Just The Tips: Ease Him In

In my experience, men who identify as straight, bisexual or “total tops” aren’t always comfortable with having their asses played with. While this may be due to a negative experience in the past, many of them have simply never had any experience at all. Frankly, they might love anal play… except they just don’t know it yet.

Look, I’m not saying you should run around trying to turn heterosexual dudes into power bottoms, but there are certain ways of testing the waters. I have a little trick I like to break out while servicing self-proclaimed straight or bisexual men, and it’s proven to be successful time and time again.

It all comes down to four simple words–lick their motherfuckin’ taint. Don’t rush into it right away. Focus on his shaft for a while, then move down to his balls. As you’re flicking your tongue down there, move a little lower. Gently run your tongue around that area, or lap him up from the taint to the tip of his cock head. Hell, you can even do both!

If he’s digging this motion, gradually move your tongue closer to his hole. Some guys will immediately respond to this and hesitantly lift their legs in the air. Others might pull you back to your assigned position. But eight times out of ten? They’ll probably let you lick.

– Dewitt

Photo credit: Chaos Men

To check out Alexandro getting serviced by Teo, follow the JUMP:

24 thoughts on “Just The Tips: Ease Him In

  1. I typically don’t comment but I thought this time I’d share a quick story to illustrate Dewitt’s tip.

    I grew up with a guy who was black, tall, extremely fit and extremely handsome and probably the biggest ladies man this little town had ever seen. He was always an acquaintance of mine but a few years back when I became his boss at work by having him hired to help him get a job, we became friends and he found out I was gay. He had zero experience with gays in a positive way and it made him homophobic, but always told me I didn’t seem like I was any different than anyone else, so I just became another one of the guys to him. I jokingly told him one time that I always had a crush on him (I wasn’t REALLY joking and I think he knew I wasn’t) and we sort of shrugged it off.

    About a month ago, which would be about 3 years since I’d gotten him hired at that job which neither of us work at anymore, he sent me a message online asking if I’d come over (this was about 5am on a Sunday morning) and said that as long as I swore never to tell anyone we know, he wanted to try a blowjob from me, making it his first ever gay experience.

    I went over and we started at it and we spent about 2 hours non stop with me just doing my thing on him and he was loving every second of it. About an hour into it I did exactly what Dewitt says to do here and slowly worked down to his hole and he did exactly as Dewitt says happens with him and he lifted his legs and let me lick or do whatever I wanted and he was nervous, but loved it.

    My point is: It works. Try it. Worst that can happen is they’ll say no or just move you back upward. They’ve already convinced themselves to try a blowjob or whatever else, chances are they’ve decided that someday they will try to let themselves experience that part of it too, if for nothing else than to just prove to themselves that they don’t like it.

  2. uhm… I don’t know what you’re talking about, Dewitt, cuz from my experience bisexuals LOVE getting fucked [hell, they’re often face-down in a pillow before before you even get the chance to close the bedroom door! LOL] cuz that’s something they can’t get from their wives/girlfriends! What bisexuals DON’T like usually is kissing/cuddling, cuz that’s just TOO intimate [ie. queer]

    Having said that, the ol’ rimming trick works on ALL guys–esp. the gay ones & self-proclaimed ‘tops’! 😛 It’s all just a matter of delivery, and avoiding ego clashes…

  3. i am a total top…my hole is never fucked…never…but i will always let a hott boi eat of hole…he always likes that

  4. I’ve never quite known whether to label myself as a total top or a vers/top. Some have suggested I’m a closet bottom. I have been fucked a total of 3 times ranging from bad to disastrous, but that’s another story.

    Back to this post … I LOVE to have my hole played with … I love to have my crotch licked, down the taint and to the hole! Push that tongue in deep and hard – love it! Nothing better than a guy that really knows how to rim, nothing worse than a guy who doesn’t. And really enjoy a hard cock pushing, testing my hole stopping just short of full penetration. Dayum!

    Now that’s what I call foreplay – definitely ready for the guy to sit on my cock or to bend over then, cuddle, rest, recharge, repeat.

  5. I personally hate having my balls, taint, and hole licked or played with. I get absolutely no pleasure out of it, and I identify as a top since the few times I did bottom, I was uncomfortable and didn’t enjoy any of it. I’ve had guys try to pull Dewitt’s trick on me and I just never enjoyed it and usually that is the cue to switch to sex then instead of foreplay.

  6. as a top…there really isnt anything better then eating a guys hole, getting him all worked up and then sliding my cock into him.

    Great blog. HOT pics.

  7. im am seriously ROFL right now, because this just happened last night with me and a friend! I did exactly what Dewitt said and sure enough his legs went up in the air! i cant believe that this is the topic of discussion after last night! it was great and he said he would like to try it again!

  8. Oceanguy4u, the “taint” is area between your balls and your hole. It aint your ass or your balls, its your taint…
    As bottom boy, I love eating a hot Top’s hole, gets me excited to know any second he’s gonna slide his big ole dick in my hole 🙂

  9. In my personal experience & from what I’ve garnered from other guys over the years, there are 2 primary reasons that guys don’t like having their ass played with. The first has to do with the suggested or implied psychological emasculation of the guy. So many guys think that any penetration of their anus by anything makes them less of a man. They think that once a finger, a tongue or a dick goes in there, they’re just not as much of a man anymore. And trying to convince them otherwise is a great feat in & of itself.

    The other reason guys don’t seem to like having their ass played with is usually because they did try putting something up their holes when they were younger or they tried getting fucked & didn’t know what to do or how to do it properly. They didn’t know anything about cleaning their hole out, lubricating it, massaging it, playing with it or how to loosen it up enough to take a cock up inside it. It usually turned out to be a painful experience for them & they can’t get that memory out of their head.

    I suppose that a few guys might also have a phobia about the hygiene of anal sex, even with condoms & enemas & lube available. I’m not sure you could ever convince those guys to give it a try.

    I really have only rimmed one guy myself, although I’ve had a few guys rim me. In my case, I was the bottom in a 1 year relationship in which my lover Joseph, who always topped me, with a few exceptions. On the first occasion, returning from a club a bit tipsy, my inhibitions were rather low & I let my tongue slip a bit farther below his balls than usual & found myself tonguing his hole, until he begged me to fuck him. Apparently, that was the magic key to open the door to my topping him, which I did. He always reasserted his top position during our next session. I was only able to use that trick on him 3 times total during our year together. I think I was probably the only guy who had ever topped him, to my knowledge. Of course, as much as he whored around before I met him, he might have been a retired pro at taking dick up the ass. The only way I can see Joseph bottoming now is if he needs something from one of his new lovers or friends in Dallas. If he’s getting something tangible out of it, he’ll probably throw his legs up over his shoulders again. Ha!

  10. I’m NOT being judgmental in any way, shape or form but I do NOT agree with the subtext of today’s topic

    My boyfriend and I have a loving relationship for slightly more then 5 years now. He’s tried bottoming twice and never liked it, somehow it’s too painful for him and he is therefore reluctant to try it again. I understand and sympathize for I don’t like toys, which I experience as being painfully uncomfortable.

    We have three rules in our relationship that we don’t stray from:
    1. We never go to bed angry at each other
    2. We are always honest with each other and don’t play games
    3. Monogamy isn’t just expected but also essential to our relationship

    Given our second rule I would NEVER play a trick on him to get him to bottom for me.
    We talked about it and he is willing to try it again at some future time to see if he’d be able to derive some pleasure from the act. But he’s not ready yet and I will NOT tempt or pressure him. I think it’s best that it happens when he is ready and comfortable.

    Why all the subterfuge? Talk about it and be adult enough to accept the word NO!

  11. Arion5, please don’t use blanket statements about us bisexuals. It’s just as bad as when straight people speak stereotypically about gay people. I (being bi) love kissing& cuddling (with a man AND a woman) BECAUSE it’s intimate.

    I also love getting rimmed, taking the occasional (small) dick up my bum (4 times, mostly felt okay), rimming, kissing, cuddling, massage.

  12. I’d have to agree with dak1975, too many people make assumptions about us bi guys. I happen to prefer being intimate with men, women are more an occasional indulgence. And sex without kissing/cuddling seems hollow to me, it’s part of the package.

    Only taken a dick once, it was quite big and I didn’t find it comfortable myself but I would never say never. Everyone has their own take on being bi.

  13. Oh boy, I could write pages on this because of my work (Click my name…see my site). I work with guys who have had negative assplay experiences in the past but want to learn to get the pleasure that they see bottoms getting. Typically their bad experiences have come down to poor technique from the top. I think guys see porn and think “oh, I should just be able to pull my pants down and a dick should just go right in just like in the movies”. What those movies don’t show is the bottom before the camera starts using toys or fingers to get his ass opened up to accomodate what’s coming. Assplay should be pleasurable for all men (gay,bi,str8) if it’s not, you’re doing it wrong. In the beginning it is all about technique both for the top and the bottom. Unfortunately all too often guys try it once or twice, it hurts and assume that they just aren’t built to be a bottom and then become “total tops” out of fear. Perhaps if their top had used Dewitts very effective technique (and it is a good one) things might have gone differently. Enjoy your assholes guys or find someone to help you learn to. With all those nerve endings on the asshole, it should be all pleasure all the time.

  14. @HngBlkBtm – talking about his dark dick – that’s funny coming from a black guy. I hadn’t thought about it but really liked his dick and you hit on it – it’s dark. Love men of color … and love dark dick! 🙂 Just thought I’d share – lol

  15. Speaking as a TOTAL TOP I have no problem being rimmed N fact I love it 🙂 🙂 but that’s as far as it go . I have been licked ,tickled & tongued a many of times hell I even like when a guy is laying on top of me ( love the whole dick 2 dick contact )while I finger his asshole letting him know exactly who’s end is getting plowed and by the time I finish plowing him he went right back 2 licking my taint & ate my ass and I LOVED IT 🙂 🙂 🙂 !!!

  16. ok i had four occasions of being a bottom the first time was horrible it hurt but it didnt last long i just was in a hurry to get out of there. My second time was amazing i told him about my previous experience so he was gentle and made me feel like a rockstar it felt so good the third time was fun it was amazing but it wasnt horrible either the last time which has been over a year now he rammed it in and kept going at it. I got rhoids that have never gone away since they come and go so im terrified of getting a nasty rhoid thatll last a month so im not completly open beacause the pain afterwards will not be worth it. Id like to bottom but the guy better listen to me. otherwise he wont hear the last of it.

  17. i think i have an alternate way of “testing the waters”..
    ..that is, suggesting to your prospective partner to take a shower together.

    if all goes well, you can have the opportunity to go exploring the guy’s (hopefully cleaned) back•side, at that time..
    ..i would try gauging his “openness” by using my fingers, first, while either kissing or blowing the bloake.

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