For those that have anal and took a while to get used to it i am just wondering what position you did first?
A lot of people seem to like doggie but i would think cowgirl or reverse cowgirl would be better so you can control the depth?
I couldn’t do doggy for my first time. Eeeek for me, it was way too painful. I actually did it from spooning, made it sooo much easier.
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How long did it take you to get used to anal penetration?
Hi @ValleyCouple
I find that doggy allows for deeper penetration and for the giver to be in control - this isn’t great when starting out.
Personally I would recommend cowgirl as you get used to it so that you can be fully in control and take things as slowly as you need to.
I had to start with small toys and work my way up.
Remember lots and lots of lube to help 
It has actually taken us years to finally get there.
Used to hurt so much, it just put me off trying for a very long time, until quite recently.
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After we had been playing with smaller toys for a while and I was ready to try anal sex, we did do it in doggy. Mainly because I find being on top uncomfortable on my legs ( I didn’t want to collapse onto him if my knees gave out!! Ouch! I found the easiest way to do it was for me to back onto him slowly, that way I could still control the depth. Also, I’ve found good communication throughout is really important. Just keep giving feedback.
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We tried a few different positions but the easiest for me was on my back in missionary. I didn’t think it’d work but it made things a lot more comfortable.
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My first time was in doggy but I agree with @ChloJakes that spooning would be a lot nicer and relaxing to ease into. We do a lot of anal play and cow girl is always nice too but when it gets too much in doggy we always spoon as its less lingual in that position. Good luck remember lots of lube and warm up fun with fingers and toys!! 
We do doggy and standing up anal but for my Wife she prefers anal cowgirl, it was the first position we tried and still our preferred. She takes control of everything, the initial penetration, speed, depth and also how much pressure she puts on her clit as it grinds on my pelvic bone. It guaranteed orgasms for her.
For me when she’s pegging me its doggy, I like her to have complete control, we have a curved G-spot strap on and it’s great for stimulating the P-spot. 
X
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I have just bought some new toys and a douche. Will be starting some anal play this week.
What do females find makes them cum the most when it comes to anal?
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When we first did anal it was face to face with my wife’s hips raised up on a wedge cushion. I wanted to be able to see her face so that I could tell that she was in no discomfort. Nowadays she prefers doggy so that’s what we usually do. We haven’t tried cowgirl.
For pegging we followed the same route except that I do straddle her in cowgirl (boy) occasionally. I prefer being pegged in doggy as I love the role reversal and domination.
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We started in doggy position, but as mentioned above the taker then isn’t in the driving seat so to speak. Trust and communication is massively important.
A piece of advice I was given (and pass on) is if it stings, stop. Ask the giver to stay still, dont pull out just hold still while you get used to it. This worked for us x
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It took a bit of playing with toys before I was confident enough to try anal sex with my OH. About 2 months I think. Definitely take your time warming up to it if you haven’t tried any anal play before. Once I did get to the point where I felt ready to have anal sex with my OH I really enjoyed it and didn’t find it difficult or uncomfortable at all. I wondered why I had waited so long! We usually warm up with small toys during foreplay but I don’t always feel I need to - sometimes I want that sudden stretching feeling without working up to it but I wouldn’t suggest this until you’re both confident.
As for what I find pleasurable - for me it’s the sensations around the entrance, there are so many nerve endings around the anus that playing around there sends me crazy! I love the stretching sensation too. Personally a lot of the excitement is mental - there is something primal about being “taken” in this way. I don’t orgasm from anal penetration (or vaginal) and need some clit stimulation from fingers or a vibrator. Anal play / sex is a regular part of our sex life now, I find it’s one of the only things that gets me really turned on without fail!
All of that aside, there are lots of people who just don’t enjoy it or the idea doesn’t appeal at all and that is ok too. I’ve answered all of this on the basis that you’ve discussed this as a couple and decided that it’s something that you’d both like to try. If not, please make sure it is something you both want to try 
I tried doggy first time round as I found it’s not only an easy angle to get it in but also that you are able to open yourself up the most to get it in more easily if that makes sense as you can spread your cheeks. x
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