Let me make the case for a pro to you!
In the pegging world there are many men looking to explore pegging on a casual basis. Unfortunately, there are 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 approach her with the idea. 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.
You can attempt to find a woman who is into pegging. Then 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.)
Some people feel uneasy about buying expensive equipment when you aren't sure if you will even like pegging. Some wonder whether that equipment will fit her correctly. Or you could be concerned whether she will be able to have an orgasm, if she even wants to. Also, the steep learning curve might 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. 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 - those are all still paths you will travel. But you have the foundation of a trusting, loving, communicative relationship to contain it all. This can 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.
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. Nor do you 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 very likely to be safer, cleaner and more knowledgeable than the woman you met at a party who says sure, I'll peg you! It's her job. Professionals offer the ability to tailor the experience to your desires and fantasies. They also have 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. 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.
Lastly, to all you lovely sex workers out there:
...for everything you do, for all you know and for all you give.
Listen to these two podcasts - interviews with a man who made the decision to go to a pro and what happened!