Amber’s Craigslist Hookup Ch. 01


On her way home from work, Amber lamented about yet another upcoming lonely weekend stuck in her apartment with her rabbit and her laptop and flipping through channels. Her divorce had become final two months earlier, and the guy she began seeing during their separation had left her for a teenybopper named Nicole.

Amber desperately wanted a man. A long-term relationship probably wouldn’t be the worst thing in the world, she thought, but mostly she just wanted to fuck. If it meant being a booty call, so be it.

It’s just my fucking luck I was born with the libido of a porn star.

It had been about two weeks since she’d had a real cock in her. She and her first ex, Bobby, went on a date to see if the old fire could be rekindled. But it couldn’t. Instead, Bobby fucked her. He was still a great fuck, but he had never cared for Amber not being hetero. Amber loved women, too, but pussy and a strap-on were simply no substitute for a real cock in her. While the naturally dark blonde Amber thought she was still very attractive at 34, she knew she couldn’t compete with the younger girls who had men of all ages drooling over them. On the upside, Amber felt she could pass for a younger woman. Plus, she had experience and also did anal, which the MILF fans loved. Most younger girls thought of their assholes as exit only.

Not Amber.

And Amber hated the MILF acronym. Originally, “mother I’d like to fuck” applied only older women over thirty who had borne children, but now it seems like it got applied to every woman over thirty whether they’d had kids or not.

Amber was adamant that she was not a MILF.

Then Amber thought about her friend Marie’s suggestion about posting an ad on Craigslist. About six months ago, she’d found her new boyfriend, Tom, on the free Internet classified service and they seem to have hit it off fabulously. Amber had used Craigslist a year earlier to sell furniture and other things she didn’t need or want. But a man? She thought about calling Marie and asking if she was interested in them having company, but quickly dismissed it. She’d been with Marie a few times, but Marie would never do a threesome.

Geena yeah. But not Marie. Oh, she doesn’t know what she’s missing.

Amber had been involved in a lot of MFF threesomes in her time. She loved them. However, MMF’s were a different story entirely. She’d been in exactly one and she swore she’d never do another one. It happened several years ago when she took a brutal DP from two very hung young guys who saw her in a bikini at the pool at her old apartment complex. The guys stared at her and began yelling suggestive comments. Amber loved the attention. She walked to a secluded part of the apartment complex near the pool and seductively motioned for the young guys to follow. When she was certain no one but the guys could see her, she bent over and flashed them her hairless pussy and her asshole and told them to put up or shut up. She walked up to her apartment and they followed. The sex was incredible until the fateful moment. While riding one of the guys cowgirl, the other guy unexpectedly pulled his cock out of her mouth, got behind her, pushed her forward, and pushed into her asshole. She’d been wanting to try double penetration and didn’t resist. But they got carried away and slammed her mercilessly. They came; Amber didn’t. They left her bruised and feeling so stretched out that she spent a painful, sleepless night fretting that permanent damage had been done to her. But she healed completely within a week. She didn’t blame the guys though. They didn’t know she was hurting so much. She’d actually fucked them again, albeit separately, and they were pretty good. She didn’t mention the DP debacle.

“I’m probably gonna regret this, but…” she sighed as she booted her Macbook. As soon as it was up, she opened the browser and clicked the Craigslist link in her bookmarks and clicked the “men seeking women” link. After a good half hour minutes of reading posts, no one interested her. She groaned in frustration.

Amber was about to write her own ad when she came across a four day-old one: “Shy Lonely 40’s SWM Seeks Fun With Late 20’s/Early 30’s SWF.”

Shy stated he had been divorced for three years, rarely nişantaşı escort drank, hated drugs, and wasn’t a social butterfly. He didn’t care for teenaged adults, said he was a little on the pudgy side, didn’t play games, and wanted likewise from a woman. And he was local!

Amber clicked on the reply button and began to type:

“Hey Shy? Still lonely? SWF — 34 — no kids — horny as hell — YPGM — NSA.”

She sent the message and launched her mail application.

“Yeah, I’ll bet he’ll be emailing back me real soon,” said Amber sarcastically. She got up, pulled out her hideaway bed, then went to the kitchen for a diet soda and quickly drained it. She went back into her living room and made sure all the drapes were closed. She stripped down, opened the drawer on her nightstand, and pulled out her trusty rabbit. She laid down on the bed and got her pussy wet and had just inserted the head of the toy in her when she heard the new mail notification alert.

“Probably just a stupid ad,” she said annoyed, getting up to look. But no! It was from Shy! And he’d included a pic! Shy was a mixed bag. He was broad shouldered and had thick, wavy dark brown hair and a salt-and-pepper beard. He had a nice genuine-looking smile and he kind of had the square jaw thing going. Amber thought he should probably spend some time in the gym to tone up.

Amber sighed. She’d had better and she’d had worse.

If he hasn’t gotten any in three years, he’ll be horny as hell. Good for me!

She hit the reply button, wondering whether she should be direct or playful. The ad said he didn’t play games and expected the same, but Amber knew most men like playfulness to some extent whether they wanted to admit it or not. Still, she decided on the direct route.

“Shy, thank you for responding so quickly! I’m including a pic. Amber.”

She selected a sexy honest photo of herself in tight jeans and a tight frilly top which showcased her figure. She attached it to the email and hit send. In the interim, she pleased herself with the rabbit and came. Then the new mail alert sounded again:

“Amber. Thank you for responding. You’re very lovely! Can we meet tonight? Say the Breiel McDonald’s at nine? Greg.”

Amber smiled.

Greg’s probably trying to make me feel safe, she thought. Well, it’s public and on a major road. That late on a Friday, it’ll be mostly kids on dates. And cops are always patrolling the area.

She looked at the clock. 8:11. Enough time for a quick shower.

Amber hit reply and typed her acceptance and clicked send.

She showered and dressed quickly. Tight jeans and a slightly tight light blue cotton button down shirt which revealed her taut belly. She was not lanky or sculpted; she had just enough baby fat to make her midriff look smooth. She chose not to wear a bra. She was proud of her naturally firm breasts and only wore a bra at work and on select occasion. The drive to McDonald’s took less than fifteen minutes. At about nine, she walked in and saw Greg sitting at a window seat. She took a nervous deep breath and walked over. He stood up.

“Amber? Hello. Thank you for coming,” he said standing up and extending a big hand. “I’m Greg.” His voice was slightly gravelly, but he spoke softly.

“Amber,” she said, accepting it.

“A pleasure,” he said.

“May I get you something?” he asked nervously, gesturing for her to sit.

“No, thank you,” said Amber. She noticed that he was nervous, but was doing a fairly good job of hiding it. After several minutes of chitchat, Amber decided she liked Greg’s personality. He was genuine, funny and very polite.

“Listen, Greg,” she said. “I don’t think we need to get caught up in pretense. You and I both know what this is about.”

He nodded. “It’s been a while for me. A couple of years. I was afraid you’d think I was some sort of creep.”

“I’m a pretty good judge of character, Greg,” said Amber reassuringly. “So let’s go. My place. I’m driving the silver Nissan. Follow me.”

When they were outside, Amber asked: “Oh, do you have condoms?”

“Actually, no,” he said, shaking his head.

“There’s a Walgreens up the road,” she said. “We’ll split the cost, okay?”

Greg çapa escort nodded.

They went inside the Walgreens and quickly made their purchase. The clerk, a woman in her sixties, didn’t bat an eye. The drive to Amber’s Village Drive apartment was short; they missed every single red light.

“Nice place, Amber,” he said when she opened the door for him.

“Thank you, Greg,” she said. “Something to drink?”

“No, thank you,” he said. “But could I shower please? I’m afraid I got a little worked up and…”

“Sure,” said Amber, nodding. “Second door on the right.”

“Thank you.”

Greg was in and out of the shower in about eight minutes. He emerged fully clothed. Amber, who had taken off her jeans and top and was wearing a sheer bra and panties, resisted the urge to kid him.

Amber took the first step and planted a kiss on his lips. Soon they were Frenching.

“Oooh… Nice,” she said.

“Nice?” said Greg. He put his big hands on Amber’s waist and pulled her close and kissed her deeply and began fondling her. Amber moaned. He moved behind her and kissed her behind her left ear and the nape of her neck and began unclasping her bra. She felt his bulge on her ass.

“Oh yeah…” moaned Amber softly. Soon she was topless.

“Oh, those are wonderful,” he said, reaching around and cupping them. He moved back in front and bent down and swirled his tongue around her nipples while rubbing the crotch of her panties. He pulled them down and soon Amber was completely nude in front of this strange man.

And she was wet. Really wet.

“Oh, Amber… You are so gorgeous!” he said.

She moaned in appreciation. Then she kissed him and began licking him down the middle of the chest to his waist. She undid his belt, unbuttoned his jeans, and pulled them and his boxers down. He wasn’t overly long; around seven inches, which suited the 5’2″, 105-pound Amber perfectly. But he was thick. She took all of him in her mouth and tongued the head. He was fully erect in seconds.

“Oh, God… Oh, Amber! Uhhh…” he closed his eyes tightly and yelled “gahhhhh!”

She stopped after a few minutes. Greg took a deep breath and exhaled.

“Oh, damn, girl! That was amazing!” Greg exclaimed. He then pulled her up gently and laid her on the bed and gently squeezed her breasts and licked her sensitive nipples, pulling them with his lips. He licked her all the way down to her mound, but stopped short and began kissing the insides of her thighs instead.

“Oh, a man who knows foreplay,” Amber giggled and moaned and sighed.

“You smell fantastic, Amber,” he said. But he didn’t go to her pussy.

“Oh, come on, Greg!” pleaded Amber as she rubbed and patted her clit. “Put that mouth where I want it! Now!”

Greg ignored her. He turned her over and kissed her ass. He ran his tongue right over her crack and up to the small of her back, causing her to whimper and squeak.

“Oh my God I love your ass, Amber!” he said. He pulled them apart and brushed her asshole with a calloused finger, then licked the perimeter.

“God! Oh fuck,” she yelped.

“You do anal,” he said. It wasn’t a question.

“Uh-huh…” moaned Amber. She could sense him smiling.

“Alright,” said Greg, turning her over. He opened the bottle of lube and put a small dab on the tip of his fingers. “Tell me when it feels good,” he said.

Before Amber could respond, he slowly pushed his index finger deep into her pussy, causing her to groan and sigh. He put another finger gently into her asshole and fingerfucked both openings simultaneously.

She suddenly jerked and stiffened.

“Ohhh… FUCK!” she moaned as she shuddered and came.

“Oh yeah,” said Greg. He kept fingerfucking her holes and Amber orgasmed with another loud groan. His massage became firmer and faster.

“Oh! Oh fuuuck! Fuuuck!” she said. She began panting. “Oh, Greg, dammit don’t fucking stop! Feels… so… fucking… good… Ohhhhh!” she roared. The orgasm was more intense than the first two. She shuddered and convulsed. Drenched in sweat, she fell back breathing hard and laughed.

“Oh damn, Greg!” she exclaimed. She kissed him. “You haven’t been with a woman fatih escort in three years?”

He shook his head slightly. “Two years or so. Long story why,” he said somberly.

Amber didn’t press him.

Greg leaned over and grabbed a condom out of the box. He quickly opened the small package and extracted it and rolled it over his throbbing cock. He grabbed her hips and pulled Amber down towards him. He put his cock at the entrance to her pussy, rubbed the head against her entrance, and slowly pushed in.

“Oh, man…! Oh!” he moaned as he entered her. Amber gasped at his width. Greg slowly buried his cock in her; Amber groaned every inch of the way. After it was in halfway, he thrust hard, causing Amber to scream.

“Fuck yeaaaaaaah!”

And he fucked her with long, hard strokes.

“Oh, yeah!” moaned Amber. “That’s it, baby. Fuck me deep.”

He bent down and kissed her.

“Oh, gawd! Oh, yeah! Now go a little harder, Greg!” He complied.

Amber pushed him over and rode him cowgirl. He sucked on her tits and she met his thrusts, and soon they were locked in rhythm. After several minutes, Greg felt himself coming and stopped.

“Reverse cowgirl,” he said, motioning Amber around. “I wanna see that fantastic ass while I fuck that pussy.”

“I like doggy better,” said Amber, moving off him and getting on all fours and sticking her ass high in the air. Greg grabbed her hips and re-entered her and fucked her to another shuddering orgasm.

“Oh fuck, I can’t take this,” said Amber, reaching for the lube. She smeared some on her fingers and worked it into her asshole.

“Oh, yeah!” said Greg, who began massaging her back door and used some of the excess on himself.

“Pound my ass, sweetie,” commanded Amber with a big smile on her face. She reached back and pulled one cheek aside, exposing herself entirely.

“With pleasure, m’lady!” he said. Amber giggled.

Greg put the head of his thick cock against her and pushed.

“Slowly… Ohhhhh, fuck!” Amber growled as it went past her sphincter. “Oh damn that’s thick!”

She panted and whimpered as Greg’s cock filled her. “Damn! Oh, fuck that fucking asshole!” she commanded again through her teeth.

Greg fucked her ass like no one had before.

After several minutes, Greg yelled, “Oh, fuck, Amber! Oh… I can’t hold back, girl!”

“Don’t cum yet!” said Amber. “I want it.”

He pulled out and yanked off the condom. Amber turned around and spit on his cock and deep throated him. Greg exploded down her throat in less than half a minute.

“Ohhhhh damn! Ahhhhh!” he yelled as he erupted. Amber greedily swallowed and sucked out every drop. Greg nearly lost his balance. When he was done, he laid down.

“Oh fuck!” he said breathing hard. “Oh God, Amber!”

He leaned over and kissed her.

“You’re amazing,” he shook his head in disbelief. Amber was all smiles.

Just then, her cell phone rang. She reached over and picked it up. The caller ID said it was Geena. She slid the slider to open. Greg listened intently but tried to act like he wasn’t.

“Hey, Geen… What’s up?” asked Amber.

“No, actually, I’m entertaining a friend.”

“No, you probably don’t know him.”

“No! Aw, you know I hate those places. I placed an ad on Craigslist.”

“Oh, come on… He’s a very nice man.”

“Yes we did.”

“Wha…? Pot, meet kettle.”

“Good? You don’t know the half of it.”


“Don’t I know it! Um, say, Geen… Hold on a sec, huh…?” she put the phone on mute.

“Greg, sweetie…?” cooed Amber. “Um, I have a friend who…”

“A guy? Uh-uh! No way!” interrupted Greg. “Not my style.”

“No, no, Greg,” said Amber laughing. “Her name is Geena. I call her Geen for short. We’re very close friends.”

Greg’s eyes went wide in understanding.

“Is she hot?”


“Well okay then!”

Amber grinned and unmuted the phone.

“Sorry, Geen… If you’re lonely, come on over.”


“I told you he’s not my boyfriend! You’ve helped me out a lot. And as bitchy as you’ve been since what’s-his-name…?

“Yeah, Mike. Well, ever since Mike left you’ve been a little on the bitchy side. You could use a good fuck. He’s not some kid like the ones you’ve been with lately. So?”

Amber grinned. “See ya soon, babe.” She hung up.

“She’ll be here soon, Greg. I guess you can tell you’re not going anywhere for a while.”

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