I just read your latest post about the 20 year old guy and felt compelled to write to you for advice, as I really related to his situation and thought you might be able to help me too.
While my situation is similar to his, it is slightly more complicated I think, mainly because I am even more inexperienced than him! I'm 24 and the only ever sexual experience I've had is a mutual wank with a guy in a sauna last year. Sad I know!
That said, I've had a bit of a tough time with the whole gay thing growing up, but I feel like I've turned a corner now and I'm ready to move on and build a gay life for myself. The only problem is, because I've left things so long I feel really behind everybody else in terms of sex and that makes me really nervous and insecure.
This has all become an issue in the last month for me, as I've recently met an AMAZING guy who I've been on a few dates with. And when I say amazing I'm really not exaggerating! I still can't believe I've met someone like him and I can't believe he's even interested in me. He's a few years older than me, incredibly successful in his career (in the sort of way that is both impressive and inspiring because he's done a lot for the progression of gay rights), and he's BEAUTIFUL. He's almost the man of my dreams, something that just a few months ago I never thought existed.
We've been on 3 unbelievable dates so far, all of which have ended up with us being the last people left in the restaurant, and 2 of which have ended up with hour long making out sessions on the street outside :-). While we have very nearly ended up rushing off to bed, we haven't quite made it there yet for one reason or another, and the more I get to know him the more reluctant I am to get into bed with him. He is such an amazing person that I am really worried about doing something that will jeopardize any possible friendship. But then life is also short so I think maybe I should just take the risk and go for it.
The main problem I think has to do with my insecurities. He obviously finds me attractive (he's said as much) but I worry he will be less impressed once in bed. He has been with a lot of guys (really hot ones too) so I feel like I have a lot to live up to. I consider myself a bottom and I've established that he's more of a top (although versatile) so that more or less fits. But I also get the impression that he's a bit of a cock man, as he's always joking about cocks and how they're never big enough. He himself has told me that his is 8 inches and quite thick! I on the other hand am fairly average (about 6 inches) and not particularly thick (I don't think). I've never really worried about it in the past, as I've always thought of myself as a bottom and am not really that fussed about getting blow jobs or fucking guys (I prefer to give and take respectively!) But I'm really worried now that if we do get into bed, I will (a) look really small next to him, and (b) he will be disappointed and not want to sleep with me again, and then I reckon it would just be too awkward to be friends after that.
He knows it's my first time and he thinks we should take things slow. I've also hinted that I'm not as big as him down there but I'm not sure he quite realizes my concerns.
What do you think I should do? Risk it and go for it; or back out while I can and potentially end up with a great friend? Is cock size always so important in gay sex?
To finish off I just wanted to say how much I love your blog. It has really helped me over the years and inspired me to start my own (although it is nothing compared to yours!)
Thanks and hope you're well.
It's always really good to get an email like this which says that someone has found my blog useful :-). I just wish that I had more time, so that I could blog as frequently as I used to.
When I first got this reader's email, I knew that it would be a while before I could do a blog posting for him, so I wrote back with a few bits of advice. One thing that occurred to me was that this reader seemed quite well placed to solve his own problems, because he's very self-aware. Statements like "The main problem [is] to do with my insecurities" are spot on. In this kind of situation, recognising the problem is a significant part of the solution :-).
The first thing that I told the reader was that it's quite understandable for someone in his position to be insecure, and that he just needs to build a little bit of confidence. I also said that it's not "sad" that he's had virtually no experience of sex, it's just the way that his life has worked out so far. In fact, I was a few years older than him before I had my first experiences and for much the same reason, namely that I also had a "tough time with the whole gay thing" before I finally came out.
The reader's dream guy sounds wonderful! What's more, if this guy has done stuff for the progression of gay rights, then he's bound to understand that it takes some people much longer than others to come out as gay. Indeed, someone like that should be very understanding of all the reader's issues. The fact that the reader is slightly new to gay life could well be one of the things that this guy finds the reader attractive.
Regarding the reader's concerns about dick size, I told him that in my experience lots of gay men (including me) joke it! However for most guys (again including me) it's just that, i.e. it's simply joking and fooling around. The reality is that in a real bedroom situation most gay guys really don't care. Of course there are "size queens", i.e. guys who really do want big cocks, but those types of guys are usually very shallow. I'd be amazed if the reader's dream guy is like that, but if he is, I'd suggested that he wouldn't be worth the reader's time after all. Someone like the reader who can write an eloquent email will be able to find much more suitable guys for fun and relationships :-).
In fact, size queens are usually bottoms who want a big cock inside them. I reckon that tops, and hence presumably the reader's dream guy, are much less concerned with cock size. If tops want to be shallow they're looking for tight arses!
Perhaps the most important point that I made to the reader was that he shouldn't back out, because he'll then only have the same problems with the next guy that he likes. All he needs is a bit of confidence, and if he always settles for friendship he'll never start building it. On the contrary, I told him that he should try and his man into bed as soon as possible, because activities with like-minded guys are great fun :-).
After I'd emailed this reader to give him my initial thoughts, within a day I'd received his reply thanking me. I then didn't email him until a few days ago, when I asked him if there had been any developments that I should take account of while I was writing my blog post. His reply was as follows:
Things have got very complicated with the love of my life unfortunately. He is incredibly busy at the moment with different business projects that we have only managed to see each other once since I last wrote to you! :-( We did have a good chat though and established how much we both like each other. And he reiterated that he is very cautious not to rush into anything, as apparently he has been hurt in the past.
While we were in fairly regular text contact I still thought that it was getting a bit ridiculous at how little we were seeing each other so I ended up telling him off last week. I think I do believe him when he says he is just so busy at the moment but I also can't help but feel that he may be playing the field as well, which makes me feel stupid because I am being so good! I told him this and his reply was that he feels bad I feel stupid and that I shouldn't wait for him while he is so busy. He has since gone even more quiet although he does still reply to my texts in a nice way.
Anyway, I have been doing major damage control. The whole saga has made me look objectively at our friendship/relationship and decide what is really important to me. And so I wrote him a LONG email today outlining what that was - basically in a nutshell I said that having him as a friend is by far the most important thing to me because I find him so inspiring. Anything extra would be a bonus and is up to him. I am awaiting the reply but I think what might happen is that we will continue down the friend route for now. I think he is incredibly special though so I do still want him to be my first sexual encounter. Who know what will happen but I reckon if we decide that a relationship is not in our best interests he might still be willing to show me the ropes sex wise in a sort of friends with benefits way? I'm just speculating though although if that were to happen then my original concerns from my first email would still stand - i.e. is cock size really that important?
In my experience, if someone seems to be going much slower than someone else in terms of starting a relationship, then it doesn't do any good to try and hurry them. Sometimes their lack of speed is simply trying to give a message that they're not as interested as they originally were. Furthermore, although they may say that they like someone a lot, subconsciously their thoughts may be slightly different. So it can be their subconscious mind that causes them to delay meetings, because they just know that something isn't quite right for them.
Regarding the reader, the guy is saying that he wants to go slow, and it sounds like the reader is trying to push him to go much faster. My guess is that it's been the reader that's been setting up all their meetings and starting all their txt msg conversations. I didn't realise it from the reader's first email, but it now sounds to me very much like the reader has a big crush on this guy. The guy on the receiving end has probably been feeling that the reader is far too keen, far too intense about a possible relationship, so I'm not at all surprised to hear that the guy has been even more quiet recently.
So what should the reader do now? Unfortunately I reckon that he needs to start getting over this guy, because I think it's unlikely that the guy will want to have much to do with the reader in the future. The only way to salvage the situation might be to have no contact for a couple of months or more, and then to send a very short txt msg, apologising for being too intense previously. And if instead the other guy contacts the reader before the reader contacts him, then the reader should leave it at least a few hours before replying, and play it cool and casual when he does reply.
Does anyone else have any thoughts for this reader?