Search Results: sex with an older woman

I am a 25 year old 5'6" male and I never had a girlfriend. I have only had sex once in my life when I was 20 (she was 16). We both lost our virginities to each other but she never wanted a relationship with me. I was thrown in jail and have a stalking conviction on my record all because I brought her a cookie cake around 7-8 months later trying to ask her out to her prom (she was now 17 at the time).

I once tried to make a relationship happen with this one other girl, but she ended up becoming a transgender (became a dude). I can't believe I made out with her one time.

Like I said I am 25 and never had a girlfriend. I only had sex once in my life and it was back in 2015.

Not only am I short and never had a girlfriend, I also lost my career. I had to voluntarily surrender my EMT license (it was going to be revoked anyways).

I still live at home and on disability.

I also have an Autistic Spectrum Disorder and other mental health issues.

I have been hospitalized over 13 times in my lifetime, all starting from adolescence.

I have been trying to learn programming and web development for over 3 years diligently. I am still an ameatur and suck at what I do.

I cannot get ahead in life it seems in the romance or the career department.

I only want a decently attractive woman without a romantic past (meaning no previous boyfriends or romantic bonds), but I will likely remain alone because I will never find that I feel.

I am failing at life. Period.

OK, so I turned 50 a few months ago, but I have taken good care of myself, am a successful person, my kids are grown, and I divorced two years ago. I have always been told I am very handsome, but I have never really taken this seriously.

I started on a dating site about 10 months ago and put the age parameters to "ages 40 to 50" and began reaching out to women and they reached out to me. Here is what I found out:

I went on about a dozen dates with women who are "in my age range" (40 to 50) and was really disappointed. These women did not look at all like their profile pictures, most of them are seriously overweight, wore way too much makeup, didn't have much to say and overall they were completely unimpressive. These women seem hell bent on trying to recapture their "roaring 20's", even wearing inappropriate clothing, trying to put off an attitude of "I'm so sexy baby".

At the end of every date with with above 40 to 50 year olds, all but one was ready to have sex with me. I did have sex with four of them but I never had any intention of seeing them again -- shitty, I know.

I talked to a friend of mine and he said, "dude, why TF are you dating 40 to 50 year old women when you can have 25 to 30 year old women". I was kind of stunned. He leaned over my shoulder while I logged in to my dating site and made a few tweaks for me. Let me say, my profile is totally honest with very current photos, career, and information. Having said that, I reached out to some seriously hot women in the 25 to 30 range fully expecting to be laughed at (then go kick my friends ass!). To my surprise, I have an inbox full of messages from extremely attractive women all of whom are between 20 to 30. Amazing! I could never have attracted these women when I was 25, but so be it.

Having said all of the above, I am gearing up for a first date tomorrow afternoon with hottie #1. She is 26, a stunningly beautiful brunette, and she seems ready for action.

Am I totally fucked up?