Well out of no where after our 17th birthday. She wanted to try anal. Now I need advice for getting there and actually, well, doing it. Also what can I do to make sure she enjoys it and doesn't feel pain? And best positions, etc.
I think doggy style is best. Use a finger or 2 first. Spend time getting her warmed up and ready for it. Make sure you use a lot of lube both in and around her anus, as well as on you. Most importantly, though. When you start to enter. Go very very very slow the first time you ease it in. Maybe just kneel there and DON'T move, but let her push backwards onto it so she can go at her own speed. It hurts sooooooo bad. Just be very gentile and listen to her and let her be in charge :)
You need lube. Like put it on your dick, and have her lay on her back and then put it in. I think that is much easier. I mean hey its yalls first time so take it slow oh yea DON'T just like put it in quick NO NO NO NONO don't do that because that will hurt sooooo bad put it in nice and slow and then do ...you try to lean over towards her but keep her legs in the air! But relax and you will do just fine!
I find using johnson's baby oil is better than lube. Also, the first time you do it go really slow (Once she gets used to it, you can go a lot faster) Make sure you get her really relaxed by kissing her, using lube/baby oil and some fingers (starting with just one) first to get her used to it, maybe try fingering her at the same time that always feels nice. I would recommend doing it in the bath, you don't need any lube and it feels a lot nicer and goes in better. Maybe light a candle in there next to the bath, the heat will make her relax her muscles a bit more. Doggy style is probably the best position to start off with. But my favorite is man on top, with my legs up.
Anal play can be very enjoyable. I know couples that enjoy it immensely. First, make sure you have lots of lubrication and use a silicon based lubricant (gun oil and eros are two good ones). You can also massage around the anus with a finger to help relax and stretch it out since your penis will typically be much larger than a finger.
Then go very slowly. If she tells you to stop then make sure you absolutely respect her wishes. Once you are inside I would recommend just staying still for a bit. I always had a tendency to want to start pumping like I would during regular intercourse, but that might be too painful for her. Make sure you follow her direction.
Finally, make sure that you use a condom and that you never enter her vagina directly after being in her anus. The bacteria from that area can give both of you urinary tract infections (just think of Tom Hanks in the Green Mile).
I can't tell you how many times I have told this to people. As I was retyping it yet again, I saved a copy, Here's the basic schtick.
Use too much lube, if you don't have lube, don't try this, you will likely be sorry. Use thick lube made for anal sex like Maxus or Probe rather than the standard sex lube.
Be patient, good anal sex requires warm up. I strongly suggest the recipient has come at least once prior to attempting anal sex.
Pain is telling you that you are doing something wrong, believe it, slow down and see what needs to change.
The use of fingers isn't to "stretch out the ass", it is to stimulate the second, inner sphincter (which isn't under voluntary control (although "bearing down" like you are trying to void the bowel actually helps open the sphincter). It opens due to pressure on the other (inside) so a little pressure that mimics the pressure it normally experiences to open helps a great deal. I suggest using lubed fingers for 15-20 minutes before you get started on the anal, you'll be glad you did. I generally warm up the area by using just the pad of my thumb to dip slightly into the ass, this also encourages it to open.
The "I need to poop feeling" is simply because that is what you were doing every other time these nerves got stimulated. What you wind up doing is creating a whole new set of tapes to go with the stimulation of this area. I would suggest clitoral stimulation in addition to anal stimulation to make the connection more concrete.
The secret of anal sex.
The anal canal and rectum isn't straight. The anal canal points toward the belly button for the first 2" or so and then switches directions and points toward the small of the back. Going straight in will cause you to hit bottom a few inches in. What you need to do is then point the cock toward the small of the back. My favorite way to do this is have the woman doggy style but her shoulders are on the bed. This points the cock at the small of back.
At the other end of this, most women I know who have tried anal sex successfully love it. It gives really powerful orgasms, especially when combined with clitoral stimulation