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Hookup Help: Cuckold Relationship Tips

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Q: Dear Jenny. I’ve been in a long-term relationship for a while. Although I still love having sex with my partner, I fantasize about watching her with another man and only recently discovered the word cuckold to describe this “fetish”. This started when I stumbled across some cuckold porn. I’m not sure how to bring this up to my girlfriend and pray that she doesn’t get angry and/or turn me down. Do you think many women are into this or is it merely a fantasy? Any tips on making it happen would be great. -Derek

A: Hi Derek. The cuckold relationship, fetish, or fantasy isn’t as rare as you may think and can often keep the relationship fresh, the sex interesting, and the libido raging. It definitely isn’t for everyone, but it sounds like you’re ready for that possibility. The best starting point is to be in a solid relationship with someone you trust and someone whose loyalty you don’t question because this “sex-on-the-side” is just that. This type of relationship is not to be confused with a multiple partner poly triangle. If you and your partner are a bit shaky, this isn’t the time to bring this fantasy up, as things can get stirred up with extras coming in.

Talking to your partner ahead of time about their limits, boundaries, and expectations will help you both prepare. You may be turned on just knowing your partner is having sex with others and only want to hear about the details, or you may want to watch. Maybe she wants to watch you. Do you want a regular third or is this a one-time exploration. How will you choose this other person?

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Despite discussing your desires and expectations ahead of time, you also want to keep the focus on fun. This experimentation should not be about betrayal or punishment but sexual exploration with your lover. Both partners should feel safe and secure with the partner they choose, whether it’s someone they know or someone they’ve met online. Some sites like AffairLink.com promote swinging and threesomes that make it easier to find a willing person to fulfill your cuckold fantasy. And of course, be sexually safe!

For more information: 10 Beginners’ Tips for Cuckolding

We’d love to hear from readers who have experience with cuckold relationships. Leave a comment!

Hookup Help is a Q & A series. If you want advice or a female’s perspective on hooking up, online dating, relationships, or sex… we want to hear from you. SUBMIT YOUR QUESTION HERE, and who knows, you may appear in the next Hookupland newsletter. -xo Jenny

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