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First time milking my prostate

Date: 7/24/2015, Categories: Anal, First Time, Masturbation, Author: Fatdick604, Rating: 94, Source: xHamster

I don't exactly remember when I first got the urge to pleasure my asshole but I'll never forget how good it felt when I slid my finger up my ass for the first time. I have never been attracted to men in a romantic way but I do love cock and consider myself a bisexual when it comes to sex. But my first love is women and I just don't see myself ever being in love with another man or in a relationship. As I got older I began cumming in my mouth by lying against a wall and putting my legs over my head so I could aim my cock for my mouth. The first time I chickened out and closed my mouth before my cum could get in. Instead I just came all over my face but the second time I let every drop go right down my throat. It was so warm and tasted gross and left me feeling confused about my sexuality, wondering if I was gay but knew I still loved girls and wondered why I was doing what I was doing. I began to experiment more and more with my finger and felt guilty about how much I loved the feeling of something in my ass. I started trying bigger objects and before I knew it my asshole was loose. I had this prop from a movie, it was a police night stick that was thick and black and hard. I slowly eased it into my ass and then decided too bounce up and down on it as hard and fast as I could and for ten minutes had an orgasm that just didn't stop. I bounced up and down while stroking my cock and I had the feeling of cumming over and over until I exploded. After that I thought about how if ... every man only knew how good it felt and that it gives you an endless orgasm, until you decide or just can't take it anymore, I'm sure every guy would love it.. I often wonder how many guys actually do it in private. One day I saw a huge thick cucumber in the fridge and got really horny, I wanted it up my ass but was wondering if it would fit. So I measured it and it was nine inches thick began to have a second thought, my ass was loose but the cucumber was fat and curved and making my dick hard. I was so horny and decided to at least try and went to the washroom and got naked looking and my hard cock and the massive vegetable in my hand. I got on my knees and lubed up my ass and placed it between my ass rubbing the cucumber against my anus so it got lubed up then I started. I slowly sat on it and I could feel my anus stretching and before I knew it part of the tip was in and I continued to ease it in nice and slow. It seemed to big and I was about to stop before I felt the cucumber slide ride up my ass catching me off guard and going farther than I wanted before I could stop myself from taking in anymore. Then something happened that never happened before, the cucumber hit my prostate and made my dick contract. As my hard cock contracted it shot out a gob of thick white cum and I could feel that it came from deep inside my body. I had just milked my prostate, within seconds of the cucumber hitting my prostate I could feel my cum as it made its way up my dick. I never felt such ...