Extending the MILF List Ch. 06

Story Info
What's long and hard and sensitive? Not Medical school.
41.9k words
4.72
50.4k
47

Part 6 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
3,178 Followers

The Sister, the Schizo, the Aunt and the Savant

Morning arrived for me as a ghost. The dour days were gone and the year dawned with bright sunlight that hurt my eyes. I closed my eyes, feeling the moment. My stomach growled. Happy fucking New Year. That sounds more surly than I mean it.

I felt pretty good. I confess I had a niggling reservation about my conviction that being passive with D. Debra Hamilton would result in getting my wick wet. I was playing a waiting game and if last night was any indication, I was behind on the scoreboard.

My general count, however, was pretty good. Oh, counting is déclassé. Numbers count. I was getting plenty of high quality pussy. I guess that was why I could be patient with D. Debra Hamilton. I certainly was not letting her behavior bother me. It was a game, she was winning but it was a long way from over. I play the long game, its good to be long.

I woke and lay thinking these things. I rolled out of bed and trickled downstairs. I had a banana. I padded around, looking for Tawney or my other two sisters. I found the house completely empty but for me. I remembered finally that Dalia and Georgia had left early. I was muzzy. I felt light-headed. Something about last night energized me, my body I mean. My mind reeled from seeing D. Debra Hamilton eating my sister.

It felt wrong but I was still in that vast no-man's land where anything D. Debra Hamilton did seemed fine to me. I mean, I knew better but I wanted it to be fine, wanted her to do all the things that made me happy or made me feel wonderful and I still thought that if I did the same thing for her, she would return the favor. When you find someone like that, keep her but know that most people, male and female do not behave that way.

This was the lesson D. Debra Hamilton was teaching me and the one I was learning. I did not know that at the time though it has become perfectly clear since. I was evolving and D. Debra was helping me. You rarely understand life's lessons till after the fact; you get the test and the understanding follows...if you survive. I still thought that we were fated to be together, despite my deviation from the normal romance, with Mrs. Bickerstaff, Ellen Collier, and my two sisters.

Okay, there is nothing normal about that sort of romance. That is my super power, maybe, forgetfulness, like a good pitcher or quarterback or goalie. I could bring all my energy to the woman within arm's length regardless of what was going on in the rest of my life.

I heard my phone ringing. It was upstairs on my dresser. I bounded up to get it and caught it ringing. D. Debra was calling. Speak of the devil and the devil appears...or think, or dream. It all works.

"I fucked your friend. Chris? Was that his name? Where did you go? He finished quick and I went downstairs to find you, his cum running down my leg..." she giggled. "I wanted you to see my racing stripes." She giggled again. She seemed perfectly at ease. "Where did you go?"

"Home." I said, feeling slightly guilty at the half truth, but then I was never going to tell D. Debra I was doing my sisters...was I? The thought made my teeth hurt.

"Why? I wanted to dance with you, the first in the new year." She hissed a little. "No matter. Listen, Sonny, I think I have an idea. It would be fun. I realized last night that there is something missing in our relationship."

She stopped and I waited, once more brainwashed of any thoughts of my own. All my mind contained was the image of her naked, broad ass, her hour-glass back, and my sister's legs dangling off the bed on each side of her. After a prolonged silence I managed, "Oh?"

"Dick. Sonny, I miss Richard. I miss riding a cock while I am coming. I miss the feeling of a man's cum squishing around inside me and then bubbling out when I walk, oozing out and running into my hose and making it cold. I miss that fresh fucked feeling."

My heart flip-flopped. This was the moment I had counted on, that I had waited for. My chest felt like it was going to burst I was so proud of myself. I knew it! I knew she would come around and want to ride the Roger with me.

"I think I should fuck all of your friends."

Her words stabbed me in the ear and ran all the way through my head. My chest did burst and then collapsed. I couldn't breathe. The disappointment nearly overwhelmed me. I was a putz but worse, I knew I was a putz and the worst of it all, I was only a putz around D. Debra. She had ensorcelled me, I was bewitched, enchanted, hexed, caught in a pussy web I could not escape.

I give myself credit. I was suddenly calm, deflated, embarrassed at being so ebullient and then immediately so wrong so quickly. I gave myself a pass. My thought in that moment was this: What can I expect when I am in love?

D. Debra was speaking. My ears put a hold on it till my mind was ready to process what she was saying and then let me catch up.

"Thursday, four o'clock. Thurston's. You know Thruston's? Very high class, so you probably don't. I only go in there when I need the perfect dress for a special occasion. I have a fantasy about fucking a guy I don't know in there, in the dressing room. They are really very nice places. I go there and just sit sometimes. I smoked a jay in there one time, just to be...well, that doesn't matter. Meet me at four o'clock on Thursday. Bring one of your friends and I will fuck him. Not Chris. He doesn't count as strange dick any more." She stopped talking and just like that my phone gleeped.

I looked at it. It was Landon. Fuck me. What timing? Like the fucker was volunteering to fuck my...the thought stuck in my brain. I had fucked his girl, hadn't I? Almost behind his back? Was it karma that my girl wanted to fuck him? My mind seized on the phrase "my girl". If I was not fucking her and she was fucking my friends, is she still "my girl"? My next thought was that I was not exactly keeping the trouser monster in the zipper pen so what was I to her? There was the question. What he to Hecate or Hecate to him?

My phone gave up or Landon did.

"Sonny? Sonny? Are you there?"

Deedee's voice sounded a little worried, plaintive. I liked that. It suggested she was testing me and was at least a tiny bit unsure of herself, of her suggestion.

"Four o'clock. Did you get that? Thursday. See you then."

"I got it but..." She was gone. I took my phone away from my ear and stared at it. I wanted to object but could not think of a way to do so without letting her slip free the bonds and leave me. I didn't want that but I no longer felt trapped by her spell.

Suddenly, I liked the idea of handing her over to my friends. If she wanted to fuck but didn't want to fuck me, it made a sort of twisted sense to provide her the dick she was denying herself, even if it wasn't mine. I'd have some investment in the exchange. I felt twisted, then, utterly alien to my own sense of my own identity. What a strange world I lived in. I resolved to give her to my friends as a fair exchange but for what? I puzzled over that for a while before I realized I was standing in the living room staring at nothing.

I went up and washed Georgia off me. By the time I was dried off and had changed the sheets on my bed, the rack monster ambushed me and I crawled between clean sheets and fell into the dark crevasse, or maybe I was pushed. The last few days caught up with me.

I woke but my eyes remained closed. My cock was hard. I lay on my back. The thrill of an erection fluttered into wistfulness, wishing I could remember the dream that so inspired such healthy wood I must have been good! I have to admit I was beginning to think my cock was superhuman, plumbing the depths of human endurance as I was. Something had awakened me but I kept my eyes closed, thinking I had neglected to call Landon back. The thought fled me in the next moments.

I felt a breeze and then a fingers lifted my lolling cock, straightening it. Lips kissed the head. A wet, live tongue wrapped around the helmet, swabbing my clean cock. The lips clasped the end and she kissed it, sucking gently on the bullet end before sucking it deep into furnace of her mouth.

I shuddered with the pleasure. I knew it was female because I felt breasts on my knees.

I opened my eyes. The head bobbed under the sheet. The dark green sheet left no hint of who was sucking my cock. I admit I cannot tell one blow job from the other, though I have not had much opportunity to do a robust comparison. I take them when they are offered and with thanks, appreciation and sincere delight. The gift horse and her mouth and all.

Her head emerged from under the sheet. Tawny lifted the sheet, crawled over me and knelt athwart me while she felt between her legs for my cock. With me carefully in hand, she connected it to her pussy and slowly sank down onto me. She sighed softly. Once mounted, she began to rock, shifting her hips back and forth.

Her head was turned to the side, the sweep of her auburn hair half-covered her face, one eye fluttered as she ground her body down onto me. She jerked back to front when my hands found her hips. I began to help, arching under her, ramming up as she ground down.

"Good morning." My sister whispered.

"What are you doing here?" I asked.

"I live here," she groaned and bent forward, placing her hands on my chest, her hips rocking with greater urgency. For a while she fucked me, her moaning reticent, wordless, eyes fluttering with the pleasure our connection sparked in her and passed to me through the conduit of my cock. Up my spine, to my sizzling brain, captivated by her feeling, the heedless need. She wore a long sleeved white sweater with a green skirt, plaid, like she had mugged a Scotsman and taken his kilt. Knee socks covered her lower legs where they clasped me along the side of my hips. The inner flesh of her thighs burned me as she rode me.

"What are you doing here?" I asked again, panting now, because I was arching my back to thrust up into her.

Her eyes flickered open and she gazed down on me. The sweetness usually lolling there was replaced by a rapacious pleasure. "Fucking my brother." She whispered. "Oh god, Sonny, you feel so good inside me like this."

She leaned over me lowering her face in a smooth descent like cold honey pouring out of a Mason jar. Her lips touched mine and her body became still. She kissed me like it was a virgin's first taste, the flashing sensations of her enveloping body roared through me, her legs clinched me between them, holding me while she kissed me. Her mouth opened and her breath blew over my face. Her breasts brushed me with the white sweater, tickling me with a new, rougher sensation. I pulled the sweater out of the waist of her skirt and snaked my hands underneath then up her sides to find her breasts. She sighed as I clasped them over the bra. She sat up, looking down her body at the knobby shape of my hands on her tits.

She gigged half-heartedly, like she was embarrassed. "Fucking my bother! God, how did we end up like this?" She closed her eyes and dropped her head back, exposing her neck to me like a lioness conceding herself to the the king of the jungle. Her pussy clinched down on my cock and I twitched up under her. My sister groaned and then returned to her ride, rocking her hips to create the fire in her body, lighting her fire with my erect match.

She stopped again.

I almost protested but then she began to squeeze my cock with her pussy, clamping down and relaxing. Her face took on a look of concentration.

"Oh Christ!" I finally groaned as her pussy rippled lasciviously up and down my cock.

Her eyes opened and she grinned down at me. "Feels good?"

"God, yes. Don't stop this time."

She stopped. Fucking bitch. What do you expect from an older sister; they just don't like even the slightest hint of being bossed around.

"I talked to Mom this morning. She, uh, she says happy New Year." Suddenly she began to hammer herself onto my cock, sprinting into a full drive towards an orgasm that appeared out of nothing. After a dozen hammering pumps of my cock into her, she tensed, she squealed, she jerked, she clinched her eyes closed and stopped breathing, just for a heartbeat. Then her body bucked and she wilted.

My cock did not wilt. When I arched under her, she gasped and lay down on me, kissing the side of my face and neck, nibbling at my ears and panting, her hot breath scorching my skin.

I moved my hands to her ass, clasping her tightly as the orgasm rippled through her body.

"Oh god, again? I, I must have come two dozen times since you left last night." Tawny struggled to her elbows, her face close to my face. "Your girl Debra does like eating pussy overflowing with cum. She sucked Chris hard and fucked him and then sent him to me, at least a couple times. Then she ate me and ate me and ate me. God, oh God, Sonny, I think I might like having my pussy eaten, at least by her. I came and came and came. It was so luscious, having his cock in me and then her mouth, God, I am drunk with just the memory of it." She lifted her head from beside mine and kissed me again, hard on the mouth. Her lips were alive, pulsing against mine while her hot breath burned me.

Her monologue resumed. "I think Deedee fucked up your buddy. He, he was terribly upset about fucking her, particularly after I told him you haven't fucked her yet. He, he thinks you'll be furious with him."

I snorted. "I fucked his mom and both of his aunts and he is worried about one teasing blond?"

Tawny smacked me on the shoulder. My hard cock thrust deep in her reacted and she squeaked. "Don't put it that way. He, it is sweet that he is upset. Hey, wait, you fucked his aunts? You didn't mention that!" She glared at me and I glared right back. She was sitting on my cock, how upset could I get? "He is trying to figure out how to tell me that he is boning his mother. God, I got so turned on thinking about him and his mom." Tawny left the sentence dangling.

I thought she was going to ask and almost prompted her to do so, eager to arrange that for her. Her mind had skittered in another but similar direction.

"I spoke to Georgia, I mean, Dalia really." She lifted up, to sit down firmly onto my cock again, wiggling her ass to touch as many nooks of her cranny as possible. "That is why I am here. They, uh, uh, uh, they called from the airport. Their flight was delayed. They, she, they, she..."

"Which is it?" I asked but Tawny had found some part of her pussy that reacted to cock and seemed determined to grind that little bit of lovely real estate onto the end of my cock till she came again.

"They, they said I could fuck you while they were gone if, if if...oh god!"

She came without me again. Her hips rolled over me, like a boat on high seas, riding the waves, cresting and crashing down, impaling herself hard onto my cock before grinding us together. Over and over again, her face twisted and her shoulders hunched while her body jerked and bucked. This was no way to have a conversation but she had permission to fuck me and she seemed determined to make the best of it.

She orgasmed again. And again. And again. Riding me while using me like a dildo, grunting as the pleasure fountained in her, a parody of my little, frustrated fountain consumed by the maw of her body, insatiable and silken. Finally she halted all motion. I thrust up once but her hands turned to claws on my chest.

"Don't, oh god, don't. I think I'll lose my mind if I come again." She twisted and moved off of me.

I felt distinctly neglected.

"I, I thought, I thought I could do it like that but, but, god I am crazy with lust. The more sex I get, the more I want it. If Dalia hadn't called, I'd be fucking Chris, trying to figure out some way to get him to get his mother to join us! After Debra introduced me to, to, to that, I seem to be fixated on Mrs. Wills and her sweet mouth." Tawny grunted out a guttural laugh. "Her sweet mouth? See what you have done to me?"

"Me?" I asked, feeling distinctly under appreciated and unjustly used.

She had rolled onto her back beside me, twisting the covers around her and off of me. The house was cold and I wanted a little cover back again. My cock glistened with her coating in the chill but refused to retreat. I got to my knees beside my sister's legs. She looked up at me through half-close eyes, knees splitting wide to accommodate me. I moved between her open legs once more. Her arms stretched over her head as I entered her again.

"Oh god, Sonny, fuck me."

I sank into her bubbling pussy. "Tell me what you have to say." I said, halting my descent into mindless pleasure at half way, half descended but enveloped by full pleasure.

Tawny arched under me, taking the rest of my cock into her body. With her hands over her head, she held the pose for only a few moments before plopping back to the bed. "Nova, she wants what Mom got. She, she wanted me to ask you, to, you know, arrange for your friends to do her." Tawny turned her head to the side as I pumped up and down between her legs. She lay still, accepting my cock into her body, letting me search for my own little climax.

I felt there was more to be said. Not by me, by my sister, so I waited, that is, I didn't say anything. My cock continued to rub a dub dub in her tri-fabulous tub.

After a few deep, slow strokes, Tawny looked back up at me, turning her head to fix her eyes on me. "Dalia, Dalia said, she said she wanted it too. All of them, at once, one after the other like Mom did." My sister hunched her hips up under me, enveloping my down-stroke with her liquid pussy. "Oh god, Sonny, fuck me hard." Her voice seemed to drift about us, soft and demanding at once.

I hammered her hard, finally grasping her ass and ramming my cock into her with short, trenchant strokes. I was panting and groaning when finally my orgasm overflowed, flooding down into my beautiful sister. A wave of intense emotion rifled through me and I think into her. I think she felt it too because when I lifted up to kiss her, she lifted her head to seal her lips to mine and we kissed intensely while I filled her with my cum, hunching between her legs while her body seethed around me.

When the jagged climax had run its course, I collapsed onto her. She held me off her chest with her hands, pushing up at my shoulders so she could breath. I lay as dead on her, between her splayed legs.

"Sonny, Sonny? Heavy." She grunted.

I got my elbows under me, releasing her tight little ass. I rocked to the side and she lifted that knee up beside me. My cock slipped out of her well-oiled pussy.

"I want it too. We, we all do. That, that was what Dalia called to ask, if, if I thought it would be okay. You know, to fuck your friends."

"I am sure they would be happy to fuck you." I grunted. My mind was not working because it was only later that the complications of this concept suggested themselves. I was merely thinking of Tawny's pussy while a cock was working its way into her ass. She'd go fucking ape shit.

"You, you don't mind? I mean, you don't think its a bad idea?"

"Of course its terrible idea but so is fucking me. I'd say you were quite a ways out of bounds already. Fucking my friends will hardly make matters worse." I moved over her boundary leg and lay beside her, now hopelessly tangled in the sheets. Tawny lay beside me still fully dressed except for the absence of panties, but thoroughly and delightfully mussed.

"That's what Mom said. More or less."

I tried to sit up but could not, I could only speak my shock. "You told Mom you fucked me?"

"Well, not exactly. I told her Nova wanted to fuck your friends. All she said was she thought she'd have fun. Georgia, I mean. Mom said, she said she'd probably enjoy being airtight. That was how she said it, Georgia would enjoy being airtight. Then she asked what I thought about it. I'd asked her first but I told her anyway. I said I wanted it if Nova got it. I wanted it too. Mom just laughed and then she had to go."

Contrasting
Contrasting
3,178 Followers