The MILF Man Deliveries Series- Complete Set

by Holly Ardent

  “Brenda?” Jack asked.

  “That's me, you must be Jack?”

  “Yes, I am. Cheryl asked me to bring a package to you. She insisted I give it to you first so, here you go.”

  Jack handed her the package. Brenda glanced at it, but made no move to open it.

  “Come on in. The kitchen's just down this way.”

  Jack followed Brenda down a short hallway. He began to unload the grocery bags onto the counter, taking out the refrigerated and frozen goods first. Brenda busied herself putting those away but when they were taken care of she headed out of the kitchen, carrying the package from Cheryl, instead of starting on the other bags.

  When Jack finished unloading the hand truck, he went looking for her. She was sitting in the next room, draining a glass of wine. From the look of the bottle on the table it was probably her third or fourth glass.

  “Would you like a glass of wine Jack?” Brenda asked.

  “I'd love to, but I'm driving.”

  “A big guy like you? You ought to be able to handle a glass of wine without even getting tipsy. Besides, if you want to you can keep me company until it's out of your system. That should only take an hour or so.”

  “Just one then,” Jack said.

  Brenda poured Jack a glass of wine and refilled her own glass. Then she slipped the note out from under the ribbon on the package. She read it and glanced up at Jack, then back down to the note.

  Brenda proceeded to make small talk with him for a few minutes. Jack tried to keep up his end of the conversation, but he kept wondering if she was trying to flirt with him.

  I'm not sure if she's trying to flirt or if she's just really tipsy, he thought.

  Finally Brenda caught his eyes and held his gaze for a few seconds. When he returned her gaze, but did nothing else, she shook her head. She stood and picked up the package.

  “Wait here please, I'll be right back.”

  Where does she think I'm going to go? Jack thought.

  Jack sipped at his wine and waited. After a couple of minutes he grew curious. Brenda had left the note lying on the table between them. Jack gave in to temptation and, keeping an ear out for her return, picked it up and scanned it.

  'Here's another present. I went out and picked it up just for you last night. Jack's a little shy, or maybe he just doesn't want to make the first move and risk losing a potential customer. Either way, put this on and show it to him. Then he'll know what you want for sure.

  Cheryl'

  Jack slid the note back on the table and settled back in. He sipped his wine and waited some more. A few minutes later he heard Brenda approaching the room.

  He looked up and watched her enter the room. Now he could see a lot more of her. She was wearing lingerie; a filmy black negligee on top, black panties with a lace panel in front of the crotch and some sort of leopard print pattern along the edges, and sheer black stockings. There was nothing covering the rest of her body. He stared.

  Brenda looked at him and caught him staring. She smiled, something she hadn't done in front of him yet.

  “Good, she was right. Like what you see?”

  Jack nodded.

  “If you want to see more, you'll have to do something about it,” Brenda said.

  Jack stood and approached her. There was something odd about the expression on her face. Then he made the connection. Despite her bravado, the look on her face was the same one you'd find on a puppy that knew it had done something wrong and was waiting to be punished.

  That's just weird. It almost looks like she thinks I won't be interested and that I'm going to be upset. Hell, all the girls my age act like it's this massive favor if they have sex with you, but she's acting like it's the other way around and she's sure I'll say no. Maybe I should put her at ease? But, how?

  Jack knew it probably wasn't the best idea but it was the only one he could think of. He caught her eyes with his gaze, then allowed it to travel down her entire body and back up. He gave a slow wolf whistle.

  “Wow,” he said.

  Relief flooded Brenda's face. He saw her entire body slump slightly with relaxation.

  “You really do like what you see? You weren't just saying that you did?” she asked.

  “Brenda, yes I like what I see. Here, let me prove it to you.”

  He reached out and took her hand, then he pulled it down to the front of his jeans and pressed it against his erection through the cloth.

  Brenda's eyes widened.

  “Oh my,” she said. “That's … impressive. Cheryl told me you were well hung, but I'm pretty sure she exaggerates a lot so I wasn't sure.”

  Brenda realized what she'd just said and color rushed to her cheeks.

  “I'm sorry, I shouldn't have said that.”

  “Why not?” Jack asked.

  Brenda looked at him for a moment, opened her mouth as though to speak, snapped it shut again, and hurried over to her wine glass. She picked up the glass and emptied it, then tried to fill it again from the bottle. There was only half a glass remaining and she looked at the bottle in disgust when she realized it was empty. She emptied the half glass in one long gulp.

  “Oh damn. I need to go get some more wine.”

  Jack reached out and put his hand on her hip. He gently turned her to face him.

  “Why do you need more wine?”

  “You're right, I don't need more wine. Would you wait just a minute again? I'm sorry I keep asking you to wait.”

  She edged away from his hand and hurried towards the kitchen. She came back a moment later with a bottle of Glenfiddich, poured about two shots worth into her glass, and started sipping.

  “I need it because I want to talk. Cheryl told me that if I just told you what I wanted, you'd be happy to take care of me, but I can't talk about that kind of thing unless I'm drunk.”

  She tipped the glass back and drained it.

  “Now, in a minute or so, I'll be able to talk about it.”

  Her eyes locked onto his face for a moment and she smiled. Then her gaze traveled down his body and back to his face.

  “She said you like... Well, that you like more than just shoving your cock into a woman until you cum. You like doing other things first.”

  “Yes, I enjoy foreplay,” Jack said.

  Brenda blushed.

  “Yeah, that's what I was talking about. Well, I like it too, or at least I used to. I don't know anymore, it's been so long since I've had any. I don't consider being fingered until I'm wet enough for my husband's cock foreplay. I miss it, it's been years. He's never home and when he is and I ask for sex? It's wham, bam, thank you ma'am, and then he's done. Doesn't want to touch me again until the next time. So, what I want is ... I want you to ...”

  “You want me to run my hands all over your skin? Caress your breasts, your nipples, your ass? Maybe take my tongue to you?” Jack asked.

  Brenda was flushed and breathing heavy. She started to answer, but settled for just nodding instead.

  Jack stepped over to her and leaned his head down to her neck. His tongue caressed her skin, moistening it slightly before his lips came down and kissed it. He inhaled her fragrance and tasted her.

  Meanwhile he had one hand capping the Glenfiddich. Brenda's eyes closed as he worked on her neck and he moved the bottle to where she wouldn't see it when she opened them again.

  Jack gently kissed her neck, moving outwards to her jawline, and finally to her lips. When he pressed his lips against hers and thrust his tongue into her, her arms wrapped around him, holding tightly, and she melted against him. Jack's erection throbbed at the feel of her entire body pressed against his.

  She pulled away after a minute. When she spoke her speech was slightly slurred, but she was standing steady, not wobbling at all.

  “I want foreplay, I want at least a half hour of it. I'm not going to leave you hanging, we'll do more after that. As a matter of fact, give me half an hour of decent foreplay and I'll probably be ready to do anything you want.”

>   Jack's answer was to slide his hands down to her ass. He fondled it and used his grasp to pull her in tight against him. He kissed her again, this time her lips were open and waiting for his tongue to enter her.

  When he broke off the kiss.

  “Are you sure? I'm more than happy to do that but I think you're a little drunk and I don't want you to regret it.”

  “I'm not a little drunk, I'm a lot drunk. But yes, I'm sure. Give me what I want and I'll be your little whore in return. You can use me however you want. Just, when it gets to that point could you do me one favor, don't just thrust into me a few times and cum. I get more of that than I want already.”

  * * *

  Jack led Brenda to the couch and helped her lie down. He undid the ties on the front of the negligee and watched her breasts sprawl to the sides as he opened it. He brushed the sides and backs of her breasts with his fingertips and her nipples sprang to attention.

  Jack's hands moved to her nipples. He lightly brushed his fingers over their tops, barely making contact. They responded by becoming harder still and surging up to make firmer contact with his fingers. He pinched them, gently at first and then harder, until he got a reaction from Brenda. When he saw her teeth gnawing at her lower lip he moved his mouth down to her nipples.

  Jack gently licked Brenda's nipple, feeling it quiver beneath his tongue from the attention. His tongue traveled down to circle her areola and it firmed up in response, providing a rubbery, bumpy texture to explore and enjoy. His hands went back to her breasts, stroking the undersides and drawing a soft gasp from her.

  He switched nipples and repeated his efforts on the second one, all the while stroking the smooth skin of her breasts. He glanced up and saw a happy, contented look on her flushed face.

  Jack trailed his tongue gently down her breast, moving to the underside. He caressed the underside of her breast with his tongue. The taste of her was strong there and he enjoyed it enough that he wanted more. His tongue danced its way down her ribs and stomach, stopping to tickle her navel. From there it continued traveling down until it hit the fabric of her panties.

  Jack paused to grab her panties and slide them down her legs and out of his way. Then his tongue continued moving down. Her pubic hair was trimmed short. It wasn't the bald pussy he'd prefer but by this point, it wasn't enough of a bother for him to even remove his tongue from her skin. He continued down until his tongue slid into her pussy. The taste of her was strong there also, but slightly different from what he'd tasted earlier. There were hints of spice and musk to her taste. He eagerly began lapping at her, savoring the taste as much as the tiny noises coming from Brenda's throat.

  Jack's tongue danced around the edge of her labia, he sucked them into his mouth one at a time and gently tugged on them. He drove his tongue as far into her as he could, curling the tip to reach the inside edges of her, stroking them with the tip of his tongue. Her pussy got wetter and wetter as he worked on it, the taste in his mouth growing stronger all the while.

  He worked his way up her pussy and began to tease the hood of her clit, pushing the tip of his tongue under it and gently touching the mound of flesh it covered. His tongue danced circles around her clit and when he increased the pressure against her skin, her breathing became heavier still. Finally he pushed the hood of her clit out of the way with his fingers and blew a steady stream of air over the revealed nubbin of flesh. She shivered and shuddered, thrusting her hips upwards as though she could apply pressure to it on her own.

  Jack leaned down further and sucked her clit between his lips. He tugged gently on it, using just enough pressure from his lips to keep her clit from getting away. He rearranged his hands and kept her clit exposed with one thumb keeping the hood from covering it. His other hand moved and started stroking up and down her pussy. He slid a finger into her, and then a second, and a third. He started gently pumping his fingers in and out of her pussy while he sucked on her clit. His tongue started flicking against the flesh trapped between his lips. Brenda called out intelligibly and bucked beneath him, pulling herself out of contact with him. Jack sat up and looked at her. She was still in the middle of an orgasm so he dropped his fingers to her clit and idly played with it, extending her orgasm.

  She finally finished and laid there limp and still.

  “Brenda, roll over for me,” Jack said.

  It took her a minute or two, but she managed. Jack sat down on her ass, his legs splayed out to either side of her. He moved his hands to her shoulders and began to massage her. The tiny noises coming from Brenda's throat grew louder, if no more intelligible. Jack could feel the tension in her muscles and leaned into his task.

  “I don't know if it qualifies for you, but a lot of people claim that a massage is good foreplay also. I thought you could use one, you seemed kind of tense,” he said.

  “Ungh,” Brenda said.

  Jack wasn't sure if that was agreement or what, but she wasn't trying to stop him so he kept going. He worked his way down her back, kneading and pressing on the knots he kept finding in her muscles. When he got to her lower back it was a mass of tension, the muscles tight enough to feel like bones. He used his thumbs and drove into the knotted muscles, forcing them to unknot and slowly relax. Brenda grunted with pain at one point.

  “Did that hurt?” Jack asked.

  “Uh-huh.”

  “Do you want me to stop?”

  “Uh-uh.”

  The negation came along with Brenda's head shaking from side to side so Jack was pretty sure she meant it. He kept working on her lower back and when he had it relaxed, he moved on to her ass.

  As he massaged her buttocks, his efforts were as much fondling as they were massage.

  Damn, that's a nice ass, he thought. Plump with a little bit of padding, but mostly muscle. I suppose I ought to move down to her legs but...

  Jack massage her buttocks for a few more minutes before moving to her legs. He worked his way down them, rolling up the stockings as he went. When he got to her feet, he slid the stockings off and worked on her soles for a few minutes.

  “How's that?” he asked when he finished.

  It took Brenda a minute to answer.

  “Nice. No, better than nice. It's heavenly,” she finally said.

  “Good, do you want to just relax for a few minutes or keep going?” Jack asked.

  “Ummm, come up here and stand beside my head?”

  Jack stood up and stepped up beside her.

  “I've never been very good at giving head, but I can just lie here and let you fuck my mouth if you want,” she said.

  She turned her head so she was facing him and opened her mouth. Jack slid himself inside. He only got a few inches in before he stopped. He pulled out and started pumping in and out of her mouth. After a couple of minutes, he stopped.

  “You know, if you want me to I could give you some pointers on that,” he said.

  “What?”

  “You sounded like you regretted not being good at it. I'm just offering to help.”

  Brenda sat up and glared at Jack.

  “I had some girlfriends tell me how. When I tried it out, my husband wasn't impressed.”

  “Did he tell you why not?”

  “No.”

  “Did your girlfriends have a cock right there for you to try their tips out on?”

  “No.”

  “I can do both of those things and I'm offering.”

  “Do you think it's something I could learn?” Brenda asked.

  “You'll never know until you try. I'm more than happy to help and maybe it would give you some sort of foreplay you could get a certain someone's attention with.”

  “He'll want to know where I learned it,” Brenda said. “That's what he asked last time.”

  “So tell him your girlfriends tried to help again and it took this time. It isn't really a lie since Cheryl sent me here. You could construe that as her trying to help, no?”

  “That's kind of stretching things.”

 
“Just saying.”

  Brenda thought for a moment, looked at Jack, and nodded.

  “Tell me what to do,” she said.

  “First, what did your friends tell you before?”

  “They talked about treating a cock like it was a lollipop or an ice cream cone. Licking it like it was one of those.”

  “That's a great start, feels good for the guy, but certainly isn't going to get them to cum. Try this: moisten your lips, press them together, then put them against the tip of my cock and push your head down, forcing me between your lips.”

  Brenda licked her lips, leaving them glistening with moisture. Then she pursed them together and leaned over Jack's cock. He felt the pressure as she pushed her head down. His cock slipped between her lip and he let out an involuntary sigh. She pushed down and kept going until she gagged. Then backed off.

  “Okay, remember how deep my cock was in your mouth when you gagged, okay?”

  She nodded.

  “Now do that again, but instead of continuing on to where you gagged, stop right before it and slide your lips back up my cock. Keep them pressed together as much as you can all the time. One other thing, if you do keep giving head, you can increase how deep you can take a cock by holding them as deep as you can without gagging. Let yourself adjust to that, then slip them a tiny bit deeper. Over time you might even manage to get them all the way in. If not, you'll still get more of them.”

  Brenda leaned back over and Jack felt his cock slip through her lips again. This time Brenda started bobbing up and down on him. After a minute or so her motion became rough and a little jerky. She stopped again.

  “What happened?” she said. “I thought I had it, but then ...”

  Jack looked at her. Her lips were no longer glistening and moist.

  “Your lips dried out. You can either figure out a way to keep them wet while you do that or you can put on some lip gloss or something else that will keep them from drying out right before you start. Now moisten them again and I'll show you another trick.”

  Brenda licked her lips again and watched Jack.

  “Now take me in your mouth again but stop right before you gag. Hold still at that point.”