losing virginity at mid 30s

LegacyUser

I am thinking to lose my virginity to a friend of mine whom I have known for a year. We fooled around for a few times at the start, but I was scared and also I wanted a relationship and he did not so we did not go the whole way. He knew I was a virgin and he did not pressure me. The fooling around stopped because we started dating other people and all that. We still keep contact (I initiate most of the time). I moved on and dated some other guys but have not yet met anyone I really like to that point that I want to sleep with.

Now, I am a bit sick of being a virgin and he is the only man I would like to lose my virginity to because I trust him and feel safe with him. I know the risk I am going to take, e.g. being rejected, being emotionally invested in a man who doesn't have the same feeling... I am thinking to have a chat with him about the idea and I would tell him that after the hook up, we would part and disappear forever in each other's life. I am leaving the country for a month anyway and after that, there will be a lot of changes in my life so I am quite sure I can get myself very occupied. Indeed, I am not very emotionally attached to him now because I have very busy life.

I fancy him a lot and I am sure he is sexually attracted to me too. He might be worried about my feelings so not wanna do that. Or he might not agree with it. Anyway, how can I word it to make him welcome the idea?

And what I should be careful of? Surely I know about condoms.

Just a side note, I don't mind losing him as a friend, because I don't think we are purely friends anyway. I would want to cut all the contact and I was trying to until he contacted me St. Patrick's Day trying to initiate some flirt with me.

Any input would be appreciated.

LegacyUser

OP here.
Before people ask, I just want to say that I am not doing so because I want to get him to a relationship. I know I can not. My another birthday is approaching and that it's why I think it's time for me to experience sex before I am too old that virginity would be a hurdle in my future relationships. I would rather experience sex with someone I sincerely like than any random men. Anyway I am sexually attracted to him. And I know I can trust him. The cutting contact thing is I really want to move on after the experience. I know I can't move on if I keep him in my life. I would rather 'use' him and lose him.

LegacyUser

Go for it. I was an old virgin as well - I was nearly 30. I lost mine to a man I hardly knew because I just wanted to have it gone. It goes without saying that I'd rather have lost my virginity to a loving boyfriend. The only regret is that it would have been nicer to have done with someone I knew better.

Seeing as you're emigrating soon, I don't see any problem in asking this man. You're going to be drifting out of his life when you leave and he knows this too. If he says no, you only have a month to go before you leave. If he says yes, you can get get this monkey off your back and perhaps get in some practice. Tone down your language when you ask him though. You are of course using him but you don't have to phrase it in such mechanical terms.

He knows you're a virgin which is great. He also knows you're emigrating soon so no danger of you coming after him looking for a relationship. Why not tell him that you're up for a bit of fun before you leave and you're not after anything serious? Leave it at that.

As for the act itself, just make sure that he takes it easy and doesn't hurt you. Don't expect it to be particularly wonderful either. It does get better with time. Leave him to put on the condom and take the lead. He's the one whose done it before and he'll know the positions.

ihsb

I understand that you like this man but I am one to believe that you should lose it to someone that you could end up loving. This means relationship. This means that you would feel safe and looked after and the rest. Also the sexual attraction would be there.

Just because another birthday is coming doesn't make you think you should just throw it away. You have kept it for this long, I wouldn't want you to regret loosing it to someone that you didn't have deeper feelings for.

If you decide that it is going to be with him then you deffo have to communicate with him. You have to make sure that you tell him what you want. But be prepared, what you want before and after sex might be different. It can and does change things.

midnight_train

Hi OP,

TBH, I wouldn't do it.

I was a virgin until I was 26. I waited until I was with someone I really loved, and I'm glad I did.

My brother was a virgin until he was 31. He waited for the same reasons. It's not actually that weird.

I've another good friend who's still a virgin at 36.

You know the first time is generally not great, but it does get better if you do it lots! So I would never want to just do it with someone I didn't care about once, just to do it, and then never again. Where's the enjoyment in that?

It's like waiting for the Dublin Bus, especially before they got those digitized grid things. Are you going to keep waiting for the bus (which WILL come eventually, at some point) or just waste the money on a taxi? You'll get to the same destination at the end. I say save your money and wait for the bus ;-)

I promise you, there are other nice, normal 30-somethings out there who've never had sex. It doesn't make you a weirdo.

LegacyUser

OP here.

Just to clarify I am not leaving the country for good. I am travelling for a month then will be back to a new position and will be travelling more this coming year and exploring the world. So yea, the guy might be hesitated that I would come back and haunt him! Not sure how to reassure him about this. And at this moment I am quite sure I can cut the contact if he does not contact me.

Thanks about the concern about my feelings after the experience. I have thought about that and because I haven't had experience before I really dont know how I would feel after. Haven't thought about the 'emptiness' feeling. That's a good point. But I guess it's a chapter in life and I would suck it up if I feel so bad after.

I have a very strong desire to do it with him. And I am not thinking of a just a once off thing, but a good few times to learn from it and experience it. Then we cut each other off.

About the friendship thing, I guess both of us know we are not just friends and even if I do not use him, I would cut him off my life anyway and he knew that I was distancing myself like what he did to me. BTW, both of us are single so my proposal would not hurt any other people.

I am sure I will meet a man to form a loving relationship but I don't know when and I don't want to wait until I am 40 and to co-star with Steve Carell! I feel my virginity is a baggage at this point because it clouds me to see man woman relationship in a way that's too simple and too fairy tale.

But I really don't know how to word my idea to him that he welcomes the idea without worrying too much about my feelings and me haunting him afterwards!

snafuk35

andthat wrote: »

I am thinking to lose my virginity to a friend of mine whom I have known for a year. We fooled around for a few times at the start, but I was scared and also I wanted a relationship and he did not so we did not go the whole way. He knew I was a virgin and he did not pressure me. The fooling around stopped because we started dating other people and all that. We still keep contact (I initiate most of the time). I moved on and dated some other guys but have not yet met anyone I really like to that point that I want to sleep with.

Now, I am a bit sick of being a virgin and he is the only man I would like to lose my virginity to because I trust him and feel safe with him. I know the risk I am going to take, e.g. being rejected, being emotionally invested in a man who doesn't have the same feeling... I am thinking to have a chat with him about the idea and I would tell him that after the hook up, we would part and disappear forever in each other's life. I am leaving the country for a month anyway and after that, there will be a lot of changes in my life so I am quite sure I can get myself very occupied. Indeed, I am not very emotionally attached to him now because I have very busy life.

I fancy him a lot and I am sure he is sexually attracted to me too. He might be worried about my feelings so not wanna do that. Or he might not agree with it. Anyway, how can I word it to make him welcome the idea?

And what I should be careful of? Surely I know about condoms.

Just a side note, I don't mind losing him as a friend, because I don't think we are purely friends anyway. I would want to cut all the contact and I was trying to until he contacted me St. Patrick's Day trying to initiate some flirt with me.

Any input would be appreciated.

So you just want a one-night stand? Just tell him to come over for sex and just do it.

ihsb

andthat wrote: »

I have a very strong desire to do it with him. And I am not thinking of a just a once off thing, but a good few times to learn from it and experience it. Then we cut each other off.

I mean all the respect in the world here. But you have not had sex before. You might be a girl that does not care about the person she is doing it with and can switch off. But you might not be. I, for example, have loved everyone I have had sex with. So I don't believe that just cutting him off afterwards will be able to happen the way that you hope. It might go that smoothly but there is a 50/50 chance that you will be hurt.

Also you talk a lot about trying to put his mind at ease, trying to make you see and convince him that you don't want more off him. Honestly? This is your virginity here. This is YOUR big deal. Don't see it as baggage.

If you were meant to do it with this guy, he should be the one reassuring you. He should be the one making sure that you are ok with the situation. He should be the one worried about you. This would mean that you would be in a relationship with someone you love.

CBFi

You seem to have it all thought out so I'd prob say go for it! Everyones different but I think people make a very big deal out of losing your virginity and you realise after its gone that it's really not such a big deal. Perhaps you may find it easier to relax and connect with guys once you're not a virgin because it's not hanging over you?

Then again, others have a point- it may not work as straight forward as you like but then again, there are worse ways to lose your virginity than with a friend (not too good a friend who you're attracted to)!

LegacyUser

andthat wrote: »

I am sure I will meet a man to form a loving relationship but I don't know when and I don't want to wait until I am 40 and to co-star with Steve Carell! I feel my virginity is a baggage at this point because it clouds me to see man woman relationship in a way that's too simple and too fairy tale.

Hi OP,

I would also say go for it. I lost my virginity quite late in comparison to other people, and it definitely does become a sort of baggage. It was a huge relief to get it over with. I lost mine to a guy I was dating - I didn't love him but I definitely liked him a lot and it could have been a lot worse. The line that you wrote above really stood out for me - when you're a virgin, sex becomes blown out of proportion into the biggest, most important thing in the world and it seems like everyone else is doing it except you.... but losing your virginity does not have to be the biggest deal in the world. It's just sex, at the end of the day - something that you forget when you're not having any!

Of course, it would be ideal to lose it to someone who you're in love with, but despite everyone's best intentions, you might not meet that person for another year or two. You have the opportunity to practice with someone you like and someone you're attracted to. I say go for it.

I'd say it to him in person though, rather than on email or whatever - invite him around to yours for a drink and tell him that you have a proposal for him. At the end of the day, that's what it is! If he says no, that's his loss. Good luck. And enjoy!

Dubhlinner

You'd be surprised how powerful sex can be for evoking (or re-evoking) emotional feelings for someone.

I'm not saying don't do it, as I completely understand your reasoning and logic for choosing him, just something to bear in mind

LegacyUser

If you are sure about the possibility of losing your friendship with this man and he is happy to help you with your plan, I would say go for it.

I was in my mid thirties the first time I had sex. At that stage it was niggling me that I was still a virgin. In the end I just had a one night stand with a man I know socially, not a friend of mine but we have mutual friends so I felt I could trust him. We only bump into each other a few times a year so I felt it would be perfect. I didn't tell him as I was too proud to admit I was still a virgin at my age! He probably figured it out but never said anything. The sex was pretty awful but I have no regrets whatsoever. It was such a relief to get it over with.

Might have been nice to be with someone I actually loved for the first time but personally the one night stand thing worked for me.

And I am now in a long term relationship with a lovely man and enjoying sex very much!!

Best of luck with your plan to open a new chapter in your life. Enjoy!