Making a bold move

[CuriousDemo]

I know this guy and I suspected he was in to me but I wasn't quite sure. I sometimes find it really hard to tell if people aren't completely obvious. I am quite ditsy and can be quite shy in these situations.

When we were casually messaging he made it a little clearer by saying that he found me attractive. I completely didn't expect this so I was a little thrown back. This guy also appears to be a little shy so I am not sure what to do next.

I keep thinking about him and have arranged to meet him when my schedule clears up. It is usually a little awkward and tense when we are together so I was thinking about being really bold and suggesting to make things less awkward, we both take off our clothes (not underwear) to just make things are a little less tense and awkward. I know this seems like a crazy solution, but I honestly feel like this would make me less nervous.

I need to know whether this is a crazy idea...
How other people would react to this suggestion
Whether this is seen as completely sexually suggestive
This is something men would appreciate/not appreciate

 

[ElectricBlue]

Probably better to have a coffee in a nice little cafe somewhere first, go for a walk in the park, see a movie, have lunch together, talk to each other. You know, act like normal people. Getting your gear off is probably going to be... well, a bit awkward, first thing. I mean, where exactly do you envisage this happening, if all you've done so far is exchange a few messages?

 

[CuriousDemo]

We do know each other and we are familiar. Sorry if you got the impression we have just exchanged a few messages. We have visited each others apartments but it always seems so tense and I cannot pinpoint why.

I didn't imagine stripping in a business quarter in the city, but if we were comfortable at home. Who doesn't feel more comfortable when they are a little 'freer'.

But thanks for your more rational perspective.

 

[TheOlderGuy]

Just reach out to his face with your hand, and give him a kiss on the lips. The rest will fall in place naturally. It really IS in the kiss.

 

[Privates1stClass]

TheOlderGuy wrote:

Just reach out to his face with your hand, and give him a kiss on the lips. The rest will fall in place naturally. It really IS in the kiss.

When you kiss him and feel his erection against you, then you've gotten his attention. If the two of you are compatible, go for it. Life is too short to sit around and be shy. Good luck!

 

[voyboyEC72]

Tell him about your idea of each of you removing your outer garments. Once you're both comfortable with that, let nature take its course. If your panties are wet or if he has a pre-cum spot on his underpants, you'll both know that you're ready for full nudity. Do remember to touch him and allow him to touch you, even while you're both fully dressed.

 

[Darkrhytm]

Just ask?

 

[ReadyOne]

One of the best dates I ever had started with the girl saying, "Relax. You're getting laid tonight unless you really screw things up!".

I stopped worrying about how she was feeling about me and if I was doing the right thing at the right time. I just had fun and enjoyed being with her. Much later, she took me home and it was very easy to do the deed.

So give him reassurance every now and then (you don't have to promise what my date did) so he can concentrate on you, and not worry about the boy-girl stuff.

 

[CuriousDemo]

Really like this idea, although I am not sure I could be that bold. Probably would need a little Dutch courage.

 

[CuriousDemo]

You are so right. I think you have certainly given me ideas on how to be more open. He is really shy so I hope he does not freak out.

 

[CuriousDemo]

Honestly this is what I have envisioned but I am aware we are both shy and I am not sure how smooth an operator I am in the moment.

I am excited just by being daring to be honest.

 

[Privates1stClass]

Dear Curious,

Please let us know how it turned out.

 

[TarnishedPenny]

OK, somebody has to play the Devil's Advocate...

I am impressed with your daring and imagination, sincerely. But what happens if a) he says No or b) things don't work out once you two are down to your undies? I just get the feeling that it could be really, really awkward.

And, yes, taking off one's clothes (even if just outerwear) is almost certain to be sexually-suggestive. I think a lot of guys are going to find it confusing - What am I supposed to do next? A lot of them will instinctively take it as a go-ahead for sex right then. If you aren't ready for that, then what?

So I guess that it all hinges on where you want this to go and on what time-line.

If you want him in your bed that night, get a touch more bold. If you don't think you can work up the courage face-to-face, how about mailing him (yup, snail-mail) a note telling him how you feel and saying you want to bed him? You could make it a Good-For-One-Free-Night coupon or something, so either of you can pretend it was a joke if things get tense. I guess what I am trying to say is that it's easier to be bold when you don't have the other person there.

If you don't want to go that far (at least not right off the bat), you might want to take it easy at first. Tell him you're attracted (and I assure you that no man will take that badly), but you two stick to the normal getting-to-know-you routine like ElectricBlue66 and TheOlderGuy have suggested. If you think about it, there's a reason it's part of the normal human courting behavior pattern.

Good luck.

 

[NightL]

smoke a joint and watch a really bad movie together... everything will be chill after that

true

 

[CuriousDemo]

Well sometimes you just need a Devil's Advocate.

What you said completely makes sense and of course it has ran through my mind.

To be honest, I have been 'playing it safe' and leaving situations dissatisfied or wishing I had said or done somethings different.

I think I agree with your playing a game angle so I think I may have to whip out my post-its.

Your sensible outlook was most certainly appreciated, I am rethinking my 'bold move'.

 

[CuriousDemo]

Dear Curious,

Please let us know how it turned out.

I will let you know. The morning after I will be straight on the forum. Whichever way it goes, I will be honest

 

[RunningJib]

Keep it simple

I'm not fond of the remove clothing option. Too foreward and puts you both in an scenario with limited options

I like the idea of meeting for coffee after work. Even a park will work if public

Keep it simple. Just ask, "would you like to get to know me better?"

Even better if you admit that you have an interest in him.

 

[Hypoxia]

I will let you know. The morning after I will be straight on the forum. Whichever way it goes, I will be honest

Honesty is a trap. Total honesty is a farce. Good lies are best.

Many of my stories contain straight reporting but I don't let that interfere with entertainment. Reality is crazy and should be massaged before being revealed. Too much reality is an overload.

 

[TarnishedPenny]

Well sometimes you just need a Devil's Advocate.

What you said completely makes sense and of course it has ran through my mind.

To be honest, I have been 'playing it safe' and leaving situations dissatisfied or wishing I had said or done somethings different.

I think I agree with your playing a game angle so I think I may have to whip out my post-its.

Your sensible outlook was most certainly appreciated, I am rethinking my 'bold move'.

Da nada. The road to love can often be rough, but true love is always worth it.