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Not for lack of trying [I Am Still Virgin]

Growing up I had a live-in babysitter… my stepsister who is 11 years older than me, and was very strict and didn’t allow me to do much of anything. That lasted until I went to college where I joined a fraternity and try to be a real macho man, I had girlfriends but never had sex because I’m too much of a wimp and I am super embarrassed about the tiny size of my dick. So my relationships never lasted more than a couple of weeks when girls either figured out that it was never gonna happen with me or they saw the size of my dick. After college I got a good job but spent all my money living it up and trying to be a playboy with basically the same results, until I get fired and had to sell my car in my condo to pay off my debt and ended up having to move in with my stepsister.
Cleancut · 56-60, M
I had a somewhat similar story. I had a strict mom who would never let me go out. Through my entire teens she left me with babysitters to enforce her rules and make sure I stay home.

I then went away to college, lived in a dorm and did have sex a few times. Then I had to move back home and to my surprise it was just like I never left. My mom said "If you live under my roof you follow my rules". I had an early curfew and she treated me like a kid. When she went out of town for a week she actually had someone's babysit me, I was 19 years old. Needless to say I had no sex while I lived with her. Other than one long-term girlfriend I had more sex in that college dorm than I did the rest of my life put together.
bhatjc · 46-50, M
Hope things are going better now.
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