Message: How to Tell New Boyfriend I’m Anal Only? Pt. II
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.
Hi, I hope you don’t mind if I answer in the comments.
I think the bottom line is, I feel like I’m enjoying this way too much. I’m a bit conservative, I had very romantic ideas about my first relationship, how I wanted to give myself completely to my first boyfriend, and in a way, I did. But he made me discover sex in a way I didn’t expect at all, and now I’m confused.
Take my relation with my boyfriend: I told him what you told me to say, that he could have oral and anal with me as much as he wanted. I said that because I was scared he would reject me. He took it literally: he can ask for a blowjob or take me into position for anal without warning, out of the blue. Sometimes, I’m not into a sexual mood at all when he asks that, but since I promised, I’m doing it… and I always end up loving it. And by the time he cums into me, I’m really hot, and I want more. I feel like a slut, and I feel weird about it.
I’m very attracted to the idea of this threesome. I loved sex with my ex, I loved the way he directed me and always gave me instructions and explained stuff to me, up to the way I should ache my back, or moan, or smile. My boyfriend is new to anal sex, and probably needs advice and direction I can’t give, my ex can probably change that. I’m fantasizing about this threesome ever since my boyfriend suggested it. But I’m scared they’ll think I’m just a slut, and I think I’m even more scared of loving it.
Maybe my body has accepted anal as the right and normal way to have sex, to the point any contact with my pussy gives me anxiety, but part of my mind hasn’t accepted it. Maybe I should trust my boyfriend and ex more. I don’t know.
About your question: he suggested they’d try to both take my ass at the same time. I’ve had anal very regularly for one year and a half and it never hurt, and I adapted very well to my boyfriend’s “jackhammer” way to fuck, so maybe I could do it, I don’t know. He said they won’t insist if it hurts, but I wondered if there was any precaution to be taken.
I’d love to have your opinion.
It sounds like you’re mostly concerned about liking sex “too much” and worrying that makes you a slut or that you’ll be judged as such by your boyfriend and ex. The reality is that it’s normal and healthy to enjoy, love and crave sex, and it’s society that puts ideas of being a slut onto women as a means of controlling those normal urges and desires.
You mentioned that you always end up getting turned on loving sex whether you’re in the mood when you get started or not. That’s not a bad thing, it shows that you have a high level of sexual adaptability and can be very compatible with partners who have a high sex drive.
I think you should trust your boyfriend and ex and give them the benefit of the doubt. If the idea of the threesome appeals to you, agree to it and give it a try. If you end up not liking it, you don’t have to do it again, but it sounds like it has a lot of potential benefits for you to explore, and if it helps your boyfriend learn from your ex, that can be good for everyone. It sounds like they both want to do this, and if you do too, I don’t think you need to worry about them thinking less of you for agreeing to it.
It definitely sounds like your body has accepted anal as normal and natural, but what part of your mind hasn’t accepted that, and in what way?
I agree this could be a great opportunity to try and explore double anal sex with the two of them, and that can be a very incredible experience for women. If you’ve never experienced pain from anal sex, it sounds like you’re very naturally well suited to anal, and probably could do double anal with little trouble as well. If you have any dildos, you could try and practice with two of them at a time, or you could insert one while having sex with your boyfriend. If you don’t have a dildo, try inserting some fingers in your ass alongside your boyfriend during sex. This can start getting you used to a larger stretch in preparation for both of them in your ass. Be sure to use plenty of lube when trying double anal. Otherwise, just start slow and relax around them and then have them start to pick up the pace and find a good rhythm.
So, in summary, my opinion is that if you want it and they want it, you should try it and see what it’s like. If everyone enjoys it, consider doing it more regularly. If it doesn’t work out as well as people hoped, thank everyone for trying and at least you know what it was like to try.
“…but since I promised, I’m doing it… and I always end up loving it. And by the time he cums into me, I’m really hot, and I want more. I feel like a slut, and I feel weird about it.”
Reading about your AO development has been a treat. If I could provide some input, it’s that I think with all this anal and oral anytime you’ve promised your current boyfriend, it’s changing your body and making you crave more. It’s perfectly natural for women who enjoy anal sex to feel slutty and although you have these romantic ideas of a relationship, it’s okay to expand your sexual identity. Embrace being an anal slut. What could go wrong with your ex and your current boyfriend having sex with you? They both seem to be very interested in your sexual wellbeing. Both know not to touch your pussy. I think you should give it at least one try so that your current boyfriend can learn different ways of engaging in anal/oral from your ex as well.
I remember being younger and just wanting to jackhammer girls’ assholes, but not every girl could take my cock like that. I’m like your current boyfriend – larger, thicker than most. My favorite thing is to jackhammer her ass in doggystyle! Trust me when I say this: your ass was meant to get fucked. If you can take a man reaming your ass and giving many blowjobs that include throatfucking, you might as well try double anal with a second guy you trust to see if you’re into it. Being throatfucked and assfucked at the same time might be a sensation you might want to explore.
I’m glad your ex taught you about ass to mouth. I think most AO men expect it, that’s true, but many times it doesn’t happen because women form a mental barrier. The anticipated “dirty” taste and smell isn’t what they expect once they get up close with their own nose and tongue. I had a fuckbuddy tell me she wanted ass juice on my cock every time she gave me a blowjob. So sex with her was always anal first, then oral. Getting hard just thinking about it….
So was that an easy transition for you to suck cock out of your ass? Is it something you liked immediately or became accustomed to for your boyfriend?
I agree with analonlylifestyle, you should try it and see if you like it. I can tell you both men will be very pleased by you embracing your slutty role.