Friday, April 6, 2012

A reluctant bottom

Right now, I'd describe myself as a highly-motivated but reluctant bottom.   I'm determined to bottom successfully and experience pleasure from it.  We've done it now several times and I haven't completely gotten into it.

I blogged about my first "sort of" bottoming experience here and another more successful experience here.    Recently, my guy didn't want to continue because he worried that he was hurting me.  I tried to assure him that I wasn't in pain.  He wasn't convinced when I described myself as experiencing "less discomfort" rather than actual pain.  After each bottoming experience it would take me several days to recover 'down there.'

So far, I have not experienced anything remotely resembling pleasure while being a bottom. However, I very much like the idea of having my guy in me and the pleasure it gives him.

A few points:
  • I need to achieve a higher state of relaxation and warm-up before bottoming.  Right now, I'm rather dreading it.   
  • Stress is a big factor here, I think.   Now that I am soon to get sole ownership of my new home, I am much less stressed-out, but has only happened very recently.  
  • One issue is that we're both inexperienced to different degrees.  It would be helpful to be with a really experienced top, but I really have no desire to surrender my bottom to some stranger. 
  • I think a important factor is the position used.   Which is best for a tight, inexperienced virgin?  Doggie Style?   Missionary Position? Bent over a couch?  I was told this last one open you up the best, but I haven't put it to the test.
Help!  Bottoming advice needed!!


  1. One thing I find helpful is after entry, no action at all. Just get used to the feeling. Then have the piston action. Not sure how to describe this, but I also like to squeeze him for awhile until I seem totally ready. Hope this helps.

  2. Dude, are you sure you are doing the right thing?

    Reminds me of my friends that are now addicted to smoking. None of them liked it when they tried it, and now they wished they would have just quit while they were ahead.

    Yah, I know it's not the same, but maybe you just aren't cut out to be a bottom.

  3. I'm glad to hear that I'm not the only top who would like to bottom, but just can't seem to get the feel of it. I know I'll try again at some point in the future, but from what I've experienced, I would say the right cock in your ass in a relaxed environment with the time to take it slow, and the top needs to listen to you and follow your directions.

    I think the next time I try, I'm going to take a different approach, where I start out clean as a whistle and let my buddy rim me for a while, then get him to get a single finger in, find my prostate and let him work that til I feel something.

    The bottoms that I've talked with in person all say that they started putting things into their ass from a young age, so it's not something that most get off on the first time. I've also gotten a lot of encouragement to just enjoy being a top. The say there are many more bottoms than tops, though personally I know more tops, than bottoms.

  4. I feel your pain...for the first 11 years of our 12 year marriage I didn't enjoy anal sex. Of course I'm a girl so I always had another option. However finally I wanted to enjoy it as all my friends, gay & straight, were. So I asked my friend Rafa what I was doing wrong. This is what he told me:

    1) You need to relax. If you think "this is gonna hurt" then this is gonna hurt. Your partner needs to take extra measures to arouse and relax you. The more aroused and relaxed you are the better the experience.

    2) Lube! Lube! Lube! I can't stress how important lube is. Especially for someone not accustomed to anal sex. My first choice is Astroglide, then Anal-Eze (sp?), if you're out of lube Olive oil works great as does baby oil. Although baby oil isn't as smooth as olive oil or synthetic lubes.

    3) No matter the size of your partner unless you have a well trained sphincter you are going to need to stretch it out and prep it for each new encounter. While your partner is relaxing you with full body & mind foreplay your partner, or yourself, needs to be stretching your ass. Maybe have him rim you and slowly start with one finger while you stroke yourself. Slow and easy! Slowly start to use more fingers. If you're not used to anal you really need to take the time to stretch out and relax your ass before sex. Some people still need to do it even though they have anal sex all the the time.

    4) My main issue was when he put it in it hurt so much. I was told to Push like I was taking a dump when he's pushing in. It really does relax the sphincter muscles and make the entry feel oh so good. The first few times it will still seem a little too tight but trust me it gets better with practice. Sometimes during if it starts to hurt I push out and it helps to relax me again. Usually though once you start to enjoy it it will all feel good.

    5) Position matters. Some positions may be painful for one person and heaven for another. If one position isn't working find another one. For the longest time we had to be in the missionary position with him sitting up on his knees after he was in all the way, thus leaving all four hands free to help me stay relaxed. I'm still not able to do all the positions he thinks up but I'm willing to try them a few times varying things until it feels good or nixing the position all together.

    I think if you enjoy the fact that your man is inside of you and enjoy giving him pleasure that with time and practice you will enjoy it as much as he does. Also he needs to try and be relaxed and if you guys just work together experimenting you'll eventually come to a place of full enjoyment.

    Good Luck Honey, and ENJOY!!


  5. OK, when your partner puts on some lube, put on some more and then when you think there is enough, put on some more. Some analingus helps as well. For me the best position is to straddle my partner. He is lying on his back and I straddle him. Sit up straight and you be the one to control the rate of entry. I found knowing that I control it helps me to relax. No thrusting at this point. You rock gently when he is inside you. After a while, the muscles relax and you can switch to another position.

    I have found that if my partner sits up while I straddle him and he licks my left nipple (yes, for me it is the left one) I can come just by "riding" him while my penis rubs against his stomach.

    Best of luck to you.

  6. Hey everyone, thank you for sharing your comments, concern and excellent advice!

    CoreyJo; that has to be the best bottoming advice ever!! You could teach a class on Bottoming 101! Thank you, sweetie!

    1. You're most welcome love! I did forget control, like Bill said.. If you control the movements or actions by movement or words you will be more comfortable.. After 11 years of doing it wrong I'm just glad to be doing it right finally! I have faith it won't take so long for you. You were smart in asking where as I was too shy for so long. I guess I'm not shy anymore! LOL

      Happy Easter Buddy Bear, to you & your family :)


  7. If it doesn't feel good and you're not gaining any pleasure from the action - stop doing it. I don't think that you're cut out to be a bottom.

  8. As a guy who doesn't bottom very often, because I don't get the chance. What has made things go well for me lately is prep work. I always clean out well, and then I use a small dildo in the shower, and then a larger one. I put it in many times with lots of lube... so that when I get to the real thing, it is stretched and relaxed a little bit. I also know I will be clean for my top. It still is uncomfortable for the first 30 seconds, until he gets all the way in.

    Relax, and be in control at first. I almost always start on top, and if I can last, I will get in another position so he can then be in control. Have fun...

  9. Good afternoon. After reading the comments and suggestions you've already received I guess I'm writing to just reiterate a few thoughts. The first time I bottomed we used olive oil for lube. I think it worked only because I was very relaxed (on the deck of a mountain cabin after a while in a hot tub and a couple of glasses of wine). I say that because when we were home and tried again...the olive oil didn't cut it (though for c2c...LOVE the olive oil...but I digress). Eventually I discovered Rear Entry Desensitizing Anal Lube (Amazon). Wow. Made all the difference in the world. It really doesn't work as a lube so much as the desensitizing helps with the comfort and thus made me more relaxed. We use additional lube (Wet Premium works well...also on Amazon). I was worried about two things with the Rear Entry: that it might mask "important" pain that shouldn't be ignored and that it might dull other sensations...both mine and his. In our case, however, it is just a penis that is being inserted. A very nice penis but it's not like a baseball bat or a fist so I'm not so worried anymore about damaging my insides. That was just my inexperience talking. And the sensation for both of us is nothing short of amazing.

    My partner and I are both formally married and were late to come out. After over two years as a couple we are still enjoying the whole "finally being able to play" aspect of our sex life. Trust is a huge plus that you and your guy seem to have developed. That will help you so much. Personally there is no way I could let anyone I didn't know and trust enter me. I'm just too tight-assed (pun intended). I'm willing to bet though, that you guys will find your stride with this. And when you do...OMG.

    Good luck and thanks for your blog. I'm a new follower and am very much enjoying your site.

  10. As we talked about many time, I am an anal bottom virgin. I feel like you and I are alike in that we both want to try it not so much because we have a deep desire to be bottoms, but because everyone else loves doing it and we don't want to be missing out on something good. Well, at least that's why I'd like to try it.

    Another reason I want to try it is because I think if I was on the receiving end a few times, it would make me a better top. Does that make sense? Knowledge of what it's like to be the bottom will result in improved topping skills and techniques.

    As for pain, I had a real fear about that too. Greg has a bunch of dildos and one is quite large. One day I decided to test it and surprisingly it went right up there with little effort and no pain. NONE. Knowing that I can shove a massive dildo the size of an arm up my pretty pucker with no pain makes me think I can handle any cock that comes my way. Someday I may get to test this theory, but until then I have no fear of suffering pain while bottoming. If you have a big dildo you should do the same and (hopefully) break your fear of pain too.

  11. He lies on the bed, you sit on top of him, and practice
    I still think poppers help. Give them a try.

  12. How do you "prep" ?

  13. "Prep" just refers to cleaning yourself up before having anal sex. It should be sufficient to have a bowel movement followed by a thorough shower or soak in the tub. For extra cleaning, some guys will douche or squirt water into their asshole. This is generally regarded as unnecessary and may interfere with the normal bacteria colonies which naturally live in your lower bowels

    Please read Doctoring your Derriere for more information.

  14. Buddy bear: Thank you……

  15. Firstly, lots of foreplay and rimming help to relax you. Before you get down to enjoying yourself, prepare your ass...I use a thing called a "lube launcher". It's basically a turkey baster that lets you lube the chute deep inside. Often guys just lube the entrance and that doesn't work. Liquid Silk is the best lube I've found. You can also buy some lube in the form of a suppository. You push it up and over time it 'melts' so that when you're ready to play, you're already lubed.

    For positions, try on your side with him behind or sit on him is another good choice. Try to relax as much as you can - poppers can help but they're not for everyone.

    Tip of the day...masturbate as your partner tries to push in. Seriously, it works. I guess because you're not focussing on his cock pushing in.

    As a last resort...Private lessons available! ;0)

  16. Mike in AshevilleApril 16, 2012 at 3:32 PM

    Just came across your blog -- love your eclectic collections of pictures. Way too many guys have such a narrow view of what is hot, but like your pre-Christmas Indian dinner, I like my men extra spicy and a wild variety.

    I am 52 now and the first time I had anal sex, I was 14. Alas my family moved then, so it was 4 years of horny waiting until I was off to college and a renewed LOVE of being on bottom (my first day of classes, a jogging junior passed me and caught me cruising him as he was cruising me. 30 minutes later his hard cock was pumping a load of cum into me -- my first tea room fun!)

    So, how to keep it fun, again and again and again -- don't make it all difficult and ruin the fun.

    1) Buy yourself a nice medium sized dildo and butt plug -- 6-7 inches by 1.5-2 inches wide. Also purchase the next size up of both the dildo and butt plug, for round two. Pick colors that puts a smile on your face.

    2) Buy a tube a lube. Wink at the sales guy and he will tell you all you need to know about use with rubbers (water based), flavor, easy cleanup, etc.

    3) Put on some anal porn where you transpose yourself for the bottom; smoke half a joint or a good scotch or vodka. Whatever works for you that lets you relax and feel good but not too high/drunk. Mellow.

    4) Watch the porn, play with the dildo/lube and pretend its you in the video. You will probably experience a little trouble taking the dildo at first. The trick is, once you have spread some lube around and in your hole, and around the dildo, push out as though you are having a bowel movement. While still pushing out, place the head of the dildo at your hole. When you stop pushing out, your hole will naturally close -- gently push the dildo in and the natural closing of your sphincter will "pull" the dildo into you. You should not need to push the dildo too hard as the natural closing should accommodate the dildo.

    5) Play and enjoy. Move the dildo in-and-out left-and-right, high-and-low -- basically, maneuver the dildo around the way you would fuck. Also, learn to find your prostate because that is where all the internal physical pleasure is. By learning about your own insides, you will be able to guide a future cock to your pleasure spots. And the prostate is so much more than just a "G" spot.

    6) When you're done, clean up. Then slip in the butt plug and keep in until you can't (remember, you may need to push out and allow your sphincter to close and pull in the plug). Repeat over a few days, and just enjoy yourself.

    7) Get ready to replace the dildo with a guy. While playing with the dildo, practice to mentally relax your sphincter. When you are able to relax, add a finger or two with the dildo, and practice more stretching. (Stretching is easier when you are younger, at our age, this will take a few days, but it will make things so much more fun.)

    8) Go find a fun man to fuck you! Hit up a bar or go on-line. Be honest about who you are and what you want -- but make sure you say you just want to have some FUN.

    END PART 1

  17. Mike in AshevilleApril 16, 2012 at 3:33 PM

    PART 2

    ABOUT SAFE-SEX -- don't risk not being safe. We men LIE LIE LIE to get sex, and assume you will be told whatever that gets what he wants. I have been HIV+ my entire adult life, my doctor estimated I was infected in 1980 (first test only avail in 1986; in 1987 T-cell test indicated the virus had been in my system for years for my T-cell to already be down to 600). Since you just came out, I will assume you are negative; stay negative and maybe, with lots of luck, you will one day find someone with whom you have a relationship, and if both neg, only play safe with one-nighters, maybe you can one-on-one without condoms. Please be smart.

    ABOUT ON BOTTOM: Not literally, but I am the guy getting fucked in the third pic: eyes rolled back as the body experiences amazing pleasure. Mentally, its all pleasure too for me -- the idea of a guy "taking me" "breeding me" just makes me wants to let guy after guy enjoy orgasming in me over and over again and again. I am not saying you must think that too, but I do think being on bottom needs both the physical and mental pleasures.

    Enjoy yourself!

    Cheers and hope this helps, Mike.

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