The MILF Man Deliveries Series- Complete Set

by Holly Ardent

  Erin looked thoughtful for a moment.

  “I think I can do that,” she said, surprise evident in her tone.

  Nate leaned in, his gaze focused on her.

  “I'd really like it if you could,” he said. “Meanwhile, since Jack got you to do it already, I think you ought to reward him.”

  She cocked an eyebrow at her husband.

  “Put yourself on top, give him everything you've got, if he wants it,” Nate said.

  Erin blushed, but gestured for Jack to lie down again. This time she crawled up on top of him and lowered herself onto his cock. As she settled down, he heard her mumbling to herself.

  “That's so nice, fills me up, stretches me just a little bit. I'm so full with that there.”

  Jack realized that she was trying what he'd recommended. He also realized that if there were much going on, he wouldn't be able to hear her at all. He considered asking her to talk louder, but didn't want to interrupt her efforts.

  Nate didn't have that problem.

  “Louder Erin, I love hearing you like that,” he said.

  She blushed again. With her fair skin tone there was no hiding it, but her voice grew louder.

  “I just want to sit like this for a minute. Then I'm going to lift myself up and just let my body drop. It'll feel so nice to get pounded with me in control.”

  True to her word, she paused and then lifted herself up and let herself drop back onto Jack's cock. She landed hard enough that it sounded like a smack. Then she did it again, and again. Before long, she tensed. Jack reached up and grabbed her breasts. He squeezed them tightly before moving his attention to her nipples. Those he pinched and tugged on. Erin let herself drop again and arched her back. One of her hands moved down to her clit and moments later she was cumming again. She managed to speak through her orgasm.

  “Oh god, I feel like I'm losing my mind. Fucking my brains out never sounded so good. I hope Jack and Nate are enjoying this as much as I am.”

  Jack heard Nate stand up and push the chair back. He wasn't willing to turn and look to see what Nate was doing since he was watching Erin's breasts jiggle and bounce as she came. When she finally stilled, Nate spoke forcefully.

  “Erin, lift yourself off of him and turn around to face his feet. Lower yourself onto him again then, with his cock in your ass. Then lean back a little.”

  Erin blinked several times, apparently trying to comprehend Nate's order. Then she did as she was told. As she lowered herself onto him, Jack felt her tight ass slowly expand to accommodate him. The feeling was delectable and he tried to hold himself still in an effort not to disrupt it.

  When Erin leaned back, he bit his tongue to stay silent. He could feel his cock pushing on the inside of her ass, touching places inside her that he'd never touched in a woman before. A moment later the bed shifted slightly and Jack found out the reason for Nate's request.

  Erin gasped as Nate began to push himself into her pussy.

  “Oh my god, oh my god, I'm going to explode. I'm so full, and Nate's only barely in me yet. Two massive cocks are going to fill me and I'll explode and there'll be nothing left.”

  Jack felt it as Nate slid his cock into Erin's pussy. There was only Erin's flesh between the two of them. He'd worried that if this happened, he might get freaked out, but the silken feel of Erin's ass wrapped around his cock. The only thing he felt from Nate was the additional pressure his entry caused.

  When Nate finished pushing himself into Erin, he grabbed her around the waist. Jack saw the upper portion of his fingers wrap around her sides when he did. Nate leaned Erin back towards him slightly and then lifted her up and lowered her. Jack gasped, Nate sighed, and Erin kept talking.

  “I'm just a toy, I'm just their sex toy that they're playing with. Oh how lucky I am. Fill me, fuck me, cum in me. I'll explode and there will be nothing left.”

  Nate began to lift and lower her with the regularity of a man doing curls in a workout. Jack just focused on trying not to cum. Erin didn't and she was writhing, moaning, and screaming in under a minute. Nate didn't let that bother him, he kept lifting her up and down. If anything, her orgasm made him speed up.

  “I can't hold out much longer,” Jack said.

  “Please, don't. Don't hold out. Fill my ass with your cum!” Erin screamed.

  Nate plunged Erin down onto their cocks and started moving her waist around in circles. Jack's cock, inside of Erin's ass, started rotating along with her. It was too much, he started spurting into her, setting off another orgasm for Erin, or possibly just continuing the one she'd started minutes earlier.

  Jack laid there as Nate pushed Erin down onto his torso. Then Nate started hammering his wife, the sound of flesh on flesh echoing through the room as he pounded her as fast as he could. She was still orgasming but Nate held her steady, keeping her positioned correctly for his cock.

  “Fuck me and fill me!” Erin screamed at Nate.

  Even having just cum, Jack felt his cock stirring again, trying to get hard. The press of Erin's flesh against him, her hair that surrounded his head, and her constant writhing were filling his mind with the thought of pounding her some more. The motion of the bed stopped and Jack glanced up. Erin was rigid on top of him now and Nate was cumming in her pussy. Jack could feel it through the flesh that separated the two men's cocks.

  * * *

  Erin collapsed bonelessly on top of Jack. Nate managed to pull himself up so he didn't sprawl on top of the two of them. It was minutes before either Jack or Erin could move and when they did, his cock finally slid out of her ass. After that Jack recovered quickly. He'd been able to feel the twitches running through Erin while he was still in her, now he just felt the cool air of the bedroom and the warmth of her skin.

  Erin eventually rolled over, off of Jack. Now she was lying between Jack and Nathan, who was back in his chair.

  “Nate, what happened? You haven't managed to suddenly get hard in years,” she said.

  He grinned at her.

  “Thank Jack, when you started talking dirty for real, it was like someone flipped a switch.”

  “Thank you Jack,” Erin said. “I really mean it, thank you so much.”

  “Don't go overboard,” Nate said. “We don't know if that will work all the time yet or not. I'm pretty sure that will do it for a while though.”

  “You're welcome,” Jack said. “Please believe me when I say it was my pleasure.”

  “I was there,” Erin said. “I believe you. I'll have no doubts for a day or two until I can walk right again.”

  Jack lay still for a few minutes, recovering. He heard Erin and Nate talking in soft voices that he could've made out if he tried, but he didn't think it would be right to do so. Finally Erin addressed him again.

  “Let's get dressed Jack, I've got to settle up your bill. Plus give you a big fat tip. We discussed it and we'll at least want another delivery next week. How things go between now and then will determine whether or not we continue after that.”

  When Jack got back to his apartment, he finally looked at the check Erin had written him.

  Two hundred and fifty bucks for a tip? I ought to see about ditching the groceries and sticking to the personal services part of this gig.

  There was an order waiting on the printer and when he checked his business email account, there was another message from Cheryl.

  'I've got one last recommendation for you, at least the last one for now. Jessie is a special case. She wasn't sure about requesting your extra services until we convinced her. She plagues the rest of us with her attitude on sex, which is: ewww, what's so great about it? She's only ever had one man and somehow thinks that if he couldn't do something, it couldn't be done. He was pretty lame in my opinion, at least from the couple of times I talked to him. He left her a year ago or so and she needs something, I'm hoping it's attention. Anyhow, she's consented to try you out. She probably won't give you a tip, but don't worry. If you can change her attitude, the rest of us will be more than happy to
make up for it.

  Cheryl.'

  * * *

  Jessie's Attitude Adjustment

  (Cheating Wife MILF Erotica)

  The MILF Man Deliveries #5

  Holly Ardent

  Text copyright © 2014, Holly Ardent

  All Rights Reserved

  Jack made sure he had the list and the map when he left his house in the morning. His first stop was the grocery store. He knew it well enough that he zipped through the shopping required for this delivery. He checked out with the cute young checker whose ass he used to stare at whenever he was bagging on her shift. They'd flirted a lot, but it had never gone anywhere.

  All he could think was that she'd look so much better in another fifteen to twenty years. Her smile, which once had sparked erotic daydreams for him, looked forced and uncomfortable. Her flirtatious comments now seemed more like a tease than come-on.

  I know what sexy is and she might have it in a few more years. Once she's a little more experienced and mature. Right now, all I see is inexperience and a lot of work for whatever guy ends up helping her learn the hard way. I'll take the ladies with more experience any day, now that I have a basis for comparison.

  He bantered with her a little, trying hard not to flirt. She didn't even seem to notice the difference. When he'd paid, he headed out for his car and packed away the delivery for the drive to Jessie's house.

  He looked at the order sheet again.

  She signed it Jessica, but Cheryl called her Jessie. I better stick to using Jessica.

  It was a short drive, Jessica lived in the same neighborhood as most of the other deliveries he'd made so far. The house was a mid-sized cookie cutter model. The yard was slightly overgrown and there were signs that children lived there. The bike in the front yard and the swing-set in the back seemed to place Jessica in the same category as the other deliveries he'd enjoyed earlier in the week.

  It only took a couple of minutes to load his hand truck with her groceries. He dragged it to the front door and rang the bell.

  The door swung open a bit and a woman looked out at him. She was dressed in a baggy sweatsuit with her hair tied back carelessly.

  “Yes?” she said.

  “Jack Be Nimble Deliveries. I have an order for Jessica, do I have the right address?”

  “Yes, one moment.”

  She shut the door on him.

  What the hell? Jack thought.

  His confusion cleared a moment later when he heard a chain being disengaged and the door swung open again.

  “Come on in,” she said. “I wasn't really expecting you. I thought that Cheryl and the girls were trying to pull a prank on me so I was all ready to go to the grocery store after lunch. Looks like I won't have to now.”

  “No ma'am, you won't. Show me to your kitchen and I'll unpack your bags. I can help you put stuff away if you like also.”

  She looked wary for a moment.

  “How are you going to help me put stuff away? How would you know where I keep things?”

  “I wouldn't, but you do and I know what bags things are in. So you tell me what you want off the list and I hand it to you. It saves you the time you'd spend searching through the bags.”

  She relaxed.

  “Oh, yeah. I guess that makes sense.”

  Jack followed her back to the kitchen and helped unload. He glanced around the, relatively, clean kitchen. The crayon drawings attached to the refrigerator with magnets told him that she had a younger child, or more than one. When they finished unloading he placed his bill on the counter.

  “Cheryl told me you might be interested in something else?” he said.

  She hunched over slightly.

  “Umm .... uhhh ...,” she stuttered, “I'd like to talk some if you don't mind.”

  “That's fine ma'am,” Jack said.

  “Please? Drop the ma'am. My name is Jessica, I feel old enough already without being called ma'am.”

  “I'm sorry Jessica. I try not to use someone's first name unless they've invited me to.”

  * * *

  “Come on out into the living room,” she said. “We can sit and chat.”

  “Sure, we can do that. Are you not interested in the other things they mentioned?”

  “Oh,” she said. “You know, I gave some thought to them not pulling a prank on me and you aren't at all what I expected when I wondered what the man they were talking about would be like.”

  “You mean, because of the other things they told you?”

  She nodded.

  “You thought I'd be this ravening beast, tossing grocery bags left and right as I came after you?” he asked with a grin.

  She laughed, nervously.

  “Kind of. Or one of those guys they show on the covers of the bodice rippers. The ones with half their chest exposed and a grin that says that they're going to take whatever they want.”

  Jack chuckled.

  “Sorry to disappoint you.”

  “Oh no, you aren't a disappointment at all, just not what I was expecting if they weren't having a laugh at my expense,” she replied.

  “I'm just me, a guy fresh out of college trying to start a new business. You see, I ran into Cheryl at the store I was working at ...”

  Jack told her the story of how he ended up sitting here in her living room and Jessica was an attentive audience. He glossed over the more personal parts with generalizations. As he talked, Jessica slowly straightened up so she wasn't sitting hunched in on herself. Twice, Jack caught her trying to fix her hair, only to stop herself when she realized what she was doing.

  “So, Cheryl just went after you when you delivered to her?” Jessica asked eagerly.

  “I was a bit thick and didn't quite believe what was happening, so she had to be a little aggressive to let me know.”

  “It didn't bother you that she's twenty years or more older than you?”

  “Why should it?” Jack asked.

  “She's old enough to be your mother,” Jessica said.

  “Not quite, but my mom certainly never acted like that with me. I'll tell you what. In less than a week I've decided that older women are a far better choice. For a variety of reasons that I won't go into at the moment.”

  “Why wouldn't you want someone your own age?”

  “You want the whole list? Lack of experience, a lot of them need their hand held, problems with insecurity, a much stronger set of inhibitions .... Shall I go on?” Jack asked.

  “Um, no. I think I get your point. So it really doesn't bother you to be with an older woman?”

  “Not at all, I've enjoyed it every time so far.”

  Jessica straightened up even more and Jack saw her reach for her hair again before forcing her hand back to her lap.

  “You really find them attractive?”

  “In general, yes.”

  “How about me?” Jessica asked shyly.

  Jack grimaced.

  “I think that you're probably attractive, but it's very difficult to tell. It looks like you chose your clothes either because you don't want to be found attractive or to hide that you are. The same with your hair.”

  Jessica looked at herself self-consciously.

  “Would you excuse me for a few minutes?” she said.

  “Certainly.”

  Jack looked around the room while Jessie was gone. It was slightly messy and looked lived-in. Once again the edge of a toy peeking out from under the couch, the bag of blocks in the corner, and a few other tell-tales let him know that children lived here. One corner was tidier than the rest of the room. In it were a computer desk with a laptop on it and several bookshelves.

  At a guess, that's her spot and the kids aren't allowed over there, Jack thought.

  The sound of footsteps on the stairs drew his attention and he looked over to see a very changed Jessica coming down the stairs and entering the room.

  His eyes widened as he took in her knee length pencil skirt, tight sweater, and black nylons. She'd brushed her hair out also
and it looked magnificent done up in a simple style as opposed to thrown back in a ponytail with escaped wisps here and there. The low heels she wore made her almost tall enough that their eye levels matched.

  “So now do you find me attractive?” she asked.

  “Very much so,” he said.

  “Ooooh, I hate that!” Jessica said. “I'm the same person I was fifteen minutes ago, yet now I'm attractive? Guys do that all the time. I dress professionally like this for work and they're all over me. I dress comfortably and they treat me like a leper. What difference does it make what I'm wearing? I'm the same person still, I've got the same mind and body, no matter how I'm dressed.”

  Jack thought fast.

  “I'm guessing that was supposed to be a rhetorical question, but I've got an answer for you if you want it,” he said.

  The look of irritation on her face intensified.

  “Oh really? Please, enlighten me.”

  “Okay, it's going to be a bit roundabout, but I think you'll see my point when I'm through.”

  He gestured to the bookcases in the corner.

  “Essentially what you're saying is that you shouldn't judge a book by it's cover, right?

  “I guess that's what I mean,” she said. “At least it's close enough.”

  “I saw you examining the produce I brought for you. Why did you do that?”

  “I wanted to make sure that it was good quality, no spots or blemishes. It looked very nice, by the way.”

  “Thank you, but why were you worried about it? If a banana has some brown spots, it's still good. That just means it's ripe. If a pepper is slightly malformed, it still tastes the same.”

  “Because that's how you judge the quality of the produce, it's the only way to do it without cutting it open and looking.”

  “So, you're saying you choose your produce based on its appearance. You use the appearance to judge its quality.”

  “Wait a second, you aren't comparing me to a banana, are you?”

  “No, I'm just using it as an example. I have a business degree and one of the things they taught me is that customers will be swayed by appearance. If I'd shown up here in dirty jeans and a t-shirt that looked like I'd just played a baseball game in it, what would you have thought?”