Dear Simon…November 2010

Dear Simon
I have been seeing a guy for a while and it was all going really, really well. There was quite an age gap (15 years) but it didn’t seem to matter and he seemed really keen. He was recently single as was I and it seemed to be going well in all departments. We’ve met each others friends, had amazing sex and started talking about meeting each others family. Suddenly I get an email dumping me, saying it isn’t happening for him, which is not what he said a only a week earlier. I am so confused.
Lee, Manchester

Dear Lee
This is a tricky one, especially considering it was done by email as you haven’t really had the opportunity to discuss it further like you would if it was face to face. I mean you could send an email back but will it get read? How would you know? And that could drive you mad. I would say leave it, I mean anyone who dumps someone by text, email, social media (believe me I have heard it all from my single/dating gay friends) is a bit of a loser anyway right? You’re better off without him, onto new and hotter men I say.

Dear Simon
I want a threesome. I want to hire an escort and get down and dirty with him and my boyfriend. I know it is a real fantasy of mine but I’m almost positive that my bf wouldn’t go for it. How do I convince him it will be fun?
Grant – Leeds

Dear Grant
Well, you have me convinced but before you try and convince your boyfriend you need to ask yourself, and then him, a few questions. First you; what do you think you’ll get from this experience that you don’t get from your bf? What type of escort are you looking for? Is he the type that your bf will like or is it all about your fantasy? I’m all for expanding people’s horizons and I think people should be encouraged to try new things but, and this may be the big but for your boyfriend, why do you want to invite a third person into your lives? Get ready for a complete rejection of your idea but that shouldn’t stop you having a go if it’s that important to you.

Dear Simon
I have always been really rather proud of my bottoming abilities. The thing is… I started seeing this guy and after a small wait, ok, ok on the first night, we went back to his and what he revealed in his pants was quite the meat monster. I mean this cock isn’t just long it’s got a ridiculous girth on it (this is starting to sound like a porn movie scenario) but honestly it’s true. The first night, being drunk and up for the challenge, I tried but failed dismally, since then I have tried and tried but little more than the head is going in. What can I do to ‘accommodate’ my man as he worries about it hurting me and has begun to get the droop. I still try all the other things but I want that thing in me. Suggestions?
Lloyd, Cardiff

Dear Lloyd,
Hmmm, I would say patience and a really, really good lube and lots and lots of it. You can’t really do more than that. I would say though take the pressure off the whole bottom thing because subconsciously that won’t be helping you at all either. If this fella is fine to just do everything but for a while then go with it. Enjoy each other and the more you relax the more it will help. It’s not all about sex after all… is it?