Anonymous: Hi! I wrote to you four weeks ago, I think. I’ve been taught about anal sex (and sex in general) by my very first boyfriend (we only did anal for the whole time, for a year and a half), then we broke up recently (not because of sex). I’m dating a new boyfriend, but I discovered that the idea of vaginal sex scared me (just him touching my pussy through my jeans gave me anxiety), and I didn’t know how to tell him I wanted to continue having anal sex only. Because of this, I only gave him blowjobs, but he was growing impatient for more, so I asked your advice, which you gave. You asked me to let you know how it went, so I’m writing back.
Just after I wrote to you, I thought I was an idiot: like I told you, my ex introduced me to anal sex by saying he was scared of pregnancy but didn’t want to use condoms or other contraceptives (I keep thinking it was an excuse to get me into anal, but whatever), so the solution appeared to me: I just had to use my ex’s excuses!
When I started explaining this to my boyfriend, I got very nervous about his reaction, I was afraid he’d think I’m a slut, so I added what you advised me to say: that I’d love to do anal and oral with him as often as he wants, and that he can have anal sex with me all the time and cum in my ass without any fear of pregnancy.
I was scared he’d reject me, but he smiled broadly, said he didn’t expect this at all from me or my ex (they’re good friends), then he hugged and kissed me, caressing my ass. It was a huge relief to feel his hands on my ass and not my pussy: you have to know I chose not to experience sex by myself, I wanted to discover it romantically with a boyfriend, and my ex never touched my pussy, so my genitals basically never received any sort attention.
We made love right away, and it went well. My boyfriend’s bigger than my ex, and he’s much rougher when he fucks, but it didn’t cause me any trouble, my ass adjusted very well to him. At one point, I felt that I was a little dry, so I did what my ex taught me to do: I pulled out, then I sucked his cock to lube it up with saliva. This drove my boyfriend crazy: he swore loudly, then grabbed my head firmly and started fucking my throat while calling me names, then he came with a lot of cum down my throat. It’s a good thing my ex taught me how to handle this (he did it pretty often), or I would have choked for sure.
He later apologized, he said that me sucking his cock after it’s been in my ass caught him off guard. This surprised me, since my ex told me any guy into anal sex would expect this, that it was just normal behaviour.
Anyway, we’ve been having sex very regularly since, and everything is going well. My boyfriend explains much less things than my ex, he’s not licking my ass at all, and he’s always fucking me doggy style, but I really enjoy sex with him.
Yesterday, though, he surprised me. He told me he talked a lot with my ex since we started having sex, that they shared their experiences, and it brought them a lot closer. Then, he asked me if I’d be OK with a threesome.
Like I said, I’m a romantic, so I was a bit shocked, I didn’t know what to say. He said he’d let me think about it. On one hand, I’m still shocked: I’m his girlfriend, and I’ve only had two lovers so far, so getting into threesomes now somehow hurts my values. But on the other, we’re all quite close, and I really loved sex with my ex. Besides, my boyfriend is less experienced than my ex, so maybe a threesome would teach him a few things. And finally, I’m not comfortable with the idea of saying “no” to my boyfriend: after all he’s my boyfriend, and I told him what you advised me to say, that he could do anal and oral with me as often as he wants – what if he’s disappointed?
What do you think I should do? I’m confused.
My boyfriend told me that if I’m OK with it, they could try double penetration. Do you have any advice?
I’m glad to hear that things worked out well for you and that your new boyfriend accepted you being anal only. It’s great that you’re able to enjoy anal and oral sex together without having to worry about him trying or wanting vaginal sex, and I’m sure he’s very happy with the arrangement as well!
As for a threesome, it really comes down to whether you want it or not. It sounds like part of you does while another part does not. I can’t really tell you what you should do in that case, you’ll have to reconcile the two halves of yourself and decide what will be best for you. Will having sex with your ex boyfriend along with your new boyfriend ultimately cause tension in your relationship, or will it bring you all closer together? Do you want to explore multiple partners or do you strictly want to stick to one partner at a time? Sex with multiple partners can be a lot of fun for some people, while other people don’t like it. And while some of that may come down to experimenting and figuring out whether you’ll actually enjoy it or not, some people just aren’t interested in even starting, and there’s nothing wrong with that.
When you boyfriend suggested the three of you try double penetration, what specifically is he referring to? If he means they can have anal and oral sex with you at the same time, that can definitely be something fun to try. If he means they can have double anal sex where they both penetrate your anus together simultaneously, that’s definitely a more advanced activity but a lot of women love how it feels and say it’s much more intense than just regular anal. But, if he’s suggesting one of them penetrate your anus and the other your vagina, then that wouldn’t be anal only and I wouldn’t suggest doing that nor would I expect that you want it. If that’s what he means, I’d say you aren’t interested in double penetration.
Hope that helps, and I’m sure we’ll all be interested in hearing what you decide to do and how things progress! Good luck.