How to make a shy guy feel more comfortable?

[Hopeful30]

I've started seeing this guy who is visibly nervous around me. When we fool around, he treats me like I'm made of glass: gentle kisses and touches, light petting, always making sure I'm comfortable.

I absolutely love this, but I sense that he continues to be nervous with me, despite that I've made it obvious that I'm into him.

There is no doubt that soon we are going to have sex. How can I make him more comfortable? He's made joking comments about 'doing a good job ', and I've made it clear that it's a team effort and we can always practice to get better (lol).

How can I show him (without making him feel awkward) that he has nothing to worry about? I'm genuinely easy going and open to trying new things. I want him to fully be himself during sex without being so concerned about performance. 

[smackie9]

He won't be fully himself until he's had sex with you a few times. Having sex is where a guy's confidence comes from IMO.

Edited July 1, 2020 by smackie9

[Hopeful30]

2 minutes ago, smackie9 said:

He won't be fully himself until he's had sex with you a few times. Having sex is where a guy's confidence comes from IMO.

Should I expect the first time to be awkward and full of nerves?

[smackie9]

Most, (not all first times), yes it will be...as they say it is what it is.

Edited July 1, 2020 by smackie9

[contel3]

If its only the sexual aspect you're worried about.... why don't you just...take the initiative? Like, grab him passionately, take his hands and press them harder into your body? 

Probably works better than having an awkward discussion about it. Most guys will leave all their inhibitions at the door once you make them feel like they're the sexiest thing you've seen since before quarantine. 

Edited July 1, 2020 by contel3

[Hopeful30]

4 minutes ago, contel3 said:

If its only the sexual aspect you're worried about.... why don't you just...take the initiative? Like, grab him passionately, take his hands and press them harder into your body? 

Probably works better than having an awkward discussion about it. Just get him aroused enough and he'll forget about the awkwardness.

Been there done that. He doesn't doubt my interest (from what I can tell), I think he's insecure about his performance. He's also shorter than me (story of my life) and has brought it up a few times, which is annoying. That was my first clue that he is insecure about his 'manhood', which translates into the bedroom I imagine. Curious how I can ease his nerves without doing all the work.

[contel3]

10 minutes ago, Hopeful30 said:

Been there done that. He doesn't doubt my interest (from what I can tell), I think he's insecure about his performance. He's also shorter than me (story of my life) and has brought it up a few times, which is annoying. That was my first clue that he is insecure about his 'manhood', which translates into the bedroom I imagine. Curious how I can ease his nerves without doing all the work.

Uuuuuuuf. Thats a real bummer.

How did he react when you made a move?

[Hopeful30]

20 minutes ago, contel3 said:

Uuuuuuuf. Thats a real bummer.

How did he react when you made a move?

He reciprocated and kept poking me in the hip LOL but I was on my period that time (told him before hand to not lead him on) so he knew we wouldn't have sex then. 

Now that I think about it, he's very sexual, just not that confident about it. Is it possible he still doubts how much I want him even though I've made it obvious? Or do shy guys typically take more time to open up and be comfortable in the bedroom? And that's the thing, he's not shy. Went for a kiss on the first date...but I can sense he gets nervous.

If only he knew the extent of all the dirty things I want to do to him (which I won't say not to scare him LOL)

[Ami1uwant]

1 hour ago, smackie9 said:

He won't be fully himself until he's had sex with you a few times. Having sex is where a guy's confidence comes from IMO.

 

Does a blow job count?

[Roswell91]

5 minutes ago, Hopeful30 said:

He reciprocated and kept poking me in the hip LOL but I was on my period that time (told him before hand to not lead him on) so he knew we wouldn't have sex then. 

Now that I think about it, he's very sexual, just not that confident about it. Is it possible he still doubts how much I want him even though I've made it obvious? Or do shy guys typically take more time to open up and be comfortable in the bedroom? And that's the thing, he's not shy. Went for a kiss on the first date...but I can sense he gets nervous.

If only he knew the extent of all the dirty things I want to do to him (which I won't say not to scare him LOL)

Why you thinking and analysing so much. If you want to do it just go for it. 😂. 

How does he get nervous?

Maybe its a height thing. How tall is he and how tall are you 

Edited July 1, 2020 by Roswell91

[Fresh_Start]

2 hours ago, smackie9 said:

He won't be fully himself until he's had sex with you a few times. Having sex is where a guy's confidence comes from IMO.

You must have dated some real pantywaists if you think that's even remotely accurate.  Confidence is a state of mind.  It's an ingrained part of your personality. 

Having sex is just the cherry on top of a sundae.  It's satisfying, but it doesn't fundamentally change the entire sundae.   

[smackie9]

I believe the more sexual experience a guy has the more confidence he has....it makes sense. Yes there are those are born with a confident personality, such as yours, along with naturally good looks, it's obvious you are going to think that way.

[smackie9]

2 hours ago, Ami1uwant said:

 

Does a blow job count?

That sure will pump his tires!

[d0nnivain]

Don't make an issue out of it.  Act like his lack of confidence doesn't bother you & that you're fine with it.  Do lavish the praise without becoming obsequious but any attempt to discuss it will draw too much attention to the shorting come & cause him to shut down more.  

[alphamale]

fellatio always put me at ease

[K.K.]

^ ^ 

😁 ha ha  

[Cornholio12]

Convince him to have a few beers and jerk off. Puts the mind at ease  

[Fresh_Start]

3 hours ago, smackie9 said:

I believe the more sexual experience a guy has the more confidence he has....it makes sense. Yes there are those are born with a confident personality, such as yours, along with naturally good looks, it's obvious you are going to think that way.

I simplified it to a pretty extreme degree for the sake of brevity because I was posting between calls to my clients and didn't feel like giving a more detailed answer. 

While I probably won the genetic lottery when it came to the traits I inherited from my parents, many of which have certainly paved the way to opportunities that others might not have, most of my confidence was something that I acquired over time by overcoming adversity and with achievement -- achievement of goals, achievement in sports, achievement in bodybuilding and powerlifting, achievement in the business world, etc.  I definitely wouldn't go so far as to say that I was born this way, even if I was born with a natural predisposition for it.  In that regard, there's probably some truth to what you're saying.  I would say, as a caveat, that if a man's confidence is contingent upon having sex, then he's not very confident to begin with.  It would be a superficial confidence that could fade away after a prolonged period of abstinence or, heaven forbid, a serious accident or injury resulting in castration.

Now, if you're referring to confidence in one's sexual abilities and prowess then I agree 100%.  The first time I ever had sex it was a little awkward and I couldn't even put the condom on right.  I think I broke one or two of them before I finally figured it out. lol  Over time, with experience, I mastered the art of oral sex.  Now I almost always start "a session" by giving oral to a woman, give her an orgasm, and then it's my turn.  I'm very confident in my ability to do so and in that regard it's entirely predicated upon experience.   

[smackie9]

No I have counseled / coached several nervous insecure nellies. They were awkward, had trouble taking to girls, some hid away at home playing video games, etc. Once they had sex, it was like an enlightenment. Getting over that initial "hump" so to speak, their fear and anxiety melted away. They completely changed, and yes confidence started to develop within them. As they were able to explore more options they were really off and running.

[Haerts]

There are some guys who are not necessarily shy, but they need some time to "trust" you're really into them. In my experience, that usually happens when you're very confident within yourself and they're not about themselves. They might think you're way too beautiful for them, but what they don't realize is that you want them too.

I don't agree that a guy's confidence comes from sex though. If a guy is confident about himself, he will be and that's it. If they have to have sex with you a few times to finally feel confident, then it's clear he's seeking some sort of validation from you. Which is not necessarily bad, but definitely an issue he needs to work on (and it has nothing to do with you).

[Fresh_Start]

1 hour ago, smackie9 said:

Getting over that initial "hump"

I see what you did there.

Insecurity, fear, and anxiety are some pretty serious issues that I just can't see being completely resolved by sex.  All three of those, particularly insecurity and anxiety, often require some pretty intensive therapy and even medication that can be a lifelong battle for some.  I'm having a hard time envisioning someone going into a therapist's or psychiatrist's office and saying, "I suffer from anxiety and insecurity" only to get a response of, "Just have some sex and it'll all go away." 😁

Edited July 2, 2020 by Fresh_Start
terrible emoji

[Hopeful30]

7 hours ago, smackie9 said:

I believe the more sexual experience a guy has the more confidence he has....it makes sense. Yes there are those are born with a confident personality, such as yours, along with naturally good looks, it's obvious you are going to think that way.

This is where I'm confused. He's been in some "sexual situations" that are not common for an inexperienced man, such as birthday parties for women who do porn, underground sex culture events, and even using sexual slang and I need to ask him for clarification. Even our first date he spent talking about sex cultures and fetishes the entire time (respectful, nothing degrading). 

All this gave me the impression that he's a slut (forgive the language). Is it possible that he's simply perverted and inexperienced? 

[mortensorchid]

I have faced this problem quite a bit in my dating life, I have come to realize fairly recently.  I am a strong, Alpha female.  Friends have joked with me that they are not sure which one (my bff is a guy I will call Dave) which one of us is the man in the relationship.  Someone suggested something to me, a dating coach I connected with on Facebook months ago which I never thought about before.  We were talking to each other (me and the dating coach) on a video call and she said I strike her as being a very serious person.  I said yes that's the case.  She said that's my masculine side coming out almost completely, and my masculine energy sends out a vibe which appeals to the feminine energy in men around me.  Hence that's why I have attracted introverted, weak men.  Her solution to this was for me to embrace my feminine side more (wear makeup, dresses/skirts, etc.), but I digress on this point for now.

If you find yourself with a weak or unsure man, unfortunately, in the long run they will not make the commitment.  In many cases they can't even make a simple decision.  Just before the virus shutdown, this guy I went out on an internet date with was so weak he couldn't even order his own food off the menu in the restaurant.  I had to tell him what to get!  I knew then and there I would never hear a word from him again, which I didn't and I was quite depressed about it just thinking "another loser".  It's hard to have to accept but I think you should reconsider things with this guy if he is constantly nervous, afraid, etc.  What makes you think you can change that?  Unfortunately all the love and understanding and whatever else cannot change it.  

[salparadise]

17 hours ago, Hopeful30 said:

That was my first clue that he is insecure about his 'manhood', which translates into the bedroom I imagine

Is this the same guy who was violating boundaries by going for a kiss on the first date, and who you were afraid might have a micro-peen, or be smaller than average? 

If he's not moving fast enough now, I'd say lead him to a dark alley, unzip, and give him a sloppy, wet one. And be sure to make eye contact.

[manfrombelow]

19 hours ago, Hopeful30 said:

I've started seeing this guy who is visibly nervous around me. When we fool around, he treats me like I'm made of glass: gentle kisses and touches, light petting, always making sure I'm comfortable.

I absolutely love this, but I sense that he continues to be nervous with me, despite that I've made it obvious that I'm into him.

There is no doubt that soon we are going to have sex. How can I make him more comfortable? He's made joking comments about 'doing a good job ', and I've made it clear that it's a team effort and we can always practice to get better (lol).

How can I show him (without making him feel awkward) that he has nothing to worry about? I'm genuinely easy going and open to trying new things. I want him to fully be himself during sex without being so concerned about performance. 

How come I never met patient & sympathetic women like you during my nervous and awkward days?

I guess this guy must looks like prime Brad Pitt or he must have some really outstandingly amazing quality to make you accept his nervousness (which is a deal-breaker for women) instead of ghosting him after the 1st date.

Edited July 2, 2020 by manfrombelow