A
male
age
30-35,
*erry1992
writes:A bit about myself. I consider myself somewhat of a dork. Not good at sports. Tall but not confident. Naturally skinny. I was never good at dating, girls liked to chat with me but I end up friend zoning them. I always thought this was due to my androgynous look so I strived to achieve masculinity by going to the gym three times a week. I have been on a few dates. Twice it was the girl who asked me out but they quickly lost interest in me and I was still a virgin at this age. At the same time I get a lot of compliments from older women. You know, people like my school teacher, my aunt, the elderly lady across the street who say things like - why isn't a handsome young man (I personally do not think I am handsome) like myself attached to a nice lady. Some even want to introduce me to their unmarried daughter.One such woman is my hairstylist. She is 36 years old, about a decade older than me. She sometimes asks questions like do I have a girlfriend. I find her quite attractive though to me she was simply this attractive older woman. Sometimes I felt like she was flirting with me but I brushed it off. Like when she was brushing hair off my shoulders. Pun intended haha. Just the way she touches me. I also noticed that whenever I made an appointment she would be dressed up nicely, often sexily. If I didn't have time to make an appointment so she didn't expect me then I would see her in ugly t shirt and jeans. I chat with her quite candidly about the women I went out on dates with. Sometimes she did my hair for my date nights hence the random appointments. She knew I was seeing this girl from my office whom I thought was the One. However as always I got dumped at the end. I was super depressed this time. So I was at my next hair appointment and my hairdresser noticed I was depressed. She said I looked sad and thin and said I will find someone who deserves me someday. She the also noticed my stubble. Actually my underarm stubble as being a metrosexual hipster I wear tank tops 24/7. Being depressed I had neglected to shave my underarm hair and she noticed it. I didn't expect her to ask me if I wanted her to wax my hair. She said she usually offers this to female customers as there are not many metrosexual men that care about their looks. Anyway we did it. I was quite painful but I felt aroused in a way I never felt before. She also commented that she has never seen me not wearing sleeveless. I said it was my dress style and she said it suits me as I am tall and slender and it accentuates the shape of my shoulders.Then I wanted to book my next month's appointment. I usually book on a Saturday as I work weekdays. She works 6 days a week Monday to Saturday but only 11pm to 3pm. This time she suggested why not come to her apartment some customers actually come to her apartment for haircuts. She said just give her a call on her mobile an hour before and don't mention this to her boss as she is stealing his business. She then hugged me and told me not to be so sad and shop for new shoes to forget about my breakup.After this particular appointment I felt something I never felt before. I was very sexually turned on by this yet I brushed it off.A month later I needed another haircut. It was a Thurs so I rang her for my first haircut at her home. She was dresses in her home clothes but I didn't expect her to be dressed so laid back, she was actually wearing her night gown with nothing underneath. I can't remember the sequence of events but after my haircut we ended up having sex. I lost my virginity for the first time. I was so unprepared I didn't use a condom. I remember rushing home shocked at what had happened. I remember too shocked to go to work the next day. I remember doing an STD test. I was also disgusted with myself because she is married and because I knew it.A few weeks later I was at her boss's shop for a haircut. It was awkward meeting her. I apologized for blocking her phone calls. I apologized for taking advantage of her. She said we should sit down and talk. It was weird but she gave me a haircut then we went to one of the restaurants in the shopping mall. She said please don't feel guilty I wasn't taking advantage of her actually it was the opposite. She explained that she was attracted to me the first time she set her eyes on me. Something about being lusted upon by a women aroused me so much that we ended up having sex again that night. Her husband was on a business trip. It felt morally wrong so I told her we should stop it.I have since quit my job and left the country to pursue higher education. But also to do some soul searching. I have been on dating apps a lot lately. I used to list my age preferance as 20 to 25. But now I select 20 to 35. Most of the women who respond are 30-35. I have gone out on dates with several older women and sleep with two older women. The relationships never went further as they were after a casual hookup with me.I at a very weird point in my life now. I do not relate at all to normal people. I feel a deep feeling of disgust. Yet an euphoric feeling everytime I go on a date and enjoy getting these attention.Is there something fundamentally wrong with me that causes older women to be attracted to me? Maybe I am effeminate in some way. Or did my first sexual experience damage me. Like the way some girls lose their virginity at an early age to bad boys and then keep getting attracted to other bad boys?
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condom, depressed, flirt, lost my virginity, std, still a virgin Reply to this Question
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male
reader, anonymous, writes (18 September 2018): You come across as a guy who lacks self confidence or perhaps isn't very dominant in personality. I am curious, these older women you bedded, were they more dominant it bed? If they were, they are probably after more sexually submissive men and were able to pick up clues when interacting with you.
A
female
reader, Youcannotbeserious  +, writes (16 September 2018):
 As an older woman myself, I have lost count of the number of times I have looked at a young male who seems to struggle getting attention from females his own age and wondered, "What is wrong with these girls? Why do they not see how attractive/nice/personable he is?" I look at these young men and think, "If I had a daughter, that is the sort of boyfriend I would like her to have."
I think, as you get older, you appreciate different qualities in other people/the opposite sex to those you looked for when you were younger. It did cross my mind that, as you are very "into" your looks and grooming (not a criticism, just repeating what you have said), whether ladies your own age will see you as "high maintenance". It has also been my own observation that many men who are very good looking and well groomed seem to think this is all they need to attract women. While their looks may ATTRACT women, they will not KEEP them. Physical attraction will grab someone's attention but not keep it if personalities don't gel.
Why do ladies your own age end the relationship with you? Do you take time to show interest in THEM or do you just talk about yourself? Do you have interests you can share with them? Perhaps working on your PERSONAL skills, as well as your looks, may bring better results?
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A
reader, anonymous, writes (16 September 2018): WiseOwlE is right. He’s said it, but I’m going to say it too.... NEVER have sex without a condom. If you are unprepared, DON’T HAVE SEX. Women their ages can still get pregnant and then you’re stuck for the rest of your life explaining to your child why their mum was just a casual cougar hook up for you.
Get tested for STDs a month after unprotected sex and don’t do it again.
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A
reader, anonymous, writes (15 September 2018): You're a victim of your own overthinking. You study and analyze things to the last molecule; and if you keep doing that, you'll never enjoy anything. You're living in your head.
Never have sex without a condom. You know better than that!
You have to be tested with a full-battery of tests for STD's; 30 days from the time you had unprotected-sex, for more accurate test results.
There is nothing wrong with dating older-women; just don't come-off like a gigolo. Your youth draws attention to you; and younger women are just aware that they have just as much access to variety out-there as men do. They can be just as casual about sex; and otherwise, as picky as they like. Many are jaded, cynical, and have too many insecurities. So, you have to date quite a few; and take your time to meet your match. You have some catching-up to do!
Social media has conditioned people to be less emotionally-involved, and evasive of real commitments. Avoiding possible disappointment, having unrealistic-expectations, and dodging responsibility. We seek all the wrong things from people, for all the wrong reasons. Sex being the prime-objective.
Finding something meaningful is too often an afterthought; maybe considered too idealistic. So I guess the common focus is more on getting lots of attention, seeking popularity, and craving validation. All for the sake of vanity. Maybe you missed-out on a lot of experience through high school and college. I'm not talking about sex; I mean forming emotional-attachments. That accounts for your confusion.
I think people are quite wary of commitment; which requires long-term effort, and letting people inside your head. That demands more of people. You're exposed and vulnerable! Intellectually, psychologically, and emotionally! That's scary! Being physical is simpler, because it's primal and instinctive. It's immediate-gratification. So you're getting a taste of that side of online-dating. They expect little more of you than your dick! They think that's all we men want anyway!
In due time, you'll meet someone who will tap into a more emotional side of yourself. She'll stir your deeper feelings. You could meet quite a few people before that happens. There is nothing wrong with you. You're just inexperienced and you are being too analytical. It also seems you have a lot of preconceived notions about things. Over-time you will develop better discernment and people-skills. You will have a better grasp of who you are. As soon as we discover who we are; that's when we finally know what we want and need.
You need time to accumulate experience, be more serious about forming meaningful-relationships with women; and form more sensible and mature opinions. You're a late-bloomer; so your arrested-development makes you awkward out there in the world of dating. Outgrow the tank-tops, and dress like an adult. You're a man now! Your boyish-mentality is getting in your way! Women see it! You're quick to friend-zone; because you're not confident that you're equipped to carry-on a romantic-relationship. Maybe virginity made you a little apprehensive or shy about females.
For one thing, you've been unfairly dismissive of women your age. You don't take them seriously; mainly because you don't know what to do with them. Older-women can guide and direct you, to some degree. They are less apt to play games; but they will use you for a boy-toy, if you don't grow-up and wise-up. Your naivete is your appeal; but as you project more maturity, you'll be taken more seriously.
Come-on! Always wearing tank-tops is a just a wee-bit dopey!
Hopefully, with experience and maturity you'll become more prepared, psychologically and mentally, to have a more serious and meaningful relationship with a woman. Something beyond flings and hookups. You're like an adolescent pushing 30! That's just an observation, I don't mean it as an insult. We've never met, I have to form a picture of you from your self-description and story.
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A
female
reader, janniepeg  +, writes (15 September 2018):
 Most online daters are looking for casual relationships. If women can pick they of course would pick better looking, younger men than mid aged men who are deflated in energy or down there too. You said you get dumped in relationships so you feel older women are easier to get with. They on the other hand feel they have power and control over your attraction to them. They also have the confidence due to experience.
I don't think first time experience damages anyone. Anyone who thinks that wants to blame on the past and never move on. I have to warn you though, if most of your experience comes from cougars who want to take advantage of your innocence then leave you high and dry, then you will never learn how to trust women and to devote time and energy to the right ones.
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