The MILF Man Deliveries Series- Complete Set

by Holly Ardent

  She directed him to the kitchen, walking along just behind him. Jack turned around when they got to the kitchen and caught Linda checking him out. When he turned, her eyes were obviously traveling up and down his body.

  “You'll do on the physical front,” she said.

  Jack cocked his head.

  “What?”

  “Oh, nothing. Just talking to myself. Would you help me with the groceries please?”

  “Of course,” he said.

  The put the groceries away quickly. Linda turned to him.

  “Would you like a beer? I've still got some hanging around in the refrigerator. I don't drink them myself.”

  “Sure,” Jack said.

  She took out a bottle and opened it for him. She took a second, different, bottle out of the refrigerator for herself.

  “Please, come with me. I want to ask you a few questions,” Linda said.

  She settled them into the living room. After a few minutes of small talk, she started asking some questions that Jack found strange.

  “How do you feel about masks? The kind that covers the top half of your face. I've made sure that they're snug and won't fall off.”

  “I wore some when I went trick or treating as a kid. I never had a problem with them then, haven't tried one on recently though,” Jack said.

  “Good, good. Do you get camera shy at all?”

  “No, ma'am. I'm not shy of cameras at all. Can I ask why you're asking me these questions?”

  “Please, call me Linda.”

  “Okay Linda, but the question still stands.”

  “Can I ask you a few more questions first? Then I'll answer that one,” she said.

  Jack nodded curtly.

  “How are you at acting?”

  “I've never done any so I don't know,” Jack said.

  “Maybe that was the wrong question. Cheryl told me that you were very enthusiastic when she had you, or you had her, however that happened. Take a good look at me and tell me if you think you could be enthusiastic about having sex with me.”

  Now Jack felt like he was on more familiar ground, and was momentarily weirded out that it was familiar ground. He took a good long look at her, his eyes moving from her face to her feet and back.

  Linda's hair was reddish blonde, although her roots were slightly darker and he wasn't sure if she dyed her hair or not. She looked like she took good care of herself since she was trim and fit. With the clothes she had on, slacks and a loose blouse, he couldn't see her breasts very well but they were certainly at least a handful, which was enough for him.

  “I'll be blunt here. You're attractive enough, but it would depend on you. If you just lie there like a dead fish, then probably not. But if you actively participate, then enthusiasm wouldn't be a problem.”

  She nodded.

  “Good, I like a man who tells the truth, even with a delicate topic. What do you think about having a sex partner that dresses up; lingerie, leather, vinyl ... That type of thing.”

  “I've had partners in lingerie and enjoyed it. I haven't had a partner who dressed up in leather or vinyl, but I like the sound of that.”

  “One last question, and then I'll explain. Would you be willing to be filmed having sex with a woman if the price was right?”

  Jack thought for a moment.

  “Wearing the masks you mentioned?”

  She nodded.

  “You'd be the woman in question?”

  “Yes, with me.”

  “Are you intending on distributing this video? Like putting it on the internet or something?”

  Linda blushed.

  “Oh no, I intend to send a copy to a single individual. Maybe keep a copy myself, depending on how much I enjoy making it. The person I'm sending it to knows just enough about computers to play the video. He wouldn't know how to upload it anywhere, and even if he did it would be incredibly humiliating for him.”

  If she's right, he wouldn't know to use a video editor either, Jack thought.

  “If the price is right, then yes. I have one condition though.”

  “That is?” she asked warily.

  “I want a copy of it for myself also. I won't put it on the net either, but it would be my first starring appearance in a porn film. I'd like to have a copy for myself.”

  Linda stared at him. The blush that was still coloring her face spread to her neck and almost to her cleavage. Then she burst out laughing.

  “Fair enough, you get a copy too. How does five hundred dollars sound?”

  “That sound like a good deal to me, almost too good.”

  “Well, you'll be involved in a few things that most people consider kinky. You wouldn't have a problem with that, would you?”

  “Probably not, it depends on the kinks.”

  “I already mentioned several of them. Let me tell you what we'll be doing. My husband, the son of a bitch, left me for some young twit whose IQ is probably lower than that of the smart phone she constantly totes around. We aren't divorced yet, just separated. But he's in another state with his little twit. I intend to take a young, handsome stud and have him do everything to me that my husband liked to, plus everything he asked about and I never let him do. Then send that asshole the video of it all happening.”

  “Trying to get him back?” Jack asked.

  “Hell no! I just want him to see it and realize what he's missing. So, it needs to be good, really good. I figure we're off to a good start already. You're taller and more muscular than him. That should hit home with the rat. I want him to feel like the inferior little shit he is. I want him to wonder if he could've eventually gotten me to do the things he'll see us doing.”

  “When do you want to do this?” Jack asked.

  “Doing anything the rest of today?”

  “Nothing I can't clear off my schedule,” he said.

  I'll call in sick to my shift at the store so I don't miss this, he thought.

  “Good, my daughter has a sleepover at a friend's house tonight. She's going straight there from school so we won't be interrupted. Follow me and I'll show you where we'll be doing this.”

  * * *

  Jack looked around, checking his vision through the mask. Linda had enlarged the eye slits on the masks they were going to use. His mask was a sparkling silver color, her's was similar, but smaller and gold colored. Both masks left the face exposed below the nose. She'd told him she made that decision so they could keep their mouths in play. That she wanted the masks at all told Jack that she was worried her husband might figure out a way to distribute the video.

  The room they were in was large, with a hardwood floor and off-white walls. A digital video recorder, brand new, stood on a tripod in one corner with a cable connecting it to a large flat screen television. There were various pieces of furniture scattered about the room, as well as a wardrobe and several cardboard boxes. The furniture was obviously in the area to be filmed, everything else was tucked where it wouldn't show up on camera.

  Linda was still rummaging through the box she'd pulled the masks out of. Now that everything was ready to go, she seemed more hesitant than earlier.

  “Should I start off with the vinyl? Or maybe I should …,” she trailed off into silence.

  Linda turned to Jack.

  “What do you think? Should I start off wearing the vinyl or maybe just some tamer lingerie?”

  “That depends. You're the one trying to make a statement here. What, exactly, do you want him to be thinking of when the video starts?”

  “Me, of course. Then I want to reinforce the fact that he doesn't get me ever again.”

  “Then maybe you should start off with just you? No lingerie, just skin and a mask. Let him see what he's missing. Then you can go ahead and show him everything he'll miss out on in the future?”

  “You think so? I mean, just starting off nude?”

  “Sure, why not? There's some potential comedy value there also. What if he's working when he plays it. Or that girl you were talking about i
s watching over his shoulder? It could be awkward for him if the video just opens with you nude,” Jack said.

  “I like the way you think Jack, we'll do it that way.”

  Linda started removing her clothes, quickly and efficiently. She was nude in fifteen seconds and Jack finally got his answer about her breasts. They were larger than he'd thought, the bra she'd worn containing them until they were spilling up over the top. Now freed, they spilled gently down her chest, capped with large areolae and nipples. She obviously worked out and was in good shape. Jack felt himself reacting, his pants filling out in front as his erection grew.

  “Can you handle that camera?” Linda asked. “I'd like to make sure we're focused on this center area and not fuzzy at all.”

  Jack adjusted his pants for comfort.

  “Sure, I think I can. Let me take a look.”

  He turned the camera on and made sure it was focused where she wanted.

  “Turn the television on also, then I can see what we're recording,” Linda said.

  The remote for the TV was on top of the camera. Jack used it to turn the TV on then focused back on Linda.

  “Focus looks good,” Linda said. “What are you waiting for? Shuck out of those clothes.”

  Jack started undressing as Linda spun this way and that, looking at the television screen. She sighed.

  “It sounded like such a good idea, but I look at myself on the screen and all I see is a fat, ugly, old lady. With a funny looking bald pussy too, I never should've waxed it, even if shaving it was the one thing he always asked me to do. I'm sorry Jack, I don't think this is going to work. I mean, look at me. It's not like I'll ever be turning a man on again with this body.”

  Jack finished undressing.

  “I think it'll work just fine,” he said.

  “Don't worry, I'll pay you anyhow. I just don't think it'll have the effect on him that I was after.”

  “Really? You don't think he'd want you again after seeing you like that?”

  “I don't see why any man would.”

  Jack turned around, his erection jutting out. He caught her gaze, looked her up and down, pausing on the bare skin of her pussy and her breasts. Then he looked meaningfully at his cock.

  Linda followed his gaze and broke into a delighted grin.

  “I … might be mistaken,” she said.

  Jack nodded and walked towards her.

  “Yes, you are.”

  Jack took Linda in his arms, his cock pressed firmly against her stomach. The feel of her generous breasts, and the firm points of her nipples, pressed against him sparked a bit more excitement. Linda laughed happily when his cock twitched between them and tried to grow larger in response.

  “You're certainly ready,” she said, her hand reaching down to stroke his shaft.

  Instead of answering, Jack ducked his head and pressed his lips against her neck. He slowly kissed his way along her jawline, homing in on her mouth. By the time his lips pressed against hers, she was bubbling with excitement. She kissed him back, hard, and he felt, rather than heard, her happy sigh as his tongue slid into her mouth.

  * * *

  Linda pulled back from the kiss.

  “That's nice, but I want more. How would you like something other than your tongue in my mouth?”

  “Do you even have to ask?” Jack said.

  Linda dropped to her knees and rubbed his cock along her cheeks. Her skin was smooth, soft, and warm against him. She flipped her hair so it fell over one shoulder and then took it and wrapped his cock in it, stroking him up and down with the silken feel of her hair caressing him. After a moment she tossed her hair back over her shoulder and leaned in, kissing the tip of him gently.

  Jack shivered when he felt her tongue flick out and slide into the slit on the end of his cock.

  Damn, I've never had that done to me before.

  He squirmed as his cock grew more sensitive from the attention. Linda noticed and removed her tongue. She leaned forward and Jack felt her warm, moist lips engulf the head of his cock. They latched onto him as she began to suck. When she drew her mouth back, he felt as though she were stretching the head of his cock. He slid out of her with a loud 'pop'.

  “Yum,” she said. “It's been a while since I've gotten to play like this. Certain men, who shall remain unnamed, claimed I couldn't give head worth a damn. What do you think?”

  Jack, still off balance from her efforts, took a moment to answer.

  “I think whoever said that was a fucking moron. Wouldn't have known good head if it bit him. I've never had anyone do either of those things to me before and it was incredible.”

  “You haven't seen anything yet, young man,” Linda said.

  She pushed her lips over the head of his cock again, but this time she kept going, and going. Linda seemed surprised when she stopped but hadn't gotten to the bottom of him yet. She slid her lips back up his cock and then down again, trying to force him deeper into her mouth. After several attempts, she drew back off of him.

  “What the hell? I could deep-throat Paul. How big are you down there?”

  “It depends on how excited I am, anywhere from six to eight inches normally.”

  “So, how excited are you?”

  “After what you were doing to me a couple minutes back? I'd want a ruler to make sure I didn't break eight.”

  Linda flushed.

  “Well I'll be damned if I'm not going to get you all the way into my mouth, one way or another.”

  “If you can't manage it now, try right after I cum. I always shrink a little right away before I go soft a few minutes after that.”

  Jack's cock disappeared into her mouth again. She spent a good ten minutes trying to get all of him into her. But even her best efforts left two finger widths of his shaft between her lips and his base of his cock.

  “If you don't want me to cum this quickly, we might want to try something else,” Jack said after she gagged for a fourth time.

  Linda reluctantly pulled her mouth off of him.

  “I want to try again later,” she said.

  “Stubborn much?” Jack asked rhetorically. “Here, let me pull this chair over. You sit down, slide to the front and spread your legs.”

  Linda watched as he put the chair into place, then she sank down into it. Jack helped position her and when she was how he wanted her, he dropped to his knees and buried his head in her crotch. The mask was slightly in the way so he slid it up making a mental note to replace it later on.

  As soon as his tongue touched her pussy she relaxed. Jack noticed that the skin surrounding it was completely smooth, no stubble whatsoever, and decided to indulge himself.

  His tongue traced its way around the smooth skin surrounding her pussy, darting in to flick against her labia or penetrate her lightly. She moistened up quickly and Jack caught the taste of her on his tongue. He backed off for a moment to enjoy it.

  Her musky scent surrounded him. It was strong, but pleasant, and stimulating. His cock throbbed gently as he worked her pussy with his tongue.

  After playing with the skin surrounding her slit, he went to work in earnest. He worked his way up and down, using his tongue to apply pressure to the edges of her pussy. He played with her labia, swirling his tongue around them, pushing them this way and that. Finally, he noticed that she was getting more worked up. He moved his tongue up.

  Jack brought his hands up and used his index fingers to stroke along the edges of her pussy while his tongue played with her clit hood. He applied pressure with his tongue and heard Linda gasp. His fingers crept up and slid the hood out of the way and he brought his tongue down directly onto her clit, pressing gently against it. She squirmed, but stopped and found her previous position when his tongue slipped off of her clitoris.

  Good, she wants me to keep doing what I'm doing, he thought.

  Jack swirled his tongue around her clit, pushing it from side to side as he went. Linda's legs clenched down on his head reflexively.

  Okay then, if
she won't let me do that, I'll do this instead.

  He wrapped his lips around her clit and squeezed softly, Linda squeaked. He tightened down a bit more and her thighs clamped into the side of his head harder. Finally Jack sucked gently, stretching her clit and drawing it into his mouth. When the tip of his tongue started stroking it, Linda exploded.

  Jack let go of her clit hood and got his hands between her legs and his head before she gave him a concussion. Linda was all over the place, bouncing on the seat of the chair and squealing loudly, all while trying to hold herself still by clamping down on the armrests of the chair.

  Jack pulled back, worried about either being hurt or accidentally hurting her. After a minute or so, she went still again.

  “I didn't hurt you, did I?” she asked.

  “No, I'm fine. You?”

  “I've no idea, I feel limp. Everything just went awfully fuzzy for a minute or two. What was that?”

  “I'm not really an expert, but if that wasn't an orgasm I'll eat my shorts,” Jack said.

  “I can't orgasm, I've never been able to. Paul told me it was my own fault, that I was too uptight and frigid for it.”

  “I think we already established that he was full of shit though, didn't we?”

  Linda nodded. Then she held up the back of a hand to the camera and extended her middle finger.

  “Hear that, you asshole? You were wrong again, I can orgasm. In sixteen years of marriage, you never managed it once, but this young man did it in less than sixteen minutes. Thanks for leaving, I'm going to be so much better off without you.”

  * * *

  Linda tried to stand and decided she'd better stay sitting for another minute or two. Jack slid his mask back in place, just in case he turned and the camera caught his profile.

  “I want to start putting on some of the outfits,” she said. “I thought I'd have no problem with waiting until we went through three or four of them before having you inside of me, but now I'm impatient for that.”

  “Is there any reason we have to follow the script?” Jack asked.

  “I don't have a script, as such, but I think you might enjoy the next few parts I was planning. I think I might even enjoy them now.”