Extending the Milf List

The Skeptical Ex and the Office Affair

That was my weekend, snow removal and preparing for class on Monday. I had an early class and then free till the afternoon. Georgia called from Florida and said they were not coming back for a few days, maybe a week or more. The audit was more involved and since we were snowed in, her boss saw no point in returning.

"I don't mind. It's chilly, too cold to swim in the ocean but we are busy with the audit. Hey, is Tawny having sex with Chris?"

"Fucked him on the first date."

"Oh. Wow, really? I wonder if she'll share." She stopped and waited, I suppose wondering if I would press for details. I didn't. Georgia has the patience of a rubber band. "Did, uh, did Tawny talk to you, you know about, about...about you and your friends?"

"She said you and Dalia want what Mom and the other MILFs got. Is that right?"

Silence.

I waited.

"Well, sort of. I, I wanted it, I mean I want it but Dalia, she wasn't so sure, but then you haven't fucked her yet either. I think you should. She, I was too pushy and she is feeling slighted. When you get back, I mean when we get back, you need to take her on a nice date and do her in a toilet stall or something. She needs to relax."

"She doesn't want her own private orgy? Just you then?" I wondered how I would manage that.

"No. No, we negotiated and she'll, she'll do it. She, at first she just wanted to be there to watch when I did you and your friends. Hey, you will be there right? I mean...is it going to be weird giving us away to your friends when they have nothing to offer back?"

I found it curious that she was looking at this as a straight exchange and was giving thought to keeping things balanced. I was not sure if I was impressed or suspicious.

"I mean, you'll be there right? That, that is part of the buzz for me, you know, feeling your eyes on me while the other guys are doing me?" She chortled. "Can I help it if the idea of having my brother watch me fuck makes me crazy hot?

"I don't know. It's certainly unpredictable. If I can arrange it, I'll be there."

"Good, because Dalia won't do it without you and she, she says she'll do it only if I go first and if she gets to watch. I don't know how you set that up but if I know your perverted little friends you can sell tickets and take all their money if you like. I get a cut if you do. My idea!" Georgia laughed her low, threatening laugh like just before she soaks you with a water balloon or tries to nab your foreskin for her collection.

"I'll figure it out. Are you sure about this?"

"They won't blab, will they? I mean, about you and us?"

"I don't know. Is fucking their mothers bigger news than me doing my sisters?"

Georgia grunted and sort of laughed, a confused sound. "A point. I don't know about that. I'll leave it up to you. I, I want to be done by three guys at the same time. Oh god, now I'm wet, goddammit Sonny. I have to change." She hung up.

Sisters.

I went to school bright and early Monday morning without seeing or hearing zilch from Tawny. I really needed a car. I had the box of collars sitting on my table and I needed to distribute them. I was still puzzling over how to do that though.

After my eight bells class, I got a most delightful call, not D. Debra, either so back off.

"Ahmay, so nice to hear from you." I was shivering in the now zero weather, surrounded by the piles of sparkling snow. I shuffled into an empty class room and sat down. I saw a couple lift their heads from down further in the dark auditorium, well her head. "To what do I owe this surprise."

"I, well, Mr. Duncan, Sonny, I was wondering if you'd meet me for a cup of coffee?"

"Coffee? Sure. When?" I felt the tease but I was unclear about who was teasing who and who was being baited. Shit, Ahmay could catch me any time she wanted. If I were a fish I'd jump into her boat. If she came after me it'd be like chasing a parked car. I thought about D. Debra and found I no longer cared. I played a long game with D. Debra. I'd get her in a mutually wonderful way, but she was intelligent and that increased complexities, but also fun!

"Now. I mean, I am out and about. Where are you?" Ahmay found her voice again.

I told her and we arranged to meet close by at a little shop I knew had good coffee but where I could get breakfast.

I was nearly done eating when Ahmay appeared in the doorway scanning for me. I stood up and she came over and shuffled into the booth across from me.

I confess I expected her to fidget and act all shy but she was calm and cool. She looked at me after her coffee arrived, batting her long eye lashes at me. She waited and I waited but knowing I had a class coming up, I broke first.

"What's up, Miss Perfectly Wonderful? To what do I owe the honor of your presence?"

She seemed unfazed, flattery was surely commonplace in her world. She sipped at her coffee. "I have decided I want you to take my virginity." She said quietly. Her voice was strong and her eyes steady.

"Okay." I said, I am sure, much too quickly, eagerness dripping down my chin. "I thought we had established that."

"But I have requirements, some, some things I want. For you to arrange for me, for us."

"Us?" I was thinking of Rodney and decided to address that particular worry immediately, and again. One thing about brothers, you can't break up with them so, well, you have to resolve things, eventually once the train goes off the track. Otherwise its like fiberglass insulation in your underwear; it won't go away and its damn bothersome. "Have you discussed this with Rodney?"

Ahmay nodded. She sipped from the coffee again. "I, we have been talking about it since that day you and Mrs. Honeywell came to the store with that blond woman and we, you, Rodney...you know. Since then."

I nodded. "I remember it fondly. But didn't we discuss this just the other day? After, well, after I shared a new blond with him?" Ahmay looked away, scanning for something but not speaking. Something had shifted, because Ahmay seemed, well, uneasy now. That struck me as weird. I waited, curiosity waiting to pounce on the cat.

"I, you know, you understand that I have listened a lot, when Rodney had sex with his women. I, I haven't ever looked, I mean seeing you with Mrs. Honeywell that was the first time I ever saw such a thing. I mean I watched, often, while Rodney undressed them and they sucked his cock and then, once or twice when he went down on them but, but when he got between their legs or behind them on their knees, I turned away, closed my eyes and just listened."

I wanted to ask why but that was a stupid thought. I had finally gotten better at thinking before I blabbed every itinerant thought stumbling around my brain. I waited.

"I," now she looked down. She suddenly shrugged off the billowy winter coat and revealed the tight sweater that hugged her form as tight as an idea hugs the brain. God but she had the most incredible tits, even with bra armor and the thick sweater, looking at her tits was like watching someone peeking around a toothpick.

"Sonny?"

My eyes snapped up. "Oh, sorry. Your are so beautiful I got confused. I am supposed to be listening to you with my ears not undressing you with my eyes." I thought this was okay to say out loud. Perfectly true in any case but I needed reassurance that Rodney wasn't going to appear and unman me before he shuffled the rest of my anatomy around. "Rodney, he knows that you...he hasn't changed his mind or anything? I mean, like it or not, you two or sort of a package deal."

She nodded. "He says you are a good guy, even if you are busy fucking every old broad that has a rack. He likes you, I think. He is not really into liking other guys like that, not buddies or anything but he," she giggled a little. "I think he is a little jealous. When I told him what I wanted, he got upset."

Oh shit. "How upset? Wait, what do you want? Or do you mean, your er, virginity and stuff?"

"Listen Sonny, I, I, once I realized that sex was never going to be all romantic for me, that, that I needed something more, I got to thinking about what I needed or wanted."

I shivered involuntarily. "Sex is simple, like making a hotdog. You have a bun and the meat and I am volunteering to be the meat. Simple. Beyond that, also simple. You either want to or you don't. The other person either wants to or you don't. If there is any disagreement, you keep negotiating till everyone is on the same page."

She grinned impishly. "I always read the last chapter of a mystery first. That's sort of what I've done with sex. I, I bet I've listened to Rodney have sex with twenty different women. With younger women, not like, you know the first blond..."

"Laura."

Ahmay nodded. "Right. Mrs. Wills, wasn't it? The younger women, contemporaries, they, they seemed to feel better about having me in the room with them. Rodney, he is a tough, a bit of a thug when it comes down to it and having me there, I think I sort of kept him in check. You know, like a UN observer during an election among people who can't read. He, he can be cruel but, he knows I don't put up with that. Our mother, she ran off and married a rich guy," Ahmay bowed her head. "She was a white woman and she just up and left us. My father, he never recovered. They, they were not a good match. That's why my Aunt Elainah, Dad's sister, why she raised us. Still, Rodney is really protective of me and I think, I think I am like the mother he never really had and if I rejected him, he'd crumple. Luckily he knows that but it has made it difficult for me to, you know, date or anything.

"Anyone that seemed like the least bit of a threat, he scared them off so, by the time it was time for me to actually act like an adult woman, I had no practice at it. That, that is how I ended up watching him undress so many." She actually giggled then. "I, I have a confession. I, several times, I asked him to, you know, get with a certain woman because, because I, uh, I wanted to see her. You know, naked."

I nodded like that was the most usual thing in the world, despite the head of my cock bonking the underside of the table. "I never thought you were that vain." I whispered wistfully.

Ahmay's face scrunched up. "What do you mean? I, I am not vain!" She seemed actually angry.

"Oh? Why else do you want to see another woman naked? I know, that's easy! To compare your body with hers. I bet you have yet to see a woman with a better body than yours!"

She sat staring at me. I could see the wheels turning, evinced by the altering expressions playing across her face. Finally she smiled timidly, like she understood the implicit compliment and decided it wasn't a turd in a croissant. "Oh. Well, maybe but, no, I, well, that is what I wanted to talk to you about. You see, you remember when Rodney asked about Mrs. Honeywell?"

I nodded.

"Well, ah, he wasn't actually asking for himself."

I cocked my head like I was trying to get water out of my ears, back and forth till my neck hurt. I was stalling. I wanted Ahmay to be more explicit because if she didn't mean what I was thinking she meant, I'd be shaving my legs on a railroad track. She rewarded my patience.

"Well, uh, he, he was asking for me."

I nodded understandingly. "I can see why. She's is beautiful and nude, so much more so."

Ahmay shook her head violently.

I got worried that I heard the train coming and I had lather on both legs.

"No. You don't understand."

"Please, explain it to..."

"I will if you'll shut up and let me!" She snapped.

I felt abashed and shrank into myself. The clock ticked in my head, which in a digital world no longer makes any sense. I felt time passing and my next class drawing closer.

"Sonny, just listen. I, I said I had things I wanted and I am approaching this in the best way I know how. I finally realized why Aunt Elainah did not want me to spend so much time with Rodney and his friends. I have an outsized sexual vocabulary but little or no practical experience. The only way people get practical experience is by, well, experimenting and I don't want to do that. It's, for a girl like me, its dangerous, particularly with guys like Rodney hangs with. They are not gentlemen, not like you."

I did not wish to rush her but I was fucking lost. "Ahmay, I have no idea what you are trying to say." I almost mentioned class but her tits were right there and I had a terrible time thinking I'd go to class before they were out of reach, er, sight, gone, gone home, I mean.

She sighed. "I am embarrassed but then I think about you and your MILFs and, and all your experience and I feel almost normal."

"Ahmay," I started, a plea in my tone.

"Just wait!" She snapped again but softened immediately. "Sonny, I like you and I feel like I can ask this of you. Hush now, just wait. I, I don't want to have a romantic evening that ends up fumbling around with the guy trying to get what I want to give but with no, no, what should I call it?"

"Romance?"

"No. No poise. I mean, I don't want to be clumsy and I don't want him to be clumsy." She patted the air between us. "Just wait. Listen. I, I want you to have sex with Mrs. Honeywell, while I watch. I mean, if you can. If she would. I, I want to see you have sex with her, make love to her on a bed and everything, like, like she is really your lover. See, I don't really know how to behave with a man and, I want, I think she would know, that she has, she knows how to surrender herself to making love. I, I fear that I can't, that I will always want to watch and never settle down and feel what it is like to be sexual.

"I, that afternoon, with Mrs. Wills and, and Alissa, I, do you remember?"

I nodded. Oddly, with all the trouble I had remembering things for class, I seemed to have an encyclopedic memory of the sex I have had, with whom, how and when and where. Oh, I got details wrong but, well, that afternoon with Ahmay seemed perfectly clear.

She was speaking. "I, your cock was the first one I ever touched, and, and her, her breasts, I held her while you were inside her and then, I kissed her. I, I wake up from that moment, the feeling of her fine skin on my tongue and lips and I am hot, wet inside and aching to be filled or touched or both. I, Sonny, what if I like girls? I mean, don't get me wrong, I, I am attracted to you but what, what if the female does it for me? What if they make me, you know, what if they arouse me, make me crazy?"

"You improve your chances of not going home alone, I guess." I spoke sardonically.

"I want to watch you with Mrs. Honeywell. I want to watch her with another woman, a white woman. I want to see you with two women, so, so I know how to be, you know, like that. Rodney only does girls one at a time and so, I just never imagined something like what Mrs. Honeywell did with Mrs. Wills that day. I, I never imagined but, but I wake up from dreams and I find myself longing to feel it, what they did to each other."

"Dining out?" I asked.

Ahmay regarded me seriously, her lips moving as though repeating the words to herself, trying them out.

"Kidding. I'm teasing you."

She smiled weakly. "Oh." She shook her head. "Sonny, listen, what Rodney said, don't start with me unless you are going to finish, I, I asked him to make sure you understood but I don't think you do. I, I have given up on being innocent and ignorant. I just don't find that attractive. I, god, I cannot believe I am telling you this. I, I let an old guy, maybe forty pick me up. He was smitten, I mean he was drooling over me. I went to dinner with him and even went back to his room with him. I, I was so turned on because I thought, I thought he was experienced and could, you know, show me stuff.

"But he was clumsy and nervous and just when I thought he would unzip my dress, he panicked and said he was married and much as he wanted me, he just couldn't do it. He, he was horrified and asked me to leave. He wept before I got out the door."

She shook her head. "I don't want to do that again. I, I want to try everything. I mean it. Everything. I want to make love to you, to a woman, with you and a woman, with two women. I want to have two men and three men and five men," she grinned a bit guiltily. "You know three holes and two hands. How does that work? Is it even possible? See? I don't even know. Next year, I am going back to college and, I don't want to be new meat. I want to be the hunter but I can't do that if I have no idea what I like."

She nodded emphatically then. "That is what I want. I want to know what I like so, so I want to try everything. I want you to do it all to me, with me, for me." She stopped, finally lifting her eyes from the table top. "Is, is that too much to ask? I mean, to ask you to be sexual with me like that? To share, to share a MILF or two or five with me? I mean, what if I really, really like women? I, god, I want to fell a woman's mouth on my pussy, oh god. I can feel it but, I want to feel you inside me too and kissing me everywhere." She dribbled to a stop. Her eyes sought mine and the silence stretched.

I searched for words. My first instinct was to ask if she had discussed this with her brother but I got the distinct impression that was the wrong approach. I swallowed that first inclination and sought some other approach. "Well, Ahmay, cool. Let me suggest this. We'll, we'll try something and then see. I don't want to set out an agenda or nothing like that. Let's, I'll figure out a way to maybe address this issue with Alissa. I, I think I can persuade her, or maybe I'll just surprise her or something. Let me think about it.

"But Ahmay, you, you have to allow for a little romance. I, I don't think I can, I don't think I can do this with you unless I feel it with you. I mean, when I kiss a woman, I kiss her. It is real and I feel it. I'll feel it with you but I don't know what it will be like till I actually do, kiss you I mean. We'll, we'll just start and go as far as we can but, Ahmay, I need to know that if I make a mistake or you get upset, I need to know Rodney will not be gunning for me."

Ahmay seemed, suddenly at ease again. "I, we, my brother and I understand what decisions are mine to make and which ones aren't. Who I choose to let into my bed, or more to the point, whose bed I choose to crawl into and what I do there is all my business. He knows that and he may scare you but I assure you I scare him more. I have his number and he knows it." She smiled a rich, inviting smile.

I liked it enough I nearly forgot I was missing something. Luckily, Ahmay did not get confused.

"I, these things, these things I want you to do something for me, again. I mean. I, having real sex for the first time, I think I am ready and I think I want that but, but I want, I need these other things first."

"Uh huh. Is there a quid pro quo?"

She looked confused.

"I mean is this a negotiation."

Now she looked pissed. "I know what quid pro quo means, I was thinking about it. What you are asking is if I will go to bed with you regardless of whether or not you can do the things I want you to do for me, with me. That's what you mean, right?"

Now I had to take a deep breath and think. I had to close my eyes. Something about Ahmay made my heart hammer in my head. Oh yeah, her tits made me nutso crazy. Now that I felt sure I was not going to get crushed by her brother if I touched her...my brain ground to a halt. I knew exactly how to answer her.

"No, I meant that if things don't go as planned...and they never, well rarely, they rarel do...then I would not be looking over my shoulder for your brother waiting to jump me. That, I mean, I need to know that your protective brother won't kill me if something goes wrong and your end up disappointed or worse weeping and pissed at me."