This is based on a true story of how I discovered the pleasure of prostate play. Most of the details really happened, with some small changes made for the purposes of storytelling.
My name is Jack; I’m in college in my early 20s, and would definitely consider myself a straight guy. I never really had any success dating women in college, not for lack of trying. I did, however, experiment a lot by myself. One day when I was jacking off to porn, I discovered “femdom” porn.
It was a video of a man who was tied down to a bed, with the dominant woman riding him reverse cowgirl, hard. She wore latex high heel boots, fishnets, and a corset. Her breasts were bouncing rapidly up and down while she fucked his brains out. And all he could do was squirm and moan while he was tied down to the bed. He was nothing more than a toy, useful to her only for her pleasure.
I had always considered myself to be more on the “dominant” side, but this type of porn had turned me on beyond belief. I decided to keep watching, and knew I was close to cumming. In the video, the guy came and lost his erection, and the woman stopped riding him. She said “did I say you were allowed to cum and be done yet? No, I fucking didn’t. Now you’re going to be punished.” The guy was apologetic, and started squirming around more. “Shut the fuck up” she said. He continued protesting, so she grabbed a ball gag and put it on him.
Watching this, my dick was super hard, and I felt myself getting closer and closer to finishing. In the video, all that could be heard were his soft moans through the ball gag. “That’s better” she said. “Now I need to make you hard for me again so that I can finish.” At this point, she walked over to a drawer, grabbed a dildo, and squirted lube all over it. When the guy saw this, he started squealing through his ball gag in protest.
“This will go a lot easier if you stop squirming” she said. She walked over to him, and squirted more lube on her fingers, teasing the opening to his asshole. She then slowly started pushing the lubed up dildo into his ass. “Mmmmmmm” he moaned through the ball gag. “You like that, don’t you?” she said to him. At this point, she had the dildo all the way inside him. “Now if we can just find the right spot” she said. Almost as soon as she said this, the guy’s dick became instantly hard again, and he jolted and shrieked in pleasure, again with the shriek of pleasure muffled due to the ball gag. “And there it is” she said seductively. “Now, where were we?” And with the dildo still in his butt, she climbed back on top of his rock hard cock. She started rapidly bouncing up and down, with one of her hands still on the dildo and rapidly pushing it into and out of his asshole. “Hmmgmgmmm!!” He moaned through the ball gag…
As I was jacking off to this, I couldn’t take it anymore, and I had a very hard orgasm. Cum was absolutely everywhere and I must’ve cum for around 20 seconds nonstop. “Holy shit” I said to myself. Why was that so hot? I was curious about what had happened, and I started reading online about men receiving anal sex. That’s when I learned about the prostate, and how it was basically the male equivalent of the g-spot. Apparently for many men, stimulating it led to ridiculous orgasms.
The next morning when I took a shower, I decided to use some soap on my finger and tried to finger my asshole a bit, just to test the waters. It took me awhile, but I couldn’t really get my finger that far in, I guess mainly because I was nervous and also because my arms weren’t long enough anyways to allow me to finger my ass very deep. But I really wanted to try to experience this type of pleasure, and that’s when I started researching sex toys online.
I decided the best approach was to order a small/moderately sized butt plug to help open up my anus, and to then move to a vibrating prostate massager. There was just one problem: while I was clearly very open minded and had no issues with exploring this sexual avenue, I didn’t want anyone else to know about it. There is just a certain level of taboo being a straight man but enjoying anal pleasure in our society, and I of course felt ashamed of my desires to have anal stimulation. I could’ve ordered these sex toys online, but my mom’s name was also on my credit card because it was my first card as a college student.
I really wanted to try this though. There was only one real solution I could think of: I was going to need to go to a sex-toy store in person and buy these things. The thought of going to one as a guy simultaneously turned me on and made me extremely nervous, especially because I’m really shy in real life. There was a sex toy store near my college campus, but I didn’t want to take the chance of seeing anyone I knew there, so I looked up another one that was a 30 minute drive away from me. I got in my car one Saturday, and drove out to it.
When I entered the parking lot, there were only a few other cars there. It took me a moment to work up the courage to walk through the front door, but eventually I mustered it up, got out of my car and entered the store.
When I walked in, I was greated by a young, sexy woman. Her hair was dyed blue, she was wearing a choker, a nose ring, and a white t-shirt that her breasts were straining against. She asked to see my ID. My hands were shaking because I was so nervous, but I had managed to reach into my wallet and pull out my ID to show her.
“Okay thanks. Let me know if you have any questions or want any help finding anything!” She smiled at me as she handed me my ID. I’m pretty sure she could tell how nervous I was and I’m sure my face was bright red. “Thanks.” I muttered softly back at her, barely able to look her in the eye.
The store was actually pretty nice. There was a whole section with racks of porn DVDs of various categories, walls of different kinds of sex toys, lingerie, and shelves with lube. Looking around the store I also noticed something else, something that made me more nervous and made my heart absolutely sink: I was the only guy in there! All the other customers were women! One was someone who looked to be in her 40s, with a very attractive figure. She was browsing the “anal” section of the DVDs. Another two were clearly a couple with each other, probably around my age, also with quite attractive figures. They were browsing a wall full of those “jack-rabbit” type dildos that many women seem to enjoy. Finally, there was another woman around my age, who was browsing lingerie.
I could barely stand let alone walk. Seeing all these attractive women made my dick hard, and I immediately did my best to hide it. I also had no idea where to look for what I wanted in the store, so I started near the porn section and decided to work my way around the store methodically. The woman in her 40s noticed me as I walked by her holding a DVD titled “Tight Anal Milfs 4”. I turned absolutely beat red while she smiled at me, maybe even slightly seductively. I just kept walking, I had a mission and I needed to get out of the store immediately because of how embarrassed and uncomfortable I was.
I kept walking around the store, passing a wall full of Fleshlights/pocket pussies, that type of thing. I reached the wall of dildos that the couple were browsing, and they seemed not to notice me really as I walked past. Not far from this wall, I finally reached a wall dedicated to anal toys. Butt plugs of sizes that I didn’t think were humanly possible to fit into anyone’s asshole, anal beads, training kits, etc. I grabbed a box that had a smaller butt plug in it; I was new to this after all! I kept looking and finally found the vibrating prostate massager that I wanted and grabbed that as well. I looked to my left and noticed that the fourth woman in the store, who was browsing fishnet stockings and thigh high socks, was looking over at me. She seemed nervous though and quickly looked away from me.
I needed to just get out of there. I grabbed a bottle of anal lube from another shelf as well as some toy cleaner (I had done my homework online before coming in, after all). I walked up to the counter, only to find that the woman in her 40s was ready to pay, holding a few raunchy DVDs in her hands. I stood a respectable distance behind her. While she was paying, I noticed that the couple was behind me, and the woman browsing lingerie had also gotten in line. I was so embarrassed, standing there with my anal toys and being in line with all these hot women.
The woman ahead of me suddenly said “shit, I forgot there was one more DVD I was looking for, I’ll be back in a bit.” “No problem, I’ll hold on to the DVDs for you and when you come back you can finish paying.” I was mortified, but it was my turn. “Did you find everything okay?” She asked me. “Umm.. yeah..” I replied quietly and clearly very shyly. I put down the butt plug, prostate massager, anal lube, and toy cleaner in front of her.
What happened next made me even more embarrassed than I already was. To the clerk’s credit, she was absolutely professional about the whole thing. “I’m just going to take the toy out really quickly to test it before you buy it, just to make sure it works okay?” Shit. I just wanted to leave, and the clerk was going to unbox my prostate massager for all the other ladies in the store to see. The clerk just smiled as she took the toy out. She started pressing buttons on it, and the toy started making “vvvvnmnmvmmmvmm” noises much louder than I would’ve liked it to. At this point, the older woman had gotten to the back of the line.
It felt like all the women in the store could hear my thoughts, could see my private desire to fuck my asshole. I was so simultaneously embarrassed and turned on; trying to hide my rock hard cock and my beat red face, shaking in my boots due to how nervous I was. I knew. The clerk knew. Every woman in line knew: I was going to go home, and shove these toys in my asshole, ejaculating everywhere after I was done pleasuring myself. The clerk continued testing out the toy: “vvv vvv vvv mm mm mm mm” which made different noises with different vibrational modes. I could barely take it anymore, I was sweating like crazy. The women who were a couple seemed more or less indifferent to what was going on, probably telling me they didn’t really care and thought it wasn’t anything out of the ordinary to see a dude buying anal toys. The woman behind them who had been browsing lingerie was also beat red in the face, and was just staring at the floor. Finally, the woman in her 40s had the biggest grin on her face as she stared into my soul, knowing my every desire to have my prostate fucked.
The clerk finished testing out the toy and put it back in the box. She asked me how I wanted to pay and I abruptly said “cash!”. She kind of chuckled as she took the money from me and gave me my change. “Thanks for coming in today, hope to see you in here again! If you have any questions or concerns, please give us a call. And also, if you want to be a regular customer, you should consider signing up for our rewards program!” She gave me a sexy smile and a wink. “Uh, sure” I muttered in shame as I walked abruptly out of the store.
When I got back to my car, I told myself “you did it, that was the hard part, it’s okay” as I calmed myself down. I started the drive home, and now was completely and utterly turned on. I had just humiliated myself in front of all those women in the store, and I had a similar feeling being turned on at the thought of being submissive to a dominant woman. I was also incredibly turned on at the thought of sliding the toys into my lubed up asshole.
When I got home, I immediately showered just to make sure that my ass was as clean as possible. I then ran to my bedroom and unpacked the toys. I put a towel down on my bed. I put some porn on my phone and took off all my clothes. I lied down on the towel with the toys and the lube in reach of me. I started playing some femdom porn; I had chosen a pegging compilation, and watching dudes get fucked hard by scantily clad women had me turned on beyond belief. My cock was harder than it’d ever been in my life. I lubed up a finger and started to rub my asshole, preparing it to be fucked hard.
I started rubbing the entrance to my asshole, which felt amazing on its own since it was so sensitive to being touched. I got out the butt plug and lubed it up. I started to push it into my asshole; even though it was small, I found it very difficult to get in. I did my best to take the advice I had found online, to just take it slowly, try to be as relaxed as possible, and to not force anything. I also tried “pushing” the butt plug out of my ass, which apparently would help to get it in since this would have the effect of opening my anus more.
It felt absolutely amazing to have my asshole getting stretched out more and more by the butt plug. Finally, after 30 minutes or so, it suddenly went all the way in when I got past the widest part. I’d never felt anything like it, but it felt incredible to be just “filled up”. My dick was super swollen, it was almost a purple color, because of how turned on I was. “Ooohhhh my fucckkiiinnnggg gggooodddd” some guy moaned on the porn video I was watching as a woman in a nurse costume was pegging him super hard.
I left the butt plug in for awhile, and when I felt comfortable I removed it and decided it was time to move on to the prostate massager. I lubed it up and started to slowly push it into my ass. It seemed to be going in easier than the butt plug, but I had to periodically remove it, add lube to the tip, and put it back in again to keep it going in.
That’s when it happened. It suddenly went all the way in, and the curved part of the prostate massager had poked my prostate hard enough to make some precum ooze from my dick. The pleasure was unlike anything I’d ever felt in my life. I couldn’t believe I was doing this: my ass was filled up completely and I was going to fuck my prostate. I turned on the vibrator by pressing a button on it. I couldn’t help but let out an audible moan; I was losing control and the pleasure was too much for me to handle.
I started jacking off as the vibrator violently spasmed against my prostate. The pleasure was absolutely indescribable. Needless to say, I didn’t last very long, especially with the sexy porn I was watching with women pleasuring men the way I wanted… needed to be pleasured.
That’s when it hit me. I started bucking uncontrollably. I was moaning in pleasure. Ropes of cum were erupting out of my dick and I was making a huge mess. My whole body was shaking. I felt waves of pleasure everywhere, not just my dick. I was simultaneously blissfully unaware of my surroundings while also hyper aware of everything going on around me, especially the bed loudly squeaking while I was having the most intense orgasm I’ve ever experienced.
I lost track of time, but when I was done, I was the most relaxed I’d ever been. Ever since then, I regularly include prostate stimulation as part of my masturbating, and I one day hope to find a woman who’d be into prostate play with me.
Source: reddit.com/r/eroticliterature/comments/s4j7gm/playing_with_my_prostate_opens_up_a_new_world_of
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Well written. Hot. Original.