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wonderingaboutthis posted:
After 30 years of happy marriage, my wife is finally responding in a favorable way to my requests for anal sex. My first wife loved it, and I have longed for it ever since, to no avail. Until the other night.

I plan on taking things very slowly over a period of several nights, have read tons on the subject, and my memories of how to do it properly are still with me from my first marriage.

One problem we seem to be running into though...I have been carefully inserting a well-lubed finger in her anal opening, and she has responded well to that, but a couple of times she complained of a "nauseous" feeling or a "sort-of gag type relex" occurring.

I haven't attempted to penetrate her anally with my penis yet, that will come later as we progress.

I am adamant that I actually don't want anal sex with her unless it is going to be something she enjoys also. Otherwise, it loses its appeal to me, I want it to be something we both like and do as an occasional "special" thing. But I'm not going to get past square one unless we address this "sick" feeling she gets.

I wonder if other women who enjoy anal sex have ever had this occur? If so, what do you think caused it and how did you get past it? Please help a long-time married couple enjoy a new pleasure with any knowledge you may have...

Thanks!

wonderingabout this
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wonderingaboutthis responded:
It happened again last night. I had just brought her to orgasm orally. She was very receptive to me caressing her anal area, and was definitely "in the moment". After applying some KY, I inserted a finger in as far as the first knuckle, and she was enjoying it and told me so. Then, suddenly, she said "I'm getting a sick feeling, but don't stop." But after just 15-20 more seconds, she started to gag and asked me to stop.

What is going on? I simply don't understand. I've waited so long for this, and she's excited about something new like this, but there's no way I want to have her go through this sickness stuff just for my pleasure.

Can anybody help, please?
 
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alaska_mommy replied to wonderingaboutthis's response:
I haven't had that issue myself, so I'm sorry to say I can't offer any insight.
Maybe someone will chime in who has had this happen...
 
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wonderingaboutthis replied to alaska_mommy's response:
Thank you for replying anyway, AM. I've wondered if it isn't an emotional response, nervousness, or fear of the unknown, etc. My dw has taken the positon over the years that her butt is off-limits, and only recently changed her mind and agreed to try it. I've talked with her at great length to try to determine if she's OK with the overall concept of anal sex, and she tells me she is. She says she doesn't view anal as gross or dirty or evil or any of the other negative things I have seen other women talk about.

I think the reason she's agreeing now is that we both admit to being pretty much in a sexual rut after 30 years of marriage, the excitement factor is pretty low for both of us. But I can't yet decide whether she's actually looking forward to anal sex, or if she's agreeing to it just for my benefit, and that still bothers me.

She's a conservative and "proper" person outside of the bedroom, but not quite as reserved when we're having sex. She openly masturbates, loves her toys, even has her clit hood pierced as well as pierced inner labia with 14k gold rings I bought for her. One thing she doesn't do well is play the "whore" or "slut" role or use raunchy language, which is OK with me, although I admit there are times I would like her to act a little "dirtier" in the bedroom.

She also has mastered female ejaculation, and proudly "squirts" during orgasm often, which I enjoy immensely.

I guess my point here is that while she's a "librarian" type woman in public, behind closed doors she's a more erotic person, although still reserved in some ways. I just have to wonder if this sick feeling or gagging is a psychological reaction to engaging in a sex act that her subconscious mind is actually telling her she shouldn't be doing.

I don't know, it's just disappointing after all these years of wishing for adding anal sex to our repertoire, having her agreeing to give it a fair try (at least consciously) and then having this pop up. As badly as I want anal sex with her, if it is something that she doesn't like or just tolerates for my pleasure only, I'd feel like a jerk afterwards. My real desire is how is was with my first wife, with her moaing in pleasure and having anal orgasms and actually asking me for anal sex (down the road, of course).

Alaska, if you don't mind, it sounds like you enjoy anal sex...how did it go for you the first time you were asked and agreed? I mean, was it difficult for a while or did you find it pleasurable quickly? I ask because I really want to introduce this to my dw in the right way, without added pressure or certainly without any pain. I know all women are different, but I sure would welcome any advice you might have to help me introduce this to my beautiful wife in the most comfortable way for her emotionally and physically that I can.

I can't really use my experience with my first wife as a blueprint for how to do this right. She was probably a bit unusual in that she actually brought the subject up - we were very young, she was only 17 (and pregnant) when we married, I had been her only lover and we didn't know anything about sex back then. Anyway, one day when I tried to engage her for sex and she had just started her period, she actually said "well there's another hole back there if you want to try that". Totally inexperienced, all I did was grab a big glob of Vaseline and simply pushed right in, with no pain or discomfort for her at all, and she became ravenous with pleasure almost instantly. The next time we tried it she actually had an orgasm from it, and for 7 years we had anal sex 2-3 times a week with her actually intiating it about half the time. I'm pretty sure my first wife was a bit on the unusual side in the way she adapted to anal sex instantaneously.

Thanks for any help or advice you can give us, and we sure hope others will chime in to help also.
 
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Jumper197074857 replied to wonderingaboutthis's response:
Your wife sounds very similar to my wife. Like yours, my wife is a very "proper" lady in public but behind closed doors, she tends to take on a different persona. She absolutely loves sex and willing and ready just about time (except mornings...she's not a morning person). She's like my "lady on the streets but a freak in the bed" However, that persona behind closed doors was conservative when we met. Over the years though, she's been willing to explore new ideas, techniques, positions, etc, including anal sex. We've only been exploring anal sex for about 3 years and its usually only two or three times a year. Despite our limited experience, I've learned to let her set the tempo, depth, duration, intensity, etc. She refers to this as "cleaning her hiney hole" but every so often in the shower, she'll insert my penis in her anus (with copious amounts of body wash of course) and will rock back and forth. I just stand there letting her go at her own pace. We've learned that she can handle about 3" of depth with very little discomfort and it's actually a little pleasurable for her.

So my suggestion would be, if/when you and your wife proceed with penis insertion, let her control everything and I mean everything. At the same time, apply some clitoral stimulation as well. My wife has found this makes the experience more enjoyable (or bearable...depending on who you ask, lol) those few times we do have anal sex. And last but not least, take it slow with your wife. What finally convinced my wife to try it was a Better Sex video on anal sex. It's very informative and when the movie was over, my wife was far less worried than before.
 
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alaska_mommy replied to wonderingaboutthis's response:
Well it sounds like you're going about everything in the right way, not pushing for it and starting slow with a finger and lots of lube. Also trying it after orgasm is a great thing too.
I'm not actually a huge fan of anal sex, it's more something I will do as a favor for hubby, even with that we haven't done it in probably 6 months. I don't know if it's just his size or my shape but it's always hard to get it in without discomfort for me. I sort of have to grit my teeth a little until things sort of relax back there. Then it does feel pleasurable but I normally take awhile to orgasm during sex, and since anal sex is a tight fit hubby will always orgasm before me. So basically we go into it knowing that it's just for him, although I do enjoy it some too. I hope you can get some better input, it really does sound like you're doing all the right things and in the right way. And kudos for not pressuring her at all.
Maybe try backing it up a bit for awhile, just by stimulating her externally instead of inserting your finger. Then you can try to progress if that doesn't cause her any ill effects.
 
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wonderingaboutthis replied to alaska_mommy's response:
Thank you both very much, AM and Jumper, I really appreciate your input.

After re-reading my last post, I know one thing I need to do is try to forget about the anal sex with my first wife, I can see now I'm subconciously hoping for an exact copy of the 18-year old I once was married to with my 30-year sweetheart, which is pretty unfair. The differences from one woman to the next are something I need to remember and my first wife was pretty unusual in the way she just adpated instantly and ravenously the very first try.

Funny, the anal sex was the only really good sex with my first wife, she was completely full of other hang-ups and not a very compatible lover for me at all. But boy was the anal tremendous (dang I did it again).

I can see we need to communicate alot more about anal sex, unfortunately talking about it sort of kills the mood before we start. I like the idea of backing up a little and just concentrating on pleasuring her anal area without entering her.

I didn;t mention it before, but there have been about 3 instances in the last 30 years where I tried to penetrate her anally, and like a total idiot in the heat of the moment I broke every rule in the book, not "warming her up" first, no lube other than her vaginal juices on my penis, etc. and the result was just as one would expect, painful for her and unsuccesful in every respect. I have discussed with her how dumb that was of me and assured her this time I would use the head between my shoulders first.

I think the only thing slowing me from going forward with her right now is myself and trying to be so careful I don't cause her any discomfort. I guess there's the possibility that I'm coming off so insecurely that it makes her unsure and nervous about the whole thing. I have never been overly aggressive or sexually demanding with her, likely to a fault. Maybe she'll respond better if I "take control" of the situation a little more firmly and just act as a bit more of a leader than being so careful that I'm ineffective in sparking any passion to the act.

I know I'm rambling all over the place here, sorry about that, I'm just sort of thinking out loud. I think tonight is the time to shoot for some passionate response from some external anal play and just deal with what happens rather than trying to analyze this to death and killing any mood involved. If it goes well, with her penchant for sex toys, perhaps a small vibrator will spark some pleasure for her and start the ball rolling. I just hope I can resist the urge to graduate to my penis right away. I'm pretty thick, and I imagine that part will take some careful and slow effort on both our parts.

I'll keep you posted, meanatime I'm all ears and welcome any and all ideas, comments, or other help....thanks again...
 
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Jumper197074857 replied to wonderingaboutthis's response:
It sounds like you're on the right track. As I mentioned, my wife was extremely hesitant and like alaska_mommy, my wife partakes in anal sex because as she put it, it's more for me. My wife did tell me last night however, the past couple of times have been more enjoyable than previous times mainly because she was in control. This past time (a couple months ago), we were in the rear entry position and I let the passion get the best of me and thrust a little deeper than I should have which did cause some pain.

If/When your wife wants to proceed further, allow her to take control. It may only be the head of your penis she takes in, but it's a start. Let her work her way up.

The one time my wife and I really went at anally, she eventually got to the point she was actually starting to moan loudly. I asked her later about it and she admitted it was starting to feel good. Problem is, there was some pain and discomfort to begin with and following, there was a couple of days of soreness. Will we ever do that again? I don't know. Time will tell. For now, I take what I can get

You say your wife enjoys toys. I would consider buying a double penetrating vibrator. Typically, the anal portion is small. Let her experiment with this. Might bring her to another level of curiousity, interest or whatever the case may be.
 
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Jumper197074857 replied to Jumper197074857's response:
One other suggestion/idea.

I'm not sure how you feel about this, but consider letting her engage in some anal play on you. Can be as simple as letting her insert a finger or going as far as using a strap-on. I told my wife if I ask/expect/hope/pray she does something for me, I should be willing to reciprocate. Fortunately, I enjoy anal play so it wasn't a big leap.

Just an idea I thought I would toss out there
 
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wonderingaboutthis replied to Jumper197074857's response:
Thanks, Jumper. Yes, actually we already do that. I enjoy anal play immensely myself and she already happily uses fingers, toys, etc. to stimulate me, without hesitation, including the harness. In fact, I have sort of been holding myself up as an example by saying things like "See, this feels so fantastic! I so wish you'd let me show you how good this can feel"...and actually that was likely the key to her agreement to try things herself.

As far as the toys go, I had thought about a double like you suggested. But she actually prefers a small vibrator on her clitoris over penetration with a toy. With the exception of when she wants to ejaculate, then she uses both the vibreator on her clit and a g-spot toy for the internal stimulation. Other than that, vaginal penetration isn't really part of her masturbation or our lovemaking routine with the toys.

Last night was pretty much a disappointment. I spent several quiet gentle minutes with the lights off massaging her external anal area and trying to arouse her in that way, to no avail. She was relaxed and totally cooperative, but said she "just didn't get anything out of it". I was so bummed I lost my erection and she ended up masturbating to orgasm with her vibe. (Which was totally OK with me). I tried to respark my desire through masturbation along side her, but no luck so I just went to sleep. The only positive reaction I've ever seen her have anally was from shallow penetration with a finger, and even then it was fairly marginal, with a very few exceptions.

We usually begin our sex sessions with some mutual masturbation, primarily because she takes a long time (sometimes 20 minutes or more) reaching orgasm and doesn't climax from penetration. I used to bring her to orgasm orally first, or with her favorite vibrator. A few years back she began having problems getting to orgasm from me stimulating her. It's become a case of her needing the stimulation in exactly the "right" spot, with exactly the "right" pressure and technique. So now, 99% of the time she first masturbates herself to orgasm with the vibrator, then we start the penetrative sex. It is very rare that I can bring her to orgasm orally or at all by myself, even using her favorite vibrator.

With that, there have been a few (rare) cases over the years where she was tring to reach her orgasm with her toy and gotten "stuck" (as we call it), and I inserted a slippery finger into her anus and she almost immediately went off. That is the kind of response I am trying desperately to find out how to get from her. Trying to find that combination where the anal play really does something for her. If I can figure out how and when that happens, that would represent my best shot at initiating anal sex. The problem is, it is such a rare occurance that I can't seem to find the key to repeating it. It doesn't always work when she's "stuck"...

I'm beginning to get impatient (in my mind only, I don't let it show) and I'm starting to think it might be time to give up on trying the anal foreplay arousal efforts. Maybe it's time to just let her have her orgasm so she's fully aroused, lube everything up, loosen and relax her as much as possible with fingers or a small toy, and try the direct apporach with my penis. If she's just not getting anything out of the anal foreplay, maybe just going for it (correctly this time) is the only way. I'm so nervous about getting to that step, because it represents the "make or break" time for the whole anal sex subject. If it's painful for her, I am sure it will be the last time I'll ever get to try. On the other hand, if it's as much as tolerable, it may be the beginning of what I'm looking for.

I still can't get out of my head how quickly and easily my first wife responded to anal sex and how much she enjoyed it. It seems I have two women on completely opposite ends of the scale here...sheesh...
 
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Jumper197074857 replied to wonderingaboutthis's response:
My wife was much the same way. She didn't derive much, if any, pleasure out anal play until one evening I licked her anus. She seemed to respond to that quite well. But not enough that she would entertain the idea of anal play with insertion. What finally broke the ice was we purchased a movie, at my constant and strong urging, called Better Sex: A guide to anal sex (or something to that effect). We watched it, her hesitantly, one evening. The video is more of an informative video with pointers, etc and interviews with real-life couples who engage in anal sex. It's not "hardcore" but more "soft porn" but again, it's more informative than anything else. Following the movie my wife actually admitted it didn't look or sound that bad and we could probably try it. A few days later we unintentionally (long story) engaged in our first anal sex experience. We're not at the point you and your first wife were at, nor do I think we'll ever get to that point, but it was a way for both us to explore this arena more closely. So that may be something to look into. The Better Sex series of videos are very classy and well made in my opinion.

And I would caution you on explaining how fantastic anal sex is based on your experiences on the receiving end. Remember, the prostate gland for men is our "g-spot". Women don't necessarily have that in their rectum so if she doesn't feel that same level of pleasure you do, she may be extremely disappointed and show absolutely zero interest in it in the future.

Are you and your wife drinkers? Does she drink wine? Reason (and by no means am I advocating getting your wife drunk or anything to that extent) I ask is this. One night a few years ago, my wife and I decided to have a few drinks at home. Not to the point of complete and utter drunkeness but enough we were definitely feeling the effects. After a while, we decided to jump in the shower in anticipation of what was to come (no pun intended). After a couple of minutes in the shower, my wife proceeded to give me oral sex. In times past, she would take me to the brink then stop. Teasing me if you will. But she never showed any desire, interest or curiousity in completing the deed orally. This night however, she brought me to the brink and when I told her (and she knew), she bore down on me and the next thing I knew...BAM! She didn't stop until I felt completely drained. She didn't miss one drop. I asked her what compelled her to do this and she said she just felt like it and the alcohol was a way for her to relax and let her inhibitions down enough to go for it. She said she had always thought about it but was scared, worried, nervous, etc.

My point is this, a glass wine or two over dinner may help your wife relax enough that she may take things a little further. She may be interested but her inhibitions, her preconceived notions about it, may be what is preventing her from going further or deriving any pleasure out of it. For all you know, she may think you'll end up getting doo-doo on your ding-ding

Bottom line really is don't feel frustrated. I know it's tough. Believe me, I honestly do. But hopefully, with the right coaxing, she'll eventually open up more to the idea.
 
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wonderingaboutthis replied to Jumper197074857's response:
The wine is a great idea, I forgot about that. I can't drink anymore due to a medication I'm on, but she enjoys a glass of wine now and then. In fact, we used to have our best sex after splitting a bottle together.

One rough part about being in a 30-year marriage is the "rut" we are in. While we used to go to great lengths to have a sensual evening, with wine and candle light and kissing and massages and hours of build-up, any more I'd have to say we both just go for the orgasm. It's like we're both saying "that's what we really need so let's just get to it". It's sad but all the sensual build-up seems almost foreign to both of us anymore and although we still try to be that way on occasion, it usually comes off like a play-acting role without the desired intensity ever taking place.

But in all the reading I've done on anal sex, I'm constantly running into comments on forums like this where the woman says "I like anal but usually only if I've been drinking" so maybe you really hit on something there, Jumper.

My wife has no fear of the dreaded "doo doo disaster", she's seen that it just doesn't happen with me, so I doubt there's any fear there.

What I do know for sure is that her attitude about trying anal sex seems just fine, she's totally into trying something new to spark our sex life, it's just that she's honestly not getting any physical pleasure from what we're doing. She's not getting turned OFF by it, but she's also not getting turned ON by it either, it's been just sort of ho-hum for her.

You know, I bought 2 books on anal sex for couples and a video too, and I honestly tried to get her to read them and watch the video with me, but at the time she was in her "no way" posture on the subject. I ended up giving one book and the video to a buddy who was trying to get his wife to try anal. It wasn't from the Better Sex series, but similar. They loved it, and now enjoy anal sex alot (which has me SO envious) I almost think though, that at this point a video or book would be perceived by my wife as something like "I don't need to see this, you've already convinced me to try, and I'm trying, so why watch the video?"

It's a tough set of circumstances. If she would just feel some pleasure from any of this, I know for a fact she'd be all for it, but so far, it's been like trying to turn her on by rubbing her elbow.

Probably the wine and a good hard orgasm first, then just going for the whole enchilada is going to be the only thing that will work - the proof in the pudding so to speak.

I do know that her g-spot orgasms are most intense and her squirting puts her in the "naughty" mood best and she stays extremely aroused afterwards and really desiring penetration. Maybe some wine, low lights, and letting her soak the sheets first will put her in the best frame of mind and physical neediness for an all-out attempt.

Now if I can just keep a sufficently stiff erection during all this lead-up under all this pressure...watch, she'll be turned on and ready as all get-out, and I'll get a soft attack...better break out the little pill first...
 
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Jumper197074857 replied to wonderingaboutthis's response:
The approach I took with my wife with the video idea, as transparent as it may have been, was to tell her it may give us some other ideas to try or ways to attempt it that we may not have thought of. My wife's whole thought process at that time was more or less, I'll slam it in, it'll hurt, I'll orgasm and she'll be left in pain and dissatisfied. No matter how much I tried to convince her otherwise, this was the idea she had in her head. Where I think the video really helped reassure her was seeing the women on the video who honestly enjoy and engage in anal sex. Seeing how they reacted to it, the approach they took and actually hearing their story, I think, is what helped ease her mind a little.

When we first got the video, my wife rolled her eyes and gave me a "Hmmmmmm" answer which I've learned there are two ways she does this. The first way means "Fat chance...not gonna happen in a million years...don't even bother wasting your time". The other way usually means "That's not a bad idea....I'll think about it...etc". The "Hmmmmm" she gave me when the video arrived was the "fat chance..still not gonna happen" answer. But once we actually watched the video, that turned into the second type of "Hmmm". The door was open albeit slightly. Nonetheless the idea was planted in her head.

So try an approach that lends itself to the idea of learning new tricks. Up to that point, I was trying things that I thought were working. Come to find out, they weren't and I actually learned a few things. One of the big things I learned from the video (and from reading this forum) is when inserting something, either a finger, toy or penis, if the woman pushes out at the same time as if she's having a bowel movement, it tends to make insertion a little easier. My wife has tried that it does seem to work.

Something else my wife and I have done in times past is I'll insert a small vibrator in her anally. She'll hold it in place and we'll continue on with vaginal sex. This had a two-fold benefit. The first is, her vibrating vagina! It's great! Secondly, she seems to enjoy vaginal sex more that way. Having said that, if you have a small vibrator no more than 1/2" in diameter, you might consider using that.

Another option is to search out and purchase a small vibrating butt plug. Not only is it something you can use on her, but it's something she can use on you

What I'll do is when she's masturbating with her toy, I'll concentrate on her anal opening. I'll lick it, rub it gently, massage it, etc. As she nears orgasm, I'll begin to add a little pressure to the point my finger is inserted slightly. What I've found is during ther throes of passion from orgasm, she'll actually press back on my finger and if she's on all fours, she tends to rock back onto my finger. Next time your wife has a g-spot orgasm, you might try a little anal play at the same time and see how she responds to that.

Speaking of fingers, and this probably goes without saying, make sure your nails are closely trimmed!! And if you have rather fingers, try using your pinky finger.

All in all, what I've learned most about anal sex and my wife is the more I push the idea onto her, the more turned-off she is about it. I still incorporate anal play into our normal sex life but it's limited to licking, gentle massaging, minor insertion of my finger, etc. The best advice is to take things slowly
 
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Jeremy3456 responded:
I can't speak for your wife but as a male I had an experience with anal sex several years ago. I was having a short-term relationship with a woman who was very sexually excited in the bedroom. She was more experienced than me, although i'm no prude, but she had trouble coming to orgasm even though she could maintain arousal for quite some time. One time in a sexual frenzy she took a dildo and inserted it in her anus and wanted me to hold it and insert it back and forth. I did, but the sight of it actually made me nauseated! That was surprising to me. I had never thought about anal sex (giving or receiving) and I guess in my mind I associated it with bring dirty or gross; I don't know. Maybe just the sight of something so "unnatural" (to me at that time) seemed like a violation of the body somehow, the way other things (like seeing a wound or vomiting for example) can make you nauseated. I also associated anal sex with gay men which turned me off.

However, I've always learned and grown from every sexual relationship, as I think everyone does, and my repertoire has expanded. My present girlfriend has a history of enjoying receptive (and I guess giving) anal sex. She did it to me with a dildo a few times, which was new for me, and for the most part I enjoyed it. And I enjoyed the fact that she enjoyed it. It takes some lowering of inhibitions for sure. Anal sex is certainly not just for gay men!

I understand and empathize with your need to have her enjoy it for real and not just do it for your sake; although another poster saying that she does it mainly to satisfy her husband works well for them. I'm of the belief that sex often has to be a bit nasty or obscene for the inhibitions to go away and to be enjoyed. Maybe your wife never will love anal sex, or put another way, maybe she is exploring the enjoyment of the helplessness or the "rape" quality to it, which is what I did when my girlfriend did it to me. It was kind of a role play where she was dominant and I was submissive. It is fun to release and let someone else have their way with you---you almost become a voyeur into their private sexual world even though you're participating in it. Just maybe that's what your wife is exploring now as her sexual repertoire expands.

Perhaps a little alcohol would help your wife, or as another poster said, look at videos of it together. But if you and her are self-aware and comfortable and articulate in talking about your emotions and reactions, I would try to find out what feelings and thoughts she has, or wants to have, during the actual act of anal sex. Maybe she doesn't want to openly, emotionally share every second of it with you during the actual act, but wants to go into a private emotional world momentarily while you are doing the penetration. In that case you could set up a role-play type of situation to facilitate her. That would be better than you asking her 'is this allright? Does this feel good?" during the whole time. That's just a thought.

And I'm sure we would appreciate a progress report at some point! Good luck!
 
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wonderingaboutthis replied to Jeremy3456's response:
Friday night went by with some real progress, and I'm both excited and proud of my wife's efforts. We had a conversation on Thursday in which I told her I think that due to her getting no real pleasure from the external anal play, I thought we should just go through the process of "getting her ready" and trying anal penetration. Her answer was that she thought it would be best if she tried some fingers and toys first without me present. I was thrilled by this comment! I gathered all the possible anal toys for her to try (mostly mine) and disinfected them all throughly.

I got the video back from my friend, and asked her if she wouldn't mind watching it with me, which she said "Sure!" The video is by Tristan Taormino, and starts with a workshop group in which Tristan has two women going through the process of "warming" one of the women's anal area, insertion of first fingers then anal beads then butt plugs, with the lady receiving the play stimulaing her clitoris at the same the through orgasm. I was a little concerned here, becasue my wife does not care for porn with two women but that part seemed to go just fine.

The video then went through a male-female couple going through the process and having anal sex in several different positions and ending with both the patricipants having orgasms. It was narrated thoughout with instructional comments as the couple went through the process. The video didn't seem to arouse my wife (her hands didn't wander to her genitals which is the norm when we're watching porn). I picked up on that and as difficult as it was, I didn't reach for my own although I would have liked to - the video was very arousing to me.

Then after a glass of wine, it was bedtime, and I asked her if she'd like time alone in the bedroom first and she said yes. After about 20 minutes, she called me into the bedroom and I found her masturbating with a small butt plug in her rectum. I was thrilled at this, she actually said it was enjoyable, not in a huge sense, but she did find some pleasure. By then I was very ready to try penetrating her, the visual of her with the butt plug in was something brand new and incredibly erotic to me.

She related that she started with fingers, which was no probem at all, no "sick feelings" nothing negative, then graduted to the long slim butt plug. I just let her call the shots, I watched only as she masturbated with her vibrator with the butt plug in, to a very intense clitoral orgasm. Then she said "that felt great, but you're awfully big and I don't think I'm ready for your penis yet. We need some larger toys first" In my mind I was disappointed, but not wanting to mess up a good thing, I gathered myself up and we finished with missionary vaginal sex with the plug still inside her. After my orgasm, she again masturbated to a gushing g-spot orgasm with me stimulating both her g-spot and her anus internally with my fingers. We really made a mess!

I see no hesitancy to move forward, she did have two amazingly good orgasms with the butt plug inserted, that calmed my fear that she might just be doing this for me. Afterwards it wasn't "Oh wow let's go out and get these new toys tomorrow" but everything went smoothly and matter-of-factly without any hint of "this is crazy, I don't want to do this".

She loves sex and her orgasms, the best part here is I don't see any fear or "anal sex is dirty or wrong or gross or evil". She even had placed a towel under her in case she ejaculated, so she was planning on orgasm from the start.

Now more than ever is when I need advice! I am so anxious to move forward to the actual first try of my penis in her tush, and I want to rush right out to buy the butt toys she wants, but I'm caught as to how rapidly to progress. I guess I worry that if she just continues to masturbate with a small toy in her butt and getting these intense orgasms, that will end up being the destination for her rather than a step in a journey. She does love her toys!


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