As I entered my middle thirties, I thought I was fairly well versed in the art of masturbating. But I was about to explore something deeper. Although I had occasionally inserted my fingers into my ass when I masturbated, my body was crying out for a more intense experience.
I got up the urge to buy an anal plug, a large one, to try while I masturbated. It took me a while to convince myself I wasn't gay or bi, just a straight guy looking to get himself off in the privacy of his own bedroom.
When I finally got up the courage to use it a few days after I bought it, I put a towel underneath me, layed on the bed, used a TON of lube on my hands, my ass and the plug and got started. I spent a few minutes just rubbing the lube on my cock and balls and down to my asshole. I was so horny knowing I was about get fucked by the plug. I breathed and urged myself to relax as I worked two fingers deep into my ass, moaning as I rubbed my prostate gland. Pre-cum was flowing out of my cock.
Then it was the moment of truth. I picked up the plug and placed the tip at my hole. The plug had a barrier at the end so I knew no matter what, I wouldn't get stuck. I jacked my cock some more and then slowly, carefully, began to insert the plug. It looked big, but as it went in, it began to feel even bigger. I breathed slowly, urged my body to relax, and worked the plug deeper. Uncontrollably, I began moaning and crying out at this new feeling of fullness. I was being fucked in my ass for the first time and I loved it. The plug went deeper and deeper into my ass. Finally, I felt it slide all the way in. I moved it up and down slowly as my swollen cock begged for relief. I wanted the moment to go on forever. I had surrendered to this feeling of being ass fucked by a butt plug and just accepted it knowing I was in complete privacy and could explore the feelings safely. I had admitted to myself that I enjoyed being ass fucked by a plug while I jerked off and that made me even hornier. I imagined a woman helping me and talking dirty to me. Finally, I couldn't take it anymore. The plug went up and down rubbing my prostate and my hand was jacking the sensitive spots underneath the head of my cock. I screamed and cried out as my orgasm overtook me. Rope after rope of hot come flew out of my cock all over my chest and stomach. Slowly, I withdrew the plug and lay there on the bed for several minutes. Then, without warning, I began to cry, feeling momentarily guilty and ashamed, worrying that I might be gay again (which is stupid, I know). I finally calmed down and relaxed knowing that I soon wanted a woman's help in working the plug.
Several times a year, I still masturbate with that same plug and each time, it is a truly wonderful experience, and yes, several women have given their help as I have done it.