8 years
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I had always wanted to get fucked by a girl with a s******. I had been alluding to this with my ex wife when we were newly married and she always said she would love to see me having s** with another man. Well one day she asks me if she can f*** me that night. I’m so surprised how blunt she was about it. I smiled and said yes. So we drove to the s** store and parked outside she said “well if you want to het fucked go buy yourself a c***” and left me to go into the store alone. There were a decent amount of people in the store and I browsed the strapons until I cam across the one, a white 9 inch very realistic veiny c***. I walked up to the counter nervously and so obvious that I would be on the recieving end of the toy. I brought it out and she said good boy to me. After getting home I showered and shaved myself nice and smooth and made sure I was cleaned up. When I went in the bedroom she was standing there and told me to get on the bed. I climbed onto the bed and she told me to bend over. Then she presses the c*** against my a****** and tells me “if you want it so bad then back up onto it and show me.” That was probably the sexiest thing I have been told about taking a c***. I eased myself back onto it eventually taking the whole 9 inches. I was so excited and rock hard. She held my hips and thrust into me telling me how s*** i looked with a c*** in my a** and saying baby you look so damn hot right now. I was 21 6’4″ 185lbs with an 8 inch c*** myself and at the time and she was 23 5’0″ 125lbs and nice by d cup t***. She fucked me a lot but I never opened up enough to s*** it. Now with my current wife I am such a s*** for it. She calls me her c*** w****, cumslut, cumdumpster. It’s all playful and I love the role reversal. I have yet to take a real c***. But hopefully I will have one c****** soon.

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When I was younger, about 16, I was insatiable and as a result of having my first anonymous hookup with another kid that was 16 (off omegle of all things) I sought to have more.
In this effort I downloaded Grindr and lied about being 18, eventually finding someone who hosted an anon darkroom not even 5 minutes away and who was more than happy leaving their door unlocked and a** ready. After I was invited over and tentatively entered their place I immediately set about u*********, going to nothing in a minute and slowly started up the steps to his room. Once in his room I was approached in the dark by him – a 30-something yr old man who was equally as naked but twice my size – and he reached down and started to blow me once he settled on his knees. Within minutes once I was sufficiently erect I prodded him onto the bed and had him bend over, eventually sliding in without any additional lubrication and begun to – at the age of 16 – f*** this older mans a**. I went for about 20 minutes by my estimation and slowly over the course of the f****** went from doggy, to sideways to having him lie fully down whilst I went to town on him.
Eventually I finished in him and got up and left. Once home I gushed to him about how much fun it was and how I appreciated him taking a chance with me, with some more conversation eventually leading to my age being revealed and – to my own surprise – him revealing that he’d prefer it if we kept going in spite of it. I’d meet him continuously, probably once to 3 times a month or even multiple times in the same week until I moved away at 18. I never saw his face but I remember being inside him so vividly.