Been there, seen it, done it.
I suggest you use candles. The wax is sterile and in any case you can always use a condom. It comes in all different sizes. Dont be too adventerous to start -use plain shaped candles not the twisted fancy variety. Nor do I suggest you try the huge ones you find in Churches. Dont forget the lubrication.
There are several advantages to candles:
They are cheap.
They dont invite suspicion - apart from the obvious use as an emergency light they can be found in mechanical situations where you want lubrication for saws and drills.
Most gay guys dont seem to realise that your anal passage is not straight. It curves. Candles have a low melting point. After a minute of two after entering the body they will take up the shape of the passage.
Despite what is said they are highly unlikely to break.They have a string wick inside which holds them together.
I have a muscle massager to which I tape a candle. I get a fantastic orgasm when the vibrations travel through the candle up my ass.
I wind some thick tape around the base of the candle to prevent total insertion, pull up my pants and go for a ride on my bike. I look for a bit of rough ground and feel the vibrations up my ass. I usually arrive back having shot my load.
If you can find a flexible foam (Like pipe insulation) , they are vey long and you can cut them into smaller lengths so you can use them better. Just put some lube on it and it will slip right in. Then you can decide how far you want to go. But take an enema before you do or you will have a mess on your hands (literally) when you take it out.
The h****rs in Southeast Asia (Viet Nam, Thailand) would push their fingers in a guys ass just when they felt like they were going to ejaculate and many of them told me it felt really great when they did that. I never had a hooker over there, but I have heard stories from a lot of my friends that did.
Oriental women would do this for the American soldiers to make them orgasm more quickly. I have never had that done by a woman that I was having oral sex with, but I am told by those who did that it was very enjoyable. By putting your finger in a mans rectum, you are stimulating the prostate which is a very enjoyable thing for a man. So yeah, I think men enjoy having their prostate stimulated during sex. Don't women enjoy having their "G Spot" stimulated? Same difference!