Sexual Health
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24 year old male virgin: lose virginity to cougar?

So here is the situation: I am a 24 year old white male. I am tall, athletic/muscular, went to a good university and have a good job now. Overall I'd say I've done quite well in life and I've got my future sorted. There is however one thing that my life lacks: women. I didn't go on my first date until just a few months ago, got my first kiss there as well. And that's pretty much all I've done with a girl, kissing (not even really making out) and holding hands. The two girls I've dated (one of which lasted almost 2 months) both dumped me for the same reason: I lack confidence and experience and they didn't want to be the ones guiding me along, holding my hand as I learn the tricks of the trade. A lot of it was also due to my lack of knowledge of how to physically escalate. What this boils down to is that I need more experience and confidence with women in order to truly get a girlfriend (which is the end goal, not necessarily to screw around a lot, though I wouldn't say no to that either). I have been recommended one option by several sources and I am seriously considering it (whether I am able to materialize it is another matter, but lets assume I am for the sake of discussion): Find a more experienced woman, a "cougar" to show me the ropes a bit. Why? 1) Well firstly its every guy's fantasy to be with an attractive older woman but that's beside the point. 2) As I've been dumped because of my lack of experience so far, perhaps I can use her as training so that I would face less dumping in the future because of that. 3) Gain confidence and experience around a woman physically, know what to do in bed because assuming I am not an undercover sex god, the first few times will probably suck for the girl. I'd rather make the times that I am with a girl I really care for better. Counterpoints: Do I really want to lose my virginity to a woman I don't care about and will probably never see again? I don't know, I used to think of it being important who you had your first time with but I just don't care that much any more after years and years of absolutely no female action just pass me by. Sure, it would be nice if the first time was with a special girl but its not that big of a deal for me. Questions: 1) Has anyone used this approach, had their first time with a cougar? And if so, was it "helpful"? 2) Has losing your virginity given you more confidence around girls? 3) What do you think of losing your virginity to an experienced woman?
2 1

Most Helpful Guys

  • well for starters I think its great you have your life on track at such a young age and that will be very attractive to a lot of different women over the next few years when they start looking for a partner. I too lack confidence and fit pretty much the same description as you but I'm a bit younger (almost 19). I think what you need to do (this helps me as well) is take a step back and look at yourself, even just look above at how you describe yourself; Athletic, muscular, life sorted out, good education, good job, People would kill to be in your position man! you have all the right in the world to be confident about yourself you're a catch! now I know its not as easy as just looking at that kind of stuff, a lot of it is in your head and its hard to get it out and women can really kill your confidence. I think this whole losing your virginity thing could give you a confidence boost but I think it could also kill it. Your first time could be horrible and end up ruining any confidence you had and make you feel bad about yourself, the chances that it makes you more confident is probably on the lower side. I think it would do you good to wait it out and find a girl you care about deeply and lose it to her, if its a girlfriend then chances are your connection will be deeper emotionally and she will support you and help you out along the way and it can be a great bonding experience for both of you. You strike me as the kind of guy who has good values, morals and I think you should stick to that when it comes to women. Sure you've had a few girls who weren't supportive or understanding, but that doesn't mean all will be like that and at your age is when people are getting more mature about relationships. That just my opinion its really all down to what you want, do you just want to lose your virginity and hope this experience gives you some sort of confidence or would you rather wait and share that bond with someone special? I think lots of girls would really value that you waited for that right person. You don't NEED more experience to get a girlfriend, I think you need to look at it differently. Everyone at some point went into a relationship or some sort of learning curve where they didn't know how to do certain things and that's what you're going through now! so just try to enjoy this learning period and keep your mind open and hopes up! everyone goes through it man and I think you'll be happier if you wait and do this all with a future girlfriend of sorts. Hope this helps, I know I repeated myself a lot but I just really wanted to get my point across :P you may regret just "losing it", you can always lose it but never get it back. Good luck with whatever you chose :)!

  • did you ever drink before you were 21? if so, how did it feel when you went to drink at age 21? sex is over hyped. making love is under hyped. I'm guessing that the escalation that you refer to is going from first to second base? I'm not real sure what second is, but third and home I know. when you are kissing these girls, do you not get aroused? at least mentally? if you do, then you will be like a kid seeing the presents under the Christmas tree. (can't wait to unwrap them) most guys when they are starting out, try to go from first to home. being a teen, this is usually a no-no. being an adult, it kinda depends. with adults, there's a bunch of fetishes and what not to deal with as well. the cougar idea is probably seen as more legitimite than going to a hooker. what are you thinking of when you are kissing these women?

    • Sorry, not American so the 21 limit doesn't apply to me. Also, I never really cared for alcohol.

    • you felt it was more important to say you're not American and you don't like alcohol? not being American, the baseball analogy doesn't work I guess.

Most Helpful Girl

  • Heyy :) I am not a cougar lol but I would like to talk to you more about this... I think I could help you out. If you want to talk either message me on here or add me on kik messenger: danielle...d

    Hope to hear from you :)

    • Hi. Already found a girlfriend (my age) and did the deed so this question no longer applies. Thanks though!

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What Girls & Guys Said

2 5

  • You need to figure this out for yourself. From all I've read here of late, an older woman who's not 1) tangled up in losing her own virginity and 2) is very inexperienced sounds like a good idea but it's up to you.

  • go for it its better than dying a virgin

    • i disagree.

    • Virginity is kind of meaningless in today's standards and he is abound to get good sex . He probably knows that it is stupid to get attached,and doesn't really care about the morality issue that much because of his age. A lot of loosers on this site can't get laid and whine about their incompetence , he can grow and learn from this experience and see if sex is worth all of the hype

  • My first time with when I was about 23. She was about 33. All I did was ask her to give me the full experience of sex for the first time. She was extremely open to it. She even embraced my pantyhose and high heel fetish. Best sex ever. I wish we did it more often before she went back to her husband.

  • No

  • i'd go for it if I were you

  • tl;dr

    But do you really just wanna throw it away like this? It will just ruin it for you. First of all: Your first time's memory will always be some "experienced woman" not the woman you loved. Second of all: She starts with using all her skill. What if you get a virgin next time who doesn't know a thing? Think again, and then think again - and guess what, after that: think again...

    I was 27 at my first time, just so, to let you know that there's no pressure up.

    • No pressure? At 24 I am already way overdue, I want to start enjoying life like everybody else is and that includes having sex. Does it necessarily have to start with an older woman? Don't know, that's why I made this thread.

    • Who decided that you're overdue? The only pressure on you is the pressure you put on yourself.

  • YES. This should (and will) work for you. There is no better thing in life than a sexy cougar around you, believe me. But make sure she is not too old. I personally like under 35.

    As soon as you lose your virginity, you will realize, right at that moment, that you are not the same person anymore. Be it your girlfriend, a hired pro, one night stand or even your wife. Because VIRGINITY is something special.

    If you really want to remove that VIRGIN label and be with someone more of your choice, go for it. These women have a lot to tell you.

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