While I admire you arranging to have a gift delivered to my hotel room while I was in Houston at the conference, I was frustrated to see that it was a new chastity cage. I had not planned on wearing your dominance down in Texas. Actually, I had planned on finding some local or conference attendee and inviting her to my room. I had my freedom this week, and I intended to use it. Maybe I’d cheat more than once. In ten years of marriage, on top of five more years of dating, I had never cheated. Every now and then, I thought about it – longed for it, but you ran our house from the day we moved in together.
Don’t get me wrong, I have always been madly in love with you. However, you need a submissive man, and I am not always that way. It is nice to be a caged sub when I’m home with you, which is most of the time given my mostly remote work, but that work requires me to be “the man.” Frankly, I sometimes hate it, and the extreme of being your sub while I dominate finance balances it all out.
Conferences, however, were always the exception. And, occasionally, things feel out of balance. My cock cage is metal, and I can’t exactly wear that through airport security. Even the plastic ones have a metal lock. And, most of all, whenever I am home, which is most of the time, I am wearing one. I get release and orgasms once every two weeks, on the Fridays between paydays. You wear the key in a locket around your neck. You always said that you never wanted to advertise that your husband is a caged bitch. “That’s for me, and only me, to know,” you would say.
I studied the cage. It had a tight, grid structure. It was all some kind of wire and shaped like a limp cock. It looked like it wouldn’t have issues with it going through the checked-bag security at the airport. Out of curiosity, I tried it on, and I could feel that it had some room to grow, but not much. I’ll admit, I liked thinking about how much it would hurt to wear it. I could picture you teasing me like you always did. Watching you cum every night while I just had to lay there and suffer was something I’d miss this week.
Well, I’d only miss that a little. I wouldn’t miss it at all when my cock was buried deep in some beautiful hook-up. I wasn’t even above calling an escort if I didn’t pick someone up before Wednesday.
So, while I appreciated the gift, I set it aside in my suitcase. I’d wear it for you when I get home. For a moment, I was offended that you expected me to wear it while I was out here.
Sure enough, Monday and Tuesday’s flirting yielded no results. No buxom blonde felt my cock buried in her either night. I am disciplined enough not to jack off, at least.
I told you I was wearing it. When you asked to see it, I’d put it on, send you a pic, take it off, then get back on a dating app I’d downloaded on arrival. You said that you liked the red wire look against my skin.
Then it happened. Fuck, she was perfect. Round, C-cup tits, a curvy bubble-butt, thin waist, blonde hair and green eyes, and just enough skin showing to let me know she was available. The red dress she wore was perfect. I approached, bought her a drink, and we chatted for a couple hours. This was exactly what I wanted to experience – even to the point of waiting maybe too long before responding to some of your texts.
I told her that I was separated, and she followed me up to my penthouse suite.
Fucking her made me feel like a college stud again, back when I was on the basketball team. I remember how I would not wear underwear or undershorts in my game shorts so my sizable cock would just barely show itself off to the sorority girls.
She tasted fantastic. Her pussy was sweet and addicting. It was hard to keep my tongue off her clit. Her asshole tasted just as incredible. I slid myself into her wetness every way I could. My cock felt electric, like it could explode into a fountain of cum at any moment with every thrust. And she rode me like she owned me. The first time I came, she was bent over the couch with the curtain open. Anyone in any of the hotels nearby could have seen us. I told her I was going to pop, and she fell to her knees and I painted her face with thick, gooey cum. It was like a typical porn cumshot and I was somewhat proud of myself.
She went to the shower after. I followed her, and we fucked again. Back in the bed, we fucked once more. I woke up to her rubbing against me in the night. I roused her and we fucked again. We fucked another time before I left for the conference. She said she’d come back the next night too. “You fuck like a married man,” she said. “I hope you are. I hope you lied to me.” That was the sexiest thing I’d ever heard in my life.
When I came back to the hotel during an afternoon break, I visited the desk after receiving a message from them. I got your second gift and opened it in the room. It was the same chastity cage. This one was purple, and it was smaller than the last one. You commanded to see it on me, and I obliged. I took it off and put it in my bag with the other one.
As she promised, she came back the next evening. She wore a silky purple dress that accentuated her just as much as the red one from the night before. We went to an amazing dinner, had more cocktails, and then, back in the room, my cock found its way into her tail. “Stick your married cock in my ass,” she said. I was all too eager to oblige. In all, we fucked thrice that evening and night.
The next day was Friday, and I got your third gift. A small cage, the same model, but this one was blue and small enough that it hurt somewhat to put it on. There was no room to grow at all. I knew this one would make me suffer at home, and I was certain you’d make me wear it.
The conference concluded Friday evening and I was scheduled to fly out the next afternoon. She and I decided to make the most of the night. I met her in the lobby, and we ordered room service for the night. She opened the curtains and slipped off her dress. It fell to the ground and stayed there, a blue pile on the floor, for the rest of the night. I felt like I made love to her. There was a real ecstasy in every thrust, every kiss, every lick that night. She came maybe a dozen times, and I filled her with my seed thrice. It was passionate, something I felt like I never experienced in our bedroom.
I knew, when we left that room in the morning, that I’d miss that. I’d even miss her. I hoped I’d come back to Houston at some point – just to see her. “Was this the start of an affair?” I wondered. I never once felt wrong. You would never know.
Then I got home.
I walked into the bedroom to find a display waiting for me. Three dresses laid on the bed: a red one, purple one, and blue one. On the purple one was a letter.
“I booked a room with a view of your window. I hope you enjoyed your gifts. And your trysts. I wear white for you. White like a wedding dress.”
I looked down to see another box on the bed, and I knew what was inside. I even guessed the color before I opened the box. It was a white cage, smaller than the blue one.
“No orgasms for three months,” read the note inside with the cage. “These dresses are your new uniform around the house. Unless you need to be on a video call.”
I was devastated, and incredibly turned on. I probably could have cum immediately in that moment. I turned around to see you in your white leather dominant lingerie. You opened the locket with my old key inside, prepping it to house the new key. “The cage never comes off in those three months,” you said.
Author: rvaanonguy1
So, you want to stay? (Part 2 of 2) [Swinging][Threesome]
When you whispered, “I love you,” in my ear while we fucked the other day, I wondered if my psuedo-revenge plan was as well-thought through as I had imagined it was. Had this been what you wanted all along?
I didn’t think you’d wanted to get caught in a brief affair. I’d readily admit that I had gotten lucky in both spotting that suspiciously shaped bruise on your ass, but I was surprised when you came clean so easily. Had your nerves been from hoping I would agree to this new lifestyle of ours?
Regardless of whether you had a counter-plan or not, we were in it now – in more ways than one. You fucked the man you cheated with, I watched him fill you with cum, he left and I spanked you until your ass was raw while his cum leaked out of you, and then we fucked with what was left of his cum lubing our passion. You whispered those words, and I filled you with my own cum. I was more committed now to this idea than I had been before – even just moments before.
So, you want to stay? (Part 1 of 2) [Hotwifing][Cheating]
I repeated myself after you sat there staring back at me with weepy eyes. You felt guilty down into the darkest recesses of yourself – even in the place that made you think that what you did was a good idea to begin with. I’d never tell you that you could have gotten away with it; I hadn’t even had the slightest inclination something was amiss that day.
“So, you want to stay?” I asked, for the third time. I could tell that you were sitting uncomfortably on my couch. It was like you could feel the cushion pushing you off of it or something. I made sure that my voice wasn’t rising. I figured you’d calm down if I stayed that way myself.
You finally nodded. You didn’t take your gaze from my eyes as you did so.
“I have a proposition for you,” I said. You cocked your head slightly, and your thoughts started racing. What revenge or humiliation could I have in store for you? You felt like the price to stay would be some firm punishment of some kind, but you wondered what bridge would be too far. I suspected that you thought I would say something like, “spanking,” or, “I need the pass-code to your phone,” or, “I need time away from sex with you.”
Match-Breaker [Cheating][Infidelity][Proposition][Office Relationships][Dating Services]
You sat across from me wearing what I assumed was one of your nicest evening dresses. It was pink and shimmering in the sun as the afternoon sun shone through the windows in my open office. You were made up tastefully. I always thought you looked like the kind of woman who wouldn’t need my matchmaking services. But, you weren’t looking for just any lame boyfriend – you never had trouble getting those. I had counted on that.
“I trust that you have read, thoroughly, my client’s terms and conditions.” You smiled and nodded, and your charm started to dawn on me. Normally, I can tell when one of my female clients is lying, but you were different. In that moment I started feeling like this match might work out exactly as intended. I like generating repeat business, but you made me think of the bigger picture.
“He has read mine?” you asked. I assured you that he had. It’s been my experience that men, even very particular ones, never fucking read the contracts. After the first few years of doing this work – without a partner – I started reading the contracts to them to save myself from future headaches. “And he’s fine with all the key points? I expect my independence.”
“He’s agreed to all of them, point by point,” I said. “He often travels for work alone,” I began, “and understands that you would want to do the same. As we discussed, and as you agreed, both solo vacations would take place while he travels for work.” You nodded, visibly recalling our negotiations about that point. “And he has already signed a purchase agreement on one of you preferred city apartments.” You smirked, and it’s like I could see the machinations churning behind your eyes. “He had no requested alterations.”
“And I had none for him,” you assured. For almost every other woman who’s walked into my office seeking a significantly older, more successful potential husband, I would have assumed that this would be the final one-on-one meeting. Not you. At least, I hoped it wouldn’t be. It’s not hard for me to remain professional, even with the most desperate women who meet with me.
My eyes never traced along the edges of their dresses over their thighs or down between their breasts. I never stumbled over words or lost focus during the “past sexual experiences” interview, no matter how dirty and enticing the stories were. My eyes never wandered from tattoos, piercings, or scars in the “bodily inspection.” For what it’s worth, yours were both dirty and enticing. I never saw dollar signs in my eyes, anticipating that any of them would ever be back at my glass table. I never hoped I could steal a match from my male clients. And, most importantly, I never felt my cock swell in my pants. None of that was true with you.
I always put in a clause about the “termination of a relationship” and how neither I, nor my business, are responsible for unforseen circumstances. Consequently, I refuse to match anyone who expects traditional fidelity with anyone else who I think could present an issue. But, never has anyone explicitly asked me, “Are there clauses specific to future indiscretions or infidelity?” You uncrossed and recrossed your legs when you asked.
“No,” I replied, “there are no specific clauses.” Trying not to show you my own interest in you, I leaned back and pressed my tie down along my shirt. “Why do you ask?”
“I’ve had experiences,” you replied. Your face didn’t say that you’d been cheated on; in fact, it didn’t give much away at all. That, in and of itself, intrigued me.
“Experiences we should have discussed in the ‘sexual experiences interview?'” I asked.
You studied me. “Either you never suspected anything,” you said, “Or he’s into non-monogamy of some kind.” I said nothing, and did my best not to give you any indication either way. We were now in a whole new interview, and you were succeeding. “Maybe you think he’s aloof and wouldn’t notice or care.”
“You asked him for solo vacations,” I replied. “I would imagine that he pictured you getting fucked by a tanner, younger man on a beach at least once.”
“Imagine? He did?” you asked, erotic skepticism hung in your voice. “Or you did?”
I have prepped myself for these sorts of scenarios. Even if I was fascinated by you, those preparations wouldn’t give away the game. “If I said that he had?”
“Good,” you replied, “It’s likely to happen.” Your tone was both sensual and matter-of-fact.
“And, if I said that I had?” I asked in the same plain tone as I had asked the previous question.
“You may have cum to the thought, I think,” you said. “But I would imagine that a man in your position as a matchmaker would call this whole thing off if that was a problem.”
“I’ve done it before,” I said. “Many times.”
“Then why are you and I sitting here alone instead of the three of us?”
“I have a feeling that you have more ambitions than merely marrying a rich, middle-aged businessman.”
“I do,” you replied. “I aim to get fucked on a beach. And in that apartment he bought for me. And I aim to keep him the whole time.”
I scratched my beard contemplatively. “What if you didn’t keep him?”
“Why would I dump him if I can have everything I want?”
“Because I think I can offer more than that,” I said. You scoffed, expecting me to try to take you for myself. “I have a proposition for you,” I said opening the file far to my left. I wrote the document in that file when I started this service as something of a business fantasy. I’ve always hoped to pull it out, but I’ve never had the right woman in front of me before.
“Don’t try to sell me on something,” you said, sounding like you were thinking that some sort of jig was up.
“I’m not going to sell you,” I said, sliding the contract to your side of the table. “You’re interesting and clever. I was just going to let you read the proposition for yourself.”
You looked at me, puzzled, as I leaned back. You noticed that I hadn’t touched by cock, bit my lip, or did anything else suggestive. Your curiosity piqued, and you grabbed the pages. You read methodically. A cruel, fascinated, opportunistic look came over you. You leaned in a way that let your nipple peek out of your dress.
“How does this affect my current match?” you asked.
“It doesn’t,” I replied. I could damn near feel your sensual excitement ramp up to its highest level.
“You expect me to cheat?” You asked, pointing at the contract. “You want me to break up other relationships and marriages, be bait willing to be photographed, and you’ll pay me to do it?”
“Pay you?” I asked rhetorically. “You’d be my business partner; you’re paying yourself and our firm.”
Your eyes darted back and forth like you could see the future and were scanning it for potential downsides you were uncomfortable with. You smirked, and I assumed that meant you saw none. “What do you get?”
“Besides pay,” I began, “I have my perks, but I never expect you to cross any uncomfortable line with me.”
You thought for a moment and looked at the pen you used to sign the male client’s contract with. “A matchbreaking service?” you said to yourself. You pushed your chair back and stood up. In that moment, I thought, only for a moment, that you would storm out the door. I feared that I shouldn’t have shown you that contract, or that I’d fallen into a trap of sorts.
“I’m quite comfortable with you,” you said as you slid the straps of your shimmering pink dress off your shoulders. The dress fell to the floor revealing your slender build, slightly tanned skin, and handful-sized breasts. The tattoo reading “Rest and Repose” in Latin stood out from your right collarbone, and the sun bathed you in a sexual glow.
You leaned forward, grabbed the pen, and signed the document. Fuck, my cock was hard and I could swear that I heard the ink dry as I lost myself gazing into your eyes. I’ve wanted nothing more than I wanted you in that moment.
“Is this one of the perks you hoped for?” you asked, standing back up and showing yourself off to me. You rubbed yourself all over.
“I had hoped for this,” I replied, “yes.”
“When will you take your first photos of me?” you asked.
“When we break up your match: not until you’re ready,” I replied. “When we break up someone else’s… How soon do you want to get started?”
“How soon do you want me to be sucking your cock while you watch videos of me cheating with a married man?”
I knew you would be a fantastic business partner in that exact moment, and, since then, you’ve never disappointed.