So anal sex has been my biggest fantasy for years now. My girlfriend has always been against it because her ex tried the old "oh sorry, wrong hole!" trick a few years back and understandably she's never wanted to try it since. That is until recently. We've always been honest and open about each other's fantasies and she's known how I feel about anal for a few years (I never have and never will force it on her), and a few weeks ago she had a dream where we were trying anal and she liked it! Now she's curious and wants to give it a try when we next see each other, eek! We're currently doing long distance but we meet up next week and I desperately want to get this right. I want her not to just give it a go for me but to make her absolutely love it, to give her the intense, body-shaking orgasms anal can supposedly deliver. So girls: Any advice on what I can do to achieve this? Other than not to rush her and communicate, all the lube etc etc? Is there a position/specific spot that feels good? Are anal orgasms even real?! Any and all advice would be welcome, thanks!
I've been in the same situation as you - had gone into wife's vagina & with drew & then the next time I went to enter her again, she said - wrong one. Seems I had started penetrating her butt without me realising it & she immediately pulled her body away from hers. Just make sure you use a condom during anal penetration. All the best Jake on your upcoming anal endeavour with your partner.
Progress slowly, and be attentive to changes in her body language. Lubricate, Lubricate, LUBRICATE Plenty of gradual stretching beforehand. Usually, its easiest if shes already had an orgasm for the rectum to be receptive of penetration. Communicate continually, you can never ask too much if she's okay or hurting from the amount of stimulus. Did i mention lubricate?
Lick it before you stick it! Use lots of lube.. Stick your fingers in there first to get her used to the feeling. That could take a few days though as it can be uncomfortable. You should try it for yourself, you'll get a better understanding as to what feels good and what doesn't. I find the missionary position is the most comfortable to start off in. Don't take your fingers or cock all the way out once it's in, I find that to be uncomfortable. Also, I like being kissed while doing this, distracts a little from the discomfort and makes it feel more intimate.