Okay, let's do this...

Well, for starters, no need to overthink it; try and relax and take it easy. Communication is always best, as sex is more than a physical activity, your brain is the the biggest element of sex. So in that regard, you should not be concerned about telling him. If he knows, and understands, it will help the experience be better for the both of you. if you think the few hints you dropped have actually sufficiently informed him and he already knows, then continue to go with the flow. Enjoy it!

 

Trust your instincts. Reality is far different than virtual chat.

I magine if you meet and he is NOT what he indicated in chat. Age 15 or 82, or some other distortion

Go expecting NOTHING except to meet. Meet with no expectations.

 

I am not experienced either but I would agree about not overthinking it. Remember that having sex with him won't define your sexuality. Hopefully, it will help you figure out a bit more about who you are and it might feel really great in the process.

If it is awkward, it doesn't mean you aren't gay. It sometimes is awkward and that is ok too. You might also enjoy it and find you are also attracted to women. There are a lot of possibilities. This act is only one thing.

Let us know how it goes.

 

OK, first up, congratulations for wanting to take your exploration further.

So, what I've done is tell the guys I've been with the truth, open and honest about my lack of experience. Hasn't been an issue.

Took to oral sex like I'd been doing it since I was 13. Only 2 guys so far have received from me. 4 others were all givers Haven't tried anal yet, because I want to find someone who I can see more than once. So, call me the 50 year old anal virgin.

There's only so many things you can do. So, list them out, set boundaries, like we're only going to go so far, the first time. Don't worry about performance, set your expectations low. It's not rocket science...

Make sure you are truly comfortable with everything along the way... don't force yourself to enjoy something. If it's painful, revolting, or just not your thing, communicate that to your partner. You don't have to do everything the first time.

 

Well, let's see here.

First off, as others have said, relax and go with the flow.

Second, don't be ashamed of your lack of experience and let him know so he can pace things accordingly.

Beyond that, some suggestions...

Don't worry about coming too soon. If it happens, it happens. Rest a bit, cuddle, kiss, do nice stuff to him, and most likely you'll be up for another round in 10-20 minutes or so. Or he will have cum too, and then you can both rest and recharge for another go.

Don't worry about being 'big enough'. Penis size is going to be pretty much irrelevant for anything you are likely to do outside of topping, and you don't need to be all that big (regardless of what porn says) to give a bottom a perfectly satisfactory experience.

If you are giving oral, mind your teeth. It's really not that hard a skill to learn, just take it slow at first.

If you think intercourse is going to be part of this, refer to the page on EC about preparing for anal sex. Although, personally I'd recommend holding off on anal until you've gotten comfortable doing other stuff with him. It's easier to relax with someone your mind already associates with pleasure. Similarly working up to it with fingering, toys of various sizes, and possibly practicing alone and then together with fingers and toys isn't a bad way to build up to it if you don't mind it taking a bit longer.

Don't worry about 'not knowing anything'. If you know how to masturbate you already know how to do something(s) that most guys are going to like at a basic level, although you may need to adjust a bit from your normal technique since guys can all be a bit different in their preferences in this area.

Pay attention to your partner. If what he's doing feels good, consider returning the favor. If what you're doing has him breathing harder, moaning, and/or thrusting involuntarily...consider doing it more.

Know your boundaries (temp or permanent) and respect his. He should return the favor.

Don't forbid yourself to extend your boundaries if it feels right to do so.

Always practice safe sex.

Have fun.

Hope this helps,

Todd

 

What's the big deal? Just tell him that it is your first time, or your first time with him so he needs to be a little patient with you and not go farther than "X" this time if you want to set a limit. He will be so happy that it is your first time, he won't care how well you are doing it.

 

Dante's Inferno put the fear of God into me for the first time in my life! At the time it never occurred to me, but I was desperate to revert back to Christianity after denouncing my fate. I would never be graced with the presence of the virtuous pagans. If I gave myself the benefit of the doubt, I might stand before the Gates and be incessantly consumed by ravenous maggots chasing that flippant banner...it was a great read though. I'm sorry your thoughts are so haunting.(*hug*)
As for your current situation, just tell him you've never been with a guy. From my personal experience, I told a friend, and he found that "cute". Not sure why, but it's nothing to worry about. Maybe my naivete was what made him say that. He told me he had fun "teaching" me how to have sex. I think it gave him a sense of power in a way. It doesn't have to be anal. If it comes to that, there's lots of tips on how to douche(if you're bottoming).

 

I'm sorry bud, sometimes life is a crapshoot... no guarantees...

I can't help you with that aspect of this.

 

If the expectation you have for your first man-to-man experience is that you'll hate yourself afterward, it seems to me that you are greatly increasing the chances that what you expect to happen actually will.

Maybe you're not ready to have sex? If so, why set yourself up for a negative experience? Maybe you need to wait until you want it so badly that you KNOW you'll have no regrets? Or maybe you need to proceed very slowly and stay fully clothed until you're comfortable with what you want to do?

"Staying safe" is the strategy I've successfully used for myself when it comes to dating. When I first became single I had a very positive attitude, but after a series of not-good experiences, I became very negative and cynical. Eventually I realized that I needed to stop torturing myself by hoping that my next experience would change everything.

My solution was to set myself up for only positive experiences. The way I did that was to forget about finding a relationship and instead focus on making new friends. That was more than two years ago and I am so pleased with my life now. I have loads of real, quality friends and a busy life that makes me feel whole and fulfilled, even though I've been celibate this whole time.

It's taken me far longer than expected, but I have finally reached the point where I'm totally confident that I can date now and not be sent into an emotional tain-spin should something bad happen. I can't tell you how terrific and empowering it is to feel in control of my own happiness, regardless of what others might throw at me!

As disappointing and/or difficult as it might be to accept, maybe your fears are an indication that you're not ready to take this step?

 

(*hug*)Wow, Benway. I hope you're feeling better and hurting yourself is not a good answer.

 

Benway I hope and pray that you can come to a place of self acceptance. Easier said then done but I get the sense that you are well worth doing so! I too overthink things to the nth degree but am learning not to do so... when I let go I actually enjoy myself and it feels much better than bashing myself (literally or figuratively).