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Practical Advice For The Night

Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
I'm new to this site but it seems like a good place to get advice.

Basically I'm a Guy who's in his 30's and still never had sex. The closest I've gotten is kissing a girl on the lips, kissing her stomach, etc

Never done anything else more with a girl.
Anyway I've been chatting online to a woman that is also in her 30's and not done anything other then kiss a guy.

I've enjoyed chatting to her and we've exchanged pics and we've decided to meetup in a nice hotel one weekend and lose it together :)

We're both up for this, and we're both really looking forward to reaching this milestone togther, but off course as the date gets closer I'm sure we'll be getting nerves.

What I really want is actual practical advice on what people think we should try doing on the night. We plan to meetup, talk, have some drinks and then go back to the Hotel.

But what I want is advice like what positions would people recommend we try, do people recommend the man or woman putting on the condom if it's the first time for us both?

Should there be some background music?

Should we try more then one position? is it better to put a pillow under the women for a better angle, etc?

Should we attempt oral?

Basically anything and everything practical people can advise upon would be great.

We both live really far away from each other and both travelling huge distances to do this and only got the one night together.

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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Well, to be frank, its not going to be perfect like it is in films. Nobodys first time is (rarely). You dont even know this woman, neither of you have done anything sexual and you're expecting it to be amazing, mindblowing orgasmy.

    My advice would be to go slow, very slow. Dont feel the need to jump straight in but take your time just feeling each other. You'll both most likely be nervous and that will inhibit any adventerousness and make you tense up which will then probably not get either of you anywhere.

    Relax, chat, have a couple of drinks, anything to make you both enjoy the moment rather than stress out about how its going, is it perfect, am i doing it right etc etc

    Hope that helps :)
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    katypatatykatypataty Posts: 21 Boards Initiate
    Hi TomThumb :wave:

    Welcome to the boards!
    Completely appreciate that you're feeling nervous about having sex for the first time...it's totally normal.

    In terms of practical things you can do - I agree with Lexi99 - go slow and try not rush into anything too fast as it's likely to make you more nervous. It sounds like you've both been really honest with each other about the fact that this is the first time so you're already on level footing - keep that in your mind as much as possible.

    Agree that it's not going to be like porn movie either! Do what feels right at the time...maybe just you on top and then her? But don't be afraid to be experimental if you both want to. Music is always good to relax the mood so you can always whack on some Kenny G! Little tip about condoms - if you're not used to using them, it's always useful to practice putting one on a few times before you actually do in the heat of the moment! Can help take the pressure off a bit.

    Also, make sure you tell someone where you're going and for how long - it's always a a good idea no whatever what your age or gender when you're meeting someone you've met online for the first time.

    Good luck!

    :yippe:
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Hi :wave:

    In regards to your question about oral. The more you stimulate her before actually attempting penetration will make it easier for you both. So I would probably go for about half an hour of foreplay first before actually attempting to engage in any proper sex with her.

    If you don't plan to use lube then make sure your penis is well lubricated whether it be with saliva or something else, be aware if you do plan to use lube with condoms though, some oil based lubricants can split condoms.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    I agree with what the previous user advised, about perhaps trying condoms by yourself before trying to use them in the actual situation. It might make putting one on a lot easier when the time comes.

    Things to mention are:

    1) Be careful with fingernails when putting on a condom, you don't want to cause a tear or a weakness.

    2) When you apply a condom, pinch the end (the little teat) to ensure that air doesn't get in when you roll it down. Pinch and hold between thumb and forefinger of one hand whilst rolling the condom down with the other hand.

    3) Ensure that the condom is fully rolled down as far as it will go. If you don't roll it down enough then it can slip off during the act.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Thanks for all the advice so far.

    I'm still wondering about what to do in what order.

    I'm thinking about trying massage to get used to touching her and also to get her relaxed, if that goes well then was thinking of kissing her neck, shoulders, etc before exploring other areas.

    from what people seem to be saying oral seems to be pretty standard stuff ? And a way to get a woman ready for penetration?

    I found a very interesting video on a well know porn website, but it was very instructional with 2 women in the video - and one was demonstrating on the other how to please a woman with both mouth and fingers.

    Only thing was the video seemed to be aimed for an experience woman to be on the receiving end and since neither of us have any experience beyond kissing someone else I'm not sure how far to go.

    What I'd most like are suggestions of what to do in what order.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Relying on a porn site may not be the best idea.

    As others have said, don't set this up to be a hugely amazing event. Planning what to do in advance isn't necessarily going to help as every time is different and spontaneity is half of what makes it fun.

    If it were me (which I know it's not) I'd go out somewhere first to get something to eat and have a couple of drinks with meal. That way you get to know each other in person and will be more relaxed later on. After, go back to hotel (you said you were both traveling long distance?) and watch a film. Hopefully there's a sofa in your room but if not a bed is ok.

    Start light physical contact - arm around her, head resting on shoulders or in lap. If you end up feeling more comfortable lying across sofa or bed then do so. Continue light physical contact - hand on her leg or touching her hair. If it gets to point where film is becoming a distraction then turn it off and put on some music.

    Cuddling on the bed might then be a way to go. If you want to give massage now is probably the time to do so, and kiss if it feels right. If an item of clothing is getting in the way remove it and continue exploring each others bodies. Assuming there is good physical chemistry between you (which can be difficult to know until you actually meet) this should happen fairly naturally. Once underwear has been removed you can think about how to use your hands/mouths to turn each other on more. While you may have read or looked at suggestions for what to do try to be slightly creative. If something is working continue, if it's not, try something slightly different. Don't make it just about pleasing her either (although that's obviously important) - allow her to practice on you too. At this point things should be becoming fairly instinctive, and if you want to go all the way remember to put on the condom!

    I wouldn't worry too much about trying 101 positions, either her or you on top is probably good enough to get started. Then just do what feels good.

    Given that you haven't met each other yet there is a chance that when you do you won't click (for whatever reason). Keep this in mind as you don't want to build up massive expectations to be ruined.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Also, agree to communicate. Don't go ahead with it for the sake of it if there's nothing there when you finally meet.

    Every woman (and, for that matter, every man) likes different things so talk to her and ask her to tell you when something isn't quite right.

    Above all things, relax. Don't try to overthink it or do everything 'perfectly' as you've planned it because life doesn't usually work like that and you'll end up too tense to enjoy it.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    do it all with natural.dan enjoy the relationship.you do not get too weird minded.because it will eventually be a burden on your own.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Also, watch the drinking, especially on your part.

    Too much to drink and struggling to keep an erection often go hand in hand.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Also, watch the drinking, especially on your part.

    Too much to drink and struggling to keep an erection often go hand in hand.
    :yes:

    Ditto weed. From experience :yeees:.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    krng wrote: »
    Relying on a porn site may not be the best idea.

    If it were me (which I know it's not) I'd go out somewhere first to get something to eat and have a couple of drinks with meal. That way you get to know each other in person and will be more relaxed later on. After, go back to hotel (you said you were both traveling long distance?) and watch a film. Hopefully there's a sofa in your room but if not a bed is ok.

    Start light physical contact - arm around her, head resting on shoulders or in lap. If you end up feeling more comfortable lying across sofa or bed then do so. Continue light physical contact - hand on her leg or touching her hair. If it gets to point where film is becoming a distraction then turn it off and put on some music.

    Cuddling on the bed might then be a way to go. If you want to give massage now is probably the time to do so, and kiss if it feels right. If an item of clothing is getting in the way remove it and continue exploring each others bodies. Assuming there is good physical chemistry between you (which can be difficult to know until you actually meet) this should happen fairly naturally. Once underwear has been removed you can think about how to use your hands/mouths to turn each other on more. While you may have read or looked at suggestions for what to do try to be slightly creative. If something is working continue, if it's not, try something slightly different. Don't make it just about pleasing her either (although that's obviously important) - allow her to practice on you too. At this point things should be becoming fairly instinctive, and if you want to go all the way remember to put on the condom!

    Basically everything you've said is basically the way I kind of want things to go .. Not sure about the girl though, she seems more keen to just turn up at the hotel room and get down to business, whilst I'm the one that wants to take their time and meetup in a bar far and do some talking, etc.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    rosierawrz wrote: »
    letting the girl go on top and being in control of speed etc for some of the time, thats always a good idea.

    For my first time my boyfriend suggested I got on top, cos I was pretty tight still and not used to having things "up there" so to speak. This just made it easier because I was in control so could go as slowly or quickly as I wanted and he didn't have to worry about forcing it in too quickly and hurting me. Good suggestion :)

    Although it depends how self conscious she is. Women can feel pretty exposed when they're on top, especially if they're not used to people seeing them naked...
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    :yes:

    Ditto weed. From experience :yeees:.

    :no:

    Not so. From over a decade's experience :cool:
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Spliffie wrote: »
    :no:

    Not so. From over a decade's experience :cool:
    Obviously you're very lucky, then.
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    Former MemberFormer Member Posts: 1,876,323 The Mix Honorary Guru
    Obviously you're very lucky, then.

    Not really, for a lot of people its an aphrodisiac. For some people, having sex whilst tripping might not be on their mind and they don't function as a result, their failure to attain erection somewhat similar to their failure to speak in a coherent fashion.
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