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.
View related questions: divorce, escort, flirt, friend with benefits, get a girlfriend, shy, still a virgin
|<– Rate this Question|
Reply to this Question
Fancy yourself as an agony aunt? Add your answer to this question!