Trouble with Anal - Need some help

[D_Tam_Ponds]

So, this guy I have been seeing kinda casually has been pressuring me about doing anal for a while now, and I had him just about convinced it was never going to happen. Then this last week, I have been really extra adventurous and hot and I told him I wanted to try it if he could be slow and gentle - which he is, so I wasn't really too worried about that. He was so excited - to say the least. So we started out with him rubbing around my ass while I was giving him head, which quickly escalated into him fucking me with a large dildo while he had a finger in my ass. I was quite shocked to find that it was really enjoyable, and the combination had me in a deep orgasm fairly quickly. Then we had the best sex I've had in a long time - I was really able to open up to him and I had 4 more orgasms riding him cowgirl. We ran out of time, but agreed we'd get back to it after we did what we had to run out and do.

So we did, we got back to my house and after about an hour, he jumped in the shower quick, and then we got restarted with me giving him some more head. I was turned on, but less so this time. We moved into doggie position and had some vaginal sex that way, which was really getting my head back in the game, and he got the lube out and started again, rubbing and fingering my ass - again it was feeling good to me. Then he pulled out and went to try to push himself slowly into my ass. He kept applying lube, and I was trying hard to relax and want his cock in me this way. He got in just a little. He has a nice sized cock - but it's not what I would call large. It was just so tight, and he just couldn't push it further. With all that lube, it still felt like there was none at all. I continued to breathe and try to invite him further inside. It was altogether pretty unsuccessful, and I ended up bleeding from my ass a little for several days. In a way, I sorta crave more, but how do we get this to work? The lube we used was I think ID Glide - water based. Hmm - and how soon should I assume I'm "healed" and try again? Or should I throw in the towel? I think I would be happy just being double penetrated with a finger :*) but somehow I'm sure that's not going to do it for him LOL

 

[helgaleena]

Let him continue to play with your ass with finger and lube. The main thing is to enjoy yourself. It may well be that he enjoys knowing that your opening is 'too petite' for 'gigantic' him... if you really still enjoy the sensation, it is possible to work up to bigger penetration with gradually larger toys.

As for bleeding-- anal sex is a sovereign remedy for hemorrhoids. They are varicose veins of the rectum. Bleeding can come from such a condition as well as from rectal trauma, and the remedy is to rest them and then resume your normal activity. What that 'normal activity' consists of is up to you!

As for lubricants, every person has favorites, whether oil based or water based, commercial or herbal/edible, so just experiment. Beeswax and olive oil melted together into a salve consistency is my personal favorite.

 

[joeweekend]

Don't use water-based lube. It's that simple. Stay away from the stuff - it dries out, and is guaranteed to leave your ass feeling raw.

If you're using a condom, lube with silicon based lube - ID Glide Silicon (read the label to make sure that's what you're getting!) is awesome stuff. Gun Oil's good, too. If you're not worrying about using the right thing with a rubber, go with Vaseline, or Crisco (don't laugh - it's an awesome lube).

 

[noyoucanttouchit]

Sometimes you just can't relax enough to allow safe penetration. (The asshole has a mind of its own!) Either spend more time with massaging the hole with a finger or small toy, a little more foreplay, some SAFE rimming (hello - Saran Wrap!), or just forgo poking the south end of your northbound partner and try something else.

 

[derk19]

Take your TIME!!!! It took me two years (no lie) to get into my partner. Lots of lube and lots of patietnce. Itw as worth it in the end.

 

[D_Tam_Ponds]

I'm happy to report that it is now a go, thanks to you guys' suggestions. I think he may have turned me into a monster hahaha - how am I ever going to find nice big cocks for BOTH?! ;*)

 

[D_Ezdras Dingledonger]

I nominate myself, but then it's just like me to say that.

 

[ThongerDude]

Darwinlilly, try some rimming to help you relax. Jump into the shower and make sure you're both clean and then have him rim your ass. It really helps you relax and it feels amazing. It feels really ticklish and makes you feel hotter and you'll really want to take him after that. If he won't rim you, rim him first to let him know how good it feels. Once he realizes how much pleasure there is in that, he'll hopefully want to rim you too.

After the rimming, the fingering and toys will help expand your bum hole further. Once you do all that, try some oil based lube and hopefully he'll slide right in.

PS: Fair is fair, so try using the dildo in his butt along with the rimming and fingering. He'll love it. He may not know it at first, but he will.

 

[D_Tam_Ponds]

I don't mean to sound dumb here, but I'm really not sure what rimming is exactly - I have an idea - though for sure hahaha. Boys HAVE created a monster!

 

[ThongerDude]

I don't mean to sound dumb here, but I'm really not sure what rimming is exactly - I have an idea - though for sure hahaha. Boys HAVE created a monster!

Darwinlily, rimming means licking of the ass. Don't let preconceptions get in the way. Have an open mind about it and give it a try. It's the most pleasurable feeling in the world having a tongue licking there. To get started, just run your tongue up and down his crack for a while and see if he likes it. If so, then run your tongue around his asshole. That will drive most guys crazy! If that's the case, then press your tongue slightly into his asshole and see his reaction. Of course, all this is done right after a shower!

You should get him to try this on you too. You'll love it.

 

[D_Tam_Ponds]

Ha - that's just what I thought it might be...

 

[big_tits4big_dicks]

I like to lay on my side to start. Then I'm in control of pressure. Then I just start really slowly, and use a silicone based lube. I swear by that stuff.