Just The Tips: Relax That Butt Before You Dive In

Some of the cockiest tops in the world have no idea what they’re doing. These guys thrive on their aggression, thinking it makes up for their complete lack of skill. And you know what you wind up with? Some dude immediately stuffing two fingers up your hole, when it’s not even lubricated or relaxed.

There’s an art to getting your partner ready for penetration. Some guys would have no problem with a little dry and intrusive exploration, while others need more coaxing before you make a first move.  Each individual requires a different level of preparation, and the ultimate goal is to read his signals and respond to the motions of his body.

I know, I know! That sounds like some new-age, hippie bullshit philosophy. The point? You need to get him relaxed before you make any sort of plunge. Massage his upper thighs, lower back and cheeks. Run your tongue along these areas. If he’s into it? Slap those melons. After a slap or two, massage them some more.

Once you’ve successfully relaxed the outer muscles, you can move on to prepping his hole. Spread his cheeks and rub it with the backside of your thumb. Tap it firmly with your index and middle fingers. Hell, you can even massage it a little from the outside. Some form of lubricant might be helpful in this process…

While you don’t want to torture him by holding back, the point is to have him squirming towards you by the time you’re done. On certain occasions, guys will beg you to lube up your dick before you complete one or two of these steps. Like I said, each individual is different. You’ve just got to read them.

– Dewitt

Photo credit: College Dudes

To check out Jason Ryes showing off his hole, follow the JUMP:

38 thoughts on “Just The Tips: Relax That Butt Before You Dive In

  1. Unfortunately too many guys use porn as their guidebook for sex. You know, the scenes where the guys kiss for a minute and then seconds later the top plunges his dick into his partner’s ass. Porn is NOT reality, guys. First there’s editing. Then there’s the fact that the bottom has usually prepped himself beforehand with a dildo or butt plug. Personally, I enjoy the long foreplay before the main event.

  2. Jay is absolutely correct about the (mis)cues people get from porn. Topping isn’t about getting a hardon and shoving it in in one fell-swoop; any top worth his salt knows about prepping his partner. P.S. I cringe at any ‘top’ who doesn’t rim–NEXT!

  3. I’ve never just pushed in. Always prep first (cuz I’m kinda big) so it doesn’t hurt your partner. Rimming is great, so is fingering (although I know a lot of guys don’t like fingering because a finger isn’t as pliant as a penis). Then I like to ease in just the head and have him squeeze gently before I pound the bejesus outta him.

  4. Ugh, THANK YOU! Coming from a bottom who can take a lot, it still needs to be warmed up first. And tops, learn how to finger a hole correctly and, by all means, cut your nails!

  5. Few things kill the passion that gets built up during foreplay like a top who is painfully aggressive and just keeps pushing despite all the body (and verbal) language to indicate how unpleasant it can be. There are plenty of “total tops” that really could use a rushed, dry dick in the ass to see how terrible their impatient bullshit is.

  6. Too true.

    The first couple times I topped, I was a bit of an inexperienced dick at it.

    Thankfully, the first guy I bottomed for was 9 years older than me and knew what the hell he was doing. It made all the difference in the world.

  7. As a Top i have learned a few things from Bottoms body lanuage to clue me in as to when it’s time to be gentle, or rough. It all depends on the Bottom’s expirence, and desire to get fucked. Rimming is good for some, but for me the stomach bugs doesn’t make me want to dive in like i used to. I miss it though. Preperation from both Men makes the sex a blast in many ways. Fuck on!

  8. I completely agree about prep before penetration…many years ago, a dear friend that was a top told me that to be a exceptional top, one must first learn to be a good bottom, and learn to read the body language of the bottom.
    From my ecperience, truer words have never been spoken.

  9. Sure glad you brought this out to all those guys that fuck and run. How about some kissing and fondling and fingering before applying the lube. Once horny and loose slowly pop that mushroom head in and the rest follows so easily. Let it in for a minute while kissing and then pound away to your hearts content.

  10. I have been pretty much 100% Top since around 1993…but when I first came out and had my first man-to-man sex after college in the 80’s, I was mostly a bottom…many guys have commented on what a great Top I am…I think that has a lot to do with having experienced being a bottom before…yes, many Tops are clueless and just in a hurry to “shove it in”…since I absolutely love to rim a clean and sexy ass for hours, I find that those bottoms are more than relaxed and ready for me when it is time…

  11. THANK YOU!

    I swear there is no shortage of tops who somehow think that, because they have big dicks or are just super hot, that they know what they are doing.

    I have been at the receiving end of way too many scratchy dry fingers slamming into my hole or 30second rimjobs. And to be honest, after they screw it up, it makes it harder to relax and feel good cause your insides have already been scraped up a bit.

    It truly does take some bottoming experience to know what the fuck to do as a top. Because of my vers/bttm-ness, its made me the expert rimmer and fingerer that all TOPS should be.

    Seriously, someone should write a manual for these types. In my book, fingering should NEVER hurt if done right.

  12. I’ve stopped bottoming because of these guys, and there are some older guys who say they are experienced who have yet to figure out how the ass works. I’ve even prepped and fucked a guy so that he was pre cumming all over his stomach before I put his dick in, and then he asked to flip flop and just tried to push it in. I mean, c’mon! Did the last hour not teach you anything about fucking?

  13. Haha. It’s true.

    Though, I’ll admit. I’ve had my days where it’s like, ‘Oh fucker just pin me down and go to town…’

  14. I like plenty of lube to be used, but most usually don’t want anything going in before the dick. Don’t get me wrong, I want it slow while being introduced.

  15. I would bet that 99% of the “total tops” out there had a horrible bottoming experience once and never got over it.

  16. Btw, MiltonsMusic: they are on to you. They know you post under several different names and only make derogatory remarks, most of them racist. YOU are the pussy for not being able to post under only one name and having to hide behind many. Just shut up already.

  17. As a TOTAL TOP I pride myself on giving my partner ( the bottom ) as much pleasure as possible . The penetrating thrust should be deep but not overbearing by allowing a few seconds ( between thrust ) give your partner ass a chance 2 get used 2 the big dick that inside of him . Once his asshole start 2 adapt than proceed 2 give his ASS the fucking the DEEP DICKING of a life time . A TRUE TOP that knows how 2 use his equipment needs not 2 be overbearing BIG pain N the ass ….. BTW 2 all the HAPPY bottoms out there perhaps U should stop all the I can handle what ever U can dish out !!

  18. Great post Dewitt. Can’t say I’ve ever been with an ‘inexperienced’ top but if a guy just rammed his dick into me without any warning/lube I’d probably slug him.

  19. I’ve had my fair share of guys want to fuck me without proper prepping. A few time sI jst let them fuck me knowing that when they were done it would be over and they would leave. I’ve found with time that I have gotten better at picking more caring tops. I like having my ass used and played with so they fingering, toys, rimming and other ass foreplay are a turn on for both of us.
    This past weekend, I was at a party and met a guy. He put me in the sling and started rubbing my hole and balls. A little lube and a few fingers later I was maoning and grinding wanting his hard dick. Slowly fucked my with his cock head before thrusting inside of me. He did not use allot of lube and fucked me hard. I remember feeling like my ass was being pulled out of me and then my body started convulsing. He buried a load deep in my ass. When he pulled out I could feel the juices dripping from my overly used hole. He smiled and said he loved my hole and loved watching as I experienced an “anal orgasm”. WOW!!!

  20. i was pretty new at bottoming, and hadn’t learned to enjoy it at all…yet. when my overseas BF got in there and went a little too deep a little too fast a little too dry. i felt like someone had suddenly shoved a brick up my ass. before i even realized what was up, i had pushed him off me so hard and so fast that he landed half way across the bedroom. fortunately, i spoke enough of his language to be able to say, “what the FUCK! i’m not your wife–i don’t have a fucking PUSSY!” i became a somewhat more ‘aggressive bottom’ after that. hey, tops! learn what the fuck you’re doing…and you will be worshiped by a good bottom!

  21. I am a vers/top who knows how to prep a bottom. I like to rim, tease wirh the head of my cick, use toys if the bottom is into that. Take my time and go slow. Foreplay can be hot and make the sex better and last longer.

  22. First time poster here, so hope you can help. I’m in my mid 20s, total top, have never ever bottomed and to be honest, have neither a desire nor curiousity to try it, some people in my view can be a top/bottom by nature without needing to have tried the alternative I think, its my Baghdad logic, I don’t need to have visited to know I wouldn’t like it there 😛

    My question to everyone is this, I have been told i’m a good top, and while love being rough and dominant, I always ensure that I put the guy i’m with at ease, but…I don’t like rimming, I’m a hygiene freak and while I know the ass is well clean for the sex about the happen, mentally I can’t get turned on by the idea, unless I’m showering with the guy, at which point I can see for myself that its clean so go for it.

    Since rimming is one of the most important ways to prep a guy, and since I’m not a fan, are there any other ways I could help a bottom feel ready to take my dick? I love sex, but wanna constantly improve so that I get better and better, any help appreciated.

  23. Whats the deal with rimming? I know it feels good and watching it porn always turns me on, but for some reason I cant bring myself to do it. I avoid it almost completely unless a bottom begs me for it.

    This was really awkward with my last bf who loved rimming me without even asking first, and i felt bad because I couldnt get into the kissing nearly as much afterwards. And he could tell. Something about it just grosses me out on a fundamental level. I really wish it didnt because I like to make sure my bottom is having a good time.
    But I always feel that strange urge to back away in case it might not be “clean”. I’ve never had a bad experience with this (i.e. tasted poop) but its one of my biggest fears, for some reason. Any advice for an amateur ass-eater?

  24. Well done Dewitt! I’m sure all those “Top Only” guys will get puffy because they’re they shit when it comes to topping. The best tops are also bottoms. How on Earth can one have any idea how what you’re doing feels to someone else unless you’ve had it done to you? Answer: you can’t.
    Keep up the good work Dewitt (on all fronts)

  25. Thank you Irishguy and Jarvis – Was getting worried that I was the only one who has reservations about rimming either giving or taking. Theres plenty of lubes to help smooth entry but a lot of the time its just the feeling between the two of you and both feeling relaxed and wanting it to happen, the porn films have made it seem like topping should just happen automatically and its great to see the top guys posting here and saying how aware they are of their bottom guys feelings.

  26. just want to suck and get fucked by a man maybe swallow no porn two men in bed enjoying sex i,d like to lay on my stumic and take it in at first ?

  27. just want to suck and get fucked by a man maybe swallow no porn two men in bed enjoying sex i,d like to lay on my stumic and take it in at first ? im bottom

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