Roadside Assistance 13

He sat in his car, pulled off to the side of the highway, watching the headlights approach through the darkness.

They came closer, closer, before drawing level and speeding past.

He sighed, and checked the rearview mirror, again.

She was still there, parked about 30 meters behind him.

He checked the time on his phone. There were some more messages from his friends, telling him to hurry up.

He started to scroll through his phone and then stopped, remembering he was trying to conserve his battery. He wasn't sure how much longer he would have to wait.

But he'd promised he would stay, so that's what he would do.

Another set of headlights came over the crest in the far distance and approached. He couldn't help but get his hopes up with each and every one.

This one passed them too.

He sighed again.

But then - a screech of tyres. His head snapped around.

The car that had flown past them was doing a u-turn and coming back.

It pulled up behind the car he'd been waiting with.

They all got out almost simultaneously.

A woman got out from the car that had just arrived and approached the younger woman from the middle car. He hung back.

'Lily, I came as soon as I could. What happened to the car?' the woman asked.

'I don't know, Mom. It just switched off. I had to pull over.'

'Why were you coming back so soon? I thought you were going to stay out there all weekend with Jackson?'

She looked down.

'We broke up.'

'Oh, I'm sorry honey,' she moved in and gave her a hug.

'This is the guy that was waiting with you?'

Lily glanced over.

'Yep.'

Lily's mom walked over.

'Hi,' she said. 'I'm Jenny, Lily's mom. You waited here all this time with her?'

He nodded his head.

He shifted his position to get out of the glare of the headlights Jenny had left on. He got a better look at her. She looked about 40, was wearing exercise tights and a thin sweater. Her long, brown hair was tied back in a ponytail.

'Sorry I took so long to get here.' She paused. 'You don't know how much it means to me that you waited with Lily. When she called me and said where she was, I knew I'd take a few hours to get here and the thought of her being stranded out here all alone would've been terrifying.'

He smiled.

'Not a problem at all. When I saw her pull over, I figured no one would do that at this time of night unless there was a problem, so I stopped too. I had a quick look at her car but I think whatever is wrong with it is well above my skills I'm afraid.'

'That's ok, we'll have to get it towed. Thankyou so much again for waiting, it must've ruined your entire evening, having to wait for me to show up.'

'It's ok, really.'

'Did you have anything planned tonight that you missed out on because of us? I feel so bad.'

'Don't worry, really. I was just heading into the city to catch up with some friends. One of my friends is getting married soon.'

Her eyes widened.

'A bachelor party? We made you miss out on a bachelor party? Oh, I'm so sorry.'

'It's ok. I was going to stay in the city all weekend so I'll still have tomorrow to hang out with them.'

Jenny turned to Lily, who had hung back.

'Lily, come over here.'

Lily walked over, her arms drawn across her body. She was young, maybe 20 or so. Her hair was to her shoulders, dyed pink, cut in a jagged fashion. She was short, shorter than her Mom, and petite.

Jenny turned back.

'Sorry, I didn't even ask for your name?' she said.

'I'm Matt,' he replied.

'Lily, did Matt explain to you he was missing a bachelor party to wait out here with you?'

Lily shook her head.

'I feel we need to make it up to you somehow. Lily,' Jenny said sharply, 'have even said thankyou?'

'Thankyou,' Lily said quietly, not looking up.

Jenny shook her head. She paused, thinking.

'Matt, do you have a girlfriend?'

He blushed.

'No, no I don't.'

Jenny leant into Lily's ear and whispered something.

'Mom!' Lily said. 'I'm not doing that!'

Jenny raised her eyebrows.

'Matt stayed out here for hours to make sure you were safe, and he's probably missed out on all kinds of things at the bachelor party. I think it's the least you could do.'

Matt held his hands up in front of him.

'You really don't need to do anything for me,' he protested.

'Please,' Jenny said, 'just something small to show our appreciation.'

She looked at Lily and raised her eyebrows.

'Why don't you do it?' Lily said.

Jenny stepped in close to her.

'Because he's 22,' she said quietly. 'I think he'd prefer it coming from someone your age rather than mine.'

Lily looked away.

'Fine,' she said.

She reached under her shirt and unhooked her bra.

Matt's eyes widened.

Lily started to pull up her shirt. He could see the creamy, pale skin of her flat stomach.

Then suddenly, she stopped.

'I can't do it, Mom.'

She dropped her shirt back down.

'I can't do it,' she repeated.

Jenny nodded her head.

'It's ok, dear. Go and wait for me in the car.'

Lily walked back to the car, bra in hand.

Jenny turned to Matt.

'Sorry about that. She's just broken up with her boyfriend. I was hoping she might give you a bit of a treat to say thankyou.'

'That's ok. You really don't have to do anything. I'm just glad she's safe now.'

Matt started to turn towards his car.

'Before you go,' Jenny said, pausing, 'I know it might not be the same as if I was a hot young 20 year old like Lily, but I could show you something if you wanted.' She blushed. 'I understand if you don't want to. I'm not as young as I used to be,' she blurted out.

He turned back.

'Don't be ridiculous, I think you're super-hot,' he said. 'But I don't want you to feel like you have to do anything.'

She beamed.

'No, I want to. I really want to.'

She quickly pulled off her sweater and unhooked her bra, freeing her big, full, breasts.

His mouth was agape.

She smiled at his reaction.

She stepped in closer to him.

'You can touch them if you want to,' she said, and pressed out her chest towards him. He began to reach out, then hesitated.

'Don't worry,' she said, 'I don't have a husband who's going to hunt you down if you feel me up a little. Lily's father left years ago.'

She bit her lip and gave her tits a wiggle to entice him.

'Go on.'

He slowly reached out and placed a hand on each breast. Her skin was soft and warm.

She drew in a breath as he ran his fingers over her hard nipples. He massaged her gently, covering the full curve of each breast.

That feels so good, she thought.

He began to pull his hands away.

'You can keep going,' she said.

'Are you sure?'

She nodded.

She noticed that, while he was feeling her tits, he kept glancing downwards, towards the band of her exercise tights, and below.

'Is there something else you would like to see?' she said.

His head snapped back up.

'Sorry, no, nothing,' he said.

'It's ok, Matt,' she said, looking over each shoulder quickly, as if anyone might be around. 'I must admit I'm a bit flattered you might want to see more of me. Now, I wouldn't normally get stark naked for a complete stranger on the side of the highway, but...'

She turned away from him and bent over, hooking her fingers into the band of tights.

'After what you did for Lily, if you want to see my pussy too, then you get to see my pussy,' she said, and she pulled her tights and underwear down to her ankles in one motion.

She reached back and spread herself apart so he would have a good view of her. She wondered if he could make out the glint of wetness that she could feel forming between her legs.

He could make out the light pink of her pussy lips. Her ass had a nice round curve to it.

She turned around and stepped back in to him. She took both his hands and placed one back on her breasts, and one between her legs.

'Is that what you wanted to see? she asked.

He nodded slowly.

She reached down and ran her hand along the outer of his pants. She felt the outline of his rapidly hardening cock.

She leaned in to his ear.

'This is going a bit further than I'd originally planned,' she paused, 'but I'd really like to suck your cock.'

He breathed heavily.

'Ok,' he said.

'Come around here,' she said, and manoeuvred them around to side of the car, on the other side to the road.

They were out of the glare of the headlights of Jenny's car.

She knelt down in the grass in front of him and tugged on his pants, bringing them down to his ankles.

His cock sprang forth in front of her face. She felt a strong rush between her legs when she saw how big he was. She gripped his shaft in her hand and felt his thickness.

She began to lick on the underside of the head of his cock. Long, slow, licks. He groaned.

She opened wide and took him in her mouth. She sucked the head of his cock, and then went down as deep as she could, till she could feel him touch the back of her throat. She pulled back and then assumed a steady motion, greedily sucking him back and forth.

She was in such a trance that she didn't hear the car door open and close, or the footsteps approach. She was startled by a nudge on her shoulder. She looked over.

It was Lily, completely naked, kneeling down beside her.

'Lily?'

She had a look of fierce determination in her eye.

'I'm the one he stayed out here with, I should be the one giving him a blowjob,' she said, and reached out and took his shaft, tilting it towards her own mouth.

Jenny couldn't help but feel a twinge of disappointment as Lily started guzzling him instead.

Matt couldn't take his eyes off Lily's naked body. Her tits were smaller than her mother's, but her pink nipples looked incredible against her pale skin.

Lily reached around and placed her hands on his ass, and began pressing him further into her mouth as she bobbed her head on him.

He could feel the tightness around the head of his cock and knew she was forcing him down her throat. She was spluttering each time she deep-throated him but didn't stop or pause for a second.

Eventually, she brought her mouth off him, and strands of saliva connected her lips to his cock until she wiped them away.

She got up and took a breath. She led Matt a few steps away and faced him towards the car. Jenny looked on quizzically.

Lily then stepped in between Matt and the car and bent forwards on an angle. She leant on the car door with one hand and with the other, reached back and guided his cock to her pussy.

'Lily?' Jenny said.

Lily looked over, her pink hair a mess all over face.

'You said we should show that we appreciated what he had done, didn't you?'

'Well,' Jenny said, pausing, realising maybe it wasn't that she thought Lily was going too far, but that she was jealous it wasn't her pussy he was about to fuck. 'Go for it.'

Lily began to press her wet pussy back against his cock, but then stopped. She pulled away from him.

'Is everything ok?' Jenny asked.

'I just had a thought,' Lily said. 'Of something extra special I could do for Matt.'

She began plunging two of her fingers deep inside her pussy, again and again, lathering them with her juices.

'I think virginity is one of the most special gifts that a woman can give,' she said.

Jenny raised her eyebrows, she was pretty certain Lily wasn't a virgin.

Lily took her fingers out of her pussy and looked over her shoulder back towards Matt.

'Now, I'm not a virgin in my pussy anymore, but I am still a virgin here,' she said, and slowly started running her slick fingers around the entrance to her asshole.

'I want to give you my anal virginity, Matt,' she said, and guided his cock to so he rested against her ass. 'As your reward,' she said, gritting her teeth and pressing back against him.

The first few thrusts she could barely get any of his thick shaft inside her asshole, but slowly she worked his cock head inside.

She paused for a second and turned to her mother.

'Jackson was always pressuring me to try anal,' she said. 'It's part of the reason why we broke up. Imagine if he could see me now, a stranger fucking my ass on the side of the highway.'

And with that, she took a deep breath and sank back against him again, this time taking him halfway inside her. He was still, letting her do the work.

The feeling of fullness in her ass was something she could've never imagined. She wanted him as deep as he could go.

Each time that she took him a bit further it was a little uncomfortable at first, but she quickly got used to it. She took him in as far as she could. She reached back and felt his shaft, he still had about another inch before he was fully buried inside her. But she didn't feel like she had another millimeter of space inside her ass that she could fit of him, let alone another whole inch.

She was determined though, and began to press back against with more and more force each time, willing his cock deeper and deeper.

Eventually, she felt her ass cheeks press against hips and knew she'd made it.

His entire cock was inside her ass.

She felt an immense satisfaction, along with a heat between her legs. She'd been so focused on taking him deep she hadn't realised how much wetter she had gotten.

Without taking him out of her, she moved her feet from where they were spread out, until they were together. She pressed her knees and thighs together as well, clenching her asshole around him.

'Does that feel tighter, Matt?'

He could barely speak.

'God, yes,' he rasped.

'Good. Pound me, Matt,' she said. 'Pound me hard, please.'

He took a hold of her hips and started to move in and out of her ass. Every time he pulled back to her entrance, he felt like her asshole sucked itself in tight again, so much so that he had to apply force to penetrate her again each time. He worked up to a fast rhythm, slamming her deeply with each thrust. She moaned each time he filled her up.

Her legs were pressed tightly together, but she reached down and jammed a finger in between and started rubbing her clit.

It wasn't long before she could feel an orgasm swelling.

He was driving himself into her with such force that it was shaking her tiny body each time his hips slammed into her ass.

She rubbed her clit faster. Her breath was getting short and raggedy.

The orgasm flowed through her. He continued to hammer her ass as her body quivered. Juices leaked down the inside of her thighs.

She reached back and held out her hand against him.

'I don't think,' she paused, still catching her breath, 'my ass can take anymore, sorry.'

She pulled away from him, and immediately missed the feeling of fullness in her asshole. She turned and dropped to her knees and, without skipping a beat, started deep-throating him again.

Jenny came over and placed her hand on Lily's shoulder.

Without taking him out of her mouth, Lily turned her head.

'That was incredible, Lily,' Jenny said. 'Do you want to maybe have a rest for a minute and I can show him some appreciation, too?'

Lily let him drop out of her mouth. She was still breathing hard.

'Ok,' she said. 'Sure.'

Jenny stepped in to Matt and grasped his shaft.

'I may not be able to use my ass like these young girls can,' she said, 'but I like to think I've got a few tricks up my sleeve that they don't. Wait here for one second.'

She rushed down to her car and grabbed a picnic blanket.

When she came back, Lily was on her knees again slobbering over his cock.

'Lily!' she said. 'It's my turn!'

'Sorry,' Lily said, grinning, moving away.

Jenny laid out the blanket on the grass.

'Lie down,' she said to Matt.

He lay down and she straddled him, lowering herself down so his cock just parted her pussy lips.

She took his hands and placed one on each of her breasts. She leant in to his ear.

'These young girls don't know how to be on top of a guy. I want to show you what an experienced woman can do.'

She was super wet from watching him slam Lily's ass. She lowered herself further and gasped as his cock spread her wide.

She lifted herself and then sank down again.

She groaned.

She started grinding her hips as she moved up and down. She could tell by his face that he liked the rhythm.

She moved his hands to her ass, then leant back and started running her hands through her hair, then over her breasts and body, really trying to put on a show for him.

His cock was hitting just the right place inside her. She felt a special kind of orgasm building.

She leant in to him.

'Your cock is so perfect, Matt.' She bit her lip. 'This is a little embarrassing, but the way you're fucking me I'm going to have a very,' she paused, 'messy orgasm. I've never had this kind of orgasm before with a guy before, only ever with my toys. But your cock is so big and so strong inside me that I can feel it coming.'

'Ok,' he said.

'It will get really messy though, so if you'd rather that I didn't then I'm happy to suck you off or try something else?'

He shook his head.

'I want you to cum, Jenny.'

She kissed him, passionately.

She sat back up and resumed her rhythm, grinding her hips as she rode him. She got faster and faster, could feel the release building inside her. His cock hit the special place deep inside her and she couldn't take the pressure any longer.

She lifted herself off his cock and cried out in orgasm as a flood of juices streamed out of her pussy. It covered his cock and balls, and some of his stomach. She hovered over him, panting.

She reached down and fumbled with his cock, now slippery with her cum. As she was attempting to plunge him back inside her sopping pussy, there was a moment - a brief moment - where the head of his cock grazed against her asshole.

It was like an electric charge ran through her entire body, her nipples, her clit.

She leant back in to him.

'I've got a secret, Matt,' she whispered. 'I'm actually an anal virgin too. I never thought I would've even wanted to try it, but watching the way you handled my daughter's ass makes me want it so badly.'

She took his shaft out of her pussy and repositioned him so he was at the entrance to her ass.

'I'm not sure if I'm even going to be able to fit you inside but I really want to try for you.'

She wiggled her hips a little, teasing the head of his cock with her asshole.

'Go on,' she said. 'Take it. Take my anal virginity.'

He took a hold of her hips and gently thrust upwards, penetrating her ass with the head of his cock.

She forgot how to breath for a moment. The feeling was the most intense she had ever experienced.

When she had cum, she had gushed so much fluid that some had run down between her legs and coated her asshole, so she was already lubricated and ready for him.

He pulled back and thrust again, going a little deeper.

She closed her eyes and let is wash over her, the feeling of his enormous cock fucking her tight, virginal asshole.

He pulled out of her and paused.

She opened her eyes.

'Does that feel ok? he asked. 'It looks like it's hurting you.'

She shook her head.

'That's very sweet of you to check, but you don't need to worry. It feels amazing.'

It was actually a little uncomfortable for her, but she made sure it didn't show on her face.

The next time he thrust upwards she pushed all her weight down on him at the same time, to try to take him all, but her ass was just too tight to get the last few inches.

Relax, she said to herself.

She reached down and started massaging her pussy, and that did the trick. The sensation of her pussy took her mind off the discomfort, and next time he thrust she sank all the way down. His entire length was buried inside her.

'What do you think your friends will say when you tell them you fucked a mother and daughter?' she asked him, as she raised herself off him and impaled her ass again.