Should a 27 year old virgin lose his virginity to an escort?

I’m 27 year old man and am still a virgin. I’ve kissed anybody either. I would never admit this to a woman I’m dating of course but I fear my inexperience will show when it comes time to kiss/make-out and have sex. For that reason I’m thinking of just hiring an escort for a few sessions and getting this over with. What do you all think?

By escort, do you mean prostitute?

If so, I’d start by asking if prostitution is legal and regulated in your jurisdiction. If not, stay far away, because the illegal sex trade (precisely because of its illegality and subsequent existence in the shadows) is a magnet for slavery, underage prostitutes and all manner of other abuses.

If you live in Latin America or somewhere else where everything is legal and above-board, that’s a separate issue.

Do what you want to do, I’d avoid doing something just because you think you should.

A decent woman isn’t going to care how inexperienced you are, most people are looking for an emotional connection not an expert fucking machine.

Just so ya’ know, kissing ain’t gonna happen with a prostitute.
Also, comparing sex with someone who wants to have it with you verses someone who is getting paid to have sex with you is like comparing apples to oranges.

I strongly advise you NOT take anything you learned from boinking a prostitute and using it with a would be love interest.

Depends on where you are, I think. If you book a trip to Thailand, it’s apparently possible to get a “full girlfriend experience”.

Of course, there may be downsides as well as upsides to that… :wink:

Paging Siam Sam or other locals for possible details.

Questions like this make me lose even more faith in humanity.

If I were her & I found out about it & she very likely will, I’d likely want to kill you. Not just for the horrible disrespect to me & our relationship, but God forbid she’d pick up any disease you’d also likely pick up (assuming you’re in a relationship & pondering this idea).
It’s a shit-hammeringly stupid idea. I’d NEVER want to be with a guy or even be friends with a guy who’s been to prostitutes.
As you mentioned, hiding the idea just makes the idea even worse for a potential girlfriend to come along & date you not knowing the sexual health risks & the mental immaturity that this line of reasoning comes from. Run far away from this idea & never look back!

As was mentioned, sex trafficking & slavery is a horrible problem & you would very likely be contributing to it.

I wouldn’t pass any moral judgments on this, but frankly the downsides outnumber the upsides.

As stated before you’re not going to get a realistic experience that will make you better in any way with your real life partner and there are significant risks like STDs and legal trouble.

If you understand these issues and st5ill just want to get laid go about it carefully, VERY carefully.
Go to Nevada or someplace else near you where it’s legal and regulated if at all possible.

There is a non-zero probability that you already are.

Legal considerations aside, it can be good to reduce your anxiety and show you there’s not that much to worry about. If you’re worrying about being “good,” don’t; many people who have had sex are awful. That part is not hard as long as you are willing to be selfless and willing to learn.

On first read it sounds like you were dating someone currently and that’s a shitty thing to do. It seems more about a hypothetical GF on second read, Lydia Phalfav and if so then I am more neutral. No experience but I imagine some prostitutes kiss, this isn’t Pretty Woman. Martian Bigfoot has the key word for that that I see in the back of alternative weeklies if you’re looking for that sort of thing.

And if anxiety is the issue, I can’t imagine actually seeking potentially illegal sex is any less anxiety-provoking.

There are different types of prostitutes. My understanding is that most of the slavery, etc. is in the street-walker trade, not the escort-service trade. But I concur that looking in a legal, related jurisdiction would be safer.

I’m more curious why you’ve never kissed.

Your also assuming that most women your age are more sexually experienced.

Frankly any woman who would drop you just because the sex wasnt so great isnt worth having. If she truly cared and knew you were inexperienced she would work with you on it by telling you what she likes and if you listen, I think she will keep you around.

Some women would be perfectly charmed to be with an inexperienced guy who was interested in slowly and gently learning the ropes under their tutelage. Provided he was good-humored and not-creepy about it, and attractive on some other level (if you’re failing on those points, you have other things to work on before mechanical aptitude ever comes into play).

Firstly, as someone else said 27 is not that late in the game so that inexperience should cause universal derision or suspicion.

The OP’s proposed course of action (once he covers the very real and valid caveats about legality, safety and sexwork conditions) could assist with the strict mechanicals of the event, help avoid some of the most blatant “what goes where/wait it does THAT???/whoa, in porn this didn’t seem quite so slimy/my leg went numb” type fumbling; BUT: it would IMO do little or nothing to help with how he handles the phase that builds up and gets you to the sex point in normal mating, and that phase is IME the trickier part of the deal for the rookie. Were I him I’d work on getting at least to the kissing point in regular dating first.

Or have had sex with someone who has…

And many would be weirded out by a guy who hasn’t yet even kissed somebody at 27.

If your virgin status makes you nervous wrt your first hypothetical relationship, then go for it. Really, it doesn’t matter much either way. It’s not like a couple intercourses with a prostitute is going to turn you into an experienced lover, but if you think it will prevent you from having a nervous breakdown with your first girlfriend, and the idea is terrifying you (or prevent you from seeking a relationship in the first place), why not.

I spent a few years with an older escort. Low point of my life.

It was all I could afford. The hatchback part was ok, but it was a pos otherwise. Traded it in on an Accura Integra, then got a jeep.

ETA: nm, apparently this is another sex thread.

Honestly, I’d say go for it just for the sake of getting that mental block out of the way. Being an adult virgin can be difficult. If you don’t have issues with it, then there’s no real reason to do it beyond “I want to have sex”. As others have stated, it’s not likely to be much like a real sexual encounter - more akin to porn where you’re part of the cast. Just be aware of the reality, and treat it as such. You wouldn’t try to put moves from Busty Babettes 5 on a significant other; treat experience with a prostitute like that.

But if you want to, well, not a whole lot of reasons not to. It’s just sex.

Wait. Are you a) thinking about doing this because you’re unable to find a woman any other way who is willing to have sex with you, you’re tired of waiting, and you really need to get your rocks off?

Then yes, go for it.

Or are you b) saying that you are in a position where you can actually hook up with someone, but you’re just worried that they’ll be put off by your lack of experience?

In that case, no, don’t do it! Who cares if you’re inexperienced? Don’t be silly. Just hook up already. You’ll figure it all out within a few minutes. It’s nature.

Think carefully about your answer. It matters.

If it is causing you undo anxiety, to the point that it is really affecting your life, I think it’s fine. It’s not like you’d be the first person to take that route. Be safe, be smart and do enough research that you feel like you are choosing an ethical form (which may not be the same as a legal form, IMHO). There are plenty of reviews online where you can get an idea of what to expect.

If you are just doing it because you feel like you have to, I’d think it through a little more. The experience probably isn’t going to be any more pleasant than you can achieve on your own, and it probably won’t turn you into a sexual superstar.

What age exactly is inexperience likely to cause universal derision or suspicion? For a man at least. From my experience by the time you’re a senior in high school virginity is non-existent. And for those of you who are wondering I don’t have a girlfriend. The part about how I’m afraid she might find out I’m inexperienced was hypothetical.