Anal Sex and Actual Pleasure

[chroias.livejournal.com]

Okay...err...here goes.

As you can tell by the title I am here about anal sex. I have a sincere enjoyment of anal sex both receiving and preforming it. My girlfriend, goddess bless her, wants to give it to me and has tried multiple times.

It's a complicated issue, something we've been working on for years. One time, ONE TIME, I managed to actually give her an anal orgasm. But the same method didn't work twice (damn our female bodies and their constantly rearranging pleasure zones). I've done everything I can think of from ensuring cleanliness to slowly working up from small toys (about this size of a thumb) to the size of an average phallus (5x1). It feels okay, at least she can take it with only a minor amount of discomfort, till about this http://www.edenfantasys.com/anal-toys/anal-probes/key-to-your-butt however after that it just hurts too much.

I was willing to drop it and let it go. I figured you know it's not that big a deal, and if the smaller ones work for her then okay we can still have plenty of fun with just that. But she feels really guilty about not being able to give me one of my fetishes. She actually cried the last time because she felt she had failed! FAILED! I was thrilled that she had tried so hard for me! It made me want to fuck her even harder!

She says it's because I give her all her fantasies and work so hard to do what she likes. She wants to make sure she can make mine come true. I reminded her that I am good at her fantasies because I enjoy giving them to her and I get pleasure from them too. So I don't want her to do this if she just can't get pleasure from it to. But she wants to, and I want to. But I don't want to hurt her. But she feels OBLIGATED to take it!

*head desk*

I'm at my wits end! I want to make this good for her. She really enjoyed it when we made it happen that one time and I think we both want to take it to that level again. This isn't something that we do every day. It's maybe once a month or so when we're feeling ready for that level of (frankly) effort.

I want to just make it pleasurable. I want to help her enjoy it. It's not impossible and I've done my best to read up on it. Well now I'm after more practical advise.

Comments

[adamantplatypus.livejournal.com]

I hope I'm not rambling, here, but I kind of know what you're talking about, so maybe it will help:

I'm not all that into anal sex. It hurts sometimes (once he pushes in past a certain point, it's too thick - but he's good about just partial penetration), and other times anal play is just neutral for me. Not positive or negative; I don't get pleasure from it but just the head isn't painful either, so he plays around to his heart's content.

I know how much my boyfriend likes it. HIS pleasure of it makes me go wild, so I don't mind doing it. He makes me feel safe and loved and secure and I don't mind doing it for him. He lets me decide when, but occasionally I'm like "Why don't we....." even though I don't really get anything out of it.

[adamantplatypus.livejournal.com]

I guess what I'm saying is that seeing my partner enjoy it makes it totally worth it to me. He can get me off in other ways, before or after. :D

[chroias.livejournal.com]

TY for your input. You may have a point there. When I'm getting her ready and prepping her for it I try to do everything to show her I'm concerned about whats happening to her. She did say it comes off as a little distant, like I'm not enjoying it. I told her that it's not that I'm not enjoying it I'm just trying to be emotionally supportive and not go overboard or... well... scare her by getting to excited.

[lightsabove.livejournal.com]

I think, from what you've said, that it's more a mental thing for her. I don't think it's a physical type of thing. She feels she isn't fulfilling your fantasies, not giving back what you have given her.

This is more mental then a physical stimulation. I think you should focus on talking about it. Patience will be needed.

God knows I had to learn that I AM good enough for my boyfriend, and I AM fulfilling his pleasures. It took a while to see I was worthy.

If it pleasures her by doing what YOU like, then I think you are overreacting a little. If she is doing JUST because you want to, and is NOT enjoying it, then you aren't overreacting.

And that is my two cents. :)

[chroias.livejournal.com]

We tend to do a little bit of bargaining when it comes to fetishes and fantasies. If there is something she wants to do that I may not be into or isn't my favorite thing, she will offer me one of my fantasies at a later date so that we both get satisfaction the way we like it. So we switch out. She feels like she isn't 'keeping up her half of the bargain'. I'm afraid it's going to make her not ask for what she wants OR make her feel guilty for asking when she knows how hard it is for her to reciprocate.

[the-bone-doctor.livejournal.com]

This is one of the sweetest problems I've ever heard. I love that you two sincerely want to give each other pleasure. That's wonderful!

A suggestion: Have you tried incorporating other stimulation at the same time? For example, holding a vibrator to the clitoris while there's a toy in the anus? Or, a second dildo in the vagina at the same time? Sometimes, having stimulation in a part that's used to pleasurable stimulation can help the new part learn how to enjoy it too?

[chroias.livejournal.com]

She actually said she doesn't like it when I touch her or try to stimulate her while doing anal. That may be part of the problem. I try rubbing or licking or stimulating her nipples (her's are so sensitive she can achieve climax if I do it right) and she starts shaking her head and saying Nonono. She puts all her focus into what she is doing and I think it's just making her more tense because she won't let herself be distracted.

[withinmywill.livejournal.com]

Then encourage her to stimulate herself? That works for me!

[stacy288.livejournal.com]

I find it very easy to orgasm through anal sex with Ben Wa Balls. It's very sexually gratifying for me. <3

[chroias.livejournal.com]

That might be a bit too much for the level we're at now! besides I'd be terrified of losing them in there!

[stacy288.livejournal.com]

I totally understand. Took me a bit to get comfortable with them too. You won't lose them though, I promise :D And I should have specified, use them in the vagina, not anally :) I hope you find something that works for you two!

[tornattheelbo.livejournal.com]

I used to be rather fearful of my ass, but was kind of curious. It took the right partner to just be really slow, and gentle and find the good spots with fingers first, and then toys later.

she needs to relax, completely. she must let go of all the tension in her body initially so that insertion is comfortable, and once you are in and everything is lubed and going well you can try different things, poking at different areas and gauging reaction.

I think mostly it takes patience

[rubyscarlett.livejournal.com]

Haha you two remind me of my boyfriend and I. Not with anal, we both enjoy it, but with specific positions.

Him: Let's do this one it's your favourite! *gets ready*
Me: Oh my god yes but honey it's not *your* favourite I know it won't make you come, let's do this other one *gets ready for other one*
Him: Well, no 'cause that won't make *you* come and I want you to come, I don't care about me.
Me: But I care about you! I don't care about me!

It's terrifying typing it. Lots of good advice above, I just wanted to share our story :D

[pixietangerine.livejournal.com]

What if you tried inserting/having her insert a plug into her anus, and then just kind of pretend it's not there and do vaginal/clitoral/nipple/whatever she loves for the actual stimulation and bring her to orgasm that way? It sounds like she's focusing too much on her inability to orgasm from anal, if she could orgasm from other stimulation but have just a little bit of anal stimulation from the butt plug her brain might slowly learn to associate anal stimulation with orgasm/intense pleasure...which in turn could train her brain to find the anal action itself more pleasurable. Also, maybe have her try telling herself *she* wants the anal, not just you? Like, have her ask you to insert a butt plug (or beg, if you're into D/S or anything like that?) or have her fantasize about you doing stuff to her anus while she masturbates/while you two have other kinds of sex...it's kind of a mental thing, at least for me it is! I hated the idea of anal for ages, but when my partner mentioned it in dirty talk and I could see how the idea turned him on I researched it and slowly incorporated it into my own fantasies during masturbation until it got to the point where I actually *wanted* to try it. And it turned out to be something we both really enjoy, but I don't think it would have been if I'd been doing it without building up my own curiosity/desire for it first, you know?

[trista-zevkia.livejournal.com]

Let me hang my head in shame b/c I can't believe I'm even suggesting this, except you seem to be in a loving, committed relationship. Get her agreement before hand, always and forever, then get her drunk.
Some people, it super relaxes them, so you'll have to stay sober enough to keep in control, go slow and just lower her inhabitions and see if it can work. Permission! Get permission even in a committed relationship and watch for any signs of distress. I'm just suggesting a way to relax her, since she sound tense about the whole thing.

[crazy-heva.livejournal.com]

alcohol does work for me in this situation. But also practice! i have managed to really enjoy it twice and it drove my boyfriend crazy, he loved it but it's so hard to remain relaxed long enough. Other simulation is key for me too, if I think over what is going on it hurts but if i just go with it i enjoy it.

One problem now in general my boyfriend and i moved in together recently and drink together almost every time one of us does drink. I have the best sex drunk and can relax to levels I normally can't despite a healthy sex life. The problem is that after just a few drinks he can't finish, so I am having the time of my life and he just gets more frustrated. So watch the alcohol levels too! Or the plan may well backfire!