Busting cherries 101

Hi Devon,

How are you? I am Vince, and I just have a question (or should I say, “I need you advice?”). My boyfriend and I have been together for three years now. But the thing is, we haven’t had anal sex! Ever! Our physical intimacy is limited to oral. We finally decided to give fucking a try, but our problem is that we never had anything in our butts! As seen from gay porn, the models seem to do it (the penetration) quite easily. We are afraid that we might hurt our anatomy down there. Do you have any suggestions how we can prepare for our first session? We really want to make it memorable and enjoyable for both of us.

Hope to hear from you soon.

Thank you very much.



Hi Vince,

For your first anal session to go well, you should first look at the process for preparing to be the receptive partner. I wrote an entry about this that you can read by clicking here. That will take care of the internal hygiene, but here are what I consider to be the three important ingredients once you’ve prepped: 1) patience/sensitivity, 2) lube, 3) condoms.

I don’t want to scare you, and I hope you will see the humor in this, but I once saw a bumper sticker that said, “It only hurts the first 19 times.” Anal sex is INTENSE. I don’t suggest you both trying to be penetrated the same day. If you both want to experiment with being fucked, I suggest doing it on separate days. I say this, because whoever is getting penetrated is going to need a lot of time. You will need your boyfriend to go extraordinarily slow. Seriously: Every centimeter will feel like a foot at first. Even with relaxation, love, curiosity, and lust goading you on, you will need several minutes just to get him inside you (and then you’ll probably want him to be completely still for a while as you relax more deeply). To ease this process, he should first very thoroughly eat your ass for an extended amount of time, then gently and gradually finger fuck you with one finger and then two (keep the fingernails clipped short and with smooth edges, so the nails don’t tear your delicates!). Once you have relaxed a bit you can graduate up to getting the tip of his cock in; however, his prick is going to feel 10 times fatter than his fingers, so go slow!

Second, you can never have enough lube when you’re beginning. Well, yes, you can, but it won’t seem like it at first. As you get more experienced you will do more with less; however, at first you will want to keep your boyfriend freshly slicked up (and given how slowly he’ll be pushing into you, it’s okay to expect him to freshen the lube a little with each little nudge deeper inside you). It will be intense, but if you can you need to let him move inside you a little to maintain his erection. If he sits too still for too long with your bear trap clamping down on him in a death grip, he will probably deflate and all this will be for naught.

Lastly, you should use condoms. I know you’ve been with him for a while, but one of the most common ways of getting HIV is from “monogamous partners.” If you reject this emotionally or intellectually, or if your spirit is somehow reviled at the thought of not trusting your boyfriend, then consider this alternative, which will keep his dick naked and free to move about without restriction: Female condoms are pushed inside you by your partner’s penis, then stay in place as he moves in and out of you. It won’t look very cute with the opening of the condom hanging out of your booty, but it provides protection while not sheathing your boyfriend’s cock in a standard male condom (which may kill his erection if he’s never felt the type of squeezing condoms tend to apply at the base of the penis).

So, set aside at least a few hours of play time, get a brand new bottle of lube, keep the protection handy, and have a good time!


Author: Devon Hunter

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  1. You also need to be aware that different positions can be easier or harder, either physically or psychologically. A lot of people think that newcomers may want to start out sitting on their partner’s dick, as it gives the receptive partner a greater sense of control. On your back, legs up (with a pillow under the small of your back for support) can be easy physically, and you’ll be face to face, so you can communicate better.

    You may want to check out a book like “Bend Over: The Complete Guide to Anal Sex for Men.”

    And don’t forget — those porn actors who are shown easily hopping on someone’s dick have very likely had some off-camera preparation. Don’t feel bad if you can’t match their apparent ease.

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  2. Oh, yes… very, very salient points… Thanks for mentioning them!

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  3. I got over my fear of douching and it has been great.

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  4. Devon,

    From reading your posts you might think that being the receptive anal partner is terrible horrible thing that you have to endure. Depending on the guy, it might hurt a little bit at the beginning, and then be an amazing enjoyable ride.

    Some guys can’t handle it, and others handle it easily. You never know until you try. Granted, going slow and gentle to start off is best, but it might be that it’s not as big of a deal as you make it out to be.

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  5. I never said it was horrible, I said it hurts like a muthafucka until you get used to it. Is that not your experience? Even with all my experience it still hurts to varying degrees each time (anything from no discomfort all the way up too unbearable pressure), depending on all sorts of factors. It would be remiss of me to tell a butt virgin anything else. If he does it, finds he bears it with less discomfort than I implied, and is pleasantly surprised… Well… Great! But if I go your route and it’s as intense for him as I should have said originally… Well… He may never try it again. Hopefully he will prep properly, get the foreplay most people would need in this situation, and use LOTS of lube and time. My experience is that the first attempts are physically nothing to enjoy that much, but that they emotionally and psychologically unleash a desire to keep trying.

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  6. But Devon, and it is good to talk about this academically, I am versitile, but I remember about 5 times where it never even hurt. This is what I cannot understand. I know in 97 once guy relaxed me while I was in a sling (it was not S & M just the place we were) no issue. I remember another guy I just bent over he slide it in not one bit of pain at all pure pleasure. Another time no issue. But yet other times it is like no way hurts too much. Its odd because I agree with the psychological aspect, if one is ready for it and one is not scared yuk things are going to happen even after douching, then it does not seem to be an issue.

    It is just that being totally turned on and not scared seems to make a difference. I just remember this guy how I just bent over, he shoved it in hard with condom and not one bit of pain. Yet another guy it was slow and awful. Not sure why. The only thing I would say is for some reason lying on my side and me pushing up against it does not hurt even when he starts going fast. Odd. Yet doggie it’s like ouch. Missionary is my favourate but that sometimes hurts too.

    Maybe it is a combination of all things. All I know is your advice is wonderful, but I want to do this in the future, safely yes, but in time maybe I will figure out why one guy can bang it in with no issue while another I have to stop. Strange body LOL.

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  7. I agree with one of the previous posters. Jasun Mark talks about bottoming a lot on his web site GDH…One of the things he would suggest for first timers is getting an anal trainer and start with that first the graduate to anal penetration…If they are both first timers this might be something that they could do with each other as part of the preparation process. Jasun recommends the Colt anal trainers which have different sizes of small medium and large. So after they do all of the things you mentioned along with anal training hopefully the experience should be pleasureable and exciting for both of them.

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  8. Anal sex is wonderful. It can be uncomfortable but once everything relaxes it can be an enjoyable experience. No it is an enjoyable experience. Porn stars are prepped before anal sex. That entry you see on film is not the first entry they have had that day. Also try different lubes. Some can work better for specific people. It is an experience that is shared between two people and a great one for two boyfriends. I agree try getting some small dildos and that might be a good step up after fingers.

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  9. I think Devon has made some terrific points here for Vince. Before my first time I got a dildo, which helped get me used to relaxing my hole–at least a little. Then during my first fuck the guy simply went too fast (plus he had a big cock), and it hurt like hell. I remember specifically thinking, “I thought this was supposed to be fun?” before I finally just asked him to stop. After two more similarly painful experiences I decided this was not for me, and I didn’t try again for a number of years. Finally I decided I really wanted to figure it out, and so I found someone who knew how to approach it slowly and gently, and it turned out I COULD handle it! After some more good experiences I have grown to really enjoy it, and one guy said I was a “natural” at bottoming! A far cry from that original pain I was in the first time! If only my early experiences had been with guys who understood how to top properly! Go really slow.

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  10. Devon,

    I never said that you should just shove it in and everything should be fine! Of course you need some warm up and not rush that whole thing. I just think that if you said something to the effect of “warm up well, make sure the guy is patient and attentive and use lots of lube. You’ll have one of three reactions: love, hate, or somewhere in between. Don’t take the first time as the way it will always be. Have fun with it, and enjoy.”

    As for me, I think there are few things better than having a man’s dick up your ass, and I’m versatile!

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  11. A lot of people have focused on the ‘physical’ preparation but really, in my mind, a lot of it is also the mental preparation. The brain has to be ‘loosened’ up just as much as anything else. I’ve been “working” with a young kid who is convinced he’s a bottom but every time he’s tried it, the poor guy he’s with ends up either bruised or giving up. It doesn’t take a rocket scientist to know after talking with him for just a few minutes that he’s got huge issues with ‘opening up.’

    And yes, I agree – part of that mental preparation is knowing what you want and expect from the top and communicating it. Haha, my own very vocal demands, you’ll all be surprised to hear, got me labeled a pushy bottom or a power bottom (depending on the perspective of the top!). But you know what, anyone willing to give it up to a top should have no problem telling him, “You want a trip to paradise, you gotta pay the price of admission.”

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  12. Wow, Thanks for everything, guys! 😉

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