Ask Dot :: I want to get pegged, do I ask a transgender girl to help out?

For everyone who would like to wag a finger at this question: unless i find someone’s ignorance purposefully offensive, i’m going to assume honest naivety. especially in matters that remain relatively new to mainstream thought.

in the current social whirlwind that expects everyone to know everything, we’ve lost sight of the fact that people need to ask questions if they’re going learn anything of value. google isn’t enough if you don’t know what you’re supposed to be searching for.

in the lovely, much smarter, words of carl sagan: ‘There are naive questions, tedious questions, ill-phrased questions, questions put after inadequate self-criticism. But every question is a cry to understand the world. There is no such thing as a dumb question.’

your very best friend

Hi Dot.

I am a straight guy who until a couple of years ago just had normal straight sex. Then I met a girl who turned my life upside down where sex is concerned. She introduced me to anal and I now have a very strong anal fetish. Recently, I was pegged for the first time and my life has irreversibly changed. I can’t get enough of it. At one stage I even thought I was gay. I actually went on a date with a guy, it did not work…lol. I eventually went on a date with a transgender girl and I must admit I did enjoy the occasion, but purely for the reason that I wanted to find out if have sex with her would be like being pegged. Is there something wrong with me? Having sex with a guy puts me off completely, but being penetrated by a transgender lady or being pegged excites me endlessly. What do I do??


Ok. I’m going to dispense with the eyebrow raising at everything that is wrong with the wording and ideas in this question, and aim rather to address them as a learning moment for you and other readers, while we help you along your way to finding the right person for you. let’s get started (we’ll work in order of your letter)…

Anal play for straight men

first off, how wonderful for you to find such pleasure in anal sex. i wouldn’t call it a ‘fetish’ though. i’ve provided a link at the end of this that will explain fetishes in more detail. but considering the fact that the anus is the most direct way to stimulate the male prostate, or the male ‘p-spot’, it’s surprising more men aren’t into anal play for themselves.

Screen Shot 2015-08-19 at 10.43.59 PM

‘Gay’ does not equal ‘anal sex’

now, while i think it was grand that you were open-minded enough to consider your sexuality as non-static, and went on a date with a guy, you – and many, many others – need to know that enjoying anal play as a man DOES NOT ‘MAKE YOU’ GAY.

‘gayness’ and anal sex are not mutually inclusive. some gay men practise anal sex both as ‘givers’ and ‘receivers’ – or as a ‘top’ or a ‘bottom’. some prefer one or the other. some have never practised anal sex in their life. some don’t like it.

likewise: some straight men love anal play and enjoy being pegged. some wouldn’t try it in a million years. however, i would argue that their reluctance has less to do with actual preference and more to do with homophobic associations with anal sex.

Vanilla sex and kinky sex

therefore, the term you are looking for is not ‘straight sex’ (as in: you used to have ‘normal straight sex’), the term you are looking for is ‘vanilla sex’. and even so, i am not comfortable with the very ill-defined distinction between what constitutes ‘vanilla’ sex (ie heteronormative, missionary, unimaginative) and ‘kinky’ sex.

it's all a matter of context

it’s all a matter of context

Transgender women

ok. now. i’m choosing to imagine that you’re not fully appreciating how completely off centre and offensive you’re being with this part of your thinking. i’ll provide a few links below for further reading, but in short and in particular reference to the woman you tried to date:

  • A transgender woman who has chosen not to (or is maybe unable to, usually for financial reasons) undergo full gender reassignment surgery will still have her male body.
  • Many women in this position feel very uncomfortable with this fact. Many are ok with it. the point is: you cannot assume she has a penis, and even if she has, that she will want to use it – and then if she would like to use it, that she will want to use it penetrating someone else.
  • Also, a transgender woman may be straight, she may be gay – the sex of her body has no bearing on this. you could’ve gone on a date with a lesbian trans woman who is about as inclined to sex with men as a lesbian cis woman might be.

People are not objects

the main vibe i’m getting from your question is that you genuinely seem to think that anything with a penis – man or woman – is an object that may be able to accommodate your need to be pegged.

if what you’re looking for is solely a sex experience, you don’t go on ‘dates’ to try people out for size. once you’ve educated yourself a little bit more in this particular sexual expression (see below), you will know better (hopefully) how to meet women whose sexual tastes suit your own.

there is nothing wrong with you and what you like, but there is a lot wrong with how you’re going about trying to find out how to get it.

please, whatever you do, do NOT date a transgender woman again only to find out if a body part she may or may not have has a use for you.



Here is what you do instead

you go online, to forums and sex sites, and find out about pegging and femdom. you set up a profile outlining what you’re into, namely: women who would be willing to use their penises or a strap-on to fuck you. you find like-minded people and realise that your desire to be pegged by a woman is really quite common.

in the meantime, you buy any number of anal play toys available online to keep you and your penetration pleasure seen it. (try the prostate massagers from mantality)


 some links i suggest you take a look at: