This may be a silly question but after reading your response to ” how long should I wait” I felt more compelled to ask it.. My sexual history is somewhat colorful… I made a lot of very poor choices very early on, my very first boyfriend I only made wait a month, mostly because I was young and he was substantially older than me and I felt pressure, from that point on I continued to be frivolous with my body and never felt any real emotional connection to sex, I found it very impersonal actually… I never saw it as a very intimate act, it was something I did for fun… well I grew up… that all that ended a couple years ago, I’m now 29 and its been close to a year since I’ve had sex with anyone at all. This doesn’t bother me as I very rarely date, I’m taken a lot of time for myself. I recently started talking to a man… I’m very practical, I don’t believe in throwing all you have into someone right off the bat, I find that to be a recipe for disaster, so i try to remain reserved at first for the most part for my own protections, this may be flaw I’m honestly not sure. But he and I have spent time together about 6 times over the last two weeks, he did wait until the 6th time we spent time together to even kiss me, which I appreciate a great deal, I should also mention that we work together and have for a long period of time before ever beginning to see each other… now the first time he kissed me was slightly more hot in heavy than id have planned..it was like having one of those all out high school make out sessions and maybe its possible that my brain is trained to think this way…. but the entire time I was thinking… hes going to want this to go further, hes going to want to have sex… I’m not ready for that I don’t want to do that yet… in between kissing I finally just said ” i feel like I’m frustrating you” or “I don’t want you to get frustrated” i forget how I worded it… he told me he wasn’t frustrated at all and he wouldn’t have it any other way… you see here is my issue, because I’ve treated it so causally in the past I almost feel like I’m not entitled to change and want to wait… and I know you said in your previous answer to do other things like oral and hand jobs but I’m not really comfortable with that either…Id like to wait until there is a deep emotional connection, id like to experience that for the first time with someone I already had some pretty strong feelings for, to maybe try and experience the intimacy…but I’m no spring chicken I’m 29 and he is a few years older than me and I worry it will be found as childish or dumb, I’m not sure at all how to go about it, its very new territory for me, and I’ve spent so much time avoiding dating that I really don’t want mess this up, Id like to see it go somewhere.. I could use a little guidance, I apologize for the long question, I really hope to hear back from you.


I’m going to be honest here and say that your situation is very unique, however I do believe you’re on the right path to hopefully accomplishing what you’re looking for. I also want to thank you for reading one of my previous posts named “How long should a girl wait to have sex with her boyfriend?

With that said, I think it’s a good thing that even though you haven’t been dating for long you’ve at least known this guy for some time and enough to at least know what type of person he really is. I generally do not recommend dating people you work with and specially not if you value your job but I also believe in seeing things in a positive way when possible. I only say this to make a point that by working with him you can at least pay attention to some of his personality traits that could translate into this guy being a good catch. By this I mean, is this guy generally a responsible individual? Does he show up on time? What do other people think of him? Etc.

Back to your question, what you need to do is to continue to keep him interested in you until you’re ready to go all the way. And I know you mentioned that you’re not comfortable with oral or hand jobs but you can’t have it all here. You need to understand the point of view of the person you’re trying to attract and keep. If you’re truly interested in this relationship, you need to be realistic. Ask yourself, how long is this guy really willing to wait until he gives up? As you know, most relationships are about compromising and in your case you want to wait until YOU’RE comfortable with being intimate but at the same time you need to take his needs in consideration in order for both of you to be happy and be fair about it. I think communication is key but also some sacrifices might need to be made. And yes, I’m talking about letting him get at least to second and third base and not just leaving him at home plate until you’re ready to give up the home run.


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