"After five years of being apart, I'm now re-dating my high school sweetheart whom I love. We lost our virginities to each other, and even during those five years we continued to have sex every now and then when we were single and managed to see each other. (We went to colleges in different cities.)
Now that we are together again, we've decided to wait a while before we have sex, but that does not mean that I don't find him attractive or that I don't sometimes just want to rip off his clothes. The problem is that one of the last times we had sex (about a year before we officially reconnected), I felt like a prostitute. I don't exactly know why, I just felt used afterwards and it was not enjoyable to me at all. I think part of the reason I say 'prostitute' is because he kept making me change positions and just seemed really into it for himself. I love him and I know that he loves me, but I think I'm having trouble getting over that experience. Even now, he will ask me to dress up for him so he can masturbate, which, as his girlfriend, I would normally be happy to do, but I just get that 'used' feeling again. I feel like a piece of meat, or just an object.
Of course he senses my change in happiness and it ruins the mood. I don't know exactly why I started feeling this way and I don't know how to get over it. I'm so afraid that once we start having sex, I will continue to feel this way. What's wrong with me? Please help!"
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First thing: there is nothing wrong with you or how you’re feeling. Whatever is going on for him, whatever his intentions or motivations, there is absolutely nothing wrong with how you feel. There’s a big difference between having uncomfortable feelings and having something be wrong with you.
Second thing: trust how you feel about this. Something in this situation doesn’t feel right to you, and whether that’s about him, you, or the two of you together, your feelings are there to tell you something important. Unfortunately, they don’t always give you a lot of useful information, but they are valuable for making sure that you know that something is going on. In my experience, the best thing to do is listen to that and try to figure out what those feelings are trying to tell you.
It sounds like you have some unresolved feelings from that first experience of feeling like he was using you. When old feelings linger, they can affect how we feel about present-day experiences. Sometimes, that’s because the current situation is a lot like the past one, and at other times, it’s because we project those emotions onto the present even when the circumstances are very different. Either way, the best approach is to create space to talk about them and figure out what you need. I strongly suggest having that conversation with him when you’re not in the middle of the emotion because that makes it easier to talk about what’s going on without getting lost in the feelings.
Since you said that you’re not sure what it was that made that so uncomfortable for you, here are a few questions that might be worth exploring:
What was it about that first time that felt uncomfortable for you? When he was into changing positions so much, what about that made you feel used? Was it how he did it? Something he was saying? If he had said or done something differently, would that have made it better for you? The more you’re able to answer questions like these, the easier it’ll be to talk about your experiences.
Also, I’m not quite clear from how you phrased it, but when he asks you to dress up for him while he masturbates, do you do that? In my book, that counts as sex and I’m wondering how that fits into your mutual decision to hold off on sex. I can totally see how a request like that could trigger that “used” feeling if the two of you are supposed to be waiting. If it feels to you like he’s pushing your boundaries or trying to get you to do something beyond your comfort zone, one of the best things you can do is tell him that you don’t want to do that. If he persists, that’s a big warning sign to end things.
It would be really easy in this sort of situation to imagine all sorts of reasons why he’s acting like this. And while any of those guesses might be accurate to some degree, I want to caution you to try to not jump to conclusions. For example, some possible things that might be prompting him to act like this could be:
Maybe he’s gotten interested in experimenting different ways of having sex and doesn’t know how to start the conversation with you about it, so he’s just going for it. Maybe he’s gotten into porn and is trying to act out what he’s seen on the screen. Maybe he wants to explore some fantasies, his or yours, and hopes that you’ll reciprocate with your ideas. Maybe he’s clueless about how these situations feel to you and thinks that you’re enjoying it as much as he does, at least until it’s obvious that you don’t. Maybe he’s being selfish about your sexual interactions. Maybe he’s hoping that you’ll speak up with ideas of things to do.
Of course, there’s no way to be sure what actually is going on for him unless you ask (and he’s willing to tell you). The longer these things build up, the bigger they get. So as challenging as it may seem to talk about it with him, it’ll be a lot easier if you do it sooner rather than waiting. Take some time to tell him how you’ve been feeling. Find out what his intentions were. Trust your feelings and keep your boundaries solid.
I know that’s all pretty vague and I wish I could give you some more concrete suggestions. But there are too many possibilities for me to be able to steer you more than that. This sounds like a really hard time for you and whatever you decide to do and however things work out, I hope you find the support that you deserve.
And no matter how you feel, there is nothing wrong with you.