5 years
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By all rights i should have ended up a pathetic incel. Plain looks tiny d*** and s******* frustrated because being a decent human being and having plenty of money does not guarantee s** when you are homely and under endowed. Oddly I have my mostly lesbian sister to thank for avoiding an incel fate. Parents threw her out for being promiscuous when she was 18 and i was 16. She snagged a sugar daddy that set her up. With her looks and s** drive it was easy for her. He does not care about her being with girls as long as he gets his piece when he wants it. He does not care if I visit her she even gave me a key. One day when I was just shy of 18 i dropped by unannounced and when I found her she had some girl face down in her in the bedroom and i just stood there watching. Sister smiled when she saw me and just kept enjoying being eaten out. I left quietly. Sister finally broke the weeks of silence by bringing it up. Told me that she knew a girl that would take my virginity if I would be ok with it being a 3some. I was too nervous to take her up on it. On a visit a week later she hands me a worn pair of p****** from one of her recent girls and says she saved them for me. So she started claiming the p****** of every girl she was with and gave them to me and i got hooked on jerking off with them. But she upped the ante by telling me eventually that she would cut me off the p**** supply unless I did it in front of her. I was pathetic and frustrated enough to agree. I felt so ashamed after but she finally got me past it by saying she wanted to help me however she could. So it became a regular thing whenever she collected a new pair for me. Even talked me into doing it whole tasting and smelling the p****** as I did it in front of her. Been going on for 3 years now.

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After my dad passed away I was taking my mom back east and he pulled into a rest area because there was no hotels available and I pulled in the very back and we both got in the back fell asleep. When I woke up i was soaking wet from the sweat because the humidity was so high and I got out of the van and I took off all my clothes it’s going to get some new clothes on then my mom woke up and she was the same way she’s just soaking wet so I just got back in the van naked and laid down and Mom got in front of me and we just laid there and I got an erection she felt it and she asked me if I had a hard-on and I said yes she reached back and started playing with my c*** and she said that we shouldn’t be doing this and we’re both adults mom we can do whatever you want so she started playing with my c*** some more and she put it right to her entrance to her c*** and I pushed it in I went all the way inside my mom and I started h****** her you really liked it so then she rolled over and I got on top of her back inside of her and we started f****** and I was pumping her really hard and she got off so did I I came inside of my mom’s p****. We laid there for long period of time and then I did it again I penetrated her and we fucked for about a good hour after that. I got up and put some clothes on and started to drive again. She told me that was the first time in years that she got off. We got to her sisters and we went out to eat and came back and I was going to leave early in the morning and before I left my mom came down to the room I was staying in she got in bed with me and fucked again