Threesme - Woman standing between two men

Recently I asked you about sharing my wife with another man. You may recall that she was very hesitant. You suggested that I ask if she might be OK doing ANYTHING with another man. I followed your advice and she agreed to be massaged by a male friend while I watched. She agreed, and it was amazing! aA I suspected, she couldn’t resist getting into it. He massaged her all over, and with her permission, worked his way up to giving her an erotic massage. He stroked her clit, ate her pussy, and even rimmed her ass. He asked her to use a G-Spot vibe, and she ended up coming. Being the giving person she is, she returned the favor and sucked his cock, massaged his balls, and stroked him until he came in her hands. But she would not fuck or swallow. I think she will fuck next time. We have been talking about it. We have also been talking about possibly a double penetration for next time, and want to know any advice you may have about doing this properly. It seems the rhythm might be an issue. Also, I really want to fuck her ass being that she is my wife, but should I allow the other to fuck her ass too and we can both take turns fucking her tight ass or should we take it slower? Thanks again and I look forward to your advice!


  • Michael Castleman says:

    I’m delighted that my suggestions helped you and your wife explore new erotic terrain.

    Regarding double penetration, there are two types: mouth and vagina, and vagina and anus. Both require kindness on the part of the inserters. Don’t push erections into her mouth. Hold still and let her decide how much to accept into her mouth and how she wants to suck. Don’t push erections deep into her vagina without asking: Is this OK? Always follower her directions and respect her limits.

    You say you want penis-anus intercourse. Be careful. If you or the other man are not extremely sensitive to her limits, she might recoil from anal and/or from future threesomes. I urge you to read the chapter in my recent book, Sizzling Sex for Life, on “Anal Play Without Pain.” Follow its suggestions and you just might be able to orchestrate a DP that involves anal. Take it very slowly. Neither man should ever push into her anus. Hold your erections still at her well-lubricated (with Crisco) external sphincter, and allow her to press her hips back and engulf your erections with her anus. Check in with her frequently. Ask: Is this OK? Make any and all adjustments she requests. Always respect her limits.

    I continue to wish you sizzling sex for life!

  • Thooper says:

    Thank you! We are definitely planning to DP her ass and pussy. She naturally is a great cock sucker and that should not be a problem. As for me wanting to fuck her ass while my friend fucks her pussy i would like to know, if i am being selfish wanting her ass to myself or should I
    let my friend enjoy her ass too? I feel like I am being selfish wanting to have her ass all to myself. Also, I want her to feel free to letting my friend fuck her ass if that is what she wants. Lastly, you recommend Crisco as a lubricant, should I apply it to my cock, her asshole or both?

  • Michael Castleman says:

    I suggest you ask your wife about her openness to anal play with your friend, and support whatever decision she makes.
    Regarding Crisco, some people into anal play lube both the receiving anus and whatever is about to be inserted: finger(s), toy, or erection. Others use Crisco on just one. I suggest you do whatever your wife prefers.
    I wish you sizzling sex for life.

  • Thooper says:

    I talked to my wife, and she wants both me and my friend to fuck her ass. She was surprisingly quick in making her decision and i am very excited to see her getting her ass fucked. I want her to do as she desires. She did say she would like for me to give her an enema before start fucking her ass. I have heard of many different solutions such as coffee, yogurt and soapy water. What do you suggest would be best? We also discussed cumming in her ass and both my friend and I want to fill her ass. Are there any issues with cumming in her ass?

  • Michael Castleman says:

    Now that your wife has agreed to be on the receiving end of anal intercourse. It’s crucial to make sure she’s comfortable throughout the experience. You say she wants an enema beforehand. Excellent idea. I suggest buying a commercial product (Fleet brand), and having her decide who administers it, she or you. After the bottle is empty, it can be refilled with warm water or warm soapy water. Two or three enemas should leave her anal canal as feces-free as possible.

    When you begin anal play, I suggest starting with Crisco-lubed external sphicter massage for a while (one or two songs if you have sex to music). Then gentle anal fingering. I suggest starting this with your wife on her hands and knees or elbows and knees. Place a well-lubed finger on her external sphincter and invite her to move her hips back so that she controls the speed and depth of finger insertion. Please be aware that there are TWO anal sphincters, the external one you see, and another ring of muscle an inch or so inside. The internal sphincter is a bit more resistant to insertions, so she and you should be aware that she may experience some discomfort when inserted items cross those muscles. Go slow! Be gentle!

    Once she’s comfortable with accepting anal fingering, then proceed to two well-lubricated fingers, then a well-lubed small butt plug or dildo, then a well-lubricated larger toy. Many people believe that large toys stretch the anal sphincters and the anal canal, making them more receptive to other insertions Yes, to some extent, they do. But it’s MUCH MORE IMPORTANT for your wife to feel comfortable than to feel super-stretched, unless she wants that.

    For penis-anus intercourse, again, her sphincters and all erections should be well-lubricated with Crisco (though she may be ok with Astroglide, KY jelly, or other commercial lubes). Anal intercourse is usually most comfortable for women when they are on hands or elbows and knees. That way they control the speed and depth of insertion. Place the head of your penis at her sphincter, hold still, and invite her to move back on you. Once you’re inside, don’t pump like you see in porn. ASK her how much pumping she’s comfortable with, how deep, how quickly. Most women prefer shallow and slow, but do whatever your wife says.

    You ask if it’s OK to come inside her anal canal. Yes, it is. Semen is 97% water, so coming inside her is pretty much like her using an enema. Note: even after several enemas, fecal traces remain. Pearly white semen may have a brownish tinge as it leaves her body.

    I’m glad your dream has come true. Now be very careful how you proceed. Ask your wife about everything on every occasion you play this way. Do exactly as she says and don’t push for more, so your wife enjoys the experience. You and your wife might discuss the chapter on anal play in my book Sizzling Sex for Life.

    And that’s what I wish you and your wife—sizzling sex for life.

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