Sharing the MILF List Ch. 12

When we were finally alone walking down a corridor on the sixtieth floor, he said. "I need your help, Sonny. Listen, Darlene is going to be down in the bar at twelve. She wants a threesome with, with two guys. She said she'd get me someone to share her with. She is a little nuts I think but she told me she would be working tonight. She said I could have her for a grand but she needed to do another guy first. She has expenses, she says. Fuck me."

"Threesome?" I said blankly. Then my mind switched on and the mosquito got a lot bigger, pterodactyl-sized I think. "Threesome?"

Landon opened the door with a key card. We went inside and he pointed to my shirt. "Nice shirt." He slipped the card folder into my pocket. Then he pulled out a wad of twenties. Go down and have a scotch in the bar, when you see her, get her attention and have her come over. Wait for her to make her move and then when she is set, bring her up here. Don't worry about the money. She'll want a grand and will be clear about it. She knows you so she does not have to be careful," Landon stopped. "Right, Sonny?"

"Right what, Landon? That I am not the fuzz? Right. What is this?" I was still thinking "threesome"; I kept seeing the word in huge blinking pink and red neon in my mind's eye. It was damned distracting

"You are going to fuck my girl." Landon said.

"Jesus Christ, Landon. Your mother and now your girl. I'll be in hock to you up to my ears forever."

Landon patted my shoulder. "Not so, not so. I'll owe you. My alternative was to have her fuck some other guy. I'd rather share her with you. We have some experience with having a woman pinned between us. I'd rather it be you than some smelly booze hound with a lot of cash. Get going. She said I had till midnight when she quits being Cinderella and turns into a whore, her words."

"Threesome?" I said again, reading now. I am sure my eyes had that thousand mile stare. I was suddenly seeing Darlene Emerson with her hands over her head and Landon sucking at her big, beautiful, stout breasts. My cock told me to get some. "Threesome?" I said again.

Landon finally slowed down, realizing I was in shock. "She said, she said she needed more bread. She had to fuck someone and when I offered to do her twice at twice the price, she got a little pissed. Told me she was in no way going to use her boyfriend as her sugar daddy. She said to find her a john or she would. What am I a fucking pimp?"

"Threesome." I said again. It seemed so stupid. We, Landon and I and the guys had orgied our mothers but this was different. Darlene was just eighteen. Somehow, it seemed all different from doing MILFs. Even Annie and Melissa Crawford seemed out of her league somehow. I don't mean that how it sounds, it's just, fuck, the feel of a young woman and her body is different than a MILF. "She wants." My mouth was still not bothering to do everything my brain was telling it.

"The money. But she'll let us do her at the same time for the same price." He glanced at his watch. "You have to go. She is pretty good at getting a guy's attention, I think. I expect once she walks into the bar, there will be line so you have to be there first."

I was pretty sure I heard a twinge of pride in his voice which made the whole moment seem that much more surreal and believe me, I know surreal. Turns out I was still a rookie. I held up my hands. "You want us to double-team your girlfriend?" I said.

Landon finally looked right at me. His face worked then and then he nodded. "Okay. Yes. I want you to fuck my girl. Ass or pussy. You pick."

"Ass. No, pussy." I said automatically. Having to choose warped me a little. I was far from the only one. Landon looked fucking nuts. I grabbed him by the shoulders and shook him. "Landon, buddy, snap out of it! Do you get what you are asking?"

His eyes quit twitching all over the fucking place and met my gaze. After a half a minute, he nodded. "You were right. I have not really got it that she is a whore. Prostitute. Prostitute she calls herself. Or hooker." He shook his head. "Fuck me, Sonny, I'll do anything for her. She wants two guys, fine. You're the one. You have to go now. Go. Now!"

Landon was clearly rattled. I left him in the room, watching me as I trotted back to the elevator from the door like I was his first grade son off to my first day of school. He even waved when I looked back. I had just ordered a twenty dollar scotch and paid for it with one of Landon's bills when Darlene appeared at the entrance to the bar. I had been thinking about how money had never been an issue between us; he had lots and I shared with three sisters which meant I was fucking broke most of the time. Seeing Darlene at the door of the bar looking like a million bucks unnerved me. More. If that was possible. The scotch seemed more like therapy than recreation.

She scanned the room and I nodded at her. The look on her face told me Landon had not revealed his particular solution. She drifted over to me. Men stared at her with hunger and naked lust. Her breasts were clearly visible through the diaphanous dress she wore, moving as she moved, inviting everyone of us to stare at her, beautiful and braless. We did plus some women with a mélange of expressions on their faces as they sipped from their straws and tried not to be caught staring at the bold woman with the great, obvious and very, very proud breasts.

The outfit she wore was simple but sexy, and familiar. Her top was a revealing something that looked like snake skin.

Darlene sat down and held up a finger and told the bartender she wanted a Tequila Sunrise. When she brought it, Darlene clinked my glass and smiled. Another twenty.

"Hello, Sonny." She said, a slight lisp in her voice.

I did not recall the lisp. Her dress V-ed nearly to her belly button but black mesh ghosted her pearly skin the glistening, blue-green snake skin did not cover. Her breasts filled the faux-snakeskin making it seem metallic and commercial, which, I guess she was. When she twisted to reach for the pretzels, I choked. Her back was bare to the small of it with only a small band of the shimmering snakeskin across her broad shoulders. I almost reached out and touched it, her back I mean. Her flesh was luminescent and the aura around her, twinned with the erotic aroma of some perfume that lured me into her spell. I could see the twin arches of her ass clearly uncovered by the back of the dress with the dark crevasse that led to cornhole heaven or her pussy place. I shook my head. Something about the milieu was making me crude. I think I was having an allergic reaction to fucking my best friend's girl. It might have been the thousand bucks she was going to ask me for. My mind touched that but I think recoiled and repressed it because it went right out of my head. Might have been the gorgeous young woman sitting before me.

I shook my head, again, trying to get the vision of the arches of her ass bound up in the dress out of my mind.

"What's the matter? Lost your nerve?" Darlene smiled.

"Darlene, I . . ." I did not have enough breath to stutter. This was Landon's love! The metallic green dress shimmered. I wanted to touch it. It was tight, sealing itself to her body, accenting the contours of her fully developed, succulent flesh. Cupping her breasts like I wanted to in the worst way. One thing I could not argue with, Landon had every reason to want to please this woman. Her sensuality seemed natural and unhurried but easy and carefree with just the right amount of lightheartedness to make it seem logical that she would share that eroticism with you. She was utterly enticing. "Darlene . . . " I stuttered again without any idea what I wanted to say or should be saying in this situation. My mind was freelancing, thinking this woman could make a fucking fortune which made a chortle rise up in my chest which I had to stifle.

Darlene laughed. "Shit, Sonny, you have no idea what it is like to hear my actual name in this business." She sipped and looked me as she did so, bending her head forward rather than lifting the glass so her eyes regarded me out of her long, sexy lashes and past her pencil eyebrows.

I gulped and drained my scotch.

Darlene watched me throw it back and she smiled slightly and followed suit, downing the remainder of her Tequila Sunrise. "I guess we are going." She said.

The flush of the scotch warped though me, singing that low song that makes you thrum with anticipation of something. In this instance, it was sitting right beside me. The fumes of the scotch and Darlene's sensuality wafted into my nostrils and I suddenly felt very, very willing to fuck her. Threesome? I thought. When she stood up, though, a chill ran down my back and I think my cock length went negative. I put a hand on her forearm and guided her back to her place. I signaled the bartender with two fingers.

She came over, "Double scotch and a, a Tequila Sunrise?"

"Make mine a single and yes. Dead on."

The woman, a stocky no-nonsense figure that relied on character rather than cleavage to please her patrons, grinned. "Take care of this one. She looks dangerous."

I nodded. Suddenly I felt both the urge to touch Darlene, a hand on the knee or a caress of her side or even bumping the back of my hand against her breasts. I felt terribly guilty.

Darlene was watching me and did not seem to hear the bartender's comment or ignored it. Her brown hair was cut and layered and puffed up so that it cluttered her shoulders and fell invitingly about them, clear to her breasts. In that moment I felt like I had seen her before, a ripple of déjà vu that shocked me. I sat muted and stunned trying to figure out where I had seen this woman before. Of course, that was a stupid thought because Darlene and I had a class together in high school before I graduated. Of course I had seen her before! What a stupid sensation!

But then it struck me; that great "Ah ha!" moment that is so luscious when it does not stand your hair on end. Darlene looked enough like Kyla Clark she could have been the woman's daughter. Seen together with Kyla and Landon, Darlene would look like his sister! My cock got suddenly very hard as visions of my three lovely sisters cavorted through my head. I shook it again but only succeeded in a vision of Darlene and Kyla as mother and daughter. I could not tell if I needed more scotch or less.

The bartender sat down our glasses. I dug out a twenty and dropped it on the bar. Then another when the woman arched a bushy eyebrow at me.

"Change?" The female barkeep asked, dryly.

I shook my head, afraid my voice would squeak if I tried to talk. My lizard brain committed a twist of the first order. A vision of the two women nude, Kyla Clark and Darlene Emerson kissing, taking cock and moaning out their pleasure as Landon and I fucked them while they kissed each other. This visions shimmered behind my glazing eyes. My cock sprang to attention and my whole body shivered.

New plan, I thought. Then I realized what I was thinking and I gulped my scotch down again. How could I get Kyla and Darlene to fuck us? "She's a hooker." I thought. "A couple grand and you can ram it to her." I think I needed less scotch but that was a matter of metabolism. I sipped more in that curious sort of logic that alcohol teaches.

Darlene did not follow suit this time but took the straw in her drink and pulled the red liquid slowly up the clear straw to her pale pink but lusciously full lips. "Are you okay, Sonny?" She said after swallowing ostentatiously.

I nodded. It was time to speak and I feared for my dignity if I tried to do anything complicated. "So, Ms. Emerson, how did you get into this business?" The words left my mouth before my hazed brain had time to stop it. I thought I would be wearing her Tequila Sunrise but Darlene took another drink and pushed it away.

"Landon is waiting." She said.

I nodded. "Fuck him." I muttered, not meaning it but I was reluctant to show this ravishing woman that I was scared spitless. Then I grinned, "Making him wait for you, I am thinking that might be a little bit fun."

Darlene smiled at me. When her hand touched my leg, I felt it in the roots of my teeth. There was fucking something about her, something about her manner that made her seem accessible, mysterious and desirable all twisted up in a single package of T&A. I could see why she could demand a thousand bucks at a swing. Fucking her must seem like a trip into orbit for a common man, or even a master-of-the-universe Euro-trash like Hans von whoever.

"Thanks, Sonny, for doing this, I mean. When I told Landon I needed the money tonight, he offered to pay me two grand for a go but I would not do that. We working girls have ethics and standards you know. He insisted that you would help me out, be happy to. I was not sure he meant it but here you are. He said you were the best friend a guy could have and you would join us so, well, so he did not have to call me Candy Swanson all night."

I wanted to fixate on the idea that she acted surprised when she saw me and Landon did not think she knew I would be here. People get the strangest ideas, conclusions drawn from the same fucking conversation . . . I gave up on that line of thought. I concentrated on the here and now.

"Why would he call you Candy . . . oh, yeah. You mean if you found another, I get it." I tried to seem worldly but this all rattled me to my core. I know, seems stupid for a guy with a nearly completed MILF List but everything is not the same and when you encounter the difference between an experienced MILF who by the way happens to be your mommy and a girl who apparently sold her ass for a grand; it tends to make an impression. My best buddy was in love with this woman and I wanted to fuck her. What a scene! He wanted me to. It was his idea! Big difference from sexual admiration managed in private.

Darlene smiled and for the first time, I noticed she had dimples. The smile gave her a look of innocence but her eyes held a steadiness that made the innocence seem . . . different. "You are so cute, Sonny. I'm glad it's you."

"So, a Candy . . . " It was harder than I thought to switch gears.

Darlene laid a hand on my arm. She turned on the stool and crossed her legs right in front of me, exposing them before her and to my eyes. What legs! My god I almost swallowed my tongue. God but I love women! She leaned an elbow on the bar. "Darlene, Sonny. Let's not make this too professional. We do know each other and you did me a solid the other night. I was, a, worried about that conversation with him, with Landon. He seemed so blasé about it, I was worried that he, well, whatever. You put my mind at ease." She pulled more Tequila Sunrise up the straw into her pursed pink lips. "First, I would never have thought I would fall for Landon Clark. Or, best of all possible worlds that he would fall for me." She looked at the face of her phone laying on the bar. "It is a quarter after midnight, shouldn't we be going.

I nodded, then shook my head violently. "Not ready. I am sorry, Darlene, I am having a tough time getting my brain around this. My best buddy calls me and tells me to come fuck his girl? You know that does not happen every day in the male world, right?"

Darlene laughed and turned to sit beside me, her legs under the bar, the shiny silver five-inchers hooked on the rung. Yes, I looked. Her legs shimmered with hose or whatever. Her tight skirt seized her body and presented it for inspection. I just had to glance to see so I did. Then my imagination interfered. The vision of her in garters nearly unhinged me. Getting the picture? I was definitely feeling out of control.

"Sonny, Landon said you were the best buddy a guy could have. Now I see why." She turned to face me again, leaning on an elbow. "Landon is a selfish prick and wants me all to myself but I have to turn a couple tricks tonight and doubling my price on my boyfriend just does not seem right. It is a stretch to charge him for, ah, it. But a girl does what she has to." She grinned. "He insisted."

I almost laughed but saw my opening to extend the conversation. My cock was rock solid focused on the situation but the rest of me was far from sure that I should give my cock his due and fuck this woman. "Wait right there, Darlene. That is what I just do not fucking get. You are actually Darlene Emerson, right? Or am I confused?"

Darlene nodded, her eyes suddenly serious. "Yes, Sonny."

The way she said that made my mouth go dry. I love it when I hear my name taken in vain like that! I know I have said it before but fuck me I love it! I shook myself, mentally. I had to focus and surprisingly, I could. "And your father is Constantine Emerson, right?"

Darlene nodded.

"And he is one of the richest men . . . "

She was shaking her head.

"You don't understand." She breathed.

" . . . in the city and so it does not make sense to me that you are, a, hooking." I looked around. No one paid us any mind but the bartender who's eyes twitched over to me as I looked around.

Darlene nodded. "My father lost everything. In the crash, he bought lots of securities that turned out to be filled to overflowing with bad paper. He invested everything he had, we had, convinced that the market would remain strong even after Lehman when down. We are broke. We have been living off his reputation since then. We owe everybody. I would not have discovered it if I had not turned 18 and tried to access my trust. Somehow, the trust my mother's father left me worth five million, Daddy had penetrated it and it was empty. There was only $2,127.19 in it by the time I got to it. Hardly enough to pay for Stanford. I went to mother and it was like I was trying to tell her that daddy fucked my ass. She would have none of it. She insisted that we were fine and Daddy would figure it all out. I just had to be patient, something I am not long on. Patience, I mean. When I confronted Daddy, he said I did not understand, that he had borrowed from the trust and it would be there before I needed it.

"He told me to go ahead and apply. So I did. They asked if I needed financial aid and I said yes and asked Daddy for his tax returns for the last three years. He refused. I broke into his office and found them and the shit had dummied up his tax returns to show he was still making 100 million a year or some such bullshit. He paid taxes on money he had not made and did not have! Can you fucking imagine!"

"Shhhhh, Darlene." Her voice had risen and I saw the barkeep glancing at us. "Best not to attract attention, don't you think, since both of us are underage?"

Darlene smirked, all sign of the coquettish vamp was gone. "You think they care how old you are if you can afford to pay twenty bucks for a scotch? Those rules are for other people. In here, if you have the scratch, you have the right to the catch. The only time they get uppity is if you don't pay or something." She looked around.

I said, "Maybe we better go. Landon will be . . . "

Her phone rang. She gave me that sort of look you never want to get and answered. "Hi Sweetie! Yes, he's here. No. We're having a drink or two. No. He says if he is going to fuck his best friend's girl he wants to get to know her first. I think that is perfectly sweet, don't you. We'll be up when Sonny is ready. What's the matter, afraid he will bug out on you and make you find someone else to fuck me?" She made a kid's face at me, screwing up that sexy mug to look like a ten year old's, which deflated my cock. "No, sweetie. Don't worry. As Sonny has pointed out, it is not every day a guy is asked to fuck his best friend's girlfriend by his best friend." She tittered. "I like how that sounds—girlfriend! I am your girlfriend, right? I thought so, so fix yourself a drink and we'll be there when we get there, okay!" She hung up and looked back to me. "You were right! That was kinda fun. Where were we?"