My life long penetration fantasy

Dear Rebecca,

I have a life long fantasy of being penetrated by a woman with a strap on. I have used anal toys on myself, but never had the pleasure of being entered by someone else. My girlfriend and I have only been going out for 3 months and I’d really like to bring it up, but I’m afraid it might scare her off. I’m also not sure what I’d do if she weren’t up for it. I’d definitely be disappointed. How long into the relationship should I wait to tell her and how do I go about it?



Hi Sam,

Thank you for your email. When you tell your girlfriend about your life long fantasy depends a bit on how important it is to you to actually experience it in real life. If it’s a fantasy that you’re happy to keep just as a fantasy, then you can tell her whenever the time feels right to you. If it’s something that you definitely want to experience, and would be a deal breaker if she wasn’t up for it, then I’d recommend telling her sooner rather than later. The longer you’re together, the harder it would be to tell her and then find out she’s not interested. You would then be in the position of having to choose between her and potentially never fulfilling your fantasy, or moving on in the hopes of getting your dreams met.

As for how to tell her, how about start a conversation about fantasies. Ask her about hers first. If you don’t feel comfortable telling her your penetration fantasy to start with, perhaps tell her a different one first. As the conversation deepens and you both reveal a bit more of yourselves, you will feel safer to tell her your long-term fantasy. She may think it’s totally hot and want to explore it with you or not be into it at all. That’s ok. What’s most important is that you are open and honest with her and allow her to have her own opinion. If she’s not up for it, maybe you could find a compromise that would work for both of you.

Wishing you the best of luck.

With love,


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