it was realistic looking with a real feel rubber coating. "Now men come in all sizes but trust me most are far smaller than they say. Don't worry about length, when it comes to anal, girth is the issue. This dildo is a pretty good copy of the slimmer guys."

"And you want me to masturbate with it up there?"

"Not now, just when you feel ready, just get used to being penetrated. If you want I can help later on."

Emma stared silently at the dildo, it looked narrower than a her average morning dump. Perhaps she could do this with the right guy.

Denise and her husband lay in bed that night. She wondered if Emma would be attempting the dildo but she had her doubts. Her husband whispered to her, "I don't think we've got a choice. If it means getting the right guy then I'm ok with you testing him out first."

"What about Peter, your mate's son? He seems ok."

"He did cross my mind, I know he's been about a bit but he's the polite type."

"Could he be persuaded to keep his mouth shut?"

"I've looked online, I can't see any boasts about past girls. I'm sure if we made it worth his while to keep quiet."

"Money?"

"Little backhander wouldn't hurt. Plus if he's any good put him on the regular list. I'm sure most guys would keep quiet for that."

Meanwhile, Emma was debating the dildo. She knew her mother was right, it would be wise to use it to build her confidence. But it would be a painful reminder of what was to come. If it hurt it would cause her to worry more. "I'll leave it for another," she thought as she switched off the light.

Two days passed before Peter was brought to the house. He had been briefed on the situation and left in no doubt about the need for secrecy. But despite a clear warning he'd go missing if so much as a rumour emerged, the chance to anally fuck two women including a virgin was too much to resist. Emma was not there, it was thought best to test him out in her absence.

It wasn't the first time he had met Denise. He never considered her a MILF, she never dressed or acted provocatively. Shoulder-length wavy auburn hair and hazel eyes with a body that said, "I watch what I eat but don't do the gym". She wasn't a head turner but neither was she a stomach churner.

At 25 he hadn't been with middle-aged women but he reckoned he'd clocked up enough experience to impress her. Denise had other ideas, "Before we go upstairs and I want to make one thing clear. I'm not looking to get fucked like a porn star. Prove me you can show restraint and we'll let you take Emma."

Peter gave his word and went alone with Denise upstairs. Her husband switched the TV on in the hope of putting it out of his mind. Denise began to unbutton her white blouse, Peter stepped forward to help but Denise pulled back.

"Listen, I'm sure you've got loads of foreplay skills but this isn't about giving me an orgasm or even a good time. All I want is you to show me you can move that dick in a way that's not going to hurt Emma, can you do that?"

Peter started to undress himself, "No problem, I understand that. If you don't mind me asking will you be needing me to lube you up?"

"I'm already prepped but I'd like you to show me how you'd test I was ready." With that, Denise lay her naked body on top of the bed.

Peter removed his last sock and climbed beside her, that freshly shaved pussy was so tempting but he knew he had a job to do. "Would you mind pulling your knees up for me?

Denise drew her legs up as she lay on her side giving him a clear view, "I know you're prepped but a little extra on my finger won't hurt." He touched his fingertip to her hole and asked her to push out. With that, he slowly and steadily pushed inside. His finger entered as easily as if he were pushing through soft butter "Are you ok? No pain?" They were the words Denise wanted to hear.

"So, What position do you think is best?" she asked.

"I'd recommend missionary, it's a relaxing position to be in or pronebone, it's more comfy but some girls say it's too domineering?"

"What about doggy? "

"It's ok with more experienced women."

"I'll go for prone bone then."

Denise lay on her stomach and clutched the pillow spreading her legs. She knew guys loved to fuck hard in that position so she was eager to see if he could resist the urge. He pushed her legs together telling her it would be easier, then straddled her sitting gently on her thighs.

Pulling her buttocks apart he rested the tip of his cock upon her hole, "I'm going to enter very slowly, can you keep pushing out for as long as you can? If there's any pain let me know."

Denise obeyed and felt him gradually sink into her. In truth, her experienced butthole had taken her husband's more impressive cock many times without issue. Nevertheless, she was impressed with his smooth technique that was a far cry from the clumsy fumblings of previous lovers.

Deep inside her, he asked if she was ok, then began to thrust. His movements were short and slow, perhaps not gliding more than 2 inches either way. She had grown to prefer longer more defined strokes but this was ideal for Emma. Under any other circumstance, she would have grabbed his hand and directed it onto her pussy.

Peter continued to pump into her occassional throwing in one or two longer strokes but never losing control. When his final thrusts approached, he gave fair warning before pushing deep one last time to deliver his seed. He wasn't the best lover she ever had but she felt he was just right for Emma.

Peter was told to come back in three days. That would hopefully give Emma time to prepare for her ordeal. Denise had noticed his penis was a bit bigger than Emma's dildo but he wasn't exactly a sphincter splitter. If he performed the same way then Denise was confident her daughter could handle it.

Emma returned home early evening. Her parents broke the news they had found a suitable man for her. Denise failed to mention how they determined his suitability other than to say they did considerable research. It was time for another little mother-daughter chat.

"Have you managed to give the dildo a go?" asked Denise.

"Not yet, I look at it then get cold feet."

"You're going to have to take the plunge sooner or later."

"I know, but, just you know, it's hard."

"Once you've had it in you you'll feel more confident to handle the real thing. If you want I can help. "Emma didn't answer but was visibly taken back, "Better me than your dad."

Reluctantly Emma agreed and they both headed to the privacy of her bedroom. The dildo was sitting unused on the bedside cabinet next to a tube of lubricant. Emma lifted her skirt and rolled her white panties off.

"You can keep your skirt on if you want, just roll it right up and lie on your side so I can sit on the edge of the bed. Pull your knees right up."

Denise squirted a blob of lube on her index fingertip, "Can you push out for me? just imagine that you're on the toilet."

"Why won't that push the dildo out?"

"It just opens the sphincter, trust me."

Denise watched as her daughter's ass puckered like a duck lip. "That's it, now I'm going to touch you. Just do the same thing." With that, she pressed gently, her daughter's hole clamped closed. Denise withdrew her finger.

Emma took a few sharp deep breaths and got ready for a second attempt. This time her mothers broke through, Emma squirmed as the finger slowly made its way up. Denise held it still a moment before gradually withdrawing, "That wasn't too bad, was it? Let's try a few more times to slacken that ring shall we?"

Denise lubed her finger and the procedure was repeated over and over until it slipped in effortlessly and her daughter's confidence grew. "I think you're ready to try the dildo, don't you?"

Emma nodded, "I'll try but go slow."

Denise began smearing lube over it, letting it build up thick near the tip. "Do exactly the same, I'll have to push a little harder but you can do it."

Emma immediately felt it's rounded head was thicker than her mother's finger. Of course it was, she knew it would be, but the pressure on her hole brought it home. She closed her eyes, scrunched up her face and pushed her rectum out. Denise pushed slowly but with purpose and watched as it vanished. She held it still a moment then released letting Emma's bum eject it.

"I'm going to give you some privacy now. Just practice penetration and see what position works best for you." With that, she smiled and left Emma to it."

The big day arrived. Emma was now confident she could take a penis inside her. But a man making love to her was a different matter. Sure she had orally pleased one, but this was a whole new level. Make love? Sex? Fuck? Medical probing? She couldn't decide how to refer to it.

It was after dark when he arrived. Denise thought it would be best to give Emma the choice of light on or off. The mood was sombre yet welcoming. Like a worried family taking a doctor to a sick relative. It was the first time Emma had seen Peter but he had saw a photo of her on his last visit.

Emma had to admit to himself he was good-looking with a boyband-type appearance, but all she could think of was getting through it. It was an awkward first meeting, he had been warned Emma wasn't talkative and he felt unsure what to say. Her parents steered clear of the big issue asking him innocuous questions on things of no matter. Emma could never understand that type of chat.

No one wanted to drag it out longer than need be. Denise took her daughter to her room for one final chat while the men discussed football but thought little of it.

"Don't worry, you're going to be ok. Just relax and it'll soon be over."

'Soon be over was the sort of thing you say before something terrible, but Emma appreciated the attempt, "Oh god, I can't believe this is about to happen."

"You'll be ok, trust me. Are you well-lubed?"

"Yes, did it just before he came."

"Wouldn't do any harm to put a little more. Get yourself ready and I'll send him up."

Emma sat alone, in a few minutes a man she barely knew would be inside of her. She'd had plenty of time to think about how to receive him, about how much skin to bare, and whether to leave the light on. Now on the brink, it was as if she had given none of it a second's thought.

She removed her skirt and panties hanging them over the chair. Her pink blouse could stay on, there was no need to expose her breasts. He knocked three times on the door then entered to find her lying under the covers.

"I suppose this is it?" she said quietly.

"Won't be too bad trust me. Believe it or not, most girls do this for fun."

"That's what mum says."

"I'll be as gentle as I can, Have you given any thought on position? missionary is good."

"Would pronebone be ok?

"Oh I'm not that bad looking, am I? I see you've got your blouse on, I'll keep my T-shirt on if it'll make you comfortable but the pants will have to come off."

Emma didn't want to look at his penis, but it was hard not to. Mother was right, that dildo practice would come in handy. It was a little bigger but she felt it was doable. She pulled her pillow down slightly and turned face down with her breasts resting upon it and gripped the corners.

"Your mother says you've prepared yourself down there, shall we make a start?"

"Could you turn the light off please?"

The room darkened but not into complete blackness. Peter climbed into bed and slid his hand on her bottom gently parting her buttocks. One finger dipped inside, he could tell she was ready. He didn't want to waste time in case she chickened out, she wouldn't be the first.