Sexual Relationships
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Should I lose my virginity to a cougar?

So, I'm a virgin in my early twenties. I use online dating and I stumbled upon an older woman (46 years old) who was quite attractive and I matched with her. We texted for a while and eventually the conversation became sexual. I kept flirting with her and eventually she gave me her number. We kept flirting and, I can't lie, she said the right stuff to make me horny. We had really sexual texts and she said she wanted to have drama free fun at her house next weekend. So, the horny side of me says, yes, spend all night with her and fulfill your milf fantasy, but, the romantic side of me says, save your virginity for someone special. I'm not sure what to do. Should I lose my virginity to a random cougar?

The other part of this situation is that I'm going to see my crush from college in about 2 weeks after not seeing her since the pandemic started. I planned on revealing my feelings for her when I see her, because I actually think I love her. I missed her so much after not seeing her and I've felt feelings for her that I've never felt for a woman before. I feel like it would be bad to lose my virginity to some random cougar right before I reveal my feelings to my college crush. It just seems cheap and I feel like I should save myself for my crush, even though she could reject me. Yet, I'm lusty, and a night with a hot cougar sounds very appetizing, especially since she acted like she wanted a friends with benefits relationship, so this could lead to a lot of fun, there's so much temptation. But, if my crush accepts my feelings, then I won't need anyone else. What should I do?
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Most Helpful Guys

  • Wow bro. You have a unique situation here. I can tell you i gave up my virginity at 23 years to a 36 yr old woman. At that time i was masturbating like 3 times a night and could not handle the hormones. I met this woman online in a chat and we hit off a good friendship. One night i told her what i was doing online and that masturbation just wasn't working for me anymore. She actually told me i was a nice guy and that she would help me. I being a virgin thought i was seeing things on the screen then thought it was a miracle. Unfortunately i didn't have the option of a girl my age that might want to exchange our virginity or might want my virginity. A friend or girlfriend. I think you are given two choices here. A part of me would have preferred to give my virginity to a younger girl around my age or to another virgin. But i am also grateful and lucky that the woman i experienced my sexuality with was not a streetwalker or worse. Lol she also turned out to be clean and had her tubes tied. So condoms were not required. Lol i suggest you sit yourself down and really decide what you want. If you really want your crush i suggest you try for her first. It sounds like that this milf will be there for you if the crush does not come through. But if you are lucky and you and your cruch get together and can have a relationship then go for it. I wish you luck bro and happy nights ahead. 😎👍

    • Exactly, but he needs to find a way to keep the cougar as a backup plan.

    • @Twalli most definitely. Lol

  • The cougar might be able to show you the ropes and give you some fantastic orgasms. Have a ton of condoms handy and go for it. It does not mean you won't like your crush and maybe you will even miss her more! Is your crush a virgin also?

    • My crush is not a virgin. We talked about it once and she knows I'm a virgin though, we were close friends.

Most Helpful Girls

  • Don’t lose your v card. Save it for your crush. Does your v card hold some importance to you?

    • I'm starting to think that's what I'll do. I do value my virginity and I feel it should be given to someone I care about.

    • I agree 👍

  • The cougar said she wants someone drama free. Maybe she should keep looking.

    • I know right. 😅😂

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What Girls & Guys Said

0 13

  • It's much better to lose your virginity to a girlfriend you love.

  • I know the sexy cougar sounds appetizing.. But, if you have a crush you wanna get a chance with I don't think, havin a temp situation with a horny mature woman is goin to not complicate things.. So yeah save it for yo crush if y'all get together..

  • sounds tempting

  • Go ahead, An older woman has far more experience and you can be the beneficiary of that

  • save the v card

  • That's all up to you my man

  • Go for it, it might help you avoid being simpy and desperate with your crush, which would probably happen with me lol,,,
    It would certainly help with self-confidence imho,,,

  • Tell the older woman you'd like to meet once in person before actually having sex. Therefore you don't burn any bridges. If your crush reciprocates, you give it to her. If she's not interested you still get the cougar.

    • FYI, I lost mine to my girlfriend at 27.5, so it's possible to wait. Will you update us with how your situation went?

    • I'll probably try to do something like that. I'll update you dependent on what happens. This story isn't over. 😅

    • Wishing you luck with your crush.

  • Sure, there's nothing else going on, so why not

  • I Vote yes, it's an excellent and safe way to get started

    • How is it safe? I mean like she could have an STD. I don't know her that well.

    • use a condom if you are unsure

  • Any hole will do

  • Do it u want regret it

  • Speaking as a guy in his 40's if i had it to do over again i would NEVER pass up a chance for sex with an attractive woman. Also you're not looking at rhe orher side of it. You"re not a little girl. Your first time really isn't special. And you're probably going to suck anyhow. Why not get all the practice you can now.

    • If his crush is also a virgin she won't know how bad at ot he is until they're both better and then it won't matter. My girlfriend and I started together and we both realize now the first 4 times (we did it 4 times that day) were pretty subpar. They were pretty good when we did thrm though.

    • @Twalli who said his "crush" is a virgin.

    • My "crush" isn't a virgin. I was close friends with her in college and I found that out, she also knows I'm a virgin. We shared that with each other at one point.

    • Show All

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