Ease into pegging?

adirondacker adirondacker
I have been with my girlfriend for almost a year now and I absolutely adore her. In every way she is the most perfect woman except for her sexual adventureness. She is so timid in bed but I really want to try pegging! I thought maybe about talking to her about anal sex but she won't hear any of it. How if my girlfriend isn't interested in anal herself can I ease her into knowing that I want it? I want to make this happen and don't think going straight to pegging will work for us. What would be a toy she may find appealing to try on me that could lead us down the road of pegging? And any ideas on how to approach her about this?
06/28/2009
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Lara Lara
Quote:
Originally posted by adirondacker
I have been with my girlfriend for almost a year now and I absolutely adore her. In every way she is the most perfect woman except for her sexual adventureness. She is so timid in bed but I really want to try pegging! I thought maybe about talking to ... More
Have you ever tried rimming her? Even "accidentally" while performing oral on her? Maybe if you two spend some time exploring how much fun non-penetrative anal stimulation can be, it will be easier to move on to anal penetration.
06/28/2009
adirondacker adirondacker
Quote:
Originally posted by Lara
Have you ever tried rimming her? Even "accidentally" while performing oral on her? Maybe if you two spend some time exploring how much fun non-penetrative anal stimulation can be, it will be easier to move on to anal penetration.
To be honest I have never even thought about trying that until reading your post...hmmm. I feel so devious and horny just thinking about it but I have never done it before. Wow I can't wait to try and pull this off, she would never let me just go for it but maybe like you say "accidentally"
06/28/2009
Luscious Lily Luscious Lily
Quote:
Originally posted by adirondacker
To be honest I have never even thought about trying that until reading your post...hmmm. I feel so devious and horny just thinking about it but I have never done it before. Wow I can't wait to try and pull this off, she would never let me just go ... More
Just be very careful with this. If she thinks you're trying to trick her into something, you could lose a lot of trust. I'm not saying "accidentally" slipping back there with a tongue or finger is completely a bad idea, just be very careful.

I notice that your reviews are, thus far, only of toys you use. Do she use toys? Do you use any together? If so, another way to ease into this, and into more sexual adventurousness in general, could be through toys. You could get something like a cock ring with ticklers on both sides, and tell her that the reviewers said it would feel really good. (not a lie, I'm a reviewer and they ROCK) From there, if she enjoys it, you could move on to brushing it with a finger or tongue during oral, or maybe a rabbit with a probe in the back, or if she's game a small probe like yours.

If she doesn't enjoy it, that's not the end of the world. There is still hope for pegging, but you'll have to go slowly either way. This is not something that's going to happen overnight, or in a weekend, or even in a month. If she doesn't know already, be open about the fact that you enjoy it, but with the emphasis that you want a lady like herself on the other end, not a dude.

Either way, as Lara said, mutual exploring on the outside can help her ease up to it. If the "dirty" factor is a real sticking point for her, shower together first. Or better yet, do your playing IN the shower.

Bottom line? Enjoy all of the play and seduction on the way to pegging. It could take a while, and you don't want to miss how much fun the road can be because you're so focused on the end-goal. Because the intermediate stuff is ridiculously fun too.
06/29/2009
Lara Lara
To clarify the oral exploration... When you've got your tongue inside her, begin stroking her anus very lightly with the flat of your thumb. Don't insert anything at all!! NONONO!!! Just get that area used to being touched. The idea is that if you've got your mouth on her clit, the external anal stimulation is going to be contributing to the overall goodness and not creating an entirely unique sensation on its own.

After a while keep your mouth on her clit and insert a finger or two inside her. After you've begun fingering her, move your mouth down to her ass and begin rimming her. Like the above, the idea is to use the anal stimulation to compliment something she already knows and enjoys and not make it this sort of random, self-conscious wtf kind of thing.

If all goes well, after all is said and done she'll ask you what it was that you did. You can then explain to her that you wanted to see what it was like to tongue her ass.

I'm all about openness and being forthright with your partner, but I also think reserved sexual partners can be kind of like children with their vegetables. You have to be sneaky with vegetables sometimes and wait until you hear "boy was that good!" before you tell them that fabulousness was the dreaded broccoli.
06/29/2009
adirondacker adirondacker
Quote:
Originally posted by Luscious Lily
Just be very careful with this. If she thinks you're trying to trick her into something, you could lose a lot of trust. I'm not saying "accidentally" slipping back there with a tongue or finger is completely a bad idea, just be very ... More
Yeah I would never just accidentally shove my finger up her butt or something when she wasn't looking. It took her a long time to even let me go down on her but now she loves it! But like Lara says below "I'm all about openness and being forthright with your partner, but I also think reserved sexual partners can be kind of like children with their vegetables." Thats my girlfriend stubborn to her cause but opens up slowly. And you both make good points about how to start down this road of sex toys and anal play. Was there any tickler you could recommend? I think that is something she may be able to go for.
06/29/2009
adirondacker adirondacker
Quote:
Originally posted by Lara
To clarify the oral exploration... When you've got your tongue inside her, begin stroking her anus very lightly with the flat of your thumb. Don't insert anything at all!! NONONO!!! Just get that area used to being touched. The idea is that ... More
I love how you compare it to kids and there veggies it is so true of her! The first time I ever went down on her it was almost as if she just gave up the fight so she could just say we had tried it and she didn't like it, but to her surprise she fell in love with it and it is normal part of our everyday sex life.

I think I am going to try your suggestion for the next time her and I have oral sex. After I slide my finger in letting my thumb fall down and rest against her anus. See how she responds to each step and progress slowly to actually massaging it. I know she doesn't want to try anal sex right now so I won't even attempt to penetrate her. But hopefully this will become a whole new branch of the sexuality tree to explore!

Both Lara and Lily Thank you for your help I can't wait to put your suggestions to use!
06/29/2009
Luscious Lily Luscious Lily
Quote:
Originally posted by adirondacker
Yeah I would never just accidentally shove my finger up her butt or something when she wasn't looking. It took her a long time to even let me go down on her but now she loves it! But like Lara says below "I'm all about openness and being ... More
We love this one: link
But it is definitely on the large side as far as cock rings go, so it can be intimidating in and of itself.

Here are a few that have high ratings. You should head over and read their reviews, look at the pictures and sizes, and see what looks like something you two could go for.
This one looks the least intimidating: link

A few others to look at are:
link
link

If even the least intimidating are too much for her, you could try a basic disposable ring like the Durex ones that you can get in drugstores. Leave it in position when you move into rear-entry positions like doggy-style, and it will brush her ass. Same effect, but without the "that's meant for the ass, isn't it!" reflex.

I realize I sounded a little sharp earlier, and I just wanted to explain that this is coming from someone who was on the other side of Anal101 a few months ago. There was a time when even a tongue flicking back there would have made me freak out. From the sounds of it, your girl isn't quite as skittish as I was, so you're already ahead of the game.
06/29/2009
Luscious Lily Luscious Lily
Quote:
Originally posted by adirondacker
Yeah I would never just accidentally shove my finger up her butt or something when she wasn't looking. It took her a long time to even let me go down on her but now she loves it! But like Lara says below "I'm all about openness and being ... More
We love this one: link
But it is definitely on the large side as far as cock rings go, so it can be intimidating in and of itself.

Here are a few that have high ratings. You should head over and read their reviews, look at the pictures and sizes, and see what looks like something you two could go for.
This one looks the least intimidating: link

A few others to look at are:
link
link

If even the least intimidating are too much for her, you could try a basic disposable ring like the Durex ones that you can get in drugstores. Leave it in position when you move into rear-entry positions like doggy-style, and it will brush her ass. Same effect, but without the "that's meant for the ass, isn't it!" reflex.

I realize I sounded a little sharp earlier, and I just wanted to explain that this is coming from someone who was on the other side of Anal101 a few months ago. There was a time when even a tongue flicking back there would have made me freak out. From the sounds of it, your girl isn't quite as skittish as I was, so you're already ahead of the game.
06/29/2009
ScottA ScottA
I agree with the other posters: bring the toys into the relationship first, and bring the anal play into the relationship first. Then you're only springing the "you want me to f*** your ass??" (potential) bombshell on her, not all three at once.

I don't know if I'd advise starting with rimming - it's another psychologically loaded activity. Stick with the external stimulation of the area until she's 100% OK and comfortable with it. Erotic massages are a good way to start. Start off just playing with her buttocks, and then over the course of a couple months work up to where you're stroking over her anus. Don't heavily massage it, don't insert anything, just slide a well-lubricated hand over the area repeatedly, perhaps to the accompaniment of a little oral action up front. Don't do anything else before talking about it.

Then, see if you can get her to give you a butt massage. Tell her how much you love it - be explicit. See if she'll play with your balls. etc. Eventually she'll probably touch your anus and you can go from there (moan, say "ooh, do that again", possibly even just fib a bit: "honey, last time you were massaging me you ran your fingers over my anus. It felt soo good - could you do it again?) (perhaps when she's in the afterglow of an orgasm - the ladies here will think me a horrible for taking advantage of ladies this way, but women are somewhat more suggestible after you've licked them to orgasm once or twice (or thrice...).

Go slow. Introduce toy play elsewhere, and then eventually you can put the two together (but I'd still not recommend going straight for pegging. Get comfortable with hand-held toys and assplay first before you suggest strapping one on her).

Another possible way to begin, provided you masturbate in front of each other, is to just show her how much you like doing it to yourself. Ham it up a bit. She might just be scared about what you'll think. My wife doesn't want much anal play herself yet, but she's just fine playing with mine.
06/29/2009
ScottA ScottA
Oh, and when she does finally start to penetrate you with something (probably a finger), make sure she doesn't run into any poop. Excuse yourself to the bathroom, use the toilet, and check things out with your finger first.
06/29/2009
adirondacker adirondacker
I have to say I was skeptical of how these forums would work for me but I am very impressed. Everyone has been leaving really thoughtful posts and it has made it a lot easier to wrap my mind around this and the similar topics I am curious about. I have come to the conclusion that my girlfriend and I won't be pegging anytime soon and I am ok with that. I see that there is a lot more to this then the physical act. Knowing my girlfriend and the way she reacts to certain things these will need to be taken slowly but I think over time it will be a reality.

That being said, I think as far as toys are concerned I am going to try and go with some kind of small and intimidating toy; most likely a cock ring. I think that is something that she will get much appreciated pleasure from and should open her up to future toys

As far as anal play I really feel I need to show her how good it feels before I could ask her to even consider touching mine. She knows how much I enjoy it when she plays with my balls and I do plan on asking her to move down a little lower to the perineum the next time we are together. If there has been any success with me stimulating her anus I will suggest she try it to me.

Many of these things are major IFs right now but I am hoping that with a slow enough pace and over time this will happen. I love her very much and don't want to do anything to stop her from trusting me or feeling uncomfortable for that matter.
06/29/2009
spicywife spicywife
I was the one who sprung the idea of pegging to my husband. We've been together for over 8 years and we've used sex toys and prostate massagers. It' a bit different scenario than you have, but communication is key. If you want a long-term relationship with your girlfriend, you should really think about opening up to her. But then again I'm big on communication and I suppose it's not for everyone. You seem like you know your girlfriends limits, so just trust your instinct. Maybe you an gradually get her into the idea of sex toys and then someday pegging! Good luck!
07/05/2009
adirondacker adirondacker
Quote:
Originally posted by spicywife
I was the one who sprung the idea of pegging to my husband. We've been together for over 8 years and we've used sex toys and prostate massagers. It' a bit different scenario than you have, but communication is key. If you want a long-term ... More
I actually have been talking to her more about the idea of using sex toys together. Part of her problem with sex toys is her up bringing and the guilt she feels about her sexuality and her religion so I have decided to start using the terms "kinky" and "sex toys" for things I normally wouldn't. Like I am referring to using lube during oral as kinky, which I don't really feel it is but for her this will make it better when we expand into actual toys. Which by the way I just purchased link which doesn't really look intimidating to me. She doesn't yet know I have ordered it but she does know I want to try a small vibe with her for her pleasure, the only step will be introducing it into our sex. I plan on showing it to her before we really get too sexual one night that way she can just get used to seeing it and we will see where we go from there !?
07/06/2009
Valyn Valyn
As someone that has sometimes acted a little like a kid in front of yucky veggies (see this post), I think I can somewhat relate to your girlfriend. I'm not religious, but at first, any anal play was just bad- even if I kinda liked it.

My boyfriend started really slowly.. when going down on me, he'd lick in between holes, and that felt really naughty, but didn't quite dip into that "Bad" area. Or, when he was fingering me or touching me down there at all, sometimes he'd put a thumb or a finger over my anus, not putting anything in, of course. Eventually he moved to rimming- first with just one lick that made squirm and feel weird, but then.. he'd try it a little more and a little more- and while he was touching or between rimming, he'd ask me if I like it. We've always been very honest and open with one another, and in the act, I can't lie. I liked it. After that, during sex, he'd hold my ass cheeks open (which also gets him in deeper) and that slowly moved to a finger on top of my anus, and then.. in! Maybe he was sneaky about it, pushing a (well-lubed up) finger in just as I was about to cum, but after he asked me about it, and there was no denying it. It felt naughty and forbidden, but I really liked it.

I'm still very timid about getting into anal play, but once I get into it, I do love it. A slim plug was my first toy, and most definitely not my last!

Hope my story helps a little!
07/06/2009
spicywife spicywife
Quote:
Originally posted by adirondacker
I actually have been talking to her more about the idea of using sex toys together. Part of her problem with sex toys is her up bringing and the guilt she feels about her sexuality and her religion so I have decided to start using the terms ... More
The vibrator that you chose doesn't look intimidating. It's cute and classy. Also, did you know that there are books (and web sites) that support sex toys and sexual "adventure" for religion (christian) partners? I wonder if that's something that might help your girlfriend too. I can understand that her upbringing has caused her to think bad about things like that. It's great that you are being sensitive with her.
07/06/2009
Total posts: 16
Unique posters: 6