Advice for anal stretching/preparing for anal sex

I want to start preparing myself for anal sex. In other words I want to stretch myself enough so it won't be difficult for a man to penetrate me, either on him or myself.
The problem with dildos is I can't find a comfortable position to hump one for more than a few minutes, and it's an uncomfortable angle for my hand.
The problem with buttplugs is gas can build up so you can't wear them too long.
So what I'm thinking of getting is something that will expand me without sealing me off lol. Here are some links to some dilators I'm considering getting. Can I ask you guys your opinions on these? Maybe you have some other suggestions?

• BDSM type dilator: My top choice so far. Made of metal. Offers most dilation. Doesn't need lube. Can fit a fist in case I want to consider getting into something really kinky. (Yes, I know this will not happen overnight.) Takes awhile to adjust. The six pressure points might not do a good job of spreading the pressure of the spread.
• Tulip looking dilator: No adjustment. Pressure points are spread out over more of an area. Might be difficult to pull out because its natural state is expanded. Outward pressure might erode over time.
• Speculum: Only one adjusting screw. Goes in easily. Expands only in a V formation. Possibly just for vaginas?
• Hollow buttplug design or another one or metal one: Stays in shape (I assume) but can't increase in size. Moderate to slightly difficult to insert and remove.
• Spool looking dilator: Minimalistic buttplug. Also keeps shape but can't increase in size. Probably best for wearing in public. Expands sphincter but keeps rest of anus tight. (Is this desirable?)
• Anal chastity device: Metal. Pressure points are spread out. Added use in BDSM activity. Most expensive. If the key is lost I'm screwed...or rather not screwed lol!

I prefer to get something that's expandable as I loosen up but not too interested in anything inflatable. Aside from being restrictive they break down easily. I know from experience.
I don't plan to leave the house for long periods of time with anything in me, but would consider leaving something in for short trips, both to make time and honestly the idea of having something inside me while no one else knows is kind of kinky to me!
Buying more than one is also an option for me.

 

We are all different, so what suits/stimulates one may not work for another, so I would hesitate to give advice. Best is a good top with a medium(?) size cock who will spend time entering you.

Some of those you mention are real expensive and hard to insert as a novice...esp the hollow butt plugs.

When I was younger and getting into bottoming I just practiced with a few different size regular dildos, plenty of lube and took time. Tho saying that tge first guy that fucked me at 19 had an 8" uncut cock and while he took it slow, it was my first and I know that by the time he came I was pushing back onto him.

Nothing better than a live cock.......

Simon

 

Thanks for the perspective. It seems the best way to do this is just go for it. I guess I'll know when I get there. I hope to have intuitive, considerate fuckers!

 

If you don't already, a dildo with a good suction cup can help save your hands and you can play around with the angles and positions. Also, you might want to warm up with a finger or two for a few minutes before going right to the dildo. Myself, I find that more comfortable. Finally, you could try to find an angled depth probe vice dildo so that you can gradually build up without having to get several different sizes of dildos.

 

I have several toys. When I first started playing with them, some were difficult and a bit painful at first...and today...I look at those same toys as being laughably small.
I can take a small fist now that my toys have grown over time and I know how to relax my hole.

My advice...get a small plug and a dildo that you think you can handle that has a good suction cup. Use the plug with plenty of lube and wear it for as long as you care to. The objective is to get your hole to relax around the thickness of the plug. Wear it for an hour, take it out and then use your fingers to feel how loosened up you are.

Stick the dildo to the tile in your shower and pretend it’s a Top waiting on you to bend over. Back up to it and push back letting it ease inside you. You’ll be slapping your ass against that tile in no time!

Then...you just buy bigger toys!

Learn how to properly clean yourself out also. Very important!

 

You don’t really need all these toys just use your fingers some technique and lube all you want to do is loosen your sphincter muscles temporarily before Intercourse anything beyond that is masturbation

 

I just a series of butt plugs. I have 3 sizes the graduate from small to gaping. I really have never needed to use anything bigger the the smaller one before getting a hot beef injection. I don't want my hole to be too dilated.