In the pegging world there are many men looking to explore pegging on a casual basis and not many women who are ready to sink it deep inside them outside the structure of a relationship. When I get letters from these men or find threads asking if there are any women who want to peg them I usually suggest the men either go to a professional or look for a relationship with a woman who is sexually open-minded and attempt to convince her to try it. The relationship route requires patience, dedication, timing and has no guarantee of success, sadly. And perhaps the man is not desirous of a relationship in his life; he just wants to try pegging.

When I suggest the option of a pro, I often see some variation of this response:

Never paid for sex in my life and not going to start. I don’t recommend anyone pay for something you can get for free.

Judgment about sex workers frustrates me. They rock.

But let’s explore this. Can a man find a partner who will peg him for free? Sure. Is it a difficult thing to do unless he is incredibly hot, single and awesome? Well, judging from all the posts on just about every pegging group that allows personals around the internet, I would say the answer to that is an unequivocal yes. Perhaps less difficult if you are from the younger generation (20’s) who seem to be more open-minded around pegging and sexuality in general. But still far from an easy task to accomplish. There are men on forum boards I frequent who have literally been looking for years without success.

Are there actually women out there who love to peg men and would enjoy a wild night of pegging with a relative stranger with no monies exchanging hands? Yes, there are a few here and there. They are exceedingly rare and are usually seeking out the incredibly hot, single and awesome men.

 

For a single man who has never tried pegging, let’s examine the comparison between going to a professional and trying to find a woman to peg him for free.

For Free

You can attempt to find a woman who is into pegging. You can approach a woman you have just met about pegging and possibly have her reject you as a result. You can worry about whether she will go and tell everyone in your social circles that you want to be fucked up the ass after she rejects you. (This may not be a concern for all of you, but if it is, it is a very real concern.)

You can feel uneasy about buying expensive equipment when you aren’t sure if you will even like pegging. You can wonder whether that equipment will fit her correctly and whether she will be able to have an orgasm, if she even wants to. You can worry about whether the steep learning curve will frustrate her and she will refuse to try it again after the first experience. You can hope that she will not hurt you, in her inexperience. And you can hope that the communication between you will be adequate to facilitate a good experience, because good communication is essential for pegging. And good communication takes time to develop.

Don’t mistake me here…experiencing the adventure of strap-on sex with a partner who you are already in a relationship with can be an amazingly life-changing experience. All of those equipment questions, the communication, the learning curve, the making sure you don’t get frustrated or hurt and both of you find pleasure are all still paths you will travel, but you have the foundation of a trusting, loving, communicative relationship to contain it all and help you find your way through any mis-adventures to the ecstasy. You do not have that foundation with a woman you just find and ask to peg you. You can certainly put your efforts towards finding a woman, starting a relationship with her and then asking her. But this option is only good for those men looking for a relationship.

I am not saying that experiencing pegging with a relative stranger never works; it can. But for all the reasons I have outlined, the odds are completely against you, unless you are incredibly hot, single and awesome.

The Professional

Consider the contrast of the professional experience. You contact her. She communicates with you (part of her job) to discover exactly what kind of experience you are looking for. Are you looking to combine a couple of other kinks with the pegging to enhance the experience? Are you completely new to anal play? She asks many questions to discern exactly what you need. She will give you instructions on how to prepare for your visit to her. When you go to see a professional, it is in her best interest to provide you with an optimum experience to the best of her ability so that you will be a satisfied customer and hopefully return or recommend her to others.

You do not have to worry about her inexperience or being rejected by her because of your desire for pegging. You do not need to be concerned about her pleasure or selecting (and paying for) the right equipment. You get to experience pegging for the first time…with someone who knows exactly what they are doing and wants you to have the best experience possible. She will keep your secrets, too!

Additionally, a professional is certainly likely to be more safe, clean and knowledgeable than the woman you met at a party who says sure, I’ll peg you! It’s her job. What professionals offer is the ability to tailor the experience to your desires and fantasies as well as the knowledge to make it happen safely and satisfyingly. You are paying them. It is an equitable exchange; a win-win as it were. Doesn’t that take the stress out of the equation and just let you relax and enjoy? Think about it.

With a professional, you can live out that pegging fantasy just the way you want. And if you discover that you like pegging, then you can bide your time and find a woman when the time is right and try to convince her to try it. Or, you can just continue to get your pegging with professionals and never seek out a relationship if that’s what you want.

I encourage all you “I need a woman to peg me!” guys to consider a professional. It is a valid option for men who want to explore the world of pegging apart from all the complicating factors of a relationship.

(And if you are married or partnered and you go to a professional sex worker – just don’t tell me about it! I tend to have an overemphasis on integrity and honesty and then the self-righteousness comes out…it’s not pretty.)

 

Lastly, to all you lovely sex workers out there:

Thank You.

…for everything you do, for all you know and for all you give.

You rock.

4 Comments

  1. Hello Ruby,

    I just read your article about sex workers. I have just recently found my pegging fetish and I am very interested in how this works. I have no idea where to start. Is redbook how you start?

    • I don’t have any advice on where to start, unfortunately, but these two podcast interviews might be of interest to you – I spoke with a man twice who went to a pro to experience pegging for the first time. He does have some suggestions about looking for the right one.
      He Went to a Pro
      To the Pro Again

  2. To any man who would respond in the way Ruby described above: “Never paid for sex in my life and not going to start. I don’t recommend anyone pay for something you can get for free.”, I say this…

    You’re an idiot.

    You may well be content with your miserable existence, passing judgement on those who fail to measure up to your self-prescribed high moral standards, but you always seem to forget the most important thing.

    Idiots don’t matter.

    Sex workers are a wonderful bunch of people who provide an essential service. Yes, they can be the source of conflict for people in a relationship, but they can just as easily be the solution too.

    In the context of pegging, they are nothing less than Angels, facilitating access to an activity that simply can’t be done by oneself.

    So, for those of us who employ the services of sex workers, please spare a thought for those who are recommending that you shouldn’t be paying for what you’re getting, especially if you’re getting pegged. Schadenfreude; guaranteed to bring a smile to your face.

    • Hey Harry,
      Thanks for your comment, and your support of sex workers. I’m quite sure the single men who use the services of sex workers are getting pegged a lot more than those who don’t!
      And for my readers…

      Schadenfreude – German, pleasure derived from the misfortunes of others.

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