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  • Olivia Lush

Pleasures of The Back Door



In my career as a high-end legal companion I aim to help my clients explore their hidden desires and sexual fantasies that many times they are not comfortable putting in practice or even talking about with their partners.


What I call “the pleasures of the back door”, to make it easier for the shy ones to talk about, were always a popular request, but on the last couple of years they seem to be more and more in demand.

By “Pleasures of The Back Door” I mean prostate massage, toys for boys, going from butt plugs to prostate massagers and dildos, pegging, also known as strap-on play, and fisting.



For the purpose of this column, I am concentrating on prostate massage, sex toys and pegging as these are the requests I get more frequently.


Although the word pegging seems new to many people, the practice is not new. You can actually find it in porn movies as early as 1970.

The biggest taboo with male anal sex is the believe that a man enjoying anal pleasure might mean that he is homosexual. Let me make it very clear to you: The fact that you enjoy it does NOT make you homosexual (what would not be a problem, but that’s a different conversation). It just means that you found another amazing way to have pleasure in areas that arouse you, and that makes you very fortunate indeed. Many men enjoy anal play because it stimulates their prostate, what’s believed to be the male G-spot.


With prostate massage, sex toys and pegging, everything should be started slowly and with lots of lube. My general rule is if it hurts, you stop. It should be fun and pleasurable, not painful. When it feels good, you know you can go faster or deeper. Communication is key.

The same rule works for me with sizes. If someone contacts me for a session and has no experience, I know to start with smaller toys to see how receptive he is, even if he asks to start with big ones. You know the saying “The eyes were bigger than the stomach”, well, sometimes the eyes are bigger than their bum bum (Portuguese word for butt).

If they have experience, I’ll ask which size toys they usually play with, so I have an idea of where to start. Again, communication is always key for a fun, pleasurable and safe session.


With pegging comes a power exchange that is very exhilarating. The pleasure, the letting go, the vulnerability and being respected after all without having to prove that they are always the alpha male expected by society makes the experience so special. The total freedom of letting go, being yourself, having pleasure without being judged is extremely important and could be very satisfying .


You could make your own story that could go anywhere from a humiliation BDSM scene to a very sensual scenario where no humiliation is involved, and you are actually making love respecting your original orientation. The role play possibilities are many or it could be a part of your romantic encounter where no story is necessary.


I am not advocating for you to go knocking on the back door if that’s not something you’ve been craving or even remotely curious about, but I am saying that if you’ve been smiling at the thought of exploring that area, maybe a friendly well lubricated finger or two strolling in that direction might guide you to a secret passageway of hidden pleasures.





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