The MILF Man Deliveries Series- Complete Set

by Holly Ardent

  “I told you I'd get it all the way in before we were done,” she said.

  He grabbed the braid of her hair and wrapped it around his hand. He pulled on it until her head was upright and then drove his still hard cock into her mouth on his own. He held her in place as he fucked her mouth hard. When he started to go soft a minute later, he pulled out and let go of her hair.

  Jack slid the pin out of the stocks and raised the top, but Linda made no move to get out. He slumped down against the edge of the stocks for a moment, until he was sure he had his balance back. Then he stood, picked her up, and carried her over to the couch. He slid down in front of it for a moment, leaning his weight against it.

  “What are you doing tonight? Would you like to stay here?” Linda asked.

  “Yes, but I can't. Sorry, I've got to get back to my apartment to check for orders. I suppose I ought to set that up so I can do it remotely,” Jack mused aloud.

  “Damn,” Linda said, without much emphasis. “I suppose I wouldn't be much good for anything else the rest of the night anyhow, but I'd hoped.”

  “I'm pretty sure that I wouldn't be much good for anything of the sort either,” Jack said.

  “Tell you what, I've got a bunch of props and costumes I never got to use. You want to play with them next week after you deliver my order?”

  “I'd love to,” Jack said.

  “Good, I'll go ahead and edit the video tonight. If you give me your email, I'll send you a copy.”

  * * *

  Erin's Errands

  (Cheating Wife Cuckold MILF Erotica)

  The MILF Man Deliveries #4

  Holly Ardent

  Text copyright © 2014, Holly Ardent

  All Rights Reserved

  I wonder how many friends Cheryl's going to recommend me to, Jack thought as he entered his apartment. He glanced over at his printer and noticed that there were two orders printed out. He shook his head, exhausted.

  I hope those aren't both Cheryl's friends who want me to deliver more than just their groceries, he thought. Linda left me exhausted, if those both want something similar, I'm gonna end up hurting myself.

  He picked up the orders and scanned through them. The bottom one mentioned his flyer and requested the half off delivery charges deal he'd printed on them. He sighed with relief.

  Good, if they aren't one of Cheryl's friends, then they probably won't be asking for my personal touch, as it were.

  The second order was another lady Cheryl had recommended. On a hunch, he opened his work email and found a message from Cheryl, as he'd expected.

  'Hi Jack,

  Linda said you were everything she'd hoped for and very tolerant of her special requests. I've got another friend who likes things a little different also. I thought that since you'd done so well with Linda you might want to give Erin a try. Like Linda, she'll want to take a look before asking for anything. Also like Linda, if she finds you satisfactory then the end result should be both interesting and profitable for you. Just thought I'd give you a heads up about her.

  Hey, can I reserve a delivery time for myself next Monday in advance? I don't know what groceries I'll want yet, but I know when I'll want you here. Let me know please.

  Cheryl...'

  Jack hit reply and began to write.

  'Cheryl:

  I don't have that built into my program yet, thank you for the suggestion though. I'll talk to the guy that programmed it for me and see if he can add that.

  I'll be happy to manually reserve whatever delivery time you want, just let me know when.

  Jack.'

  He hit send and glanced over the second order.

  Yup, it's from Erin, he thought. That's an Irish name, isn't it? I wonder if she's the classic pale, freckled, redhead. That would be a bonus, although I'd have to watch out for the temper.

  Jack set the two orders down on the table next to the door. He'd be able to deliver the first one before going to Erin's tomorrow. He sat back down at the computer and sent an email to Mark, his programmer friend that had created the programs he was using for his business.

  He asked Mark to come over Friday night. Jack would supply the pizza and beer. They could talk about the program then. Jack thought about adding in some stories of what his work week had been like, then decided that Mark would never believe him.

  He sent the email and threw himself on the couch.

  Damn it, I'm exhausted. But I refuse to go to sleep this early.

  Jack glanced at the books on his bookshelf, but he'd already read and re-read most of them. Instead, he found the remote for the television and mindlessly channel surfed for a while. Then he got up and made himself some dinner before settling in front of the TV again. At some point during the evening, he drifted off to sleep, the television still running.

  * * *

  Jack woke earlier than usual. He was stiff and sore from sleeping on the couch.

  I've got extra time, maybe I'll stretch and go for a run. It isn't my normal day for it, but I think I need it.

  He tossed on a pair of sweats and went running down at the lake. Much to his surprise he found himself eyeing the women joggers his own age and wishing they were older.

  I guess the MILFs are getting to me. If I asked a girl my age to do half the stuff they've let me do, I'd get a slap in the face and a “Good night, Jack”. Hell, the older ladies even ask me to do stuff that the younger ones would kick me out for.

  When he finished his run he took a quick shower. There was still plenty of time for breakfast before he needed to make his first delivery.

  The first one took less than twenty minutes after he left the store, but he could see where he'd need some sort of plan to get multiple customer's groceries at one time and keep them separated in his car. If his business got as large as he hoped, he'd need the time that saved him.

  Since the first order was requested for nine in the morning and Erin's was after lunch, he had a few hours to kill. Linda had paid him in cash the day before and he didn't like carrying that much money around, so a trip to the bank was in order. After that he treated himself to lunch at a restaurant.

  He went back to the grocery store and picked up Erin's order. She lived farther away from Cheryl than the other ladies she'd recommended, but he thought it was still basically the same neighborhood. When he arrived at the address, he was startled to find a security fence around the entire property. He pulled up to the gate and pressed the buzzer.

  “Yes, who is it?” A female voice asked.

  “Jack Be Nimble Delivery. I'm here with an order for Erin?”

  “Oh Jack, you're just a touch early. I'll open the gate for you.”

  The iron gate began to roll to the side, slowly.

  When it was open far enough, Jack pulled into the driveway. The gate closed behind him as slowly as it had opened. He parked his car and loaded the order onto the hand truck. The doorbell was a two-tone chime that was audible on his side of the door.

  The door opened. A slightly plump redheaded woman stood there.

  Wow, I was just kind of joking because of her name, but she is an Irish redhead. Or at least she's pale and redheaded. It looks like she got off light with the freckles though.

  “So you're Jack?” the redhead asked.

  “Yes, I guess you're Erin?”

  She nodded.

  “Come on in Jack. Let's get the groceries into the kitchen.”

  Jack rolled the hand truck down a hardwood floored hallway and into the kitchen. He parked it and pulled off the first two bags, the ones containing frozen and refrigerated items.

  “Here's the stuff that needs to go right into the refrigerator,” he said.

  Erin took the bags and busied herself for a moment putting the items away. Jack watched with interest, but Erin's clothes weren't tight enough to reveal anything about her figure. The slacks and sweater she was wearing weren't loose, but they weren't tight either. From what he saw she looked as though she were well put together with generous
curves, but he wouldn't put money on it without a better look.

  “Would you mind helping me put the other things away?” Erin asked.

  “Not at all, what would you like me to do?” Jack asked.

  Erin smiled.

  “I know where everything goes and you know where things are now, so I'll call off the items on the list. You can hand them to me and I'll put them away. That should be the quickest way to take care of it.”

  Jack lined the remaining bags up on the counter. Erin started calling off the items on the list, from memory. Jack struggled to keep up with her as she quickly worked her way through the order.

  “Thank you Jack. Would you mind chatting with me for a bit in the sitting room?” Erin asked.

  “Not at all.”

  Jack gathered up the bags and left his bill sitting prominently on the counter. They left the hand truck in the kitchen and moved to a room at the front of the house. The curtains were wide open and the room was bright and sunny.

  Erin took a seat on an old-fashioned parlor chair and motioned him towards another.

  “Have a seat Jack.”

  Jack sat down and looked at her. A noise from upstairs caught his attention. It sounded as though someone had dropped something heavy. Erin didn't even look up.

  “So, I understand that Cheryl has used your services and recommended you to several of her friends,” Erin said.

  “Yes.”

  “You do understand that I'm not talking about your grocery service, correct?”

  Jack nodded.

  “I understand what you're saying.”

  “She also told me that you've proven open-minded about some relatively outrageous things.”

  “I'd say that I have, but that's only from my own viewpoint,” he replied.

  “That is the opinion both Cheryl and Linda gave me. Since you agree with them, I'll take it at face value.”

  Erin paused for a moment, unnecessarily straightening her clothing.

  “I have an outrageous request myself, at least many people would consider it such, and I was hoping that you could help me with it,” she said softly.

  “Well Erin, if you tell me what it is, I can tell you if I can help,” he said.

  “This is always the hardest part,” she said. “It's impossible to know how someone will react. So, I have a question for you that might give me an idea of what you'll think of my request.”

  “Go ahead, ask.”

  “Linda was very open with me. She told me that you consented to make a video with her, of an erotic nature, that she intended on showing to her absent husband. Did it bother you knowing that another man was going to watch it?”

  Jack considered the question for a moment, phrasing his reply carefully.

  “In the end it didn't bother me at all. I was a little hesitant at the start, but I decided that I had nothing to be ashamed of. Plus, her husband sounded like an incredible jerk and I was happy to help her get what payback she could. That made it easier.”

  Erin relaxed almost imperceptibly.

  “Good, the request I have is somewhat close to that one, except the other man in question is not a jerk. He has certain ... problems that we've discovered how to overcome.”

  “I'm not sure I understand,” Jack said.

  “I'd prefer that what I'm about to tell you never leave this house, whether or not you decide to assist me in this matter,” Erin said.

  “I'm more than willing to keep a secret, especially if it's one that doesn't involve me. So go ahead.”

  “My husband and I have some marital problems, in a physical sense. He has a certain condition that makes it difficult for us to engage in marital relations. It is primarily an involuntary mental condition, but we've discovered how to overcome it for brief periods of time. If he watches me and another man engage in that type of activity then he becomes capable for up to a week.”

  Okay, I think she said that her husband can't get it up unless he's seen his wife get done by another guy recently, Jack thought.

  “I assume that you're considering me for the part of the other man in this?”

  Erin blushed and nodded.

  “Let me make sure I understand. You and I would do things together, he just wants to watch?” Jack asked.

  “Yes, infrequently he does want to join in.”

  “I'm sorry, but I'm not interested in anything where I'm doing things with another guy.”

  “Oh no, I didn't mean to imply that. When he asks about that, what he means is that he wants the other man and himself to both be having relations with me at the same time. Not anything between the two men.”

  Did Erin just say that her husband wants her double penetrated sometimes, and that she lets it happen? She seems a bit of a prude for something like that. How can I point that out, delicately?

  “Forgive me for saying so, but that doesn't sound like the type of thing you would allow. At least not from what I've gathered of you through our short acquaintance,” Jack said.

  Erin threw back her head and laughed, a true belly laugh, not the more delicate titter Jack would have expected.

  “Oh Jack, you aren't used to trying to talk around things are you?” she said.

  Jack shook his head.

  “I will be blunt with you to answer this question,” she said. “I decided, long ago, that one of my favorite authors had the right idea on what it meant to be a woman. When I told my husband, he agreed with me strongly. The author said that a woman should be a lady in public, but a completely shameless hussy behind the bedroom door. I'm paraphrasing that of course.”

  Jack was on firmer ground now. He was sure he knew where she got that quote, and he tossed the original back at her.

  “A true lady takes off her dignity with her clothes and does her whorish best. At other times you can be as modest and dignified as your persona requires,” he quoted.

  Erin beamed at him.

  “You've read Heinlein enough that you can quote him word for word?”

  “I wouldn't say that,” he said. “But I've read a lot of his books, some of them repeatedly. I always liked that quote, so it stuck with me.”

  “I imagine most men do like that one. More women ought to, I'm sure they'd be happier if they followed it. I need to keep things very formal when I'm speaking with someone that might become one of my ... someone who might help with what I need. Many of the men that help become possessive after a while and can't understand that I am, in my own way, being faithful to my husband. As such, you've only seen the more formal side of me so far.”

  “I can kind of understand that. I don't think that would be a problem with me, even if you weren't so formal.”

  “That's one of the reasons I took Cheryl's recommendation. She told me that she, and two of her other recommendations, intend on continuing to use your services. With such a variety of willing and eager women, I think that the problem of possessiveness would not crop up this time. I must say, also, that you scored quite a few points with your quote. It wasn't the exact one I was paraphrasing, but it was from the same author, and in the same vein.”

  “It wasn't? I'm sorry, I was sure it was that one,” Jack said.

  “No need for apologies. If he hadn't written the one I used, then I might've adopted the one you quoted since they both mean close to the same thing. If you're going to try to track it down, I'll give you a clue. The one I used includes references to the kitchen, the bedroom, and ...” she gestured around the room, “the parlor.”

  “I just might look for it later on. Back to your question though. If your husband wants to participate, but doesn't expect me to do anything to him or vice versa, then I wouldn't have a problem with that,” Jack said.

  “Oh, wonderful. Perhaps it's time for me to introduce you to him. All of my extra-marital partners need to be approved by both him and me. You've got my vote, now we need to see what he thinks,” Erin said.

  She got up and walked to the base of the stairs. Then she called out.

&nb
sp; “Oh Nathan? Please come down here Nate.”

  A minute later a man came walking down the stairs. Jack was sure he was ex-military. Nathan's hair was in an extra-short buzz cut and he held himself erect with a very stiff posture. His movements were precise, as though he gauged each one before he made it. But his eyes were what told Jack the most. Jack's uncle had come out of the military with a similar, haunted look to his eyes.

  “Nate, this is Jack. I believe he could be our next partner, if you approve,” Erin said.

  “Erin, you know that I trust your judgment, yet you ask me each time,” Nate said. “Jack, I'm sure Erin has explained things to you already? I'm not going to worry about you like I have some of our past partners. I've been kept up to date on the gossip from Erin's friends. Sounds like you've got your work cut out for you.”

  Jack hesitated, wondering if he should offer to shake Nate's hand.

  You know what? It doesn't matter why I'm meeting him, it's just polite, he thought.

  Jack stepped forward and extended his hand.

  “Nice to meet you Nate. Yes, Cheryl and her friends are keeping me hopping, but I'm not about to complain. I just want to know what I did to get so lucky.”

  Nate chuckled and gripped Jack's hand.

  “You've got the right attitude and from what I've heard, you don't stint people. I think that's what you're calling luck. It isn't though, it's just people recognizing the attitude. You do what you say you will, no bullshit. You don't get that from many people nowadays.”

  Jack was at a loss for words.

  “Nate has this tendency to be blunt and speak what he believes,” Erin said. “He may be right in this case though, everything I've heard about you has been glowing.”

  “I'm not really that great a guy. I just believe that if you're going to do something, you ought to do it right,” Jack said.

  “That's exactly what I was talking about. Even if you're just doing people's errands, you do it the right way,” Nate said. “He'll do, Erin. I think he'll do nicely.”