Have You Ever: Fingered Yourself?

A few months ago, I was showing off in my favorite room on Manhunt chat. This younger guy from West Virginia sent over an IM request, and I accepted it out of common courtesy. Also, he had a beard. And you know how I feel about men with beards.

We got to talking, and it began with the standard “Your dick is amazing. I wish you were closer, so we could [insert scandalous activity of your choice]”. Then, seemingly out of nowhere, he busted out a huge confession—his boyfriend didn’t know he was chatting with other guys. I didn’t even realize he had a boyfriend.

He explained that they’ve been dating for five years, and he’s very much in love with him. The only issue? He’s an extremely horny bottom who hadn’t been fucked for three months. Three months. Apparently, his boyfriend is very well-hung, and it takes a lot of work to lodge that monstrous meat into his tight hole. Their sex life mostly consists of blowjobs, mutual masturbation and watching porn together.

As a concerned and equally horny citizen, I strived to come up with a solution for his hungry butt. What about a dildo or a vibrator? He doesn’t like the way they feel. Threeway? His boyfriend would get too jealous. And, finally, why doesn’t he just (literally) take matters into his own hands? He’s never fingered himself.

WHAT??? At this point, I’m urging him to grab a bottle of lube and start exploring his own love tunnel. It’s one thing to finger yourself and not like it, but it’s a whole other story to have not even tried it. While I have no idea if he eventually took my advice, it at least provided some inspiration for this post… Is there anyone else out there who likes to bottom but hasn’t ever played with his own hole?

– Dewitt

Photo credit: Jack Jagger

To watch Jack finger himself, play with a toy and eat his cum, follow the JUMP:

36 thoughts on “Have You Ever: Fingered Yourself?

  1. When you are a bottom you do what you have to do to satisfy yourself if your partner can’t or you don’t have a partner. Of course I have fingered myself, many times, and it feels great. Try three fingers to get that cock feeling.

  2. ummm, i’m a bottom.  no bf, no fb, just me.  i finger myself…and love it.  i have a dildo too…feels awesome.  don’t get me wrong, a dick is amazing, but a psuedo-dick works fine too 🙂

  3. See, I’m not even a bottom and I’ve fingered myself. Just enough to get some pressure on the prostate while I’m jerking off. Mmmm. Feels good. 

  4. This post makes me feel better.  I thought I was the only one who has been in a relationship for a while and hasn’t had sex (we’ve been together 3 years, no anal since Christmas–it was a gift for him…lol).  I have lately not been into anal for reasons I won’t go into (ok… he has a small penis that kinda hurts…I know that makes sense to someone) but we just always j/o and have oral.  I miss it though, but have never been keen on dildos… afraid someone will find them ha ha.  Anyhow, maybe I should give them a shot.

  5. maybe we need some tips on the best way to play with your hole. I have done it but it is kind of awkward. I only like it now and again ut when i do it i get the best and biggest loads! If you have tips please let me know! 

  6. OK what are the add for not finger your own hole,even those call straight do it,even the doctor do it for you yeah  L0L oink,wooof

  7. I am a tried and true West Virginian!  While I have now lived in DC for ten years, I go back once a month.  If you have never been for a visit, not only is the state beautiful and full of great outdoors activities, but there is an awesome bar in Morgantown called Vice Versa.  Let’s goooo Mountaineers!

  8. I understand the little penis problem you speak of……it just doesn’t get past the pain threshold. I do prefer a man of above average size!  Winks.  I know you understand.

  9. I finger myself from time to time.  Same as jerking off, sometimes its nice to be in control of your own pleasure.

    Just like bottoming in sex, I think the trick is to go slow, relax, and use lots of lube.  It’s not going to be hot if you just start shoving fingers up there.  I will often take a hot shower first, just to get everything clean and relaxed.  Then I usually watch a little porn and jerk a bit before I start on my ass.  As far as positions, the two I usually use are on my back reaching between my up-in-the-air legs (also lets you rub your balls and taint) or get on my knees and then squat back down (don’t know how to explain).  I reach behind me and alternate between long, deep strokes with my fingers and quick banging with my thumb.  Not the same as a real cock, but it can get pretty close!

    How bout it guys?  Any other tips for Colten (and the rest of us)? 🙂

  10. I know I am going against the majority here but I have never fingered myself  and I am not turned on by it but  I do LOVE 2 watch someone else finger himself as I pin his legs up and  behind his head getting a birds eye view of  all the finger action loosening up his tight hole in preparation for the deep dicking that is soon 2 follow ..

  11. well..
    ..if one is cleaning one’s “hoo hoo” at least semi-properly, then one will have to pass the threshold of one’s anus to access the rectum.

    whether one is a bottom, a top, or in between.

    so, to that effect, i’d been fingering my hole for several years by now.

    and those several years have shown me that i can take it or leave it..
    ..or so i thought.

    while i don’t have much desire for being penetrated (98% top), i had discovered that having the outside of my “no-fun(ny business) zone” lubed-up and stroked lightly while i’m orally-pleasuring another person certainly is not a bad thing.

    for that matter, it’s not a “bad thing” to like my ass being played with, if not a little: what would life be like, if people felt shame about liking any form of anal stimulation?

    for, like Yin-and-Yang, this certainly cannot be a world of only Tops, anyway:

    we would all die.

  12. well..
    ..if one is cleaning one’s “hoo hoo” at least semi-properly, then one will have to pass the threshold of one’s anus to access the rectum.

    whether one is a bottom, a top, or in between.

    so, to that effect, i’d been fingering my hole for several years by now.

    and those several years have shown me that i can take it or leave it..
    ..or so i thought.

    while i don’t have much desire for being penetrated (98% top), i had discovered that having the outside of my “no-fun(ny business) zone” lubed-up and stroked lightly while i’m orally-pleasuring another person certainly is not a bad thing.

    for that matter, it’s not a “bad thing” to like my ass being played with, if not a little: what would life be like, if people felt shame about liking any form of anal stimulation?

    for, like Yin-and-Yang, this certainly cannot be a world of only Tops, anyway:

    we would all die.

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