The MILF Man Deliveries Series- Complete Set

by Holly Ardent

  Nate turned and headed back upstairs. Erin glanced at him fondly and then looked back to Jack.

  “Well then, we should discuss remuneration,” she said.

  “I don't offer any extra services because of the money,” Jack said. “The others have all tipped me fairly well for my efforts. If you want, you can do the same. Whatever amount you think is appropriate.”

  “I'm sure a young man like you doesn't have a lot of money, not if you're just starting a new business. Are you sure you wouldn't like to negotiate a fee?”

  “I'm not going to worry about it Erin. Yes, extra money is nice, but I'm doing okay for myself. I've got all my bills covered at least.”

  “Well, I don't have to worry about money and I like to share. So, I'll take care to tip you appropriately later on. Now, if you're willing, I'm guessing Nathan will be waiting for us in the bedroom.”

  * * *

  Erin took Jack's hand and led him upstairs and into a bedroom. Jack was interested to note that it contained a four poster bed with canopies that could close it off from the rest of the room. Erin saw where he was looking and grinned.

  “Sometimes Nate prefers to not be seen while watching. Then we close the canopies enough so that he can only see me and not my partner since that means my partner can't see Nate either.”

  “I suppose that makes sense, except I thought he liked to watch?” Jack said.

  Erin's smile widened.

  “Sometimes he prefers to just watch my reactions and not what's going on. He tells me that it's all about how I react more than anything else.”

  Jack nodded.

  “We do have a couple of ground rules to follow,” Erin said. “The first is that you don't talk to Nate unless he talks to you first, okay?”

  “I can do that.”

  “The second is that you try to ignore that he's here and simply do what you'd normally do while having sex with a woman.”

  “I can certainly try. Like I said, I don't think it will bother me. Is there anything that you, or he, would prefer since I'm willing to do almost anything sexual with a woman?”

  “Good question,” Erin said, “I knew you were a good choice. The answer is yes, and no. I'm also rather open-minded about what I enjoy sexually. Nate may occasionally make a request if there's something specific he wants to see, or I may ask you to do something in the heat of the moment. You can ignore my requests if you like, but if Nate asks for something I'd very much like you to do it.”

  “That's fine by me, if I can do anything requested, I will,” Jack said.

  “Now, please give me a moment. It takes a little bit for me to switch mindsets.”

  Erin closed her eyes for a minute and her face went blank. When she opened them again, her eyes swept from Jack's head to his toes, and she grinned.

  “Very nice, indeed,” she said.

  Erin stripped off her sweater, revealing a white camisole beneath it. Jack could see the bra she was wearing, it was mostly white with a floral pattern on parts of it. When she pulled her camisole off as well, his questions about her breast size were answered.

  Erin was slightly plump, but by no means fat. She carried a little extra weight on her stomach, and a lot of extra weight on her chest. She was stacked and her bra pressed her breasts together creating cleavage that Jack could get lost in. He was caught off-guard when Erin cleared her throat.

  “I'd tell you that my eyes are up here, but I liked the look on your face when you were staring at my breasts. However, nothing much is going to happen unless we both get undressed.”

  “Oh, sorry,” Jack said. “If you wanted there's a lot that could happen without us both undressed. I'm not wearing a gag or gloves, am I?”

  Rather than wait for an answer, he pulled off his shirt. When he looked again, Erin's breasts were hanging free, the bra discarded on the floor. They were creamy white, capped with light pink nipples, and swayed slightly as Erin removed her slacks.

  “Jack?” Erin said.

  Jack blushed and tore his eyes from her breasts. He removed the rest of his clothing before looking at her again.

  Yup, a natural redhead. Not that I doubted it. A little more bush than I like, but it is neatly trimmed. It's just a little longer than I prefer, I don't think that'll be a problem.

  “I'm glad you like looking at me, but wouldn't you rather do something more than that?” Erin asked.

  “I intend to, I was just pausing to enjoy the view first. You're very attractive.”

  “Thank you Jack, but I was hoping for even more than that.”

  Jack stepped over to her and wrapped his arms around her back. He drew her towards him, trapping his erection between them, and pressed his lips to hers. She resisted for a moment before parting her lips to let his tongue slide into her mouth. After a few moments, she pushed him away.

  She winked at him and sensually slid onto the bed. Erin squirmed her way up and when she finally stopped moving she was positioned with her head on the pillow. One arm was stretched out and her fingers grasped Nathan's hand.

  Jack hopped onto the bed and scooted his way up alongside her. He leaned over and buried his head in her hair, nuzzling through it to find her neck. His hand moved to her breast, cupping and fondling it. Her tiny pink nipple was hard as a pebble already, the areola around it crinkled from her excitement.

  Jack nipped at her neck with his lips, lightly pinching the skin. He brushed her hair to the side and moved his lips down, kissing the top of her shoulder. He continued down, encountering the upper slope of her breast. He traced a line of moisture along it with his tongue, then backed off and gently blew air across it. She shivered and let out a soft sigh.

  Jack moved his hand down lower, encountering her bush. He made his way through it to the lips of her pussy. She was a tiny bit damp already and he stroked his fingertips along the edge of her lips, occasionally sliding them into her.

  His mouth moved farther down to find her nipple. He licked it and lapped at it, feeling it tighten more from his ministrations. He sucked it into his mouth and felt her tense up and give a sigh. His tongue danced with her nipple, licking it first on one side and then another. He flicked it over and over with his tongue, all the while keeping it trapped in his mouth, his lips firmly closed on it to keep her nipple in place.

  His free hand wandered over to her other breast, trying to cover it.

  Definitely more than a handful, and also definitely not a waste. I don't care what they say.

  The hand on her breast slipped down. His fingers trailed gently across the underside of her breast, pausing to investigate where it joined her chest. When he noticed his fingers getting slightly damp, he shifted his head, and tongue, down to the same spot on her other breast. He lightly licked across the section where her breast and chest met.

  Some sort of floral perfume, I could do without that. But the other taste there, spicy with a hint of musk, that must be her. I bet that musk is stronger lower down. Only one way to find out.

  Jack slid himself down the bed, pushed her legs open wide, and planted himself between them. He ducked his head down and tentatively licked through her bush.

  That damn bush tickles, he thought. But I was right, her taste is stronger here, especially the musky part. There's also only a hint of that perfume, which is much better.

  Jack stroked her pussy with his tongue, applying gentle pressure. Her skin molded to the force of his tongue, parting to allow him access when he pressed down in the center. He heard a gentle murmur and looked up to see Erin playing with her own breasts, Nate's hand either forgotten or disregarded at the moment.

  Jack slid his tongue upwards and traced circles around the skin covering Erin's clit. When he applied pressure just above it, he heard a sharp intake of breath. He ran his tongue down the flesh that hooded her clit, applying gentle pressure as he moved, and Erin's muscles tensed.

  Good, I've got her right where I want her. If I get her to cum first, then I don't have to worry about holding off myself if
I don't want to.

  When Jack's tongue reached the end of her clit hood, he poked the tip of it back up, this time under the hood. His hands came up and he drew the hood out of the way to reveal a swollen nubbin of flesh. He sent his tongue down onto it, pressing gently. Erin squirmed beneath him, nearly pulling herself away from the contact.

  His tongue pressed harder and Erin squeaked and jumped. This time, she got away from him. He pressed her down, his arms bent. His elbows came down just below her waist, arms bent so his fingers could get back to their previous location and his forearms pressed across her lower torso. He leaned into her enough to stop her from squirming away and, once again, drew her hood up to expose her clit. This time when his head moved down to it, he encircled it with his lips and used them to squeeze it gently.

  Erin tried to buck, but Jack put enough of his weight on his arms that only her upper torso moved. He applied suction gently and felt her clit stir in his mouth. His tongue alternately stroked and flicked it. Gentle licks with his tongue, followed by lightning quick light taps on the top of it, left her gasping and moaning. She continued to try to move her lower body, but Jack kept his weight on her, preventing her from escaping the pleasure he provided her.

  “I'm going to cum Jack,” Erin said.

  Jack continued what he was doing. When he felt Erin's pussy tighten up in preparation for cumming, he dropped his mouth down and drove his tongue deep into her tightening cleft. One finger kept her clit exposed while the other dropped down, pressed hard on the clit, and started moving in circles.

  Erin exploded. In his new position, Jack's head was trapped between her legs as her thighs clenched. He felt her pussy contract for a moment before it expanded and her juices came rushing out. He opened his mouth to capture them.

  She just hit the back of my throat, she's a squirter, he thought.

  He kept his finger working on her clit until a particular violent toss of her hips dislodged his arms. His tongue was still working on her pussy, but a minute later she stopped cumming. Her legs relaxed and Jack drew his head up.

  He looked at Erin. Her face was flushed and her makeup was mussed. She had a relaxed look on her face though, which was far more fetching than the locked in polite look she'd worn until just recently. Nate leaned over and whispered in her ear. Whatever he said caused her eyelids to flutter and her to murmur in a soft voice.

  “In a minute or two, I don't want to move just yet.”

  Nate leaned back in his chair, a satisfied smile on his face.

  Jack looked at Erin's relaxed body and couldn't resist. He traced a fingernail gently along the insides of her thighs. She squirmed deliciously and shudders ran through her body again.

  “or longer still, if he keeps that up,” she said.

  Jack glanced at Nate who had an evil smile on his face. Nate nodded at him so Jack continued to draw his fingernail along different portions of Erin's body.

  It was a full five minutes later when Erin finally sat up.

  “Enough of that,” she said, swatting at Jack's hand. “Lie down in the middle of the bed.”

  After he'd complied, Erin got on all fours. Her mouth was positioned over Jack's cock, while her ass pointed directly at her husband.

  She ducked her head down and planted a kiss on the head of Jack's cock. Then she parted her lips and pushed down. She kept her lips tight and Jack felt as though he were sliding into the tightest pussy he'd ever had. As he slid into her warm wet mouth, he could feel the tightness of her lips on his shaft while the top of him was in a looser warm, wet heaven. Her tongue darted in and started playing with his head. Somehow she managed to bob her head up and down on him while keeping her tongue in play.

  He couldn't help it, he glanced over at Nate, wondering what he was doing. Nathan was staring at his wife's ass, enthralled, as it shifted in time with the blow job she was giving.

  I imagine he's got a good look at her dripping pussy also, Jack thought. That would explain why he's so fixated on it.

  Jack closed his eyes and forgot about Nate, forgot about everything but the lips and tongue working his cock over. He realized that if he stayed that way, stayed focused on everything she was doing to him, it wouldn't be long before he came. He didn't want to do that, he wanted more of her before he finished so he opened his eyes again. The shifting, bouncing motion of her breasts caught his attention.

  He reached out and grabbed the nearest one. Erin paused for a moment, her rhythm unexpectedly broken by his touch, then she went back to what she was doing.

  Jack stroked her breast for a bit then let go and gauged its motion. He held out his hand, palm up, and moved it to where Erin's motions would cause her nipple to brush his palm over and over. The first time it did, she lost her rhythm again. After she'd gotten it back, she started varying the timing on her movements so her nipple was stroked irregularly. She seemed to be enjoying herself with it, almost as though she were playing a game.

  “Enough,” Jack said. “I want to be in something other than your mouth. Lie down on your back.”

  Erin drew her lips off Jack's cock. It emerged with a 'pop' as she continued the pressure with her lips until he was all the way out. She looked at him with a knowing smile on her face and shifted onto her back.

  Jack knelt between her legs. He placed the tip of his cock against her pussy and pushed the tiniest bit in. Then he looked up at her face.

  “Talk dirty to me?” he asked.

  He was amazed as her face flickered through several emotions before falling back into the polite mask he'd first encountered there.

  When she spoke, it was half-hearted and her voice contained a hint of mockery.

  “Ooh baby, ooh baby, do me.”

  Jack shook his head and looked at her again. She reacted to the look of disappointment on his face.

  “I'm sorry Jack, I shouldn't have reacted like that. You didn't know. I've never been able to talk dirty. It always comes out like the shoddy lines in a porn movie. The fact that I can't makes me react poorly when asked to try,” Erin said.

  “It shouldn't be that hard,” he said. “Just tell me what you want, and how much you want it.”

  “Like I said, it always comes out like cheap porn movie dialogue. I tense up and my brain locks up when I try.”

  “Alright then,” he said.

  I bet that with a little bit of effort on my part, I can get her over that, he thought, memories of Brenda fresh in his mind.

  He thrust into her slowly. He stopped when he had another inch inside of her. Then he drew back and pushed forward until he was that deep into her again. After he did that several times she looked him in the face.

  “What are you doing? Why are you teasing me? I thought you wanted to be inside of me,” she said.

  “I do want that. Do you want it?”

  “Yes, I want you inside of me.”

  “How far inside? You want me all the way in?”

  “Yes, I do. I want all of you inside of me.”

  Jack slowly slid his cock into her depths.

  Jesus, four for four. I love this MILF bit. They're all big enough to take me all the way in. I love being all wrapped up in their warm, wet, pussies.

  He continued sliding his cock all the way in and out of her, slowly. She started squirming beneath him.

  “Um, Jack? Could you maybe pick up the pace a bit? Maybe thrust a little harder also?” she said.

  “So, you want it fast and hard? With me all the way inside of you?” he asked.

  “Yes, I just said that, didn't I?”

  Jack picked up the pace and started thrusting harder. His hand went down to her clit and started stroking it. He paid close attention and when her pussy started clenching down a little and it looked like her muscles were tensing up, he drew himself out. He left only the tip of his cock in her, and stopped everything.

  Erin glared at him, fire in her eyes.

  “What the fuck are you doing? I was just about there?”

  “I just wanted to c
lear something up. How did you want me to take you? All the way in? Fast? Hard?”

  “Yes,” she screamed.

  A motion off to the side caught Jack's attention and he glanced that way. Nate was holding back laughter, barely. His eyes glinted and Jack was pretty sure that Nathan knew what Jack was doing.

  “Then tell me that. Get your temper up and tell me what you want.”

  “What, you want me to beg?” Erin said. “Just fuck me fast, deep, and hard!”

  Jack went back to slamming his cock in her pussy. He pinched her clit and held it. Within a minute Erin's back was arching and her pussy convulsed around his cock. While she was in the middle of her orgasm, he spoke.

  “See, you can talk dirty. You did just fine with it there.”

  Erin, trapped in the middle of her orgasm, couldn't reply. She stared at him in confusion though. Jack slid out of her and waited. When she finally calmed down, he caught her eyes.

  “You can do it, you just need to not think about it while you are. Take that inner monologue that's telling you what you want and verbalize it.”

  “What are you talking about?” she said.

  “Talking dirty. Let me quote you: 'Just fuck me fast, deep, and hard!' I think that counts as talking dirty, at least it had the same effect on me.”

  Erin's mouth dropped open and she glared at him.

  “You bastard, I thought you were trying to tease me, I hate teases. But you were really tricking me into talking dirty.”

  “Yup, and it's always easier to talk dirty after you've done it right once,” he said.

  Nate stopped trying to hold his laughter in and his deep chuckles filled the room.

  “He got you,” Nate said. “And it was pretty damn sexy from my point of view.”

  Erin looked back at Jack.

  “You said just verbalize my inner monologue?” she asked.

  “Is there a part of you that's thinking: 'I wish he'd do that' or 'Oh god, I like that' or anything else of the sort? If so, just let that go straight to your mouth, don't think about it at all, just say it. That's what talking dirty is really about, not filtering or censoring what you're thinking about, just saying it.”