Hope This Helps - First Encounters

Every so often, The Book of Bartholomew offers up an advice column by Topping and Charlotte. These columns, called Hope This Helps, are available by clicking on highlighted text in the stories. As the healthiest young couple in the book, they are willing to share their wisdom on relationships: familial, platonic and romantic.  This week's story has Charlotte and Topping advising a fan on making new intimate encounters less difficult. 

Dear HTH,

I feel like such an idiot. The other night I had my first intimate encounter with my new boyfriend. I had made out with a couple of guys before and even went all the way once with a guy, but that was a weird and unusual situation. Anyway, my new boyfriend, I'll call him Zigfried, came over to my apartment for dinner. Afterward we both were anticipating that something would happen and were a little awkward and nervous. Finally, Zigfried hugged me and started kissing me. It felt great. We moved to the sofa and started really kissing. I really liked what we were doing but was a little unsure of what I wanted or what to do. Then Zigfried started feeling all over me with his hands. At one point, he reached between my legs and rubbed my crotch. I don't think I was quite ready for that just yet, but it was okay for the moment. I really liked kissing him and was feeling like I wanted just to do that and hug and roll around for awhile. Then Zigfried started unbuttoning my blouse. I just wasn't ready for that yet. I don't know, maybe ten minutes later that would have been fine, but just then I wasn't ready for that. I stopped the session by pulling away some. I suggested it was getting late and that he should go home. He left. He seemed a little mad or frustrated. I just wish I knew how to get intimate with someone without all that nervousness and uncertainty. Are there steps to take to make first encounters less difficult?

Not a Prude But Feeling Like One
West Saint Paul

Dear Not a Prude,

Charlotte: Thanks for sharing a very personal and detailed story. I think this is something most people are left to figure out for themselves and it can be very... intimidating. 

Topping: As a guy I can tell you that we go through the same thing. It is hard to know what your girlfriend wants the first time; what's going to be too far, what's going to be too little. The last thing you want to do is step over a line that might end everything. Guys are always nervous about that. 

Charlotte: I know, too, that its not always clear going into the situation just how far you will go. You might think you just want to kiss a little, but then he ends up being a really good kisser and it makes you want more. It can be a changing situation. 

Topping: Its also hard for guys because women often let the guy take the lead. So a guy is in the position of always pushing the envelope to find out what the woman wants. Sometimes, until you do cross a line, you don't know what she wants. So we're in the position of pushing until we do something you don't like. 

Charlotte: Not a Prude, I don't know if we have a list of steps to take to make this weird moment of discovery any easier, but I think there is a need for clear communication in the moment. 

Topping: Wow, that's not easy. I mean, my head can be spinning when intimacy starts. Its hard to think about communicating clearly. 

Charlotte: But you do communicate clearly when we are intimate. 

Topping: I do? 

Charlotte: Yeah. If you're not liking something I'm doing you gently grab my hand and redirect me. Or you very softly reposition me. Wow, this is embarrassing! I've never talked about this stuff publicly before. 

Topping: I do remember the first time we started making out. I did unbutton your shirt,... well I don't know how much to share,... but when I went a step further you politely told me that you were happy to just do what we were doing, no more. I was happy with that, I liked being with you and what we were doing felt great. 

Charlotte: I think the important thing is to indicate your boundaries while communicating that you still want to be intimate with him and be close to him. If he's not willing to be patient, that's a different situation. But that first encounter with a guy you are interested in should be positive and end on a good note. 

Topping: I don't think any guy worth dating is going to complain if you don't go all the way the first time, but instead want to have a long relationship where you get to discover each other over time. 

Charlotte: Wow, nicely put. And there is something very sexy about knowing you will be getting together again and picking up where you left off. Something to be excited about until the next date.

Hope this helps!