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Discovery in the Realm of the Prostate

Posted by: Age: 40 something then Posted on: 6 comments
14 likes 643 views Category: Masturbation Male-Female Tags: anal play, vibrator, prostate, ejaculation, assisted peeing

I was never big on anal play. And the prostate was always a mystery to me. Then I had an experience that, shall we say, gave me some instructive insight. The story also digresses to describe attempting to pee while a woman is holding my cock.


I never had much desire to try anal play or anal intercourse. Just wasn't drawn to it or turned on by the idea. That inclination was reinforced by a couple of exploratory experiences with a girlfreind in my 20s. We were both a little curious and played around with a vibrator in each other's asses. For me the sensation progressed from uncomfortable to painful and I thought "Right, this is not for me." I also couldn't imagine why a woman would want to experience that and no woman ever begged me to try it. ( I know, all you aficionados out there will say I wasn't doing it right. And I have since met several women who've told me of experiencing a rare ecstasy through anal intercourse. But what did I know back then!) It wasn't until my 40s that I had an "Aha!" moment that showed me see why folks might get off through their ass. I had a lovely 'friend with benefits' called Allison who managed an apartment building. We used to get together weekend afterrnoons and play for a couple of hours or more. All of it was non-penetrative and tremendous fun. I would arrive at her door with my pants unzipped and cock out, semi-erect or more. When she opened she would smile, look down, and grasp my cock to pull me into the apartment. From there we might jump straight into a bout of frenzied sucking, fingering and wanking. Or we might sit down, drink tea, and watch TV or talk about the week, touching each other just enough for her to keep my cock hard and me to keep her nipples stiff. She loved to watch me pee and sometimes to help. She would stand behind me, unzip me, and take out my cock, holding it and directing the stream of piss. This could be tricky and led to some humorous moments. If I was already pretty horny her touch would make my cock stiff enough to prevent peeing. We would then go through this little dance where she would let go long enough for my erection to subside and then take hold of me again. Sometimes this worked and I stayed limp enough to pee. More often I would grow hard again and my cock would go through a cycle from semi-limp to semi-erect and back again. This process became intensely arousing in itself. I could feel Allison start to press her breasts into my back and her hips against my ass. Her breathing got heavier, as did mine. Once this started there was only one way I was going to get to pee. She gripped my cock firmly and began to wank me steadily. Her other hand came round my chest and started to rub and pinch my nipples. As I got stiffer and the head of my cock swelled she started to make appreciative "Mmms" and thrust her hips against my ass. My ejaculations from this were always amazingly intense. Afterwards she would squeeze the last drops of cum out of my cock then let it rest gently in her hand while it subsided. Or sometimes she would fondle my balls while my cock caught its breath -- until, finally, I could pee, with her holding my now-limp cock and directing the jet. Then we would usually collapse in the bedroom and I would express my appreciation by burying my head between her thighs, and my tongue in her pussy, already dripping wet from the bathroom adventure Ah, I digress! How memory sidetracks us. I started to write about anal play and remembered some other games with Allison a little too vividly! So back to the original topic. One afternoon we had already been playing for a couple of hours without cumming so were very highly tuned sexually. We'd been messing with a vibrator and some other toys and I decided I would like to see what prostate massage was all about. I was naked and Alison was wearing a bustier. It pushed up her breast and her nipples peeked out at the top.The bottom flared over her hips and the top of her ass but left her pubic hair and pussy exposed -- very sexy! We stood in front of her dressing table which had a wide and tall mirror at its back. I spread my legs and leaned forward, hand on the table. She lubed up my asshole and the tip of the vibrator and started to work it into me. As she did that I took one hand off the table and started stroking my cock. The mirror gave us both a great view of the action so, of course, made it doubly arousing. This time the sensation was still uncomfortable but not painful. However, it did seem to release some raw, primal energy. I had imagined that massage of the prostate would produce some ecstatically pleasurable sensation but it wasn't like that. Instead, I noticed that my cock had grown longer and stifferr than usual. I was pumping it urgently (My wanking is usually slow and sensual.) Together with that I was grunting and groaning like an animal while thrusting my ass back onto the vibrator. Alison was caught up in the energy too, rubbing and pressing herself against me and gasping loudly. When I finally came it was with a loud roar. When I ejaculate my semen usually just flows out. I haven't squirted much at orgasm since my 20s. This time was different. I vividly recall the two long white threads of cum that pumped out of my quivering cock. One after another they hung for a second in a perfect line parallel to the floor before dropping to the carpet. That's how I finally discovered what prostate stimulation has to offer!    

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