A Cuckolds Journey - Pt. 01

The End Game

Leah lay their shaking from her orgasm and tears in her eyes. Not tears of sadness, this is just what happens when she has a 'really good' orgasm. The first time it happened with me, she had to assure me that nothing was wrong and I should absolutely keep going. Keeping with tradition, when it started to happen tonight, I told Aaron that it was nothing to be concerned about, she was happy and where she wanted to be.

A little bit later after I escorted him out of the hotel room, I returned to Leah still recovering on the bed. I gently spread her legs so that I could see the mess they made together. I slowly started to crawl on the bed, giving soft kisses to her toes, feet, and on up to her thighs. I went slowly. Breathing in deeply as I went, noticing the scent of cum getting stronger as I went. As I reached the apex I looked up, catching Leah's now focused eyes. This wasn't the first time I cleaned up after someone, but even now she looks at me hesitantly.

"Are you sure?" she asks with her eyes and a slight worrisome look forms around her lips.

I answer with a devilish smirk and lower my eyes and mouth. The taste is sweet, salty, and a little musky. My cock strained even more against my cage. Eager for that which has been denied on this vacation. I couldn't be more ecstatic.

As I savor my desert and the glow of my wife, I think about how we got here.

The setup...

Leah and I met playing on a coed softball team. When we first met we were at different points in our lives. Her getting out of a toxic relationship with her first real boyfriend, and I about halfway through my first marriage. We never had any intention of being together and in fact we rarely talked outside of the games, but fate had us get out of a variety of relationships at the same time and we decided to give friendship a go.

Leah stands at a powerful 5'1". What she lacks in height she makes up for in tenacity. Wide hips, matched by 36DD breasts, and short black hair. Her personality and smile drew me in almost immediately after we started 'talking'; two things I never really paid attention to. I knew pretty quick that I wanted to make this woman happy, and I was willing to do whatever.

I stand an easy foot over her, while not a professional athlete, I've always had a more athletic build to match my natural athleticism. Short wavy hair, light blue eyes...I've been told I'm quite the looker though I have some work to look like one of those 'handsome' actors or a model. I only say a little about me to show that even if someone were thinking about approaching Leah while I was around, they likely would decide not to when they saw me, understanding that it would be a hard sell on just looks (at least this is what I say in my head!)

A couple of months into our dating life we were relaxing in a hot tub with her back against my chest, drinking wine, and talking about whatever came to mind. This is the moment that transitioned our relationship from a vanilla one into one of sexual exploration.

"Have you ever stuck something up your butt?" Leah asks.

I don't know if she felt my cock twitch on her back, but my hesitation to respond prompted a repeat.

"Did you hear me? Have you ever stuck something up your butt?"

I awkwardly reply, "Well, yes...sure."

"Did you like it?"

"....hah...yeah..."

That soon led to a vacation with her putting a plug in a man's ass for the first time; me wearing panties for the first time (it was part of a game, but still), impact play, and my first time tonguing anyone's ass.

That in and of itself could be a whole story, but that's for a different time. This story is how we progressed from ass play into the hotwife lifestyle.

Learning boundaries

Things progressed much like a rollercoaster for the next couple of years. We would have the ups where we would explore pegging and machines, and the downs where we focused much more on our self-growth and growth as a couple. We ended up getting married and the wedding night is what kicked my desires from the subconscious into the conscious.

As we get to our room, sweaty from a night of dancing, we strip down to nothing, trying to decide what to do.

"I'm hungry." Leah states. She gets like this after a few drinks.

"Ok, well what do you want?

"I don't knowwww!" she exclaims as she flops onto the bed, face down with her phone in her hand. She's already looking at delivery services that are open at midnight.

I ran my hands up the back of legs, "I know what I want."

"Well too bad. I'm going to get some tacos. Do you want any?"

"Sure, get me whatever" I say as I continue eyeing my true desire. My hesitancy gives way to lust. I laid down as much as I could and put my face between her cheeks.

"OOH! I haven't showered!" Leah softly screams but doesn't make any real effort to get away. I take this as further invitation to feast. I can smell her pussy, I can smell her sweat, I am drunk on both scents. I don't want anything except to relish her scent and taste. I spend the next 10 minutes making out to her ass as she finds what she wants to eat, orders, and finally puts the phone down.

"Well, I feel fantastic now. Thank you!" Leah rolls over with a little bit of pleasured exhaustion on her face.

"I should be the one to thank you, my love. I could do that to you every day" I say as I lick my lips. I've always had a bit of an oral fetish.

After this I made it a point to go down her as much as possible. Always reinforcing how amazing she looks and how delicious she tastes.

Over time I revealed to her that I wanted to be locked up in chastity. She said 'ok', though it wasn't really something she understood or got anything from. I made sure that she knew that she did, in fact, get something from it.

I worked to make her home life relaxing and inviting. I offered massages often (no happy endings expected unless she wanted), as well as various ways to get her off without my cock or orgasm. I started to use a strap-on for her while locked, I would use toys on her, or suck on her nipples while she masturbated; whatever she needed to get off.

"Can you be unlocked and cum in me?" she asks after one such event.

"Of course...can I go down on you after I cum?"

"Yeah...I suppose that's ok" she says calmly.

I almost came right then. She's never been this willing before to let me go down on her after sex. I'm even more eager now.

I took the cage off and returned to her. She's got a vibrator out as usual; she's rarely been able to orgasm from penetration alone. I enter her slowly, she's always so tight. It's hard not to cum instantly. She's never NOT felt amazing. I start to cum, I pump faster. She's getting wetter as the cum mixes with her. She's breathing heavy. I lean into her and kiss her as I continue to thrust. The vibrator between us now, I push down and add pressure to it. We passionately kiss as we find our rhythm. I move down to her nipples. She's recently learned she loves having them suckled and bit. This sends her over the edge, and she starts to shake.

As I get back to my knees I slowly ease out of her so that my reward does not escape before I'm ready. I look up at her, her eyes are still rolled back. With no more delays I put my head between her thighs. Kissing her clit gently, I begin to make soft licks up and down. She's sore, I go slower. It takes longer than I expected, but eventually her taste changes. I can taste something else. I quicken my pace. I use my fingers to gently probe inside and coax out more. After a couple minutes it seems I've gotten as much as I going to. I think that the next time I need to not be so deep.

"Well, I guess I don't have to worry about that dripping out now!" Leah says as she gets up and heads to the shower.

Later that night we are cuddled in bed watching tv and we start talking about whatever comes to mind.

I'm the first to pose a question: "How would you feel about roleplaying?

"I think it could be ok, but I would need specific directions. There's a reason I don't do improv."

"Well, we could do the stranger at a bar scene."

"Like what, we pretend we don't know each other?"

"Yeah, something like that, maybe we see if other guys will hit on you first, then I'll come in and flirt later and you'll 'come home with me'"

"Wait...you want guys to flirt with me?"

"Well, to be fair...you'd probably have to flirt a little with them."

"I'm not comfortable with that. Guys are crazy, if they think I'm flirty they're going to be expecting something."

"You don't need to openly flirt, but if they talk to you, you can just talk to them rather than dismissing them because you're married...they wouldn't know you're married."

"So you want me to leave my wedding ring at home too?"

"Well yeah, we both will. That's the point. To pretend we're not married or together, flirt like we don't know each other, and then leave together."

"I don't know about the other guys thing, but we can definitely pretend to be strangers."

The test run...

Two weeks later we make the plan on a Sunday night, away from the overly loud and obnoxious nights, but still lively enough and with a more mature crowd closer to us. We go to a bar with a dancefloor outside of our normal range to reduce running into people we know. I get their first and find a spot where I can observe the room without too much head movement. Leah walks in with a ruched dress that hugs her figure, but loose enough so that she can dance. She put on a deep red lipstick, some heels that make her ass pop even more. Her hair is up in a styled messy bun, a look she knows I can't resist. Her looks is designed for her husband-in-secret, but we soon find out it's quick to pull in someone else.

She knows I'm there, but she hasn't spotted me yet. She sits at the bar and orders some wine. A man from the dance floor notices her. He takes a moment to scan her and see if there's someone else there with her. After the song ends he makes his way to next to her. She's almost finished the glass. She must be nervous.

He says something to her. She nods and laughs. She scans the room again and finds me. I give her a grin and a nod. She turns back around and the bartender hands her another glass, this time from her new admirer. I watch as they make their way to a table that just emptied. She seems to be enjoying it. As they both finish their drinks they head to the dance floor. I don't know the song, something lively.

She love dancing. It just looks like a bunch of jumping around to me, but she's enjoying herself. The music changes into something more sexual. The crowd cheers and shuffles about. I lose sight of Leah and the man. A few minutes in I spot them through the crowd. Her back is to him and they're grinding on each other. I'm grateful I'm locked up in my chastity cage. I can feel the swelling as I watch the mating ritual. I need a break.

I move from my perch and head to the bar. I don't need a drink, I've forgotten to drink what I had, but I need to not watch. I don't know how long I sat there, a few songs? Suddenly things were quitter. I turn around and everyone is slow dancing. Leah has her hands wrapped around the stranger's neck looking up. She's saying something. His hands move down from the small of her back to her butt and give it a gentle yet firm squeeze. I suspect she's not wearing much under the dress. I'm jealous; jealous of this strange man fondling my wife in front of me. It's not his fault, he doesn't know this was supposed to be a game. I want to go to her, but I can't move. I'm paralyzed. She moves his hands off her ass and turns towards the bar - towards me - I realize she's not wearing a bra. No wonder she found attention fast.

I turn to the bar. She stands next to me waiting for the bartender.

"I thought you were going to make a move on me tonight?" she says somewhat accusatory, but with a hint of mischievous.

"I was, but I couldn't seem to find an opening."

"So, what's your plan then? My new friend is getting kind of frisky. Should we go home? Are you going to pretend to want me? What?" She's now turned looking directly at me. I can't tell what she's thinking. I don't know how to answer.

"Leah, love. I'm about as aroused as I've ever been right now and want nothing more than to take you home. I don't know what I was expecting tonight, but this wasn't it. I don't know how else I feel. What do you want to do?"

"I'm having fun. It's nice to feel wanted by a stranger. That new feeling is something you forget about. I don't want to do anything with him, it's just nice to be wanted by someone else. I love you and only want you."

"Ok so we'll just..."

She cuts me off, "I'll just have another drink with him and a couple more dances. Then I'll make an excuse of why I need to go. Now, I'm going to point him out to you. When I do, just say 'Ok' and turn back around, find somewhere to sit where you can watch, or go home. We're off script, so as long as you don't bother me I don't care what you do.

She doesn't wait for a reply and does exactly what she says. I turn and look to where she's pointing. Say 'ok' and head back to my perch which is somehow still open.

Leah returns to her 'friend' with her drinks. They stand around talking and drinking for the next 30 minutes or so and then they hit the dance floor again.

The next however long is a blur to me. My mind is mixed with fear, anxiety, lust, pride at how hot she is and how quickly she found someone. He's a little more aggressive now having made sure she came back to him. He runs his hands down the side of her breasts and grabs her hips. She leans back and fully gives in to his hands. She turns around and grinds her ass on his crotch. She looks at me as she slows down for a moment. She bites her lip and continues, ignoring me again. I lose sight of them again. Sometimes I think I see the through the crowd. They look like new lovers.

Eventually I see them skirting back to the bar holding hands as they meander through the crowd.

She leans in to the man and whispers something in her ear. Then leaves him and heads to the restroom. I take this as my time to call an uber for us. As I get my phone out, I get a message from Leah:

"Go ahead and leave now. I'll meet you at home."

No further explanation. I don't know why I didn't ask for clarity. Instead, I call an uber for one.

I go outside and wait with the other patrons that are leaving. It's a busy night apparently and takes fifteen minutes for my ride to show up. As I get in the car I turn to see Leah and 'the man' leaving the bar in fits of laughter. As my driver turns around to leave, I see that he's sitting on a ledge with Leah on his lap. One hand is teasing at the hem of her dress. The other is trying to secretly grope a tit. Again, I feel my erection get disappointed by its cage.

It's an agonizing 45minutes home. I get inside and sit by the door, leaving the lights off. What seems like an eternity but probably only a few minutes go by, and I hear a car stop outside the house. I peek out the blinds and watch the 'the man' get out of the car and walk Leah up to the house.

I don't know what's about to happen, but I'm sure I don't want to be in the living room right now. I move to the guest room...I don't know why, it just seemed like the place to be. Fear, jealousy...eagerness for something to happen? Why am I eager for this stranger to be with my wife? This was supposed to just be some roleplay...right?

I hear the front door open and close. I try to block out everything.

I'm panicking.

I don't hear anything.

"Where are they?" I think as I pull the pillow off my head.

Suddenly a voice at the door, "Come to the bedroom."

I'm weak. It's difficult to get up. My knees are shaking. I feel like I'm somewhere else, like I'm not me, like I'm in someone else's life.

I make my way to the bedroom. When did this hallway get so long?

I enter the room and see Leah on her back, legs spread eagle, with my chastity key around her neck. Did she wear that all night? She's never worn it before...

"I need you to clean me up, hurry up before it leaks on the bed."

I'm in a daze, but I obey. Just like the first time I ate my cum out her, I go gently. I lap her up. I breathe her in. I can't focus on anything except the events of the night.

I'm happy? Yes, I think so.

My fear, jealously, angst are all erased for the time period between her thighs.

"If you do a good job in a couple weeks, I'll let you cum. Until then you stay locked up."

"How was it? Wait, two weeks?"

"The dancing was good, I really enjoyed that. Yes, two weeks, if you're good."

"..."

"Were you not asking about the dancing?"

"..."

"My little wannabe-cuck, at a loss for words. Didn't go how you thought it would? Well, there's nothing to worry about. Nothing happened tonight. I told him I really enjoyed his company and body, but I didn't have time tonight for more action. So, we'll meet again. He's looking forward to it."

"But I thought...you went in a car together...you showed up together...I..."

"Yes, I wanted you to feel what you would be going through. We groped each other and teased each other, but we didn't even kiss lips. If my dress was any shorter he would've got a taste of what's to come. Do you want a stranger to fuck your wife? Do you want a stranger to cum in your bride? Do you want to eat his cum? Would you like that little man?"

As she says this she slaps where my balls are. The cage making my average sized cock look like a baby shrimp. She giggles.

"Also, I think he's a little bigger than you, at least from what I could feel from his pants. So let me know soon what you want. I enjoyed myself way more than I expected, so with your blessing, I would like to taste something new, if you're willing to as well."

"Yes. Yes I think I do want that."

"Want what? Say it clearly so that there's no confusion."

"I want you to fuck this stranger. I want him to cum on you. I want him to cum in you. I want to clean his cum off of you. I want to eat his cum from out of your pussy."

Leah stands up from the bed and lifts me up to my feet.

"Good. I'm so happy you said that. Now, please go back to the guest room, I'm going to text him the good news and I really need to cum, and since you're not up to the task..." she pauses as grabs the key around her neck and looks at my crotch, "I think I'll sext him. Goodnight, I'll see you in the morning."

As she says this she shows me the door and closes it.

Looking at the door in shock and disbelief, I come out of my daze, go to the guest room, and collapse on he bed.