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Nov 25 2014

Reassurance For Ass Men

Reassurance for the Men

Gentlemen! Are you a little concerned that you enjoy ass play? Here's my message for you. It's all going to be okay, really. Just click the words above.

 

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  1. New To Ass Play

    Thank you so much for your caring and comforting! I found your site via the Sex Nerd Sandra podcast just as I decided to jump into the world of anal toys, and your words of reassurance were absolutely helpful to calm that awkward feeling in the stomach. You are an amazing and caring person, and for that, I am thankful!

    1. Ruby

      Awww…Thanks!!!
      You are exactly the kind of guy I was hoping this post would find. Enjoy your explorations!

  2. Christopher

    I am a guy who absolutely loves getting pegged. I love it in my ass and i am not ashamed to say it. My girlfriend pegs me with a 7 inch penis shaped dildo and it is very very amazing. I can’t get enough of it haha. I actually would like something bigger! For all you guys out there contemplating doing this …give it a shot and let go and just let it happen. It truly is incredible
    Thanks.

    1. Ruby

      Christopher – I’m going to read this on my blog – loved hearing from you!!

  3. hotminded

    I do have to say, I wish I would have found this years ago. I was that scared guy, but now I have outgrown that and absolute love ass play with my wife. She pegs me often but never enough 🙂 And at her command I wear the wireless vibrating plug in public for her to tease me. We are both interested in exploring a 3 some involving a man, bi top preferred. I would love to spoil her with the attention of 2 men, and she wants to see me play with a man. Years ago I experienced man play, but realized I wasn’t gay because I didn’t want a relationship with a man…but wow, I was confused. He made me cum several times while only fucking me. But I crave the love of a woman and wow, I landed an amazing one. This exploration took time but wow, its worth it. Our sex life is amazing. Would you have any advice on this new adventure we both would like to share together? I could type for hours, but I think my hands would die. There is so much more I wish I could share, but I will save that for later.

    1. Ruby

      Despite you finding this late – I’m glad to hear you are no longer that scared guy. Sounds like you have been on quite a journey…and you have arrived at the best part!
      My advice about your new adventure…sit down and talk all about it a lot, go over all the possibilities and try to envision how you will both feel about it when it happens. Then set your boundaries accordingly. Always have a rule that either partner can pull the plug on the whole thing for any reason at any time. That will lend reassurance that your feelings are being taken seriously and nothing will happen that you don’t want to happen because you can always call it off. That’s a very important rule, even if your wife ‘commands’ you to do certain things. Underneath the role playing you need to know everyone’s feelings are being respected. And if there is something that you want to save just for each other, like kissing or PIV or whatever, make sure that is fully understood with your third before things are underway. In fact, after talking about it until you feel like you are completely on the same page with your wife, talk to your third a bit, too. Meet with him and check the chemistry, talk about safe sex, boundaries and whatever rules you have. Then you’ll be ready to really enjoy that fantasy coming to life!

  4. James

    Hi Ruby. Have a little dilemma here, or a couple and hope you can give me some of your wonderful guidance.

    Quite a long time ago I purchased a harness and dildo to begin some pegging fun with my Lovely. Little does she know I use the dildo whenever I can, solo. So the other night I donned the harness and dildo so I could fuck her with it. As I had read/heard on previous posts here to do that as to broaden the acceptability for the woman to enter into pegging. So after a while of that I am told that her preference is not the toy but me penetrating her.

    Fast forward now, I asked her just to try the harness on so she can feel it and I can see her beauty wearing it. I was denied and we will now have a discussion on the toys we do have and who/how gets to use them if and when. Now, I will finally let her know that I absolutely love anal play- something that I have not ever told her at least to my recollection.

    So the advice I am seeking is, am I or did I go about it right to have her just wear it and also how to tell her I crave more frequent anal penetration with or without her but prefer her to be in control. (as she is in our life anyway)

    thanks Ruby,

    1. Ruby

      James –

      So the other night I donned the harness and dildo so I could fuck her with it. As I had read/heard on previous posts here to do that as to broaden the acceptability for the woman to enter into pegging.

      My urging men to be open to wearing a strap-on was not to broaden the acceptability of a strap-on for the woman, it was to provide your woman with a more prolonged or different experience than your cock can give her. In other words, say you fuck her and finally come but she wants more. Strap-on to the rescue. Say she likes something a different size, be that smaller larger, wider, thinner, whatever. Strap-on to the rescue, because you can put any toy you want in there.

      Usually the place to start talking about pegging is not the strap-on. Read this article – there is some good information for you. Best of luck to you!

  5. james

    Thanks for replying Ruby. Sorry for my misinterpretation of the strap on use on her, great idea for prolonging her pleasure as I have an issue of poor performance. But I digress. After our discussion with laying all the toys out she had made the following comment/s.
    > I do not like the toxic smell and feel of the toys (plugs, anal balls and lovely dildo)
    > I will never fuck you in the ass with a dildo, never as I am unable to dominate you like that. And if that is an itch you need to scratch I do not know if I can do this. Just do not let me catch you with a hooker in the house getting your ass fucked! It will not go well.

    She did not however make any negative response of when I told her that I enjoy using the toys )did not even bring out the bum drops and big nite stick). But did mention that I would like the glass dildo she loves.

    So there are a couple things that are effecting her. So I guess I will continue to pleasure myself solo with the dildo/s and find a pro to do me when the time presents itself. For I will need that itch scratched some day.

    Thanks Ruby, have a glorious day!

    1. Ruby

      I read your comments and story on my latest podcast #100. Hope everything works out for you!

  6. Saralala

    I am not a gay,but I like the girl pegging me, I am a Chinese.

    1. Ruby

      Welcome to Pegging Paradise!! You have friends here… 🙂

  7. anonymous

    Ruby…
    Thanks so much for your work here, long been a fan of ass play/pegging but my ex made me feel unaccepted by it. I’m with a new woman now who is incredible in bed and while she’s unsure I feel I can talk to her about anything. I’m really hopeful she can share this with me as we move forward, your site gives me support and ideas in doing this.
    I sense a real “shift” in the pleasures of pegging where it isn’t always depicted as a humiliation/submissive/pain thing, although I certainly don’t judge anyone who enjoys that as well. I do like mild submissive play but without the over the top pain aspect but mostly I just have a sensitive ass : ) Thanks again for your great site and ideas, so glad I found you!

    1. Ruby

      Thanks for your kind words. I’m glad to hear you didn’t take your ex’s shaming to heart – because the shame really belongs on her for being so judgmental about your sexual desires.
      There is indeed a shift beginning to happen with acceptance around pegging, in all its manifestations. Becoming a tad more mainstream.
      Glad to hear you are hopeful of including pegging in your new relationship! Best of luck to you and let me know how it goes.

      1. anonymous

        I want to do a follow up to let you know that indeed we have had success. It’s a bit of a long, complicated and interesting story that I won’t go into detail (perhaps sometime if Ruby thinks it’s a good idea) but short version is we had talked about pegging, she had said she was open to trying it and while I was out of town she found my “stash” of sex toys. It freaked her out due to the volume and made for a difficult time but we worked it out!

        We followed your advice with purchase of the Fuze Tango double ended dildo and Spare Parts Joque harness. I was on my back for our first experience which she really dug and frankly is now all aboard the pegging train, so to speak! We added the we vibe tango on our second go round and holy shit, she came very, very fast. She was on her back and I mounted her, our only problem was going slow enough for me due to her level of excitement. She stroked my cock while fucking my ass and I came (to her delight) all over her boobs and stomach. It was epic.

        I want to add that I’m 61, she’s 51 and fitness is very important to both of us. I’m only mentioning this as encouragement for others who are frustrated to realize it’s all about communication (like everything else in a relationship) and exploration. If we can get to the place where men and women aren’t shamed over their healthy sexual desires (and I believe it’s happening, although we’ve got a long way to go) then life will be fuller for all of us!

        Cheers

        1. Ruby

          Yes! Great news! Gonna play the music for you on podcast #108! Congratulations!

  8. ShameBGone

    I’ve known since I was a boy that I enjoyed anal stimulation, but I inherently felt it was taboo, dare I say, homosexual, for a male to enjoy such stimulation by the time I finished puberty.

    A few years later in college, and I got involved with the techno house music scene and was exposed to substances that increased sensitivity, and ever so effectively, tossed most inhibitions out the window and in this state, not long after the first time I’d been exposed to these substances, I left the party early and took myself to the local adult store and promptly and irrationally spent 300 on a variety of adult toys and erotica. That night, which went on until 10 AM the next day, was extremely enjoyable, but upon coming down and sleeping, I awoke with a DEEP SOUL CRUSHING shame that I’d somehow crossed out of the straight world, and into the in between or possibly homosexual and in response, I threw away all the toys so no one would find them.

    I had an exceptionally healthy sex life with many wonderful women, but it was pretty tame in the grand scheme of things. I essentially buried this desire and didn’t touch myself that way again until the next time I was exposed to said substances, where I again, went to the adult store and dropped a bunch of money I didn’t have, and spent a blissful night of self-play, only to be greeted by the familiar shame and subsequent disposal of the day old toys. After 3-4 of these sessions, I began to think I was deviant, and crawled further into my head, as I was only willing to enjoy this while under the influence.

    Anyway, this went on for 20 years at least of periodic partying and then my disappearing for my alone time. In that time, I married my girlfriend of 5 years and our sex life was pretty much average, but she, never had any clue that I enjoyed this, and I KNOW how she would have responded had I worked up the courage to ask her, so I just didn’t. During our relationship, these “private sessions” became extremely rare, and I reached a point where I had sworn off substances like those I’d done for so long, and then she met someone she liked better and bolted.

    It didn’t take long, more as a respite from the emotional pain than anything else, for me to find myself under the influence and heading to the toy store at 1 AM. Just for the readers information, these private times occurred between 1-2 times a month, then twice a year during my relationship and marriage, and then went back to once a month as I was getting older and didn’t want to damage my body anymore than I already had over the years, but that desire remained so I continued it over the next 5 years, during which I met my now wife, who is sexually open, but I’d accumulated so much shame, that I couldn’t bring myself to tell her except one time and very indirectly, to which she gave a clumsy and painful 10 second attempt to which I imagined she’d checked the box that she’d tried it, and it just didn’t do anything for her, nor me, and that was that….

    Well, by this point, I’d thrown away literally thousands of dollars worth of toys away for fear of being discovered, but despite the shame, I’d still get this impulse to have an “alone night” with stimulants and toys that I couldn’t shake until I had completed this ritual, for lack of a better word.

    After one such night, I went well into the next morning pretty much sober still enjoying the stimulation, which I wrote off as being still under the influence, but I held on to the one toy I must have bought 6 different times for a couple of days where I’d use it while sober, and the pleasure was every bit (or almost every bit) as it had been under the influence. As such, I started feeling less and less inner shame, as I figured this was my body and what I do with it, is my business, but it would NEVER be communicated to my wife and lover for fear of rejection or worse, she’s think I was into men.

    Over our first year of marriage, I got to where I enjoyed anal stimulation so much, that it was hurting our sex life because it was just me with my one well hidden toy that only came out when I was sure I had time and could not get caught, OH THE SHAME I imagined would be soul destroying and might even hurt my marriage.

    Over time, I became more comfortable making subtle hints that I enjoyed this stimulation for “health reasons”, something she didn’t seem to disapprove of, though she never asked me what that meant so I read that as a stop sign.

    After about 3 months of this, and several failed attempts to broach the topic directly with her in unequivocal terms, I was staring out the window trying to work up the courage with her sitting right next to me. She knew something was weighing heavy on me, and she asked to which I said “it’s nothing”, which in my head I was chastising myself for not taking that opening to discuss my desires. After sitting there literally terrified of her response, I asked her if she would have any issues with using a toy to stimulate my prostate during our love making sessions. I squinted my eyes in case she was looking at me with a look of total disgust and embarrassment, but when I finally looked directly at her, she was, MUCH to my surprise, smiling and her verbal response was even better than I could have written myself.

    She said, I know you mentioned it before and I tried, but it didn’t seem to be going well, but that she was ABSOLUTELY in to pleasuring me this way, and in fact, she took my hand and slipped it down her panties so I could feel her wetness and excitement at the idea. She asked if I wanted to try it right then, but I was a little caught off guard and now nervous as to what that would entail, especially considering I’ve never had anyone there to participate. I said, no, probably not tonight, she said, fine, it’s settled, we’ll doing it tomorrow, and I’m gonna get all up in your business.

    Tomorrow arrived and with much trepidation we showered and she asked me to turn on 50 Shades of Gray, which I knew was more or less bondage soft core porn, though I’d never seen it, but I know she likes to be restrained from time to time. About half way through the movie, we started playing touchy feely and she abruptly got up and pulled me by the hand to the bedroom where we started making love and she stopped me, and said, I told you today was the day, where’s the lube.

    What followed, was the most terrifying, releasing, mind blowing stimulation from her finger/s, and ONLY because I wasn’t able to relax for the first 20 minutes, as the balance of my shame was leaching out of me with each finger stroke, she led me to the shower where she came up from behind me, and gently pushed my shoulders down, and she inserted her fingers aggressively inside me. It was so much that I had to ask her to stop because my legs were shaking too much, and we went back the bed.

    She was a trooper, and for 30 minutes she gave it every effort, REFUSING to quit when it looked like I wasn’t going to orgasm (Likely because I was so nervous) and she worked me into the most explosive orgasm I can ever remember having. As she got up to go wash her hands, she had this devious smile on her face, and where her vagina had been positioned, was now a 14 inch circle of her wetness on the bed because of the excitement she had derived from offering me that pleasure.

    She enjoyed it, and it was only the first time this last weekend, and if her feedback about it is any indicator, it won’t be anywhere near the last.

    All of this to say, Ruby’s reassurances are dead on, and you should ask for what you want, as what’s the worst that could happen, at least in a committed marriage? The way she put it to me in my post orgasmic bliss probably says it best, as she asked me if there was anything she wanted me to do to her, what would my answer be, to which I responded unequivocally that I would do almost anything and love it as long as it was monogamous, to which she asked, why would you think that I’d feel any different about your satisfaction?

    I love this woman on an entirely new level, and while still a little gun shy, I’m confident that over time, we’ll work out the years of built up shame I’ve accumulated, and we will both enjoy new levels of sexual satisfaction for the rest of our lives.

    I would venture to say that everyone has boundaries that they wouldn’t get into, so the approach is important depending on how “out there” your fantasy is, but if I could create a lover and wife out of everything I wanted in a partner and lover, it would be someone that believes as she and I do, that there’s very little we won’t do for the other sexually or in life because we both are fueled by the others excitement. It’s turned on a light in me that I’d thought was gone, and I think, just maybe, this turned one on for her as well.

    1. Ruby

      I read this comment on podcast #105 and responded to it. Thanks so much for sharing this.

  9. E

    Thank you Thank you Thank you! So encouraging, Ruby!! *hugs*

    1. Ruby

      My pleasure!

  10. Valentino

    Hi Ruby, I am so glad i found Pegging Paradise. For some time i thought that I’m alone in the ‘pegging world’ and didn’t know how to approach my partner about pegging. I’ve also tried some solo anal play, i enjoyed it but believe that pegging would be much better. I started to introduce the topic to my partner. We are going very slowly but believe that we will get there. She already started to play with my ass, kiss it, lick it etc. So i believe before the end of 2015 we’ll end up with a whole pegging session! Thank you for this ‘piece of heaven’ as i really find comfort and learn from the experiences and advice on here.

    1. Ruby

      You are so very welcome. I’m glad to hear you found a safe and comfortable place to be here at Pegging Paradise. Sounds like you are well on your way to enjoying pegging! Let me know when it happens – I’d love to play the celebratory music for you on my podcast!

  11. Brazilian Gal

    Hi, Ruby.

    I love the idea of penetrating a man, unfortunately my country has a very macho culture. I’ve done prostate stimulation with my fingers to an ex-boyfriend once and wow…I could see he had a so intense orgasm that he nearly fainted and I think I came too just to see him so vulnerable and exhausted in ecstasy.

    All I want now is a man to love with all my heart, to get married and have this moment my man would surrender to me. (yeah i am romantic)

    1. Ruby

      Thank you for writing from (macho) Brazil.
      I know exactly how you feel – the thrill of seeing your partner have such an intense orgasm is really amazing!
      I love that you are romantic. Good luck finding exactly the right man who wants to surrender to you!

  12. Daniel

    Dear Ruby
    I can not thank you enough for your work . l have come a very long way since discovering you . Recently you had a question about lube shooters. I think it was misunderstood . I have a lube shooter that an assman can fill with his favorite lube (I prefer Sliquid) which I never knew about until you . Anyhow it basically is a syringe that you fill with lube and shoot in your ass. I purchased mine for $8 at the local porn shop when I decided I wanted to be a size king lol. As the toy was 9″ insertable by 2 1/4 wide figured I’d need as much lube as possible. But sometimes when I use it I get that full feeling. Hoping my experience helps my fellow listener with his question. Anyhow Ruby I have enjoyed ass play since the age of 14 I am now 35. Never thought I would ever have something that big in my ass. It feels so good and it was made possible due to your teachings. Thanks so much. The only thing left on my quest is to be pegged by my beautiful wife. The first time I told her about my interest she freaked out. Since then I have followed your advice of communication and talking about it outside the bedroom. She is very slowly coming around. We haven’t indulged in any ass play yet but I’m certain the day is coming when I get to surrender my ass to my wife. I just wanted to show my appreciation for your work Ruby thanks so much for all you do.

    1. Ruby

      Thank you for clarifying about lube shooters! I didn’t know that a device existed that could be refilled. I thought they were all disposable. Also, thanks for sharing your story about your own anal journey.

      If you have not already discovered it, check out podcast #112. It is an introductory podcast for women about pegging. Give it a listen before you give her the link to listen to. I love how much patience you have with the process! The day that you do surrender your ass to your wife, please let me know, and I will be especially happy to play the music for you on my podcast!

  13. James M.

    I would have to say that pegging will always be in our bedroom! At 1st she wasn’t sure about it but was interested. I knew then she was going to take my ass and I loved just the thought of it and still do haha. The 1st time went great but now it’s out of this world!!! She takes me over and I just submit to her. She owns me and she knows it and I love it!!! I love seeing her with the strap-on and that look she gives me coming to bed. It’s just swinging between her legs!!! I have never cum like I’ve cum while she’s drilling my poor ass. Huge and I mean HUGE orgasms!!!! She doesn’t even touch my penis and I just cummmmmmmmmmmmmmmmmmmmmm everywhere. Even while laying on my back, she watches me and she knows now when I’m about to erupt. She aims my rock hard member at my face and I beg her not to do it, but I can’t stop her and I cum all over myself (Because you can’t stop pleasure, no matter how bad you want to lol). She makes sure I clean up all the mess. Then it’s my turn and she loves being pegged more than I lol. She’s loving this and I am too!!!! I can’t control it!!! SHE CONTROLS IT THEREFORE SHE CONTROLS ME!!! Definitely role reversal, seeing how it feels being on the penetrated side of the game and not the penetrator, and I think it’s great for us and our relationship. I’ve always pegged her and hey it’s only fair guys!!! Let her take you on a ride you will never forget!!! PEGGED FOR LIFE!!!

    1. Ruby

      So happy for you! I’m going to read this on podcast #116
      By the way – technically the word “pegging” only applies to her doing you. If you do her in the ass, that’s not pegging, just anal sex.
      Doesn’t really matter – you two are having so much fun!

  14. C

    I first engaged in pegging in an encounter in May of 2015. I was curious about doing it and a woman I was seeing at the time agreed to use a strap-on on me. She used a 9 incher and we tried it from the doggy style and role reversal positions as shown on the website below-

    http://www.take-it-like-a-man.com/positions.htm

    It was the most incredible sexual experience I ever had especially when I was on my back with the pillow under my ass as I wrapped my legs around her from the role reversal position. The intimacy we felt seeing each other face to face tongue kissing as she pumped my ass with her strap on cock was amazing. She turned me on that night and made me realize how much I enjoyed bottoming for women. That experience made me realize my true fetish and I know it is real as I found I am more sexually articulate when discussing it with the women I am talking to.

    Since then, I have been seeking relationships with women who were into pegging that preferred being a top. If the woman I end up marrying tops me every night in bed, I will be a happy husband. The podcast statement by you in this blog reassures me that my sexual preferences are not strange or perverse and is simply something that desires intimate good consensual fun between me and a woman. I feel completely secure in what I prefer sexually and feel you are right in saying we should dismiss any judgmental sorts who try to mislabel this desire and practice. Your blog is the best Ruby, I look forward to learning everything possible from it.

    1. Ruby

      Wow! Thanks for sharing this! I must say, 9″ is HUGE for the first time. Yikes. Hopefully your ass had been played with previous to that!

      Excellent job on accepting your kinks, by the way. ((hugs))

      I’m going to read this on podcast #122!

  1. Ruby Ryder's Pegging Paradise

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