How To Prepare For Your First Cuckolding Adventure
I was sent a message yesterday—a beautiful message—with an announcement that I’m sure all y'all reading this will love as much as me. I’ll keep her name/account anonymous, as always. Here’s what she wrote:
Good evening! I told my husband that I’m ready to try this for real. Not sure what the next step should be. We are in our 40s and aren’t exactly the bar-hopping social types. Plus we met and dated before Internet dating apps were a thing. So any advice you have for us from how to find someone to how to prepare ourselves mentally and emotionally for the experience would be welcomed. Thank you!
I told you it was a beautiful message!
I know this much, after writing back and forth a few times over the past year or two… She and her husband have been walking along the edge of the cuckolding pool for a few years, sharing fantasies and commenting back and forth via Tumblr, waiting until the water was just right to dip their toes in.
Well… It’s cannonball time!!
Imagine the excitement her husband felt hearing that she was finally ready… I bet he’s jerked off a thousand times since hearing the news!! And that’s what I love the most about cuckolding, especially a first-time event… Everyone is fulfilling a fantasy. It’s the ultimate Win-Win. And even better than the fulfillment of fantasies, they’re creating an event that will last forever.
Even if their first time is a one-off event, they can relive it forever—every smile and kiss, the fresh taste of a new man, the desperate sounds of her need bursting through her married lips, and the orgasms… Oh, so many orgasms.
I get countless men asking me how to turn their wives into… well, into someone like me. So I get an extra charge when it’s the wife asking about this. That means it’s really going to happen for both of them. I know it’s just a matter of time before they have their first adventure. So, if I can give them a little advice and added confidence while preparing them for the impending mental tornado that’s about to rip through them (in the best of ways), then taking the time to write all of this will have been well worth it.
A first-time cuckolding event hits hard. The closer or more in love with your partner you are, the harder it hits. If the guy isn’t prepared, then it can knock him out. Almost all of them come back from it, though, begging for more once they realize that NOTHING will ever come close to how that pleasure-soaked dagger made them feel.
You will come to crave it just as she craves him. You’ll both need more.
But that first adventure must be a positive one. So rather than go back and forth with a few lines of advice and encouragement, I wanted to write a full guide and share it with everyone, hoping to help even more couples prepare for their first adventure—and to ensure it will be the first of many.
The advice I’m about to give will be targeted toward married or long-term couples who’ve already agreed to have their first adventure—no more trying to talk one or the other into it. It’s happening, so let’s get to it…
Part I: Develop A Plan For Your First Adventure
I’ve found that the longer a couple has been together (especially those who’ve been monogamous), the more apt they are to develop a plan. As someone who waited a couple years before acting on my own desire to do this, I know what it’s like—and I was a teenager!
Spontaneity will come with time. I’m not here to talk about the evolution of a cuckolding couple, but that will definitely be a part of it.
I talked to some of you, reading this now on Patreon, long before deciding to cuckold my boyfriend for the first time. Well, at least long before admitting to myself that it was inevitable. Once we let ourselves go down this path, it’s almost impossible to jump off. The need is there, growing and feeding on every image or video of great sex that you see and hot guy that you meet. It strikes you HARD when you’re masturbating and even harder when having sex with your boyfriend or husband, calling to you… There’s something greater out there, just waiting for you… You deserve this… It’s time.
Once I knew it was my time, I developed a plan to talk my boyfriend into it. Since this guide is for couples who are already there, I’ll move on to the first bit of planning.
Part II: Emotional Understanding
I’ll start by advising you this: Your first adventure should be with a stranger.
Sharing someone you both know adds a wrinkle you don’t need for your first adventure. There should be no feelings or history between you and the man you choose. Remember, these are my opinions and some of you might feel the other way on this, but I’m mostly looking out for my women out there. You see, the men (for the most part) are all-in. They want to live out a hot sexual fantasy and let everything fall where it may. I can hear their thoughts right now:
What woman wouldn’t want to have sex with someone new? I’m telling her I’m cool with it, and that he can have a bigger dick than me… Doesn’t she love orgasms? I know she does!! What’s there to think about? We’ll deal with the emotional fallout after it’s over. I’ll be fine either way. At least I’ll have something hot to jerk off about for the rest of my life!! I’m ready. You ready? —- Then, when she finally agrees, he’s like: Woo Hoo!! Now, let’s find you the biggest cock this side of the Mississippi… or two.. or three… how many do you think you could handle? You must want at least five, right?!??
I’m only just slightly joking here. lol - But you get my point. A woman can get overwhelmed with the “push”. She’s going to wonder what she could possibly do to satisfy YOU and be enough. Yes, she’s thinking about you. She wants to make sure you’re really going to be okay with what she’s about to do. Guess what… You’re right to think she wants someone with a bigger dick. Of course she loves orgasms. Yes, she knows this will be one of the hottest things she’ll ever get to do. BUT she’s also more of a pragmatist. She knows that tomorrow will eventually come and your cute little cock won’t be stealing all the blood from that male brain of yours. She knows you may be all about it until it happens.
She wants to protect you… As confident and determined as you are about what you want, she’ll never believe you. Sorry guys, but you’ll have to earn that trust from her. That won’t be earned in bed with fantasy talk. The truth is, you won’t be able to earn it until AFTER the first adventure ends. She is going into this thing blind, and she’s counting on you to support her.
Let me add one quick thing about creating “rules” for your adventure like “no kissing”: DO NOT SET RULES. They will only be broken. If a guy can put his cock inside you, then he should be allowed to do the same with his tongue.
As for condoms and safe sex… that’s worth a discussion. Personally, I love nothing more than feeling the real thing inside me… the heat of him… and don’t get me started on the gush of hot cum. Mmmmmm
Part III: Choosing The Right Man
Rule #1: WHAT YOUR GODDESS WANTS, YOUR GODDESS GETS!
You want her to experience the best things in life and be happy on this day and every day going forward, yes? Then you need to go with her flow. You can suggest anything you want, but let her be the final decision maker. Then, once she’s made that decision, you need to support it. This is crucial for turning this into a long-term thing.
Since she gets to choose the man, she also gets to choose how and where it happens. Most married or long-term couples prefer doing this on a vacation where the other guy couldn’t possibly pop back into their lives. However, this (practically) eliminates the ability to see him again if he was amazing. So I’d ask the woman what she wants. Would she rather have it be a guaranteed one-off adventure for the first time? If so, plan a vacation. If you’re thinking of having a somewhat local experience, then it can even be an hour or two drive away—someone you won’t run into at the grocery store or at church. Then, even though he’s “far” away, he’s close enough to do it again.
Why would I recommend that as a possibility to consider? Because of Aaron, my first. I’ve gone back to him so many times I’ve lost count. I can’t imagine a world where I only got to have him that once. That being said, I can totally understand the vacation one-off plan too.
Whether you’re at home or on vacation, that means you’ll have to choose between a real-life meeting or an internet setup. Which do I recommend? It totally depends on what makes the woman more comfortable. Personally, I’ve done both—lots and lots of both. I prefer a live meet for a lot of reasons, mostly because of the vibe factor. How a man moves, talks, breathes and smells (pheromones?) all have an effect on me. Nothing hits me harder than his eyes, though—the way he makes me feel when he looks at me. You don’t get that over the internet.
On vacation, however, there’s a lot of bonuses to an internet meeting via a hookup app like Tinder. You’re nearly guaranteed to find someone local and you can do a hit or miss strategy over however many nights you’re away. Even the idea of going on the meet will be a massive turn on for you both. Whether things work out with the guy or not, you’ll be dressed up and the very idea you were ready to bring someone home that night will lead to crazy hot sex! So line one up for a festive-style bar meeting each night. You could even do two per night at different locations if the first one doesn’t work out. Meeting and chatting are easy, but here are some points of interest:
Don’t be shy about asking him questions. If how “big” they are doesn’t matter to you then don’t ask. If it matters, then you NEED to ask and go ahead and get a picture or ten as well. We each have certain things we want in a man and it’s up to you to check those boxes ahead of time so you’re not disappointed later. Pictures are a must, obviously, and don’t be shy about asking for specifics. Make sure you tell him you’re married (or with a long-term boyfriend) and what his role in all this will be.
If you plan on doing a real-life meeting then you have to decide how involved you want your husband/man to be. Should he wait at the other end of the bar? Should he wait in the hotel room and text with you throughout the night? When do you tell hot stranger guy that you have a guy back at your place who wants to watch? That last one, I can help you with. You have to tell the guy at some point, right? I find it best to lead with it. Yup… Guys love it—especially Alpha types, which is who we want to find. We want a guy who’ll have no problem fucking us in front of the love of our lives, and who makes a show out of it. Go ahead, teach that boy how I like it. Show him what an orgasm is supposed to look like.
Leave the wedding ring on and lay it all out there. It’s a turn ON not off. Same thing online - don’t hide your situation. Lead with it.
As with most things in life: be fearless and you’ll be rewarded. If you see someone who interests you, throw them those eyes… Spark a conversation. Life is waiting for you out there, but sometimes you have to take it. Let him know what you’re looking for early on. Sometimes the more a guy talks, the less I want him. That’s not even his fault, I’m just a fickle bitch. The quicker you can ask him to take you back to your room, the better it will be for both of you. Don’t be shy. You’re a Hot Wife in the making, so act like it!
Part IV: Supporting Her - Before Your First Adventure
This is where my boyfriend SHINES. His actions and words put me into Goddess mode before my “dates” where I quickly sink into submissive whore mode for that other man. But, when all is said and done, his loving eyes and knowing tongue have me feeling like a beautiful Princess—even as I lay there shaking and sweating—a hyper-orgasmic, cum-filled mess.
It’s in these moments where we’ve bonded closer than ever. I know it sounds crazy, but it’s true. Walking on a beach holding hands is nice, but having the man who loves you dress you up for a date with someone else is next level. Hearing how beautiful you look before he sends you off into their arms is something I can hardly put to words.
If you plan on searching for a man via an online app then may I suggest you order him between your legs while you scroll and swipe… Every now and again flash him the screen and show him the men you like best. Grind those images into his head while he grinds his tongue into your pussy. Talk to him while you do it… “You like preparing me for other men, don’t you?” - “I bet this guy has a really big cock.” - and show him your matches. Read the things men say to you and what you return to them. It will become a regular thing between you both, trust me! Whether you plan on meeting more men or not… It’s a fun cuckolding exercise.
Men, keep your focus on her. I want to hear how beautiful I look, how lucky those men will be to have me, how yummy I taste, how wet I am for them, how I deserve whatever I want… During sex in the lead up to your first adventure—tell her all the things you want for her. If you want him to be bigger and fuck her harder… You want him to make her cum harder than you ever have… You want him to make her moan and scream and call out his name and forget that you’re even there… You want to see the pleasure in her eyes… the lust and need growing with every deep thrust until she begs for his cum.
Don’t be shy. Tell her what you want. Odds are, she wants all those things too!
On the day of your first adventure or first night out on the hunt, the preparation begins long before you walk out the door. Men, you’ll want to pamper her all day. Make your first date tactics look like a train-wreck. You should ALWAYS treat her this way, but on this day in particular, she has risen to a new level… Make her feel it.
Buy her something new to wear. Help pick out her bra and panties or lingerie to go under whatever dressing that other man will be removing later. Think classy/sexy on the outside while diving into your kink-zone for what’s under. Whatever makes her feel sexiest…
Help her get dressed and watch longingly as she applies her makeup. You’re her servant for the day. Her pet.
Women… Tell him what you want when you want it. The more you take control on this day, the more he’ll love it. Be the Goddess he sees in you. Make him pull up your stockings and affix your heels. Put him on his knees whenever possible. Make a comment about your lip gloss/stick when applying it… If you’re excited, tell him. If you’re wet, tell him. If you want him to give you a quick lick before pulling those panties up, order him to do it.
It’s up to you what he does during your meeting. Do you want him to go with you or wait? If he’s to wait, you should tell him not to jerk off and if you have a cage then lock him up. You want him to be PEAK turned on when you arrive home with another man. Point is, whatever you want him to do, then tell him.
Part V: Supporting Her - During Your First Adventure
She may want to experience her first time (cuckolding you) on her own, without you watching. If so, there are a few things you’ll want to do to enhance that for the both of you. Text him throughout. Have a couple pictures taken (especially one before and another after).
If you’re up for it, give him a call and put the phone down so he can listen. When you return, order him between your legs and tell him everything that happened while he cleans you up and makes you cum.
If the plan is for the husband/boyfriend to be there then have some idea to what his role will be. If not, it could get uncomfortable. Will it start as a threesome and turn into a watching session? Will he be relegated to a chair in the corner? Will you hold hands and keep him close? Do you want him dressed or naked or with just his cock hanging out so you can play with it or suck him from time to time? There are no right or wrong answers, but you should have an idea of what you want before it happens.
If you want my suggestion, I’d say to start with him watching. That’s easiest for you to get into things with your “guest”. Pretend he’s not there as you start your foreplay, then start by flashing him your eyes… smile at him and let him see the lust on your face… Wait until your guest is fully hard before involving your husband/boyfriend. If you want to talk to him, tell him how good something feels and ask if he likes watching your mouth wrapped around a big cock. Emphasize how big the other man is (if he’s bigger) and how amazing his tongue feels… He wants you to love every second of it. Every word you say will be etched in his mind forever, so go for it. I turn myself on even more when I’m talking to Mark. I love watching him squirm. lol
Men, as the night goes on, be ready to do as ordered. If she wants you to hold her hand or kiss her lips (even if she’s just sucked his cock), then you do it… and do it passionately. It’s okay to let your sub side shine. The more a submissive helpful pet you are to her, the more she’ll enjoy the contrast of the powerful man pumping orgasms through her soul. You should both embrace those roles—feed off that dynamic.
Part VI: Supporting Her - After Your First Adventure
Men… The most important thing you can do for her after a watch session is to make her feel like a beloved Princess. While she’s laying in the post-sex mess of sweat, drool and cum… Laying there a well-used, listless, leaking vessel on the verge of passing out… You need to kiss and love on her like never before. Show her how much you love her and enjoyed the incredible show she just put on for you. Connect through your eyes and every kiss across her body, the one she just gave to another man. Breathe in their shared essence while lapping up every drop. If he did his job correctly, then it will be everywhere, so take your time.
Don’t ask a million questions. There’s all the time in the world for that. In those moments right after, even when that other man is getting dressed or walking out the door… You will treat her like a fallen angel right after that stranger just used her like a filthy whore—and she, like you, will have loved every last second of it.
Prove that her pleasure IS your pleasure. Her ascension to Goddess is complete. However supportive or submissive or helpful you’ve been up to this point in time to this love of your life… You’re going to go further from this day forward.
No matter how good that other man just made her feel… No matter how many times he made her orgasm or came inside her body—there is nothing he could ever do to make her feel as loved or as powerful as this. You’ll both feel it in those dripping wet moments after you’ve cleaned her up then kissed your way to her mouth for the ultimate kiss.
Because no kiss has ever tasted quite as sweet as a cuckolding kiss when I can taste so clearly another man’s hot cum on my boyfriend’s loving lips and he looks me in the eye to tell me how much he loves me. When you hear those words for yourself, you’ll be thinking, You better… Because we’re doing this again!!
If you want to read the rest of my articles, including over three years worth of my own adventures, please check me out on Patreon: https://www.patreon.com/queenjennyxoxo
Either way, please share this - you never know who it might help! XoXo
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