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Should I ask my friend to help me lose my virginity?

Tagged as: Friends, Sex, Virginity<< Previous question   Next question >>
Question - (26 May 2008) 17 Answers - (Newest, 13 November 2008)
A male age 41-50, anonymous writes:

I'll be turning 32 in a few days. I am still a virgin in just about every imaginable sense (I've never even french-kissed). This is something I am supremely self-conscious about. I also have an anxiety problem which tends to leave me more fearful than the average person. I tried to go and see a prostitute about this time last year, but that just didn't work at all...I was so stressed by the time I got to see her, I couldn't perform at all.

Anyways, with my birthday coming up, which always makes me think of this, I want to try again.

There's a certain platonic female friend of mine, someone I do trust a bit. I've been considering just sitting down with her, telling her where I'm at with this, and asking her if she would consider helping me to get some experience by sleeping with me. I don't know if this is a good idea or not...I really don't want to risk hurting our friendship, but this task has to be someone I can trust enough (a very short list of people).

So, yeah, should I:

A: Do nothing, and continue being a virgin and hating myself.

B: Ask my friend to help me, risking her saying 'Hell No' and never speaking to me again.

View related questions: prostitute, still a virgin

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A female reader, dearkelja United States +, writes (13 November 2008):

dearkelja agony auntI think her self esteem suffered after the break up and she felt "good" that she was in a "relationship." Some people just can't stand to be alone. To me what you had did not meet the definition of a relationship. I think she may have used you. I mentioned before that women can't just have sex (well I can't), we need to feel an attraction an connection to the person. It is possible she was still going through too many emotions from the break up and you made her feel worthy.

I think she took advantage of you being so kind. I hope you meet a woman with whom you can have that special connection and attraction. The first time is special whether at 40 or 18. Make it count with someone you care about.

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A reader, anonymous, writes (13 November 2008):

This is verified as being by the original poster of the question

I don't think it was like that (and I'd like to understand what happened...I'd appreciate your thoughts). She got dumped by the other guy, which was a surprise to her. Two days later, she sort of declared herself to be with me (which I was thrilled about, of course). After that, it was all weird. She'd be all flirty when she was asking for stuff, but whenever I tried to make a move, she cooled right off. But she insisted she was my girlfriend. I don't understand. If she'd accepted a kiss, or let me hold her hand, even once, I wouldn't have broken up with her.

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A female reader, natasia United Kingdom +, writes (12 November 2008):

natasia agony auntReally sorry ... that was an unfortunate experience. But I can't see how it means you are useless at reading people ... it simply means she was a bit mixed up. She wanted you - that's why her 'relationship' ended so quickly. But then she witheld sex. Or maybe you didn't offer it? Maybe she was shy about it. Just because one has had sex, doesn't mean to say one isn't shy about it sometimes.

It's hard to judge what exactly happened, because, for example, I guess she didn't just say 'do all this stuff for me and buy me a computer and expect nothing from me' ... you must have had something to do with it ... and she probably thought you were happy to indulge and look after her, and was waiting for you also to have sex with her. Trust me. I'm a woman.

Main point to take away from this: she is an individual; you didn't do anything wrong; it was just bad luck.

So you live to fight another day. Don't you?

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A reader, anonymous, writes (12 November 2008):

This is verified as being by the original poster of the question

I dunno if anyone is even still here, but here's an update:

I decided to go with the advice of one of the posters here, and ask her in the context of finding someone else. We talked about it a couple times, about how afraid I am and how I felt. Shortly after I initially talked to her about this, she started dating a guy, and I was going to put all this aside, but she didn't. Not long at all after this, she came to me and told me she'd like to sleep with me, but not while she was in a relationship. I thought her relationship was doing fine and that this amounted to 'first Tuesday after never', so I didn't think much of it, but a week later they had broken up. Very shortly after that (less than 48 hours), we ended up in what she called a relationship. This relationship mainly consisted of me doing things for her. Even though we had talked about sex, as soon as we started going out, that was completely off the menu. There wasn't even any kissing or cuddling or anything like that. This went on for about three weeks. During that time, she had me clean and rearrange her house, move her furniture, buy her a new computer and some other things. By the end, I could see what was happening (although not why...she was a good friend before all this, someone I really trusted) and I ended it.

Now, I'm 100 times as crazy as I was before, between feeling like I was so close but so far away, and just feeling hurt about being used. This experience has reinforced to me that I don't have the slightest understanding of people or relationships, and it's definitely left me feeling leery about mentioning how vulnerable I am to this kind of manipulation to any of my female friends. I don't know what I should do next, but I know this was a mistake.

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A female reader, FreedomFinder United States +, writes (2 August 2008):

I personally think you should not have sex with your friend,let alone ask them. I had a friend once who kinda did the same thing,but she was in high school and was never kissed. She asked a guy friend what was is like and he kissed her. they kinda had this friends with benifits thing going on, and after wards she felt used and confused. so I say no! also it makes you out to be some kinda loser...which I hope you aren't.

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A male reader, anonymous, writes (24 June 2008):

I have a female friend who was in a similar position to you, she was 29 and still a virgin. It had got to the point where she had zero confidence around guys and the whole virgin thing was really screwing her up. I'd known for years she was a virgin and she was able to talk to me quite openly about it.

As she got older, I'd notice she tended to clam up more whenever the subject of guys cropped up, especially when there was a few of us in a group hanging out. She started making excuses for not being able to hang out with us, became quite introverted for a while.

I used to try fixing her up with guys but she always found something wrong with him, anything just to avoid going on a date. I used to try to get her to see that losing her virginity wasn't as big a deal as she had now made it inside her head. The first time wasn't going to be her ONLY time, it was just the first time. Find a guy, do it, get it over with and move on with your life. I even offered my "services" a couple of time but she laughed it off.

In the end I decided to take matters into my own hands. I persuaded her to join me on a vacation in Vegas. Our second night there, I made sure she had plenty to drink, just to help her to relax and once back in her room at the hotel, I tried it on with her, I didn't push it too far but we fooled around for a while. Next morning she did that mock horror thing, "I can't believe you did that!!" but that night same again, a few drinks, back to her room and this time we went all the way. We did it a few more times that week and by the time we came home, she was like a different person, more confident, more sociable.

Our friendship turned a little sour afterwards as she became a little too attached to me, started thinking we were now officially a couple even though I kept explaining to her, that I was only helping her out, I just wanted to be her friend, not a boyfriend. She used to phone me all the time, follow me to work, harass any girl that might have showed an interest in me but that only lasted a few months and we get along better now.

She gets along with guys a lot better these days, usually seeing a new one every week and sometimes when she's between guys she asks me to help her out which I don't mind doing because she's become really good at it but it makes it really awkward with my current girlfriend, so I feel a little bad afterwards, but then she has been my friend for most of my life now and that's what true friends do, they're always there for you when you need them.

So my advice to you is, you should ask your friend, and her reply will tell you if she's a true friend or not.

Failing that, just pay for it, as long as you use protection, you've got nothing to worry about. Use the internet to find a girl that's highly recommended and hand over your cash. Believe me, afterwards you'll be wondering why you just didn't do that sooner! Life's too short, just do it and move on with your life.

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A male reader, anonymous, writes (23 June 2008):

I know what its like. I'm 22 and a virgin. I just asked my female friend to "help me". I risked it but stayed positive.

I came here looking for answers to this question to see if I was doing the right thing. She said she would think about it.

Give her time to think about it man. I am.

Good luck to both of us.

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A reader, anonymous, writes (13 June 2008):

thats a very interesting question. but also a very good one. if u trust ur friend and she is a person u think u can come to about anything, then i think u should. if u like ur friend and u think she might like u then u should definitly tell her. it would be great if u could lose ur virginty to someone u were in a realtionship with. and dont ever use a prostitute do u want a disease. and y would u want to have sex with a stranger. it wouldnt be special and it probally would be awkard considering ur a virgin. they might even make fun of u. (i wouldnt of course but they might!) so yes ask ur friend if u think she will understand and but if u think she wont. wait till ur in a relationship with someone u love. and if u dont want to then ask ur friend

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A female reader, natasia United Kingdom +, writes (26 May 2008):

natasia agony auntps sorry - just saw your second post. OK: so you only want sex to be part of the human race. Well, approach it with an open mind: you mind find out why people fall so madly in love and end up in monogamous relationships ... whilst being v commonplace, sex is also a pretty powerful thing. Hope you find that out soon!

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A female reader, natasia United Kingdom +, writes (26 May 2008):

natasia agony auntAsk your friend. There is an option C: she says 'Hell no' but still continues to be your friend ; )

I don't agree with those who say it's ok to be 32 and a virgin. You're right. You want to join the rest of the human race. Don't beat yourself up about how it happened this way, but yes, you're right to be taking action, I think. There are some things in life that don't happen unless you make them.

Do you have panic attacks in a sexual situation? If so, I really feel for you. I have had them (badly) in the past, but not with sex - but if I imagine having them in that situation, well, that really is unlucky. You know why? Because sex usually makes you feel so much better, and relaxes you, and takes you somewhere else, so your stupid brain (talking about mine here!!) just switches off and gives you a rest for a while.

I'm SURE you can do this, and can end up having sex as something that is an oasis for you, rather than seeming nemesis! There will be those who say you must find the love of your life before you have sex, but blimey, that might take you the next 10 years!! There's something to be said for trying to beat this phobia, and then being in a better and more open state for finding a life partner. I think you will just feel better walking down the street once you've had sex. I think that's what you think, too - and you're right.

Here's my example. I did something seemingly reckless and foolish, too. A bit like when you're contemplating losing yr virginity, everyone tells you it must be with the right person - well, of course, when it comes to having a baby, the sensible and desirable thing is also that it should be with the right person. I had a baby with the wrong person (baby now 2 mths old). It was a totally reckless act, and I am dealing with a fair bit of emotional pain as a result - BUT, and this is a big but, I don't regret it in any way, and I feel a zillion times better when i walk down the street - i feel part of the human race again. (and my daughter is amazing and i will make sure she is as loved and looked after as anyone can be) My point is: sometimes we know within ourselves that it is time to grab something, because otherwise our lives will waste away with longing and loneliness. I think you should go for it with the friend, because if she really is a friend, she'll understand. And even if she doesn't want to, get her on your side to find someone else.

Unless, of course, in the meantime you meet the love of your life. It is possible, but then again I just saw a giant pig fly across my room ... don't trust to luck: take your fate in your own hands! And remember: it's only sex. It truly isn't a big deal: it is the most natural thing we can do. It is, on one level, pretty much all we're here for (according to our bodies), so no wonder you feel you're missing out. Just, well, do it. Good luck!

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A male reader, anonymous, writes (26 May 2008):

Tell your female friend the situation in the context of asking if she can set you up with someone shoe knows or something. Tell her that she's the only female you feel like you can even talk or ask about this stuff, but don't directly hit upon the suggestion that SHE get busy with you.

If she's actually willing to do the deed herself, then this will probably get the ball rolling.

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A female reader, Emilysanswers United Kingdom +, writes (26 May 2008):

If you are not interested in relationships but just want sex then I suggest finding a nice local prostitute and trying again. Find a woman who works for herself as she is more likely to form a connections with you and be nice about it rather than just wanting it over with so she can go and buy drugs.

Either that or just get drunk and hit the bars. Just make sure you use a condom.

You are going to have to get over your anxiety or put up with it.

It is highly unlikely that your female friend will want to "help you" and will probably get freaked out if you suggest it.

Good Luck!! xx

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A male reader, anonymous, writes (26 May 2008):

first of all: Who cares what other people think. Don't do anything for the sake of what others will do or say about you. Your life if yours.

that said: i understand wholeheartedly about your anxiety regarding women. its not necessarily best that you engage in sexual relationsships and have them fail - it happens to the best of us - and carry worse feelings around. many men who experiment with sex in high school end up regretting in some way.

I will say: for your own sake: lose the "virgin" stigmata. whatever you have to do: do it. I would sit down with your platonic freind and of course say something like :' i really value our freindship more than anything..etc" ease into it without saying it straight out: see if she gets the drift without saying it; "test the waters" befire coming straght out with it.

if that doesnt work: its vegas road trip time: or one of those brothels. just wear a condom; find a hooker that does GFE (girl freind effect) save your pennies, it may cost a few bucks but you really have to do this. Mainly for your confidence in finding a regular girlfreind down the road: because confidence is really important as women react to it.

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A male reader, sammy296 United Kingdom +, writes (26 May 2008):

sammy296 agony auntdont ask her. if u hate urself at the moment then you dont want to risk you and ur friends relationship.

what i suggest is getting out there. go on a dating website or something. dont be self conscious about never french kissing as your date will never know that, untill it gets to that moment then tell them. if they are right for you then they will accept this and be unhindered by it.

Hope this helps:)

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A reader, anonymous, writes (26 May 2008):

This is verified as being by the original poster of the question

My friend is single. I am not too sure how she sees sex. And, as for what I hope to accomplish...I'm not capable of (nor terribly interested in) an intimate emotional relationship, which means I will never have a girlfriend. This is a fact of my life that I have accepted (from the emotional point of view) that doesn't bother me so much...it's impossible for this to change. Its not like that with physical intimacy. I am very very afraid of all this, but I know I can make it through this time. Once I have, then I won't have to blush or go away when The 40 Year Old Virgin comes on...I won't have to shift uncomfortably at work when the other guys are talking about sex and I am completely clueless. I would really like to be able to lie there convincingly...I'm sick of being laughed at, belittled, or whatever.

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A male reader, LazyGuy Netherlands +, writes (26 May 2008):

LazyGuy agony auntYou are going to put her into a very difficult position. Is she at least single and the type to see sex as something you do with someone you are not romantically interested in?

Even if she broke you in, then what? You would still be the same person, you are not magically going to find women beating down your door just because you got laid once.

I would suggest you examine the cause of you being unable to find anyone and try to fix that first. Experience is the least of your worries.

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A female reader, dearkelja United States +, writes (26 May 2008):

dearkelja agony auntI would not risk losing your friend by asking her. Women and men categorize sex differently, most of us anyway. Many women (and men too) can't just have sex for the sake of giving someone the experience they need. I also think that your first time should be special. Years down the road from time to time you will draw on the 1st time with fondness. I am afraid if you just give yourself without the proper feelings that you will be ashamed of your first time...and you will likely lose a friend in the process.

Why do you need to hate yourself for being a virgin? I actually think it's lovely and I hope you find someone who you care deeply about to share this first experience with. You will not regret it this special woman will help you.

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