He Gets Off with His Butt Plug Whether He’s Alone or with His Girlfriend

I tend to be on the shy side, so even though I have a very dirty mind, lots of times the most sexual action I get is in my head, or from masturbating. So it was with my foray into butt play; I decided to order a medium-size black butt plug over the Internet, not wanting anyone to see me purchasing such an item. But I fantasized about wearing it out in public and having a beautiful woman tease me about what was up my ass.

But even at home, I was embarrassed as I browsed the many colors and sizes available. I’d had no idea that there were so many butt-plug options, which made me feel more comfortable, since that meant that there must be a lot of men and women out there with these kinds of desires. Even though I had porn videos that focused on anal pleasure, somehow being able to so easily buy a butt plug drove home the knowledge that anal play was a common activity. I’d known that intellectually, but I still felt unnerved about my purchase, which only added to my arousal.

I ordered my plug, then later jerked off as I pictured myself wearing it and then getting my ass licked and finger-fucked by a gorgeous woman. As it turned out, my fantasy wound up coming true sooner than I had expected, but first I got in a little solo practice.

My new toy arrived two nights later. I had been eagerly anticipating it all day, hardly able to sit still at work. When I opened the box, I did so reverently, my cock practically ready to blow at first sight. I had also purchased some lube to make the toy’s insertion easier and found that package in the box as well. I turned off the lights in my bedroom, save for a dim lamp in a far corner, and set out some candles, figuring that’s what I’d do if I had a girl over whom I wanted to seduce. I wanted enough light in the room to let me stare at my ass in the mirror but still keep the mood sexy. I put on some porn, featuring a man like me who gets fucked in the ass by a woman with a strap-on cock, then gets his ass licked by two pretty girls. The images before me already had my dick hard, and my ass was primed for action.

I started with my finger, lubing it up and then pressing it inside my back hole. This I had done before, but I had only ever gotten two fingers in, and the plug was wider than that. “Oh yes, fuck me,” I said aloud, preparing for the day when I would get to speak those words to a real, sexy woman. My ass clenched, then released, allowing me to enter farther. I still had my eyes on the TV screen, but I was mostly focused on the way my butt hole tightened around my invading fingers.

When I had determined that my ass was ready for more, I shifted so I could look behind myself into the mirror. I applied more lube to my hole before adding some to the pointed tip of the toy. The plug was shaped like a cone, with the base wider than the tip. Next I bent over, studying my reflection as I inserted the toy. Watching has always been part of my attraction to anal porn; there’s something powerful about seeing an object disappear into someone’s ass, be it male or female. I feel it’s dirty because on some level I know it’s taboo; I can talk to my pals at work about picking up a girl and banging her all night, but I don’t see myself ever giving them the details about bending over and fucking my own ass!

Then, with a few deep breaths, the entirety of the black plug was in my butt. I stood up and walked around, getting used to this unfamiliar sensation. I took a moment to pull on my favorite pair of jeans, and I was pleased to see that no one would be the wiser should I choose to wear the plug outdoors. Then I took my pants off and stroked my cock in front of the mirror as I felt the toy protruding from my anus. When I needed to come, though, I lay down on my stomach, reached behind myself, and twirled the plug around and around, before sliding it in and out of my ass. That felt even better than having it sit there, because I got to be penetrated again and again. “Yes, Renee, give me your huge cock,” I said, inserting the name of my favorite ex as I pictured her holding me down while a giant strap-on protruded from her waist.

That fantasy made me come. I was soon pumping out a huge load as my ass worked overtime, clenching the plug that I had buried deep within my hole. Already, I felt used to it, like I’d been using the toy to jerk off for years instead of hours, and I decided to look into possibly getting a larger plug. I spent about a month using the black toy in such a way on a daily basis, until I couldn’t masturbate without it. I’d heard about women getting addicted to their vibrators, but could I have become addicted to my butt plug? If so, I didn’t mind one bit.

Then I decided to take the next bold step and actually wear my plug to work. I knew that nobody could tell, but still, as I stepped into my office building that day—after a bumpy car ride that had me horny and needing to masturbate in the bathroom—I couldn’t help but feel the day was special. And it was, because that’s when I met Jessica. She stopped in to pitch an idea to my company toward the end of the day, and we wound up going for drinks afterward. As I perched on my barstool, I started getting aroused all over again. She was wearing a red dress with a plunging neckline that showed off her ample breasts, and she was flirting with me, touching my arm and leaning in close as we chatted.

She wound up putting the moves on me, saying, “Can I kiss you?” I would never be so forward with a woman, but I certainly wanted to kiss her, so I was glad she made the first move. Our lips met, her tongue lightly darting into my mouth, until I got too embarrassed to go further in public. “Take me home with you,” she insisted, and I did.

But once there, I wondered what Jessica would think once I took off my clothes and she discovered what else I was wearing. I tried to stall her as long as I could, sensually undressing her and treating her to a tongue bath, culminating with my head buried between her legs, the taste of her pussy on my tongue, and an orgasm that had her clutching my head so tightly I could feel her nails digging into my skin even after she let go.

But then my feisty new lover insisted on undressing me. “Jessica, I… there’s something I have to tell you.”

“Yes, Ken?” she asked softly, staring at me with adoring eyes.

“I’m wearing a butt plug. I’ve had it in all day. I like… being touched there,” I finished. I waited breathlessly, sure she was going to storm out.

But instead Jessica said, “Let me see!” She was practically squealing with delight, and I bent over for her, just as I had for so many women in my fantasies. “Oh, I like that one a lot,” she said. I wasn’t sure if she meant she’d had the same one up her ass or if she liked using them on men, but either way, I was thrilled. She started to press against the toy, then had me bend over the bed.

“Put your hands over your head,” she ordered me, and I did, sticking my ass a little higher in the air. “Where’s your lube?” she asked, and I pointed to the nightstand drawer.

She fished out the lube, then removed the plug and slickened me up. “I want to feel you for myself,” she said as she pressed two of her small fingers inside me. They felt different than when I had finger-fucked my backdoor. She started breathing more heavily, clueing me in that she was aroused, too. “Take it, you little bitch,” she said as she added a third finger and slapped my butt cheek.

“Oh, yes,” I murmured into the pillow I’d grabbed as I gave up my ass to her. I don’t know how many women are into male anal pleasure, but I was so glad I’d found one who was. She pulled out her fingers and then held open my ass cheeks, her thumbs stroking my puckered flesh.

“You ready, Ken?” she asked as she then held the toy against my opening.

Even though I’d worn the plug all day, I felt like a virgin again as she started to push it into my lubed-up ass. In a sense, I was, because Jessica was in charge, and I let her press the toy all the way into me, then twirl it around. “I want to take a picture—stay there!” she told me, then grabbed her digital camera from her purse and snapped a few photos. “I’m going to use this for my screen saver,” she said, and that idea made me want to touch my cock, but I wasn’t sure if that was permitted.

“Can I play with myself?” I asked. She had tacitly become my domme, and I wanted to make sure masturbation was allowed.

“Yes, I want you to come,” she said. I started to jerk off and got another surprise when Jessica pulled the plug out and began licking my asshole, her tongue delivering an entirely new sensation, one I couldn’t replicate solo. It was with her tongue buried in my ass that I came, my dream coming to fruition as my hot load landed all over my fist.

We took a shower together and talked about our previous anal experiences and our fantasies. Jessica had to leave town the next day, but she promised that when she returns she’ll bring some toys for me to test-drive. In the meantime, I will look into purchasing an even bigger butt plug—for practice, of course.

—Mr. Ken I., Minneapolis, Minnesota