Extending the MILF List Ch. 11

So I got showered and wrapped an ill-fitting towel around my waist. No spare robe for the guest cock in the house, just a little shorty thing I would have worn but it was pink. I have my standards. So it was just a towel to saunter down the hall, like a lost Roman senator looking for the baths. My cock resisted being contained. I sauntered down to her door and stepped inside. D. Debra still sat on her bed. She saw me and stood up. She wore a robe and her hair was wet. She'd found another shower and undone the dirty as well.

"Close the door." She said regarding me through the wet tendrils of her hair, dark against the white of her perfect, glowing skin.

I closed the door. I felt a shiver go up my spine. I named it and then set it aside. I was playing the long game and could not get tangled up in labels. For now, I was doing as she instructed.

She stood up, pulling the pink robe around her, tight. Her breasts resisted the imposition and bulged invitingly, against the tight terry cloth robe. She walked to the dresser and shuffled through a drawer, straightening when she found what she wanted. She walked over to the bed and tossed something on the bed.

"Put them on." She said archly.

I approached, like I was sneaking up on a snake sunning in a strawberry patch. The things on the bed were fuzzy handcuffs. One was green and the other a harsh pink. It looked like someone had skinned and tanned a smurf. I put a hand in front of my eyes.

"God, Debbie, they clash. Why did you go disco when you bought hand cuffs?"

"I like disco." She said a little defensive. "When did you get all fashionista?"

"I'm not. But god, they clash."

"Put them on." She said. "On each wrist."

She did not seem happy. Fuck, I'd have thought choosing her would have meant something but I got a completely different vibe. She seemed disappointed and that seemed a little insulting. You're supposed to be disappointed after the guy comes on your tummy and goes to sleep before you come.

I stepped over to the bed and looked down on the handcuffs.

"Put them on." D. Debra Hamilton said, her voice lowering ominously, rather like that breeze just before a tornado drops out of the sky to TP the trees with your underwear.

I stared at the cuffs. "No." I said. The next few minutes were going to be tricky.

"What?" D. Debra asked. She tried to make her voice crack like a whip but it was limp with resignation. "Oh fine, I'll put them on for you."

I misunderstood. I thought this was going to be easy till she opened one of the cuffs and reached for my wrist. I jerked away. "No." I said.

"Why not?" She asked. She sounded tired but still, she seemed a little confused by my refusal.

"You put them on." I said. "I'm not the one that has been playing hard to get." I thought that sounded reasonable.

D. Debra stared at me, her eyes narrowed then. "You want me to put them on?" She said, as though the thought never crossed her mind.

I nodded. I felt like I was nodding too hard, like I was nodding with a head cold. It was tension. In for a penny, in for a pound our British cousins say. "I want you to put them on. I'll hook you to the bed, you know, so you don't get away this time."

She stared at me. "Oh, I don't think so."

"You lost the keys, didn't you?"

She smirked then showed me the release pin on the green cuffs. "See? Not really that difficult."

I smirked back and stepped around her and went to her dresser. The wood was blond like she was. I opened a drawer.

"What the fuck are you doing? Get out of there?"

"Got your little buzzy friend in here?" I asked moving to a second drawer.

"No. That's by the bed." She gasped a little. "Shit, Sonny, quit that."

I found what I wanted, a pair of long white knee socks with nice crisp elastic still in place. I moved over to her. I unfolded the socks and let them dangle in one hand. Time to make things right, once and for all."

"I choose you, Debbie." I said.

"Don't call me that. No one calls me that, no one ever has and no one ever will." The woman had a tell, I finally noticed. Her chin lifts when she's lying. All the times before when she was bending the truth to fit her purposes, that chin lifted a little. Wow, and I only noticed now!

"Debbie, listen to me. I have been willing to play along with you till now. That is over."

Something flickered in her eyes before they hardened. She stepped back. "What? What are you talking about."

"I promised you to my friends, or have you forgotten?"

"I, no, I haven't forgotten."

"What do you think? Are you going to renege on that?"

Her gaze flickered, like a light about to give up and burn out. "I, well, no, or I guess I hadn't really thought about it."

Something about her reaction suggested Mommy wasn't lying. Oh how things began to become clear to me. I love that feeling! "I made them a promise, the same one I made to you, that they'd all get a shot at D. Debra Hamilton. That's you."

"I know that's me."

"We agreed, hell, wasn't it your idea?" I forgot, to tell the truth. I waited.

"I, I guess I thought it was another way to tease you. If you hadn't gone along...." Her voice petered out like she ran out of breath. With lungs like hers, that seems improbable on the face of it.

"I have to confess something, Debbie..."

Her eyes flashed. "I said...!"

"I know what you said. You talk a lot but you don't always listen and you don't always hear. You might be a world smarter than me, I love a smart woman but it doesn't mean you understand everything you need to understand." I stopped speaking.

D. Debra Hamilton regarded me and did not speak.

I approved of her silence with a mere smile. I reached out for one of her hands. She let me pull at it and took a half step closer to me when the tension on her arm demanded it. I raised it and kissed the back of her hand. "I choose you, Debbie, but you need to understand something. I choose you. You don't choose me. You have to let me choose you but I want to tell you the whole truth and nothing but the truth. If I choose you, if, I say, if I choose you, you need to know what that means."

She blinked at me. "Get on with it. I'm going to need another shower in a minute, if you don't get to the point."

I nodded, allowing this demanding tone for the moment. I didn't really understand what she was saying. Did she mean she was sweating and would stink up the place or did she mean...oh. Oh! I was so sure of myself at that moment I was clueless. Wow. Had I known, I might have whiffed, like a football receiver dropping a perfect pass when he's wide open. I felt it, that certainty that everything was about to fit into a nice, neat logical package that would get Sonny fucked and well fucked all at once. It infused me with a surge of adrenaline because suddenly I knew I had her figured out just so.

"You need to have sex with each of my friends." I waited. Her eyes never left me. I think she sensed something, feeling the reality of what was about to be laid before her before it became real to her conscious mind and it robbed her of her will to speak, pulling away her breath. Or maybe it was just Christmas like anticipation.

"Debbie, I promised. You need to know something about these guys, about us; my friends, they are a close group and one of the things they tend to do is share things. If you fuck them one at a time, you'll be my sex object, a thing, Debbie." I paused. "Do you understand what I am telling you? You'll end up fucking them all together. I mean, they will want you at the same time." I smiled a little. "I am not kidding. They will take you at the same time, a cock in every hole. We call it the Airtight Express."

"Oh." D. Debra said, the syllable emerging as a wispy vowel.

"Yes. Oh. Are you ready to do that? I mean, you've been in bed with one man and your mother, how would you like to be used by five, six guys counting me and maybe a stray woman or two, all at the same time?"

"Oh." She said and this time it wasn't a full statement of understanding. It was an exclamation.

I played like I didn't understand that. "Yes. Oh. Say oh and ah and uh and when you are done with the little cheer leader chant, you'll find your body is completely full of cock. I am not kidding. You do this and I'll see you fucked in every hole. I promised and my friends, they're my friends and I keep my promises to them. Are you my friend, Debbie."

"Please, don't call me that. My mother only calls me that when I have been naughty."

"Debbie, you have used up my good will. I am pretty sure, what you have done to me can be categorized as being naughty." I made a show of staring at her body. I tossed the cuff in my hand onto the bed. I took firm hold of the sash on her robe and pulled her against me. She leaned away, eyes twitching back and forth.

"Debbie, when I make promises to my friends, I keep them. Are you my friend, Dorthy Debra Hamilton?"

She nodded, swallowing hard.

"I promise you, Debbie, you will be fucked by all my friends. If, if that isn't in your bucket, I mean on your bucket list, then, well, I don't think your mother has gone to bed and locked the door."

The mention of her mother seemed to snap her out of the haze. D. Debra shook her head. "Choose me, don't choose me, she'll still try to have you."

I noticed she didn't answer my question. "She said just the opposite. Choose her, don't choose her, she won't open up for business for Sonny any more. She said she can't do that to you."

D. Debra smiled one of those smiles we smile when we think no one is watching. "She wants you to resist, to put you out of reach so then she'll feel like she is robbing from me when she has you."

I untied the sash on her robe. She clasped it closed with her hands. "Wait. Sonny, wait. I, I realize you have chosen me but Sonny, I need something from you."

Here it comes, I thought.

"Two things, actually."

Oh fuck. "In exchange for what?"

She smiled a really warm, inviting smile that made me really nervous. "For me and my mother. We'll do you, we will. It, it might take some time to get us situated but we will. I will, I promise, as your friend and I keep my promises too."

Fuck me, Mr. Happy just about pulled something snapping back to attention. Porn with too much dialog sucks unless it is interesting. It just got interesting.

"So? What's on your mind." I pulled the sash apart and let it dangle from the loops. I moved my hands up to her wrists and pulled her arms aways from her robe. She stared at me as if in a trance. I opened the robe, exposing her breasts. I cupped them with each hand, feeling their downy weight in my palms and the hard scrape of her nipples on my skin.

"Oh god, Sonny, don't do that. I'll tip over." She giggled a little then and I think the sound disturbed her fog. "Listen, Sonny, you have to promise me something. If, if I do you friends, you have to own me. I mean, I have to be yours. You give me to them and I'll do them, like you agreed, because you agreed. I will, because I respect a man who keeps his word. I'll do them but you have to make it clear that you own me. When it is over, after they are done, D. Debra Hamilton closes up shop, folds her tents and returns to your harem. Deal?"

Harem? Shit, who has she been talking to? Surely that was unintentional, not related to my previous discussions with the MILF list. I had to know. "Harem? Just what are you suggesting?"

"I am no fool. I know you have other women. I know you want to share them with me, or is it me with them? Okay, fine, I lied when I said Mom lied. She told you just what has been going on. I did seduce every man she looked at twice there for a while and then we ended up taking turn with a few of them and they sort of got the full mother-daughter fantasy." Now D. Debra blushed and deep red like the wattle on a chicken.

D. Debra moved her hands up to grasp my wrists. I could not tell if she was trying to hold them in place, move them just so or push me away. I am not sure she knew. "I have gone down on my own mother, I admit it and yes, I liked it very much. She, she has skills. So do I, ask your sister."

"I intend to, now that I can't play like that never happened any longer." Yes, I was being a little disingenuous. Did me absolutely no good.

"That's the second thing, but first, are you okay with that? Owning me like that I mean? You have to keep them from ever asking that of me again. I demand that you be jealous and parsimonious with my body, doling it out only when it pleases you and restricting me to you and your cock the rest of the time. I don't want be fending them off and risk being the bitch to your friends."

Now who's being disingenuous? I grunted. That was easy to agree to but she'd not be strapped up in a chastity belt either. That much I knew.

"I have to be your girl, and I mean that in the most restrictive, possessive sense."

I nodded. "I got it. What's the other thing."

She looked like the cat that ate the canary. "Well, Sonny, before you get Mother and I at the same time, I want to see you with your sister." Now her hand tightened on my wrists, holding my hand firmly in place against her tits. "Before you say anything, you need to understand, you are asking me to have sex with my own mother. You have to balance things out by having sex with your sister."

I nearly jumped the shark right there. "Which one?" I asked. Now it may not seem like a perfectly dangerous question but think about it for a moment. If having sex with my sister wasn't somewhere on the radar, the first thing out of my mouth should have been "no fucking way" and then I'd have paddled her for even suggesting it. I didn't. The realization that I didn't jumped up and smacked me after the words left my lips and suddenly I was terrified. I don't know why. What could she do? I knew she'd had sex with her mother so, as far as outing us goes, we really did have the secret oath in our own little incestuous society already.

D. Debra did not notice. I could tell by her next words.

"If you want us, together, at the same time, you'll do this. For me, to make me feel, comfortable."

"You mean safe?"

She released my wrists. I responded by peeling the robe off her shoulders, shucking her naked like a oyster of its shell. She let it drop, puddling around her feet. My god, she was built to fuck. She did not hesitate. She got to her knees and unwrapped my cock. She wrapped one hot hand around it and bent it down. She looked it in the eye and then kissed the little crown. She sucked at the end and it seemed to slide into her mouth and completely out of sight with nary a huff or a puff from her. Down past the fluttering tongue, the broad pad cupping the shaft as it slid into her mouth. She sucked hard and I was embedded in her throat. She groaned around it.

"And you said I'd never feel this. God, I am feeling it now." I wish I'd just fucking shut up sometimes.

She pulled off my cock and looked up at me.

"Sonny, is it worth it? I mean, you have to see, let me see you have sex with your sister."

"Tawny, you mean?"

D. Debra grinned. "Yes but she might prove a reluctant client." She sucked my cock into her mouth again, seeming to have lost focus. She hummed as she sucked and then pulled back again. I really wanted her to finish the chorus.

"Sonny, listen, I know this is a lot to ask but look at this from my point of view. I, I am offering my mother to you, and to allow you to give me to your friends. Is it too much to ask you to let me watch you have sex with your sister?"

I should have said "yes" and smacked her, only it wasn't. In retrospect, maybe I should have been suspicious. Nothing ever came of it but what if she was testing me? At the time, I was just eager to let her know any price for her and her mother in the same bed with the same objective, that is with me as their objective was worth paying a lot for. I almost accused her of something but then decided to take another approach.

"Why should I do this for you? You need me. I can feel it. If I say no, I can still have you. That's what I think."

D. Debra kissed the end of my cock again and if I hadn't tried to drown him in her mother earlier in the day I am sure I'd have been hosing down the blush in her cheeks from the inside out. I had to find out why she used the word. "You said 'harem' before. I like that idea but that means you fuck when I say, where I say, how I say and if it comes to it, who I say. Right? I own you ass, mouth and pussy, right?"

"So long as you can make me climax, yes."

"So long as I make you climax." I agreed.

"Then yes, anytime, any place, any how you wish and if you want to hand me off as a party favor, I'll do that maybe, I will, I will but only if you promise always to be there and to take me away before they tire of me. You know that old saw about being a stand up comedian? Leave them laughing? With a woman owned and loaned, it is leave them hard. They should go home and fuck their own mothers after I am done. Right?"

Quite a choice of words. She sucked my cock down again.

A great shudder ran through my body. She felt it, her hands moved around and she clutched the cheeks of my ass and pulled me against her face. My cock disappeared into the tight confines of her imagination. The naked woman hummed as she sucked on my cock. Surely I looked like Einstein with his finger in a light socket.

D. Debra pulled off of my cock and struggled to her feet. Her wagging tits kept messing with her balance. And mine, for that matter.

She picked up first the lime green disco hand cuff and put it on and then the hot disco red one and put it on her wrist. Poor smurfs.

I took them off again. I was beginning to think ahead. I just had one problem and I was going to work that out right now. D. Debra watched, puzzled while I picked up the white knee socks I'd purloined from her dresser drawer and pulled one over each hand, covering her arms to the elbows. I could feel the curiosity bubbling in her, like she wanted to ask if this was some odd fetish and I liked fucking things with four legs but she kept silent.

I recovered each pair of cuffs and the light went on when she felt them snap into place over the socks on her wrist. No, the socks weren't to make her more comfortable, it was to make it more difficult if not impossible for her to escape the cuffs by herself. I leaned in and finally kissed her for the first time that night. She kissed me back. Her nude body melded with mine. We mashed my slick cock between us. I could tell she was brittlely aware of it but don't ask me how I knew, I just did.

The kiss seemed to go on forever. I kissed her passionately till she blew through her nose and wriggled free, panting.

"God, Sonny, you kiss with everything in the tool box. God, no wonder your tongue inside of me does what it does!"

I guided her onto the bed. I pulled each arm to the side of the king sized bed and fastened the cuff to the brass pole of the headboard. When I finished, she sat, arms spread, her tits surging up from the pose. I arranged pillows behind her and she finally relaxed back and regarded me.

"Do we have a deal?"

I didn't want to let on that she had negotiated hard to give me just what I wanted and already had. I steadied myself on the bed, standing on my knees with her thighs between my legs. I looked her right in the eyes. "If you want to see me have sex with my sister, I'll say this. I'll try. I will. I won't say now but someone has to go first and that is you."

She hesitated then nodded. "Okay. You, me and Mom but you are going to have to negotiate that with Mom too. We Hamilton's we don't give shit away for free."

I didn't think that'd be a problem.

"You fuck me, you fuck mom, you fuck us together, then you do your sister and then do her with me." Now D. Debra blushed again. "I mean, I think it will be easier to do her with me there, you know? Not quite so weird."