Amelia's Answered Ad

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A May-December encounter goes wrong...and then right.
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Roger had counted himself so lucky, months ago, when he'd answered an ad looking for an "older gentleman" who could...shall we say, satisfy the needs of a younger woman. Of course hundreds of people had probably answered her ad, but she had written back to him!

Her name was Amelia. She was young, only 35. Brunette, blue eyed, and on the larger size, all of which he liked. She sent him a photo when he requested, and when he first saw it the very idea of doing her got him hard. Then the trouble started, when she asked to see him. He'd lied about his age, see. He said he was 65, but he was actually a few years older. He'd been worried about scaring her off, or her thinking he couldn't handle what she wanted. He also had a gut on him, and not a lot of hair left. He wasn't ashamed or anything, but he was concerned she wouldn't like his appearance.

So he made excuses about the photo, said he didn't have a camera and didn't know how to email one. A weak lie, he knew, as he took photos for a living! But she didn't have his last name so it's not like she could Google him.

They first gotten together after a month of talking. She knocked on his door on a Saturday afternoon, wearing a dark blue polo and jeans. Simple, classy and not too revealing. She didn't know how it was going to go, she told herself. She might have to leave. When the door opened, she was in shock.

Roger was...well, not what she expected. He was definitely older, but she doubted he was only 65. He had a shock of white hair around a bald head, with wrinkled skin and a gut. But most alarming of all were his clothes, or lack thereof. He was clad only in a pair of boxer shorts!

Roger stepped aside and invited her in, and she did step inside after a moment of hesitation but she clearly was having second thoughts. Roger could see it in her eyes, she looked ready to run. Her eyes kept flicking towards the door. He reached out to hug her, and she backed away.

"I...uh...look, I'm really sorry, but I think I've made a mistake," Amelia said.

Roger smiled, and continued his approach. "Now honey, I know I probably look a bit like your grandfather, but don't you know not to judge by appearances?"

Amelia put her hands up defensively, keeping him away. "Look, I'm sorry, I don't want to be rude, but this is just...this is too much for me to handle. I'm going to go."

Roger was worried, but they'd been talking for a while, and he knew how badly she needed release. She'd confided in him through their messages, and he knew if he could just get his hands on her...

So he offered her a backrub. Told her clothes on, standing. She didn't need to lie down or anything. Just to relax her. She seemed unsure, but he was determined, so he gently turned her around so she was facing away from him. He gathered her long hair up and moved it over her shoulder. The he started rubbing her shoulders and upper back, gently. Lovingly. He moved slowly.

He could feel her relaxing under his hands. He moved down to her lower back, rubbing there too. Then he moved back to her shoulders and massaged the tops of them, with his fingers trailing perilously close to her breasts. He could feel her stiffen again, so he slowly moved back down.

Take it easy, he told himself. You want this to be her choice too. If at all possible.

He asked her if it felt good, and she just moaned in response. A better reaction that he'd hoped for! He reached down and put his hands inside her shirt, touching her skin instead. She didn't tense up at all...in fact, her head lolled back. She was into it!

He moved his hands up to where her bra strap was, and began massaging there, moving his hands towards her sides at the same time while pressing with his thumbs towards her spine. He inched his hands around slowly, to see if she would stiffen or stop him. She didn't. Once he was halfway around, he quickly slid his hands the rest of the way, cupping her breasts in his hands.

"Oh God!" she exclaimed, jumping. She reached up to grab his wrists, trying to pull his hands off her. Roger gripped tighter and brought his mouth to her ear, pressing his entire body against hers.

"Shhh, shhh shhhh it's okay Amelia," he said gently. "Don't worry, its fine."

"No...but I...this isn't right..." She stammered. She could feel him against her, feel his hard cock pressing into her backside. She shouldn't have let him touch her, she realized now. But he didn't let go. He massaged her breasts, making her gasp and he felt her nipples growing hard. He moved his lips down and started kissing her neck.

"You're so beautiful," he whispered in her ear. He released her breasts so he could unhook her bra, all the while she was stammering at him to stop. But she didn't really mean it, he could tell.

He reached back around, pushing her bra out of the way so he could grab her mounds, skin-to-skin. They felt amazing. Firm and round, with such hard little nipples. She was still saying no, but she wasn't pushing on his hands anymore, and she wasn't struggling at all. He knew once he had his hands on her she'd be into it.

Roger knew he needed to take the opportunity now, before it slipped away from him. He ran his hands down her belly, rounded and gorgeous. He ran them around the waistband of her pants, moving towards her backside again. He enjoyed the feel of her skin, touching every part he could. He grabbed her left hand and placed it on the crotch of his pants, wrapping it around his cock.

She jumped, startled, but didn't immediately try and remove it. Her movements seemed unsure, tentative. In truth, Amelia was freaked out. Inside her head was screaming at her to leave, to run. Why she had let him touch her she had no idea. Yes, she needed release, but not like this. Not here, not with this man...she had to do something, now.

Quickly she moved away from him, pulling her shirt back down. She'd rehook her bra after she got away.

"I'm sorry, really, I am - I didn't think this through, I don't know what I'm doing..." she moved towards the door. "I need to go."

She turned the handle and was about to open it, when a huge hand smashed against the door above her head and shut it closed. Startled, she whirled around.

There was someone else in the room! He was tall, young, and looked incredibly strong. His dark skin glittered in the sunlight coming through the window, but not nearly as much as his eyes were glittering. He looked her up and down, and she had the sudden feeling of being horribly exposed. His hand was still on the door above her head. She felt very small.

Roger stepped over to where they were, shaking his head. "Ah, so close. I do wish you hadn't tried to leave, my dear. I was hoping I could surprise you with Zach. But now that you two have met, we should probably take this to the bedroom." With that, Roger started down the hall and gestured at the two of you to follow.

What. The. Hell. Was. This? There was no way she was following. She shook her head, refusing to believe this. She looked back up at Zach, who tossed his head in Roger's direction, indicating she should follow. Amelia shook her head. Zach rolled his eyes, and reached for her.

She shrank back into the doorway, but with ease he grabbed ahold of her. He was gripping her upper arm and was pulling her towards the bedroom...oh no.

Before she could process what was happening, she was in the bedroom and the door was locked behind her. She started to back up but immediately bumped into Zach, who grabbed both her arms and pinned them behind her back with his right hand. With his left he reached around and pushed her shirt back up, exposing her breasts to the air. He started kneading her left one, and she heard a low chuckle when her nipple got hard.

"Hey now, don't start without me!" Roger said, moving away from the edge of the bed. He approached her with a lecherous smile on his face, and she started to panic. This was more than she had bargained for! Of course she had a fantasy of more than one guy, who didn't? But she wasn't prepared for it. Not like this. She didn't want him! She couldn't!

Roger grabbed her face and kissed her roughly. His left hand stated kneading her other breast, while his right trailed back down her stomach. She tried to jerk away, but Zach was holding her firmly.

Roger slipped his fingers into her jeans, then her panties...he began sliding his hand down. Amelia was horrified, she couldn't let him touch her! Not there! But it was too late. His hand was already there, slipping between her fleshy folds and rubbing on her clit.

She gasped, shaking. It had been so long. So long since anyone else had touched her like that. She couldn't want it, it was wrong. But as she felt four hands on her the rational part of her mind began to slip away.

She moaned as Roger's finger began to stroke her. He could feel her wetness. He knew she'd succumb to her desire. Having Zach there had been an insurance policy for him, one which had come in useful. He'd rather have had her to himself the first time, but no matter.

Roger removed his finger, and brought it up to her face, stroking her lips with it. She turned away.

"Oh, naughty girl," Roger said. "You need to do what we tell you."

Suddenly Amelia felt another, larger hand moving down into her pants. She knew she should protest but she was curious...and excited. As Zach touched her, she gasped and Roger slipped his finger into her mouth. She started sucking it, and could taste herself. She was starting to lose control.

Zach released her hands, but kept her right one and placed it against his pants. Her heart began to race. She could tell, even through his jeans, that he was enormous. Roger in turn took her other hand and put it on the front of his shorts. She was now feeling two rock-hard cocks, and it felt amazing.

She wasn't even thinking anymore as she reached down inside Roger's shorts and took ahold of him. He made a moan of pleasure.

"Yes, yes, good girl Amelia," he cooed.

She heard a zipper and knew Zach was opening his pants too. She moved her hand and looked down as seconds later instead of bulging jeans she was greeted with the sight of the biggest cock she had ever laid eyes on. It was at least 10 inches long, and 2 inches thick! She was almost salivating...she couldn't wait to try and fit that in her mouth.

Rogers' hand slipped her jeans off as Zach continued his explorations between her legs. As her clothes slipped off she parted her legs, allowing him easier access. She didn't care anymore if it were wrong. She wanted this. Roger grabbed her and kissed her again, at the same time Zach found her pussy and starting pressing inside her with a finger, making her gasp. Roger took advantage of her open mouth, and explored wildly with his tongue.

Zach began pushing Amelia over to the bed, and she obliged. He set her down on the edge and she parted her legs for him, spreading open like a flower. He pushed two fingers into her pussy as his thumb touched her clit, and she moaned on the bed. Roger straddled her face, smacking his cock on her mouth. She opened wide, and he pushed himself inside.

God, what a feeling. Her mouth was soft and he felt her lips wrapping around his shaft. She started bobbing up and down on it, sucking him in deeper. Roger watched as Zach knelt between her legs and started licking her.

With the very first lick on her clit, Amelia spasmed. Roger pushed down on her shoulders and Zach held her hips as she came, hard, all over Zach's mouth. She was moaning but the sound was muffled by Roger's cock. There was so much juice, and Zach was eagerly lapping up every last bit.

Roger grinned at him. "Was that good?"

Zach then spoke for the first time. His voice was incredibly deep. "Oh yeah man, it was the best ever! How many times do you think we can make her do that?"

Roger looked down at Amelia, who was wide-eyed with his cock stuffed in her mouth. "Hmmm. What do you think about starting with five?" She shook her head, and Roger could just make out her muffled "I can't."

"Oh don't worry baby, I think you can," Roger said. "We'll make you feel good."

Amelia wanted to protest, but just then Roger pulled himself out of her mouth and before she could say a word, Zach turned her head to him and thrust his massive shaft into her mouth. Roger was a decent size, but Zach was enormous! She could barely take it. She couldn't help thinking about where else he might be putting his shaft. The idea made her shake, not with fear but with pleasure.

Roger was between her legs now, running his hands all over her bare flesh. She heard a tearing noise and realized he was putting a condom on. Oh no, no, she didn't want him fucking her! He was so old, she couldn't let this happen! But before she could do anything she felt his cock start pressing against her slit, and slipping inside.

"Oh, Amelia baby, you feel so good," Roger said, sinking all the way in. She was tight, and it felt so amazing. He started moving back and forth, burying his shaft in her. He was trying to hold back but it was hard, when suddenly she tightened around him. He looked down and she was staring right into his eyes, the little minx!

"Oh you're a bad little girl, aren't you?" Roger said. "You know just what I like!" with that he starts pumping her, harder and harder. Zach in turn starts fucking her face harder, shoving more of his massive member into her mouth.

"Oh you have got to feel this," Roger said.

"Don't worry I'll take my turn," Zach said with a grin. Amelia looked up at him, and he could see the fear in her eyes. He stroked her face. "And don't worry, I won't hurt you."

Amelia wasn't sure if he would or not. She just hoped he was telling the truth.

Roger was fucking her slower now, concentrating, trying to keep from cumming. He pulled out and kneeled between her legs, savoring the sight of all the pussy juice still there. His tongue flicked out and he felt her jerk. He'd gotten the impression from Zach's ministrations earlier that she might get off the strongest from tongue action.

He flicked his tongue back out, and ran it around her clit. The reaction was almost instantaneous, with a shuddering moan she climaxed again! Roger latched on and started sucking on it, pumping two fingers in and out of her at the same time. He wanted another orgasm! She moaned but wasn't cumming. He suddenly had an idea.

He licked his fingers, then, while still licking her clit, he slid them down and touched her asshole. He felt her freeze underneath him, and could hear a whimper. That was a good sign as far as he was concerned! He continued to suck on her clit and he began pushing one finger inside her.

That did it, with a sudden muffled-by-cock scream, she came again. Roger latched his mouth around her pussy and sucked hard. So tasty!

Amelia was feeling spent. Three orgasms had rocked her world. She had no idea sex could be like this! She wanted to thank these two men for making her stay, for stripping her and using her like the little slut she was. She never wanted to stop! But she had no idea what was in store for her. But she was about to find out.

Roger stepped back from her, stroking his cock. He brought it back up to her mouth. Zach pulled away and she took Roger's again, sucking deeply. She heard another tearing sound and realized Zach was putting on a condom now. She started closing her legs a little bit...she was scared. He was so huge. But then Zach started rubbing her legs and stroking her.

"It's okay baby, I promise it'll feel good," he said. Amelia just looked down at him, Roger's cock in her mouth. She had no choice but to trust him. There was no going back.

Zach lined up the head of his cock with Amelia's pussy, and pressed. He could see the skin stretching, trying to wrap around him. A little more pressure and the head of his cock was in. Zach glanced up at Amelia. Her eyes were closed. He could see a little furrow in her brow. She was okay.

He started pressing in deeper. He heard a whimper, but didn't react. He knew he was stretching her. She had been tight on Roger's cock, but it was nothing compared to Zach. How he loved stretching young pussy out! Sometimes they cried, sometimes they begged him to stop. Sometimes they loved it. But every time they came back again because nothing else could satisfy them after his massive member.

He was a little over halfway in when something gave way and without even meaning to, he slammed home, all 10 inches of his massive cock buried balls-deep in her sweet cunt. Her eyes went wide, and she was clearly screaming, but all her screams did was milk Roger's cock. Roger moaned with pleasure as Zach looked right at her, and smiled a wicked smile.

"Now I'm going to fuck you," he said. He took ahold of her hips, and hooked her legs on his shoulders. He began to stroke back and forth, moving slowly at first. As she got used to his size he started to speed up, pumping into her. He starting grunting with exertion.

"Little slut," he said, still fucking her, "You can take it, can't you? Little whore wants cock and she doesn't care where she gets it from, do you?" Zach said. Amelia coughed and gagged as Roger suddenly pulled away from her mouth, smacking her with his cock.

"Yeah she is a little slut, isn't she?" Roger said. "I'll bet she'd ride you good and hard. Flip her over."

Zach barely broke rhythm as he rolled them over. Now Amelia was on top, and he was still bucking his hips into her. She ground down on his cock, throwing her head back and moaning with pleasure. She felt so stuffed. Roger's hands reached around and started pulling at her nipples, and it just furthered her excitement. She had never felt more sensual in her life.

Roger pushed Amelia forward a bit, so her body was parallel with Zach's. She braced herself on either side of him with her arms. Zach started slowing down, using long, slow strokes. Roger trailed his hands over her backside, marveling. Her skin was so smooth and gorgeous. He licked his finger and touched her asshole. She clenched her butt cheeks, but he wasn't having that.

"Oh no no, remember little girl you have to do everything we say," Roger said sternly, smacking her ass. "And I say I want to see your little pucker."

After a pause, Amelia unclenched. Roger grabbed the baby oil he'd stashed on the bedside table, and dripped it down her crack, rubbing it right on her ass.

"What are you doing?" Amelia said, her voice fearful.

"What do you think I'm doing?" Roger replied. "I'm making sure you can take what I'm about to give you." He pushed a finger in her ass, making her gasp.

"No, no, please," Amelia said.

"Now how am I supposed to believe you?" Roger asked in a disappointed voice. "You tell me not to touch you, but then you let me. You tell me not to fuck you, but then you let me. You grabbed my cock and pulled it out of my boxes without me even telling you too. So why should I believe you now?" He grinned wickedly as he pressed his finger in farther.

"Hurry up," groaned Zach. "I wanna split this slut in two!"

Amelia was scared. What did he mean? She tried pulling herself off him but Zach's hands were gripping her upper arms tightly, holding her firm. She felt Roger's finger withdraw and she breathed a short sigh of relief - until she felt the head of his cock against her asshole!

"No -" she started to say, when he shoved into her, hard, the whole head of his cock entering her.

Amelia screamed. Zach grabbed the closest thing to him, her panties, and shoved them in her mouth to muffle her cries. He held her fast as she struggled. Roger pulled out for a moment, watching her asshole shrink again, before plunging back into it, further and deeper than before. Amelia screamed again, tears leaking from her eyes. She stared wide-eyed at Zach below her, clearly begging him to help her.

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