This Week - Escort first time, Tangled limbs and Sharing sex Anthony asks:
I have scheduled my first overnight appointment with an escort. What do I do now? I don’t want to come off as a sex-crazed person or as someone who doesn’t know what he is doing. How do I spend all that time with him? Talk, dining, a shower - what? This will be my first meeting with an escort.
James says:
Well Anthony, you will have the best time with an escort if you show him respect and don't treat him as a sexual animal! If you are spending an overnight with an escort then you will arrange a time when he will arrive and a time when he will leave. This would usually start fairly late so dinner may not always be an option although that would of course be nice if there's time.
If it is too late for dinner then maybe a drink somewhere first would be a good way to get to know each other a bit and relax. It also depends where you meet him. It is always polite to have a shower when the escort arrives or to have showered just before. Tell the escort this and ask if he would like to have a shower too. Usually he will have had a shower before leaving to come to you.
If you are nervous then tell the escort that too as he will be more used to the situation than you and will be able to help you relax more! Above all just relax, take it as it comes and enjoy it! It is always a good idea to chat to the escort on the phone as well before making a booking and check that he accepts what you have in mind. It will also give you a chance to see if you will get on as well.
It is possible to hire and escort by email but it is always advisable to talk on the phone as well. Many escorts will require you to confirm any booking by phone anyway on the day.
James asks James:
Everyone talks about side-by-side sex as being the most comfortable. Where do you put all those legs and should the fuckee have one leg in the air or flat down on the bed. Help! I'm a tangled mess of limbs! Please explain exactly as I'm so confused. Also if that's the most comfortable, then what position gives the deepest penetration?
James replies:
Hi James, yes side-by-side or spooning as it is also known, is the most natural and comfortable position for anal sex. This is because it allows the dick to follow the contour of your ass in the easiest way.
You should both keep your legs down at the start so have the guy fucking put both his legs on the back of the other guys legs. As you get used to this you can then get the guy who is being fucked to lift one leg in the air - this allows easier entry and you should be able to go deeper as well.
Try to relax about it all and don't plan it too much. Let things just happen and you will enjoy it more. Also don't be afraid of changing positions - let it flow naturally and you will find out just what's the most enjoyable for you both. Make sure you talk when you are having sex as this will make it easier and more relaxed for you both.
Deepest penetration comes when the guy who is being fucked sits on top of the active guy (who is lying on the bed face up) or when the passive guy is lying on the bed face up with his legs behind his head or as far back as he can go with the active guy facing him. This is a great position as the active guy can also put his hands on the headboard, so he can really slam in, and it also allows the two of you to kiss as well.
Try out different positions and see what works best for you and your partner! Talking during and after sex is the best way by far to improve your sex life.
Jay needs to know:
I met my boyfriend a couple of years ago, I was a virgin (with guys) and he was well experienced. We have a great sex life together but he keeps saying he doesn't like the idea of other guys sharing me. I quite like the idea of getting some sexual experience with other men so what do you suggest I do. I am very happy with him, and we get on well, but I do want to try other types of sex.
James answers:
Jay this is quite common between boyfriends and it is often the case that one guy is more keen on sleeping with other guys than the other. You are probably just more sexual and a bit more adventurous than your partner.
There is also a jealousy factor coming into this as well though. Only you know your boyfriend and understand your relationship enough to decide whether this is something you can talk about with him. You also need to decide what you want. Do you like the idea of having threesomes? And do you think he would be able to cope with that? Or are you more interested in the idea of having sex alone with other guys? And if so are you going to tell your boyfriend and be open about it? Some guys have very successful open relationships whereas for others it can become too difficult and they get very jealous about you having sex with someone else which can put an enormous strain on the relationship.
Have a think about your own personal situation and relationship and make sure that you make the right decision that makes you both happy and doesn't put your relationship in danger.
