# Should a 27 year old virgin lose his virginity to an escort? **URL:** \ **Category:** In My Humble Opinion\ **Created:** [December 15, 2014, 7:09am UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270 "2014-12-15T07:09:52Z")\ **Posts on this page:** 20\ **Page:** 2
**Author:** ![even\_sven](https://avatars.discourse-cdn.com/v4/letter/e/dfb087/32.png) [@even\_sven](https://boards.straightdope.com/u/even_sven)\ **Post date:** [December 15, 2014, 1:10pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/21 "2014-12-15T13:10:49Z")
(Also, if you are already in a relationship, commercial sex is definitely off limits.) ---
**Author:** ![Freudian\_Slit](https://avatars.discourse-cdn.com/v4/letter/f/5daacb/32.png) [@Freudian\_Slit](https://boards.straightdope.com/u/Freudian_Slit)\ **Post date:** [December 15, 2014, 1:14pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/22 "2014-12-15T13:14:06Z")
> [@Shakes](#): > > Just so ya’ know, kissing ain’t gonna happen with a prostitute. I always thought that was a myth. Why wouldn’t they? Supposedly it’s too intimate, but people kiss in nonintimate sexual encounters (one night stands, etc.)–I never got that. ---
**Author:** ![PookahMacPhellimey](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/pookahmacphellimey/32/3175_2.png) [@PookahMacPhellimey](https://boards.straightdope.com/u/PookahMacPhellimey)\ **Post date:** [December 15, 2014, 1:14pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/23 "2014-12-15T13:14:39Z")
I think it’s a bad idea. Or, at least, an indifferent one in that doing this or not won’t make much difference to the outcome of your dating life. There have been various threads asking women if someone being a virgin at age x would be a deal-breaker. For starters, to me 27 is not yet even in that zone. But even if, what the deal-breaker was for me and many other female respondents is not the lack of mechanical what-goes-where knowledge, as much as the worry that the absence of certain social skills was the underlying cause of the - presumably unwanted - virginity. The fact that you seem to think the mechanics are a big obstacles indicates to me that, perhaps, you need to lay the accent more on the social skills aspect and meet a woman you like and can be open with. ---
**Author:** ![Don\_t\_Panic](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/don_t_panic/32/398_2.png) [@Don\_t\_Panic](https://boards.straightdope.com/u/Don_t_Panic)\ **Post date:** [December 15, 2014, 1:23pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/24 "2014-12-15T13:23:04Z")
> [@TheBuilding](#): > > What age exactly is inexperience likely to cause universal derision or suspicion? For a man at least. Probably no particular age at all, if you’re reasonably attractive otherwise. Or at least more or less a normal person. Of course, the \*reasons \*for involuntary prolonged virginity might cause derision or suspicion. Say, if it is caused by the fact that you’re oozing pus from all bodily orifices, or that you’re the size of the Hindenburg, or that you enjoy dressing up like a chicken, and have a history of running around making “baaach-baaach” sounds and flapping your arms at formal social gatherings… that kind of thing. But the virginity itself? Nah. It’ll probably even intrigue some people. Edit: Actually. come to think of it, I suspect that there might be a valley of derision and suspicion. It starts some time in high school and lasts for maybe a few years. So the good news is that you’re out of it. ---
**Author:** ![monstro](https://avatars.discourse-cdn.com/v4/letter/m/ba9def/32.png) [@monstro](https://boards.straightdope.com/u/monstro)\ **Post date:** [December 15, 2014, 1:29pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/25 "2014-12-15T13:29:16Z")
If you can afford it and it’s available in your area AND you really think you’d benefit from it, you may want to consider working with a sex therapist. This is controversial, but sometimes they will arrange for you to work with a sex surrogate. But I imagine this is something you’d only want to consider if you have a psychological or physical disorder. Just being a late-bloomer wouldn’t qualify. If you are too embarrassed to let your girlfriend know that you’re inexperienced and feeling anxious about it, you may not be ready to have sex with her. You really can’t say you’re in an intimate relationship if you can’t be honest about something like this. ---
**Author:** ![TheBuilding](https://avatars.discourse-cdn.com/v4/letter/t/aeb1de/32.png) [@TheBuilding](https://boards.straightdope.com/u/TheBuilding)\ **Post date:** [December 15, 2014, 1:31pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/26 "2014-12-15T13:31:08Z")
> [@monstro](#): > > If you are too embarrassed to let your girlfriend know that you’re inexperienced and feeling anxious about it, you may not be ready to have sex with her. You really can’t say you’re in an intimate relationship if you can’t be honest about something like this. Really? I was sort of conflicted between getting experience with an escort or just going with the flow and kissing/having-sex with her without talking about my inexperience. Telling her never entered into the equation. ---
**Author:** ![monstro](https://avatars.discourse-cdn.com/v4/letter/m/ba9def/32.png) [@monstro](https://boards.straightdope.com/u/monstro)\ **Post date:** [December 15, 2014, 1:50pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/27 "2014-12-15T13:50:23Z")
> [@TheBuilding](#): > > Really? I was sort of conflicted between getting experience with an escort or just going with the flow and kissing/having-sex with her without talking about my inexperience. Telling her never entered into the equation. Imagine yourself saying, “Honey, I have something to tell you. It’s so hard to say to this, but here goes: I am very inexperienced when it comes to sex. I may have made it sound like I’m a big horndog in the past, but I’m sooo not. I love you so much and I want to be with you, but I’m feeling nervous about how I’m going to perform. I just need to know how you feel about all this before we actually do it.” Is your girlfriend really going to laugh at you? If she does, she’s not the girl for you. And it wouldn’t be fair to you to stay with her, because no one deserves to be with someone who laughs at them. Chances are, your girlfriend will not laugh at you. She may not be 100% thrilled, but she will likely be touched that you trust her enough to tell her the truth. For all you know, she also has her own secrets. Being honest may take your relationship to another level. ---
**Author:** ![RickJay](https://avatars.discourse-cdn.com/v4/letter/r/bb73d2/32.png) [@RickJay](https://boards.straightdope.com/u/RickJay)\ **Post date:** [December 15, 2014, 2:16pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/28 "2014-12-15T14:16:35Z")
Where the OP is has a lot to do with this. Prostitution is illegal in the USA and so this would constitute a risk; it’s legal, more or less, in Canada, so it wouldn’t. Having said that it was not clear to me from the OP that he had a girlfriend. If he does, which I now think is the case, dude, just kiss her and have sex with her. It really is not that difficult to get the hang of. ---
**Author:** ![CalMeacham](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/calmeacham/32/35_2.png) [@CalMeacham](https://boards.straightdope.com/u/CalMeacham)\ **Post date:** [December 15, 2014, 2:25pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/29 "2014-12-15T14:25:51Z")
> [@monstro](#): > > Imagine yourself saying, “Honey, I have something to tell you. It’s so hard to say to this, but here goes: I am very inexperienced when it comes to sex. I may have made it sound like I’m a big horndog in the past, but I’m sooo not. I love you so much and I want to be with you, but I’m feeling nervous about how I’m going to perform. I just need to know how you feel about all this before we actually do it.” > > Is your girlfriend really going to laugh at you? If she does, she’s not the girl for you. And it wouldn’t be fair to you to stay with her, because no one deserves to be with someone who laughs at them. > > Chances are, your girlfriend will not laugh at you. She may not be 100% thrilled, but she will likely be touched that you trust her enough to tell her the truth. For all you know, she also has her own secrets. Being honest may take your relationship to another level. My first time, I admitted to my girlfriend that I had a horrible secret – I was a virgin. She was actually relieved. She thought I was going to tell her I had a wife hidden away, or something. And it turned out that she had a cure for virginity. ---
**Author:** ![Hector\_St\_Clare](https://avatars.discourse-cdn.com/v4/letter/h/b5ac83/32.png) [@Hector\_St\_Clare](https://boards.straightdope.com/u/Hector_St_Clare)\ **Post date:** [December 15, 2014, 2:36pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/30 "2014-12-15T14:36:54Z")
> [@Lydia\_Phalfav](#): > > 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. For what it’s worth, I think ‘sex trafficking is a problem’ mostly because the sex trade is _illegal_ in America, and I’d favour legalizing it, partly to deal with this problem. If it was legal, then I don’t think this would be so problematic. (I’m still not a fan of prostitution or other forms of casual sex for moral reasons, naturally, but immorality alone is not a good reason to ban something). If you are dead-set on paying an escort, and don’t have any religious or otherwise objections to casual sex, **TheBuilding** , you could fly to Mexico or the Dominican Republic. ---
**Author:** ![clairobscur](https://avatars.discourse-cdn.com/v4/letter/c/839c29/32.png) [@clairobscur](https://boards.straightdope.com/u/clairobscur)\ **Post date:** [December 15, 2014, 2:41pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/31 "2014-12-15T14:41:07Z")
> [@TheBuilding](#): > > 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. I don’t think virginity is non-existent in senior high school. The average age of first intercourse in the USA (assuming you’re American) is 17, so many still didn’t have sex when they leave high school. However 27 is way up in the extreme range. Some women won’t care about it. A lot of them, however will consider you not having had a relationship (not just not having had sex) at 27 as a big red flag. ---
**Author:** ![clairobscur](https://avatars.discourse-cdn.com/v4/letter/c/839c29/32.png) [@clairobscur](https://boards.straightdope.com/u/clairobscur)\ **Post date:** [December 15, 2014, 2:57pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/32 "2014-12-15T14:57:57Z")
> [@monstro](#): > > If you are too embarrassed to let your girlfriend know that you’re inexperienced and feeling anxious about it, you may not be ready to have sex with her. If people didn’t have sex until they don’t feel anxious about their first time anymore, everybody would die a virgin and the human race would go extinct. _Who_ wasn’t anxious the first time? > [@](#): > > You really can’t say you’re in an intimate relationship if you can’t be honest about something like this. “Intimate relationships” don’t suddenly appear out of nowhere. They build up with time. Yes, if the OP was to find himself in some woman’s bed, he would be better off telling her that he’s still a virgin. But being embarrassed about it and worried about her reaction is pretty natural. If he was following this advice, he might never have any kind of relationship, because the more time pass, the more embarrassed he will be. At the beginning of a relationship, your partner is mostly a stranger, and being unwilling to admit to some shortfailing or another out of fear of the partner’s judgement is normal (often, for instance, people are unwilling to admit to having had _too many_ partners). If people didn’t have sex until they don’t feel anxious about their first time, everybody would die a virgin and the human race would go extinct. _Who_ wasn’t anxious the first time? ---
**Author:** ![RealityChuck](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/realitychuck/32/195_2.png) [@RealityChuck](https://boards.straightdope.com/u/RealityChuck)\ **Post date:** [December 15, 2014, 3:09pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/33 "2014-12-15T15:09:14Z")
> [@grude](#): > > 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. This. Further, I think any decent woman would find the fact you’re a virgin charming. ---
**Author:** ![monstro](https://avatars.discourse-cdn.com/v4/letter/m/ba9def/32.png) [@monstro](https://boards.straightdope.com/u/monstro)\ **Post date:** [December 15, 2014, 3:11pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/34 "2014-12-15T15:11:29Z")
> [@clairobscur](#): > > If people didn’t have sex until they don’t feel anxious about their first time anymore, everybody would die a virgin and the human race would go extinct. _Who_ wasn’t anxious the first time? > > “Intimate relationships” don’t suddenly appear out of nowhere. They build up with time. Yes, if the OP was to find himself in some woman’s bed, he would be better off telling her that he’s still a virgin. But being embarrassed about it and worried about her reaction is pretty natural. If he was following this advice, he might never have any kind of relationship, because the more time pass, the more embarrassed he will be. At the beginning of a relationship, your partner is mostly a stranger, and being unwilling to admit to some shortfailing or another out of fear of the partner’s judgement is normal (often, for instance, people are unwilling to admit to having had _too many_ partners). > > If people didn’t have sex until they don’t feel anxious about their first time, everybody would die a virgin and the human race would go extinct. _Who_ wasn’t anxious the first time? Hey, reread what I said. I didn’t say he shouldn’t feel embarrassed or nervous. It is 100% understandable why he would feel both. But if he’s too embarrassed to be honest about something like this, then he doesn’t trust his girlfriend all that much. You really should only have sex with someone you trust, correct? I’m not putting sex up on a pedastal. But this guy doesn’t strike me as someone who’s just looking to pop his cherry. If he was, he would have already done so. ---
**Author:** ![TheBuilding](https://avatars.discourse-cdn.com/v4/letter/t/aeb1de/32.png) [@TheBuilding](https://boards.straightdope.com/u/TheBuilding)\ **Post date:** [December 15, 2014, 3:23pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/35 "2014-12-15T15:23:06Z")
> [@Martian Bigfoot](#): > > Edit: Actually. come to think of it, I suspect that there might be a valley of derision and suspicion. It starts some time in high school and lasts for maybe a few years. So the good news is that you’re out of it. I know some adults who are as judgmental as high school students. ---
**Author:** ![TheBuilding](https://avatars.discourse-cdn.com/v4/letter/t/aeb1de/32.png) [@TheBuilding](https://boards.straightdope.com/u/TheBuilding)\ **Post date:** [December 15, 2014, 3:26pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/36 "2014-12-15T15:26:58Z")
> [@clairobscur](#): > > A lot of them, however will consider you not having had a relationship (not just not having had sex) at 27 as a big red flag. This. Even if they as monstro says not laugh at me they would still be suspicious. It’s for this reason that telling a potential girlfriend never entered the equation. ---
**Author:** ![monstro](https://avatars.discourse-cdn.com/v4/letter/m/ba9def/32.png) [@monstro](https://boards.straightdope.com/u/monstro)\ **Post date:** [December 15, 2014, 3:46pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/37 "2014-12-15T15:46:51Z")
> [@TheBuilding](#): > > This. Even if they as monstro says not laugh at me they would still be suspicious. It’s for this reason that telling a potential girlfriend never entered the equation. Would you really want to be with someone who’d laugh at you? Sure, your girlfriend may laugh. She may not laugh, but she may still think awful, horrible things about you. Guess what? If you’re terrible in bed, she will likely also think horrible, awful things about you. UNLESS you prepare her upfront. If it turns out that you’re horrible, at least she’ll know why. There are guys who’ve had tons of experience having sex, who don’t know they are actually quite bad at it, and would be surprised (and hurt) to hear the truth. Which is why their girlfriends say silent. Telling your girlfriend that you recognize this is a weakness of yours gives her permission to be completely honest with youu, so she can help you make the experience enjoyable for the BOTH of you. By being honest with her, you’re basically telling her you care about what she gets out of sex and that you don’t have your macho ego tied up in it. Seriously, these are very charming qualities. A lot more than how many ladies you’ve “scored”. Sex is stressful and anxiety-provoking for women as well. Consider that by telling her your secret, you remove some of the pressure on her too. ---
**Author:** ![puzzlegal](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/puzzlegal/32/3827_2.png) [@puzzlegal](https://boards.straightdope.com/u/puzzlegal)\ **Post date:** [December 15, 2014, 3:47pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/38 "2014-12-15T15:47:04Z")
> [@TheBuilding](#): > > This. Even if they as monstro says not laugh at me they would still be suspicious. It’s for this reason that telling a potential girlfriend never entered the equation. I don’t think I would bring that up on a first date with a potential girlfriend. I think it would be fine to tell an actual girlfriend with whom you were contemplating sex about your history (or lack there of.) Presumably, by then she knows you well enough to but be scared off just by that. The party that would make me nervous, as a woman, is the “never in a relationship” part, which you would already have moved through. Not the “don’t know the mechanics of sex” part. ---
**Author:** ![Sampiro](https://avatars.discourse-cdn.com/v4/letter/s/2acd7d/32.png) [@Sampiro](https://boards.straightdope.com/u/Sampiro)\ **Post date:** [December 15, 2014, 3:51pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/39 "2014-12-15T15:51:50Z")
> [@Shakes](#): > > Just so ya’ know, kissing ain’t gonna happen with a prostitute. Might be a straight thing, but… I’m a gay male and I haven’t officially used a prostitute, but I’ve been to gay strip clubs where the fully nude dancers definitely kissed on the mouth. (In fact, I wasn’t expecting it and it sent me running to the attended restroom to rinse with mouthwash as soon as the dance was over.) ---
**Author:** ![RTFirefly](https://avatars.discourse-cdn.com/v4/letter/r/c77e96/32.png) [@RTFirefly](https://boards.straightdope.com/u/RTFirefly)\ **Post date:** [December 15, 2014, 3:51pm UTC](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270/40 "2014-12-15T15:51:56Z")
> [@clairobscur](#): > > I don’t think virginity is non-existent in senior high school. The average age of first intercourse in the USA (assuming you’re American) is 17, so many still didn’t have sex when they leave high school. > > However 27 is way up in the extreme range. Some women won’t care about it. A lot of them, however will consider you not having had a relationship (not just not having had sex) at 27 as a big red flag. 27 is even further up in the ‘no experience even with kissing’ range. And that’s what I’d suggest the OP seek, um, professional help for, and not worry about the virginity bit. It really isn’t tough to figure out how to get Tab A into Slot B, even on your first time. If the OP is going to hire an escort, he should explain that he’s never kissed a woman, and that’s what he wants out of their ‘date’ - no sex, just some kissing lessons and a fully-clothed makeout session. This has the additional advantage, AFIACT, that paying a woman for a makeout session is perfectly legal, so he can ask her upfront whether that’s something she’s game for, and what she’d charge for that. [Previous page](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270.md?page=1) [Next page](https://boards.straightdope.com/t/should-a-27-year-old-virgin-lose-his-virginity-to-an-escort/707270.md?page=3)