Extending the MILF List Ch. 14

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How Much Sex Can One Man Have? Part 3: It's Raining Pussy!
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Part 14 of the 26 part series

Updated 06/07/2023
Created 10/16/2014
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Chapter 14: How Much Sex Can One Man Have? Saturday: It's Raining Pussy

I woke with a ghastly headache. I remember waking with the theory of vomiting all drawn up with differential equations and everything but without the requisite energy to get to the bathroom. I hoped if I held still, the urge would leave. I eventually went back to sleep. By nine I was awake. My phone rang around that time but I don't remember if it woke me up or if I was already moaning. It was D. Debra Hamilton.

Okay. I felt a little guilty. I had not contacted her since Sunday. Well, fuck me, I'd been busy! Oh, wait, that wasn't right, I lined up Brent to fuck her. Thursday was it? Right, when I ran out of starch before I ran out of pussy. Small wonder I forgot that night. Oh, well, I did fuck my sister in front of everyone and Tawny orgasmed like she'd planned it perfectly. Maybe she had.

"Hello."

"You let me down, Mr. Duncan."

"Excuse me?"

"You let me down. I don't fuck your friends unless you are there to watch. I guess you didn't realize that. You have to see them put their cock in me. Didn't I make that clear?"

"What about my sister?"

"You were there. You could have had me that night and you chose to watch me do your friend and your sister. I was...I was horny and ready but you were so cool, so distant. I thought I could make you jealous but once I got started, I realized I wasn't going to quit. So I just went the whole way...what the fuck am I explaining myself to you for? You fucked my mother. I am pretty sure the scales of justice weigh in my favor."

"No. Apples and oranges, or more literally, dicks and pussies. They may fit together but they are not the same and no way I am trading orgasms with you." I waited for a response but got none. "So? How was it? Did you like Brent?"

"I told you, I won't fuck your friends without you there, to watch."

"Why? You need directions?"

"Jesus in a cup, Sonny, do I have to spell it out for you?"

"I was in a spelling bee once and they gave me ppbbbttts and I got DQ'd for having an extra 'B' in it. So I am not sure spelling it out for me is going to help. What time is it?"

She ignored me. "I get a thrill having you there, knowing you handed me over to your friends."

I knew that wasn't all there was too it. I was being worked. She'd confessed to a fear of losing control...oh, wait, she confessed that to Dori, not me. I was getting confused. She'd insisted that when I gave her away, I had to claim her back, sort of like pulling her back from the edge. I was sort of like her safe word, you know when people want to yell "no" and mean "Don't listen to me, do what you want!" Which means "do what I want" and that's where things get tricky. They need to have a word like hippopotamus it you start to do damage, hence a safe word. I never use them, too confusing and fuck, I'd forget mine. I like the real dialog and not the play acting sort of sex. When I fuck, its always real.

Nonetheless, I realized I was going to need to participate in D. Debra's endeavor to fuck all my friends. I was pondering how I was going to present that when I remembered what she said. There, that was the ready made excuse and a pretty good one. I had to push back a little though.

"I wasn't there the other night. You know with..." Suddenly I got a sick feeling in my gut. What if she realizes Sam is Sammy's dad? I had a brief sense of relief that I hadn't seen fit to hand her off to Sammy yet. Suddenly, my more or less ideal intention to satisfy Messy Melissa's fantasy of doing a father and a son at the same time got a little bit urgent. Then I realized I was being a racist prick, just because they were the same color doesn't mean they're related and why would I think D. Debra would think that? Unless they fucked the same...I needed another black guy to fuck her, oh, been there, done that. Thank god for Rodney. And Ahmay! Wow. What was she saying? I needed to pay attention!

"You were busy. Hey, I was going to ask you about that. What is it with you and black men? You keep handing me off to them. You have a thing about black on white sex?"

I groaned. Audibly. I realized I had no idea what D. Debra understood about my sex life and what she suspected and what she knew for certain. So I changed the subject. "Play practice today?"

"Two." She did not seem perturbed by the shift in topic.

I was going somewhere with that question. "So you didn't do Brent?"

"No. I went with him to his house and when I realized you weren't coming, I left."

"Did he show you his dick?"

"What?"

"Never mind. Listen, what about now? I mean, surely you didn't get all the love scenes out of the way already. You could go in all fuck stinky and your gay opposite can smell sperm on your breath and maybe he'll kiss you for real."

"Sonny! God, don't you respect anything? I'd never do that to..." She started to giggle. "Shit on a pancake, that might be hilarious. Do, do you think your breath will smell like come if you swallow or only if you spit?"

"I am sure I don't know. My breath is never going to smell like sperm but yours might. Why don't you figure out a way to test that out? I bet Chris would help you." I sat up and the room didn't whirl and the bed didn't dance. I was feeling better. The relief was so profound I dropped the phone. I fumbled with it and got it back to my ear.

"...might be good. I like that oozing feeling...why did you ask if I saw his dick?"

"He's hung." I answered the question honestly. "He packs more meat than Iowa."

"Oh really? Big is he? You wouldn't tease me, would you? I do love a big cock."

I thought of Sid. The idea of him squeezing his trouser monster into D. Debra buzzed between my ears and I missed whatever she was saying next.

"...can call me back."

"Call you back?"

"If, what was his name? Brad?"

"Brent."

"If Brent is available and would like a little Dee Dee before lunch, call me back. Sonny, are you whacking off?"

"No. I'm wanking."

"Well quit it, its rude to masturbate while you talk to a woman on the phone."

"When should I masturbate then? When I talk to a man on the phone?"

"Sonny, oh fuck it. Call me if you have a little lovin' for Dee Dee. It's nine. I can be table ready by ten."

I laughed, thinking of her bent over her mother's table. I shuddered.

"I'll get back to you either way." I hung up hoping that Brent was available. I figured I'd have a taste of Dee Dee and study this afternoon till it was time to display my prowess with Mrs. Honeywell.

"Ten? I'll call you back." I hung up.

The phone rang in my hand. It was Alissa.

"Sonny? I, I can't make it tonight. Something came up. I mean I won't be available, for Ahmay."

Her voice sounded weird.

"You okay, Alissa? You sound weird." Thinking and speaking are often the same activity for me.

"I'm fine, just distracted. Sid wants me to attend a cocktail and dinner for him with some people. I don't know how long I'll be but I'll call you if I can get free earlier. Ciao."

She rang off and I sat staring at my phone. My stomach's rebellion seemed to have quieted. I had a disquieting thought that I had dreamed of vomiting and wondered if I did. I looked around the room and saw it was in pretty good shape. I sniffed and smelled nothing. I felt a moment of regret that Alissa had called off our little menage a three for Ahmay. But then I considered the amount of pussy coming my way and figured a breather might be good. Nice thought, fat boy.

I called Brent.

"Sonny, fuck you. What do you want?"

I decided his crabbiness was compounded by being neglected by my girlfriend. He had seen his Aunt riding the rail while I rode her and had jumped to some curious conclusion by way of far too many steps in the proof to make Occam happy. Brent never saw things in the simplest terms. For him, everything was complicated but then with a cock that size, it is good to presume to need more lubrication than the rest of us depend on to keep things smooth.

I hesitated too long, still in my own head.

"She wouldn't fuck me without you there. She said no one eats pussy like Sonny Duncan and she had no interest in fucking me unless you were there to watch. She said you made it so hot, so sexy when you watched over her and made sure she had good orgasms. Like you can do that! Shit, dude, she talked like she was in love with you."

"In love? That woman? Hardee har har. If she was in love with me, why was she there with you in the first place? Did you show her your dick?"

"What are you implying?"

"Nothing. Well, I'd bet even money she'd have reconsidered if you showed it too her."

"What was I supposed to do? Once she said, not without Sonny, I should open my pants and flop Mr. Hungry out on the table and wait for her to faint or give me a bid per cubic inch?"

"Yes. Show her the cock and she'd never have left with you untried."

Brent growled. "Had my Aunt lately? Why are you calling, anyway? You just want to lord it over the rest of us that pussy falls in your lap, no matter what you are doing. Fuck you."

Brent was not in a good mood.

"Parents still screaming at each other?"

"Yes. They're leaving tonight. Spending a night or two in a no-tell motel before Dad leaves on Monday."

"So? You have a verdict?"

"Are they staying together? They'll never get a divorce. Well, they might if Norma does both of us, Dad and me I mean. I am still suspicious that Mom will put up with little sister banging her whole family."

"I suppose I owe it to you. I should have done this the other night but I had a distraction to deal with. I'll get D. Debra and you can do her at your house this morning, if you're still interested that is."

Silence. I waited but it was just soaking in that saving myself for true love wasn't going to be necessary, Alissa had waved me off and that meant...I could go have a piece of Dori if I wanted. I wanted. "Aren't you going to say something?"

"You're not trying to distract me for some reason are you, Sonny? You have had my Aunt at your house...god, she can move back in!"

I had a thought about that too but kept it to myself. I wondered where Norma was. I shook my head to clear it. Focus. "So? Shall I tell her you are up for it? D. Debra I mean. I am sorry about the other night, I had reason to believe she'd open up her little shop of whores after hours. I had no idea that she'd buck the trend."

"What trend is that?"

"None for Sonny and some for everyone else."

"Oh for shit's sake, are you complaining? Really? Poor fucking Sonny!" Brent really woke up on the wrong side of the bed.

"Okay. I deserved that. So? What's it going to be? To do D. Debra nor not to do D. Debra?"

"I, I was going to bitch at you for the other night but Landon pointed out that all roads lead to Sonny when it comes to the pussy that it swirls around you but you share. You ought to bone his girl once and see if he is still so philosophical about it."

Goddamn if Brent didn't prove prophetic. I was hard. Nice to know I wasn't out of starch.

"Come on, Brent, make up your mind. I am not going to push D. Debra on anyone. You don't want to do her, I'll call Sammy."

"No. No, shoot no, Sonny. If you think she'll go through with it this time. You should have seen Mom when D. Debra strutted out of the house. She didn't know whether to clap or whistle."

I didn't get that but left well enough alone. "Come on, Brent. Christ, Hamlet was faster to decide to take revenge than you are."

"Is this revenge?"

"I owe you for the other night. I know that. I sincerely thought D. Debra was a fair trade."

"You mean for my Aunt Norma? You already got my Mom and you want my Aunt too." You going to collar my Aunt too and hook her into your little Sonny Harem?"

Hell of an idea. I had to give that some serious thought.

"God Brent, have you got indigestion? Go back to bed. I'll find another cock for D. Debra. Forget I asked." I was impatient because I had something I wanted to do, someone I wanted to do and I had just the person to do it with.

"Hey, no, fine. Bring her by."

"We'll be there by ten or so. She has play practice at two so you have four hours to rub it down to a nub."

Brent snorted and hung up.

I jumped up, all fired up to take action and remembered I wasn't done. No Ahmay, no...uh oh. I forgot about my surprise guest star. I needed to call Mrs. Bickerstaff and let her know we were on hold for our demonstration threesome. I did that first, she seemed distracted and took the news calmly, without a ripple. I called Ahmay. She sighed and said I needed to quit making appointments I cannot keep. I thought that was a little selfish, seeing as how I was doing her a favor but let it be. Not like I was being put out. Ahmay was auditing and her eyes made the sex with Portia that must better. I thought about...I put it out of my mind.

Finally, I was ready. I had been pacing in my little room, three steps to and three steps fro. I called Dori Hamilton. "Mrs. Hamilton?"

"Sonny! Dee Dee is upstairs."

I almost left a message with the mother but thought that would foul up communication. I grunted in amusement at that idea. "You said I should call before I come by. I want to come by at one or two."

"You do?"

"Yes. I do."

"Is that wise?"

"Dee Dee has play practice at two." I thought about telling Dori about her daughter's Saturday morning plans but demurred.

"I mean, is it wise for you to come by?"

I was fairly panting. I sat on the bed to steady myself.

"I want you. I do. I don't care about anything else."

"Sonny, well goodness, I want you too. I am not going to try to be all noble if self-denial is noble. I, I don't think we should. I think we should only meet if we have someone else there or we'll, you know what we'll do."

I knew and I wanted that to happen. Again. I got her point. Not really, though I understood her reluctance but she still thought Debra had a problem with her. I grinned. Brent had a great idea but in this case, I'd prove too slow. Dori was talking.

"I'll be here. Just call if you can't make it. If I think Dee Dee will be here, I'll be sure to answer the door. Otherwise, I'll just leave it unlocked. We can't, again, I mean we shouldn't. I'll find someone to be here with me, so, so we don't, don't do it again. Or you can bring someone but we have to stop, you agree right."

I nodded. Nodded again and found my voice. My heart was making it difficult to talk, trying to climb out my throat and all. I was excited so the lie came to my lips easily and I barely noticed.

"I do, yes, of course I do. You find someone. You do that. I'll be there as soon as I can." I didn't get her reluctance but left it intact. I felt the quivering desire in me surging so strongly I didn't care what happened so long as I got between her MILF legs and plunged my cock into her MILF pussy. God, I was crazed.

I hung up, showered and realized I hadn't called D. Debra when I said I would. She was peeved when I told her ten was good but did not argue. She did say I was lucky I wasn't calling to tell her it was a no go because she was half ready already.

She did not come out when I parked outside her house. I had to call her since I didn't want to face Dori right then. Debra told me to meet her at the door. I was there when she opened. She told her mom bye, that Sonny was here and we left. We got into the car and D. Debra looked around.

"Is this yours?"

I realized my car was new to her and she hadn't seen it before with me in the driver's seat. "I got it as a perk for some work I am doing. I am picking up people for a law office and they provided me a company car."

"Is, is Brad pissed off at me? Is he going to put a knot in his dick and tell me to fuck off?"

"No. It's Brent and he's not mad. At least not at you. Me, maybe, but not you."

"Why would he be angry with you?"

Why indeed? "That, my dear, is a story that is way longer than I can tell before we get to his house."

"His mother and father are nice."

I grunted. We rode the rest of the way with her reciting lines and checking them against her script.

At Brent's house, I got out and opened her door for her. I walked her to the door and Brent opened it before we touched the doorbell. I introduced them, again. They regarded each other like two dancers when one is a breakdancer and the other does the tango. If I hadn't been so distracted by my own forgetfulness and my obsession with D. Debra's mother, I'd have been a little worried.

Brent finally told her he was sorry about the other night, which made no sense since he did nothing. D. Debra looked quizzically at me, confused. Brent was apologizing for nothing. He looked at me.

"Sonny, I want to do her on the pool table. You know, like that time...? Oh shit."

D. Debra looked back and forth between us.

"If you are worried that Sonny has misrepresented his intentions with me, don't be concerned. He's fucking my mother and I am fucking his friends. If I found out he was doing your mother, I doubt I'd be surprised. He isn't, is he?"

Brent's face went all bland and if Dee Dee knew him, she would have seen right away that something was up. "Not right now." He said with a half laugh. "Please, let me take you downstairs. Have you ever had sex on a pool table?"

D. Debra regarded him with a flicker of interest and shook her head.

My phone rang so I let them go without me. It was Landon.

"Sonny?"

"Speaking. What's happening. How is your little corner of pussy heaven this morning?"

"Cramped and crowded which is why I am calling."

"Oh?"

"Mom is tied up up stairs but Darlene won't stay tied up. I just want to watch some basketball and chill, alone, you know. Darlene, don't tell her I said this but she is terrible to watch sports with. She bitches about color combinations and says guys look gay doing things and oh, it is just terrible. She calls them 'sweety' and 'honey' when they are shooting free throws and, well, it just sucks. I just want a calm, easy day and I was wondering if you'd take Darlene off my hands for the day."

I looked at my phone. I decided to dissimulate.

"Calm and easy with your Mom tied up upstairs?"

"Yeah, I fuck her during halftime. She never knows when half time is and the waiting makes her crazy, its like foreplay for the mind. When its time, god, she's usually ready."

"Darlene not so much?"

"No, she insists on watching sports with me but Christ, I just want her to leave me in peace. And no, she won't just suck my cock. That's distracting anyway. I already tried it and it alters the whole sports watching experience."

"I expect it does."

"So? Will you take her off my hands for the afternoon anyway?"

At first, my heart sank and my cock objected because I was thinking of Dori. Then, I realized things were lining up. Dori might fuck me if Darlene was along. Maybe not, too. I was confused about the whole, have someone present. Was she thinking chaperon or something? The old, keep one foot on the floor rule? If you fuck from behind, you can keep all four feet on the floor but the nuns never considered anything but the missionary position, I suppose. I couldn't tell if that was a contradiction or not.

"Sonny?"

I realized I'd been chasing thoughts in circles.

"What?"

"When I say, take Darlene off my hands, you know what I mean, right?" He hesitated but not long enough for me to edge into the thought. "I mean fuck her. She, god, Sonny, she talks about having you come do a foursome with us, make a night of it, like it'd be some social event. I think she's daft sometimes."

"You getting crowded?" I was taken aback that he'd offer his woman up like that. I had to balance that out. Then it occurred to me maybe he was angling to get his shot at D. Debra. Ha so?

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