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Questions about penis size

I love questions about penis sizepenis size questions Experienced Mistress Olivia 1-800-721-1962

I’ve said it before and I’ll say it again, penis size DOES matter.  Honestly, if you have to ASK then ….. laughs …. you know the answer and are probably into small penis humiliation.  Oh, and remember, sensual humiliation is STILL that thrill and sting of your embarrassment.

Tiny guy and his questions

He asks a LOT of questions so I’ll answer them here on my blog every now and then.  Here are a couple questions that made me laugh.
“Do you think it is true – like your experience that after a woman has a big one that she then wants that size?  Do you think that is usual for women?”
Short answer:  DUH!  ~laughs~  So if you have a little dick then even a woman that only has experience with the average-sized penis options will find you … ahem … lacking.  But there’s more to it than mere size.  Your dainty dangle means that you’re a beta male through and through.  There’s no contest between an Alpha male and a beta male.

Make up for your shortcomings

I can tell from THIS question that this guy knows that he has to do something extra to get the attention of a woman — and even more when he’s trying to talk with a beautiful woman.  Here are the questions:
From your experience as a phone mistress or just as a woman do you think small men feel they need to “make up for it”to women they try to date? Do you think women feel that way as well – consciously or sub subconsciously?
Again, short answer yes.  Longer comment — if you have no dick you’d BETTER bring something else to the relationship!  ~laughs~

Your Experienced Mistress,

Ms. Olivia

15 comments to Questions about penis size

  • John Q


    By “bring something else to the relationship” you wouldn’t be suggesting bring a man, would you?

    In my personal experience the most natural position in any relationship with a woman has been solidly in the friend zone. At least, that’s how it was for me until I you came along and showed my girl some better options.

    Love you though. At least I HAVE a girl friend thanks, in no small part, to you.

    But then, a “small part” is the operative but unused factor, is it not?

    John Q

    • Olivia

      Well …. as you have now discovered through our therapy sessions …. bring something else WILL mean that she has a “real man” in her life. But remember, SHE might choose to enjoy a relationship with you for the “other” things you bring: friendship, support, etc. When I first met your GF she told me that she adores your company but was so profoundly DISAPPOINTED in your … ahem … attributes that she wanted to break up.
      Yes I DID talk with her to help her discover that maybe just “breaking up” isn’t in her best interest. She really had NO IDEA of the full range of her options.
      I think it’s safe now to assume that she has a much better understanding of what she DESERVES out of life.

      And, HEY, at least YOU get to keep a girlfriend — I mean, you KNOW you’re always going to be in the friend zone but before this GF, you always got DUMPED … now, at least you still have …. ahem … companionship.

      • John Q


        Yes, as you mention below, I do feel fortunate. Not exactly lucky, but not being rejected and dumped is a major improvement. Thank you. There are, of course, other things that I’ve had to get used to, but she’s happy. I don’t think I’ve ever had a happy girlfriend before. You know?, the friend zone is a bit different this time. She sees me more as a girlfriend. Truthfully, with my closet full of dresses and pumps … well, you get the picture.

        Hey, sent you a bit more wish list stuff. Hope you like it. Slow boat from China shipping. Guess I should activate Prime.

        You said on a previous post response: “I didn’t “get” humiliation with someone I genuinely like and respect …. and then one day, WOW I GET IT !!!!!.” That really resonates with me. I don’t think I could get as deeply into it any other way. Maybe it’s a spectrum. On one end you have porn and your hand … and a totally forgettable experience. On the other end you have intimacy, vulnerability and trust … and an unforgettable experience. I’ll take that kind of depth any day..

        I read sub-text decently well … and I see glimpses of the real you behind the curtain. In some parallel universe, we could be mates. I like that.

        You were talking about novelty and exploration in an earlier comment to me. You asked if the need to explore is the way it is for me too. Most certainly. I get get bored quickly. I love steep learning curves. I need to be challenged. However, when it comes to people, I don’t do musical chairs well at all.

        But then, I’m confident you know that about me by now. You’re my Mistress. And, of course, my trusted therapist.

        John Q

        • Olivia

          WOW where do I begin?
          You DO get to peek behind the curtain … not just here reading subtext but also I tell you things in our emails on our calls … we would have a BLAST together! Naughty and nice and interesting and intimate … you know, all of the above and more. You’re a wonderful soul, man, naughty dude, pitiful cuckold, haahhahahahahahahaha in short you’re the total package too 🙂 🙂

          I know you got my email about that AMAZING Betsey Johnson pink baseball glove handbag …..
          That is the BEST !!!!!!!!!!!!!!
          You know I’ll pair that with my Bartolo Colon Mets jersey (yeah I’m still mourning the loss of Big Sexy — I do like people who are “outliers”) and my snazzy Mets earrings. I’m going to Citi Field for a subway series game this summer so you’ll be there with me …. I won’t be catching a fly ball with my purse though! Actually, I’m the one that goes NOOOOOOOOOOOO and ducks behind someone big!

          OH and I love your thoughtful and insightful comments so much — I’m actually going to use a bunch as inspiration for blogs — you know I adore the thoughtful blogs (although they have been called boring by some who just want the crotch shot type of writing — DILLETTANTS pffffffffttttttt.

          More in the email that will be to you shortly! 🙂 🙂

  • Petey cream puff

    For it you putting me in panties/bra/slip/dresses along with wig/lipstick kisses on my cheeks along with feminine arched eyebrows/makeup and keeping me as your cream puff girl making out with me on your bed with Ms Delia taking pictures of you on giving me lipstick kisses on my cheeks as well sitting on your lap and you sitting in my lap. Im 2-3’ but when you & Ms Delia did this to me I got hard as it’s only way.

  • Alex

    Yes, a guy better bring something to the table. However, don’t think that if you have something else to offer, your lady will stop hooking up with the well-hung guy. It doesn’t work that way. See, your gf, or wife may say she loves you, however she has a stornd desire to be physically satified. As long as she has her stud on the side, she gets what she needs, so she is free and in the mood to spend non-sexual time with you.

    • Olivia

      Well … I meant she might want to spend non-sexual time with you — honestly, if you don’t measure up sexually then OF COURSE she will get her physical desires and needs elsewhere. You’re lucky she spends ANY time with you at all 🙂 🙂 laughs

  • Alex

    Yes, you are right Ms Oiliva. You know us very well. Then again , comparing my 5 incher to my wife lovers 9 1/2 incher, is like comparing a Yugo to a Ferrari.

  • marlowecv3

    You always said no no no to me due to my tiny penis.

    It made me want you more.

  • mike

    I think that for guys your penis is your “manhood”. I think that it is felt like it is what is used to “conquer” a female. It may not be quite that explicit but there is a sense that “that” is you and if you are small or tiny you feel you cannot “conquer” or as you hear – “take” her. It is like not having a kind of power. It makes you feel like you have to defer to “her” and/or be compliant. I have heard women say this almost precisely like that. I will never forget hearing a girl at college chatting with her friends and saying “little guys BETTER be agreeable”. (she was talking about endowment size). It blew me away that she thought like that. It was the first time I wondered how often girls thought like that?

    • Olivia

      She DEFINITELY was talking about penis size when she said the guys with a small penis had BETTER be agreeable. Oh and to answer your question … SMART women think like that all the time, most women think like that most of the time (unless there are extenuating circumstances) and only very foolish women treat a “guy” like you like a man.

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