Sharing the MILF List Ch. 05

byContrasting©

Alissa's eyes softened. "You are a dear man, Sonny Duncan." At that moment the food arrived.

We ate in a companionable silence for a while, commenting on the food. I thought I was biding my time but I actually waited too long.

Alissa put down her fork. "I have been thinking about our proposition and I have a great plan. I have to confess that I have discussed you with my sister, Melissa."

"Melissa? As in Aunt Missy?" Sammy had mentioned his hot aunt a number of times in terms I felt awkward mentioning to Alissa. I had met her when I was much younger and remember thinking she was hot, at the time. The terminology of a callow youth. "Melissa and Alissa? How cute!" I snickered.

Alissa did not smile. "Alissa and Melissa, she is younger than me by five years. I think, if you are going to give me to your friends, I decided I wanted to have Melissa there, to watch, to see you take me." She smiled but her eyes did not match the smile.

"You want your sister there? To see you take on five guys? What about Sammy?"

For a moment, Alissa's face registered surprise. "Oh shit, I never thought about Sammy being there."

"Have you been fucking him?" I asked, trying to assert myself, ignoring my earlier decision. Alissa ignored me.

She shook her head. "I was going to have her go topless but with Sammy there . . . well, no matter. She can be dressed. I would not want them to see . . . he will be naked, though, right? Perhaps you could distract him for most of the day and then Melissa could leave and he could arrive? That seems like the best solution. Saturday afternoon would be fine. That will give us six or eight hours to do the dirty. The main thing is that Missy has to watch but no one can touch her and she gets nothing, right? We just tease her all day, wouldn't that be a blast? And having her watch me, watch me, a, watch me, my gawd that would be fabulous!" Her eyes shone with excitement making her seem much, much younger. "I thought we could start with each of the boys taking me to bed and Missy could be tied to a chair and be made to watch while they fuck me. Then when each of them has had me, we get together and satisfy my obligation to you."

This woman seemed completely different from the one I seduced, the one I introduced to her son and my mother. And the one I had only moments ago separated from the pod as my designated pussy of choice. I wondered if I had made the wrong choice. Fortunately there was no record so I could still change my mind. But still, being shown to be wrong so soon after the thought entered my head was disconcerting. I thought about Laura Wills kissing Annie, her body twisting as she bore down on my cock and leaned into Annie's little hands squeezing her big tits and I got hard again.

"Oh and you will need to restrain Missy. You know, so she cannot escape. Perhaps my fuzzy cuffs? Or scarves like you did with your, er, with Cici." She glanced around. Then smiled at me again. "This should be much more enjoyable, don't you think? With an audience?" Then her face clouded, "Unless you were thinking of inviting your mother again?"

Caught off guard, I shook my head. I was thinking of this dynamic she was describing with Mrs. Wills in the mix and it muddled the whole picture. I had seen pictures of Melissa, Aunt Missy as Sammy called her, and she looked attractive enough, hell she was fucking gorgeous. But having her invited unceremoniously to join the MILF list seemed, well it just seemed wrong somehow.

"Well, that's settled then. Be at my house around noon or one, Saturday?" Alissa wiped her mouth with her napkin. "You will notify the boys. Have Sammy arrive about seven and I'll see that Melissa is out of the way by then."

We finished eating, she called for the check and paid it with a credit card, giving the handsome waiter a generous tip the fact of which she made sure to mention to me. She had to leave for the office but I went to the restroom so we would leave separately. She may not have been paranoid but I was.

It was with my hand around my cock at the urinal that I finally woke up and comprehended what had just happened. I had been . . . what is the right word? Not bamboozled. Not hoodwinked. Shit, maybe both! She had really worked me over. That was the word! Worked! I had been worked was the best way to describe it. Manipulated yes, but it was far too artful, too smooth to be manipulation. I had been worked and worked good. In the end, Alissa got what she wanted and I, I got what she wanted. I was not certain I understood all the issues with her work but as I thought about the thing with her sister, reviewing the conversation with Alissa, I realized there was a pernicious glint in the woman's eyes. Her look suggested a sisterly rivalry. She was using me, us and I was not sure I apprehended the full agenda and that made me nervous. What I did know and could feel in my bones was that I just lost control of the MILF list and that did not sit well with me.

Suddenly I had to shit so I went into the corner stall and sat down. I took out my phone and called Sammy. "Sammy, my man . . . ." I only got to that point when he interrupted me, panting.

"Dude, can I get back to you? I have Annie, am having Annie, how about later?"

I hesitated but then considered the effect on Annie to be interrupted or made to wait; the delay might make her more excited. "No, I need you now. Go in the other room." I waited, listening to the sound of a gagged woman grunting and whining."

"Just a sec, Sonny. I am going to give her some cock and then I'll be with you."

Rather than disconnecting, Sammy put down his phone and I heard him say, "Annie, spread your legs." A squealing sigh followed several grunts. A moment later she groaned and mewled and then came the sound of a closing door. "What is so fucking important that it takes me away from fucking Mrs. Kingston?"

I needed to shake him up a little, in order to get him to help. "Have you ever fucked your Aunt?"

Long, long silence; "What?" He said slowly.

"Have you ever fucked Aunt Missy, your Aunt Melissa?"

Another long pause, 'Fuck, Sonny, what are you up to now?"

I did not respond. I waited. I wanted to give him time to think of Aunt Melissa naked.

Sammy sighed. "Okay, no, but yes, I have thought of it, many times."

"Do you think your mom would tell her about us, about me and her fucking?"

Sammy thought for moment and then responded in a thoughtful voice, "She might. I have seen them flirting with the same man before and it was fucking embarrassing. My father never likes to be around them at the same time. Once Aunt Missy rubbed her tits on his arm with Mom watching and Mom nearly ripped his head off. It was embarrassing, he did not do anything, well, nothing I could see. But Mom was fucking furious. She and Aunt Missy get together and things get really weird, like space bends." Sammy chortled. "I guess it makes sense, space-time could get really perverted if you have two black holes that close together." He laughed and laughed but then sobered up. "Sorry, I just kill myself sometimes."

I waited till his applause for himself was past. "Sammy, can you get hold of your dad?"

"My dad, sure. Why?"

"Is there some way you can get him to come to the house this weekend?"

Sammy clicked into the phone a couple times. "Well, he has this project and he has talked about coming back and getting some things . . . I could ask him to do it this weekend. But shit, this is airtight weekend again, right?"

"I am working on that." I said, noncommittally. If I could not get my ducks in a row, I would cancel on the business-like Mrs. Honeywell and let her learn that way; but that struck me as terribly crude. I was looking for a more elegant solution to the forthright Mrs. Honeywell, something that would rattle her loose from the idea that she controlled the MILF list. "I guarantee you, Sammy, I will not leave you out."

"I guess I could invite him for dinner Saturday night, to talk about my future or something and then cancel while I was fucking his wife." Sammy chortled. "Don't feel sorry for my Father, Sonny, he is getting his. I found a picture of her on his phone, what a rack! She was nude with a cute little Santa hat on! A white woman with the most . . . well, with very impressive tits. Your Mom's tits are actually better which is amazing given her age, not that she is old . . . I mean . . . ." Sammy lapsed into a strategic silence.

I was tempted to get more details but demurred in favor of trying to figure out the logistics of getting Alissa Honeywell to understand that the MILF List was not business, it was pleasure and she should not confuse the two. "Call him, right now, and see if he can be here no later than Friday."

"Oh, I have a great idea." Sammy said, excitement in his voice. "He promised to go look at cars, implying he would buy me one. I'll get him here Thursday night so we can look at cars on Friday after class. He'll stay to get his stuff, he always likes to stay at the house just 'cuz it makes Mom so nuts; he told me that once. So that will make Mom nuts and she will be happy to get out of the house and do us."

"Don't get ahead of me on this. Just get him here, ask him to come to town but if he asks about your mom, plead ignorance. If he does not ask about her, suggest he should check with her first and insist that you need to know right now!" I waited.

Sammy breathed into the phone. "You know I looked up that series you told me about, The Pleasure Contracts; you are right, they are fucking great at not a bad price either." He fell silent.

I could feel the question lingering between us. Finally he spoke again.

"But that series on Literotica, are you sure that ain't us? The names are all changed and some of the details but shit it sure sounds a lot like us!"

I felt cold so I dissembled and distracted. "Isn't Mrs. Kingston cooling off? Maybe you better go finish what you started?"

Sammy agreed and hung up, but not before I heard the door open and Mrs. Kingston's keening in the background. He was so easy to distract. I finished my business which took while.

I was walking out of the restaurant after polluting the men's room when she called.

"Sonny, Sonny?" It was Alissa, right on schedule.

"Hello, Mrs. Honeywell." I said coolly. I did not like being moved around the board of life like a pawn. I wondered if she would hear the coldness in my tone. In fairness, I am not cold very often so I am not particularly practiced at giving that sort of hint so when she missed it, I could not hold it against her. On the other hand, if she had, a perfectly fine weekend could have ended up scuttled.

"Sonny, my husband, Sam, is coming back to town this weekend. He wants to look at cars with Sammy on Friday so will pick up some stuff on Saturday. He has some things to fix at the house and is planning to do that too, while he is there."

I waited. I was getting good at waiting, controlling the impulse to talk when I should be listening.

"I hate to cancel, particularly where Missy is flying in." Alissa ended the sentence as though there were more, much more to add. She waited for me to add it.

I waited. So far, this was her plan and I was not going to help her solve the problems she created. About that time, I realized that the woman had really ticked me off; funny how it took so long for that to sink in but I did not want it to interfere with getting to use her. I think I realized in that moment what I wanted and the chagrin I felt was caused by the recognition of how difficult it could prove to get Alissa Honeywell to fit with my ideal of mutual pleasure for all concerned. She seemed to like to control things, to move other people around like chess pieces. We'd see who moved who around the bedroom chess board.

"Sonny? Are you there?" Alissa sounded irritated and a little jittery.

"Yes." I said and nothing more.

"Did you hear what I said? Sam is going to be at the house this weekend."

"I heard." I said.

Alissa is not a stupid woman, not by a long shot. Her willingness to make an agenda and use me as one of the parts spoke of how she thought about me. For many reasons, I needed to change that. If her 'deal' at work was real, I needed her to take me seriously because everyone would key off how she responded to me. If they thought of me as just some dumb kid, it would never work. I needed her to fear me, just a little, just enough so it would appear as respect to those other people or her deal would never work for me. The truth? I smelled an opportunity and I wanted to make the most of it.

"Sonny, is there some place else?" She said, the first inkling that she had made a misstep tinted her tone.

"Yes." I said and hesitated. "No problem." I said, softly. "I think I can make proper arrangements, Alissa."

She sighed, actually sighed into the phone. "I did not want to ask Melissa to cancel . . . I do not know if she could get free for another weekend. And she would lose the ticket value if she canceled this late."

I knew she was hedging the truth. I hate to say she was lying. Maybe she actually did think Aunt Missy would lose her ticket but I knew better. Surely an attorney would too but then again, she was a partner and partners do not make their own travel arrangements. I had to keep my sexual paranoia in check. It could have been non-refundable, I suppose.

"Oh, and Sonny, I checked Melissa's flight times and she is getting in around four. Could you pick her up for me? I have an important meeting and Sammy will be with his dad. Could you do that for me?"

For a moment, I was stunned. At what point did I become her gofer? I felt denigrated but then the light shown on my benighted face and I saw the truth shining through; or at least the gleam of another opportunity. "Sure, Alissa. I would be happy to."

"Great! Thank you so much! See you . . . when?"

"Friday night." I said softly, "Or whenever I bring Melissa by."

"Oh no, can you find a place to stash her till we are ready? I need to tell Sam I am going to be gone this weekend so I will need a place to stay as well. I'll leave Friday so she cannot come to the house. I'll stay with her."

I almost said 'get a hotel' but kept my annoyance to myself. No time to be petty. The light got brighter and I almost laughed. The weekend was taking shape for me. "Sure. Where will you be, I'll come pick you up and deliver you to . . . wherever I find that will work."

"Great. You are such a dear, Sonny." And she was gone.

I hung up. I had some preparations to make. I was about to call Sammy when my phone buzzed and it was him. I answered and listened to the noise coming from the other end of the connection.

"Suck me, Annie, suck me and if you do a good job, I will fuck you, again." Sammy was saying.

I heard the grunted assent which sounded like it came from a woman with her mouth full which it probably did.

"Sammy?" I said softly.

"Hey Sonny, we are good. Dad called Mom and just got back to me. He'll be in Thursday. So Annie will not get any of Sammy this weekend."

I regretted that she likely heard that but no matter. Things could still change. "Don't count on it, Sammy. This weekend is shaping up to be a good one."

"Aaarrrrgghhhh. On the bed, Annie, you deserve it whichever way you want it. Gawd, Sonny, this woman is amazing. She is on her knees pointing her ass at me and I cannot tell if she wants it in the ass or the pussy! I love options! Gotta go!"

"Wait. This weekend, when I ask you if you want your mom, say no, pick the other woman, regardless of who I offer you."

Sammy paused in his departure. "Other woman? Sonny, what are you up to? Oh, forget it. I got it. Don't choose Mom."

"Right. No matter who the alternative is, do not take your mother." I said and disconnected.

I called the other guys with the same message; be at the Wills' house around ten Saturday morning and do not pick Mrs. Honeywell when given a choice. Despite their dubious tones, all eventually agreed.

Landon asked, "Why would I ever say 'no' if you offered me Mrs. Honeywell?"

"Because I asked you to." I said, unwilling to disclose what I was planning, in case it did not gel.

When I spoke to Brent, something seemed off. He agreed to my simple request but was quiet after and I stayed on the line to see what was what. Finally, he spoke into an odd silence you never get between guys.

"Sonny, I know I was a little irate the other day . . . you know, about you fucking my mom . . .?"

"Yeah." I said slowly, wondering where this was going.

"Well, I was wondering, you know, if you would mind if I, you know . . . . " He trailed off but I could see the trail a mile off.

"You want to fuck your mom?" I said and waited but he did not respond. "You are asking my permission? You just don't get it do you? These women, our mother's, they fuck whomever they like, with or without my permission. Turns out they fuck and like fucking more than any of us imagined."

"Ah, okay. But that is not what I was asking. Not really. I was asking about your mom. Would it be okay if I fucked her." He said. But there was more. "But Sonny, she called me. Your mother, I mean. She invited me over tonight."

I cannot really tell you what I felt but it was damn uncomfortable. Confusion and guilt and excitement all boiled into one thing that did not fit in my gut or mind very nicely. I remembered the sight of his great cock sliding into my shaking mother! I shook my head; if I started fucking my own mother regularly, then next thing you know Georgia would want . . . I let the thought dribble away. "She called you?" I asked.

Silence. I imagined Brent nodding his big head. "Yes." His voice came belatedly over the phone.

"What did you tell her?" I asked.

"I said I would have to call her back and hung up. Shit, Sonny, it scared me. She scared me. She sounded all . . . a . . . ready. You know what I mean?"

I had to smile at that. I knew that feeling! And then lightning struck. I love that feeling when the perfect solution to a complicated problem suddenly appears like an angel, which in this case was a naked angel with big tits. "Weeeeeeeeeell," I said, drawing the syllable out. "Isn't that interesting. Tonight?"

Again, silence.

This time I said , "This ain't a video phone, Brent, you have to talk."

"Right. Yes, she said the girls were going to be gone and . . . " his voice rasped over the phone but then he said in a small voice, "she asked if I was doing anything interesting tonight."

"Call her back and tell her seven-thirty. But Brent, wait a tick. Do you think Mrs. Rossini will be home tonight?"

The silence this time was much, much longer.

"Sonny, what are you thinking?"

"I am thinking we should swap Mom's. You fuck mine at my house while I am fucking yours at your house."

Another silence. "Why?" He asked.

I chalked it up to just being the only thing he could think of because Brent was just not stupid. I changed tactics. "Brent, what if we fucked your mom this weekend? You know, made her airtight?" I said.

Now the fucker really couldn't speak.

I waited.

When he did speak, he sounded angry. "Is this about your mom calling m. . . ."

I interrupted him with a harsh, "No! Of course not. Brent, fuck her, don't fuck her take her ass do what you like. Mom is a woman and an adult and if she decides to fuck us all on her own, that is entirely her business. And absolutely none of mine!" I felt twinges of other feelings but decided to only express the most liberal and enlightened one, at least in the opinion of my cock which was trying to make its own hole in my pants. "Listen, Brent, I want to fuck your mom tonight, while you are fucking mine. Do something, say something to let her know where you are and what you are doing. But try to make it seem like you are trying to keep it from her. If you can be that subtle," I smirked to myself at the idea of blunt Brent being subtle but even if he wrote it on his forehead that he was off to fuck Mrs. MILF, I thought I could fit that into the picture. "I will surprise her and if all goes well, I think you can have your mother tonight as well. But Brent, you have to know that I am lining her up to do the Annie this weekend."

Report Story

byContrasting© 5 comments/ 106369 views/ 67 favorites

Share the love

Report a Bug

PreviousNext
6 Pages:12345

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel