A
male
age
22-25,
*loneinlife
writes:I will be 20 very soon and am still a virgin. I have tried to date probably more than a hundred women and have always been rejected. I have contemplated visiting an escort but don't want to lose my dignity doing so.Out of a whim I posted an ad on a website saying I need someone to help me lose my virginity. I said I didn't want to pay for the sex, just a casual hook up. I said I don't mind unattarctive or older women. I didn't expect a reply but 3 weeks later I received a message from someone claiming to be a 30 year old woman who wants to have sexual intercourse with me.Initially I thought it was a scam. Like an sextortion scam. I was seriously expecting a guy and the other end but I was surprised to hear a woman's voice. Curiosity got out of hand and I decided to meet up with her for lunch.I was really surprised when I met her in person. She is a tall and elegant woman with striking features and long wavy reddish blond hair. I noticed that she looked a bit older than her actual age. She said she is 30 but I would have guessed 35. However despite her age she is very beautiful. She actually reminds me of the actress Rebecca Ferguson. She was wearing a sleeveless gray business dress with a fine herring bone pattern. Very formal looking and expensive attire. She looked like a lawyer or banker to me. Not glamorous or posh but important and powerful. And very sexy at the same time.I am still worried that I was walking into a scam. I asked her why she was doing this. She said she had recently divorced her husband of 5 years and has been doing casual hookups for a while and very recently she discovered that she gets most sexually turned on whenever she gives herself to a male virgin. She said she gets aroused having the knowledge that she will forever be imprinted in his memory as the very first person he had sex with and she gets to teach him and mould him sexually for life. She didn't give me her name because she said she is a high ranking director of an international corporation and wanted to remain anonymous. I guess she didn't trust me either. Well I am still not sure if a could trust her. However, she seems like a nice person, very sweet and polite to me in speech yet gently authoritative in manner, a bit like the actress Cate Blanchett.I haven't given her my name since she didn't give me hers. I just told her I am a student in uni. I declined to have sex after our lunch. I said I wanted to to date her a bit and get to know her more, to get a girlfriend experience before having sex. She was ok with that.I truth I am hesitant and wanted to get your advice first.She seems honest but I can't be sure. Many scams nowadays. She said we can have sex at her house or at mine, entirely up to me. I obviously can't bring her home as I live in a share house with my uni friends. But I am worried if we go to her place she might have hidden cameras in her bedroom which she can use to blackmail me later. She lives in a town an hour away. She said she drove to the city to meet me because she said she prefers to hookup with men she is less likely to bump into in the future.What should I do? She seems honest and sincere. She also seems to be attracted to me during our "date". Very flirty. She touched me a lot and said she was pleasantly surprised that I am cuter than she expected and more attractive than the other virgins she has slept with. She also said I was also the most shy and soft spoken of the mentioned virgins.I asked her for another "date" this Friday. Again She will drive to meet me in the city. I am not sure if I want to have sex with her yet. She says we won't have just one sexual encounter but she will remain with me for a while and teach me until I "graduate" sexually. But she gets to sleep with other guys as well and I must not become possessive. So we will be like friends with benefits.I think I am in a unique situation. Not sure what to do. Help.
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divorce, escort, flirt, friend with benefits, get a girlfriend, shy, still a virgin Reply to this Question
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Fancy yourself as an agony aunt? Add your answer to this question! A
reader, anonymous, writes (1 February 2019): I think the question here is - why are you so hesitant? Get to the bottom of that and you have your answer.Are you just throwing yourself in before you are ready? Do you want to sleep with a woman or have you put off the idea of sleeping with a man? Maybe you're just hyping up 'The act' so much.Or are you ready and you are just nervous. Most of us were! This woman clearly has no expectations of you being an absolute superstar in bed, you have no experience - some women like that so it benefits you both. Don't not do it because you are worried you will get your heart broken - you will have your heart broken plenty of times in your life so crack on with the experience of it I say. In a lot of people's experience, that I have spoken to anyway, the first time is scary but a huge anti climax. Not sure if that helps but try to be a bit more care free about it all. (Obviously take precautions etc) but don't play it up to be this big, life changing, becoming a man sort of ritual. It is just sex... in time you will learn that 'just sex' isn't a big deal - it is actually when you want to make love that it becomes more of an 'occasion'.What is the worst that is going to happen? There is a risk in everything we do - I say go for it, get it out of the way and realise that you were worrying over nothing.Have fun! ;-)
A
female
reader, anonymous, writes (3 January 2019): Wow seems i am outnumbered and most are encouraging you to go for it.
Just think about if you want to really do it and look at every way to keep yourself safe, if you decide to do it i hope it goes well for you.
Take care buddy
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A
female
reader, YouWish  +, writes (3 January 2019):
 OP, why are you hesitating?? She sounds like any other person out there with a harmless fetish, and you DID post in public for a random sexual encounter!
I agree -- pay for a hotel room for the deed, even though I think given that she didn't care whether she had sex at her own home or yours that she's got cameras or anything.
I'd say you only live once, so get a bunch of condoms and stop wasting time! Everything's above board and on the up-and-up! You are both consenting adults and no one is leading the other on. This is your opportunity to piss away due to time-wasting and hesitating.
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A
male
reader, anonymous, writes (3 January 2019): It is true that meeting people online has some element of danger. Some people want to scam you, or worse...Youve met in public which is good, and she seems to be who she says she is. Blackmail is a risk. It is also a crime. If you know her real name and/or where she lives, then she would be unwise to blackmail you because you could just go straight to the police. And in case this does happen, that is exactly what you should do. Don’t reply to her or do anything unless the police instruct you to.It you are really worried, be straight with her and ask to see her ID. Unless she’s up to no good, she’s unlikely to be upset by this. Sadly, blackmail is very common so your caution is reasonable. Either way, don’t exchange compromising photos or anything else that could easily be used against you. Also keep in mind that photos taken with your phone typically contain the location the photo was taken (it is possible to remove that information). Meeting at a hotel is not a bad idea since it’s neutral territory.
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A
male
reader, anonymous, writes (3 January 2019): I tried to put myself in your shoes and think back what I would have done in a similar situation, and I can tell you without hesitation that I would have gone for her and followed her to where ever she wanted to take me come what may. I was very adventurous when I was your age. Faint heart never won fair lady.
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A
male
reader, Phil052  +, writes (3 January 2019):
 You wanted something, you advertised for it, you had a response, now you are backtracking. Are you worried about the act? She will understand you need to take things slowly. She is there to help you, sounds like a good opportunity for your first time to be special.
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A
female
reader, Anonymous 123  +, writes (3 January 2019):
 So it's a no win situation? You wanted someone to answer your ad even if you put it out there on a whim. You went ahead to meet the woman who answered it and she was attractive beyond your expectations.
So now what do you actually want? Given that all the boxes are checked and you're still skeptical, how can we, strangers on the internet, tell you what you should do? If someone tells you to go for it and you do indeed get scammed then you say, oh you guys told me to go ahead and now look where I am now. Even if this woman is genuine and is who she says she is, the way you met her and the circumstances under which you met her... circumstances that YOU created... make her seem shady.
As I said, it's a no-win situation.
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A
female
reader, chigirl  +, writes (3 January 2019):
 What do you actually want? I think you arent sure about it. And a good rule of thumb: when in doubt, dont buy. Im sure she is a lovely lady, but shes not the one, or something else about this arrangement dosent sit right with you. Trust your gut on this one.
If you had been sure about this, and wanted her, you would not have written to us, and you wouldnt have worded yourself with doubt.
Ask yourself if you will regret it if you dont go for it. Or will you perhaps regret if you do? Shes not a unique case, there are more women willing to, and wanting to, have sex with you.
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A
female
reader, Honeypie +, writes (3 January 2019):
 It all sounds like a bad porn story from the 1970's Playboy....
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A
female
reader, Andie's Thoughts +, writes (3 January 2019):
 Oh come on.... 100 women by 20? Ridiculous. There is no way you have put in effort to try to date 100 women. If you have, DESPERATION is why you're being rejected.Don't do it. You need social skills, not sexual ones. No use for sexual skills if you can't get dates.There's a high chance you'll fall for her because you'll feel pseudo-relationship emotions when you hook up. Bad idea.95% of teen relationships mean nothing, particularly in comparison to actual relationships in adulthood, so you haven't missed out. I understand that you're desperate, but you're only thinking short-term and that won't help you. You'll come back saying you had sex and either fell for her or still can't get a date.You are the common denominator in all of those date rejections. How did you know these 100+ women? How did you talk to them? How did you ask them out? How long did you know them? Why did you ask them out? Where did you ask them out to? How old were you?Being a virgin under 25 is common. Being a virgin under 30 isn't weird either, though it may be down to social behaviour - which is what your situation sounds like.
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A
female
reader, anonymous, writes (2 January 2019): Sounds very dodgy to me, sorry but it is hard to believe that this woman is above board with her intentions. If it is true she basically gets her sexual kicks out of sleeping with young lads, i am in my forties, i just don't get it.I know it is hard because of peer pressure to lose your virginity but i don't think this is the way to go about it, my feeling is this will go wrong and you will be left in a negative way one way or another. I don't know how you goo about trying to date, are you on dating sites or the phone dating ones (never used or seen them so no idea what they are called), you said you have dated or tried to date a lot of girls, the amount you have stated seems a lot, are you acting desperate? Look there are no easy ways to meet someone, but just going out, joining things of interest to you, meeting up with friends or joining reputable dating sites is surely going to be more successful than sleazy sites?Why not look at subtle ways or how to talk and flirt with the opposite sex and speak to girls you genuinely find attractive instead of how it seems, en masse....But my thoughts are if something seems to good to be true the chances are it is and something doesn't seem right with this woman...
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A
female
reader, anonymous, writes (2 January 2019): I think that kind lady is just being a good Samaritan, OP. No reason to be so suspicious. A long time ago I did the same thing for a dear friend of mine. Yes, I slept with my virgin friend. It was either that or letting him lose his virginity to a prostitute. He had made up his mind. I couldn't let him do that. The difference here is that we knew each other so I can understand the lack of trust in your situation. Perhaps suggest to sleep with her in a place of your choice? Maybe YOU book a room somewhere and you go there? Remember to use a condom and practise SAFE sex. Have fun and be grateful for someone like her. I wouldn't do it for a stranger but I did it for my friend as I cared for my him very much. Nothing sleazy as I didn't have a boyfriend at that time. Just one night with him. I thought we would just have platonic sex. He eventually developed feelings for me which meant our friendship was over. We no longer keep in touch. But looking back, I would have done it again if I had the choice. Take care.
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A
female
reader, anonymous, writes (2 January 2019): One thing strikes me about what you say in your post.That she wants to meet you in the city, so she is less likely to bump in to you in the future, but is happy to go to your house or hers, for sex. So, how does that make sense?If you're looking for anomalies in this situation, just thought that that statement doesn't make any sense to me.
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