Cuckquean Experience

“Open your heart to love but protect the love you already have” - Random Fortune Cookie

My name’s John and I love Cuck stories. But not the more popular Cuckold stories. Nope. My personal kink is Cuckquean stories. If you’re not familiar, I don’t blame you. I didn’t know the term until about five years ago But I’d always loved the idea. Maybe it’s the stories of genies and harems when I was a kid. Maybe it’s just biological. I don’t know. I just always liked the idea of having a bevy of beautiful, willing women.

The thing that really kicked my secret kink into high gear, however, was my wife’s poor health and the way she chose to cope with it. Or, more particularly, the way she encouraged me to cope with it. My wife is the love of my life. I have been the doting husband to her and our two children for the better part of two decades. And while I always had these thoughts of other women in the back of my head, I never once acted on them. Unfortunately, as my wife’s health deteriorated, she started carrying all the guilt of our waning sex life on her shoulders. After a year of having sex once a month (at best), she came to a realization.

“John, I think something needs to change with us,” she said quietly to me one night out of the blue. We were lying in bed, in the dark, watching her favorite show and trying to take her mind from the pain.

“Why? What?” I asked with uncertainty.

“I… I know you have… you know… needs.”

I looked at her, “Helen, I don’t…”

“Don’t do that, John. I know this is hell for you.”

I laughed, “It’s not… really, it’s not. It’s not ideal but you have it way worse than I do.”

“I know… I’m not saying I don’t. I just don’t want to be carrying this burden of ALSO making you unhappy.”

“You don’t. I promise,” I said and kissed her forehead softly. She snuggled into my arms, grunting with the exertion of moving.

“You need to find some happiness,” she whispered.

“Helen… I’m not leaving you. Ever.”

“I’m not telling you to, idiot. Maybe just… you know… find someone to help you relieve a little stress.”

“What do you mean?” I asked. I couldn’t help it though, the thought of what my wife might be hinting at was causing my cock to stir.

“Maybe… you know… find a girlfriend… a friend with benefits… or friends even. Just come home to me and maybe tell me about it afterwards?”

“Open my heart to love but protect you too?” I asked.

“Exactly,” she said.

“I… I don’t think I could do that,” I told her.

She looked at me, a little tear in her eye, “I think you can but I understand why you think differently. But know that if you want, it’s okay. And think about it my love.” She closed her eyes, tired from the days effort, and drifted off to sleep leaving me to think about what she’d just said. I tried to put the idea out of my mind but it just kept worming its way deeper and deeper into my brain.

The week passed by and we didn’t talk again about it. One week turned into two and then a month. The conversation was mostly forgotten. Meanwhile, I was was trying to finish my first novel. It was an undertaking I’d started when Helen’s health had first started to deteriorate. A hobby to help pass the time for myself. Now I was experiencing awful writer’s block. I just couldn’t the ending to come together and it was leaving me incredibly frustrated (not good for a hobby that was supposed to distract from my other frustrations). I looked around for writing forums on reddit and stumbled across r/dirtypenpals. It wasn’t exactly what I was looking for but, as it turned out, it was exactly what I needed. People post erotic writing prompts and you collaborate with someone to tell a story. Some of the interactions were purely platonic (despite the inherent sexiness of the endeavor) but some interactions turned into actual relationships. 

My first serious one was with a girl named Constance. She was an Asian girl from Toronto who had a real fetish for Overwatch erotica. Violent Overwatch erotica. I liked her but she had… issues. The scenes she wanted me to write were… I think extreme might do gentle a word. I have no problem going dark with my fantasies but not that dark. It put me in this really weird mental place with her. When we weren’t talking about sex or writing the extended Overwatch novella that we were collaborating on, she was really cool and intelligent. I liked her a lot. When she ghosted me for a week (as it turned out, she was being stalked IRL by somebody and thought it was me) I was devastated. I realized that our flirting and sexy talk had built an actual emotional attachment. The whole thing had grown slowly and I hadn’t even realized what was happening. It was my first warning sign about this lifestyle and what it might entail emotionally.

I talked to Helen about it in the week when Constance disappeared.

“So I did something dumb,” I told her.

“What?” she asked.

“I… I started talking to someone… online,” I said, not sure how to tell the story.

“A girl?” she asked.

I nodded, ashamed of what I perceived to be my own weakness. Helen saw it differently. She rolled over on her elbow, wincing only slightly but a twinkle in her eye spoke of another emotion. Intrigue. “Tell me…” she said with desperation.

“I… I… we just started trading stories… well, basically making an erotic fanfic story.”

“What about?”

“Uhmm… that shooter of Blizzard’s,” I said. Helen nodded and I continued, “She… she likes some pretty extreme stuff,” I told her.

“Like what?” Helen asked.

I didn’t want to share all of it. It just felt like too much. But I gave her the brief outline. “Women being tied up… spanked… smacked.”

Helen rolled onto her back and slid a hand into her panties. “And you guys tell each other the story?”

“Sometimes it’s mostly me telling it,” I said as I watched my wife finger herself slowly. The pain she was in usually kept her from getting turned on but if she was ABLE to get turned on, she could push past it, at least for awhile. 

“Do you just tell the stories? Or… or do you talk to her?”

“We talk a lot too… we’re kind of friends.”

“What does she look like?”

“I don’t really know. She’s half-asian and 24.”

“Does she live close by?” Helen asked, “Do you want to meet her?”

“Seriously, Helen?”

“Yessss,” she said. 

“Yes, I want to meet her. No she doesn’t live close by. Other side of the continent actually. Toronoto.”

“What do you talk about?”

“All kinds of stuff. Computer games. Politics.”

“Sex? With each other?”

I paused, “Sometimes.” My voice was quiet, still unsure of where this was going. My wife’s back arched as she continued to play with herself. I reached over and stroked her impossibly hard nipple, grazing it through her thin t-shirt. She shuddered and moaned with arousal. “She calls me, Master,” I said into Helen’s ear. That did it for her. She came so hard she couldn’t keep quiet. I had to clamp my hand over her mouth to keep from waking the kids. Her whole body shook as she screamed into my palm. 

When she finally calmed down, she looked at me and spread her legs lewdly. “Fuck me… Master.” My wife had never called me that before. I’d never thought to ask. I thought I’d liked it when Constance called me that in text chats, but to hear my wife say it out loud. Let’s just say my cock had never been harder. I rolled over on top of her and within moments we were fucking harder than we ever had before. I was pounding her and she was moaning into my ear, “Fuck me, Master. Fuck her, Master. Fuck your little fucking Asian fuck toy, Master. Do it. Do me. Do anyone you want, Master.” We both came hard and I collapsed on top of her as she showered my neck, cheek and shoulder with kisses.

“I love you. I love you. I love you,” she whispered as she wrapped her legs around me.

“Are you okay?” I asked, concerned.

She nodded, tears coming out of her eyes but smiling, “It hurt a little. I’ll probably pay for that tomorrow but it was worth it, lover. That was so good. I needed that. You needed that.”

When Constance showed back up online, I was relieved. She told me about her stalker and her fear that it was me. She had texted me minutes after the police told her they’d arrested him. She needed to know. I was ecstatic and we started things back up right where we left off. When I told me wife, she was also ecstatic and this time, instead of keeping it a secret, I told my wife everything. I rounded off some of the rougher edges of the story. Some of the violence that Constance pushed towards, I left out. Which was just as well because my wife didn’t care about the fanfic at all. She wanted to know about Constance and I. She pushed me to push Constance. To build a relationship. It became her obsession. Constance was understandably concerned about sending pictures but Helen suggested that I ask for an audio. Constance agreed. She was going to edge herself nightly for a month and then send me an audio of her first orgasm after 30 days of denial. My wife loved the idea. I loved the idea. Constance seemed to like the idea.

And then, the night of her birthday. The night she was finally going to have that orgasm, she ghosted me for good. Funnily enough, the second time didn’t hurt as bad as the first. I’d come to grips with the emotional attachment I’d let myself have and had guarded against it. I didn’t want to get like that with a stranger from the internet. My wife, on the other hand, was devastated. We’d been having sex two or three times a week thanks to the sexting Constance and I had been having. Considering that once a month had been the high water mark for the last couple of years, that volume had been amazing. Helen (and probably myself) hadn’t been this happy in a long time. We’d made plans to listen to the audio together. We’d sent the kids to my parents house. Instead, we were left empty handed and sad. 

Helen was upset at first. Angry and sad. However, she redoubled her efforts.

“This works, John. Tell me I’m wrong. Tell me our sex life has been better than this? Even before I was sick,” she said. There was a fire in her eyes. Not anger. Determination.

“It has been amazing, but I don’t know that we should continue,” I said.

She walked up to me, “No… we should do more. You should find more little sluts to mind fuck online,” she said. Her voice was sultry and deep as she whispered into my ear. “Make them call you, Master. Bend them to your will. And then bring them home to fuck them for real.”

“Are you serious?” I asked. I couldn’t believe what I was hearing. It was my own personal fantasy come to life. As I’d read more about Cuckqueans, I realized that there were really two major types. There were the ones that got off on being treated as inferior women and wanted their husbands to fuck “superior” women. Some of those stories were hot but I didn’t want to treat my wife like she was crap. I loved her. I much preferred the stories where the wife was a willing participant. Where she actively encouraged her husband. Sometimes even going out on dates and picking out women for her man. 

So with my wife’s encouragement, I went back online to find other girls. There were a couple that I found but the relationships were fleeting and often unsatisfying. There was the British girl who loved golden showers (not my thing). There was the housewife that had the two most disparate fetishes I’ve ever seen. She liked demon porn and she liked erotica about being fucked by her son’s bully. I met another Asian girl who wanted to steal me away from my wife and pay for penis enlargement surgery (is that even a thing) to give me a foot long cock that she and her friends could be an endless supplies of pussy for. I’m telling you guys, people online are WEIRD.

My wife enjoyed all of it but only in so far as I did. If I came to bed after a mediocre encounter, she just couldn’t get into it. It’s when I came to bed obviously hot and bothered that we had crazy, often mind-blowing sex. Through it all, I made sure to keep that guard up. Helen never asked but I’d made it a personal rule. No attachments. 

That continued for almost half a year. That’s when I met Lily. She was… a revelation. She was perfect. She was a middle school math teacher in Chicago. 27 years old. She didn’t come online to tell stories. She came to find a Dom. She came to find someone to teach her. Train her. Mold her. She was a perfect fit for me and we clicked instantly. When I told my wife about her, she also sensed that this one was different. We fucked for nearly an hour after my first time playing with Lily. As Helen laying in bed, gasping from her third orgasm while my cum leaked out of her she looked at me and asked, “You like this girl?”

I nodded, “She seems pretty cool and she hits all my kinks, I think.”

“Then make sure you keep her around for awhile. Especially if you’re going to fuck me like that after.”

I didn’t need that suggestion. Lily enflamed me. Truthfully, even more than my wife at times. I felt a need for her that I hadn’t felt in a long time. The kind of lust that comes from someone who pushes all of your buttons perfectly. Who says exactly the right things at exactly the right moments. I talked to Lily almost every night. Sometimes life got in the way and we couldn’t play but most nights we did something kinky and fun. She sent me an audio of her orgasming within the first couple weeks. She sent me pictures (face hidden… smart girl) soon after. She was incredibly cute with a perfectly spankable ass. Now that I had a picture for the words and the voice, I knew I really wanted her.

“I imagine flying into your city. You’ve told me what to wear. What would you make me wear, Master?”

“A short, loose dress. No underwear.”

“None, Master?”

“Stupid little cumsluts don’t get underwear, baby.”

“You’re right, Master.”

“I’d meet you at the airport. I’d know you instantly from the collar you’d be wearing.”

“A collar, Master? With a little dress… what will people think?”

“Probably that you’re a slut,” I replied simply.

“Is that what you want? For them to think I’m a slut?”

“Yes. MY slut.”

“Yes, Master. Your slut. Always.”

“I’d walk up to you and whisper your name.”

She replied, “I don’t think I’d be able to talk, Master. I’d be too nervous.”

“Would we be just John and Lily, slut? Or would we be Master and kitten?” Kitten was the only thing she liked that I thought was a little odd. She wasn’t into actual petplay (thank God) but really liked it when I called her Kitten in moments of sweetness. Of course, she also liked to be called a dumb bimbo bitch so there was plenty of variety.

“Whatever you want… Master,” she typed back. I remember my hands trembling at seeing those words on the screen. My cock was rock hard and I was stroking it.

“Really?” I asked.

“Yes, Master.”

“Is that the truth or just fantasy, Lily?”

“100% the truth, Master. Anytime. Anywhere.”

I came hard, shocking myself with the suddenness and forcefulness of the orgasm. We talked more before I was hard again and went back to bed to fuck me wife. Lily understood where she stood. She understood that Helen was my priority. Lily even got off on it a little. She’d played with other married guys before. She’d always been concerned about it. Being the “other woman”. She distanced herself from the idea because she didn’t know the people but that meant she couldn’t let it be real. Because Helen knew everything and not only approved but encouraged it, it allowed both of us to let our guard down. To say we fell hard for each other would be a dramatic understatement.

“Are you sure you’re okay with this?” I asked my wife one night after another round of crazy sex.

“Of course, Master,” she said. That was the other thing that had happened thanks to Lily. She helped me fully understand what my own kinks were. Lily was a completely blank slate, turned on by her partner’s arousal. I could explore whatever I wanted with her and find what I liked. Then I went back to Helen and shared. It turned out, almost everything that I liked, Helen also got off on. Not 100% but pretty close. Somehow having this stranger on the internet to share intimacies with had raised the intimacy between my wife and I ten fold. 

“Up to now, it’s only been online… fantasy.”

“You’ve fucked her in your mind thousands of times, Master. Haven’t you,” Helen asked while stroking my cock. 

“Yes,” I gasped.

“But you’ve never gotten your cock sucked by that whore?” she said as she leaned forward and took my cock deep into her mouth.

“No,” I said, enjoying the sensation. My wife had worked really hard to be able to deep throat me and it was something she was rightfully proud of. She smiled at me then slung her leg over me. The funny thing about Helen was that, once she got turned on, her pain threshold was through the roof. I’d known it for years as we played with her nipples or I spanked her. There were times when she was so aroused that you almost couldn’t pinch her nipples hard enough. That same variable pain threshold worked to our benefit thanks to our new online friend.

“You’ve never slid into her nice, tight, bald pussy have you?” she asked as she sank down on me with her own smooth cunt. 

“No,” I moaned out as she wiggled her hips. 

“I want you to, John. I need you to. Fuck her. Use her. Do all the nasty things to her you want then come home and tell me about it.”

“What if I want to bring her home?”

Helen’s eyes rolled as she shifted her hips and squeezed me, “Then do it?”

“What if I want to watch her eat your cunt while I fuck her from behind.”

Helen’s eyes looked at me lustily. Helen didn’t have a bisexual bone in her body. She knew I knew that. “Then do it. Make her do it and my cunt will gush, Master. I want to see you… dominate her.”

I rammed my hips up, filling my wife with cum as she collapsed down on me, “I didn’t cum, Master,” she said.

“Good girl,” I told her. That was another thing that I’d discovered I loved. Orgasm denial. It was the one thing that Helen liked that Lily didn’t. Lily was a needy, greedy little slut. She could go a couple days without an orgasm but she got cranky much longer than that. She’d do it, but she didn’t enjoy it. She liked the kink. The momentary denial. The teasing and making her earn it. But ultimately she did want to earn it. 

Helen, on the other hand, reveled in being deprived of orgasms. At first, she’d gone a week without one. Then a month. I teased her about only giving her one a year. She loved the idea. She said it made her feel so wonderfully submissive to me. Like she existed purely for my pleasure. 

Despite everyone being on the same page, real life makes these things hard to work out. Especially from halfway across the country. Sometimes, however, fate intervenes.

“Master, I’ll be offline for a week soon. I’m going to visit my friend in San Diego,” Lily told me one night.

“Really? San Diego?” I said. My heart quickened. I’d never told Lily where I lived other than “somewhere in California”. “When?”

“Week after next, Master.”

“So you’re just flying in and catching an uber or something?”

“Yes, Master.”

Interesting, I thought. I briefly considered waiting at the airport for her and surprising her. Despite all of our communications, I really didn’t want to be a stalker though. Besides, there were practical considerations to take into account like maybe her friend showing up to pick her up.

“Slut… I live in San Diego,” I said.

Immediately, the message app pinged with a request to chat. Normally, we just texted. It made it safer with kids in the house. I picked up the call and put the phone to my ear. 

“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 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 her condition weren’t 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, now 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 words “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 in the far corner. I’d found a large fan 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 do 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 fat 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 marked. The new medication was a three weeks on, one week off regimen and the results were almost immediate. 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 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 app. 

“What… really?”

“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. Everytime 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 having multiple people you’re in love with, 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 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). 

Open your hearts to love but protect the love you already have. It’s the most important life lesson I’ve learned.