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Should I lose my virginity to an older woman?
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I'm a 27 year old virgin. A 45 year old woman said she would love to teach me all about sex. She enjoys sleeping with younger men and she doesn't mind that I am a virgin.

The problem is I always wanted my first time to be with another virgin. I was hoping I'd meet one virgin girl and we'd date for awhile, fall in love, have sex, and be together. I've never been able to get a girlfriend all my life. It feels like I am saving myself for someone that will never exist.

I can finally get laid and she'd like to regularly have sex with me a few times a week. I feel like this is a golden opportunity but it goes against my morals and my dream of meeting one nice person to settle down with.

What should I do? Remain a virgin for another X amount of years or have sex with a very good looking older woman?
No save yourself for another virgin.
>The problem is I always wanted my first time to be with another virgin.

You should have abandoned that fantasy years ago, my man.
Flip a coin.

What's the side you were hoping it'd land on?

If it goes against what you truly want, don't.

Honestly I think you're putting relationships, virginity, and women on a pedestal, but that's your prerogative.

I'm the dude who posted this in another thread >>16821431

generally im against these types of scenarios but IF YOU FIND THE OLDER WOMAN ATTRACTIVE, then i say have sex with her.

you are 27. there arent many virgins left. if a woman is a virgin at 27 its generally because she is not desirable or nice in any way. women just dont 'save themselves' for that long.
Stupidest question of the year.

At 27 I'd give up dreaming about virgins. shes the right age to be an excellent fuck and the body is probably still OK if she's looked after herself.

Honestly I feel like I am putting it on a pedestal too. The problem is if I do this now, what happens if I do meet a girl and she is a virgin? I will have to tell her I lost mine to a 45 year old woman who only wanted casual sex. Even if she's not a virgin there's no positive way to explain this to a partner without me seeming like a desperate loser.

I know plenty of hot religious woman that are virgins. They are also crazy, so yeah..

so they dont meet the other qualifier OP and I mentioned, that they are nice or otherwise desirable.


you cant trust a crazy person to be honest about their virginity especially if


religious people are literally the only people left in the world who need to lie about their virginity. if a hot woman makes it to 27 and claims to be a virgin, its cuz they dont want to be shunned. sure a rare scenario here and there, but yeah.
let me get this right: a cougar wants to "break your virginity" and you are still wondering what to do?

>tap that ass. she doesnt want your life story she just wants a screw

Even if I accept that I'll never be with another virgin, there is still the moral dilemma of having casual sex with someone I'm only acquaintances with and not even dating. I would probably be okay with meeting a non-virgin girl, dating her for awhile, and then having sex if we have feelings for each other.

This is purely casual sex with no romantic attachment whatsoever and it makes me feel guilty. We were going to get a hotel last week but I cancelled on her and told her why. She said it's okay and she understands but we're still talking. She's not pressuring me at all she's actually quite understanding. She tells me whenever I am ready to let her know and we can do it. She's so polite and nice and probably would be the perfect person to teach me about sex but I struggle with the fact that she's not my girlfriend and there's no romantic feelings.

then dont do it.

Yeah don't do it, you don't seem comfortable with just having mechanical sex.
If there is no attraction don't do it desu.

Then again I'm the type of faggot to keep moral above anything in my life. The world might see it as a missed opportunity but you will die a happy man if you live up to your morals.
>what happens if I do meet a girl and she is a virgin?
Highly unlikely with sex culture nowadays.
You're almost a wizard, harry.
You have some error that you haven't had a desire to fix so that would become a reality. Girl virgins don't mind not being with a non virgin anyway so save your glass ego.
There is nothing special about losing your virginity. It's just your first time, when you're really bad at it. Go with the teacher, and she will educate you so that you don't fuck like an uneducated monkey.
Let me emphasize

Copy pasta:

>*shrug* just live your life how you want to, and don't let fear of shame rule your life.

>I was abstinent until 24. I met a girl, fell in love for the first time, kissed for the first time, and got my heart broken for the first time. After that I just said fuck it and literally the first girl I went on a date with, just had sex with. In the span of a year I had sex with three women, and made out with maybe forty or fifty different girls (and a few guys). Then I took a break and just calmed down. I met my girlfriend about a year ago. Fairly glad I went and experimented because it helped teach me who I was. Tbh part of me would have been ok experimenting more but the vast majority is more than content).

>Unlike me, She had a much more traditional history where she's only really ever slept or kissed with the couple long term boyfriends she's had, but wasn't really phased by my weird past.

>Live your life, it's yours, no one elses.

On her part, she actually just said my history was really interesting and she respected that I had the conviction to wait that long, that I followed through the way I did, and that I had the restraint afterwards.

To be honest, my fist time was a total throw away and absolutely cringe worthy. It wasn't that I preformed badly.... but for me it was just a rebound one night(s) stand. I even straight up told her that before we began, she said she was looking for the same thing... but was followed was drunken texts and late night sobbing voice-mails...

That shit kind of ripped me apart inside with guilt, but I took it as a learning experience. I dated a shit ton in the year or two that followed, and i learned how to not confuse sex with emotional connection, how to fine tune the charm to avoid leading girls on (like with the first one), and how not to confuse other girls attraction for me, with my attraction to them (because being considered attractive when you'd never had that most of your life, can be addicting).
Same anon here as >>16821565

OK. I accept you have a moral dilemma but frankly you seem to have a very immature or sheltered view of relationships.

Sex should not be confused with morals. Morals govern how one interacts with society but shouldn't govern us to an extent we deprive ourselves of life experiences. Experiences which then contribute to our ability to be a well balanced member of society who can employ empathy and understanding because of those experiences.

Your present attitude doesn't bode well for any relationship even if you found another virgin. I foresee trouble as this kind of moral dilemma extends into other areas of any relationship because idealised concepts are nearly always unrealistic and thus unachievable by a partner.

Look, tell the 45 year old your fears and let her guide you. I think this may be the best thing to ever happen to you, indeed life changing as your self imposed shackles of idealism are unlocked.

TL;dr... Just go fuck her for gods sake. It's going to be great and afterwards you'll wonder what you were thinking.

I understand what you are saying. I would have no problem sleeping with a girl who wasn't a virgin as long as we loved each other. It wouldn't the perfect most fairy tail way for my first time but that would be okay. If there was mutual love and respect I would be happy and content.

I guess it's more about wanting to do it with someone who I love than do it with someone who I have no emotional attachment to.

I think what bothers me more is not that I haven't had sex but that I haven't had a meaningful relationship with a member of the opposite sex. It's pathetic to go through 27 years of existence without ever having a girlfriend. Having casual sex with this woman won't change that. I'll still be 27 years and single, the only difference is I'll have had sex.

Will that make me feel any better? I don't know. I feel like I am being an idiot to not take this opportunity, but I worry about regretting it if I do.
Does she mean sex or coffee?

Like I said when I first replied (and that you agreed on), you're putting things on pedestals.

I'm the guy who lost his virginity at 24, and I believed a lot of the same things you did. But half of it was also fear, and me holding myself back. The part of why I reacted the way I did when I got my heart broken. Because of once in my life, I took a chance, and put myself 100% out there to someone, and even if I failed, it felt liberating. That's why moving forward afterwards I learned to stop limiting myself threw myself into the dating world. I didn't actually meet my first girlfriend (who I'm with now) until I was 26, but in that time, I learned a lot about who I was.

Am I saying that losing your virginity and having sex will teach you a shit ton about who you are? No.

But holding yourself back because you want to hold true to an ideology that's apparently making you miserable is pretty nonsensical.

If you want to do it, do it. If you don't want to, that's fine. But don't let fear control you.
May I ask how your relationship started and has continued?

I am constantly anxious about the fact that I've never had a romantic relationship with anyone and am now 25. I'm not bad with people, have a lot of friends and can be social when it's needed, I just have never had a girlfriend. I don't how relationships form and how to "act" while in one. Would you mind going into some detail?
There's a chance she's fucking with you, pun intended.

Other than that go nuts. Your ideal scenario is a product of sexual inactivity, and not only is it unrealistic, especially for your age, but also stopping you from actively seeking normal sexual relationships.

Seriously you miss a great oppurtunity there.
My first time was also with a virgin and it was horrible.
We both fucked it up.
She wanted it to be perfect but how should that work without any expirience?
It hurted her, even after licking her princes for a good while.
My condom was too small so we did it without, not being enough we had to stop.
As dumb as she was she wanted it after i was drunk and stoned as fuck, we where at a friends house at a party, she said to me lets go sleep and i really thought wed go sleep... dumb too.
after going up i had to go down again to ask for fuckin towles, and she didnt wanted to turn on the light or even suck my dick, but i had to lick her.... seriously it was traumatic to me and i wish it would have never happened.
On the second run we did great, i planned it this time but her and my first time was horrible and ill never be able to forget that....

1 year later, me being 21, i ve met a 34 year old women called Sarah, she just talked straight to me and we banged at the first time we met already, i told her that i really have less expirience and she said that she will teach me everything i need to know... and mate seriously it wass fucking wonderfull... she told me gently what to do, what feels great and what not, she just took care of me in a great way, so i wouldnt feel bad for my little knowledge and for her a way to take the lead and enjoy.... ill nbever forget that she did me a really nice Bacon sandwich after the first time we slept together... it was the heaven.... untill today we have sex 2 to 4 times a month, without a relationship, but it seems like we will get together.... yeah, so i would really recommend you to take the opputunity before youll regret it
What's worse, regret or wondering what could have been?

Uhh... Sure?

We met on OKCupid. I sent her a message complimenting her on how well written her page and with a book recommend, she replied back complimenting me on using a "$50 SAT word". I replied back with some dumb joke. She asked if I wanted to meet. I asked if Friday at this cafe was good, she agreed. Three messages total.

We met, we chatted, we ended up getting dinner and drinks when the cafe closed. She actually ended up saying it was the best date she'd been on, and asked if it was cool to see me again. I agreed.

Second date i took her to an arboretum, to a pool hall, then dinner and drinks afterwards.We ended up holding hands.(glacially slow progress to what I was used to, but that first date I remember thinking "Oh hey, I actually like this girl. I kind of don't want to rush things at all")

Third date we went to the mall, then grabbed some more dinner and drinks, then the beach, and we shared our first kiss. Then back to her place... I asked if she wanted to be a couple, she said yes, and pretty much one thing lead to another and we ended up having non-stop sex for 4 days (I called in sick lol).

The last day we were together that week, a friend called (my oldest friend actually) and invited me to crash at his and his GF's. I said, hold a sec, and turned to her and asked if she wanted to come with. So two weeks later, we took a thousand mile trip together.

Things have always just kind of taken a natural progression. I've never really thought about it and just went with the flow. If I had, a lot of things probably wouldn't have worked (I think the only reason she agreed to that trip was it was just so obvious I put absolutely zero thought in to it lol--looking back that was a ridiculously impulsive decision).

Before that though, like I said, I did a SHIT TON of dating. I was pretty used to dates, knew exactly how to get girls to loosen up and shake the jitters, how to keep conversations going, and was pretty confident in myself.
Sorry if it was a weird question, I just have zero clues as to how to form a relationship so getting some kind of framework would really help, thanks for indulging me. It seems the key lies in your last sentence. I don't have the dating experience nor do I have the confidence at this point. You went so long being a virgin and then finally getting a girflriend, how do you manage to seem so well composed, and for a better word, normal? Going that long in life without intimacy is not the norm yet you seem to be perfectly ok. I feel like I'm normal but my life experiences seem to point otherwise. There's something I'm missing and I don't know what.
>27 year old virgin
How the fuck does this even happen? You have to either be ugly as fuck or basically captain autismo.

I spent my whole life basically ignoring women for the most part and still lost my virginity at 18 when I settled on a girl I wanted to fuck.

I'm decent looking. I just don't talk to girls at all. I go to school, I go to work, I come home and study/play video games. My only hobby that puts me outside is biking but I do that alone on my state's forestry preserves.

I have no opportunity to meet a female with my current lifestyle and even if I did I wouldn't have the confidence to approach one.

Yeah, man. Go for it.

Straight talk, she's a woman who wants to have sexual intercourse with you and the fact that you can't make your mind up shows that you're considering it.

It sounds like it'll be a friends with benefits kind of thing so you'll get good at sex without commitments which will theoretically boost your confidence with women and might prove to be a catalyst in your sexual endeavours which would combat your low confidence with women.

This is more beneficial than detrimental in your case, OP.
At 27 you are more likely to get a visit from the publisher's clearing house than meet another virgin willing to sleep with you.
Beggars can't be choosers OP
I guess I could tell you my story? It'll be kind of long though

The short version: I just chose to be optimistic and treat everything like a learning experience.

The long: Honestly, I was depressed for a nearly a decade. Pretty much as soon as I hit puberty, my hormones went wacky as heck, and I started going through massive bouts of depression.

On top of that I was a massively shy kid. Like I hated and was terrified of going to restaurants because it meant I'd have to talk to a stranger to order my food. That's why the few times my family could get me to come out a restaurant, I'd tell my dad or mom what I wanted instead.

So my senior year of highschool, I decided fuck it, and decided to try to change. It started out small, like just speaking up in class, trying to maintain eye contact while speaking to people, fixing my posture, etc. When I got to college I got a new haircut, new wardrobe, and continued the trend of upward mobility by going out and introducing myself to classmates. Then speaking out in class conversations. Then going to parties and introducing myself to random strangers. I kept pushing myself to do more and more. After a few years, I started going to resturant bars after work, just sitting down and ordering a meal and drink, and started making conversations with total strangers just to pass time.

(Post 1 of 3)
All though this, the depression was still kicking in though. One particularly nasty bout hit me when I was 20, maybe 21. Everything in my life felt like it was going amazing for the first time in a long time. I was excelling at school, leading two study groups, consistently working, and was starting to become closer and closer friends with a classmate (I think if everything continued the way it was going, she probably would have been my first girlfriend) but then out of nowhere, I suddenly felt crushed. My world felt like it was collapsing around me, and I had no idea why. I stopped going to school except to take exams, I stopped going to work, I stopped answering my phone and ignoring texts and calls from even friends.

After that I went through a pretty dark part of my life where I was sick of it, and decided one way or the other, I was going to stop being depressed, and I gave myself an ultimatum and set a date.

When that date passed, I had made my decision, and I stuck to it and kept trying to push forward.

I'd forced myself to stop letting myself indulge in depression, but life instead felt grey, and empty, and part of me felt like even the depths of darkness was better than the nothing I was feeling. But I pushed on, because I made that promise.

Then one year at a friends birthday party, I met a girl. I met a girl, and I talked to her, and I heard her life's story, and it inspired me. She'd been through so, so much worse than I ever had, and she survived, and she was an amazingly bright person. Meeting her, I felt like if she could do it, so could I. And from that day forward I had a new spring in my step.

(post 2 of 3)

I didn't actually end up meeting her for another 7 or so months. She ended up being a friends new roomate, and I bumped in to her at the housewarming party. From that day on, we started hanging out more and more. And the more time I spent with her, the more illuminated my world felt. I already admired her, but that slowly started to become more and more. I think it was about a year and a few months after I first met her, but eventually I realized, I was falling totally in love with her.

It was a realization that shocked and kind of unnerved me because while I had already slowly starting to come to the realization that, I'm kind of attractive both physically and mentally (through a lot of small experiences at college), I was still in no way comfortable with the concept of dating, let alone dating someone I felt taht strongly about.

But I gathered my courage one night, and I told her how I felt. I put myself 100% out to someone in a way I never had before. And it resulted in a moment I still remember vividly to this day. From the confused way she looked around, to the uncharacteristically shy smile, to the tingling I felt for an hour after our kiss--my first kiss. But, it wasn't to last. I was crushed.

But I realized feeling crushed felt MUCH MUCH better than never having said anything and living in the regret of never knowing. That is the only kind of pain that can never be learned from and never fades. The gooey, slimy, and heavy weight just slowly builds up thicker and thicker and weighs down your heart and eats away at your soul.

I took a chance, and I failed, but I felt liberated.

(Post 3 of 4)
From that moment on I had no fear, no regrets, and no shame. I flung myself head first in to the dating world, and just like I did when I started introducing myself to socializing, I started seeing everything in the dating world, failures and successes, as an experience to be learned from. Slowly I improved myself to become the kind of person I wanted to be, and slowly I became more and more confident that I always WAS the person that I wanted to be, and all I had done was merely polished what was there.

Take things at your own pace, and don't feel like you have to go by everyone else's. True confidence is being able to say that you lived your own life, and that you traveled your own path. It's having failures and successes be a part of you in your bones so that you can always say that you know what life is first hand, and that no one can take that from you.

Good luck.

(post 4 of 4)

Thank you. There's only so much that phrase can express, but I say it with full sincerity.

We seem to be fairly similar. I came to my own realization only in the past year but I've achieved a lot more than I ever have in my past ten years of living. I'm taking baby steps, slowly crawling out of my depression. I don't know if you've ever had weight issues but that's what kickstarted my current endeavors into improving myself and how I feel about myself, it's also more than likely a major contributor to my issues. I've lost 100 pounds in the past year, along with opening up my social life, getting interested in other hobbies aside from videogames, and having my first sexual experiences (not all the way, but more than I've ever done for sure). It's hard not to compare myself to the people around me, and I realize I am behind, but I have to get comfortable with the fact that I might not be where everyone else is, but progress is progress and I am succeeding as long as I'm moving forward. I probably need another year before I really feel comfortable with myself, but a lot can happen in a year :)

Nah, i'm lucky enough to have an insane metabolism and have always had martial arts deeply rooted in my life.

Anyway, you're going down the right path though, and you're right, you just need to take one step at a time.

If I'm honest, there definitely was a period where I was dating where I started to wonder if I was cursed because every time it felt like I was getting close to a girl, something drastic would happen to kill any chance.

Like... that first girl... at the same time I went through my depressive collapse, she had some crazy shit go down in her family, which overwhelmed her life as well...

One girl I met literally the weekend she graduated and was moving back home (half a thousand miles away), and her best friend had been trying to hook us up for over a year but we were both just too stubborn to go along with it til that night. We kicked ourselves the next morning, and agreed to never let her know we'd hooked up (lest she gloat lol)

A couple of girls, a family member straight up died shortly after we started dating (one in lost her favorite 9yo student, run over by a car right in front of her, one lost her younger sister).

Heck, my girlfriend, a months before we started dating her division got shut down and she got laid off, and shortly after we started dating, she lost her great uncle (who basically raised her and was her father figure) On our second date I remember her mentioning being worried about him going to the hospital. He died two weeks later of stage 4 cancer.

All you can do is just keep doing what you do and have faith that you're moving forward. Even if you can't have faith in the world, have faith in the experiences you've built up to better yourself.
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