The Divorcee and the Yard Boy Ch. 16

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Stan tries to blackmail her. It doesn’t quite work that way.
13.8k words
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Part 16 of the 17 part series

Updated 06/09/2023
Created 05/06/2009
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Gloria's back arched slightly as she neared climax. her blouse was unbuttoned so she could feel up her 36C breasts. She had long ago peeled off her panties, tossed them by the couch, and hiked up her skirt so her other hand could work her shaved pussy. She was close. Sweat beaded on her forehead at the edge of her soft black curly hair.

Then the doorbell rang. Fuck! Not again! Whatever. She'd ignore it. She kept rubbing herself. Who could it even be? No. Focus.

Then whoever it was started knocking, an insistent rap. Was it the delivery guy again? Had he forgotten something? He had left pretty quickly ten minutes ago.

It wasn't how she had planned to spend the day. It had started with a Saturday brunch date with a guy she met online. The website focused on getting people into long-term relationships, but plenty of guys on it were also open to more casual flings. Midway through brunch, her date got an urgent call. He apologized, and she politely played it cool as he took it. As she listened, she could tell what was happening. Sure enough. Big demo for a key investor coming up unexpectedly. All hands on deck, especially the founder. Did he have to go in right away, she had asked, folding her arms so she could push up her tits and reveal they were naked under her blouse. He had sighed and asked for a rain check. She had made polite noises, but she was young and her profile pic was her in a skimpy bikini. There was a line of suitors out the virtual door. He had been decent enough to pay for brunch, at least.

But she had gotten herself excited beforehand and lay down on her living room couch to get herself off when she got home. She had envisioned her date fondling her as she caressed her breast under her blouse and slowly lifted her skirt. She had been nice and warmed up when the doorbell rang, startling her. The delivery person had been halfway to their truck by the time she opened her door. All that for some new water glasses she had ordered.

She had grumbled, sighed, and returned to the couch. She had gotten herself comfortable again, slowly unbuttoned her blouse, pulled her panties off, and gone to work.

The knocks paused and restarted. God damn it.

"Hold on!" She stood up, straightened her skirt, and did up some buttons on her blouse. She stomped to the door, flung open the door, and growled out an unwelcoming "What is it?"

"Hey, Gloria," said the young man standing there. "It's been a while."

It took her a moment. And then she remembered. About a year and a half ago, she had offered herself as a sex slave to her yard boy and his friend for the summer. Usually they fucked her by themselves. Sometimes they brought friends. Including the young man who, by coincidence, shared a section of her back fence.

"Stan?"

"I'm touched you remember me. I sure remember you." His eyes slid down her body, and she glanced down as well. She hadn't done up as many buttons as she thought, and she hadn't lined up the buttons with the right buttonholes. That was a noticeable amount of cleavage.

"Yeah, sure. Why are you here?"

He held up a manila folder that had been at his side.

"I think we should talk inside. It's a little private."

She threw up her hands. "Ugh. Fine!" She waved him in and then closed and locked the door behind him.

By the time she got to the dining room, there were some pictures on the table and he was laying out more.

"What the fuck?!" she shouted as she glanced down and saw herself sunbathing in the nude. Taking a guy on all fours. Stan was just laying down one of her sucking a guy's dick. "You've been spying on me?!"

He held up his hands. "I was taking nature pictures for a class I'm in. You happened to be in frame." She looked at him skeptically.

"Okay, you're a peeping tom. Yay for you."

"I asked myself what would happen if I sent these to your boss. Or other people."

She cocked her head. And then laughed. He looked confused. He wouldn't know.

"If you send them to my boss, he'll probably just add them to his collection." Stan's brow furrowed. "He found amateur porn of me and has held it over me ever since. Just yesterday he requested a TGIF party with him and a senior partner." She pointed to the picture of her on all fours. "It was like that, but with two guys and on his desk. Oh, and I kept my high heels on." He frowned.

"Oh my god. Were you going to blackmail me?" He glumly nodded, and she burst out laughing. "That's so cute!" He grimaced.

"So now I want to know. What happens if I tell your dad about this nature photography?"

At this Stan smiled. "He saw the first batch and bought me a zoom lens."

She frowned. "And what about your mom?"

Stan grimaced again. "They split a few months back. She's living in Southern California now."

"Aw, I'm sorry. That sucks." She was divorced, but there were no kids involved, thank god.

He shrugged. "It was dad's fault. He was practically flaunting his mistresses at her." She briefly wondered what his dad was like in bed. She brushed the thought away.

She was about to send him packing when she paused. She was horny as fuck, and Stan was a good lay. A decent enough dick, but he had great stamina and when he came it was like a faucet of spunk. Hmm.

"So what was going to be the price for these pictures?" Like she didn't know. He had the good grace to look embarrassed.

"Sex."

She gasped and put her hand to her mouth. "I'm so shocked."

"Yeah, yeah."

"But just sex?"

He shuffled his feet and looked at the ceiling. "Fine. I was going to make you do whatever I wanted."

"My word!" she said with more faux shock. "And that was going to include sex?" He nodded. "I'm guessing not just once?" He shook his head.

"Well, we seem to be at a stalemate, then." He glumly nodded. "But I have to wonder. Why not just come over and ask for sex?"

He blinked in surprise. "I guess I figured you'd say no."

"Well, that's possible. But I might have said yes, and you could have saved yourself how many months of work?"

Now he looked sheepish. "Uh, a few."

"I mean, you could've asked and if I said no move to this ridiculous plan. It never hurts to ask, right?"

"I guess not. I just. I just really wanted to make sure you said yes."

She paused. Then she put her hands behind her back and began to gently sway back and forth. Yes, this was a good plan.

"Ahem. It never hurts to ask, right?" She raised her eyebrows.

"Uh, no. Right. Do you want to have sex?"

"Hmm, I could be persuaded." His eyes widened, and she nodded. "But not just whatever you want. You'll have to earn whatever depraved acts you're imagining. Because I suppose you're imagining a few." She was actually tempted to just do the sex slave thing for the day. Seeing what guys did when uninhibited was a lot of fun. But no reason to not get things she wanted, too.

"Um, yeah. Okay." He nodded.

She laughed. "I figured you'd be okay with that." She stepped forward and put her hand on his muscular chest. "After all, you're still going to get that dick where you want it." He grinned.

"So what horrible deed would I have had to do first?"

"Uh, a blow job."

She sighed. "Okay, look, Stan. We've fucked a bit. I wouldn't say we're super intimate, but I know you have specific ideas in mind. The more honest you are about those ideas, the more likely you are to get what you want. Got it?" He nodded. "So let's try that again. Pretend for a moment that your little scheme worked."

He took a breath. She felt his muscles ripple under his shirt. "I want you to strip down to your underwear, get down on your knees, and suck my dick until I cum in your mouth. And I want you to swallow every drop."

"Mmm. A good start. Classic." Then she thought about what he'd said. "You don't want me to strip naked?"

He grinned. "Not yet."

"Hm"

"I figured you've got some hot lingerie action going on, and if you kept wearing that, it would be like face fucking a Victoria's Secret model."

She laughed gently. "I appreciate the comparison. But I'm afraid I can't give you exactly that." He looked disappointed. She grabbed his hands and put them to the topmost buttoned button on her blouse. "Why don't you undo that one for me?" His fingers eagerly maneuvered the small disc. She pulled the blouse open, revealing the tops of her nipples. "You see the problem?" His gaze turned wolfish as he saw her mostly bare breasts.

"You're not wearing a bra?"

"Why don't you give me a kiss." He leaned down, and she parted her lips. His tongue slid into her mouth and she moaned. A very good idea. She took one of his hands and slid it into her blouse on to her naked tit. He kneaded it and squeezed. She pulled away from the kiss. "Seems like you were right!" She stepped back. "Maybe you should attend to these other buttons."

"I definitely envisioned you unbuttoning your blouse and taking it off while I watched, though."

She slowly undid the last two buttons, and shrugged the blouse off. She was topless. "See? Asking for what you want is a good approach. Now let's get another kiss." He eagerly leaned forward and kissed her again, his hands wandering over her naked chest, thrilling her with his aggressive touch. Though, in her state, anything would be thrilling her now.

He broke his kiss. "That was lovely," she said. "But that's not where I meant for your kiss to land." She pulled his head down to her naked breast, and his lips locked around her nipple. "Oh, yes," she sighed.

She soaked in the feeling of his eager mouth sucking her tit into it. She felt a hand slide down her back and onto her ass. He grabbed a cheek hard and pulled her body even closer.

She was panting in pleasure, but she pulled back. She grabbed the hand on her ass and maneuvered it between her legs. She held his wrist and gently moved it up and down her thigh, under her skirt but not to her pussy. Not yet.

"Look by the couch and tell me what you see." She saw his eyes move off her body and over her shoulder. Then he saw it. She could tell. His eyes stopped and he began to grin. "Turns out I'm wearing matching bra and panties after all." His hand began to move but she held it firm.

"Now let me ask you this," she cooed. "Woman comes to the door looking disheveled and her panties are on the floor by the couch. What was she doing?"

He looked down at her. "Getting herself off."

"Mm hmm. But she didn't finish because someone interrupted her with his dumb scheme." He looked sheepish. She liked this less-of-an-asshole Stan. "So here's what's going to happen. I'm going to let go of this hand, and you're going to get me off with it. Right as I stand here." She stood on her tiptoes and kissed him. "And then I'm going to take off my skirt, get down on my knees, and suck your dick so hard I hope I leave a bruise. And you're going to unload into my mouth. No. My eager mouth. My hungry-for-your-cum mouth. Sound good?"

"Oh, hell, yes." She let go of his hand and spread her legs a little. Instantly his hand sped up to her naked cunt. He stroked the outside for a moment but then slid a finger in. "Damn you're wet."

"Well, I was pretty close to cumming before you knocked. But I can barely feel that finger." He slid his mouth back down to her naked tits and then pushed in another finger. And another. "Keep going," she panted. He slid in the fourth finger. And then his thumb began to rub her clit. "Oh, god, yes. Right there."

She had been so close for so long. She barely lasted a minute as he stroked her. She let out a loud animal moan as she finally came. Her pussy clenched against his hand, and she could feel her juices sliding down her leg. It didn't matter. She came again. She had held herself back so long that she was like a flood of orgasm.

"Give me a moment," she panted as she leaned against him. He stroked her hair and shoulders and back as she slowly recovered.

"Better?"

"Oh very much so."

He leaned forward to whisper in her ear. "Then take it all off, baby."

She smiled, stepped back, and reached behind her to undo the skirt's buttons. She felt the waist relax and then wiggled it over hips and down her legs.

"God, I love your body," he said. She slowly turned so he could see her in all her nude glory. He stepped towards her as her back was to him. She arched her neck back as his hands caressed her naked body.

"I hope you're intending to fuck me like this," she said as his hands wandered over her tits and between her legs. "And maybe not in the pussy." She pushed her naked ass back against the hard cock pressed against his jeans. He slowly turned her to face him.

"Oh, I have a lot of plans," he said. Then he put his hands on her shoulders and gently applied pressure. She knelt down and kept her eyes locked on him.

"Why are you still wearing that shirt?" she asked. He began to lift it up, and she began to work on the buttons of his jeans. She yanked them and his underwear down to his knees in one swift motion. His 6" cock popped into view, rock hard and pointed straight at her face. She put her hands around his naked ass, opened her mouth, and dove onto his cock, using her hands to pull him even farther into her mouth. Like promised, she sucked. Hard. He groaned.

She kept his dick in her mouth as she pulled back and then sucked again to pull herself forward. Her lips hit his stomach and she rolled her tongue along the hard pole in her mouth. She did that a few more times and then popped it out so she could lick it up and down. She kept her eyes turned up to his face; the grin on his face as he watched her pleasure him almost made her cum again. Guys watching her as she had sex was a big turn-on.

"I love looking down and seeing those big tits," he said while panting. She placed her hands on her breasts and lifted them. "Oh, yeah," he moaned.

She lost track of time as her lips and tongue worked him over. But then she felt him harden even more, and his hands cupped her head. She groaned as he thrust his dick into her, pulled back, and thrust again. Thrust. Thrust. Thrust. Faster and faster.

And then with a shout he pulled her head all the way down his shaft and began to cum. She gagged as her mouth filled, and she did her best to swallow it as it came. But the sheer volume -- plus the fact that her mouth was full -- overwhelmed her, and it began leaking out the sides. She felt some drip down her chin and onto her chest.

With a final shudder, his orgasm finished.

"Fuck. Yes!" he shouted. "That felt so fucking good."

"I guess so," she said as she leaned back and let him take a good luck at the cum sliding along her face. She scooped some up with her finger and slid it into her mouth.

"So what other naughtiness did you have in mind?" He paused. "How often am I going to have to give the honesty speech?"

He raised his hands in surrender. "Okay, okay. Well, I pictured you still in your underwear, so I figured you'd have to take me to your bedroom, do a strip tease with what was left of your clothes and then get me hard again. I was going to leave the how up to you, but strongly suggest your tits."

She was getting fired up again. This was so hot. What would it really cost to just be his sex toy for the day?

"Tits are an excellent idea," she said with a grin. "And then?"

"Climb up on top of my dick and ride me."

"That sounds lovely," She stood up and took his hand. "But first you're going to lick my pussy until I cum."

"Sure thing," he said. Eagerly, even.

"I like this new version of you," she said as she raised an eyebrow.

He looked to the side. "Yeah,okay. I was an asshole about that, I remember."

"So what changed?"

"Met a girl," he said. "We started to fuck and she said if I wanted her to get her freak on, I'd eat her pussy and she'd be putty in my hands. So I did and she did."

"Ooh, like what?"

"Started out as oral and anal. Then a threesome with her roommate. Then a foursome with my roommates. Then her tied up with me and a friend of mine."

"Mmm. Sounds like a keeper."

He shrugged. "She said she wanted to try out other guys."

She put her hand to his cheek. "Aw, I'm sorry, Stan." Then she grabbed his hand. "C'mon. I have an idea." She led him to her bedroom. "I have an idea for a bit of a strip tease. How about we do that, then you go down on me, and then I get you hard and ride your dick?"

"How can I say no to that?"

"You lie down on the bed, and I'll get ready."

He did as she asked, his right hand near his cock while he put his left arm behind his head. Damn, he was tight. Maybe just do the sex slave thing, after all, she thought. Hm, maybe not yet.

She took a breath and then walked into her large closet, full of her clothes, lingerie, and some outfits. She found the costume she wanted and then dug around for the best underwear.

She peeked her head around the corner of the door. "No peeking!" He closed his eyes. "Promise?"

"Promise."

She quickly scooted into the bathroom. Had he peeked? Who cared, really? She got dressed and took a moment to tidy up her hair and makeup.

She peeked her head around the door. He looked at her expectantly from her bed.

She opened the door wide and stepped into the room. She was wearing her cheerleader roleplay outfit. The blue sweater with gold trim hugged her breasts, and the matching flared skirt barely went past her crotch. His eyes popped.

She wiggled the pom-poms and leaned against the doorframe.

"Oops," she said in a sultry voice. "I wandered into the wrong locker room."

He sat up. "I'll say," he said. "Coming into your big school rivals' side?" Hm, not what she expected, but she could go with it.

"I was hoping to make some friends," she said, lightly swaying back and forth. "But can a quarterback and the head cheerleader for the other team ever be friends?"

"Depends. What do you want in a friend?"

"The girls on my team are all so shallow, you know? I like meeting boys because they can get to know me so deeply. I like things deep." She ran her hands down her chest to her skirt and lifted the hem ever so slightly.

"I want to be friends with you," he said. She looked pointedly at his dick.

"Oh, I'm so happy to hear that." She gave a little squeal and hopped up and down. "Do you want to see some of our cheers? I could use some tips from a friend." She planned to steer this the way she wanted.

"Sure," he said with a grin. "That's what friends are for."

She shook her pom-poms, leaned forward a bit, and began to swing her hips. "Hey hey! Aw shucks! Your team really truly sucks." She leaped and turned around. "When our boys win, they'll be good fucks!" And she bent forward so that her skirt lifted up and wiggled her ass. "Go team!" She reached behind her and shook the pom-poms in front of her ass.

He clapped. She stood, turned to face him, and did another. "3 4 5 6. You all have tiny dicks!"

"I guess now that I think about it, those are a bit mean," she said. "Hard to be friends if I'm saying stuff like that."

"You're just saying it to taunt us. I get that."

She stepped forward. "I don't think we can be friends until I make amends." She bent over and rested her elbows on the bed, her hands still holding the pom-poms, and looked at him. "I should let you punish me."

There was no confusion about what she meant. Her ass was up in the air, and her short skirt had ridden up her body.

He stood up with a lustful, hungry look. "Now that you mention it, that would probably help get us past this awkward part."

"Oh, good! I want to be friends, and I don't want you feeling resentful." She wiggled her ass, and he stepped behind her. She felt a whoosh as he flung her skirt up. He now had a full view of the lilac cotton bikini panties she had on.

There was a pause. She held her breath. And then. SMACK! His hand came down hard on her ass. She yelped. SMACK! She yelped again. A few more smacks landed. Then he leaned his naked body down over her and put his mouth to her ear.