(NSFW) First time anal sex?

Best tip: Lady on top the first time, you dirty effer! Lol! It’s nice! };p

Anesthetic lubricants are not a good idea. There can be skin trauma (read: tearing), that she may not feel with the anesthetic. She needs to be able to be in tune with what she is feeling so that you can adjust your pace and depth accordingly.
A glass of wine beforehand might not be a bad idea. She definitely needs to be relaxed in order for this to be pleasant, any tension she is harboring can manifest in a painful way for her. I think the two most important things to keep in mind that you’ve read are : lubrication and start slow.

Woah, keep it greasy so it goes down easy. You sound like your performing serious medical surgery. Your probably a lot smarter than I am, so I am going to just keep it real with you. If she wants it, give it to her. As long as your not huge, it is pretty easy. It helps if they participate in getting the area ready by using her hand and trying to relax the area. Now you can just shove it on in, and it will hurt her a little but that goes away and you can go at it. But I suggest using the retard method, where you use just regular lube, and take your sweet ass time. She should dialate her ass before you penetrate, that way there is less pain. And don’t trip, it feels fucking great.

Have her get an enema first.
Use KY (the jelly, not the state, though I understand anal is very popular there).
Having her bent over, on her knees, while you are standing will allow more control.

@truecomedian “it will hurt her a little bit but that goes away”

Are you KIDDING?

@filmfann No. You’re in more control from the bottom with the lady on top the first time, which allows for easier penetration. You’re right about the KY though!

Pretty much summed up great by @TheOnlyNeffie, but to reinforce, Lubrication and Slow! You need lots of lubrication, and to reapply if necessary. It may not be, but keep it around in case. The anus is very sensitive, and so that can make it very interesting and good for the receiver, but also carries danger, so be slow and careful.

And yeah, anesthetic lubes are perhaps the worst idea for this ever. Well, not the worst, but it’s up there as far as well meaning disasters go. The key to success is her being relaxed but in control, and she needs to feel to do that. And plus any anesthetic will take away from the pleasure, so that’s silly.

Lastly, communication is also very important. She needs to tell you what she’s feeling, good and bad and everything else, and to tell you what she wants you to do. After the first time it will be easier and you’ll know better what she wants, but the first time particularly she needs to clue you in.

So, i realize i may have made it sound too complicated, so don’t take it that way. Just, lubricate, go slow, and talk, and it’ll turn out great, most likely. Also, her on top may also be a good idea. I haven’t tried it, but again she’s the one who needs to be in control, and that’s one of the better ways to assure that :-)

and, again agreeing with @TheOnlyNeffie. ‘Now you can just shove it on in’ is perhaps an even worse idea than the anestetic, and can easily end up with you guys in the ER with a bleeding anus.

Relax, it’s not a big deal – I highly recommend giving her a huge orgasm prior to anal, it’ll aid the body in accepting the process. Go slow, if she says stop, don’t randomly pull out, it’ll hurt more that way, just wait and see if it goes forward – and don’t freak out if you can’t get it done the first time, sometimes one’s body and mind want it but it just doesn’t happen, there’s always next time.

Use a toy first. Like a GI-Joe…

No just kidding. About Joe.
Use a toy (dildo), this way you can focus on what she can handle and likes. And you don’t have to focus on using your tool.

@truecomedian She’s a very small lady and I’m, errr…rather large. I don’t want her to experience any pain at all. She wants me to do this for her but she trusts that I won’t hurt her.

@TheOnlyNeffie I want her to be relaxed. Maybe warm bath, massage beforehand?

@filmfann Will the enema help her to relax?

@Simone_De_Beauvoir That sounds good, she loves cunnilingus. We’ll take everything very slowly.

@ChazMaz That’s what I was thinking of doing at first, using smaller “plug” toys or maybe just a finger to start with.

We’ll stay away from the anesthetic lubes. Some of my reading on this was contradictory.

And be prepared for ass truffles. Sometime, just part of the game.

I just realised that I should not be eating and reading this thread simultaneously. Thanks @ChazMaz
@stranger_in_a_strange_land that sounds like a very good idea.

Yeah I got Troll dick too. Just keep her asking for it. You can do it.

ass truffles??? eeeew

never go back to vaginal sex unless you have bathed and disinfected. Ecoli could be spread.Unless condoms are used.

try the finger first.

@TheOnlyNeffie Sorry to upset your meal. I only posted this on Fluther after much thought. I wanted to get answers from people I feel I can trust and realize how much I care for this lady’s well-being.

@jazmina88 Good point, I don’t want to cause her any infections.

The enema will keep pudding off your D-ck. Mostly. You want her lower intestine and rectum empty before trying this.

@stranger_in_a_strange_land no no, your question is fine. :) Promise.

“ass truffles” was just an interesting phrase to read while taking a bite.

@TheOnlyNeffie Bon Apetite!

[mod says:] Hey guys, let’s reel in the one-liners. Try to answer the question and be helpful. Thanks.

@Simone_De_Beauvoir good idea for the vaginal orgasm first. This will make her not only more receptive but really hot for whatever comes next. Lube your finger good and start small. Lube your d-ck and go slow. Like REAL slow especially if your bigger than average.

take your time (fingers and tongue circling the area) before putting it in slowly

Before actually having anal sex you might want to practice giving anal massage a few times prior. If she has experienced any past traumas anal massage can be healing and make anal sex less intimidating. It is also a very tender bonding experience.

The most loving and practical instruction I have ever read about anal massage is in the book Tantric Sex for Women. She calls the massage “Rosette-rose Massage”. There is some fluff in her writing but the practical steps she suggests are very insightful and gentle. If you can read beyond some of her spiritual theorizing I think you may find the book helpful.

Two questions:

First, how well endowed are you?

Second, how big is she?

And, where are the crackers?

No longer following. I’m out

Smoke some crack, that’s what did it for me.

@liminal Yes, I want to approach this slowly and gradually. I’m only concerned for her pleasure and not traumatizing her in any way.

@KatawaGrey She’s 5’3” 105 lbs; I’m 6’5” 240 lbs and body parts in proportion. That’s why I want to do this slowly and gradually for her. Probably not even trying for intercourse the first time.

@jjmah I want her to be as relaxed as possible. I’ll try that.

@truecomedian We’re not into drugs.

Geez recognize a joke, ok no more jokes, it’s not like I can hear anyone laughing. I try and make people laugh, that’s my flaw. It’s not easy to come up with this shit.

@truecomedian I laughed.

@stranger_in_a_strange_land: Ah, yes, you two have similar proportions to me and my boyfriend. My best advice would be to start out very very slowly. If you don’t want to use toys, use your finger, a single finger, for a while. Let her get used to that then maybe graduate up to two fingers. Also, use lube, lots and lots of lube. Just to be clear, this is all in the same session. Also, be prepared for having almost no fun the first time. In order for her to get comfortable and for you to keep from hurting her, you’ll have to have at least one practice session. Tell her to relax. If she tenses up at all, it’ll hurt. She might be able to tense once you are inside of her but before that, it’ll make things very hard. You also might try missionary. My SO and I have done this before and it actually worked pretty well. Good luck!

@Akua
I like the idea of pushing a few buttons and making people have sex in the butt, now I know what Dr. Strangelove felt like

@KatawaGrey I was thinking of using smaller plug-like toys at first, to help her get used to it, then gradually moving up in size until she can comfortably accept me.

I don’t have much to add here, but from personal experience we had an easier time of it after she had an orgasm.

@ChazMaz Re: “Use a toy first. Like a GI-Joe…” What’s wrong with a shoe stretcher?

That for the vagina.

And I mean the old school Gi-Joe.

@stranger_in_a_strange_land I think it’s a good idea. I can’t think of a non-rude way of saying it, but if you can stretch out the rectum a bit it’ll be easier.

I don’t suppose anyone’s seen the movie Finding Bliss?

@mrentropy Haven’t seen the film. That’s the general idea I’ve been thinking of, gentle stretching.

Try it out on yourself first, see how it feels… then you’ll know for sure how to tackle this, besides, it might open a whole new side to your relationship.. :-/

Just remember what the rectum is for. If it’s stretched too much, then the power of its purpose is diminished…which may not be realized until some years. Then, it’s “Depends”. hmmmm.

I love anal but it can hurt if done incorrectly. an enema is a great idea. an enema can be something that eventually you guys may use as part of the foreplay, together, but she may be squeamish and embarrassed about that, so i would advise letting her do a few Fleets about an hour or two prior so she’s cleaned out and evacuated, and has no fear of any shit going anywhere it should not.

my recommendations are, as someone else said, maybe a drink or two will help her relax. have the lube and use your finger to just rub her anus (and rub her vagina too, so she’s so horny and ready). rub the anus and then start applying pressure to it, so your finger gradually goes a little at a time inside. remember lots of lube (if she can lay on a towel or something that will help save your sheets). then after the finger has gone in and out a bunch of times, you can try plugs to increase the size she can tolerate, or you can go right to the penis. i like to be on all fours when doing anal, i feel like it makes me open. put her on all fours and push her shoulders down as far as they can go so her ass is sticking up in the air. continue with finger, lube, in and out and then replace it with your penis. rub the penis up and down her crack to make her want it, and then just like with the finger, slowly, pressure – push it in. push it in deep and leave it there. don’t pull it out yet, just leave it in and get her used to having it in there.

i think anal actually hurts less when the head of the penis is deep inside me, it’s when the head pulls out that i think it hurts the most. so leave it in deep, for a minute or two, and then slowly pull it out and start the in an and out. if she needs more lube, pour it on.

i think if you follow my advice you will find you’re both two new anal fans!!

Well I can’t add much then what everyone else has. Maybe watch a porno that has some anal in it. Boy! I must say there is a lot of sex questions tonight. Fluther must be horny. Hee hee JK

use lotsa lube

Some good advice here already (listen to @jca, @TheOnlyNeffie, @Simone_De_Beauvoir, @BhacSsylan, @jjmah, and @liminal). You have the right elements already, just go easy, take your time, play, and experiment, especially if one or both of you has never done much anal play. Way better to go slow and cautious than to risk pain or a traumatic experience.

I like it a lot, myself, both giving and receiving, and I’ve introduced some ‘virgins’ to it in the past. I wouldn’t jump right into anal sex, I’d start out by lubing my thumb or finger and touching around the area gently while going down on her, then working my way to rubbing my thumb over the opening. After a bit of this (if she’s enjoying it), if you press against it gently, it should open up for you. Tease and enter just a teeny bit, exit (but not all the way), have lots of patience, and work your way in and out a millimeter at a time. Pay attention to her reaction and play her like a well-tuned instrument. :)

You can get her off that way, or move right into the toys, it’s up to you guys. An important thing to note is that there are several sphincters in that tract that you have to get to relax before you can penetrate her fully, so this is why it’s utterly important for her to be relaxed and for you to take your time getting inside. You cannot just jam it in there (and if you have ever had anyone do that to you, you would understand why that is anything but funny—OW). I keep coming up with cheesy metaphors.. think of it as unlocking a series of vaults. The first one is outside, you get through that and you reach another just inside, and so on. You can hold still and wait, but I find that slowly moving back and forth inside her (but not pulling out completely) can help.

A great resource is Tristan Taormino, the ‘anal sex guru’. Her video The Expert Guide to Anal Sex is part porno, part educational series. Tristan has traveled and lectured around the US on the topic of safe, healthy, sexy anal sex. I think she’s kind of hot, as well. ;)

Oops wandered into this thread by mistake. Sorry. Off we go… shhh… don’t mind me… keep talking about – whatever it was…

Thank you all so much for the advice. We will certainly go very slowly on this. Lots of lubrication, gentle, slow, not trying to go all the way in one session; whatever pace is comfortable for her. My objective is her pleasure.

We’ve discussed this again and have decided that she will do to me whatever I do for her. That way I’ll have some idea of how it feels to her. I’m also returning the trust that she has in me not to harm her. Trust is the foundation of our relationship.

There’s lots of great advice here, especially from @jca and @MissAnthrope . They’ve pretty much said everything I was going to say, only better!

The only thing I have to add is some advice on choosing a lube and choosing toys. When I worked at the adult toy store, having anal sex for the first time was one of the #1 most common questions we got.

@TheOnlyNeffie is right about anesthetic lube being a no-go. A couple people mentioned KY, which isn’t really ideal for anal. KY has a light, watery texture and doesn’t really stay slippery long enough. It’s mostly water and glycerin, so after a little while the water goes away and you’re just left with sticky glycerin residue. The other thing is that with very tight penetration (like anal), a lube with a thicker texture can make things a little more comfortable. There are other water-based lubes that are more viscous and stay wet longer. ID Glide and Astroglide gel have a nice, thick texture but are still slippery, and they’re available in the drug store.

Anything oil-based, like vaseline, isn’t condom-safe. The chemicals in oil will dissolve latex. If you use oil on a latex toy (like a plug), it will start to dissolve that, too.

You can also get a silicone-based lube, like Wet Platinum or ID Millennium. They’re very, very slippery and stay wet pretty much forever because they’re not water-soluble, but they are safe with condoms. Silicone is hypoallergenic and very safe, but it’s better for anal than for vaginal sex. That’s because you have to wait for the body to… clear it out, or you have to wash it off. It doesn’t go away on its own. It basically feels a lot like oil, but is much safer.

Choosing a toy: If you get a plug, it’s meant to be left in so the muscles can gradually relax. One of the most popular ones we sold was a lot like this. It was very slim, but larger than a finger. You could also try a small wand-shaped vibrator or a vibrating bullet. A bullet is a very small vibrator with a remote control attached. It’s mostly used for clit stimulation, but you can also use it around the outside of the anus. If you insert it, it’s best to put it in a condom so you can remove it. Actually, it’s best to use a condom over any toy.

Just saw your second post… that’s really awesome and open minded of you. Good luck!

@Haleth We’re thinking of getting a set of plugs in graduated sizes. I’ll be careful to make sure that any lube we use is compatible with the condom used over it. Will the egg-type vibrator we use for G spot stimulation work or should we get something a bit smaller? I’ve also seen some designs where the girth can be varied using a pneumatic pump. Are there advantages to this?

As you know…cleanliness is of the utmost importance here. Be sure to have some sanitizing wipes close at hand, so as not to contaminate the vaginal area. In the heat of passion, sometimes those things are easy to overlook.

I just think it is so cool that you want to do everything right. If only everyone were that way about a long list of things! :)

@MissA Very good point. We’re planning that everything associated with anal play will be covered by a condom or latex glove. I’ll be very careful about contamination of the vaginal area.

Lube, lube, lube!

Practise exploring with fingers firstly or a butt plug…she can do this on you too. Anal for me is best when i am already on my way to climax, i am completely relaxed and almost pushing him in without restraint

Oh and did i mention lube?

I told a “friend” about this question.

She said… Yes she… said…
Just tell him to slam it in her ass.

I’m not religious or anything…. never done anal sex… but um…. I think god only intended for it to go in only ONE hole…...

but hey, what ever floats your boat, have fun!

@shoebox

I’m not religious either, but God! must have a sense of humour then I guess, because I can’t count the times I’ve slipped in with all the excitement! ;-) Lol…..

hahahaha!

@shoebox – So, does that mean you don’t believe in oral sex, either?

What I can’t get over is that it’s this girl. Very disturbing.

I’m bowing out of this thread for good now. I have no interest in associating with people like that.

@jjmah: that was from 6 months ago. how do you know this is the same girl?

Did you read the last bit (at the end of the thread)? It is.

@jjmah : aah, yes, i read it and it definitely is creepy. i advise everyone to read the link that @jjmah posted, read all the responses and you will see the what she is referring to.

@MissAnthrope no…. only said I think god intended for it to go in one hole…. anal just sounds so difficult….. never said i was against any of it

It’s almost a feeling of,,,,“What happened here!” Thanks for the link from one to the other. I had JUST found the other but hadn’t been to the end yet. But, my suspicions were growing. Now, I’m left wondering, what changed with @stranger_in_a_strange_land for him to do such an about face, no pun intended.

What am I missing????

I’ve been attempting to reply for the last 4 hours and my attempts were blocked. I want to clarify things before leaving the site:

I freely admit that my fiance was the subject of the question from five months ago. Our present relationship did not begin until 3 months after that question. She had done nothing improper and was a victim of gossip, I overreacted to the situation.

During this interim she has become a legal adult. I helped get her out of a highly abusive situation and into counseling for the damage it had done her. What was initially a protective relationship turned into a romantic one at her initiative. We have helped each other greatly; my depression has lifted and her PTSD symptoms much improved. Several weeks ago I asked this wonderful lady to be my wife, she happily agreed.

There is a 35 year age difference between us. I’m well aware that many are critical of our relationship for that reason alone. There is absolutely nothing abusive in our relationship. Contrary to legal advice, I’m not even asking for a prenuptial financial agreement. Equal partners, no exceptions.Her therapist and mine agree that our relationship is healthy and mutually beneficial. We are attending prenuptial counseling to try and work out any problems in advance.

I understand @jjmah s concerns. I know that she suffered abuse as a young girl at the hands of an older man. I have repeatedly attempted to explain the issues of our relationship to her and that it is not in any way abusive. She has not only refused to discuss this with me, but has forbidden me to communicate with her in any way. I have respected her wishes. Now I find that she is spreading her misguided opinions in a public forum. I consider this most unfair. My fiance is enraged over this.

I posted this question at my fiances request; she wanting to explore something that I’m unfamiliar with, I not wanting to take any chance of causing her discomfort or trauma. Is this the action of an abuser?

Jacqueline and I are deeply committed to one another and will be marrying in November. We are totally indifferent toward any outsiders opinion of our relationship.

This is my last posting on Fluther.

I don’t regret anything that I said. Having been abused myself, I just found the whole thing creepy and uncomfortable. A barely legal girl (who had been raped before) jumping into the arms of a much older man. A man, who’s intention was to help the girl, but, then it turns out that they’re an item and now he’s asking a question about fucking her in the ass.

Helping her out is one thing, but, the relationship part and the bondage/anal sex part with a young woman who suffers from PTSD after having been raped?? And, by a much older man at that?

I never accused you of lying. Not sure who that was. I only stated how I felt about the situation and that I didn’t want you to contact me anymore.

Give her time to heal. Be a friend.

I can’t see a therapist saying that it’s a good thing. The whole thing is warped and creepy.

i don’t care what he says, this is creepy. one day the girl is going to regret this relationship.

@jca If, in fact, any of his story is true..

He pulled a stunt on answerbag. Not going into it here.

From what I am hearing now, man, I am glad that he is gone.

can someone pm me with some details?

Is’nt it wild how some questions turn into like these living things with a mind of their own. Wild.