A Cuckolds Journey - Pt. 02

The now...

"Where are we going with this?" Leah asks as she gets out of the shower. Her afternoon fuck with Aaron all but in our memories and my stomach now.

In a couple hours we will be in the hotel restaurant having dinner with Leah's family. They don't do family vacations often, but when they do they like to go somewhere cheap and tropical. This is one such trip. We didn't exactly plan to find someone that Leah would want to have sex with but sometimes fate favors the bold. In this case, it was Leah in a string bikini with a shear cover up hanging out at the bar each morning before taking a swim. It only took 2 days before she found someone that kept making excuses to sit near her.

Back in the hotel room, I pondered her question.

"This" Is an ambiguous term, but I know what she's talking about. How far are we wanting to take this hotwifing thing? What is my role in it, and what is the goal for my role?

"I'm not sure. This will be the third guy in a year. The first one on a vacation though, so it's unlikely we'll see him after we're back home. I feel like we've just been too busy to sit down and really talk about where we're going." I'm surprised I had an answer. There's truth in the business.

"It's nice to be able to flirt and see what happens. I worry though that we haven't been intimate in a while. Not really. You eating another man's cum out of me every other week or so isn't enough. Not for me."

She pauses briefly as she does something in her beauty routine and then continues:

"I think if we're to continue, you need to be more involved. Sitting in a corner, in a closet, or in another room all the time is just making us roommates that share finances. "

"I'm not really sure what you'd want me to do. I..."

She cuts me off, "If you're going to stay in chastity, then what you can do is actually really simple. You can fluff him, you can fluff me. You can do whatever you're told. The point is that you will be involved if we keep going with this."

I think about what she's saying. These are kinks I introduced to her: chastity, hotwife, cuckold. She tried each, and found out that enjoyed them. Would I be ok with stopping? Would she? I've never even touched another mans cock. There's been a clear line between the cock and what comes out of it. I don't know how I feel about being that involved.

"Well, you've tried what I wanted to so far, it's only fair I try what you are suggesting.

Do you have an idea of how to progress?"

She leans out of the bathroom and gives her signature devil smile, "Oh, yes. We're

going to start tonight."

She tosses a box to me, "I thought you would say yes. Open that up. You'll know what to do."

The past and the leadup...

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14 Days until 'The Day'

I didn't sleep well. My cage was suffocating with thoughts of what I witnessed; with thoughts of what's to come.

Leah took charge of the night and took what supposed some roleplay of us acting as stranger, and turned it into actually picking up a stranger. The fondled each other in public, in front of me. They grinded on each other and held hands, in front of me. I couldn't reconcile my wife with this other person.

"Good morning love."

I wake, not realizing I actually slept. Leah is leaning over me, waiting for me to leave dream land.

"Ugh, morning." I'm still drained. How can one be so tired and not be able to sleep?

"I'm headed to work. There's coffee ready for you. I got us reservations tonight at 6, so please be ready by 5:30." She gives me a kiss and heads out.

I'm wondering if she still plans on going through with her date in two weeks. I wonder If I'm still ok with it. I need to do some soul searching, but I don't have time for that. Never enough time. I need to get to work, though luckily I work from home so it will take me all of five minutes to show up.

As the day goes on and things start to die down, my mind starts to wander. "Why are we going out tonight? Did I forget some occasion?" I don't know who I'm talking to, maybe the wall will respond.

I scan the calendar. Nothing.

Well, I suppose that means it's about last night. Did something happen after I left the room? It's 5pm I'll find out soon enough.

Leah arrives while I'm in the shower. When I get out, she's already changed into a cocktail dress. I've always loved her in a dress. I stop and stare, taking her in. How did I get so lucky?

"Hey...stop staring and get ready. We need to leave in eight minutes."

I hurry up and get dressed, luckily I don't have to do much to be presentable. We get in the car and she puts the restaurant into the navigation. It's 25 minutes away. I start to plan on how to say what I want to say.

Leah gets there first, "Listen...I know last night didn't go as you planned. I'm sorry about that. I got a little carried away. I was just having so much fun, and you didn't seem like you were going to tell me or Alex to stop. I got a little annoyed at you if I'm honest and decided to really push the boundaries."

Alex. Alex is the man my wife wants to fuck. It sounds so wrong...why do I not say something?

"I need to know how you really feel about it...now that we've had some distance from it. I won't do anything you're not 100% sure on. This is all for you, even though I'm clearly getting the better deal."

She nervously laughs. Bless her, trying to lighten the mood.

"Leah, I'm all over the place. Watching you two last night, I was hypnotized. I couldn't take my eyes off of you...off of him running his hands over your body. I was aroused, I was jealous, I was anxious. I just wasn't expecting that to happen."

She put her hand on my lap, gesturing for my hand.

"I know it wasn't what was planned, and that can be uncomfortable. Other than having things more planned, what would make it better for you?"

"I don't know. I think not being there and not in the know probably would've been better in that situation."

"So if I do this again you want to just wait at home?"

"I think so...yes. I can get the details from you later, but watching the flirting is just too much for me right now."

We arrive at the restaurant and I let Leah out at the front door while I go and find a parking spot. I find Leah at a table near the center of the restaurant. It's not that busy, maybe a handful of other couples. I sit down and have what one could call a pretty normal dinner. We talk about tasks around the house that need to get done, work, and so on. Things were as normal as possible between us, as if nothing had happend.

"So how's it going over here, any refills? dessert? or are you ready for your check?" our server asks.

"Can we see the dessert menu please?" Leah asks without even pausing to ask me. We almost never have dessert, and when we do we often share it. Maybe she's still annoyed by my behavior last night. "Oh, and I think I'll have a refill too. I'm not driving after all!"

"Of course, I'll be right back with both."

"Everything ok love?" I ask, "you seem like something's on your mind."

"I can't think of anything that would be wrong right now. I've enjoyed properly catching up with you, we just don't seem to get a lot of these moments anymore with how busy work keeps us."

"Here you go miss." The driver places her wine down and hands her the dessert menu.

"Thank you, we'll take a look and let you know." Leah takes a heavy sip and then opens the menu.

"Ah, well that looks good, or maybe that. I many need help with this hun." She's already handing me the menu.

As I open the menu I'm met not with a list of desserts, but rather of a collage of photographs. "What is...." I begin, but then I see it.

"Well, anything you like on that?" She's grinning with he eyes locked on mine.

The normal menu has been replaced with two pages of pictures of Leah and Alex from last night. It seems they had someone take some pictures of them last night before they left. Much of it is reminiscent of what I remember seeing. Her ass pressed against his crotch, his hands gripping her hips. Him standing behind her, one hand on her tit, her hand has disappeared behind her, likely on his cock. Another is something new: They're on a armless chair, she's straddled him as they are a mere moment away from lips touching, Her dress is up over her hips, exposing her bare ass.

I quickly close the menu as I realize we're in public and I'm not doing a good job of hiding the images.

"Well, did you guys decide if you'll be having any dessert?"

"I think he's trying to decide if he wants any, Alex. Do you have any suggestions?"

"What the fuck?!" my mind screams and I recoil. I look up and see the waiter apparently for the first time. He's not revealing anything, he just calmly stares at me, waiting for my answer.

I remember our conversation on the way here. I take a breath.

"Well, I think it all looks fine. I probably won't have any though, so it's really up to my lovely wife here."

Leah responds on queue, "I think we'll take some, but not now. I'll let you know when."

"Excellent miss. I'll be back with your check." He leaves to give us a moment.

"When did you plan this?" I ask still in shock.

"Last night, as we were dancing. I told him pretty quickly that I was married and we were just roleplaying. He said he'd help make things interesting, but when you didn't interrupt, we came up with another plan. First, I went to the bar to talk to you. To give you the chance to stop things. You declined. Pointing at him and you leaving was the confirmation we needed to keep going. Next, you chose to leave without me...without even questioning or putting up a fight. You knew I would be with this man that was all over my body, and clearly wanted to fuck me. Finally, you willingly left the bedroom and left me to send lewd pictures to a man I just met and masturbate to his images. All of this while you're in the next room. All of this was by your consent by lack of action."

"I know."

Leah is in action mode. When she has a plan she activates it and pushes it through faster than most people can react. She doesn't sound upset, disgusted, or bothered. She told the tale as a matter-of-fact.

"Here's you check sir. Let me know when you're ready to pay up."

The wording seems off. If I wasn't imagining my wife on this guys dick; if I wasn't imagining her screaming his name as she cums on his cock, I wouldn't think anything was strange.

We're pretty quiet the rest of the evening and all the way home. When we get in I sit on the couch and hang my head. Why am I allowing this and whining about it at the same time? All I have to do is tell her not to go through with this and we go back to being normal.

Leah comes and lifts my head. She smiles and then straddles me in the same way as the picture of her and Alex.

"Kiss me." she commands.

I do as I'm told, and as I do I forget about everything else. Our lips embrace and our tongues mingle. My hands instinctively grab her ass and start to massage each side. My fingers probe her ass as she grinds on my caged cock, again I realize she's not wearing anything underneath. My breathing quickens as hers does. I can feel my cock start to leak cum as her ass grinds my balls. She goes faster, knowing that she can make me cum like this.

Harder. Faster.

She pulls back from our locked lips and looks at me. Biting her lip and eye fucking me as she starts to add a bounce into the grinding.

Harder. Faster.

We're sweating. I lose my grip on her ass as I start have a strained orgasm. A little spurt and I'm done. I'll be leaking the rest out over the next hour.

As I lean back on the couch and catch my breath. Leah stands up on the couch.

"Now it's time for your dessert. You've been such a good boy. Sit back and enjoy."

She straddles my face. At first she just stands there, her lips just over my nose. I can smell her. I see her glistening, I can tell she's enjoying herself. This realization gives me a second wind and I strain my neck.

"No, not yet my wannabe-cuck. Be patient."

She moves her fingers down and starts to finger herself. I'm an inch away and trying to get something to taste. She quickens her pace and she starts to shake. It's never been this quick for her and I know the reason. She's imagining being fucked by a stranger, by Alex.

"Ooooooohhhhhhhhhffffuuuuucccckkkkkk mmeeeeeee" she screams out. As she cums she removes her fingers and slams her wet pussy into my face. I'm suffocating in her orgasm. I try to lick her but she's too close and she starts grinding again. I've become a toy for her. I'm just existing as she smears herself all over my face.

As fast as it started, it ends. She rolls to the side and sticks her fingers in front of my face.

"Here, clean this up for me."

I do as I'm told. I'm doing that a lot lately whether I mean to or not. Was this all my idea? Or was I lead to this?

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10 Days until 'The Day'

I'm clothes shopping today. Every day there's something on my list of things to do to prepare Leah, and myself, for her date.

So far this week I've picked out purchased a dress, shoes, necklace, and some perfume.

Today I'm looking for lingerie.

She won't be wearing this under her clothes, so that opens some options.

We made a plan for 'The Day' to help guide my purchases. I'll drop her off at the same bar we went to last Sunday and then I'll stay close until she calls for me to pick her up. I'll have her lingerie in the car where she'll change. I'll then drive to Alex's house and drop her off and go home. She'll then call a rideshare to bring her home.

So...what would he like? Should it be something to remove or something to wear the whole time? Does he like frills? lace? feathers? leather?

I'm over thinking it. This is the first time, I want him to unwrap her like a present. I need layers and nothing too confusing to put on. I settle for a two piece lace set with a black silk robe to go over.

My imagination is racing. I reach down to stroke but it's like a phantom boner, I think it's there but when I go to grab there's nothing.

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3 Days until 'The Day

I've cleaned the house what feels like a dozen time. I've given two massages, four foot rubs, seven assisted orgasms, and waxed Leah's legs.

Today is a light day of waxing Leah's pubic hair. Neither of us have a preference for hair down there, just as long as it's maintained. She only does this when she's dating, and it's been a long time since then.

I'm anxious again. Keeping busy is the only thing that's kept my sanity over the last ten days. I decide to draw Leah a bath. A bath bomb, candles, wine. Make sure it's perfect.

I guide her to it and undress her with all of the intention and sanctity of a ritual. It might as well be, I am preparing an offering of the utmost value. My life is will forever be changed regardless of the outcome. I need it to go perfect.

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One day until 'The Day'

Of all the things, this will be one of the two more humiliating ones, though they're both related. While Alex is out at work today, I'm tasked with going to his house and cleaning it. Along with cleaning it I'm to bring and setup any toys my wife has asked for.

Where did Leah find his guy? Why would someone she's known less than a month be so willing to let a stranger in his house? What have they been talking about? I've been sleeping in the guess room all week. Not out of punishment, but because I haven't been able to sleep due anxiety.

"I can still stop it" I tell myself.

I don't. I rub my cage almost constantly in anticipation instead.

Tomorrow will be worse. Leah decided that since I was cleaning his house today, tomorrow I should stop by after dropping her off and set the mood. This mostly means ensuring there's chilled wine, her 'sexy jams' playlist available and on call, vibrator at the ready, and roses to and on the bed.

She always wanted a romantic date, maybe I should've done it for us rather than them.

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'The Day'

Much of the day is standard fair. We wake up, have breakfast, go grocery shopping, go to the gym. Nothing out of the ordinary.

Things start to get real around 4 pm.

"I'm taking a shower, please make sure my clothes are all ready."

I take pause. Every step is getting closer to my wife with someone else's dick inside her. I take a deep breath.

"I'm on it. Do you need anything else right now?"

"Nope! I'll be getting ready. I'll be ready by 5:30."

It's always 5:30. She likes punctuality and consistency.

I do as I'm told. I pack her a small bag that will hold her change of clothes and load it into the car. I make sure to charge and load up my laptop. I'll need to write during the night so that my mind stays distracted.

She steps into the living room and my jaw drops. She turns around and it hits the floor. She's in a black backless cocktail dress with a split thigh. Her hair is up again in all of it's short curly glory. Her heels are a modest 2 inch with a thin ankle strap.

Her necklace is a simple thin braided silver chain with a key that hangs at the top of her cleavage. I get up to kiss her but she stops me.

"Tonight is not about you. Remember that. Now, let's go, my date will be waiting."

Leah sits in the backseat and immediately goes to her phone.

"When you're ready." She says dismissively.

If there was ever any confusion of what my role was, that illusion would've been broken.

45 minutes of silence other than music and the occasional giggle from the backseat. I realize we never got around to setting rules. Will they use condoms? I know we talked about me cleaning her up afterwards, but there was never a discussion on if we verified if he was clean. Leah is on birth control, so that's not a concern at least.

Should I be privy to their conversations? It seems like this was all rushed. I get the feeling again that I've been setup somehow.

"His tests came back clean. So he'll be cumming in me. Whether there will be any by the time I get back to you is another question. Maybe you should stay near his house later. I'll think about it."

I don't think about her dripping with another man's cum, or that cum being in my mouth, instead I hope she can't read my mind. She has the oddest senses.

I pull up to the front of the bar and put it in park. Expecting some last bit of encouragement, or another affirmation that I want this. I get neither.

"Come open my door for me and help me out. I don't want to flash anyone." She let's a little giggle out after the last part.

I do as I'm told. As I'm helping her out I see Alex walking up.

"Thank you, husband dearest." She says, making sure anyone nearby can hear, and gives me quick kiss on the lips.

Alex steps adjacent to Leah and puts is arm around on her back and quickly down and gives her ass a squeeze.

"Hot damn Leah, you look like a sex pot!"

I'm sure my face is red with embarrassment with the public acknowledgement that my wife just had her ass grabbed by someone not me.

"Hey man, I'll take good care of her tonight. We'll see you later when you pick her up."

Without saying anything else, he escorts her in; I get in the car and head to Alex's house to set everything up.

Getting to his house and setting things up only take about an hour in total. I try to write, but nothing comes out. I lay down on his couch and turn the Tv on to pass the time. After a while I start to get antsy and check my phone.

4 message from Leah.

"I took the lingerie bag.I'll just change here rather than in the car or at his house. We're going to get frisky in the car and I want to make things a little easier ;)"

"I forgot to get the jacket, good thing I have a short robe anyway!"

"Hey, I decided that you should simply stay at Alex's house. We ordered a luxury car to bring is there, eta 22 minutes."