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This happened 2 years ago but i really want to share it because i cant keep my mind off it.

 

Ever since i can remember i have been playing with my hole, many household items, toys and fingers have passed through but never a real cock. I tried multiple times by going to cruising zones and parks but everytime someone would aproach me a gigantic feeling of anxiety would come over me and i would bail on it.

The night in question was no different, i already spend 2 hours driving around to various area's. Getting out of my car only dressed in a jockstrap hiding my chastity cage and a t-shirt. But everytime someone would react to me i would just bolt out of there and drive away.

Getting annoyed with myself i decided to go to one of the best known cruising spots next to the highway, normally there is like 10 people there at anytime. But by now it was 4AM so there were only 2 cars there. I figured this is it, i would walk into the woods, wait a minute or 2 and if noone shows up i was gonna go home.

I get out of the car and walk into the woods with a tiny blanket, put it on the ground just in the treeline but right next to a path and got down doggystyle with my ass pointing towards the path.

First nothing happened, my heart was racing, but i was counting down in my mind, keeping myself there till i got to 2 minutes. In the last 15 seconds i hear footsteps behind me. My heart drops, but i use everything in my might to just stay put, wiggle my ass around a bit and seconds later i feel a hand on me...

No words said, he unzips and puts his bare cock in my hole, my entire mind is screaming at me to get out of there, but my body just pushes backwards taking him in completely. About half a minute of being fucked later i can feel him fill me up, and he gets up and leaves. About half a minute after him i get up and run back to my car and speed away.

 

Ever since then i have not been able to get myself to go through with it again, my anxiety is still through the roof, but i cant stop thinking about being used and filled up by him.

 

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