Between Her Thighs

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A young man thinks he can seduce an older woman.
1.7k words
4.49
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Riley learned early in life that he was lazy. He always took the easy way to do anything, despite the efforts of his parents to guide him. As an only child, he had been spoiled from day one. At 20 years old, he was still living at home and his only source of income was from delivering pizzas.

Although he was of average height and weight, Riley possessed something that overshadowed his lack of enthusiasm, and that was charm and boldness. He had pushed his way into many relationships with girls, took what he wanted physically and then moved on to his next opportunity.

He was sent out to deliver four pizzas one afternoon, and the last one was to a house in his neighborhood that had been unoccupied for almost six months. He rationalized that someone new there was probably ordering pizza for convenience while moving in.

The woman who answered the door surprised him. She was much older than he and she wore a cut off tee shirt and denim shorts. Her breasts stood out so boldly that the nipples showed through the fabric. She had thick thighs but narrow hips.

Her brown hair was pulled back into a ponytail.

She smiled and said, "Oh, that was fast; I was just getting ready to work out."

Riley handed her the pizza. "Hi, I'm Riley."

"I'm Valerie, but people call me Val; come on in."

"Nice to meet you, Val. That will be $22.75 plus my generous tip."

Valerie set the pizza on a table nearby and grabbed her purse. She fumbled around in it, digging for money and finally looked up in frustration.

"Looks like I only have about $7, do you take American Express?"

"Nope, sorry," Riley lied. This was going to be one of his special deliveries.

"MasterCard, Visa, Discover?" she asked.

"Sorry, Ma'am, they don't allow me to carry a swiping device; cash only."

Riley had a stupid knowing grin on his face, and Valerie knew his game.

"What about a personal check?"

"Sorry, ma'am, we've had problems with checks, so, cash only."

"They didn't tell me that when I ordered," Valerie protested.

"Everybody in town knows it, so they don't usually have to say it."

"Well, Riley, why don't you give me your home address, and I'll bring you the money later today?"

"No can do, ma'am, I have to turn in the money before I clock out today."

"And may I ask, what do you do in a situation like this, Riley?"

"Well, usually I can work out something with the person who ordered."

Valerie could tell by the way he had looked at her chest and her legs that he was conjuring up a "solution" in his mind as soon as he knew that she did not have the cash.

"Alright, what do you have in mind here, Riley?"

"I'd like to see your tits, have you sit on my face and then fuck you," he said boldly.

"For $22.75? You're out of your horny little mind. How about if I let you see and squeeze my tits and we'll call it even?" She offered. "And you keep your mouth shut about it?"

"How about if I tell my boss and my parents that you offered to suck my dick if I would let you have the pizza for free?"

"You're a mean horny little bastard, aren't you?"

"Yes ma'am, but I DO know how to keep a secret."

Much to her dismay, Valerie lifted her tee shirt and let him see her perfect breasts. He stared at her hard nipples, licked his lips and reached for them.

"Damn! You might be as old as my Mom, but you've got great tits!"

"I'm not old enough to be your mom, I'm only 35!" Valerie shouted. "And you can't touch them."

"Okay, okay, but will you sit on my face now, just for a little bit?"

"I suppose you expect me to do it naked, don't you?"

"Oh, yeah, the girls I've been with said I'm pretty good at it; I listen to their advice."

"Jeez, let's get this over with," Valerie said with a sigh.

She led him into her bedroom where there were still a few taped up boxes around the room. The bed had sheets on it but the bed was unmade. Without being told, Riley got onto the bed fully clothed and flopped on his back. Valerie wiggled out of her shorts and her thong.

"Hey, can I have your thong for my tip?" Riled asked.

"No, and if you don't make me come, you dirty little fucker, I'll make you eat my ass."

"Oh, shit, you're gonna give me a boner, lady."

Valerie didn't want to look down at him, so she straddled his head facing his feet. He wrapped his arms around her legs and went to work with his tongue. Valerie was impressed at how good he was, starting slowly, teasing before licking at her clit. One of the reasons that she let him do this was because she was lonely and had not had sex for several weeks.

Riley was enjoying himself, proud of the fact that she was leaking juices, which meant he was doing a good job. When Valerie began moving back and forth across his mouth, Riley's dick got hard, and Valerie noticed it. She leaned forward enough to rub the bulge in his pants.

Riley moaned and licked faster. Valerie unzipped his pants and Riley reached down to pull out his erection, thinking that she would do something with it. She didn't. She decided to tease him and let the little bastard suffer.

Riley's dick throbbed and weaved back and forth in front of her and Valerie finally let herself come, pressing her wet pussy against his sucking lips. His dick was dripping precum, which made her smile. She sat still on his face for a few minutes, enjoying the last of her climax.

When she got up off of Riley's face, he undid his belt and took off his pants and boxers. His face was wet and shiny and he was panting with need.

"Okay, let's fuck!" He gasped.

Valerie looked at him with a mournful smile. "Oh, we can't actually fuck," she said.

"What? Why not?"

"Well, actually, Riley, I'm a lesbian, so I don't do dicks."

"Well, you agreed to fuck me, so you have to," he argued, grabbing his dick.

"Oh, I'll fuck you, but not the way you wanted," she answered.

"What?"

"Just lie down on your back, hands over your head and let me take care of you."

When Riley was in position, Valerie laid on top of him, her nipples pressed into his shirt, her face just above his. She let his erection slip between her soft thick thighs, not touching her pussy. She pressed her legs together and suddenly his dick was squeezed between them.

On her elbows, Valerie looked down at Riley's surprised face, and she began to slowly lift her body up and down, fucking his erection with her thighs.

"Can you feel your dick between my legs, Riley?" She asked with a soft voice.

"Yes, ma'am," he said, still highly aroused.

"it's not like fucking a pussy, is it?"

"No, ma'am," he gulped.

"But it does feel good, doesn't it, Riley?"

"Fuck, yeah!" he said, his eyes open wide.

Valerie could feel him lifting his hips, trying to fuck her thighs. She kissed him softly on his lips and whispered, her lips lightly brushing across his.

"Shh...don't move, let me fuck you with my legs. You like my legs, don't you, Riley?"

"Um, yes ma'am," he moaned.

Valerie could feel his precum on the insides of her thighs. She wanted to make this horny bastard suffer for blackmailing her.

"I liked you eating my pussy," she said, kissing his left ear. "Can you imagine how hot i would be if you ate my ass, Riley?"

Riley groaned and she humped up and down on his dick a little faster. Her inner thighs were soaked with precum, and she was getting even wetter from teasing him.

"Imagine how tight my asshole would be on your tongue, Riley," she said, kissing his right ear. "It would be even tighter with your dick in my ass."

Riley moaned, his eyes closed. His hands were still above his head but fisted.

"With your eyes closed like that, just pretend you're fucking my ass, Riley," she cooed. "Does your dick feel good in my ass?"

"Oh, God, oh, I'm getting close..." he moaned.

Valerie squeezed her thighs together as tightly as she could, teasing the tip of his erection, and she humped him fast, so the head of his dick slipped in and out of her thighs.

"Come in my ass, Riley, fuck it, fuck it HARD, Riley!"

"OHHH, AUGHH, ma'am, shit...SHIT!!" he groaned.

His sperm splashed all over her thighs and her ass as he lifted up, fucking her thighs for all he was worth. She let him finish, watching the agony and the ecstasy wash over his face. It turned her on. This was certainly not something she had planned, but the thrill of teasing and controlling him was something she had not experienced before. She thought to herself, "Maybe I should order pizza more often."

Valerie laid on top of him until Riley calmed down and his dick had shriveled up and slipped out of the grasp of her thighs. He laid on the bed gasping for several minutes even after she had rolled off of him.

Valerie went to the bathroom and cleaned up and put her shorts back on. As Riley was getting dressed, Valerie handed him her thong.

"Here; you can have these as a souvenir under two conditions," she said.

Riley took them, smiling. "Sure!"

"One, you have to wrap them around your dick every time you masturbate, and two, you have to bring them back to me with a free pizza and I want to see plenty of your dried cum on them."

Riley grinned. "Absolutely, and I'll make sure nobody else delivers your pizza's; I don't want anybody else to know how fucking cool you are."

As Riley was leaving, Valerie asked him, "Say, do you have any girls who deliver pizza's?"

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paulapossiterpaulapossiter3 months ago

Hi Will, love your little vignettes. Keep it up ( so to speak). Paula💋💋

Cunning_Linguist_69Cunning_Linguist_697 months ago

Hot story. Loved it.

I'd love to read a follow-on with a gal delivering... or Riley brings a friend

Cunning_Linguist_69Cunning_Linguist_697 months ago

Love when lesbians push boundaries

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