Is there a more awkward conversation to have with your lady than finding a way to uhh The gritty details of the act don't exactly lend themselves well to being talked about over dinner. But you can't just try to slip it in when things are getting hot and heavy without asking, either. No seriously, don't try it.
So, how do you successfully gain access to that other hole? Whether or not you're granted permission to enter is really all about the ask — as proven by these ten ladies who said yes to their men after they framed their requests like this. Read on for the scenarios that sold them on trying anal. Then he went on to assure me that he'd stop right away if I didn't like it or if it felt uncomfortable — that he just wanted to try it once, and if I hated it we never had to do it again. He made it so that I had no reason to say no.
He made me view him as someone who I could see myself with for a while, and because of this I was comfortable enough with him to give anal a try. As it turns out, he just wanted to have his ass cake and sext his ex-girlfriend too. But I don't regret it. When he brought up that we could try anal, I wanted him so bad that I said OK, and actually really enjoyed it!
Once we tried it a few times, I actually really enjoyed it and even had orgasms! We worked it into our sex routine. So when he suggested that we try anal, I jumped at the chance to try something new with him. It also didn't hurt that he promised to give me an intense back rub afterward. By the time we actually did it, I felt like I was a butt sex expert, even though I hadn't gone through with it yet.
When my boyfriend asked if I would ever consider trying it, I said I would have to be really drunk. Five rounds of tequila shots later, I cashed in my butt sex v-card. I figured, if this guy knows how to perform open heart surgery, he also probably knows how to correctly execute anal sex without complications.
I don't mind being a little adventurous and he asked me if I'd be open to trying it sometime. He said that he had done it before and really liked it, but he didn't put too much pressure on me about it. I've had guys try to do that 'whoops, sorry wrong hole' thing in the past, so I just appreciated that he wasn't a total dick about it.