I’d Like To Fuck Her Ass

September 23, 2009  |  dirty stories

Since we got together about nine months ago, Kristen and I have kept a verbal running list of Sex Stuff To Explore (okay, not always verbal, we have a shared Google doc, too).

Up pretty high on my list, and one thing that I have mentioned quite a few times, is that I’d like to fuck her ass.

I’ve never actually strapped on and fucked a girl up the ass (how come it’s up the ass but in the pussy? Does one say “up the pussy”? No, that’s awkward. Weird). (I have actually fucked a guy that way, but perhaps that’s different. Or perhaps that’s too much for a lesbian sex blogger to disclose in parenthesis without going farther in depth. Carry on.) I want to. The idea is really hot. I don’t know why exactly – not that the why matters terribly, but perhaps if I could articulate it better she’d be more inclined to try it. Maybe because it’s taboo, maybe because it’s tight and I expect the sensation to be a little different, maybe because I have fantasies of sharing her with another butch (or two) as we all fill her and use her, so she needs the practice. Maybe because DP feels good. Maybe because I know it changes and enhances my own orgasms. Maybe because I know it makes her nervous.

I guess the real hangup is that it makes me a bit nervous too. I don’t have trouble pushing her to do things I want that are things I’ve done in the past, even when she’s nervous, but for some reason we still haven’t done much ass play. Sure, a finger here and there, a small butt plug a few times – but I want it to be my cock, and I want to be wearing it.

I’ll admit, too, that since I started keeping a tumblr log and going through my dashboard as another daily inbox, I’ve thought about it more often. There is no shortage of cock-in-ass shots on that site, the sights of which makes my own imagined cock strain against my slacks every time.

Sidenote: why the fascination with girls assholes, guys? Same reasons for mine, I imagine …

Kristen mention Tristan Taormino’s book The Ultimate Guide to Anal Sex For Women the other day, asking if I had it. I don’t. I may attempt to hunt down a copy though, and maybe a DVD or two of hers too. She does, after all, have a butt plug named after her.

I may be getting a Fun Wand from Babeland in the near future (crossing my fingers), which I think will be great to play with. I’m tempted by the Njoy Plug also – I have the Pfun Plug, perhaps I should get that out. (I am a bit obsessed with these stainless steel Njoy toys these days, thanks to my Pure Wand.) I have plenty of other butt toys, though – goodness knows I have no shortage of toys. Slim cocks I anticipate working up to, butt plugs in small-medium-large, thicker, wetter lubes. No problem.

Something still makes me a little nervous, though. It isn’t the shit part, at least not for me – I don’t particularly like it, but it is just part of the reality of things up the ass, and whatever, things happen that are sometimes awkward. I can deal. I know how to clean it up, know how to prep with towels nearby and condoms and wipes and whatever other supplies. I’m not sure what Kristen’s hesitations are exactly – inexperience? pain? shit? – but perhaps it’s time to ask her again.

Fucking up the ass strapped on seems like something that is done for her pleasure, not mine. It’s her body that has to get used to some new invasion, some new and violating way of being taken. The top in me – and the use of a dick with no nerve endings – makes me hesitant to pressure something that is all about her.

But then again: this is a frequent topic for our sex life, actually, and a place in which we have some snags. Nothing big; a few tiny things. We have a complex power dynamic (aren’t they all) in that while I am a top, I am sometimes more of a “service top,” doing things to my bottom because I know she wants them, I know how she likes it, I know what she wants. (I could say much more about this – it is, in fact, the reason the Sugarbutch Star stories were born, and often the way I write smut too. That feels like a tangent, I’ll cut myself off.) Sometimes, as you can imagine, this extends out to me being so focused and attentive to her needs and reactions that I ignore my own. I think this is why (at least sometimes) I have trouble getting off. Likewise, it is challenging sometimes for Kristen to contain, to hold – not to let in or open, those are a bit different (I have an article on these concepts in the works) – and we’d both like her to be better at it. Playing with that concept sexually would be a good way to do so, we’ve discussed this, since it is one place where I can practice being completely focused on me with disregard to her feelings, and where she likes being submissive and bottoming to that kind of degrading, using power energy.

But why have I not connected this with fucking her up the ass before? I want to; I am hesitant because I feel like it’s “for her pleasure” and not for mine. But it is for mine, maybe not physically, but in other ways. Obviously! Weird to think I still have a small hangup there. This particular act it is a great symbol of this issue of me taking, selfishly, something for me and not necessarily for her (with, hopefully, the side effect of her liking it). I have pages more to say about this issue, really; I feel like I’m only scratching the surface, but perhaps I’ve written around it enough in the past that you know what I’m talking about.

Kristen, baby, that means you’re going to give me that sweet ass of yours, and soon. You’ll do that for me, right? I thought so.

Folks, Kristen reads the comments – leave some support, wouldja? Tell her being fucked up the ass is not that scary. Tell her it is hard at first but you get used to it. Tell her why you LOVE it, tell her why it’s fun and hot, tell her it makes your orgasms better, tell her your story of when you first tried it. Tell her it’s worth the work. Tell her your story of learning and practicing ass fucking. Lend her some support. Share some resources.

You know I’ll certainly appreciate it.

 


22 Comments


  1. It feels amazing and I highly recommend it! Giving or receiving that is along with rim jobs…

    Example A:
    http://www.enterbelladonna.com/images/samples/SD1

    xo

    Syd aka Shawn

  2. I just wanted to let you know that one of the most deliciously agonizing things I experience as a bottom getting fucked is when somebody has the patience to feed my ass their cock a centimeter at a time. Especially at the beginning, the slow but persistent push helps me relax. Also, I don't know if Kristen meditates at all but I would say that some practice with controlling her breath to keep it smooth and deep while you're teasing the shit out of her ass (no pun intended) will help. I'd say that one thing a lot of people expect when they're used to playing with pussies is that they can start going at it rough and hard right from the get go and it just isn't so. Firstly the ass does not self-lubricate (much to my dismay) and secondly the muscles there are much more accustomed to pushing things out rather than letting them in. You can still use and degrade while going slowly, you can definitely eroticize that interaction in a way that serves your power dynamic.

    Why do I love getting fucked? Well, one of them is the above mentioned release. Once your muscles have truly let go and aren't providing any resistance I get a feeling of deep satisfaction and accomplishment and relaxation. Some of my friend have called me a tight ass, but when I get fucked I can let that go a bit and really get into something that's outside of my normal life. I find that I'm frequently more playful, sexually, when I am or have been fucked recently. I am more giving. I feel more confident and sexier.

    I've learned a lot through trial and error and one thing is that there's no such thing as too much communication. If you even think of screaming "ouch" or "ow" you need to say something before your partner does something that does make you scream "ouch" or "ow" or even "Oh god I think I'm dying" – and not in a died and gone to heaven kind of way. Maybe you'll need to think about how you would communicate that in the moment, in the middle of the power flow that happens between you and your partner. I tend to have pretty vanilla sex so I usually just say something like "Slow down" or "Stop" or something, but if that doesn't feel comfortable because of the situation then you should give some thought to how you would express that. Pain doesn't mean you need to stop – unless you're blacking out or just plain not enjoying it AT ALL – it just means you need to adjust.

    If you're really worried about shit, I'd say get yourself a small anal douche bulb and use it about an hour or so beforehand to give yourself lots of time to get all the water out of your butt. Barring that, I highly suggest that you go to the bathroom beforehand. Even if everything else is awesome, I hate the overstuffed feeling that can result from being full before I even start.

  3. Perhaps there are activities that could help to awaken a desire to be fucked up the ass.

    (What I'm saying here, Kristin, is that you should make Sinclair give you a long anal massage: http://www.goodvibes.com/display_product.jhtml?id… – great DVD, and I was able to rent it at Good Vibes for $3)

  4. opps, I meant to point you to Vol. 2, Anal Massage for Lovers. http://www.amazon.com/Anal-Massage-Lovers-Vol-2/d

    But both are great!

  5. Oh Kristen. I've had good, and I've had not so good anal sex, but I've never had bad. Even the first time, two scared people trying something new on a single bed, not even thinking of lube, there was something that felt good to more than the masochist in me.

    It makes me feel dirty. It makes me feel strange. It makes me feel vulnerable beyond measure. It makes me feel giving. It makes me feel powerful, because only my ability to relax will let anything in.

    I don't come so easily. But with anal, I pretty much always come. It's a lot of things; the pressure; the hand I have on my clitoris, sometimes; the way, as I'm touching myself, he asks if I'd like a cock in my bottom now; the urgency I feel from him; the passion; sensing how much he gets from it.

    It's something you work for; therefore worth more. It's something rare, special, you are subject to the whims of your body: slower, gentler, stop. Now. Ready. All of you. I feel laid bare, exposed and truly loved in all my dirtyness and loneliness and realness and femaleness.

  6. Just wanted to chime in… I find myself in an interestingly parallel place: I both desperately want to BE fucked in the ass, and I'm also kind of scared of it.

    Sometimes when I'm masturbating, I'll use a vibrator on my asshole (not up it, but just on it, right outside), while my fingers are going at my clit. AMAZING feeling. Just amazing. The stimulation I get from the vibrator *always* makes me feel like I want to be FUCKED and NOW. The vibrating stimulation relaxes me, too, and makes my ass much more open.

    So, I've done a bit of solo ass play, but I'm kind of antsy now to make it a duo. Still, though, kind of nervous.

  7. let me start off with saying i had some of the best anal sex the other day with my lady. i love anal sex, we dont do it often, so when we do its a special treat.

    concerning the 'ick' factor. i always use the bathroom and take a shower before hand. but if you want that deeper cleaner feeling go for an enema.

    we never just jump into anal. always lots of foreplay. my lady also gets me off a couple times before she goes for my ass. i cant say i've ever been scared or nervous about anal, actually i think my girl is more nervous about hurting me then i am of being hurt on accident. but starting off slow and steady and working up to a good fuck is essential.

    i love the full feeling of being well and truly fucked up my ass. i like fingering my pussy while my girl is fucking my ass and feeling her cock sliding in and out. its just so different from being fucked in the pussy. its intense and i've had some of my best and most intense orgasms from anal.

    good luck! and have fun!

  8. my first anal experience was with a guy deciding he was going to fuck me in the ass w/o consultation, lubrication or acknowledgment of my protests. to say it was uncomfortable on many levels would be an understatement.

    over the years, anal sex would bob up in my consciousness, darkly, with something of a sickening thrill – i mean, after that experience, how in the world could i even think there might be pleasure there?! looking back, i think part of that was me needing to reclaim the power i felt i'd lost in my initial experience. take it back for me and make it what i wanted it to be.

    anal sex is certainly ripe with possible protestation points, but desire can easily make each of those manageable, if not minor.

    i may be imagining that i wrote a blog post about curling up behind my gf, working her clit, and then also one slick finger into her ass as i whispering a very detailed scenario into her ear about how i was going to fuck her in the ass before i ever did. i'm too short on time to dig it up, if it actually exists. in lieu, here is my post about our first time: http://tonguetiedblue.blogspot.com/2008/09/hearin

    it's hot because its sensations are so different – hot because it's so vulnerable – hot because it's taboo. orgasms during anal penetration are something both familiar and entirely different.

    best advice: plenty of slow, plenty of listening and plenty of lube!

  9. Just a few comments:

    Anal is my favourite type of sex. I am very particular about the dildos we use for anal though. I like a tapered end – so not one with a large head, as many of the realistic ones have. I would recommend something like this one to start with: http://www.edenfantasys.com/dildos/strap-on-dildo… (We don't use the vibe though, I just bought it for the shape and size).

    I've never really had a bad anal experience. The only time the 'shit' factor has ever been an issue was when I was coming down with a bad virus which affected my tummy and didn't know it. Otherwise, provided you've been to the toilet beforehand, you should be fine. Soaping just slightly inside the anus (making sure you rinse properly afterwards) might make you feel more comfortable if the cleanliness factor is an issue. The Taormino book might be good if you're nervous. I have it – my partner and I read it after we had had anal a few times, and while we didn't learn much from it that we hadn't figured out for ourselves already, if you're unsure it might be good.

    I actually have anal orgasms – so I cum when my partner is fucking my ass, without any other stimulation. They are the most mind-blowing orgasms – better then clit or vaginal ones, in my opinion.

    Another fave activity is having her fuck my cunt while I have a butt plug in – very, very intense and amazing. I kind of lose the plot a bit with it – it blows my mind.

    I think, apart from the astonishing orgasms, the thing I like most is the sense of complete surrender to my partner. I am handing a very sensitive and potentially embarrassing part of my body over to her entirely, and that surrender of control is what really does it for me, I think.

    Kris, if you want to ask anything about this privately, I'm happy to answer you – femme-bottom to femme-bottom (excuse the pun). I guess Sin can see my email address, even though it's not published here.

    Enjoy!

  10. "It makes me feel dirty. It makes me feel strange. It makes me feel vulnerable beyond measure."

    that about sums it up. but since you asked so nicely (and it's something i've actually given a lot of thought to) i'll elaborate.

    my ex was all about the ass. she loved asses, ass play, etc. so i tried it, very, very skeptically. and i didn't like it. but i do tend to adhere to "i'll try anything twice," at which point i really didn't like it, but with a burst of absolutely insane ecstasy at the end. the kind of scary, i actually don't know what just happened (what did i do? or scream?) kind. that, you know…made me a little more curious about it.

    as of the last time i was fucked in the ass (hmm, i do say "in") i still didn't *like* it, exactly. there is something about it that is so profoundly taboo to me – beyond the general ick factor, it makes me very uncomfortable, mentally – and it kind of hurts, in my experience. but i love it. confusing, yeah?

    i think it is a power thing. it's like the ultimate winner submissive thing for me. because it's something i really, genuinely don't want to do (as compared to pretending i don't want, or being afraid of, but wanting). but it is not something i don't enjoy. i don't, at first, but farther along…i don't think there is anything i've ever done that makes me quite that hot. it's the perfect example of "you'll do it, and you'll like it!" =)

    at least, that's how i though of it, but it's been a while. i'm afraid my girlfriend might not be pushy enough for this experiment.

  11. I love me some buttsex. Also, Always Aroused Girl writes about it so magnificently, I can't recommend her enough on this subject and others too, like fisting :D

  12. Oh, something else I should have said about dildo choice – the smooth operator one I suggested above also has a fair bit of 'give' in it, which is good because the anus isn't straight, but curves about a bit, so very firm dildos can hurt a little.

  13. I'll echo a few other people and say that, yes, when it's done right (slow at first, lots of listening to your body, and lube is love)- it's one of the most fascinating ways to have sex. The power dynamic, taboo and nerve stimulation combine to short my brain right out.

    THE most fascinating I've ever encountered is DP. A vibrating plug in my ass and her cock in me from behind had me screaming for quite awhile. The good kind of screaming.

    (Actually, I was a bit embarrassed later because we were in a hotel, but otherwise, a-MA-zing.)

    The embarrassment about 'OMG it's the ass' is easily remedied, and for me at least mostly subsided after the first time.

    I hope you give it a try and enjoy it, Kristen; I know that Sinclair will take good care of you.

  14. Yeah, what IS the thing with guys and ass fucking?? Your other posts got me all horned on…. but this subject always dries up the cream…

  15. Kristen – you've rec'd plenty of good info already.

    Mr. S – this is for you:

    Go slow. Be patient. Use a *lot* of lube. With regard to the "ick factor" – I never penetrate my girl's ass w/out gloves or condoms. Enema play can be a great addition to the experience, especially considering the kink, D/S perspective. Use a lot of lube. I know I already said it – but it bears repeating. Tristan's book is a great jumping-off place. There's a reason why she's the authority on the subject. She knows of what she speaks.

    And I can also tell you – fucking Kristen's ass will not be like fucking a guy's ass. I know this from my own experiences. The prostate means a man has a different physical response.

    And like all women – getting fucked in the ass means different things for each. I can only speak to my own experience, of course. But you've shared enough about yourself and your particular sexual dynamics w/Kristen that we can offer some sage advice.

    Start by introducing anal play in your regular sex. A well-lubed, gloved finger. Then two. Graduate to beads. Then a butt plug. Use condoms. When you're ready to use your cock, use a smaller one than normal with a smooth head. (I have a special cock just for ass-fucking).

    As a fellow "service top" (I thought I was the only butch who used that phrase!) I can tell you that the power surge that comes from knowing I give my girl more pleasure than anyone ever has before or ever will is unlike any other feeling in the world. The teasing, toying and eventual orgasm I give her is absolutely debilitating. She's like a zombie for hours.

    Okay, so maybe I do have some words for Kristen.

    My girl cums hardest when she has strong, forceful G-spot stimulation, indirect clitoral stimulation and a full ass. She says there's no other feeling in the world like it. That sensation of being "full". Knowing she's powerless to stop it. Feeling utterly submissive. Penetrated in every sense of the word. Knowing from Mr. S's blog – you are one of those very fortunate women who cums easily. Adding anal play to your sex life will only increase your pleasure.

  16. hmm all these ppl seem to know what they're talking about… please excuse my prude comment!

  17. i was introduced to anal several years ago by a partner and while i was super nervous at first, i grew to really love it.

    i spent a lot of time exploring it on my own, so K, maybe some alone exploration time where you don't have to worry about anyone watching or being excited to participate?

    i

  18. Ummm….some people love ass sex. Some people do not. Some people like to be tied to fences during Folsom with a funnel taped to their mouth – I guess what I am saying is ymmv.

    Whatever you decide you should make the best decision *for you* and your relationship based solely on your desire and interest. Seriously – this peer pressure approach to trying something new sexually rarely works. Like, all these people tell you it's cool and so you figure if you don't do it that makes you un-cool and really that's just a set up for you.

    There are things you can push yourself toward that can lead toward greater intimacy and fun in your relationship – but my opinion on the subject -frankly anyone's experience on the subject shouldn't matter to you.

    It can be really awesome and amazing….but it has to be your decision. And if you decide that you aren't feeling it right now that is ok too…. It certainly doesn't make you one ounce less sexy or adventurous or beautiful or daring or fun. Try to drown out the background noise and focus on what you really want. xoxoxoxoxoxox

    (not what you were hoping for SB – but that's my best honest answer.)

  19. I happen to enjoy anal sex. But this post annoys me. If your girlfriend isn't totally into it, she's not totally into it. Getting readers to encourage her? Really? If she doesn't already want it, don't do it.

    Maybe you should focus less on your cock, and more on her pleasure.

    "If only one partner has any interest in doing an activity, and the other either has none, or is opposed to it, it's generally best to just decline."

    - Heather Corrinna, Scarleteen

  20. while i can appreciate the perspective voiced in the last post that encouraging someone to do something they don't want to can be annoying, i would offer that my understanding of the spirit of the post was not one of coercion. and also that from everything i know from reading here about Sinclair, she is a careful, attentive and considerate lover. furthermore, i would expect any woman that Sinclair would be attracted to would be able to make up her own mind, regardless of the opinions of others. ultimately, i expect that what happens between Sin & her girl happens between them because they choose that for themselves, and not because of any of us out here.

  21. I really like anal sex, but since it requires so much foreplay it's not my go-to sex act.

    If you're both nervous about it, a little tip I recommend is Kristen to be on her back, rather than stomach for the first few (or several, or every) times. You'll be able to make eye contact, able to see each other and each other's bodies' responses.

    Approach it with no expectations – have the first time only being about rimming, or just a vibrator on the outside of the ass, or only penetration with one finger.

    I know Kristen ejaculates too, so hopefully as a fellow ejaculator she appreciates this encouragement. The first time my anal play included penetration (just one finger!) I ejaculated so hard and far it hit and went over my partner's face and shoulder! So hottt. Again – why being on your back is a an asset for the first few times. ;)

    Hope this helps!

  22. I can't really offer tips or advice, since I'm kind of in the same boat as you, Sinclair – I've wanted to, I've talked about it, and I've done some play – but haven't actually done it. I'm not sure why, except there has been the specific thought that I may hurt her during the act. I'm big, I'm strong, and I get physical – so of course that makes me a bit nervous.

    I will say that some of the best information I got about it was a conversation I had with two of my straight female friends, one who likes anal and one who doesn't. They discussed the pros and cons and talked about how to make it better (my friend who LOVES it said she likes it better while on top, because then she can control it). The frank discussion from them opened my eyes about what it's like to receive, both in a positive and negative way. So when it does happen, I'm hoping this feedback from women who receive will help me make it a good experience for my partner.

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