by Holly Ardent
They sat out back and talked until full darkness fell and the fireflies were dancing around the back yard. Then Kelly took his hand and led him back upstairs.
* * *
When she stepped in the bedroom she slid the robe off to pool on the floor. Kelly turned and looked at him.
“You've got way to many clothes on for this,” she said.
Jim stripped as quickly as he could. When he was nude, she sat him down on the edge of the bed. Jim felt conspicuous for a moment with his cock sticking straight up in the air. Then he realized that Kelly had both seen it and felt it enough to be familiar with it and his embarrassment passed.
“First, the basics. If you've already been fucking someone, they may have you lubed enough to easily take their ass. They may not also, so you'll want to have some handy if you intend to do anal.”
She reached into the nightstand drawer and pulled out a tube of water based lubrication. She squeezed some into her hand and wrapped it around his cock. The lube was cold, but it warmed up quickly as she slid her hand up and down, coating him.
“How comfortable are you with giving a woman control?” she asked.
“Normally, if they want it, they get it.”
“Good. That's the safest way. Then if there are any problems, they won't blame them on you, or at least not all of them on you. Lean back on your arms.”
Jim did so.
Kelly swarmed into his lap, her knees to either side of his legs. She slowly lowered her hips down, holding his cock in place with her hand. Jim resisted the urge to thrust as he felt her ass engulf his cock. She slowed as he penetrated her, lifting herself back up several times. Finally she settled down. Jim was ecstatic. His cock was buried all the way in her ass, he hadn't had to do a thing, and she wore a satisfied smile on her face.
“This is a good way to handle women who say they're scared of anal or afraid that it will hurt too much. Give them control and once they've taken you in, I'm sure you can think of ways to take their mind off of your cock buried in their ass,” she said.
Jim lifted a hand and lightly brushed his fingers across Kelly's nipple. She shivered, the motion introducing some interesting pressure to his cock.
“Yeah, like that,” she said. “I don't want you to cum yet, but I really want to fuck you like this. Can you warn me well before you cum?”
Jim nodded.
Kelly lifted herself and slid back down his cock. She moved slowly, lifting herself until he almost slid out of her ass, then letting her weight bury him inside of her again. Her hand drifted to her pussy and started playing with herself while she rode him.
Jim stared intently at his cock as it appeared and disappeared inside of her.
I wish I could see it actually going in, he thought. Hopefully one of her positions will let me do that.
“I think you might want to stop if you don't want me to cum,” he said after a couple of minutes.
Kelly slid off of him and flipped over onto the bed. She kept playing with herself, but her other hand reached over and dragged his fingers towards her nipple. He played with it gently, using the feather light strokes she'd shown him and in a few more minutes, he got to watch her as her muscles tightened up and she had a small orgasm.
“Good,” she said, slightly out of breath, “that should hold me while we go through most of this. I'll work on another one for the finish.”
After a minute or two she sat back up.
“Okay, next position we won't go through, it's just like that, but with you lying on your back. Another good one for the timid partner. This, on the other hand, offers something for both involved.”
She got up on all fours, her ass facing him.
“Now, on your knees behind me, but don't enter me just yet.”
Jim got behind her and put his hands on her hips.
“Okay, now you've got a few choices on this one. You're in control of the penetration and you can go slow and gentle, or fast and hard, or somewhere in between. You have to decide which. In this one you can get deeper into me and if the woman enjoys anal, they'll like that. Now, thrust into me. Do it slowly first, then pull out and try fast.”
Jim pushed his cock forward. He felt her ass trying to push him back out, and despite her instructions, he couldn't help it. He let it push him most of the way out, then slid in again. He played that way for a minute or two until Kelly cleared her throat.
“As much as I love what you're doing, you're getting off the lesson plan here,” she said.
Jim sighed and thrust into her, his cock slowly burying itself in her ass. He pulled back out, all the way, then thrust forward fast and hard, drawing a gasp from Kelly.
“Go ahead and fuck me like that, fast and hard for a couple of minutes. Don't cum though,” she said, her voice hoarse with pleasure.
Jim was happy to oblige, especially when he leaned back and realized he could see his cock slide in and out of her asshole. He almost didn't stop when he started getting close, until he realized that he'd be getting a lot more of her ass if he did. He abruptly stopped and pulled out.
Kelly sighed her disappointment and sat on the bed beside him.
“Okay, missionary anal is somewhere in the middle. If the woman isn't too uptight about anal, it'll work just fine. I don't like it as much as the other positions, so we'll skip that. I'm pretty sure you've done that.”
Jim nodded.
“So, this next one is fun for me. It looks a lot like the other woman in control position, but don't try it with someone scared of anal. It'll freak them out and it hurts more than the other one. Sit on the edge of the bed again.”
Jim slid his legs over the edge of the bed and Kelly got right off of it. She stood with her back to him and slowly lowered herself down.
“Support my weight some, would you?” she asked as she lowered herself.
Jim caught her and helped her lower herself onto his cock. The position felt odd to him, it pulled his cock in directions he wasn't used to and when Kelly started rocking herself back and forth on him, he was sure this wasn't going to be one of his favorites. She stopped after a couple of minutes and stood.
“You know what? I just want my ass fucked for real. I'll tell you about a couple more positions, then I want you to pick one to fuck me in. I want to feel your cum splashing around inside my ass, then cuddle up with you and go to sleep.”
“That's fine with me,” he said.
“Okay, lying flat on my stomach is kind of like me on all fours. You'll want to use that one with partner's who enjoy a little more pain with their anal. It hurts more that way. You can also do it on your side, but it takes a lot of practice to not feel awkward that way. It's supposed to feel great for the guy and somewhere in the middle of pain and pleasure for the woman. Got all that?”
“I'll try to remember it all, but...”
Kelly bit her bottom lip and stared at him for a moment.
“Well, I've got a few days still. Maybe we can schedule another night or two of lessons. Now, tell me how you want me and fuck my ass.”
Jim didn't even have to think about it.
“Get on all fours again.”
Kelly scrambled into position.
“Can I ask why you picked this one?” she said.
“Because I can watch my cock slide in and out of your ass like this. I like that.”
She practically purred beneath him at his answer. When he thrust the head of his cock into her, he let her push him out again. This time, she didn't stop him and he kept it up until he wanted his cock buried inside of her more than he wanted to continue playing. With his next thrust he buried himself deep inside of her ass, driving through the muscle that was trying to push him back out. She let out a strangled cry and shivered beneath him.
Jim started a rhythm. Draw himself out until he could almost see the head of his cock, then slam himself all the way into her again. Throughout the whole thing he watched as his cock slid in and out of her asshole, watched it stretch to accommodate him, watch
her ass jiggle when he drove into her.
His hands reached out and started stroking her ass cheeks as he drove in and out of her. Remembering her earlier lesson, he sent one wandering up her back, stroking lightly. He hit the jackpot when he got to the nape of her neck. He buried his cock in her ass again and stroked the back of her neck.
When his fingers brushed against the skin of her neck, Kelly let out a soft cry, she tensed up, and her ass clamped down on his cock. He slid his hand up the back of her head, running his fingers through her hair. He tugged gently on it and watched as her head rose. Then he slammed into her again.
He let go of her hair, knowing that she'd ceded control to him. She wasn't trying to teach him any more, just letting him pleasure the two of them together.
His fingers danced lightly over the back of her neck as he pounded her ass. When he was sure she was cumming again, he sped up even more. He was close, knew it, and wanted to cum right along with her.
His hands went to her hips and he yanked her back towards him, driving his cock into her ass at the same time.
“I'm cumming,” he called out.
She shuddered beneath him, her ass clamping down even harder. He held himself all the way inside her ass as his cum spurted from his cock.
“Oh god, fill me up with your hot cum!” she cried, loud enough that the neighbors could probably hear.
Jim tried to thrust even deeper, but he was already as far in as he could get. His cock twitched and spat as her ass clenched down on it again and again. Her ass was still gripping him when he finished cumming and it didn't stop until he started going limp inside of her. He slid out and flopped on the bed beside her.
Kelly collapsed onto her stomach, her limbs sprawled out to the sides. She was panting and when she first tried to speak, she had to stop and wait a while before she had enough breath to do so.
“I think... you've got... the basics down,” she said.
“Would you believe I had a good teacher?” Jim asked.
It was a minute or so before she replied.
“Maybe, we'll find out in the more advanced lesson. Tomorrow night at eight o'clock?”
“Count on it.”
Jim helped her get beneath the covers, then joined her there. The two of them fell asleep in a tangle of limbs.
* * *
Hannah's Basement
(Cuckold MILF Erotica)
MILF Money for College #6
Holly Ardent
Text copyright © 2015, Holly Ardent
All Rights Reserved
Jim Riley was feeling conflicted. On the one hand he was looking forward to returning to college. On the other hand, this summer had been the best time of his life. He was making good money and not having to spend anything other than the token rent he'd decided to pay his parents. He'd had more sex this summer than in the rest of his life combined and with women he never would've thought were interested.
His next door neighbor Lisa had started it all. Her daughter had moved out and her husband was gone all the time so after Jim had done some work for her, she invited him in for some play as well. Over the course of the summer, there wasn't a position he could think of that they hadn't tried. She was game for just about anything he could think of and she'd thought of a few things herself that Jim never would've dreamed up. Add in the fact that she'd arranged for him to have sex with a few of her friends as well and Jim was in seventh heaven.
The last friend she'd loaned him to taught him a few new things. Over the past week, Lisa had been very appreciative of what he'd learned. But now, after having some really awesome sex, she was looking at him oddly.
“What's up?” Jim asked. “You're looking at me strangely.”
“Sorry, just wondering if you're up for something,” Lisa said.
“Well, not at the moment, but give me a few minutes.”
“Not that. I meant something else. It has to do with sex, but a lot more than just that. And not with me either.”
“I certainly haven't been disappointed with any of your friends you loaned me to if it's something like that.”
“Yes, and no. It isn't you I'm worried about being disappointed, it's them.”
“Them? As in, more than one?” he asked.
She nodded.
“Not like you're thinking though. Let me lay it out for you, but I'm not going to use any names yet.”
“Okay, hit me.”
“I have a married friend. She wants to do some kinky shit with her husband. Neither of them has any experience with something like that. Because of the lack of experience, she's scared to ask him to do it. She doesn't know what to expect and even walking her through it verbally didn't help.”
“So, you think I might be able to give her a taste of it first?”
“Kind of, but I'm not done yet. You see, I talked to her husband about it and he thoroughly approves, but he won't bring it up to her unless she brings it up to him first.”
“So how does that involve me?”
“He suggested that I enlist the aid of a certain young man, that he's heard some rumors about, to break his wife in to the idea. Yes, I mean by doing it with her. Dominating her and a couple of other things that I know you like. But...”
Shit, there's rumors going around about me? Maybe it's a good thing I'm going back to college in a week, Jim thought.
“Okay, I can do that. I can't believe the guy actually asked for someone to fuck his wife and dominate her, but I can kind of understand not wanting to try it himself and maybe screw up his relationship.”
“There's just one more catch,” Lisa said. “He also wants to make a video of it. He's even set up a batch of cameras in all the basement rooms to record it since he assumes that I'll come through for him.”
“Wait, so he wants a video of me fucking his wife? Are you sure he's not trying to divorce her or something? I'd hate to get involved in something like that.”
“No, I know these two pretty well. They aren't ever going to get divorced unless I'm reading them totally wrong. He gave me a whole list of reasons why he wanted the video though. He's sure things won't go too far if he has the video, he wants to show it to his wife after to prove that he knew about it all along, he wants to see what you do with her that works so he can learn from it, and he said he thinks he'll get off on watching some stranger dominate and fuck his wife.”
“That's... strange,” Jim said. “Let me think about it for a little bit.”
“If it's any help, this offer came up and it's one of the reasons I asked Kelly to teach you what she did. If you accept the offer, you can use what she taught you on Ha... this woman. You can give her so much pleasure that she won't notice you sliding into her ass until after you're in there. That's something she specifically wants done, because her husband has asked for anal and she turned him down. She wants to be able to give it to him, but also wants to try it with someone else first, just in case.”
“Are you absolutely sure this guy is for real? He isn't going to lose it if I fuck his wife?”
“Not this guy, he's not the type. Although I can see him dominating her and both of them being happier for it.”
“Well, like I said. Let me think about it for a bit.”
“Don't take too long. You're going back to college in a week and this is a limited time offer. You're sure you can handle the domination part, right?”
“I think so, but you can ask Pam if you have any doubts,” Jim said
“Oh, I did. I just wanted to make sure you were confident of it.”
“Yeah, if I do it, I can handle that part. If I give you my answer tomorrow morning, is that soon enough?”
“That will do. Now, you were saying you might be up for something in a few minutes? Has it been long enough?”
Lisa reached out and when her fingers touched Jim's cock it stirred and started to stand upright. She smiled and went to her knees in front of him, her lips engulfing his cock.
* * *
“I'll do it,” Jim to
ld Lisa.
“Are you sure?”
He nodded.
“I figure it'll be a lot of fun and if things get too hot I can always use some of the money I earned this summer to take a hotel room near college for the last few days before classes start. I'd hate to miss out on those last few days with you, but...”
He shrugged.
“Okay, I'll call and set it up later on today. But it won't be for a few more days, just in case you feel the need to skip town after. I'll treat these next few days like they're our last for this summer and if we get the others as well? I'll have to see if we can outdo ourselves during our bonus time.”
She shot him a wicked grin.
“But for now, how about you practice some domination on me?”
Jim eyed her eagerly.
“Strip, then get down on all fours,” he said.
Lisa's grin widened as she started taking off her clothes.
* * *
“It's all set up,” Lisa said. “You'll be doing it three days before you go back to college. Her name is Hannah and here's the address. If anyone asks, you're helping finish their basement.”
Lisa handed him a scrap of paper. He glanced at it and recognized the street name.
“Got it,” he said. “So, I can do the domination thing, if she cooperates, but do they want any gear type of stuff? Pam had this thing with handcuffs and some eye bolts.”
“If you want to use something like that, I'm sure they wouldn't mind. But that will be up to you. Like I said, I'm worried about disappointing them, so maybe just have something with you that you can use if you feel the need?”
Jim thought for a moment.
“No problem. Handcuffs aren't cheap, but eye bolts are. So are zip ties. I'll think of something.”
“Good, but think of it later on. Right now, I want you thinking about me,” Lisa said.
* * *
The days passed quickly. He only worked one paying job this week, and that one was for Lisa herself.
I bet she put the word out that I wasn't available for any more work. Not that I'm gonna complain. Lisa knows how to wear a guy out and if I had to work also, I wouldn't do justice to either the jobs or Lisa.
