Tips/Help with Anal??

Discussion in 'Introductions' started by jjsissy24, Apr 14, 2014.

  1. jjsissy24
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    jjsissy24 Member

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    I introduced the idea of crossdressing and anal play to my girlfriend(on me,my gf is not comfortable with the idea of recieving anal herself) a few months ago and we both really enjoy it.
    The first time my Gf ever fingered me she managed to milk me really well and she even caught it in her hands and made me lick it up! (it was so hot)

    So we moved on to buying a strapon and also a Vibrating Prostate massager (Duke Fun Factory). Even though i like the feeling of fullness in my ass with the strapon and the plug, I notice that everytime my penis goes limp whenever im being entered, and i never seem to get milked, or even come close to an orgasm!
    I really want to try getting an orgasm without any genital stimulation as I know it would make my gf really happy as well! The only time i did get milked was like i said,when she fingered me and managed to properly massage my prostate.

    So is there anything you guys can suggest? Any tips would be great!
     
  2. SubVerity
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    SubVerity Still the mansion's fairy godmother. ;)

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    Firstly, many guys lose their erection with anal. It's really quite common, so relax, nothings broken! :D

    The way to achieve erection and thus the possibility of orgasm, during anal penetration, is to focus on and exercise your pelvic muscles, as if you're trying to milk whatever's penetrating you from your own muscle contractions.

    Practice makes perfect with this, so happy practicing! :)
     
  3. jemima
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    jemima maid for my Mistress

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    i not allowed out my cage when Mistress use strapon but i does dribble a lot.
     
  4. guest 2942
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    guest 2942 Long term member

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    @jjsissy24 , I assume you are talking about a prostate orgasm? If you are this can be kinda difficult to achieve. I would recommend you check out the forum on Aneros.com. The site has all the information you would need to achieve a prostate orgasm.
     
  5. Pillowbiter
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    Pillowbiter Adore All Females, They so deserve it.

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    You do stay limp when getting pegged, You have to find the right spot, Mistress and myself been doing this many years, Only once had a orgasm with no touching. It was heaven, A lot of times she releases me, And yells squirt, you sissy bitch, as she fucks me. Squirt bitch, I rub myself, like a clitty, And soil my fingers
     
  6. dsinbraces
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    dsinbraces Dominant wife/KH of dickie

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    I have found that the more flexible the strap on used, the easier it is to make sissydickie cum. she tells me that the feeling more resembles getting the "real thing", which many times will result in orgasim depending on pace and duration of her being penetrated. Slower, ledd forceful srokes seems to work just fine!
    Mistress Suzan
     
  7. Reltsihw
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    Reltsihw Member

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    When I'm playing I feel this tremendous pressure build up. It was so strong last night that I shot a VERY large butt plug out of my ass.

    Upon doing that a liquid shot out of me. Was it urine? I'm not certain

    Both parts make me wonder. Am I cumming during that?
     
  8. Mistress B
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    Mistress B Mistress B

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    LOL, Do watch out for the light fittings. I once broke a lamp with a champagne cork.
     
  9. Mascara^Snake
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    Mascara^Snake Banned

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    You should try sitting on it Reltsihw
     
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  10. Harry Haversackers
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    Harry Haversackers Horny Old Goat

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    I think you ladies are well aware that we males tend to be a bit gassy. For many of us, a butt plug is dangerous ammunition...

    "Be careful where you point that thing, Eugene... It may be loaded!"
     
  11. Pillowbiter
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    Pillowbiter Adore All Females, They so deserve it.

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    Funny, I once had my very large butt plug in me, Dressed In all my prettys, My 6 inch heels on, Tripped and fell on the floor, When I hit the floor, my butt plug shoot out of me and made a very load popping noise, and flew across the bedroom, my wife/mistress pissed herself laughing at me. What a site, I was. ROCKET!
     
  12. Rachael_
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    Rachael_ Guest

    Some ladies! No knickers ;p
     
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  13. xcitedsisssy
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    xcitedsisssy cd/sissy michelle

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    Shooting butt plugs! A good belly laugh this morning.
     
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  14. MistressBitch
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    MistressBitch Long term member

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    this thread did make me laugh, just got this mental image now, of all you people, dressed up as sissy, firing various shaped and sized butt plugs out of your arses, you could start a competition, see who could fire one the furthest!!! lmao,

    Anyway, I think one common problem with trying to milk someone is that its tried too often, and stimulation is often too hard, ie the prostate is rubbed too harshly. Firstly, its less common for a guy to be milked without any penile stimulation, but also, usually the penis is flacid when this happens. When you try, try when you have not done anything for a week or three, give it a complete rest for a month, then try. Also when you 'stroke' the prostate, be very careful not to press too hard, you should use about as much pressure as if you were rubbing your own eye, you dont need to press it hard at all. Last time i managed it successfully, i had one hand up his bum (obviously) and the other, with the head of his flacid penis between my left index and middle finger, gently rubbing there. He was NOT hard, and I was surprised it worked, but the circumstances above is what achieved success in my case.

    Hope this helps

    MB
     
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  15. Harry Haversackers
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    Harry Haversackers Horny Old Goat

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    The visual you've given me here caused my device to shrink rather rapidly... We've never been successful with prostate milking. Perhaps I'll ask my sweet bride if she wants to give it another go using your advice to go gently, rather than aggressively. The last time we tried, she was very hopeful, but it just didn't work, even though it had been over six weeks from my last ruined orgasm.
     
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