Myself and my boyfriend have experimented with anal (him on me) and I really enjoy it, although I have never done it before. We haven't used any toys or anything, just fingers and anal sex. But the other day we were joking around and he mentioned that he would like me to try anal on him, to see why I like it so much. He hasn't done anything like that before.
I was wondering if you guys could recommend me something to have a play with? Ideally something not too intimidating and suitable for a beginner. Should I put a condom over the toy when using it on him?
Since you've already had experiences with anal i'm assuming you know about the importance of lots and lots of lube and all the good stuff. Do you know if he's had any experience with his own fingers? If not, that's a really good place to start. Massive fun can be had with prostate massage finger wise (you really, Really want to find the prostate, it's a winner.) It'l also give you a chance to work out if he likes bum fun before you invest in a toy, and will get him more comfortable with having things up there.
Since it's going to be for his bum i'd definatly get him involved in picking it out, even if he only approached you jokingly, this will be a good way of showing him that you are really okay with it and that you're fine with him getting into it. Some people can feel a little nervous admitting or declaring that they want to try something, so him saying it jokingly might be a sign that he is unsure. He might have been trying to gauge your reaction. Also, it's just generally good for the person to choose what they want.
Course anything you go with should have a flanged or larger base just to stop it disapearing. Unless he has the worlds most intense medical fetish, then having the toy greet the light of day in the gloved hand of an A&E nurse wont be fun.
Putting a condom over a toy is a good idea, especially if it's a toy you are going to be sharing, but it isn't essential so long as you give it a really good clean and it isn't a porous material. Silicone, while it tends to be more expensive than things like jelly and rubber, is a wonder material for anal toys. Easy to clean, non-porous and can be boiled. Stay away with silicone lubes with silicone toys though cause they can go to war and it'll be the toy that looses.
If I haven't covered anything then i'm sure all the other lovely folks here will. Or just ask more questions. =)
Oh yes I'll be sure to use plenty of lube etc whatever we do, and try with fingers first. Thank you both for the links, I will take a look and if he does feel comfortable with it after some experimentation with fingers I'll broach the subject of a toy with him and see how he reacts!
I agree about making the toy purchase a joint venture. It will allow him the opportunity to indicate what sort of activity he has in mind - it's possible he has pegging in mind in which case he can guide the search to the LH strapon page as a way of 'testing the water' as to your thoughts on that idea. In my experience it's hard to summon up the courage to tell your SO about this desire.
I would also point out that softness in a toy is almost as important as keeping the size in check. If you tense up a hard toy can really hurt even if its small.
You might want to consider a douche as one of your purchases. He may find it easier to relax if he knows there are going to be no unpleasant intrusions (extrusions?) into your fun.
I would recommend the assberry, not to big so good for beginners and the removable vibrator is great, plenty of lube. Hope this is helpful and still relevant.
We used these last night http://www.lovehoney.co.uk/product.cfm?p=2219 and he liked the sensation of them being moved in and out.... Im not sure he'd go for much bigger to be honest!!
I think a finger would do the same job, though this vibrates and has a tiny tip, so you can litterally go from nothing and build up to a finger sized insertable, if a finger is too much/too frightening!