Cuckquean Experience

"Hi, Master," her voice purred into my ear. I loved her voice. She always sounded sexy and submissive and wonderfully needy.

"Hello, slut," I said. She giggled on the other end as I made my way to the back door.

"Do you really live in San Diego, Master?"

"Yes, baby," I told her. "Would you like to meet?"

There was silence and then, "More than anything in the world, Master. But... is your wife okay with it? I don't want to..."

"I know, slut. Let me ask you though, does it matter?"

More silence, "No, Master. It doesn't. I'll do whatever you say regardless, I promise. I'm a good girl, Master."

"I know you are. But you're also a dumb little slut, aren't you?"

Her heavy breathing was audible over the phone, "Yes, Master. You made me that way."

"So you're going to be wearing EXACTLY what I tell you, aren't you?"

"Yes, Master."

"And you're going to edge every night and not cum until we meet."

"Master!?" she said in shock, "That's so long. I'll be a dripping puddle of a mess, Master."

"So? Do I care?"

"No, Master. You're right. That was selfish... will you punish me for that selfishness, Master?"

"Of course, bitch. You're going to be so desperate when we meet that I'll be able to do anything I want to you and you won't even consider objecting will you?"

"That's exactly what I want, Master. Make me your pathetic little bimbo bitch. Train me. Use me. Degrade me. Anything."

"Good girl. Now I'm going to go to bed and fuck my wife and tell her about this little conversation. You're going to go to bed after edging for an hour."

"An hour?"

"Yes, slut. Or should I make it two?"

"No, Master. Have fun with your wife," she said with sadness.

"I will slut. And just think, I'll be raping your holes in a couple weeks for real," I told her.

She gasped, "Yes, Master. Thank you, Master. I need that, Master."

I went to the bedroom and Helen was already waiting for me. I'd been talking right outside the bedroom window and she'd heard the whole conversation. Her legs were spread and she was holding her cunt open wide. I shucked out of my clothes and wordlessly climbed on top of her. I looked into her eyes, "Are you sure this is what you want?"

"Your cock in me or your cock in your slut, Master?" she asked. Her eyes flicked back and forth as she studied my face.

"If I slide my cock into you right now, I'll be sliding it into her in two weeks. Is that what you want, my love?"

She nodded, "More than anything, Master. Now please fuck me. Fuck me like you're going to fuck her."

"No," I said as I slammed my cock into her. "You get my cock in your cunt. I'll fill you up and make you cum. She gets my cock in her ass to remind her that she's just a cock socket for me."

"Oh fuck... Yes... John... fuck," she said, whispering in my ear and trying to stay quiet as I hammered into her.

"Cum for me, slut," I said. "Cum for me and prove to me you're an obedient little cuckquean."

She did just then. She came around me, squirting juices out and over both of us as I continued to hammer her. It didn't take me long either, I was so turned on that her vice like grip around my shaft had me emptying myself into her waiting pussy only minutes later.

"Are you really going to do it, John... Master."

"Are you really sure you want me to?"

"Would it matter if I did?"

I looked at her, "Absolutely. Tell me not to and I won't. It'll end it tonight. She'll never hear from me again."

Helen sobbed, "I love you, John. That's what I needed to hear. But I want you to fuck her. I promise. I do. I want you to."

"Good," I said with a smile. "You can reassure her of that yourself," I said.

"What do you mean?"

Helen and Lily had never actually talked. I'd been the go between. The common thread between them. I figured Lily had to be a little bit worried that what I'd told her about Helen's wants and condition might not be true. She was too smart not to be curious. I held my phone up and flicked the contact to call Lily with a video call. The screen flared to life and showed a picture of Lily's ceiling and a desperate, raspy voice said, "Hello, Master... did you have... ugh... fun with your... wife."

I gestured to Helen who nervously whispered, "Th... this is Helen."

"Oh no... Mrs. Watts," Lily said. I could tell her voice had dropped out of "slut mode" and into her normal speaking voice. "I'm... I don't."

Helen and I laughed, both at Lily's confusion and her calling Helen "Mrs. Watts".

"Lily... it's fine. John just... uhmm... well... he fucked me good and hard. The... the same way that... uhmm... I want him to fuck you."

"Really?" Lily said, allowing her voice to slip back into the sexy tone I was used to.

"Truly... slut," she said and smiled at me.

Lily moaned on the other end, "I am..."

"A slut?" Helen asked.

"Yessss."

"A whore?"

"Oh yesss."

"A dumb little cunt ready to get her holes used by a man she's never met?"

"UGhh... oh God... oh God... You almost made me cum... fuck..."

"Good girl... two weeks and you'll get what you need," Helen said.

"Thank you... Mistress," Lily added.

"Now go back to edging, slut," I said. "And remember, no cumming until my cock is inside your tight little ass."

"My... my ass... Master?"

I laughed, "Enjoy your misery, bitch."

"Thank you, Master." The line went dead and Helen and I smiled at each other.

The two weeks absolutely flew by. I talked to Lily every night. Tormented her with stories of what I was going to do to her. How I was going to use her. Her friend was picking her up at the airport. They'd apparently insisted. I paid for the change fee of an earlier flight so we could have a couple hours together. It wasn't as much as I wanted. I wanted to bring her home and use her for a week while Helen watched and cheered us on. Helen had even proposed me tying her in a chair and fucking Lily while Helen struggled with the ropes. But alas, there wasn't enough time. Nevertheless, the fateful day arrived. I was at the airport, dressed in a suit. Lily had a real thing for older men in suits and I wanted her as turned on as possible. Though given the two weeks of edging, she was bound to be a walking, drippy cunt regardless of what I wore.

When I first saw her walking down the hallway, I was blown away. I'd seen her on my phone and in the pictures she'd sent but she was far cuter in person. She was short and thickly built, curvy and sexy. So different from my tall, athletically built wife. My cock was instantly hard as I imagined what I wanted to do to her. She saw me and flashed a sexy, crooked smile. She was wearing a thin, white summer dress and high heels. The collar around her neck was completely incongruous to the rest of the outfit. The word "Master's" written across it even more so. She walked up to me, blushing from her cute head to her little toes. I stepped in close to her and whispered, "Are we Master and kitten or John and Lily?"

As if to answer me, she pointed to her collar and then unbuttoned a single button of her dress. She let the cloth flap open revealing the words, "Master's rape meat," written across the swell of her breast. I grabbed her hand and drug her behind me. We waited for her bag, me holding onto her ass and squeezing it possessively while we stood there. Five minutes later we were walking quickly out to the parking garage. I'd parked at the top level in the far corner. I'd found a large van to park next to and backed into the spot. We had nearly complete privacy. Lily had yet to speak to me.

"Are you ready for this, slut?"

"Yes, Master," she nodded as I held the door open to our mini-van. I'd folded the seats in the back down and laid out a blanket.

"You know I'm going to use you, right?"

"Yes, Master. That's all I've been able to think about for two weeks. You using me completely. Don't even pretend like you care about me, Master. I... I don't even want to cum, Master. Just rape me and break me and use me so I can finally be useful to your cock, Master."

"God you're a hot little bitch," I said as I unzipped my pants.

"Thank you, Master. You say the sweetest things," she purred. Her smile ended abruptly as I gripped her hair hard and shoved her down onto my cock. She sputtered and choked as I plunged her over and over onto my shaft.

"Get it good and wet, whore."

"Yarth, Marther," she murmured as I bobbed her up and down forcefully. Once she'd slobbered my cock completely wet, I yanked her off and flung her across the vehicle.

"On your knees, slut," I told her harshly. She obediently did it, without hesitation. I flipped her skirt up and ran my fingers across her ass, "This is going to hurt, bitch." I traced my fingers over the words I'd made her write on her ass. "Use me", "Hurt me", "Owned bimbo", "Cock Sleeve". I knew she'd followed instructions. There were other words written all over her body. Hiding underneath that thin, white dress she wore that projected such innocence.

"Please, Master. Don't stop for anything. Don't stop until I've pleased you fully, Master." I smacked her ass and she moaned out, "Yessss... God I've wanted your hand doing that for so long."

Again and again I smacked her ass. When it was nice and pink, I pulled my belt off and started using it instead. She never protested. During our playtime, she'd always seemed reluctant and desperate to avoid the pain. But she'd also always told me that she desperately wanted me to do it because it would be so easy to take it if I was there. If I was the one whipping her ass and tits and not holding back. Turns out she was true to her word. I worked her ass over for several minutes until it was turning a dark red.

I grabbed a bag of clothes pins and put them around her nipples and eventually on the nipple itself. She moaned in satisfaction at the pinching, "They're sooooo tight, Master. Thank you for hurting me." I placed some more on her cunt lips and stroked my finger across her clit threateningly.

"Maybe someday, slut," I said to her with menace and she shuttered. Each set of clothes pins was connected by a string. It would allow me to yank them away whenever I chose. I knew she had a similar setup at home. Many times I'd had her place them on herself while she edged and then made her yank them off to ruin an orgasm. She was most submissive when I was being extra cruel.

Once she was all ready, I moved up behind her and placed my cock against her ass. I'd lubed it up while she wasn't looking but as far as she knew, all that was on it was her spit. I didn't say anything, just leaned into her until I felt the head pop into her tight little hole.

It was amazing. Her ass was tight and hot and gripped me as if its existence depended on it. I pushed further in and she moaned a loud, satisfying sound of joy. "Thank you, Master.. You're taking my anal virginity. I'm yours now, Master."

"Where is my cock, slut?"

"My ass, Master. YOUR ass, Master."

I was now fully buried inside of her and I slowly pulled out as I asked, "You're getting ass fucked before you've even been regularly fucked."

"Yes, Master. That's what I deserve."

"You're getting ass fucked by a stranger in the back of his van and you've never even kissed him."

She gasped as the realization of just how utterly slutty and depraved the situation was hit her. "Yes, Master. I'm just a useless little cock sleeve. Your useless little cock sleeve."

I grabbed a handful of her dark brown hair and yanked it back hard. "No slut. Not useless. Just a pathetic little bitch that needs more training," I snarled. She moaned as I rammed my cock hard into her again. I then started giving it to her harder and harder as I continued the stream of degrading insults that she got off on. Finally, I felt my balls starting to boil over. I slapped her ass and growled out, "Cum for me bitch. Cum right fucking now you trashy little anal whore." I yanked one of the strings of clothes pins off her right breast and she screamed in ecstatic agony.

Her hand flew to her clit as the second set of strings was ripped away. She screamed and started cumming not even five seconds later. She was rewarded by the clothes pins on her cunt to be pulled away. Her orgasmic scream went up another octave. Her ass clenched me hard and I shot off as well, screaming obscenities into the rocking van as we both came harder than we'd ever thought possible.

I collapsed beside my new lover as she quivered and spasmed through her own orgasm, "ThankyouMaster. ThankyouMaster. ThankyouMaster," she babbled. I was still sitting there trying to catch my breath.

"Was it everything you wanted, baby?"

"Yes, Master," Lily managed through staggered breaths.

"I wasn't talking to you," I said. She looked at me confused and I gestured to the small picture of my wife on my phone. Helen's face was inches from the camera and I knew she was on her hands and knees teasing herself while she watched.

"Yes, Master," my wife said lustily.

"Master... you made your wife watch as you claimed me and defiled me?"

I nodded, "And now she's going to watch as I kiss you for the first time."

Lily practically swooned as I brought my lips to hers. She tasted sweet and slightly slick from whatever lip balm she'd used. "You got what you wanted, Helen. I've claimed my first conquest."

"Thank you for this, Master," my wife said.

"Now, I think we should have some alone time while you imagine what I'm doing to this little slut puppy. I'll give you a rundown tonight."

"Have fun, Master," my wife said cheerily as the screen went black.

Lily nuzzled against me and whispered, "Your wife is very lucky, Master."

I laughed, "I'm the lucky one." I kissed her again, enjoying the sweet intimacy of the action after the depraved fucking we'd just engaged in. "Oh... I've got a present for you."

"A present, Master?"

I pulled out a little box and opened it. Inside was a large, fat butt plug with a jeweled top. "You're going to keep my cum inside you until after your friend picks you up. Understand?"

She shuddered and nodded then slid the plug into her ass as she stared me in the eyes. "But, Master. Now your favorite hole is filled... whatever will you do?"

"Oh you silly slut. I'm going to abuse you until you break and then blast my cum all over your big tits. And you'll wear that cum for the day too."

"Yes, Master," she said with downcast eyes and a huge grin. "I hope everyone won't realize what a slut I am."

I laughed again as I reached my fingers through her hair and gripped tight, "My hope is the exact opposite."

Her eyes sparkled as she said, "Mine too."

The rest of our time together progressed pretty much as I'd hoped. By the time I'd finished, she'd coaxed two more loads out of me. The two I'd already promised and a third she'd finally managed to get in her cunt. It was leaking down her legs as I walked her back into the airport. She looked like she'd been getting rough fucked for two hours in the back of a van which, of course, she had been. "Go get your makeup fixed before your friends show up. Don't clean up the rest though, slut. Understand?"

"Of course, Master. I'm going to enjoy the feeling of your cum all over me. I feel so absolutely owned right now, Master."

"You are," I whispered to her before giving her another kiss.

True to my word, I told Helen all about it when I got home. The story provided three days of crazy sex in which we relived and reenacted all of it. Even the anal sex that my wife hadn't really liked in the past. Now she couldn't get enough. Eventually, life returned to normal. Lily and I went back to sexting online every night, longing for the next time we could hook up. A few months later, Helen turned to me in bed. It was another bad night and she was, again, in pain. There was no chance that sexy thoughts were going to get her past the pain tonight.

"Do you like, Lily?"

"Of course," I said. I'm not the kind of person who can be intimate with someone I dislike so the question confused me.

"No... I mean... how much do you like her?"

"I... I like her a lot... but, you know... as a friend."

"Uhhuh... John. Be honest. I promise I don't mind. There's enough love in your heart for two women."

"I don't love her, Helen," I said annoyed both at the question and at how close to home it felt like it was hitting.

"Okay, Master. But just know that it's okay if you develop feelings for your side pieces."

I tried to put the conversation out of my mind but, like that very first one, I couldn't quite move past it. I'd set these rules for myself and I was breaking them. Even if Helen didn't see that as a betrayal, I did.

A few months later, Helen got accepted into a new clinical trial. The results were rapid and amazing. The new medication was a three weeks on, one week off regimen and the results were better than our wildest dreams. Suddenly she was having three pain free weeks followed by a week of manageable pain. For two months in a row, she had only one day where she was stuck in bed. The change was night and day. Of course, our sex life improved but so did all the other things we'd wanted to do. We actually took a surfing class together. Something we'd talked about doing but had never managed to find the time for before she got sick. Now we were out at the beach four days a week after work learning how to fucking surf!

I'll admit, I let things with Lily fall by the wayside for a bit. And when she called me on it, I knew I was in trouble. Not with Lily... I'm not sure she had it in her to chastise me. With myself. I redoubled things with her, spending nights talking to her before going back to my wife. Helen was still into it but the necessity of it wasn't there anymore and I could tell it was different for her now, too.

"Master... can we talk about something," my wife asked me one night.

"Sure," I said as I rolled over to look at her, "What's up?"

"Please tell me truthfully... do you love Lily?"

I looked at her, totally unsure what to say, "I... I... Maybe... I think so."

She nodded at me, satisfied with the answer. "Okay."

"Helen... tell me... what's wrong?"

"I'm the one who started you down this path... I knew what I was doing," she sniffled a little.

"Are you asking me to stop?"

"No... I have no right to ask that of you?"

"Fuck that... do you want me to stop?" I asked.

She looked up at me and she looked more vulnerable than she'd ever looked even at her sickest. "Y... yes... Master."

"Then it's done," I said. I pulled out my phone and deleted the texting app.

"What... really?" She asked with wide eyes.

"Yeah. It's done."

"But you love her..." she said.

"I think I might have grown to love her... but I already love you. You're everything to me, Helen. It was fine to grow close to her when you were okay with it but if you're going to be bothered by it then I NEED to end it now. I can't let it go on because someday, it might've gotten to a point where I was TRULY in love with her and who knows how I'd react at that point if you'd asked."

Helen just looked up at me and whispered, "John... I love you. Thank you."

I closed my eyes and kissed my wife, holding her in my arms tightly, "It's you and I, my love. It's always been us."

That was two years ago. I haven't talked to Lily since. I'd be lying if I didn't think of her. Often. My wife and I still talk about her sometimes, reliving the airport encounter is the surest way to get my wife turned on, in fact. Every time we drive in from out of town and pass that airport, I'm balls deep in her ass within ten minutes of getting home. But things are better this way because I don't know if our hearts could have taken it. As much as I love the romance of being in love with multiple people, I think it's a difficult thing to juggle. Something that requires just the exact right mix of people, circumstances and life situation. If we hadn't had kids and could have had Lily come visit for a couple weeks would things have been different? I doubt it but maybe. Definitely if my wife had continued to deteriorate, I think Lily would have been the rock I'd have leaned on. But I don't think any of that would have been better (certainly not the second scenario which is almost too scary for me to contemplate).