Extending the MILF List Ch. 01

Story Info
Doing a MILF's sis-in-laws as a favor.
22.1k words
4.62
299.3k
381

Part 1 of the 26 part series

Updated 06/07/2023
Created 10/16/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Contrasting
Contrasting
3,179 Followers

Doing a MILF's Sis-In-Laws as a Favor

My Blond Ambition-the tease begins

—After many episodes with lots of action and setup interwoven, it is time to take a little breath and bridge back to those before that lead to here. This is all about the characters and the plot and examining how everyone is relating to the end of the MILF list and beginning the process of extending it. If you are new to this series, Making the MILF List and Sharing the MILF List (in that order) are the precursors. This whole series is based in the TABOO section so if that is not your thing, be aware. It relies on variety as well. This story addresses some of the unresolved issues from the previous series and establishes the basis for this one. Please vote and leave comments as you can. Feedback really helps direct the story and fix the issues and ambiguities that may affect the flow of the work, so it is really appreciated. Thanks to everyone who supports the MILF series and the adventures of Sonny Duncan. -C

*****

The day after my mother boarded a plane for Hong Kong, I saw her.

My assumption, well, not mine, nor was it an assumption exactly... my understanding, my conclusion was that two people may have a chemical connection or they don't. When you have it, one or the other or both of you will know it and right away. What is more, knowing it, people react differently. There are all kinds of different reactions. You quiver and shake like that man in Nabokov or you ignore it, reject it, or deny it. The "it" in that sentence is the connection, the shivering connection between you and that other person and if you are fortunate it matches your gender orientation and you don't have to deal with that whole issue. One of the sure telltales of that connection is utter and complete confusion. It is like the volume on the rest of your life is turned down. Or like everything else you see with your eyes gets blurry or muzzy somehow, which may be another way of saying that she (my orientation) takes on a glow or a hyper-contrast to the rest of the world.

D. Debra Hamilton was coming out of the engineering building. I was going in. I was running an errand for one of my professors since I really had no business being in the engineering building which explains why it was so late in my time on campus before I saw her. She was a fucking engineering student, a Junior; can you believe that? A woman who looks like that, smart enough to be an engineering student? But I am getting ahead of myself, again, some more. I was coming up the steps to the front door and the double doors opened and there she was, framed by the dim interior. It was like I had been caught in a spotlight trying to escape prison. The fight or flight response hit me like lightning. I could not move, I could not breathe right, thoughts bumped into each other and I thought... no, I quit thinking. I went blank and all systems stuttered to a stop.

If she had kept walking, nothing would have happened but she stood there and I swear the sun poked out of the clouds that blanketed the day and for a moment, she glistened with sunlight. She stopped, arched her back and lifted her chin, closed her eyes and held that pose for a moment just bathing in the light and the sudden surge of warmth. She thrust out her impressive tits bathed in sunlight, her mane of blond hair flowing behind her like a cape. I was starstruck.

My cock snapped to attention.

Since making the MILF list, I had not had that experience much, not with the women on campus and by that I mean women my own age. The wild MILF had sort of absorbed my attention but that is not right. It was the domestic MILF, the MILFs I knew and loved and recently fucked that had been the object of my desires and machinations. But here, right before me, shining in the evanescent moment of sunlight, stood a woman/girl who aroused me on sight.

D. Debra Hamilton. She introduced herself to me after I made it to the top of the steps. The flimsy crowd current flowed around us easily, eyes averted, as though they did not see what was happening. D. Debra Hamilton stood still, a purse over her shoulder hanging by one considerable hip, a small lap top in one hand and three or four books tucked under her breast in the other. Her golden skin glittered in the sunlight. I stopped before her and just waited. The sunlight faded, her eyes opened and she regarded me with blue eyes, clear and startling.

She did not smile.

I so wanted her to smile.

"Can I help you?" She asked.

I remember my brain grinding into action then with a simple observation that she was not moving away from me and there was no fear in her eyes. No, my thought was "beautiful eyes", at the time. Suddenly all the filing clerks in my head were frantically looking for just the right thing to say but, and I give all the credit to the various MILFs whom I had pillaged in the past few months, I did not panic and try to be too clever. I heard the tuning fork and harmonized perfectly.

"As the most beautiful woman I have ever seen, would it be inappropriate of me to ask you to have coffee with me sometime?"

"Beauty may only be skin deep." She responded.

I so wanted her to smile.

I shook my head. "I am sorry. Was I not speaking English? I sometimes do that. Let me try again. Would you have coffee with me sometime?"

For a moment she just regarded me. Then she licked her full, lower lip, the merest tip of a pink tongue running from left to right, stage right. I think I remember gulping and my eyes focused on her lips before looking back up into her eyes. She lifted the slight computer case, turning it so the side was between us, like a castle wall. I thought I had cooked the goose, no golden egg for me.

"In the side pocket, I think I have a card." She said. Her voice was melodious, a mellifluous tune that needed no words to fully entice me and excavate my delight. She held the case up till it wavered while I looked dumbly at her, utterly uncomprehending. She finally grunted and lowered it. "I have a card. A private card, it is in the side pocket I think. Or I will have to get into my purse and, my hands are full and so are yours. Oh."

That little luscious syllable told me something wonderful and my mind finally engaged. She had not seen me enough to know I was carrying an old overhead transparency machine. Something had distracted her to the point that she invited me to use hands I did not have free to use at her command. I set the machine down. "I understand now. Try again."

There. She smiled! I was so sure the sun had come out again. I went blind to the world. I tingled. I quivered. I felt warm all over. She lifted the case again and I fumbled with it till I realized (that is, till I looked down from her eyes and actually saw what I was feeling) that it was zipped. I pulled the zipper open and reached inside the side pocket. That is not as easy as it sounds. I think my hands were shaking. I found a lone card. I extracted it and she lowered the case, which lured me down, bending beside her while I tried to rezip the pocket. My head was even with her hip and I could not breathe at all when I realized how close I was to the woman's crotch. That may have been because I was bending over. I held my breath so it would not seem like I was sniffing, sniffing around. I remember consciously holding my breath but the smell of her wafted into my nose and tickled my imagination, my fancy, and my cock. I fumbled with the zipper and closed it. I stood up as the world turned dark and wobbled, swimming till I gasped for breath. If my face was red, it was not from exertion. As hard as my cock was, I should have been pale as a ghost.

We stood staring at each other for a few moments. "Well?" She said.

I looked at the card. "D. Debra Hamilton." I read. That was how I was introduced to the love of my life and new torment.

"Yes. And you are ...?"

I groped, internally. I knew I had a name. I knew I knew it but I could not find the syllables. They slithered and slunk out of my reach, dodging and grunting with delight at my dumb struggle. Finally I caught one. "Duncan. Sonny." I finished, relieved because I knew that was mostly right.

"Duncan Sonny? Pleased to meet you." She still made no motion to leave.

"No, not, ah, my name is Sonny. Sonny Duncan." I nodded. "That's it. Hell, I knew I knew my name. Do you always interrogate your prisoners this way, with such penetrating questions?"

"What?" Her eyes widened.

"After you capture them in the gravity well of your orbit, do you interrogate them like this? Demanding they tell you their name." I looked hard at the card, turned it over. I wanted her to smile but when she did, I was unprepared for the perfect white teeth, the flash of verve in her eyes.

"You talk like an idiot."

"Oh good, then you see right through the elan and debonair facade that so dazzles everyone else."

"Especially the gay guys, I am guessing." Her smile broadened.

I snorted. Suddenly all the incapacitating qualities of being lovestruck seemed to be overlaid with the instincts I had learned with the MILFs, seducing them, making them, pleasing them, and sharing them. That shallow instinct, so recently developed proved useful and more natural under this sort of pressure than I would have ever guessed. "What do you know of gay guys? Are you some sort of new twist? A missionary for the missionary position?" The words blasted past my teeth before I had a chance to review them and edit them for content and control them for some as yet unknown objective. Like I said, I blame the MILF List.

She left me standing there. She turned and walked down the nine steps to the next landing and then turned to face me. "Call me." She said. "Soon. I am between boyfriends and that leaves you about two days before I find a new one."

Then she was gone. I was utterly cock struck. People moved quietly and mutely past me and my antique projector. One of the professors was going to use it as a demonstration of optics or something. I picked it up and completed my errand. Only after I was sitting in my car, er, mom's car, she isn't dead, after all, just in China, Hong Kong actually and I did not yet know if they were synonyms or not. I sat looking at the card. It read "D. Debra Hamilton" on one side with her cell number on the other.

I dialed the number. That same melody of tones answered. "Hello, the is Deedee Hamilton."

"Hello, this is Sonny Duncan calling. I would like to meet you for coffee tomorrow."

Silence. More silence.

I did not panic and say anything more. I had been direct and to the point. The coin was flipped, the die were cast.

"I only have time at seven-forty. Seven-forty to eight-thirty. Can you make that time?"

Early. I almost said that. Wednesday. The day before Thanksgiving. I was supposed to help my sisters shop for Thanksgiving. I'd reschedule. Or something. No, that was today, Tuesday evening. So my schedule was perfectly and wonderfully clear! My heart hammered, my head pounded. Heads. "Of course. The Best and Big at twenty to?"

"The Best and Big Cup? That would be perfect."

I was certain I heard pleasure in her voice. "Right, the Big Cup." I mumbled, calling into my mind the woman's incredible edible tits, the ones that dominated her profile and made "statuesque" seem a pedestrian adjective.

"See you then, tomorrow." She disconnected.

That was the afternoon, Tuesday afternoon and after half a day brooding about my sisters, now I had something that muscled them and their concerns aside. I did not intend for this to happen, to meet D. Debra Hamilton but it happened. It did. I remember.

But me go backwards for a moment. Back to the moment I picked them up at their stop in Mom's car, after dropping our mutual mother off at the airport to go meet the world's largest cock and sit on it. Our mother was off chasing big, no huge, no monstrous cock. It was Monday and I was about to shift from the MILF list to the DILF list. At least, that was what I thought at the time. I always think too simply about such things, though.

"Blisters, have you been having sex with mom since you were eighteen?" That was the moment when things began to go awry and my enterprise of great pitch and moment lost its label of "action". The MILF list ran into my sisterly obstructions.

I was driving Mom's car. Georgia sat beside me and my other two sisters, Dalia and Tawny were in the back of the sedan. I asked the question into the clucking of my hen sisters and they all went utterly silent. For a few traffic lights, no one spoke. I had surprised my three sisters by being the one driving my mother's car. I had just told them our mutual mother had flown off to ride a monster cock in China or something to that effect. Well, actually, I guess to be perfectly accurate, I had not cued them in all the situation at all but had responded to their question about why me and where's Mom with this perfect icebreaker of a question. I was so proud, utterly unaware I had just run off a cliff.

Finally Georgia who had been staring straight ahead, spoke but not to address my question. In fact, as she talked, I could not tell for certain who she was talking to. She was not talking, she was confessing. We, her three siblings, were her confessors.

She told about arriving home after an aborted date that Friday night to the sound of our dear mother crying out my name; Sonny! Sonny, oh Sonny, finally you are, you are, oh, you can have me any time you want me. Please, please put it in me. Oh yes, like that! Deeper, harder, Oh yes! Oh my darling son!" So Georgia claimed were the words she heard cascading out of Mom's room.

Well, not just my name, as it turned out, but a much more involved dialog. My dear sister, Georgia, who we call variously, Nova, Brimstone, or Lava, she of the red hair not being shy or retiring in any of her cells, not one, stormed into my mother's bedroom certain she would find her brother planted firmly between her mother's legs. Of course she had no idea what she would do thereafter, regardless of what she found but in she charged nonetheless. With Nova, impulsive is an understatement.

She found no brother but only one naked woman, on her knees, eyes clinched tightly closed, a vibrating dildo extending like a tail behind her while she vainly sought to manipulate it. According to Nova, mom did not even open her eyes or seem aware of the open door and the presence of a third party in the room. Given the sequence of events, we were able to construct a likely explanation for her behavior. Our demure mother held her pose and continued her activity till she orgasmed and rolled onto her side. When her heavy eye lids uncovered her eyes and she saw, not her son whom she had been awaiting but her eldest daughter, she screeched and sought to cover herself.

Georgia, mortified, skedaddled without even closing the door. She recounted standing in her bedroom, the door closed, staring at it like she was waiting for Jason to find and cut her into little, spurting pieces with a Texas chainsaw. The longer she waited, the more she thought that might be a better fate than emerging into her own house from that room to face her mother with those words between them... with "oh, my darling son" echoing in her ears from her mother's lips. Her head was full of plans to move out and how she would manage to pay for rent and food and all the other bills that she did not face living at home with her heretofore placid family. She was only beginning to recover her wits and review her mother's words, spliced with her brother's name which, since she said "darling son" could not be mistaken for some other lucky "Sonny" of more anonymous acquaintance. Her mother had been masturbating to the fantasy of fucking her own son!

"You can imagine my, uh... " My sister was gripping the dashboard before her like she was preparing for a crash by this point in her story. "Uh, what I was thinking. Mother opened the door. She had on the big bushy blue-green robe she sometimes wears that makes her look like some Hollywood black widow. She did not even knock but came straight into the room. She moved till she was right in front of me, her face not six inches from mine. She put a hand on my waist. Georgia, she said, go take a shower and throw on a robe and come to the bedroom. We should discuss this. I, I owe you an explanation."

At this point, my sister snorted. "Still waiting." She said. She turned to look at me. I know, we were sitting in traffic waiting for a wreck to clear. No one was moving. We could not escape my ill-informed question. "She, Mother, our mom, she... ah... she seduced me. She never made in attempt to explain anything. After I showered, I never thought I would have to fend her off so I dried off, put on my fuzzy robe and went into her bedroom. Yes, naked underneath it. She patted the bed for me to sit down. She got on her knees and faced me. She peeled the robe off my shoulders and then kissed my breasts, all without saying a word. I, I was in such shock I could not move. You know, except as she directed me. She took off my robe and then her own. She sat me against the headboard... I refused to lie down. It did no good. She, oh my god, she went down on me. Just like that. I came, hard."

Georgia was gripping the dashboard like she was on a roller coaster. Traffic pulsed slowly around us. She looked out the side window. "I had been on a date that night. This gorgeous man asked me for a drink, a supplier at work and I met him after work. He was sweet and wonderful but while he was off the toilet, I checked the Internet on my tablet and found he was married. I left. I could not face him. I had been primed since he asked me out; I was going, going to do whatever he wanted. I, I had not had sex with a man for so long... or a climax for that matter." She stuttered to a stop. "When, ah, when Mother touched me, I went completely still but I was so knotted up, when she went down on me, I, I came immediately. That just encouraged her."

Now Nova looked over at me, her face was flushed scarlet and blotchy. Her eyes were fierce. "I, I could not believe that a woman could get that out of me, much less my own mother. I was in such shock that I had nearly no self-control. Lots of stuff was going on at that time. Ethan had called me... and you know what that does to me. The shit really fucked up my head. Always did but all he wanted was another taste of Georgia with me as the main course. I hate those southern boys with their drawl and lazy eyes that make you think they are barely awake while they are slipping your panties down your thighs. They make it feel so normal, like a girl is doing the most perfect thing by lifting her ass and letting him denude you like that. Fuck!"

Now she was weeping but I think it was more complicated than Ethan the fuck who broke her fragile female heart. I reached over to pat her somewhere and could only find the full arch of her thigh. So I patted her thigh. She did not seem to notice.

"Mother, she seemed voracious but never asked anything of me. She ate me till I was desperate with orgasm, coming over and over again. After coming about the sixth time or so, I, I pushed her onto her back and she let me. She watched me while I got between her legs and ate her to orgasm, over and over again. Just like she did to me."

My eldest sister is so competitive and fierce. In retrospect, such a response seems, ah, odd perhaps but for Georgia, proving she could make Mom come just as much as Mom made her come seemed like a perfect extension of her fiery personality. Regardless, I had no inclination at the time to question her telling of the story and this part I could not verify. I had to take her word for it.

"I ate her till my jaw was aching. She sensed that and we exchanged places. She ate me again, pressing a thumb into me while I came and came. We were in a haze, a crazed mania that left us both panting and desperate for something more. I wanted cock. Mom wanted cock." Georgia hesitated and then glanced at me through a veil of her red hair which she did not bother to brush out of her eyes.

Contrasting
Contrasting
3,179 Followers