For the benefit of those who haven’t read my ‘informative’ rant/opening post on why I’m doing all this (click the ‘About’ menu item if you would like to) here is problem one as submitted to a British newspaper’s advice column:
Problem – I want to try putting things up my arse, and my girlfriend not only finds the idea distasteful, but also is now claiming that I must be gay, seems to have lost any sexual attraction for me, and is threatening to talk to her friends about it (many of whom I know.) I love her and would happily forget about the anal play, but I find her reaction disturbing.
And here is (a summary) of the columnist’s response:
Solution – If it’s not that important, why go on about it? You should tell her that you find her threat to tell her friends a breach of trust.
Say my name, bitch
This solution is as entirely valid as it is not useful. Let’s deconstruct the problem to find out what this guy is actually asking. In the future I may not always show my reasoning so thoroughly, but I want you see my methods. Try to look on me as the Sherlock Holmes of sexuality. Mainly because it appeals to my ego. You can be my Watson. Is it just me or in this context does that sound a bit suggestive? Anyway…
So this guy probably hasn’t just come up with this on the spur of the moment, or he wouldn’t be writing to ask for help about it. In fact he’s probably been doing stuff with his arse while masturbating for a considerable amount of time. Possibly even since he started masturbating in the first place. And, people being the obsessive sorts that they are, he may even have developed this into a bit of ritual to the extent that he finds orgasm considerably less satisfying unless it is coupled with bum play. It’s also worth mentioning that I don’t think that this is a manifestation of a desire to be submissive. If he were sub I suspect he wouldn’t have bought the subject up, and even if he had and was told no, would not then be pursuing this course of asking an external party for further advice. This is dangerous ground, however. So we must cover for it in our response.
So – this is not just a little ‘fun game’ that he’s come up with and thus should be content with forgetting about. This is a fairly fundamental aspect of his current sexuality. In short there’s no way he’ll forget about the anal-play. He may repress it, but it will lurk in the back of their relationship like a cancer. This shit needs resolution.
The girlfriend’s point of view is probably equally long-winded. Why is she reacting like this? Three main reasons spring to mind. The first is pretty obvious. Arseholes are dirty. Ick. Everyone knows that. Or, in short, social conditioning. Perhaps unexpectedly I don’t have a problem with social conditioning – it stops us having to think too much, and this can be useful. While that may sound sarcastic it’s actually not and I may even write something about this fundamental issue at some point. But in the mean time, onwards.
Issue two sounds like one of dominance. All this nonsense about his ‘being gay’ is quite a common reaction to this sort of thing. I suspect she doesn’t really mean gay; she really means less manly – we still live in a world where these two are equated all too often. This, too, is obviously nonsense, but this is how it is. This also fits in with why she has ‘lost all sexual attraction’ for him. Basically she wants her boyfriend to be the dominant partner in their sexual relationship (and no, I’m not necessarily talking about Shades of Grey here – I just mean in the sort of he’s on top sort of way) and is concerned that this indicates a more submissive side to his personality (i.e. being fucked) which generally turns her off. She’s also almost certainly quite young, as well, but then we all were once.
And third she’s probably scared shitless. Blow jobs. Done that. Sex. Done that. Knows what she’s doing and may even feel quite confident about those skills. What the fuck do you do with an arsehole? Is he going to expect me to lick it? How many fingers would I use? Do you fuck hard or gently? Should I wear gloves? And that’s before we even start to introduce things like dildos. And then there might be strap-ons… I MIGHT HAVE TO FUCK HIM! HOW THE HELL DO I DO THAT?
And this all explains why she’s threatening to tell her friends – he has put her in what she considers a very difficult situation, and so she threatens to do the same to him. It’s basically mutually assured destruction. Like a cold war. But with anuses.
It’s hard to say which of those elements is/are the most important, or maybe all three are deeply ingrained. The sub/dom thing is a massive subject, so we’re going to have to make some assumptions there, and since his question wasn’t really that useful, we also don’t actually know what this guy wants his girlfriend to do! Tie him down and fuck him with a strap on, indulge a little butt plug action while they’re having sex or something in between? So, in the absence of more data – situation: analysed.
So – on to my advice!
This problem is not going away, but first consider whether you really want to be with this girl – her behaviour is quite childish and vindictive. If it is only the stress of this situation that has brought this about, that’s kind of understandable, but if she resorts to this sort of emotional and social blackmail all the time, are you sure she’s the girl for you?
But this isn’t useful – we all know you won’t dump her, because you love her. So…
You have quite a path ahead of you – I’d say you’re going to need about 6 months assuming you have sex 1-2 times a week. And don’t fool yourself – you are about to embark on a mission of subtly manipulating her. I personally don’t see this as morally reprehensible, but you need to be honest with yourself about that.
Top tip – do not use a rose stem as an anal dildo.
First you need to deal with her social conditioning about bum-sex in general. Try to introduce her to the pleasures of her own arse. This is certainly not something that’s going to be a quick process. I would advise you start with oily back massages where you occasionally slide your finger down between her buttocks. Over time you can start to put gentle pressure on arsehole. Watch whether her body stiffens when you do this – this is a sign to back off. Back off, mind. Not give up. Over time hopefully she will get used to the feeling of your fingers gently pushing against her sphincter, but make sure you’re still just doing this as part of the overall massage. Don’t get obsessive. When she gets to the stage of parting her legs a little more to allow you to do it, then you can start to rub her clit gently with one hand, and with your other hand put your finger inside her arse just a little bit – literally just the length of your fingernail to start with. (And talking of nails keep them short. ALWAYS!)
To clarify again – this is not all in one session. I’m expecting this to take 20ish massage sessions just to get to this point. We are talking serious slowly slowly stuff here.
At this point you have both tacitly accepted that your finger is in her arse. You can now change your attitude from massage to masturbation, although my advice would be that you keep up the massage as your ‘entry’ to this sort of play until she is fully comfortable with it. You could perhaps change your position as well. While massaging you will probably be looking up her body from the leg end. For masturbation you might want to experiment with turning around so that you’re straddling her back and looking down her body towards her feet. You certainly don’t want to crush her, here, so bear in mind relative sizes and all that, but she may get an additional pleasure from feeling your weight on her. Again, try to be sensitive to her body indicating whether or not she’s enjoying this. No problem either way, and if she doesn’t seem to like it, don’t push it and just go back the other way. However, this information may be useful later!
Seriously – do you really want to have to go shopping for anything called ‘internal cream?’ Different fingers!
The goal now is for her to really enjoy herself while you are playing with her arse. You will improve the chances of this by making sure she is very turned on – long massage before hand, lots of gentle touching, stroking and teasing her clit. Devote half an hour to it if necessary. You may also want to alternate between fingering her arse and her vagina (but use different fingers… it’s not the end of the world if you don’t, but it’s not terribly hygienic, and can lead to thrush which is really no fun and requires someone buying some cream from the chemist which is embarrassing. So just… use different fingers) while she is getting used to all this. And keep it calm and gentle. Don’t get carried away.
Anyway, you don’t need to take all this to anal sex (although by this stage you might want to) but you probably do want to get to the stage where you are using some sort of dildo. I would again advise that you don’t put anything other than your fingers up there until you have got to the stage of her quite comfortably accepting at least two of your fingers more or less fully. At that stage perhaps you could move to a vibrator, but again – gently, gently is the key. Keep it small and non-threatening. She will want to look at it at some point.
If your girlfriend is the orgasmic type, you might want to seal the deal with a few anal orgasms before moving onto the next stage, but if she’s not you’re just going to have to play it by ear. Remember – the point of all this is for her to realise that the arse isn’t dirty and can be pleasurable.
So, next stage. One of the other reasons she’s probably against all of this is that she thinks you wanting things up your bum makes you less dominant. And in a way it does – you are becoming the ‘receiver’ rather than the giver. This puts a responsibility on her to both be in charge and, to an extent, know what she’s doing.
This guy may be a little too possessive. In fact, what the fuck? Whose legs are those? And what’s with that child/monkey. Does it have tits? This photo is weird.
Now here’s an important question. Is being submissive a part of this for you? If so, you’re really going to have your work cut out. If it’s just the feeling of having something in your bum, that’s going to be a lot easier. Because it seems to me that your girlfriend quite wants you to be the ‘dominant’ partner in bed. This comes from a mixture of her attitude (finding you less attractive once she knew about your desires) and the simple fact that most straight women like their partners to be dominant in bed.
Now comes that piece of information from earlier – did she like being straddled? If she really did, that probably indicates that she not only wants you to be the more dominant partner, but she in turn wants to be more submissive herself. There is a subtle but big difference between wanting you to take control and her wanting to be submissive which I will probably explore in later posts. For the moment you’ll just have to take my word for it.
Prepare yourself for the bad news – if you want to be submissive: i.e. that feeling of being fucked and ‘used’ is important to you and she is naturally inclined to being submissive, too, you’re going to have to spend much longer than 6 months on this. You’ll need to roleplay with each other, building up her confidence in being in control, but then also swapping and taking control of the situation as well yourself, sometimes. It needs to be fair so that you both get what you want out of it. This is too large a topic for this post, but I assure you I will cover it at some point in the future.
However, I don’t think this is the case – my reading is that you just like having things in your arse. At this point she will probably be a lot more amenable to this idea just because of the fun that she’s now having with her own. Buy yourself a small butt plug and put it in. Try to encourage her to play with it gently while she gives you a blow/hand job – just any contact between her and the plug is what we’re after, no matter how skilled. And then always lots of positive reinforcement. Comments about how nice it feels. How well she does it. Make it personal. Tell her how good the orgasms are – how they’re the best you’ve ever had. How she makes you feel things you’ve never felt before. I know it sounds corny, and to an extent you may be slightly gilding the truth, but with confidence her technique will improve, and in the end these things will become true by virtue of her feeling good about what she’s doing. As she becomes more confident get a toy she can control a bit more – a vibrator or dildo. Encourage her to put it in for you. Again, try to keep the steps small and manageable.
Finally try out some sex as well. Try getting a larger plug and putting it in and then sitting cross-legged and having her straddle you facing you with her legs around you. The rocking backwards and forwards will be good for you and that position gives quite deep penetration for her, too. Maybe she might even like a plug in her arse at the same time…
And now you really are on a roll. I hope you found this useful, and good luck!
So there we are. That’s what I would have said. Rather tragic that the guy who originally wrote the question will probably never see this post but who knows – it might come in handy for some other lost soul who comes across it on google…