Touch him outside his pants. Is he hard? Enjoy the way he feels in your hand. Tell him that you like it. Tell him you want him. Then go. Not rocket science. Don't turn it into drama. You are a grown up and it's sex.

Anonymous wrote:Cocktails. If he can't get it going, I would say something isn't right.

It's both of them. Not just the guy. The difference is that he is self-aware enough to not sprint ahead of his unease just so he can say that they did it.

Cocktails. If he can't get it going, I would say something isn't right.

Well at least one guy is going to get lucky tonight.....

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:If you both feel this awkward, it isn't time yet.

+1 Is this usually an issue for either of you? Why is it not happening organically?

OP here. I think it's just because this is the first time we've really seen us being in a real relationship again. Neither of us had trouble with the one night stands or someone you'll see for a couple weeks. I'm determined that this is happening tonight and we're planning just to have a quiet night at home. I just gotta get my mojo back again, haha.

Sounds like a confidence issue rather than comfort issue. My advice: forget about the expectations of a long term relationship with this person, and see it as just two grown people having fun in the moment. Tell yourself there is no chance of a relationship so you just want to get all you can from this moment.

Take that advice, and tell us tomorrow how many orgasms you had

Except they've been dating a while and have some form of a relationship.

OP, don't steamroll over whatever is holding you back.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:If you both feel this awkward, it isn't time yet.

+1 Is this usually an issue for either of you? Why is it not happening organically?

OP here. I think it's just because this is the first time we've really seen us being in a real relationship again. Neither of us had trouble with the one night stands or someone you'll see for a couple weeks. I'm determined that this is happening tonight and we're planning just to have a quiet night at home. I just gotta get my mojo back again, haha.

Sounds like a confidence issue rather than comfort issue. My advice: forget about the expectations of a long term relationship with this person, and see it as just two grown people having fun in the moment. Tell yourself there is no chance of a relationship so you just want to get all you can from this moment.

Take that advice, and tell us tomorrow how many orgasms you had

I'd say go have a few drinks and try to get your inhibitions down. It's normal to feel a little hesitant with a new person, especially if you guys are in some sort of virtuous cycle where each of your inhibitions is making the other person even more inhibited.

That's what cocktails were made for.

Good luck!

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:If you both feel this awkward, it isn't time yet.

+1 Is this usually an issue for either of you? Why is it not happening organically?

OP here. I think it's just because this is the first time we've really seen us being in a real relationship again. Neither of us had trouble with the one night stands or someone you'll see for a couple weeks. I'm determined that this is happening tonight and we're planning just to have a quiet night at home. I just gotta get my mojo back again, haha.

Sounds like an emotional intimacy issue and you are forcing it. That doesn't seem like it will end well.

Anonymous wrote:

Anonymous wrote:If you both feel this awkward, it isn't time yet.

+1 Is this usually an issue for either of you? Why is it not happening organically?

OP here. I think it's just because this is the first time we've really seen us being in a real relationship again. Neither of us had trouble with the one night stands or someone you'll see for a couple weeks. I'm determined that this is happening tonight and we're planning just to have a quiet night at home. I just gotta get my mojo back again, haha.

Anonymous wrote:If you both feel this awkward, it isn't time yet.

+1 Is this usually an issue for either of you? Why is it not happening organically?

Just unbutton his pants and pull it out.

99% of men would be more than ecstatic for you to initiate sex!

movie and wine at one of your places. you inititiate kissing and more touching, let him go to the next level. it should happen organically if there is a spark.

If you both feel this awkward, it isn't time yet.

I've been seeing someone for awhile and it's time. We both came out of long term relationships about a year ago. We have both slept with other people since those relationships. He is the first guy I have really felt any connection to and desire to have a real relationship with again. For some reason I can't seem to initiate the first time. We talked about it the other day and I know he's certainly up for it, but he's somewhat reserved and afraid of making me uncomfortable.

How would you go about getting the ball rolling?