How To Prepare For Anal Penetration: The ULTIMATE Guide

[brnsuga]

Re: Nothing insightful to add, but desperate

My wife and I have been married since 1996


We have tried to have anal sex, but she says I am too big. I know that can't be the reason, because I'm only 7 inches around.
but she says it hurts. Even my finger hurts her when placed inside.

Eric:
A finger might hurt during anal penetration and there may be some discomfort while the finger is still inside, but for it to actually continue to "hurt" could indicate a medical problem (she could have a ruptured sphincter which would need surgical repair and, after a period of healing, she would be pain free!). It might be helpful if you go see a specialist (a colon surgeon can do a scan of the tissues and identify the problem very easily). Make sure you go with her to the appointment for moral support.

Of course, my sphincters are in fine and dandy shape and after you described the circumference of your "equipment", I sort of lost my train of thought. For some of us, just the idea of a dick the size of yours in our ass really gets our juices going,... I'm just sitting here in a puddle.

Hope everything comes out O.K. for both of you.

 

[Freya]

Hey sexy peach... how YOU doing?



PBW

Good. Fighting a union war on the other board, so I'm keeping amused anyways.

We'd better not hijack another thread or they're going to tie us up and punish us severely.

 

[Freya]

Re: Re: Nothing insightful to add, but desperate

Eric:
A finger might hurt during anal penetration and there may be some discomfort while the finger is still inside, but for it to actually continue to "hurt" could indicate a medical problem (she could have a ruptured sphincter which would need surgical repair and, after a period of healing, she would be pain free!). It might be helpful if you go see a specialist (a colon surgeon can do a scan of the tissues and identify the problem very easily). Make sure you go with her to the appointment for moral support.

Of course, my sphincters are in fine and dandy shape and after you described the circumference of your "equipment", I sort of lost my train of thought. For some of us, just the idea of a dick the size of yours in our ass really gets our juices going,... I'm just sitting here in a puddle.

Hope everything comes out O.K. for both of you.

Just to add to Pure a bit, first let me say I completely agree with her last point.

It could also be something as simple as hemmorhoids or anal fissures (which can be serious if they worsen). I have these and at times it makes anal sex very uncomfortable for me. I usually need to be in a certain position, at least to start with.

 

[SexyChele]

Re: Nothing insightful to add, but desperate

My wife and I have been married since 1996

The thought of anal sex arouses us both. She really enjoys laying on her stomach while I oil between the cheeks of her ass and fuck her crack, the head of my cock teasing her hole on the upstroke and the feeling of my shaft sliding all the way up

We have tried to have anal sex, but she says I am too big. I know that can't be the reason, because I'm only 7 inches around.
but she says it hurts. Even my finger hurts her when placed inside.

She loves to have it licked and flicked and teased, but we cannot get past the pain during penetration.

I read an earlier post that it isn't supposed to hurt if done properly.

We both want this, but the pain she endures makes her try less and less often

Any help here?

**
Eric

PS Oddly enough, I can take pretty much anything with little or no lube GO FIGURE LOL

Well, first, 7" in circumference would be the same as my wrist. If this is true, then all I can say is - you will probably never achieve anal with a majority of women. (That was more tongue in cheek than anything else) I've never met a man who was that, though a few told me they were. Point is, I'm with PB. I think it's doubtful (though I could very well be wrong, I know). Besides, I have an anal plug that truly is 6" around and can take that - although there is a little pain involved getting it past the sphincter. Once in place, however, no pain.

Just from the information you've given us, my first question would be: what are you using for lube? You say oil, and I know that baby oil is sometimes what a lot of couples think to use. Not always a good lube - very thin and evaporates into the skin. And I would stay away from Astroglide for the same reason. It sounds as though you need a thick lube, and no, do not use petroleum jelly. KY can be good - but be prepared to use a LOT of it. There are products sold in adult stores and online that are silicone-based and used expressly for anal play. It is very thick, does not evaporate, and can be a bit messy. (It is not water soluble) Could be, you need to use that.

Now, for a finger. Be certain she is relaxed and in a position that is comfortable to her. Having her on her stomach, as you describe, is good, but be certain you can access other areas of her body that can make her feel good as well. You might need a bit of a distraction to make this work. Use the smallest finger you have - even your pinky if that is the smallest. Lube both your finger and her anus. Use what you think might be comfortable - and then double it. Okay, now add even more. Getting the picture? Be certain you play with the area first, while also stimulating her clit, or have her rub her clit herself with either finger or vibe. Tease a bit, run your finger around the rim, tap against it. Be certain you or she is paying good attention to her clit while this is going on. Then, when you want to enter her, tell her to push out as though she is having a bowel movement. This step is the most important one of all and the least known. When she pushes out, it relaxes the sphincter muscles and a finger that is extremely well-lubed pushing into an extremely well-lubed anus should slide right in.

Do NOT begin moving once inside of her. Just let the tip of your finger sit there. Let her get used to it. Sometimes women will say it "hurts" when in reality it is pressure that they are feeling. If she says it does hurt and she cannot take it, tell her to push out once more, and as she does so, gently slide your finger out. If she allows your finger to stay, continue applying lots of attention to her clit. Keep the lube at the ready, and apply more if needed. Slowly, slowly, slowly, slowly.....did I say slowly? slide your finger deeper. For the first time, I would stop at the second knuckle. Rather than doing a back and forth type of thing, move it around in a circle, slowly and gently. And don't forget to keep rubbing that clit! If she has an orgasm during this, be prepared that her anus will tighten up, usually more strongly than her vagina will, and cease movement. After she orgasms, gently tell her to push out and remove your finger. (Remember, this would be a first time experience. You may need to build up tolerance over a period of time with her.)

Once it is over, talk to her and find out what she liked, what she didn't. Discuss what she wants in the future, etc.

As far as anal fissures or hemoroids go, it is wise to seek medical help. But first, does she have any other symptoms? Symptoms for anal fissures include extreme pain with bowel movement and bleeding. (A fissure is a tear in the tissue, usually caused by constipation, but can also be caused by anal sex where things get a little more rough than usual) Hemoroids depend on whether they are internal or external. Internal will normally cause painless bleeding. External hemoroids can be seen, and are aggravated in circumstances such as standing or sitting for extended periods of time. They also include itching, burning, and swelling. If she doesn't have any of these symptoms, there might still be a problem, but people with anal fissures and hemoroids are usually experiencing symptoms without anal sex thrown in. Plus, it is very difficult for many women, if they symptom free, to go to their doctors and tell them they are trying to engage in anal sex and it hurts. Granted, most doctors have heard it all, and I've talked to mine about it, but most "anal virgins" might resist being put into that type of situation. (Now, if your wife is experiencing any of the symptoms described above, she should see her physician!)

Always keep in mind that some women just can't do anal. They may want to, but there might be deeper reasons holding them back. It happens.

My last suggestion would be to have your wife try to insert her own finger into her anus. With as much lube as possible, naturally. She can determine her own level of pain and pleasure and knows when she needs to stop and start. This can help you learn, and it might give her a greater level of comfort as she is in control of her own body.

Good luck!

 

[DemonicAngel]

Question?

When is big too big? How much girth can a girl take, how much length?

 

[SouthTampaGuy]

SexyChele and Freya

Thanks for the help. She may need to go to the Dr as she complains that her BM hurts at times if it is too large. Perhaps she just has a smalll sphincter. I don't know

I think the girth issue is a getting a bit exaggerated. PS Thanks BrnSuga for your thoughts! Can you measure circumference the same way you measuer a straight line. We're using the same instrument, a sewing measuring tape and it's 7 1/2 long and 7 around. but if you look at it in those terms, that's almost a square.
But when I take my thumb and forefinger and wrap it around my writs (below the epicondyle of the radius and ulna and above the carpals) I get the same as when I wrap the thumb and forefinger around my shaft. ANy math wizzes out there who can authenticate the correct way to measure girth?

Sorry I got so far off topic. Can someone throw me a life jacket and I'll just wade my way back to topic.

**
Eric

 

[brnsuga]

Sorry I got so far off topic. Can someone throw me a life jacket and I'll just wade my way back to topic.
**Eric
[/B]

With a dick like yours,baby, you ARE the topic. And there are quite a few of us who would follow you anywhere you would want to take it. Second thought, why don't I get in front and YOU follow ME instead....

Closer;......Come closer, baby;.....NO, we can't wait till we get HOME and do it. I need you in my ass right NOW, baby. If we stand over here like this, nobody can really see what we're doing.....That's right, put it in there for me, baby...... Give it to me harder baby......I need it harder, baby.....FUCK YOU, YOU BASTARD! You're wasting my fuckin' time. Don't you even KNOW how to fuck a girl's ASS?.......A-H-H-H-H-H!......Oh,that's it, baby.....You're hittin' it now, baby,.....Damn, baby, that hurts SO-O-O-O-O fuckin' G-O-O-O-O-D.....Stroke it, baby.....WORK that ass, baby.....HARDER, you fuckin' bastard.....That's right baby, talk to me......Come on now, talk to me.....Tell me what it feels like, baby......U-m-m-m, work that ass for me, baby.

OOOps. I sorta lost my train of thought again.

Before I got sidetracked, my original reason for posting this message was that it seems you really like the idea of having anal sex. Can you tell us some details about some of the anal encounters that big pretty dick of yours has had? Did any of the girls live to tell about it? More importantly, did they come back for seconds?

Much appreciated,
brnsuga

 

[SouthTampaGuy]

BrnSuga

I myself have never had anal sex
Well, let me clarify. i have never GIVEN anally

I am however quite adept at receiving, but that is another thread for another board LOL

**
Eric

Email you some pics? PM me

 

[Guest]

Seconds, and thirds and fourths and . . . .

My man is large (ahem) and very thick. The length is good, but it is his thickness that makes me orgasm soooo powerfully.

It took some time, patience, practice, tongue, toys and lube before I could comfortably take him.

But now I can . . .


(which is one of the reasons I'm so happily married . . . )

 

[zipman]

While the physical advice has been very good, I don't think enough attention has been paid to the psychological side.

Most of the time, even women that love anal need to be in a relaxed state to enjoy it. The psychological as well as physical state of relaxation of the receiver is critical to even be able to enter some one else.

I think patience, discussion and massage can all help, but the bottom line is if she is scared or not ready yet, that fear will cause her to be tense, and make anal intercourse either impossible, or painful.

Good luck!

 

[Marquis]

God, topics like this really make me wish I had a bigger penis.

 

[P. B. Walker]

God, topics like this really make me wish I had a bigger penis.

You aren't the only one.

PBW

 

[Marquis]

You aren't the only one.

PBW

Could you imagine going around with a 7" penis circumference and thinking its small? I feel like punching this dude in the face.

 

[P. B. Walker]

Could you imagine going around with a 7" penis circumference and thinking its small? I feel like punching this dude in the face.

lol... well I don't quite feel like that.

I just think he's try to kid himself and not be too "cocky". Pun intended. I think if you have a big dick, you are allowed to say it and act like it. LOL

PBW

 

[Freya]

Ok, I have to come clean. I have a big cock.










Well actually I wish I had my hands on one, but fantasy will have to suffice for now.

 

[P. B. Walker]

Ok, I have to come clean. I have a big cock.


Well actually I wish I had my hands on one, but fantasy will have to suffice for now.

I told ya you'd get attached to that strap-on if you picked it up!! lol.

Yanno, I read something that brnsuga posted, about thread in the Amateur Pic section... something about a big Black Snake thread... LOL.... Will that give ya temporary fix until you can find a dude with a biggun?

PBW

 

[Freya]

I told ya you'd get attached to that strap-on if you picked it up!! lol.

Yanno, I read something that brnsuga posted, about thread in the Amateur Pic section... something about a big Black Snake thread... LOL.... Will that give ya temporary fix until you can find a dude with a biggun?

PBW

He does have a big one. I've seen some of his pics before.

Not my type though. I like my men cuddly, sweet and kinky. Size is irrelevant if they know how to use it, and how to write interesting fantasy scenarios.

 

[P. B. Walker]

He does have a big one. I've seen some of his pics before.

Not my type though. I like my men cuddly, sweet and kinky. Size is irrelevant if they know how to use it, and how to write interesting fantasy scenarios.

He could be cuddly and sweet... lol... never know.

I went and looked... that thing looks like it could hurt people...

PBW

 

[brnsuga]

God, topics like this really make me wish I had a bigger penis.

Marquis:
"IT'S NOT THE WAND, IT'S THE MAGICIAN"

Do me a favor. We are on page 3 of this thread. Scroll up to my post in the middle of page 3 (about 10 messages before this one, the one that starts with me telling Eric "With a dick like yours, you ARE the topic") and re-read that second paragraph which is a transcript of an actual anal encounter I had.

As you re-read that paragraph, does it sound like I am enjoying myself? Well it might interest you to know that statistically, in terms of size, that man had a small to average size penis. It was his technique, not his size, that made him so-o-o very good (he always withheld the kind of thrusting he knew that I liked until I begged him for it, he always talked dirty to me because he knew that I just could not enjoy any sexual encounter without an ongoing two-party commentary on the action).

Conversely, the man with the largest penis I have ever had inside of me really did not satisfy me sexually. He's a great guy and he is truly in love with me and I love him too, but we now have a platonic relationship because sexually, he just doesn't do it for me. Big penises turn me on and I like that feeling of fullness but that doesn't necessarily mean that the person who possesses that equipment knows how to satisfy a woman.

In fact, a really large penis makes one of my favorite sexual techniques impossible to perform. I really like "milking" a penis (just before a man cums, I get on top and without any thrusting motion at all, I make him cum by flexing my vaginal or rectal muscles - first at the base of the penis, then in the middle, then at the top - and then repeating this process until he cums). You can't do this with a really large penis inside of you because your muscles are too stretched out and you can't really flex them as effectively as you would like.

I totally agree with "Freya2"'s earlier comments and again I say that, even though big penises can be a turn-on, "IT'S NOT THE WAND, IT'S THE MAGICIAN".

P.S.:
PBW: Were you turned on by those pictures of "Black Snake"'s tool? I'm sure that everyone on this thread would love to see pics of "Black Snake" introducing you to the joys of anal sex!!!!! I'll even supply the lube for free cuz you will be needing a lot of it!!!

 

[SouthTampaGuy]

I was just going to ignore this

It's Sunday and I do nothing all day, but sit in front of the TV and watch football from 9am until after midnight.

It's my thing

But since I started the Lit boards a week ago, I wanted to break my routine and see what was going on in here

Marquis, were your comments re: your desire to punch me I never said I was small. I knew it was thick, but to want to punch me because I presumed to assume that based on the what, thousands of guys that are on Lit, that I have something to brag about. We're all guys here. Have we really not progressed far in adulthood that deep down we're still high school kids comparing dick size.

Man, if you were kidding. Cool. If you weren't you are officially the first rude person I've met here. Sorry I'm not posting all over the boards boasting about my cock size. Thinking that makes me somebody. My mind and my sense of humor make me what I am. No woman I have ever been with has ever been with me solely because of the size of my cock. Hell, they never even know until our realtionship hit that stage. I am on such a rant right now, I need to quit typing because deep down I have a feeling that Marquis was just being facetious and I am putting my foot so far in my mouth right now


**
eric

 

[brnsuga]

Eric,
I would never presume to answer for Marquis, but I will say that when I read his post, it appeared to me that he and PBW were just joking back and forth about the size of your cock and it was all said to amuse the viewing audience (which, at least in my case, it did). I do however understand that you are probably more sensitive on this issue because of the attention (both negative and positive) that your cock has attracted in the past. You seemed to be expressing some real emotions in your message and I am sorry that those comments bummed you out.

But, as you will see, there's a lot of joking which goes back and forth on Literotica. For example, in my most recent post (2 messages before this one), I challenged PBW to have sex with "Black Snake". I have never read anything which would suggest that PBW has any desire to have sex with a man. It was just a joke (of course, if PBW DOES get turned out by "Black Snake", then he would have me to thank for helping him discover a whole other side of his sexuality, huh?!) And, guess what?; here comes another example of my attempt at humor:

Since "Black Snake" is so well-endowed (his pics are on the "Amateur pics page), I'd like to ISSUE A CHALLENGE to the readers of this thread: Would anybody (male or female) like to compete for the chance to be "Black Snake"'s "bottom" ? Submit your entry on this thread. Your entry should be titled "WHY BLACK SNAKE SHOULD CHOOSE ME" and you should specify why your rear end is the best qualified to handle his big tool. (If your resume qualifications are not that strong, your ability to beg most effectively will also be taken into consideration.)

Yes, IT's A JOKE!!!!! But we might get some interesting answers. We'll see what develops.

Peace & Luv,
brnsuga

 

[Marquis]

Well, actually I think that both Eric and Brnsuga both took my comments way too seriously. While I would like a bigger penis, its not something I stress about too hard, and I do have a lot of confidence in my technique. I was just using a little self deprecating humor. So while I appreciate the small penis pep talk, its really not that necessary.

And Eric, I don't really want to punch you in the face, I was just kidding around. But don't worry about putting your foot in your mouth, it can be hard to read people's tone online a lot and I should've done a better job of showing that I was kidding.

Anyway all, no harm no foul, right?

 

[brnsuga]

Well, actually I think that both Eric and Brnsuga both took my comments way too seriously. While I would like a bigger penis, its not something I stress about too hard, and I do have a lot of confidence in my technique. I was just using a little self deprecating humor. So while I appreciate the small penis pep talk, its really not that necessary.

And Eric, I don't really want to punch you in the face, I was just kidding around. But don't worry about putting your foot in your mouth, it can be hard to read people's tone online a lot and I should've done a better job of showing that I was kidding.

Anyway all, no harm no foul, right?

Marquis,
You are so correct. The response I posted yesterday on the subject of "Its not the wand, it's the magician" does read as if I am trying to console you because you have a small penis. That was not at all my intention - sorry about that. I actually intended to be speaking in general about the "size" issue because from the message I posted to Eric, some readers might have gotten the impression that all I was interested in was a guy with a big penis. I was attempting to correct that misconception.

From having read your posts, you sound as if you graduated at the head of your class at Magician's School.

Life Lesson:

A GOOD MAN IS HARD TO FIND.
A HARD MAN IS GOOD TO FIND.

And so in that vein, I should start working on my entry into the "Black Snake" contest which started earlier today...

As Always,
brnsuga

 

[Marquis]

LOL, just call me Harry Potter.

 

[P. B. Walker]

P.S.:
PBW: Were you turned on by those pictures of "Black Snake"'s tool? I'm sure that everyone on this thread would love to see pics of "Black Snake" introducing you to the joys of anal sex!!!!! I'll even supply the lube for free cuz you will be needing a lot of it!!!

Nah, not really turned on. It was more that feeling of... well, like watching a car wreck. It was kinda weird and nasty and you're glad it's not you... but ya just can't look away. lol. I'll give ya another example, have you ever stood next to a real 7 foot tall person? It's just odd. You feel weird and out of place. So, sorry, no, not turned on.

And, no introductions are necessary... lol. I'd rather remain a stranger to that.

PBW