(NSFW) How do I loosen it up?

The same thing happened to me when I first tried it with my ex. It hurt a lot and I did see some blood on the toilet paper. Not a lot but just a little.

Also if it’s your first time, it’s going to hurt because you’ve never done it before and it’s a tight area.

They say the best thing is to be relaxed…. practice makes perfect.

I would say to really get into the mood. Foreplay, take your time, and feel relaxed about the whole thing. A lot of lube can’t hurt either.

Find the right positions that you and your partner feel the most comfortable in. Good luck.

You can work your way up.

Just relax and keep trying, slowly but surely. You can use some toys and plugs, smaller then go bigger once you feel a little looser.Hope this helps.

any suggestions on good positions that work well for this? We tried it doggy.

Also its like my third time trying it, but the time between each of them were quite long

Definitely not doggy, but that is just my own personal opinion from experience….

My ex was really well endowed… uhm, really well endowed lol. So it hurt. But the best positions I found were missionary… but that was between me and him.

With you and your guy, you could like other positions.

I think missionary is good for anal.

Oh ok, I see. The first time I did anal with my ex, we literally went right into it…. probably not the smartest thing lol. I don’t even think we used lube o_O anyway, he did it first doggy, which hurt, then we switched over to missionary, and it felt really good by then….

I was really surprised at how comfortable and pleasurable it was. I didn’t like doggy though.

My ex had a 9 inch penis so I totally thought it would hurt and be unbearable… but it wasn’t :)

Wow. Yeah, he is average to above average so hopefully that will work. Thank you!

No problem :) good luck. I’m sure there’s lots of things on the internet/videos too with more information.

Gay men sometimes use amyl nitrate poppers to relax the sphincter muscles before engaging in anal sex. Poppers are technically legal here and can be purchased over the counter. You’ll need to check whether they’re legal wherever you happen to reside.

Also, but this is more of a general thing, you can find inflatable dildoes/buttplug, which work well if you want to practice slowly. That aside, the suggestions given so far are very good.

carrot

Maybe this isn’t your thing, but smoke pot first! It’ll relax you!

A few suggestions, since I’ve looked into this a few times. First, it really shouldn’t hurt the first time if you do it correctly. Unfortunately, going right at it is not ‘correctly’ (YMMV, naturally, depending on your kinks, but I’m going to assume pain’s not a goal here). I will definitely second @partyrock‘s and @Thammuz‘s suggestions of plugs, that’s the best idea. I would suggest a smallish and medium flared one, and practice with those. Do it when you’re relaxed and with lots of lube, and you shouldn’t have any pain. If you do have any pain, stop and use more lube and possibly check the angle. Within a bit you should be comfortable enough with the level of stretching that you can have anal sex again with your partner with no trouble.

Also, though again YMMV, i wouldn’t personally suggest poppers and certainly not pot, and that’s with legality issues aside. Poppers may be safer then I expect, but in general messing with your body to have anal sex is usually not a great idea. It’s a rather delicate area and things that mess with muscle control are usually not good. And pot doubly so, because it’s going to mess with your head and make it harder to deal if something goes wrong. You may not realize you’re in pain, or simply ignore discomfort, etc, that may tip you off otherwise. So, personally, I wouldn’t suggest it. But again, YMMV.

As far as position, I’ve done it in missionary and that worked quite well. I haven’t tried doggy yet so I can’t comment, but missionary is a good one, though a pillow under your butt may help with the angle, since it’s a bit different, naturally.

@Hypocrisy_Central is there much of a difference in advice? Assuming I’m even understanding your slang, which I may not be.

Have a few drinks.

I highly recommend him giving you a ginormous orgasm first…it helps, a lot.

@BhacSsylan is there much of a difference in advice? Assuming I’m even understanding your slang, which I may not be. Being tight up front, takes different methods than being tight in back. Sometimes toys for one can be used to help in the other, so “that area” is rather vague leaving me to guess, and that guess could be wrong, then any advice would be no better.