Dear Wendy
Dear Wendy

“I’m Ashamed I Lost My Virginity to a Prostitute”

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I am a 21-year-old guy and up until earlier this year I was still a virgin. I get a good amount of attention from women when I do get out, but, without going into too much detail, I do not date a lot because of my crazy busy work/life circumstances. I was a late-bloomer and didn’t really start dating until this year, and I only got my first kiss last year at 20. I had a few chances to lose my virginity with different women I had been seeing, but, embarrassingly, nerves kept me from performing each time.

Now all of my friends have been sexually active for years and there’s always been jokes and pressure to get started, and they didn’t really understand my situation. I also work in a workplace — the military — that is the very definition of hyper-masculinity, where there is an expectation to be sexually-active and where I have experienced and witnessed others being put down for being sexually inexperienced.

Here’s the bad part: Recently, on a trip to Europe with friends, we made a stop in Amsterdam and, after a night of partying, alcohol, and a little bit of encouragement from my friends, I slept with one of the women in the red light district. I guess my thought process at the time was that I just wanted to experience sex and see first-hand what the whole fuss was all about. I had also been feeling bad about my past failures and really wanted to get the first one out of the way.

The whole experience, while the woman was friendly and nice and I tried my best to be respectful and polite, was underwhelming and left me feeling terrible. I feel so ashamed over what I have done. The act itself was so mechanical and hollow and devoid of any emotions. I often lie awake in my bed and wonder about what led the woman I slept with to enter that line of work. I know Amsterdam’s RLD is legal; however, I just feel horrible if I took advantage of her circumstances or something like that. I never thought I would be the type of person to pay for sex, and I feel terrible knowing how disappointed and disgusted some people in my life, like my sister and mother, would be with me if they knew. I feel like I let them down, but most of all I let myself down.

The sex was safe, a condom was used for everything, and I tested clean a few weeks after and will be tested again in a few months to ensure I am clean. I just don’t know how I am going to get back into dating after this. I feel like I am tainted or carrying this huge shame around with me and that, as soon as any woman I date asks about my sexual history or first time and finds out what I did, she will be gone.

How should I approach this in future relationships when the topic of sexual history comes up? I just can’t help but feel that this will be a deal-breaker for most women. I can’t justify it to myself, so I would be hopeless explaining it to a significant other. I am an extremely honest person and couldn’t lie. In the past, girls I was seeing never asked but this was always in casual relationships, and I feel that in a serious relationship this is bound to come up.

I think about this daily and it’s really bothering me. I feel like this one act has completely changed my life. — Ashamed of Sleeping with a Hooker

I replied to a similar question here, and I think my response applies to you as well:

Even good people pay for sex sometimes. You can care about people and still pay for the experience of having sex you may not be able to have otherwise. Trading cash for physical intimacy isn’t a symptom of being bad. You know what is? Treating people disrespectfully. Being unkind. Being a racist or a misogynist. Blaming others for your own low self-esteem. Being close-minded. Taking, taking, taking without ever giving back. Hurting people intentionally because you’re hurting yourself and you can’t stand anyone else being happy. And people who are all of these things — even people who are “bad”— are still just human like the rest of us, making mistakes and maybe even learning from them and growing from them.

We’re all on our own journeys, celebrating our own minor and major victories and battling our own demons or insecurities or general shit that gets us down. Most of us are doing the best we can, and some of us are even pretty good at hiding the ugly stuff, the hard stuff, the stuff that keeps us from being the best versions of ourselves we can be. But we all have that stuff. All of us. Every single one of us. So . . . stop being so hard on yourself. Stop beating yourself up for being human and having experiences in your past you aren’t 100% proud of. You are the sum of all of your experiences, not just isolated ones that represent a teeny tiny percentage of your entire history. You are the kindness you’ve shown others and the work you invested in reaching a goal and the moments you’ve fallen a little bit in love with someone you just met. You are the good days and the bad days and the weeks you’ve lost to being sick. You are the races you’ve won and the jobs you didn’t get and the exams you aced after too much or hardly any studying. You are all your first days of school and summer vacations and the dates you’ve had with someone you were trying to get to know. You are the sum of ALL your experiences, and you are under no obligation to share with potential partners any of the isolated experiences you feel uncomfortable with or ashamed of or that don’t effectively represent who you are now.

Since your specific question relates to how you lost your virginity and that’s something that sometimes comes up in relationships (and I do agree that some women would have a problem with the way you lost yours), I’d just come up with a vague response if you’re ever asked about the specifics of losing your virginity. Something like: “I lost it on vacation in a one-night stand and it wasn’t meaningful and I regret that part, but I also learned something about myself and how important it is that there’s emotional intimacy before enjoying physical intimacy with someone.” That isn’t a lie at all, and it highlights something of your character that would appeal to a lot of women. Clearly, you’re a sensitive, thoughtful man, and I hope you don’t let this one regret you have ruin your confidence and keep you from pursuing meaningful relationships.

Related: I’m curious as to how many people have asked or know the details of how each of their significant others lost his or her virginity. I sort of don’t think knowing these details about a partner is as common as you, LW, think it is. I’ve been with my husband for nine years and I never thought to ask how he lost his virginity, at least not that I remember (and, if I did ask or if he shared it, it must not have been very important to me since I clearly have no recollection). I know roughly how old he was, and I do know how many women he’s slept with — not because I asked but because we both volunteered our numbers once in one of those giddy conversations you have early in relationship when you’re so eager to really, really know each other — but beyond that, I just don’t care about his sexual history and I don’t think he cares about mine. After all, it has almost nothing to do with our life together (with the obvious exception of whatever experience we gained before we met and how we apply that experience to our, um, relations) and it certainly doesn’t define who we are. What about other people? Do you know how your partner lost his or her virginity? Do you care?


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.

65 comments… add one
  • Essie February 26, 2015, 9:19 am

    I’ve never asked, and no one I’ve dated has ever asked me. And I’m an old, and have been dating for 30 years. It wouldn’t occur to me to ask. General dating history is relevant, and of course people get a sense of that as they get to know a new partner.

    But the specific circumstances of how my partner ‘lost it’? Who cares?

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  • Laura Hope February 26, 2015, 9:23 am

    Your sexual history is nobody’s business unless you want it to be. I’ve been married a long time and I have no idea how my husband lost his virginity, nor does he have any idea how I lost mine. And frankly, I’d be shocked if he asked. (In fact, I don’t remember anyone ever asking me that).
    And just so you know, I suspect most people would choose a do-over for their first time if they could. It’s usually not something out of a romance novel.

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  • veritek33 February 26, 2015, 9:33 am

    The only partner I discussed losing virginity with was the man I lost my virginity to. He brought it up because, well, it became a topic of conversation that night. I think the only other man who I discussed it with was my most recent ex who just dropped into conversation that he was 17 and it was in a car…..not sure how that came up but I remember that convo. But he never asked me and the other men I’ve slept with never did either.

    I wouldn’t stress too much about future partners asking – it honestly didn’t occur to me to ask because I don’t really want to know.

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  • something random February 26, 2015, 9:38 am

    I know how my husband lost his simply because I was curious; I love listening to all of his different stories about his life growing up.

    I’m sorry this letter-writer regrets his first time but if it helps a lot of people have anti-climactic, awkward first times. While I don’t personally condone getting involved with prostitutes, what he did was legal and a pretty understandable temptation given his circumstances. It sounds like it was a real learning experience. I completely agree with Wendy that it isn’t necessary to disclose the complete details of one’s first time with any future partner unless one feels like doing so.

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    • MissDre February 26, 2015, 9:40 am

      Yeah, my first time was pretty lame too.

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  • MissDre February 26, 2015, 9:39 am

    I think it probably comes up more often with younger couples. I do remember talking about these things with guys I dated in my late teens, early 20’s. But honestly…. past the age of 25 it’s never come up.

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    • niki February 26, 2015, 9:44 am

      I think this is so true. I think there was so much more significance placed on sexual history when it was all new. At a certain age you just accept that everyone has their histories and that it isn’t that important.

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    • Addie Pray February 26, 2015, 12:44 pm

      Oh good point. I can’t think of ever having a conversation about it with anyone I’ve dated in the last 10 years.

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  • niki February 26, 2015, 9:42 am

    I know how old my husband was when he lost his virginity, but that’s it. He knows how old I was. And honestly that doesn’t even matter. I don’t need to know the dirty details of his sexual past, and he doesn’t need to know mine. Our sexual future is more important.

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    • Diablo February 26, 2015, 10:10 am

      “Our sexual future” is a really heroic sounding phrase, which I think i should start using in my marriage.

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  • Kate February 26, 2015, 9:49 am

    Agree with the advice. Re: Wendy’s question, it’s not something I care much about or feel like I need to know, but I do in fact know how my husband lost his and he knows how I lost mine. It’s just one of those things that came up in conversation somewhere along the way, but not important at all, just a minor piece of info in knowing each others’ stories.

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    • Kate February 26, 2015, 9:53 am

      Which is to say, it’s kind of likely that the topic would come up at some point but I think Wendy’s response is fine. It’s not a lie, and if he’s clean he’s not putting a future partner at any risk. I guess I WOULD want to know if my guy is someone who would solicit the services of sex workers, so I’m slightly torn, but if it was absolutely a one-time thing and you’re not going to do it again, I think Wendy’s suggestion is ok.

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  • its_rae February 26, 2015, 9:51 am

    I had never thought about it before but I do think age as MissDre pointed out affects whether the conversation comes up at all. Well for me anyway. When I dated in my early twenties, it was a frequent topic but not specific to how virginity was lost but rather the number of previous partners. Once I was divorced and began dating again in my early thirties, the conversation never came up really. Perhaps the age we were when we lost our virginity may have come up during idle conversations that couples have but the overall assumption was that previous sexual activity wasn’t as important as figuring out whether we work sexually or otherwise. My current partner and I had a brief conversation once about losing our virginity and the overall awkwardness of those first initial sexual experiences. And like Wendy I couldn’t even tell you how he lost his virginity, though I know we have spoken about it. I think in serious relationships you realize that those things don’t define who you are now and past sexual history has little to do with your current relationship (in most cases).

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  • Sunshine Brite February 26, 2015, 9:54 am

    I’ve might’ve asked once with a guy I was friends with and later FWB but other than that I’ve never asked and no one’s asked me. I’ve had people lose their V-card to me and not tell me until later which was weird but I didn’t tell the guy I had sex with until later so it evened out.

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  • tbrucemom February 26, 2015, 9:57 am

    I think the LW sounds like a good person and he’s being too hard on himself. I’m a mother and as long as my son was safe and respectful I wouldn’t think any less of him. It’s also legal in Amsterdam so no laws were even broken. I’d feel the same say about my husband. I have to say I did keep wondering while reading the letter if he is a religious person and that may have something to do with how he’s feeling. I’m by no means knocking religion, I’m a Christian myself, but his description of how he feels just reminded me of stories I heard from some Christian friends of mine when they lost their virginity (minus the prostitute part).

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    • something random February 26, 2015, 10:26 am

      I agree. I would be far more saddened to think of boys saddling themselves with harsh judgment and not liking themselves than to think of them engaging in a one-time consensual sex transaction. I hope he forgives himself and values what he learned from the experience.

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      • SpaceySteph February 26, 2015, 3:34 pm

        Well it seems like at least one of his main sticking points is whether it was a truly consensual sex transaction. I’m not very familiar with how the sex trade is in Amsterdam– my hope is that with it being legal, that comes with government regulations and less human trafficking, but that could be untrue.
        If you feel some need to atone, LW, how about supporting a domestic human trafficking organization– either with time or money, as your resources better allow? Don’t have to beat yourself up about it, but you can do something to make it better.

    • TheRascal February 26, 2015, 11:13 am

      I wonder the same thing about how religious he is. He is so ashamed and feels so guilty….these feelings in response to sex have to be developed somewhere.

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  • Ella_ February 26, 2015, 9:57 am

    I think Wendy’s advice is great — if the topic of losing your virginity comes up, framing your thoughts as how you felt about is a great way to share what you want. Nobody else is entitled to know, unless you want to share.

    For the other question, the only guy who knows the specifics is my ex-boyfriend, who was the first person I slept with. I can’t remember who mentioned it above, but general dating history is a lot more important to me than knowing specifics about having sex for the first time. I know my current boyfriend has slept with more people than I have, but beyond that, I don’t really need or want to know any more. I know that I’m the person he is with and wants to be with now, and that’s what actually matters to me.

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  • Diablo February 26, 2015, 10:09 am

    M and I know all the details of each other’s past, not blow by blow as it were, but in essence. Mine is fairly uncomplicated. I lost it at 20, and was with only a few women before her. I only ever had sex once with someone I really didn’t know as a friend first. The only judgment rendered by M regarding my lack of experience was “For a beginner, you’re pretty good at [that one certain thing I like to do].” I smiled and did it some more. M lost hers at 13, not entirely by choice. In those days it would still have been statutory rape because of her age, but the prevailing attitude would have been that she put herself in the situation. Before anyone flames me, this is not my attitude, but as any older DWers can attest, “date rape” as a concept had yet to be invented, and it was different times in a LOT of ways in the late 1970s. Between then and me, she got around a bit. My only judgment rendered on her was “For an experienced girl, you’re pretty shy and demure.” Her response was to smile and do something not shy and demure. I think if you are with a good person, these things will not matter. Anyone who takes you to task for your sexual history or lack thereof is kind of a douche, as long as there are no lingering infections that need to be discussed.

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  • Eve February 26, 2015, 10:19 am

    Regarding the guilt you’re feeling – Wendy’s response from the previous post is just brilliant! Absolutely everyone you know has done things they aren’t proud of, and this includes any girl you’ll be dating in the future as well. Don’t think you’re the only one who’s done something you consider a mistake, we are human beings and anyone with enough maturity will be understanding.
    I will give some balance here because I know 99% of the people will say that they wouldn’t even ask you about your sexual history anyway and even if someone does, it’s none of their business (which is true anyway, you don’t absolutely have to say anything even if it’s brought up or again, the template response Wendy gave is very, very good, and still true).
    I have stated here before that a partner’s sexual history can affect me in a negative way (and everyone disagreed with this statement but hey). Where I live the topic of virginity and sexual past actually seems to come up quite often, maybe because we are all young still (early 20s).
    I won’t generalise and tell you that definitely no one will care about this, because people are so different and have such different values and cultures and perceptions about things. What I will tell you is that there are so many different nuances to every story and although I don’t even know you, if someone explains this “mistake” he’s made the way you have done so in this letter, I won’t see him as a man who has lost his virginity to a prostitute in Amsterdam and that’s it (even if my moral values do generally put me off the idea of men paying for prostitutes, which they do). Instead, I will see an incredibly thoughtful, conscientious, sensitive person (I know that the last adjective someone in the military wants to hear about himself is “sensitive” but I promise I mean it in the best way possible, the type of sensitive that women are generally after in a real man, nothing soppy or mushy or non-masculine, promise!) who is trying to do the right thing as much as he can, has been under lots of pressure due to the environment he is in and has made a mistake which does not change the fact he is still this a good person (which I think you are from reading your letter and a decent woman who has got to know you in person should see more clearly). Not only this, but as Wendy suggested this “mistake” has made you realise something so valuable about sex and about the emotional part of it, you have learned something about yourself which is so important and believe me, many women will appreciate.
    If you don’t want to say anything about it, as the others have/will tell you, you don’t have to. But if you need to/ want to talk to a future partner about this, just be honest with her as you have been here in this anonymous forum, don’t be afraid to say your true worries and anxieties and regrets you’ve had. And I suggest if you do share this, make sure it’s after a few months of serious dating, give her time to get to know you for who you first.
    In my last relationship I shared something which I was very NOT proud of with my ex only after we had been dating for a while, mainly out of a sense of guilt. He was very, very understanding, he said he knew I am a good person at heart who means well to everyone and that everyone makes mistakes. He said I was also very brave to share this and he looked up to me after this.

    Give some more credit to any woman you’ll date in the future, you might be surprised how understanding people can be.

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  • SpaceySteph February 26, 2015, 10:21 am

    I know approximately how old my husband was when he lost his. And I know how many women he’s had sex with. I don’t really know any other details, and I’m good with that. I agree that Wendy’s suggested answer is probably plenty of info for most girls and you won’t get in a long conversation about it.

    However… my ex was my first, and I think because I was a virgin when we started dating, I asked him a lot more questions about his past sexual experiences and wanted more details… who she was, how he knew her, what it was like. As I got older, wiser, and more experienced myself, that info became less important.

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  • K February 26, 2015, 10:22 am

    I’ve known how pretty much all the guys I’ve dated (for more than a month or two) lost their virginities, including my current boyfriend, and they’ve usually known how I lost mine. It’s just something that comes up, and I’m someone who likes knowing about people’s pasts because it is a part of them. I don’t judge them in any way for it. Especially once you’re past a certain age, how your lost your virginity isn’t really a big deal at all.

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  • Ale February 26, 2015, 10:44 am

    I have asked and I have been asked. I´ve responded with the truth a couple of times, like with my current boyfriend. I asked him, simply out of curiosity and not as a way of shaming him. My bf, like the LW here, feels ashamed about things he did sexually in the past. I do not care about those things, and I´ve told him many times he shouldn´t be ashamed of them. Your sexual history and the way you develop yourself sexually should not be a concern to anybody else but you. If a woman you really care about asks you, you should tell her and she should not care about it. If she does or has a problem, then move on, she´s not worth it. There´s plenty of women out there who wont shame you on it.
    I dated a guy once who, after eight months of dating and having sex like bunnies, told me that he couldn´t live with the fact that he was the second guy on my list. He told me that he was going back to his ex, who was a virgin when they met and she “was really worth it”. Can you believe it? At the time I felt like crap, but eight years later I realize that no one, not absolutely one person has the right to make you feel bad about your sexual history. So, remember who you are, pull yourself together and don´t feel bad about this, this was a learning experience and you’ll get through it.

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  • mylaray February 26, 2015, 10:48 am

    I would want to know if someone slept with a sex worker, not because I care, but I’m really nosy about those things. I’ve always been surprised by the experiences of the men I’ve slept with (not in a bad way). I dated a guy for awhile who lost his virgnity later than you LW in another country with a prostitute. I was surprised he had been a virgin until then, and I thought it opened up interesting discussions about sex, stds, and consent. Not super similar but I was a stripper for a few years and I’m sure there are people out there who would care so sure, there have been times I’m a bit more sly about what I say. My husband and I probably overshare everything about our sex lives with each other and I’m glad I know so much honestly. I like knowing the masturbation habits, porn habits, sex toy use, and everything else of the people I’ve dated. I never would have guessed he lost his virginity at 25 and we’ve had interesting discussions about that too. I’ve pretty much discussed it with everyone but I don’t ask how many someone has slept with, though often we just volunteer that info at some point.

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  • booknerd February 26, 2015, 11:01 am

    I think I’ve known the sexual histories of most of my long term partners. Im interested in that aspect of their lives and I am honest about my experiences with sex. I think you should be honest about when you are in a serious relationship if it comes up. The guilt you feel is unwarranted, I think. It happened. There’s nothing you can do to go back and change it now. Worrying about it can’t change anything. But I’d be honest, because if I was your girlfriend and heard a coworker or friend ragging on you about the prostitute in Amsterdam, then I’d ask questions. And lying about that would make me wonder what else you were lying about.

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  • Red_Lady February 26, 2015, 11:02 am

    I’ve been with my husband for 7 years, and I have no idea how many women he’s slept with, or when he lost his virginity. He knows mine, but that’s just because he was my first, and I felt the need to tell him before (mostly just to justify why I was making him wait)

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  • othy February 26, 2015, 11:05 am

    My husband knows how I lost mine, but only because it was with him (and him with me). But, we were really young when we started dating (16 and 18), so we didn’t have time to build up much of a history.But, if we were to start dating now, it wouldn’t matter much.

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  • snoopy128 February 26, 2015, 11:05 am

    I’ve never known about virginity things with my ex’s. I don’t ask about the details. I don’t even know how old my current partner was when he lost his, but now I’m so curious to ask.
    I think Wendy gave great advice. I think you need to take this is a learning experience and don’t beat yourself up over it.

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  • RedroverRedrover February 26, 2015, 11:09 am

    I know how my husband lost his because he ended up in the hospital, and the story is pertinent to our sex life now. He doesn’t know how I lost mine, although I got engaged to the first guy I ever dated, and was with him for four years, so it’s pretty obvious that that’s the guy I lost it to.

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    • MsMisery February 26, 2015, 1:20 pm

      Is this like one of those “Sex Sent Me To The ER” stories from TLC? >_<

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      • RedroverRedrover February 26, 2015, 2:13 pm

        Well, poor guy, his foreskin wasn’t completely separated from the glans and he didn’t know. So when he tried to do it for the first time, penetration pulled it back and tore the skin connecting the foreskin. He still has discomfort with it which is why I know the story. Can you imagine? Your first time, and you end up in ER? Jeez.

      • mrmidtwenties February 26, 2015, 10:27 pm

        I’m cringing about the idea of that now. That must have been so traumatizing. I had a friend in highschool who snapped his hard on in half his first time and had to go to the ER.

  • kare February 26, 2015, 11:10 am

    I realize I’m in the minority, but I think past sex stories are entertaining. I don’t want to hear stories about the amazing sex my boyfriend used to have, but any awkward, bad, weird, etc story is entertaining to me. Virginity stories usually fall in that category. I’m also pretty open and will bring up awkward stories without a second thought. For instance one of my friends said something like “at least it wasn’t like the politician on sex and the city” and I replied “oh I’ve done that” without a second thought to how that’s not something most people share…eh, oh well.

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    • MsMisery February 26, 2015, 1:19 pm

      Wait so you slept with a mid-level politician, or someone asked if they could pee on you?!?

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      • kare February 26, 2015, 6:33 pm

        Someone who asked me to pee on them. Anyone else’s first love drop that bomb after six months of dating?

      • mrmidtwenties February 26, 2015, 10:30 pm

        I think past sex stories hilarious and entertaining, and have definitely swapped them with past partners and friends, but I think there was no mutual push to share beyond what was comfortable.

  • chief10 February 26, 2015, 11:13 am

    Ok LW time for a less “hyper masculine” opinion/perspective of things…first off i’m scratching my head on why your co-workers/buddies were so hardcore into you having sex? I get the military macho scenario but still, if my friends were all up in me like that I’d be wondering if they wanted to have sex with me. But that’s neither here nor there.

    Wendy gave you the perfect advice on how to explain your first time if/when it comes up and as other Wendy Crew have mentioned this topic tends to go away and become irrelevant around 25 or so. Don’t worry about it so much, you’re putting waaaaayyyyyy too much thought into it.

    Lots of people don’t reflect back to highly to their first sexual experience. Mine was when I was 18 with my gf at the time. We were up in my room, one thing led to another and I realized I had no condom. Totally unprepared. I went downstairs to see if my dad had any in his dresser (upon reflection why I thought my married dad would be using condoms in his late 40s with my mom of similar age is beyond me). I then had to leave, drive down to local gas station, buy some, head back and start over with my gf. I totally thought I had blown it and while she still wanted to after that is beyond me, I was nervous, couldn’t get the condom on. The first one was then unusable and she had to put the second one on. Still at this point she still wanted to, which still baffles me to this day. And when it finally happened, it was done and over with after a few minutes.

    Back in the day I too worried about explaining it to others, but I thought why do I have to. It’s important to me only. Looking back on it, it too was devoid of emotional ties and all the lovey dovey stuff society and books and movies tells us it should be. But it’s my story and I don’t have to share it with anyone. I choose to share it with you and the DW Crew to let you see that not all guys are in the Macho Bang Bang club. Make peace with your experience and give yourself a break. It’ll all be good.

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    • Addie Pray February 26, 2015, 12:36 pm

      Love, love, love your picture.

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      • Diablo February 26, 2015, 3:09 pm

        AP, give us a short list of things you WOULD NOT do for a cinnamon bun.

      • Addie Pray February 26, 2015, 3:34 pm

        Hmmm, I would not hurt a person, or a pet. But everything else is open for consideration.

      • Diablo February 27, 2015, 9:48 am

        Would you pet a person?

  • Lucy February 26, 2015, 11:39 am

    I’ve just realized I have no recollection of losing mine. I have no idea what that even means.

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    • MsMisery February 26, 2015, 1:16 pm

      Hopefully that you’ve learned to place absolutely zero societal or emotional meaning on virginity! Or else it was just totally short and vanilla.

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  • Guy Friday February 26, 2015, 11:50 am

    I’d echo everyone else’s supportive comments, and add this: speaking as someone who has represented a fair number of clients in court who have engaged in prostitution at some point / are engaging in it now, I can assure you that you are ABSOLUTELY not the problem with the sex trade that everyone talks about. You come off in this letter like you treated the woman you slept with with respect and care and didn’t demand anything dangerous or get violent, which — if you’re going to accept the premise that prostitution is acceptable — is exactly the way sex workers want their “johns” to act. So while I can accept and understand your guilt about having sex with a prostitute in the first place, I don’t think you should further burden yourself with the notion that you have somehow wronged her.

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  • Jane63 February 26, 2015, 12:08 pm

    LW, I think you are being way too hard on yourself. You got drunk & had perfectly legal safe sex. Just be glad you didn’t get drunk and get a tattoo of the word MOM over your heart;). Things could be far worse. Live, learn, and move on.

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  • muchachaenlaventana February 26, 2015, 12:11 pm

    I agree, you seem to have approached this situation with respect and the guilt you are feeling now is unwarranted. I will also say that someone who really loves you, will not care how you lost your virginity, or not in a way that they will judge you on it. I had a really traumatic experience with a person sexually and the few partners I have told, have all responded in the most compassionate and lovely ways. Something I feel such shame over, they have accepted and even cried over for me. Someone who loves you will respond in an appropriate way to something like this, if you tell them, if it even comes up. I agree this isn’t really something that gets discussed so much and I hate you are having these feelings about it.

    Re Wendy’s question- my boyfriend now is the only person I have known how he lost his virginity, besides my first boyfriend. IT came about really organically and I only know because it was in the context of him losing it later than normal we were talking about something. SO I know the general timeline he lost it and that he was in a serious relationship but that’s it. The topic of me losing my virginity, the age I was is about all he knows and due to the age he knows who it was with, as I have only had 3 serious boyfriends, but nothing more. For me that is a private and special memory, just like it is for him and some things just don’t need to be shared.

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  • Addie Pray February 26, 2015, 12:39 pm

    I love Wendy’s response to this letter. Especially the suggestion to say what you learned about yourself and how important it is that there’s emotional intimacy before enjoying physical intimacy with someone. And you may feel comfortable sharing your story at some point later on, with the right partner, so I wouldn’t rule out ever sharing – if you want to and feel comfortable sharing. But again you certainly aren’t obligated to.

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  • bostonpupgal February 26, 2015, 12:48 pm

    LW, I’d like to echo the support of the comments here. You seem to feel so lost and sad about this, and my heart breaks for you a little. Since you feel that this was a mistake, the best thing to do is accept that you made a mistake, that the memory for you may always be painful, but you deserve the chance to move on from it and make the world and yourself a little better as a result. If it will make you feel better, make a small donation to a women’s shelter, advocacy group for women who have been trafficed, or women’s scholarship fund. Say a prayer and send good vibes to the woman you encountered. Accept that going forward you will not repeat the mistake, and then try to forgive yourself.

    The others are right that you do not owe a partner a disclosure of how you lost your virginity. The only thing is, if being with a prostitute is a deal breaker for someone and they express that to you, then you need to tell them. I’ll be honest, a man being with a prostitute, even once, would be a deal breaker for me. Before we became an exclusive couple and became, uh, physical, my husband and I discussed what our deal breakers/boundaries were, and the expectation was that we were completely honest in our answers. I in no way mean that to be a judgement of you and the way you lost your virginity, you sound like a good person who many women would be very happy to be with, just that it’s a deal breaker for me personally and I would need and expect a straight answer when I asked a potential partner if he’s ever been with a prostitute.

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  • Richard February 26, 2015, 12:50 pm

    Read the letter a few back on the guy who jerked off 4 hours a day to porn, then tell us how ashamed you feel of your sexual pursuits. Look, you’re in your young 20s. Trust me, you have plenty more sexual experiences to get embarrassed over. I once got a blow job from an overweight mexican stripper in El Paso on my 21st birthday. Trust me pal, we all have skeletons. Paying for sex may be taboo in the U.S., but there’s a reason it’s legal in Amsterdam – it’s just, eh whatever. There’s nothing wrong with honing your skills by working with a professional. Shake it off and get back out there.

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    • Astronomer February 26, 2015, 2:56 pm

      Now that is a story!

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    • RedroverRedrover February 26, 2015, 3:01 pm

      “working with a professional” made me crack up!

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  • findingtheearth February 26, 2015, 1:02 pm

    I have talked about it more with my female friends than with any male. I don’t even remember the last time someone in my life asked me. After a certain age, people just stop talking about it. I agree completely with WWS.

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  • MsMisery February 26, 2015, 1:11 pm

    I don’t date (currently) either, but back when I did I don’t really recall the topic of virginity every coming up. Maybe as a “how old were you when” but certainly no one asked the precise circumstances. My bff of 20+ yrs probably knows more about it than anyone I’ve slept with. However, I can see how the military environment would make one’s past and present conquests a topic of discussion, esp if you’re deployed.
    In the “real world” you’re going to meet women with various opinions on sex work. Personally, the European attitudes towards sex AND the legality of prostitution take a lot of the anxiety out of the conversation for me. Anyway, anyone who grills you about your sexual history or gets completely up in arms after finding out about this (especially since you have a clean bill of health) is probably no one you want to spend time with.

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  • Copa February 26, 2015, 1:41 pm

    I’ve never asked this or been asked this. The only time my virginity ever came up was with the guy who I lost mine to because it was important to me that he know it was my first time. He then volunteered the bare bones details of his first time, which didn’t even amount to more than “I’ve been with one other girl before you, and she was just a friend at the time.” At best I’ve been curious about age it happened in past relationships, but would never ask for details. And would probably never even ask about this subject period (I’d let it come up organically or let the guy volunteer it), but that’s just me. That said, if it somehow comes up and you are flat out asked if you’ve ever solicited a sex worker, I think honesty is important. (I’ve never thought to ask a boyfriend this. Do people ask this? I’ve asked about any health issues I’d need to know about before intimacy but never once has it crossed my mind to ask about it prostitutes.)

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  • wobster109 February 26, 2015, 1:43 pm

    LW: Do you think women are some mysterious hive-mind or something? Why would your mother and sister feel anything about it? Why would your future dates feel anything about it? It doesn’t affect them. And yes, some people (men and women) will be bothered by your choices, but so what? There are always people who make a sport of judging others.

    Virginity is for olive oil.

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  • Bioluminscence February 26, 2015, 2:15 pm

    LW, I have a son about your age, and my heart goes out to you. Listen, as other commenters have said: Your sexual development and history are yours, and nobody’s elses. You may choose to talk about this or that at some point, but you don’t owe anyone an explanation, and you don’t need to and should not consider how your family would feel (eek! My dad would probably be grossed out by some of the stuff I’ve done, but…YUCK! I do not think about my dad when evaluating my sexual choices, OK? He has absolutely no say and I would think it was really gross if he did, somehow. Boundaries!). I had some wild times as a young’n, and really, if anybody tried to judge me for them, I’d tell them to step right off. They’ve made me who I am today, which is more thoughtful, wiser, more self-aware, more knowledgeable about what I like and don’t like sexually. Be easier on yourself.

    PS: Please, stop worrying about the woman you visited. Being a sex worker in a country where it’s regulated, like in the Netherlands, is a way different cup of tea than where it’s not. And you can’t know why she’s doing sex work, and shouldn’t assume that it’s because she’s “damaged” somehow. That’s kind of condescending, don’t you think?

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  • Sandy February 26, 2015, 3:29 pm

    I know how old my boyfriend was and that it took him “forever” to figure how to get the condom on and how many girls he was with before me. I only asked him how old he was and all the other info was freely offered. My boyfriend is my first so no question about how I lost my virginity but he did ask once how far I had gone before (this is a bit after we’ve already started sleeping together). No more details than that.

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  • kali February 26, 2015, 4:15 pm

    My partner lost his with me… He’s never asked about my first time but knows how old I was at the time. It’s not a big deal to either of us.

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  • lpants February 26, 2015, 6:06 pm

    I’m 25, and I’ve never had anyone ask me about how I lost my virginity (I would find it odd..) and I have never asked my SO of 3 years, or anyone else for that matter. I do know how old he was because he offered that information in another discussion, but I don’t think he has ever asked me how old I was.

    Overall, WWS. I’ve known guys who’ve visited prostitutes IRL and when I know them to be guys that are cool, sensitive, and basically good (which you seem to be, LW) it really doesn’t change my opinion of them.

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  • Essie February 26, 2015, 6:15 pm

    LW, I have the feeling there’s a religious component to your guilt feelings. If you’re approaching this from a Christian viewpoint….forgiveness is a core tenet of your faith, right? So forgive yourself. You made a mistake. And the best kind of mistake – the kind you learn from.
    You’re young, and mistakes made when you’re young feel so much worse. Just because you haven’t made many of them yet. Trust me, you’ll make many more. And if you let them eat you alive, as you are this one, you’ll do terrible harm to yourself. Just let it go – keep what you learned, but let the guilt go. God expects no one to be perfect.

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  • Portia February 26, 2015, 7:29 pm

    In my experience, like a lot of others here, people only ask how old you were when you lost it. That’s all I would ask, and I don’t think I asked all my partners that either. I had some offer up the info, but that was it. Actually, I can’t remember if it ever came up with my partner of 10 years. We do know some of each other’s embarrassing past sex stories, though those were freely offered up because we both love a good funny story…

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  • Lyra February 26, 2015, 9:22 pm

    I think everyone covered the topic of you losing your virginity pretty well.
    Here’s my perspective: (I hope NG is ok that I’m sharing this…) I’m engaged to a man who was in the Navy for 6 years. He came into the military never having had sex and he left the military the same way. He tells me stories now about how he saw these guys just…losing control of themselves, and sleeping with every girl who would sleep with them just to add a notch to their bedpost. He also tells me about the guys who were married or had a serious girlfriend at home, but then when they weren’t at their home port, those guys would purposely go out to sleep with prostitutes or they would go to the bar with the purpose of going home with another girl. WHILE their wife/girlfriend waited at home. My fiance was absolutely disgusted by this behavior, and because of that and other reasons, he never dated much — on purpose. Even with all these guys around him who I’m guessing gave him grief about it, he didn’t want to get caught up in that. He’s one of the most respectful guys I know, and that is a big part of why I love him so much. You sound similar with your level of respect. Trust me, girls love that.
    My point here is that even though you lost your virginity, it’s totally ok if you choose not to sleep with women just because you feel you have to. It’s ok to wait until you are with someone you love. It’s ok to not go home with a girl at the bar every night. It’s ok. It really is. Quite honestly, your personality sounds like it would attract respectable women, the kind of woman you WANT to be dating. Not to mention, someone like that wouldn’t care about how you lost your virginity. ALWAYS treat women respectfully — I hope you never lose that quality! 🙂

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  • fast eddie February 27, 2015, 9:38 am

    I lost my virginity to a prostitute in Greece when I was 20. My only regret is that it was way too fast. I’d have liked to linger into the night but when it’s just business that isn’t gonna happen. It never made any difference to my future partners, the subject never came up. Only very recently did I mention it to my wife and she couldn’t care less.

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  • jlyfsh February 27, 2015, 10:23 am

    It sounds like you really have sex built up in your head. The first time is not always rainbows and butterflies for everyone. Even if you do love the person. It can be awkward and leave you feeling underwhelmed. I would stop beating myself up about my inexperience and enjoy dating. And the next time you find yourself meeting a person you’re interested in having sex with, go for it. Don’t make a big deal about being inexperienced. Just enjoy sex, because it should be fun. Not so stressful and anxious.

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