Ever since Jimmy first taught me the joys of anal penetration, I’ve been unable to get enough. Though I had always wondered what it would feel like to have a thick dick in my tight anus, I had never trusted any of my boyfriends enough to allow them to try it, until Jimmy came along. After the first time he invaded my ass with his stiff prick, it was all I could think about and all I wanted when we were in the bedroom. That was four years ago, and my asshole is still always hungry for hard cock or a suitable substitute.
That’s where my butt plug comes in. When Jimmy bought it for me, I thought he was crazy. Sure, I loved being anally penetrated by his cock, but a silicone toy? It didn’t seem like it would have the same effect. Boy, was I wrong! Now I can’t live without my favorite toy, or as Jimmy and I call it, “Big Red.”
Last week, as we were getting ready to leave for a long weekend at our cabin, Jimmy decided that we should have some fun. He told me to assume the position, and I immediately perked up. I knew from his words that he was going to bring out Big Red and fill my ass, and I couldn’t wait! Then Jimmy disappeared up the stairs to gather the necessary provisions.
Footsteps sounded on the stairway, and I slipped my panties down my legs and bent over the arm of the couch as Jimmy returned from the bedroom with our favorite toy and a bottle of lube. I flipped up my short skirt and wiggled my ass at Jimmy as he approached. I was growing impatient as I waited for him to slide the thick red anal plug into my behind, and I wasn’t sure if I could hold out any longer. I needed my ass to be filled with something—and soon.
Just when I was starting to think that Jimmy was teasing me and was going to make me wait until we reached the cabin before giving me the satisfaction I craved, I felt his hands on my butt cheeks. He gently massaged the round globes of my ass before lightly smacking my bottom, letting me know he was ready to start the fun. A moment later I felt the cool, slick lube hit my skin, with Jimmy’s finger following and rubbing the liquid in and around my asshole. He then started wiggling his finger inside my ass, loosening my sphincter for the larger object that was about to pass through it.
As soon as Jimmy thought I was ready, he applied some lube to Big Red, and then the tip of the toy nudged my rear hole. Slowly, Jimmy pushed the slick toy into my ass. It’s about five inches long and an inch and a half wide. Starting off with a slender, rounded tip, Big Red bulges out in the center before tapering off at the base. The design makes it easy to slide in and out, and it really fills me up. As the plug slid carefully into my ass, I moaned in pleasure. Jimmy was taking too long to get the toy inside me, and I wiggled my hips, trying to get it to go deeper.
Once the toy was all the way inside my nether hole and the wide base pushed firmly against my ass cheeks, Jimmy gave it a hard twist. I moaned even louder than before and asked him to do it again, but he refused. He smacked my bottom once and told me to pull up my panties.
“I know you would never want to leave home without your favorite toy,” he said, “so we’re bringing it along with us this weekend. But there’s one condition.”
I could guess what he was about to say.
“If you want to bring your toy on our vacation,” he continued, “you have to carry it in your ass.”
That was exactly what I wanted, and Jimmy knew it. I couldn’t contain the joy I felt at that moment. If I hadn’t already been sporting a huge smile, I sure was after hearing Jimmy’s “condition” for bringing my toy along with us. I wrapped my arms around my boyfriend and kissed him fiercely. He had just made my day.
Walking out to the car, I kept smiling, feeling the hard silicone rubbing against the inside of my rectum with every step I took. When our next-door neighbor came outside to see us off, I felt deliciously wicked. What would Margaret think if she knew my secret? I grinned at the thought and waved good-bye to her as Jimmy pulled out of the driveway.
As we got on our way, the feelings of pleasure grew more intense. Every bump we hit caused the toy to move around within my asshole, creating a series of heavenly sensations. I felt like I was moaning continuously for the fifteen minutes it took for us to reach the on-ramp for the interstate.
I begged Jimmy to avoid the highway, which was newly paved and would provide none of the same joys, but he said I had to wait for my pleasure. For the next hour, I concentrated on the full feeling I got from having the plug lodged deep in my ass. That was enough to get me hot and bothered, but when I started thinking about all the fun Jimmy and I could have with Big Red that weekend, it got to be too much for me.
Suddenly unable to control myself, I reclined my seat, lifted my skirt, and reached inside my panties, finding my clit. I started rubbing the hard nub, getting hotter as I did so. Then I wiggled my ass on the seat, causing the toy to rub against my rectal walls, and I slipped a finger into my moist pussy. The pleasure I got from the dual penetration was unbelievable. I was moaning and sighing loudly, rocking my hips while I plunged my finger in and out of my hot slit.
Jimmy chuckled as I pleasured myself inches away from him. Wanting to participate and not merely be an observer, Jimmy reached between my legs and found the base of Big Red through my panties. He gripped the silicone rectangle and started wiggling it back and forth. When I raised my hips, Jimmy tugged on the toy’s base, and my sphincter allowed two glorious inches to slip out of my asshole. The moment I bucked back against his hand, the toy was forced back inside me, and I let out a loud moan.
Jimmy continued wiggling Big Red inside my rear while I kept playing with my pussy, alternating between rubbing my clit and sliding my finger up inside my slit. I was soon climaxing, feeling my juices coat my hand and thighs. I moaned and sighed, and Jimmy continued jerking the toy in and out of my ass long after I had pulled my hand from my panties and my climax had subsided.
As I recovered, Jimmy pulled his hand away, telling me that the fun wasn’t over yet. I thought he meant that the weekend was just starting, but as he pulled onto the private road to our cabin, I knew I had misunderstood. Our cabin in the woods is in a rural area. The road to the house has never been paved, and it’s at least ten miles from the main road to our hidden getaway.
As we started down the final stretch to our vacation home, the impact of every hole and every bump was magnified by the silicone toy getting jostled in my ass. The sensations were incredible! With each new bump in the road, I moaned in pleasure. Before we’d gotten a mile into the woods, I was coming again at full force. My anal plug on its own had never provided so much extraordinary pleasure as it did during that trip.
I came at least three times before we got to the cabin, merely from bouncing around in the passenger’s seat of our SUV. I was entirely spent by the time we pulled into our driveway. I never imagined that my favorite anal plug could turn me on any more than it already had, but I was proven wrong. As Jimmy stopped the car in front of the cabin, he asked if I’d enjoyed the drive. As I nodded enthusiastically, Jimmy started speaking again.
“You know, I think we may need to make a few trips into town while we’re here,” he said. “Perhaps, if you’re good, I’ll let you bring Big Red along for the ride.”
—Ms. Hallie K., Las Cruces, New Mexico