• Popping her anal cherry

    1231853277
    Kinky Star [sign in to see picture]
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    Naughty40 wrote:

    My point of view? From an more 'mature' forum user.

    Why (scuse the pun, non intended) push the issue? If shes not been happy with what happened last time, its going to take a fair amount of time to get used to it. Back off a little maybe?

    it has taken me a lot longer to even THINK about anal - let around to get round to it. Anal was not discussed when I was younger - very much a taboo subject, unlike now, you were 'wierd' if you thought about it.

    She is young, let her decide when....its her body after all.

    Though Im pretty sure that when you do, it will be very pleasurable for you both.

    Good luck....

    N40 - still waiting her her anal cherry to be popped!

    thanks N40. Since we last tried it - in April last year - we've not discussed it at all since. I do think it could be a point of, right place, right time, right mood. Last April, we tried it when my parents were away on holiday so we had the house to ourselves, and were both in bed together.

    This is why I've sent her the letter, with the instructions, only to be read when she's horny. If she's in the right mood to read what I have to say and to get her imagination going, then I hope I stand a chance. I do believe she will try it again, and I don't believe I've been pushy at all on this one since we've not talked about it for months. I do want her to decide absolutely, but she can't decide unless I tell her in the letter that I'd like to try it again, as we don't verbally discuss sexual preferences. Yes, we love sex, but we don't talk about what we like, we just do it. She sometimes feels uncomfortable talking about sexual postitions etc, in general, so verbally talking to her about trying anal sex again would be extremely difficult.

    Russ x

    1231853374
    walrus [sign in to see picture]
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    Hey Russ, will try to respond to your question, although my experience of doing it and of talking to people about it is quite limited.

    It seems to be the case that some people immediately like anal sex, some don't like it at first but get to like it, and some people never like it.

    As everyone is different, it's impossible to know whether the people who never liked it might have got to like it under different circumstances, or if they are just made like that.

    But anyway I don't think we should always assume that people who don't do it are missing out on something. We cannot know that, simply because everyone is different.

    What I am trying to say is that maybe it should not be such a big thing, there are much more important things in a relationship I think.

    Just my opinon.

    1231854530
    mama [sign in to see picture]
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    arr i think walrus might be right here.. the anal sex thing is a distraction.. mainly because you want it and of course she first suggested it.. but the real problem you have.. if you have a problem at all.. is the lack of comunication.. that will come and bite you in the arse everytime.. there is a difference between having a partner for sex and having a relationship.. when we are young we think they are both the same but they are not, you can find, especially on the internet these days, someone who will fulfil your every fantasy but that is not a relationship, however, and this is the biggy, if you do have a good realtionship thats based on good comunication you will have the most amazing sex, not always what you think you want .. because that can often be just a fantasy,(nothing wrong with those) but with good comunication you'll have knee trembling, ball aching, mind blowing sex, but you have to comunicate first, so your choice maybe either put away the anal lube for now and get talking or log on to the web and find ya self a back door girl.. mind you the letters may work for this as she did suggest it in the first place, just make sure you got your training plan ready and don't fuck up this time... love mama xxx

    1231855099
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    mama wrote:

    arr i think walrus might be right here.. the anal sex thing is a distraction.. mainly because you want it and of course she first suggested it.. but the real problem you have.. if you have a problem at all.. is the lack of comunication.. that will come and bite you in the arse everytime.. there is a difference between having a partner for sex and having a relationship.. when we are young we think they are both the same but they are not, you can find, especially on the internet these days, someone who will fulfil your every fantasy but that is not a relationship, however, and this is the biggy, if you do have a good realtionship thats based on good comunication you will have the most amazing sex, not always what you think you want .. because that can often be just a fantasy,(nothing wrong with those) but with good comunication you'll have knee trembling, ball aching, mind blowing sex, but you have to comunicate first, so your choice maybe either put away the anal lube for now and get talking or log on to the web and find ya self a back door girl.. mind you the letters may work for this as she did suggest it in the first place, just make sure you got your training plan ready and don't fuck up this time... love mama xxx

    thanks very much mama. so u think that we should verbally communicate more. but also, are u saying that the letters could well work?

    just one other thing, i'm hoping that she will read the letter before valentines day as we're going away to amsterdam for the weekend (originally her idea)....so i'm hoping the fact that it's our own room, away from parents etc, could help her relax etc. I'm also going to buy the deluxe bed of roses set, which also has bubble bath and edible massage oil. I'm hoping to have a very romantic evening with her, and maybe see how everything goes. Don't get me wrong by that, I'm not doing that just because I'm after anal sex. Not at all, we're madly in love. But if she reads the letter beforehand, then valentines could come at a good time.

    Russ x

    1231856519
    jessicarabbit88 [sign in to see picture]
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    Russ

    Just an opinion from a young girl that had a bad first anal experience and bad second one here feel free to dismiss.

    I first tried anal a couple of times with my previous boyfriend and he was putting on the pressure so much I couldn't relax and it hurt so much, I even bled because he tried to rush things. However my current partner, after a few months of being together brought up the subject and at first I just brushed off the idea everytime he mentioned it but one night when we were getting frisky in bed I was led on my front and he started to try anal play and then anal sex with plenty on lube and reassurance. I would say it is definately going to be a caught up in the moment thing. Definately go with mama's suggestion of focusing for now on commutication in your relationship. Definately be in a bed when you do try and I would recommend having her lay on her front completely flat and you lay on top this way she can relax easier than on all fours and still has the pillows to take a few deep breaths into. I would say that even now when my partner penetrates my ass for the first time it feels uncomfortable for a few seconds but once those first few thrusts are over I get this amazing feeling of fullness. It just feels so deep and wonderful. Hehe I'm getting carried away thinking about it. If I hadn't had a baby only a week ago I would be asking for anal tonight. Maybe in a few weeks.

    Good luck

    Jesse x

    1231857456
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    jessicarabbit88 wrote:

    Russ

    Just an opinion from a young girl that had a bad first anal experience and bad second one here feel free to dismiss.

    I first tried anal a couple of times with my previous boyfriend and he was putting on the pressure so much I couldn't relax and it hurt so much, I even bled because he tried to rush things. However my current partner, after a few months of being together brought up the subject and at first I just brushed off the idea everytime he mentioned it but one night when we were getting frisky in bed I was led on my front and he started to try anal play and then anal sex with plenty on lube and reassurance. I would say it is definately going to be a caught up in the moment thing. Definately go with mama's suggestion of focusing for now on commutication in your relationship. Definately be in a bed when you do try and I would recommend having her lay on her front completely flat and you lay on top this way she can relax easier than on all fours and still has the pillows to take a few deep breaths into. I would say that even now when my partner penetrates my ass for the first time it feels uncomfortable for a few seconds but once those first few thrusts are over I get this amazing feeling of fullness. It just feels so deep and wonderful. Hehe I'm getting carried away thinking about it. If I hadn't had a baby only a week ago I would be asking for anal tonight. Maybe in a few weeks.

    Good luck

    Jesse x

    thanks very much jesse! Yeah I definitely don't want to rush things, and I hope I've not so far. When your current partner proposed it to you at first - that could maybe be the same with me and the OH, in terms of me writing my letter. Although maybe I should speak to her after that as well.

    In terms of position, I know that her lying on her front can be done. Is it quite a good position to start with? I was thinking of her lying on the top of her back, a bit like missionary, but with her legs in the air and her ass in full view, compared to missionary where its the pussy that is. If you understand what I mean. I've heard that this is a good starting anal position? Having her lie on her front could also help with her nervousness if she sees me lubing up a finger. She wouldn't if she was led on her front, and I could reassure her a lot at that point.

    Russ x

    1231859038
    Lubyanka [sign in to see picture]
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    russ&clare wrote:

    Me & the OH tried anal sex a few months ago. [...] she mentioned trying it. I couldn't believe it!

    But we didnt prepare properly although i did use lube, maybe not enough, but I think she was nervous and therefore tight. So she said it hurt straight away. [...]

    Said it was my fault last time, and she'd be in control next time. I also told her about the butt plug set I have [...] All that maybe fine.....but she's still not read it yet!! [...]

    Last week I thought about lubing up my finger and reaching round and inserting it whilst we're having sex, hopefully to take her over the edge. [...] It's been difficult ever since we tried it, basically because the last time didn't go well.

    Anyone got any ideas if I've done the right thing in writing the letter? I really want to try it again as it's a huge turn-on for me & for us to enjoy it together, but I don't think that simply asking her would work.

    Russ, based on what you've said, this is my take on it, from the woman's perspective -

    I understood from what you said that,

    1. you have a big kink for anal

    2. she agreed to try it for your sake, because she cares about you

    3. she could feel that your feelings for her were reflected in your failure to take sufficient precautions to keep her safe from pain and injury

    4. she left the anal up to you, and she has learnt that you cannot be trusted with her safety and comfort

    5. she could feel you are not to be trusted with her safety and comfort with anal again, since one episode of pain is too many

    6. because you keep mentioning and mentioning anal, no matter how lovingly, she could feel that you are willing to risk her safety and comfort again just to get your rocks off, because she could feel like you did that the last time

    7. she might feel like even though she initiated anal for you last time, your carelessness resulting in her pain and suffering was how you showed your appreciation

    Russ, I feel that this issue is nothing at all to do with anal.

    I think this is entirely to do with trust, and entirely to do with validation.

    I think she needs to hear from you that you are going to prioritise her safety and comfort over everything else in the entire universe. If she is to have any chance of believing you, then you are going to have to prove beyond a shadow of a doubt that this is in fact what you're doing.

    And I think the only way you can do this is to allow her to choose everything you do together, and to utterly and without question or quibble respect her choices 100% of the time.

    So my advice is to leave the topic of anal strictly and completely alone, and never ever discuss it again until she does. She knows you have a kink for it, she will bring the topic up when she is ready.

    So remain off anal for a good long time. Keep off the topic altogether. Leave it entirely alone

    Even though you might not like this advice, this is honestly what I think.

    I wish you both the best of luck.

    Lubyanka.

    1231861258
    mama [sign in to see picture]
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    Lubyanka wrote:

    So my advice is to leave the topic of anal strictly and completely alone, and never ever discuss it again until she does. She knows you have a kink for it, she will bring the topic up when she is ready.

    So remain off anal for a good long time. Keep off the topic altogether. Leave it entirely alone

    Even though you might not like this advice, this is honestly what I think.

    I wish you both the best of luck.

    Lubyanka.

    lubyanka may be right.. but as you don't talk about sex you won't know.. maybe asking her what she wants, getting her to write to you, if you can't manage face to face yet, would be good.. maybe writing a letter to say sorry you cocked up the anal because of your inexperience not hers would be good too.. trying in amsterdam sounds like a bad thing to do unless she askes, even then could take weeks of training to prepare her.. two people both inexperienced in what is a potentially difficult sexual act can be a mare... when i introduced my hubby to anal i did all the prep without him knowing so all he needed to do was stick his cock in my arse, he couldn't have coped with the prep as he would have been too embarassed.. he can now because he feels more in control... which along with trust is probably what your girlfriend needs.....

    1231864665
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    Lubyanka wrote:

    russ&clare wrote:

    Me & the OH tried anal sex a few months ago. [...] she mentioned trying it. I couldn't believe it!

    But we didnt prepare properly although i did use lube, maybe not enough, but I think she was nervous and therefore tight. So she said it hurt straight away. [...]

    Said it was my fault last time, and she'd be in control next time. I also told her about the butt plug set I have [...] All that maybe fine.....but she's still not read it yet!! [...]

    Last week I thought about lubing up my finger and reaching round and inserting it whilst we're having sex, hopefully to take her over the edge. [...] It's been difficult ever since we tried it, basically because the last time didn't go well.

    Anyone got any ideas if I've done the right thing in writing the letter? I really want to try it again as it's a huge turn-on for me & for us to enjoy it together, but I don't think that simply asking her would work.

    Russ, based on what you've said, this is my take on it, from the woman's perspective -

    I understood from what you said that,

    1. you have a big kink for anal

    2. she agreed to try it for your sake, because she cares about you

    3. she could feel that your feelings for her were reflected in your failure to take sufficient precautions to keep her safe from pain and injury

    4. she left the anal up to you, and she has learnt that you cannot be trusted with her safety and comfort

    5. she could feel you are not to be trusted with her safety and comfort with anal again, since one episode of pain is too many

    6. because you keep mentioning and mentioning anal, no matter how lovingly, she could feel that you are willing to risk her safety and comfort again just to get your rocks off, because she could feel like you did that the last time

    7. she might feel like even though she initiated anal for you last time, your carelessness resulting in her pain and suffering was how you showed your appreciation

    Russ, I feel that this issue is nothing at all to do with anal.

    I think this is entirely to do with trust, and entirely to do with validation.

    I think she needs to hear from you that you are going to prioritise her safety and comfort over everything else in the entire universe. If she is to have any chance of believing you, then you are going to have to prove beyond a shadow of a doubt that this is in fact what you're doing.

    And I think the only way you can do this is to allow her to choose everything you do together, and to utterly and without question or quibble respect her choices 100% of the time.

    So my advice is to leave the topic of anal strictly and completely alone, and never ever discuss it again until she does. She knows you have a kink for it, she will bring the topic up when she is ready.

    So remain off anal for a good long time. Keep off the topic altogether. Leave it entirely alone

    Even though you might not like this advice, this is honestly what I think.

    I wish you both the best of luck.

    Lubyanka.

    Lubyanka, please let me reply to some of your points as I have to admit to feeling slightly patronised by the way you have written your post. This is not because I may agree or disagree with any of your points, in fact I do see some validity in your thinking, however the manner in which you have written them is my problem.

    1) Yes I do have a kink for anal. However, my OH does not know this, she does know that when we did start having sex I may have briefly mentioned it, but since then that is all that has been said.

    2) She did not agree to try anal, the only time we did it. It was her who mentioned we should try it, not me. This was quite a long time after I had mentioned trying it, we were both quite drunk, and had a free house away from parents.

    3) I have not kept on mentioning and mentioning anal. I have raised it once as I have said a long time ago. Since then I have not said anything until the letter which I wrote to her, which she is still to read.

    I believe that some of the points that people have mentioned are most certainly valid, that is the whole point in me asking the question and for asking peoples advice. I am certainly not going to rush into anything, and I will base anything on how, if at all, she reacts to my letter. The last time we did try anal, she did say that there could be a chance that she would try it again. Her trust in me is the number 1 priority, I have thought this already, and that is something that I will definitely sit down and talk to her about asap.

    As a lawyer, I get used to the different inferences in the things that people say, and that is definitely what I will attempt to judge when I speak to my OH and also gauge her reaction to my letter. Once I have done this, will I be able to tell if we should go any further with it, or not. Certainly the policy of her bringing it up and not me, could be a good plan, and is something which I will definitely consider highly.

    I apologise if this seems to be a rant, however, Lubyanka, I understand these are your opinions, and I am extremely grateful, but the way in which it was phrased made me respond.

    Russ x

    1231865322
    Lubyanka [sign in to see picture]
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    russ&clare wrote:

    1) Yes I do have a kink for anal. However, my OH does not know this, she does know that when we did start having sex I may have briefly mentioned it, but since then that is all that has been said.

    2) She did not agree to try anal, the only time we did it. It was her who mentioned we should try it, not me. This was quite a long time after I had mentioned trying it, we were both quite drunk, and had a free house away from parents.

    3) I have not kept on mentioning and mentioning anal. I have raised it once as I have said a long time ago. Since then I have not said anything until the letter which I wrote to her, which she is still to read.

    Hello Russ,

    I apologise for misunderstanding the facts. As you see, I was basing my reply on the facts as I understood them.

    Thank you for clarifying my errors. I really do hope things work out between you and your partner.

    Best regards,

    Lubyanka.

    1231873604
    tallboy247 [sign in to see picture]
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    Lubyanka wrote:

    russ&clare wrote:

    1) Yes I do have a kink for anal. However, my OH does not know this, she does know that when we did start having sex I may have briefly mentioned it, but since then that is all that has been said.

    2) She did not agree to try anal, the only time we did it. It was her who mentioned we should try it, not me. This was quite a long time after I had mentioned trying it, we were both quite drunk, and had a free house away from parents.

    3) I have not kept on mentioning and mentioning anal. I have raised it once as I have said a long time ago. Since then I have not said anything until the letter which I wrote to her, which she is still to read.

    Hello Russ,

    I apologise for misunderstanding the facts. As you see, I was basing my reply on the facts as I understood them.

    Thank you for clarifying my errors. I really do hope things work out between you and your partner.

    Best regards,

    Lubyanka.

    Welcome to the club there Lubyanka,!!! been there, got the t-shirt, it is annoying though when it happens isn't it, the old exam problem methinks reading what you think it is rather than what it says!!! You get over it though.

    TB

    1231874955
    BeeBeex [sign in to see picture]
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    My first time was a total surprise, i was having some quality time with mr bunny when my partner came home and it just kind of happened...

    Previous to that i was reluctant to try it, but just got caught up in the moment and therefore just went with it. It meant i was more relaxed and there was No pressure. If i was uncomfortable at any point i could have said stop without it being embarrasing or an issue.

    x

    1231875217
    tallboy247 [sign in to see picture]
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    I have to say that l am really in a priviledged position on this one, literally. The angle of my cock when erect means that it often slips into Mrs T's back door. Fortunately she encountered a monster cock in Cumbria some years before we hitched up and he stretched her to the extent nothing is really a problem in that dept. any more.

    Have to say the grip is fab, and she screams the place down when she comes, so maybe that is where you will end up!!!

    Good luck.

    Tallboy

    1231876326
    Kinky Star [sign in to see picture]
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    tallboy247 wrote:

    I have to say that l am really in a priviledged position on this one, literally. The angle of my cock when erect means that it often slips into Mrs T's back door. Fortunately she encountered a monster cock in Cumbria some years before we hitched up and he stretched her to the extent nothing is really a problem in that dept. any more.

    Have to say the grip is fab, and she screams the place down when she comes, so maybe that is where you will end up!!!

    Good luck.

    Tallboy

    What.....end up in Cumbria TB.....!!! Only joking haha! sorry......i'll get my coat!!

    But thanks for that. You're a lucky guy with the angle of your cock.

    Russ

    1231876878
    Morbidia [sign in to see picture]
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    I agree with most of the comments on here, especially when it comes to the communication and the trust issues.

    Communication is definatly a vastly important thing in a relationship, so you'll need to get past this lack of it, even though this may indeed be a task, as previously stated, she is young, but it does need sorting.

    And the trust issue that Lubyanka was talking about is a very valid point, if she doesnt feel comfortable and able to trust you to be gentle etc or believe that you wont hurt her, it will be a very difficult topic to bring up, and an even more difficult task to act out. As i know from experience, that just ONE incident of pain can seriously effect someones view and feelings towards physical acts.

    And what Walrus said about there being more important things in a relationship than acting out a fantasy, and that some people like anal, others grow to like it, and some simply never like it, no matter how much they try, are also very important points.

    I think you're just going to have to talk her about this, so you can understand her opinions on it.

    1231879689
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    thankyou for your advice morbidia! Everything helps!

    Russ x

    1231879975
    Morbidia [sign in to see picture]
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    No worries, its what the OA is here for ^_^

    x x x

    1232191081
    Randy-Andy [sign in to see picture]
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    whats good for one, is good for the other, if he says no, then say no to him, who will give in first??

    1232191193
    tallboy247 [sign in to see picture]
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    Hi Randy, so you have escaped the confines of the palace have you !!!

    TB

    1232247473
    Mucky Duck [sign in to see picture]
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    Russ, There is alot of good advice listed, here's my two cents. Mrs Duck didn't like anal at first either, I was way too eager & rushed things. We love it now. The two key things is start small & take it slow. It could take a few months of building up to just popping your helmet in.

    • I would start by making it normal for her to have her ass touched. Try licking it when you're down on her, tickle her hole with your finger & rubbing (ABSOLUTELY no penetration)
    • Buy her a small butt plug/ anal vibe, forget the kit you posted, WAY too scary , have a look at http://www.lovehoney.co.uk/product.cfm?p=13662 http://www.lovehoney.co.uk/product.cfm?p=9758
    • Let her have a go on her own with the new toy until she is comfortable, Get bum lube too!
    • If she responds to the butt plug, try using it or a finger in there whilst licking her pussy.

    First Go

    Once all the above is completed & only if she's happy, ask her if she's willing to try again, if so- get midly drunk together (helps relax the muscles).

    Open her up with either your finger or plug during oral. Lube her up really well (after paying her pussy attention first), lube yourself up too. Put her on her knees with lots of pillows under her for support.

    Very very very slowly ease your helmet into her ass (she has to keep relaxed, a clit buzzer could help) once you have popped in STOP, do not move. Let her become used to your tip & girth. Talk to her for feedback.

    Once she is relaxed again & comfortable you have to ease in a fraction of a inch at a time, each time stopping & waiting for her (If you lose your self control & go for it, it's game over boyo!).

    Once you are fully in or she can't take any more just stop & hold her tight & make a big fuss of her. Unless she really wants you to fuck her ass, withdraw & pack up for the night. She will be alot less scared for next time.

    Second go

    Repeat all above steps until you are fully in & she's happy. Start to withdraw slightly to about half way, very very slowly start to move in & out about an inch until she gives the nod, then two inch V.Slowly & again until you are fully driving home GENTLY. If you are wanting to cum in her ass make sure you want last long in there!!!!

    Do not get carried away & go bananas until she's completely happy & she trusts you in there (thats 80% of the battle), it could be several times of anal explorations before you can really 'fuck her ass'.

    Don't rush her, it is well worth the wait & effort. Hopefully you will both love it. Mrs Duck seemsto get so much more from it than me these days, she goes absolutely wild!!!!

    Good luck!

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