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Watching for the First Time
#1

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You’re going to be excited, nervous, and a little anxious the first time. You’ve fantasized about it. She’s come home from being with him and told you about it. You’ve never actually watched her with someone else though.
The first big moment will be when she turns her attention to him. That will necessitate turning her attention away from you. If you’re going to feel an overwhelming sense of jealousy, that’s when it will happen. It’s important that you maintain control of your emotions here. You’ll ruin everything if you freak out.
Instead, enjoy this. Think about how badly you want this. Think about how often you’ve fantasized about seeing your wife’s mouth around another man’s cock. Think about how arousing it is to know that she’s making someone else moan. Even if she’s not looking at you when she’s doing it, you need to sit back and enjoy it. There’s more fun to come.
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When you watch him slide his cock into your wife for the first time you’re probably going to feel a mixture of emotions. You might feel jealous. You’re definitely going to feel aroused. You might feel anxious.
One of the things some cuckolds struggle with is confronting a version of their fantasy where they don’t have control. When you’re masturbating and dreaming about her cuckolding you, you control every detail. When it’s happening in real time, two other people are involved and you probably don’t control anything.
Your job is to enjoy what’s happening. It’s to watch someone else fuck your wife, and hopefully to watch him offer her the kind of orgasm she badly craves, and the kind that you likely don’t provide her.
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Watching your wife have sex with someone else should be arousing above everything else. Once you’ve moved past the initial mental hurdles you should be able to simply relax and enjoy the absurdly arousing show they’re putting on for you.
Should you masturbate? You should definitely decide beforehand if you’re going to be permitted to masturbate. It really depends on the couple. You should absolutely not orgasm, though. The moment you climax, every bit of lust you’re feeling will disappear. Since it’s your first time, there’s a very good chance you’ll just be left with the feelings of jealousy and anxiety that are there.
That means there’s a good chance things get ugly. Maybe you demand he stop fucking your wife and leave. Maybe you leave the room in a jealous rage. Maybe you have a huge fight with your wife afterwards. These are all bad things that will likely ensure that your cuckolding fantasy comes to an end and could lead to much bigger problems in your marriage.
Feel free to masturbate and revel in the pleasure of her getting fucked by someone else. Just don’t cum. It could ruin everything. If you end up losing control (not a good thing, but it happens) and cumming, just leave the room. Let your wife and her lover finish what they’re doing and try not to think about it. Becoming an asshole after you orgasm is the quickest way to ensure that she has no interest in cuckolding you anymore (or, in the worst case, that she decides she doesn’t even want to be married to you anymore).
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I’d recommend you keep your dick in your pants for the first time. It’s a smart way to prove that you’re thinking about her above everything else. You can rub your dick through your pants and generate that beautiful arousal, but keep it hidden and concentrate on her.
If she’s interested, kiss your wife as she fucks her lover. Suck on her nipples. Caress her. Connect with her. That may not be what she wants - she might just want to concentrate on the man she’s fucking - but if she’s interested, go ahead and indulge her.
Remember that you’re going to get a chance to orgasm. It might come later after he’s left, but your climax is an important part of cuckolding. It can be smart to work out beforehand when you’re going to orgasm. That way you don’t end up denied. Your wife gets to enjoy her lover and his big cock and at some point you get to enjoy the orgasm you crave.
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Remember everything you see. It will be beautiful fantasy fuel for weeks and months to come. Remember what it looked like when he slipped into her from behind and fucked her as she stared into your eyes. Remember how loud she moaned for him. Remember how she moaned into your mouth when you kissed her as they fucked.
Even remember the moments that might have made you uncomfortable. Remember when they had missionary sex and she completely ignored you as he fucked her to her first orgasm. Remember how they kissed with such eagerness and passion. Try your best to clear your mind of the distracting bullshit (anxiety, jealousy, fleeting anger) and concentrate on the fact that your fantasy is coming true, even if it’s not exactly as you imagined it.
Quick note on that: There’s almost no way the first time is going to play out exactly as you imagined it. That rarely happens because it’s going from one person dreaming something in his head (that’s you) to three people participating in a real life sexual trio. It’s also important to remember that the first time isn’t necessarily a reflection of how every time will go. If there was something you didn’t like, tell your wife about it and it can change for the second time.
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If your wife is willing to let you go down on her after she’s been with her lover, this is a great time to cum. Some women won’t be up for this (they may warm up to it in subsequent play sessions, though). If she is, pull out your dick and get to stroking while you go down on her.
Bring yourself to a climax as you taste the mixed juices of her and her lover. Cum while you think about the sight of his cock filling her pussy, the way she moaned for him, and the orgasms he gave her. Doing so will deepen your cuckoldry and associate your sexual pleasure with your wife fucking other men. It’s a perfect way to end your first watching session.
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#2
As a guy who has been wrestling his wife on a regular basis for a number of years now, make sure it is alwasys fun for her, not just you. Make little sidebets, who does the dishes etc, that adds a bit to it
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