Extending the MILF List Ch. 16

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Monday: How Much Sex Can One Man Have?
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Part 16 of the 26 part series

Updated 06/07/2023
Created 10/16/2014
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Monday: How Much Sex Can One Man Have? The Woman on a Leash

Author's Note: Thanks for reading. Hope you enjoy this, as always leave comments as needed and vote. I love to hear how the story is working and well conceived notes can be helpful. Thanks again! -C

You cannot believe the looks you get walking around with a woman wearing a silver collar holding her leash. We may live in an open minded society here in the US but it just isn't something you see everyday. It just isn't the usual way of being in society...yet. Not that it ever will be but until you have experienced the stares and the double takes and the muttering and envy and horror and anger and lust that it inspires, you cannot imagine what it is like.

I took Holly to class with me Monday morning. The poor woman was crazed, having seen Georgia get a little, well, a lot, the day before, she wanted hers. Her melt down put that a ways off and I was clear with her, that if she was going to be handed off to Gary Romelingame, she had to learn to heel and to fit neatly inside the envelope that enveloped Laura Wills so neatly.

My phone alarm woke me up at five. I felt drunk but I'd said I'd take Charm to her seven A.M. flight and I stuck to it. I got out of bed and padded towards my room. I was a little surprised to awake alone but was unperturbed by that. The light was on in my room and when I opened the door, I found Holly fixing her collar around her neck. I watched her click it into place. She turned and looked at me. She smiled brightly but when I did not respond, her expression dimmed, like the batteries were failing.

"Good morning?" She said, the question clear in her tone.

"You're up." I said, moving into the room and starting to dress. I moved around her and she stood still, not moving.

"I'm sorry, Sonny." She said finally.

"You don't have to be here if you don't want to be." I said. "I told you, you'd end up face down in a pussy if you came over yesterday."

She made a face, that expression that said, "Yes, but..." without any completion to the thought. Objection could exist without replacing it with a preference, it was that expression.

"I know. I just wanted cock. I felt left out and after spending all day being her plaything, I was uncomfortable. I was horny. I wanted..."

"You wanted." I repeated, sitting to put on shoes. The day was still far from arriving, still dark outside. "That's the problem. My job is to get you what you want and what you want is to be on a leash for Gary, right?"

She nodded, almost sheepish.

"The problem is what you want isn't important. Mrs. Wills doesn't think about what she wants, she spends all her attention and focus trying to predict what we want, what I want. With her, I demand that she do what I want as the first important way I give her what she needs. She focuses on my lust. I, in turn, can focus entirely on using her in ways that will give her things she will enjoy but may not know enough about to actually, consciously want."

"Like subliminal desires?"

I shrugged. "Maybe. Maybe she wants to be surprised by her own erotic satisfaction and she can't surprise herself, now can she. That might be my job, oh, and my delight. What I mean is this, to fit that collar, you need to quit worrying about what you want. I don't think about what I want from the women I own, I am too busy trying to figure out new and different ways to make them squirm."

"Squirm?"

"Yeah, squirm, as in being so horny she can't hold still. Like you were with cock yesterday. Did you think I had you over her just for shits and giggles? I wanted to test your tolerance for wanting and not getting."

She smiled wanly, almost apologetically.

"I didn't do very good, did I?"

"Very well and no, not so much. See, I think that desire is a sensation to be savored and appreciated all by itself. If you immediately satisfy it, you destroy desire and I want to teach you to savor desire and not pout when you don't get what you want. That allows you to enjoy desire without tumbling down into the pit of despair when your expectations go unmet. Desire, pure desire without any satisfaction or even any promise of satisfaction is unbelievably exciting. It energizes but only if you treat it as a thing itself, not as the first note of a whole song. That, I think that is Laura's gift or secret, she is totally willing to take what gets handed to her."

"I can't do that, I don't think." Holly mumbled. "I am too full of lust all the time. I imagine hands on me and then poof, off comes the hose and I am eye to eye with my own toes."

"Toes don't have eyes."

"Shut up."

"See? You can't say that and fit a collar. Shut up isn't part of what Laura can say, its what she can do. All of that noise, she coddles deep inside and when I can finally figure out some specific thing that floats her boat, or drowns the little man in her boat, then she comes like a house afire."

Holly tapped her chin. That hand held the chain looped to her collar and it wavered, catching the dull light in the room.

"Maybe I get that. All that desire, unrequited lust and unsatisfied passion is like a long, extended tease. She goes for days and days and it is all foreplay."

I squinted at her.

"Yeah, that's it. So when she does finally climax...."

"...it blows the top off her head." Holly finished for me. She nodded. "I think I get it."

"Then that's the end of it. Let's go."

"Sonny, wait."

I turned to look at her. She seemed smaller, though her boobs were still right there, demanding attention. I had a surge of sexual energy and felt that flush of satisfaction when you realize you aren't dead and still haven't exhausted your potential. Life wasn't downhill for me yet. Holly looked so forlorn, I pulled her into my arms and hugged her hard. I delighted in the plush pressure of her bra-covered breasts.

"We'll figure it out." I said.

"What if I can't? What if I'll never be able to keep my goddamn mouth shut?"

I chuckled, pushing her away.

"Who wants your mouth closed? I am pretty sure that isn't in the cards for you, my dear. Unless by closed, you mean empty. I think having your mouth full has a lot of potential."

She smiled bleakly at me.

"You know what I mean."

"Are you sure you don't need to go to work or something?" I ignored her concern, but did not dismiss it. I had a feeling this wasn't the last time I'd be presented with fitting a woman into a collar when it didn't fit her as it did Laura Wills. All that glitters is not gold.

Holly shook her head, the set of her jaw showed her stubbornness. It wasn't directed at me, it was a resolve to be different, to be other than how she was. I knew that and I had doubts about her ability to subsume that aspect of her personality to a man but she wanted to try and I figured it'd be interesting to let her. Besides, Morrison needed to trade something to me for Lydia, so whatever happened, I was getting something. I grunted. So was Chris. Once Lydia opened her doors, I figured she'd need a collar to keep her from attaching herself to any man that asked.

I trailed my hand down the chain draped over the blue swell of Holly's chest, being sure to press against them with the back of my hand. She sighed as I took the chain in hand.

"Its time to go. Let's see if Charm is up."

She was. The girls were downstairs in robes and slippers. They hugged her and we got into the car and headed for the airport. The sendoff was surprisingly subdued, almost like everyone was still asleep. I suppose there was that aftermath of an orgy, like waking up with your best friend's wife naked beside you and trying to gage just what attitude matched the situation, when none is the right answer, the die was already cast. Charm was subdued as my sisters. She didn't kiss them on the mouth or anything but just pecked each on the cheek and followed me out to car, well, she followed Holly actually but Holly followed me so, yes, I guess Charm followed me to the car. Really, she found her own way to the car. I was in no way leading her.

For twenty minutes we rode in silence. Holly sat in the back, her face pointed out of the car, I could see in her the rear view mirror.

"Sonny." Charm said.

"Charm." I responded.

She twisted to look back at Holly.

"I wanted to tell you something."

I glanced at her. The day was breaking gray and low over us. Traffic was light but thickening.

"I have had a man. A long time ago. I...what if I don't like girls as much as I think?"

I grinned. "Changing your spots, there Tiger?"

She grinned back. "Stripes, moron. No. But, god, watching Georgia yesterday, and the others...I miss fitting into something like that. Being a lesbian is complicated for me, though less so now than it used to be." She glanced at Holly again. "She's not listening is she?"

I shrugged.

"Listen, why chose? Maybe it isn't gender that you care about. Maybe it is just personality. Maybe all you care about is something that a male or a female can have." I glanced at her face and saw the expression of lonely bleakness skitter away. She nodded.

"Maybe." She reached over and took my hand. "You've been a champ, Sonny. Most guys would have had their hands on me but you treated me like...like...what is the word?"

"An equal?" I offered.

Charm squeezed my hand.

"That's it, maybe. I believe that you have a good heart, even though no woman should ever think they could put a halter on you."

"Don't have the tits for it." I muttered. "Glad of that, incidentally."

Charm smiled at me. She lifted my hand and kissed it.

"Sonny, if I ever decided I need a dick in my life, yours might fit me just fine. I don't want dick just now but you'd be good because, well, I don't think your ownership would constrain me any. You are pretty clear what you want from a woman and the rest, you just deflect it all. I admire that. I don't know how to do that."

I chuckled.

"It's raining pussy and I am just trying to catch as much as I can."

Charm twisted in her seat and smacked me on the shoulder with her free hand.

"Don't talk like that."

"Why not?"

She shrugged.

"I don't know, maybe I'm jealous. I don't know why that bothered me but it did, watching you guys, you people last night. I lay awake feeling awful and I don't know why. No, I do. I want to be in love. But what is that song that says the best is to love and be loved in return. My husband loved me but he wanted sex with men. I might have wanted something different with him..."

I squeezed her hand and took mine back. Traffic was picking up.

"No need to explain." I mumbled.

"Sonny, listen, yesterday affected me but it will take me a while to figure out how. Can I come back? Regardless of what I decide, I mean about dick and all?"

I grunted.

"I am flattered that you have any second thoughts about dick at all."

She laughed.

"After yesterday, being ringside with that sort of orgy, a stone would have second things, oh, I know, stones can't think."

We entered the airport. I got out and unlimbered her luggage. Holly got out. The two women stood staring at each other. Finally, Holly stepped up to the taller woman, cupped the back of her head and pulled her down into a chaste kiss on the lips.

"Good-bye, Charm." Holly said softly.

"Good-bye Holly. I hope you find what you are looking for."

"Me too. I mean, I hope you find it too." Holly returned.

We stood by the car and watched Charm stride into the airport. Even pulling her two suit cases she looked like a wisp of smoke curling in a gentle breeze.

I looked at Holly. She was still staring after Charm. I got into the car and Holly joined me in the front seat.

"She really is a beautiful woman." She said. She shook her head. "I really never thought I could kiss a woman like that or let her kiss me like that, all over I mean."

I didn't respond, concentrating on the frenetic oozing of the airport traffic. Once on the freeway, I looked over at Holly.

"Sure you want to do this?"

She nodded.

"Till I feel it or I take off the collar. I can't go on like I have. Gary isn't getting a divorce but he can't leave me alone and I don't want to leave him alone. I want to be what he wants me to be. Until that compulsion fades...I guess I'll just have to learn to live with it."

We drove to the college. I parked.

I don't think I got anything out of class. I felt like a spot light followed me everywhere I went. The collar around Holly's neck did not catch people's attention till after they noted the glittering silver chain in my hand. Then they just stared. Men and women. It was funny for a while, seeing a guy in a group catch sight of Holly, her blue coat open displaying her cleavage, the silver line running up to the collar. He'd look, then look again and then poke someone else and nod in our direction and pretty soon the whole pod of cockleberries would be staring at us trying to verify they were seeing what they were seeing as objective reality.

Women were different. They'd see us and then avert their eyes, only to have their gaze drift back to us as though some gravitational force projected from us and pulled at her till she had to stare. Holly kept the coat open, hanging from her broad shoulders exhibiting her tits and collar to anyone who looked. She sat beside me during the lecture. I tried to concentrate and take notes but the constant ripples of attention and the surreptitious use of cell phones to get pictures of us made me a little nervous eventually.

For a while I weathered the situation but then I met the instructor's eyes and realized that Mrs. Olivette was staring at me while she was talking, then I felt conspicuous and really nervous. I told myself the feeling running up the spine of my back was excitement and not doom. The feeling intensified when she closed the lecture with an announcement that her office hours were canceled for the day and appointments had to be rescheduled. Then she called out that "Mr. Duncan should stay after class for a moment." It was not a request.

I had intentionally sat in the middle of a row when we came in so Holly had to sidle past a number of other students. She presented her ass at first but finally turned and displayed cleavage as she went past. Several guys leaned forward so her tits rumbled against their nose or even cheeks on our way to the center seats. That meant that we sat more or less undisturbed as the other students vacated the place. It was slow going because many of them were taking pictures of us as they gathered themselves to leave.

Most tried to be casual about it but a very striking black woman stood and stared at us. Her hair flowed down like ink, glistening and bright. She was lean and tall. I did not know her. As the lecture hall emptied out, she moved to the end of the row in front of us and, when the last occupant was past, she walked down to stand in front of us. There was nothing friendly about her manner and I braced for some sort of feminist tongue lashing that was not part of any fantasy I had.

Instead, she stared at Holly, then looked at me. None of us spoke. Finally, she extended a hand with a folded piece of paper it in. I looked at Holly and she looked at me. The woman shook her hand once. Holly took the paper. She opened it, blushed and handed it to me. The note read as follows.

"My name is Meesa. I want to suck your cock. I want you to take me. I want you to fuck me. Please, tie me up and fuck me."

I stared at the note.

"Jesus, Miss, I can't just now. I'm, I'm occupied." I said.

She did not blink. She did not move.

I noted Mrs. Olivette observing us with an arched eyebrow. Finally I handed the note back to her. "Your digits and an email address. I'll be in contact."

She stared at her note then grabbed it and wrote furiously for a moment and extended it back to me.

"He will fuck you." Holly said softly. "Don't worry. You can't demand it though. Defeats the point of the collar. He demands, you deliver." Her smile was wicked and foreboding.

The black woman's face suddenly changed from the dark brooding wrath to a glint of understanding. She nodded, picked up her backpack and moved away, looking back over her angular shoulder several times.

"You could have fucked her. Now, I mean. That is what she wanted." Holly said, her voice replete with wonder. "I never would have believed it."

"I still don't."

"Mr. Duncan, if you please." Mrs. Olivette called, her voice rang in the empty room.

I looked around and yes, we were alone. I shook Holly's chain and made a clicking noise. "Get along, little doggie, let's go see what teacher wants."

Holly gave me a glare but immediately softened it. She followed me down the row and on down to where Mrs. Olivette waited. In the end, she giggled a little, which suggested she might be getting it.

"What is the meaning of this? You disrupted my class." She said archly.

I looked her right in the tits, breathing deep searching for something to say.

"I lost a bet." Holly offered, stepping into my robust silence. "I have to follow him around with a collar on my neck on a chain now."

Her voice sounded perfectly calm, reasonable even. I looked over at her. Holly had a very bland expression, appearing as though she were discussing weather.

"A bet? Really?"

Holly nodded.

We heard the murmuring of students arriving for the next class.

"Come along to my office, Mr. Duncan." Mrs. Olivette picked up her briefcase and turned to go but stopped to look back when Holly followed me. "Does she have to come with you? Really?"

Holly nodded.

"I have to follow him around like this or I have to blow all of his friends. I thought this was the best option."

I saw the shock on Mrs. Olivette's face immediately but then it was gone, vanishing as quickly as it appeared. She turned and marched to the staff entrance. We followed along behind her. Other professors passed by, only glimpsing the chain and collar as they passed us. I wanted to turn and see their reactions but didn't.

Mrs. Olivette stopped at her office door, fished keys from her purse and opened it. She turned on the light, stepped inside and set down her briefcase. I moved but felt Holly standing still. The chain jerked and she squeaked. I turned to find her staring at a tall, lanky professor who was staring at her.

I tugged on her chain and she moved into the office and I shut the door, just to hide her from the man.

"I bet his dick is the size of my little finger." I said.

"Don't care. You don't know that!" Holly groused.

I had read her pose properly. I shook the chain.

"Forgetting something?"

Mrs. Olivette cleared her throat.

"Mr. Duncan, why are you bringing this, this woman into my class room?"

I shrugged.

"You heard her, she lost a bet."

Holly chimed in.

"My boss, I bet him that I could beat Sonny at beer pong Saturday and he insisted I make it interesting. If I lost I had to suck Sonny's friends, if I won, I got a raise if I would suck him off. I lost. Sonny suggested the collar and chain thing and got me time off, with pay. So, you see, this is actually a lot better than things would have been if I'd been left to my own devices. I really shouldn't ever drink with my boss. He's always fucking me somehow and I never come. It's just bump, bump, bump and squirt. All I have to show for it is a mess in my drawers."

"You fuck your boss?"

"Jobs aren't that easy for a woman like me to find, lady. I bet you'd suck him off too if you had to deal with what I have to deal with all the time."

"What do you do?"

"I'm a parole officer."

I thought Holly had bitten it because I was sure Mrs. Olivette would ask to see her credentials but the professor just looked suitably abashed and shocked and turned her attention to me.

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