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The movements are small but energetic, my pounding on his sphincter leaving us both drenched in sweat, me from exertion; him from pain and fear. After a minute I look and see that my efforts are succeeding in tenderizing this tight young muscle; the first inch of the oversized glittery toy now firmly ensconced and gripped by the tight ring. I apply more lube, and resume my thrusts, harder and longer now as he is stretched wide enough and I just need to force in 2 more inches before I let his anus tighten on the narrower shaft of the dildo. Another minute of pounding, Jimmy’s screeching having descended into exhausted grunts, and I have gained no more than a half inch more. I adjust my grip on his thighs, and brace my legs beneath me to power my thrust, ready to stop the moment I’m in. I take a breath and hold it before pushing forward inexorably. Jimmy tries to lift away from me, his toned muscle defying my hands, but his restraints only allow him so much before he cannot go further. Afterwards, I decided to finally go to a urologist and have my cancer checked out. Turns out it was nothing, it took about 10 minutes to fix and I drove myself home. All that stress, anxiety, self hate for nothing. Then I went to college. My confidence is at an all time high. I'm getting laid left and right. Some one night stands, some week+ long relationships. Some a month, some 6 months. Lots of sex, lots of blow jobs, almost always coming back for more. So, I never once thought of my penis size (besides that I'm a grower, not a shower, so I knew getting naked flaccid was a no go). Move onto age 23, I meet the one. Sex is great, everything's great. No complaints in the bedroom, making her cum was always job 1 (it's not a job, it's the best part, imo). A few years go by, we hit a rough patch and split up for a couple month or two. I sleep with some more girls, all multiple times, all with no complaints. I even go back and sleep with my first girlfriend, who is actually married at.
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