Big Blind Date

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Danny Finds a Big Woman Who Will Do What Good Girls Won't.
1.9k words
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It was going to be Danny's last fling. Before he settled down, he wanted to experience the kind of sex he had seen in a million porn videos. None of the nice girls he had dated would do the things Danny wanted to do.

The furthest he had gotten was when Sally Hanson sucked his cock until he was about to come, then jerked him off into a tissue. He wanted to have a woman swallow his cumload or take it on her face or breasts. And he wanted to try anal sex. The one time he had tried to mention assplay to Sally, she cut him off and ended the date. And there was other kink, too he wanted to try or at least see. The BDSM videos he had seen were dark and foreboding but he felt a twinge of pleasure when the female 'victim' would beg for more and he could her the pain in her voice. That kind of passion to want more, even if it hurt, Danny wanted to be with a woman like that.

"Are you SURE?" Danny was almost yelling at his sometime friend Louis.

"Yes, I'm sure. She will do everything on your list and more."

"How can you be sure? And is she, you know, clean? And big tits?" Danny pushed.

"Look, she's married but they don't fuck. She only goes out a couple times a year. And she's a nurse, so she's not gonna give you anything but a good time. And she has very big tits. This is a perfect setup," Louis assured.

And he was right. It was perfect. When the day of their meetup came, Danny walked into the deserted motel bar right on time. He thought he was their first, but as he looked around the furthest back corner, he saw a large woman in flowing satin. A very large woman. Danny had thought that his blind date might be a big woman, but Candy was enormous. She had a pretty face and she had just finished a glass of wine when Danny spotted her.

They spoke awkwardly and decided to go to the room that Danny had registered and pre-paid for. When Candy got to her feet, Danny was stunned. He was six foot two. Candy had to be six foot four. And Danny's 180 pounds (82 kg) was dwarfed by what he reckoned to be her 300 pounds (136 kg). Once in the room, things moved quickly.

Candy had a small bag that she began to unpack. Danny saw lube and some lingerie.

"I want you to strip for me," Candy told him.

Danny had decided back in the bar to go with the flow. Although he wasn't turned on by Candy's size, he wasn't turned off by it. And she did have some monster big tits. Those should be fun to play with. If she wanted him to strip, he would give her a thrill. He was in good shape, he thought.

Danny moved to the music of the radio as he took off his shirt and undershirt. He kicked off his shoes and took off his socks. He reached for his belt.

"Turn around. I want to see your ass when you pull your pants off," Candy purred.

Danny was enjoying being the stud, like a male stripper fantasy. He faced away from big Candy and unbuckled his belt, unbuttoned his pants and pulled them down, shaking his ass at her. He stepped out of the pants. Danny noticed his cock was about half-hard as he began to pull down his boxers. He thought Candy would be impressed when he turned around and showed her 'the goods'.

Danny bent over to pick up his boxers and he felt a hand on his back, holding him down. At the same time he felt a warmth on his asshole and then a sudden slightly painful penetration followed by deep pumping in and out. Danny realized that Candy had played him. But he couldn't deny that whatever was pumping in and out of his asshole felt good. He felt a hand reach around his waist and grasp and stroke his cock expertly. He was fully hard now.

Eventually, Danny felt the pumping in his ass stop and the small dildo was withdrawn. As he turned back around, Danny saw the six inch long, inch wide plastic toy as Candy put it away. She laid back on the bed and spread her legs wide open. Her fingers pulled open her pussylips and she beckoned Danny.

"Come have a taste," she cooed.

Danny fancied himself a top-notch pussy eater. She got one on him with her toy. Danny was going to show her he had a few tricks too. He licked her pussy up and down and sucked on Candy's meaty lips and licked up to her big, hooded clit. Candy was beginning to move her hips in time to the licking and sucking. She was building up to a big climax.

Danny didn't want her to come too soon. He wanted to play with her. He eased off licking Candy's clit and slid a finger into her wet pussy. He pumped the finger and then pushed in a second. Candy had a big cunt. Danny slipped a third finger in and pumped them in her wet pussy easily. Only when Danny made a cone of his four fingers and began to work them into her cavernous pussy, did he feel her pussy begin to feel tight.

"Are you going to fist fuck me? Are you going to shove your whole hand in my fat, sloppy cunt?" Candy's voice betrayed a little discomfort.

Danny twisted his hand and tried to drill it down into Candy's cunt. He pushed in hard and Candy grunted loudly.

"Don't stop. Push in," she whispered between grit teeth.

It turned Danny on more than anything he had ever know. He looked up at the giantess and she was holding her huge breasts. She reached down and put her hands on Danny arm and pushed it into herself. Danny took a deep breath and pushed his hand hard into Candy's cunt. She screamed into a pillow. But her hand on Danny's arm pushed and pulled lightly. He slowly made a fist of his hand inside her and began to pump his fist as deeply as she could take it and then out until it stretched her big pussy. He pumped her and she built up to an almost earth-shaking climax. Again, she screamed into the pillow. Danny carefully extracted his hand.

Candy needed a little time to collect herself but she was soon moving toward Danny.

"I hear you've never had deep throat. Get ready."

It was Danny's turn to lay back. Candy portioned herself between his legs and all he could see was her pretty face and those huge tits hanging down like udders. Candy's hands were soft, but strong and her mouth was warm and wet. She was the most skilled cocksucker Danny had ever imagined. She had his cock harder than it had ever been. She used her teeth and her lips and it felt like two women were working on his seven inch, thick, cock.

And then simply took it down to the base and held it there. She gulped and gurgled. It felt amazing to Danny. Candy began full-length pumping his cock from tip to base. Her hands massaged his heavy balls, wet with Candy's slobber and excess spit. Candy pulled off his cock and took both Danny balls into her mouth and her tongue massaged each ball. She returned to deepthroating his cock and as she cradled his balls in her hand, she snuck a finger to dip into Danny's asshole.

That reminded him of the other "fuck-it list" item. Fucking Candy's ass.

"Alright, Candy. What I'm going to put in your ass it a bit bigger than what you put in mine," Danny chuckled.

Candy dutifully crouched on all fours, presenting her ass to Danny and holding her massive cheeks far apart. Danny was eye to eye with her anus. He applied a lot of lube to the outside and pushed a finger in a little to lube it more. Candy was looking back at Danny as he squirted lube on his hand and stroked it onto his achingly hard cock. He smiled at her and went to work.

Danny positioned the tip of his cockhead at her anus and pushed. It did not yield. He pushed steadily, with increasing force. Candy cried out and Danny pulled back.

"No. Don't pull out. Push in. Fuck my ass. It's going to hurt. Hurt me. I want to feel it. I want your big cock in my asshole. DO IT!"

Danny smiled. This is what he wanted. She was begging him to force his cock into her asshole, even if it hurt. She wanted it to hurt. He positioned his cockhead at her anus and rubbed it around, pushing in. Candy began to moan. Danny began to pump his hips even though her anus was not giving way. Each pump was more forceful and each hurt the big woman's ass more. Danny squirted the last of the lube where the friction was and his cock began to slide in very slowly.

Candy's asshole was very, very tight. Danny had assumed he was hurting her. He could hear her grunting from the pain.

"More. Fuck it. Fuck my asshole like you mean it. Give me all of your cock in my ass. Make me feel it!"

Danny grabbed the large woman's hips and began to thrust his hips violently in and out. His cock forced its way in again and again. Her ass wasn't loosening up. It was tight, so tight. Danny wanted to unleash his full desire.

"Beg me to rip your ass open, Candy! Beg me to hurt your ass! Tell me that's what you need!" Danny whispered in her ear.

Candy began to demand Danny fuck her ass hard and fast. Even as she winced from the pain of his cock balls-deep in her shitter, she spat out another plea for him to make it hurt more.

Danny loved how tight her asshole was and how hot the inside of her ass was. Danny reached under and grabbed a big handful of Candy's big tits and squeezed and pulled them. He could feel Candy react and he knew his nut was coming soon.

"Where do you want me to shoot my cumwad, Candy?"

"Blow your wad on my face, all over me."

Danny pumped his thick cock a few more times in her tight asshole and then pulled it out all at once, making Candy almost scream as his cockhead popped out. Candy rolled over and Danny knelt next to her, jacking his rampant cock. He grunted once and then, like in his favorite porno films, thick, white ropes of his cum jetted across the woman's smiling face. It felt so good to come after all of the crazy sex play they had enjoyed. Danny pumped out a load that was big, even for him. He slumped back and breathed deeply.

Candy began to collect the cum on her face and slurp it down. Danny was wiped out.

Candy looked at him as she licked her lips, "Are you ready for more? Or do you want to call a friend to take your place?"

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AnonymousAnonymousover 1 year ago

Comment below is laughable.

A world where I can’t ram my well-lubed fully-erect penis balls-deep into a willing slut’s bowels - isn’t one that I know.

AnonymousAnonymousover 1 year ago

"Candy's asshole was very, very tight. Danny had assumed he was hurting her. He could hear her grunting from the pain."

In that case, odds are he's doing something wrong. Anal can be relatively pain-free, but that requires a fair amount of advance preparation... first you lubricate, then you dilate, then you penetrate. Get it right this time.

You still have that 6" dildo which she used on his arse, and which seemed to go in relatively pain-free. She should lubricate herself (the anus, unlike the vagina, is not self-lubricating) and use the toy on herself for a few minutes. That should push some more lube up there and stretch her out a bit. From there, go to you using the toy on her - maybe you lick her clit and pussy while you're using the toy on her butt - presumably with her face-up (supine) and her ankles vaguely behind her ears if she can get them there. From there, turn her over and replace the toy with your boy parts. Then maybe everything will fit without causing pain.

Most importantly, if anal is causing pain, stop - before the pain escalates to actual injury (which can happen easily).

AnonymousAnonymousover 1 year ago

There is some uncomfortable truth in this story

NewOldGuy77NewOldGuy77over 1 year ago

Well THAT was enjoyable and fun, but ended too abruptly! So much more to do - handcuff her, nipple clips, fucking her pussy bareback - please don’t let it just end!

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