When my boyfriend told me that he wanted to try anal sex, I immediately got to work researching the topic. I read every book I could find, scoured advice columns from my favorite magazines, and bought a few instructional videos. I even convinced my boyfriend to watch the videos with me.

Jeff wasn’t surprised by my obsessive research. I’ve never done anything without learning all I can about it first, and sex is no different. Luckily, Jeff understands my fetish for research.

I started training myself for anal penetration a couple weeks before letting Jeff enter my backdoor. I spent days with butt plugs pushed deep inside my ass, and I gradually increased the size until I felt ready to take an actual cock. I wore the largest butt plug for nearly two full days, even keeping it in at work and while out to dinner with friends. I was determined to be as prepared as possible so that the first anal experience Jeff and I shared would be perfect.

A few weeks after our initial conversation, Jeff and I went out for dinner. I was wearing my butt plug, but I didn’t let him know. I wanted to surprise him with it later that night. While we talked, he was careful not to ask about my anal research. I knew he was anxious to find out what I was up to and when he’d finally get a chance to penetrate my ass, but I wanted to make him wait. It wasn’t until we were in the car on the way back to his place that I told my boyfriend I was ready for the real thing, and he was definitely thrilled by the news.

We were both so excited that the drive home felt painfully long. I was glad we’d gone to a restaurant only ten minutes away and that Jeff is a bit of a speed demon, because we were at his house in no time, and then the real fun began.

As soon as we were inside, Jeff was tearing at my clothes, trying to undress me as fast as possible. He’d been so patient during the weeks leading up to that moment. It came as no surprise that he was suddenly unable to control himself.
Honestly, I was just as impatient, and I started undressing him just as quickly. We were down to our underwear before we stopped and moved to the bedroom, where we had lube and condoms, necessary supplies for what we had planned.
We climbed onto the bed and started fooling around again, grabbing and groping and kissing each other more before we finally got down to business. I slid Jeff’s boxers down and watched his hard cock spring upward. Next, he pulled off my panties, and that’s when he got a surprise. He still didn’t know I was wearing my butt plug, and when he saw the shiny red base nestled between my cheeks, he groaned.

“Oh, God,” he said. “Have you had that in all night? Even at the restaurant?” I nodded. “Shit, that’s hot!” he moaned.
I waited to see what he would do next. I expected him to remove my plug and replace it with his hard cock, but he had something else in mind. He grabbed a condom off the table, rolled it over his dick, and hovered over me for a moment before penetrating me. My pussy was dripping wet after spending all day aroused, and he slid into me with ease. With his dick in my pussy and the plug still lodged in my ass, I felt like I was stuffed full and ready to burst—and it felt good!

He pushed me flat back on the bed as he fucked me, and as he drove deeper with each stroke, I felt the shocks of pleasure all through my body. I pulled my knees up and planted my feet on the mattress so I could thrust up against him, and every time my butt hit the bed, it jostled the plug inside my ass. It was turning me on like nothing else, and I felt an orgasm quickly building. Jeff pumped furiously as I inched closer and closer to a climax, and when he sensed I was on the verge, he pushed in as deep as he could and held still. That was the last straw, and the pressure from his cock and the anal plug set me off.
I’d come faster than usual, so Jeff was still hard when he pulled out, and he was definitely ready to move on to the main act.

He moved off me so I could roll over onto my stomach, then he reached down, grabbed the base of my plug and slowly eased it out until it popped free. He turned and put the toy down on the nightstand and grabbed the tube of lubricant I’d bought for the occasion. I heard the snap as he flipped the cap open, and then I felt the drizzle of gel as he squeezed it onto my ass. He didn’t stop pouring it on until I felt it dripping down my crack, and then he began spreading it around, even pushing a fingertip into my ass to make sure the lube got inside, which was the most important thing.

By the time he was ready to enter me, my ass was as wet as it was going to get, and I was going crazy with anticipation. Jeff pulled me up at the waist so my ass was in the air, and I turned my head to watch as he guided his cockhead to my tight opening. The combination of pussy juice on his dick and the lube he’d applied to my ass helped him slide the tip in, but it still took a moment for my ass to open enough to take the rest of his shaft. He took his time, carefully pushing in inch by inch, and in a minute or two he was completely enveloped between my cheeks.

Even though I’d prepared with weeks of anal training and various butt plugs, having a real cock buried in my ass was an entirely new experience. It was so different from all the silicone toys I’d used for practice. It felt better, too. His cock filled my ass better than any of the toys had, and I noted every ridge as he pushed deeper and deeper. It was so thrilling that I was sure I would come at any moment, before any of the real action even started.

It felt even better when he began stroking in and out, and I immediately experienced tremors of pleasure. His thrusts were smooth and even, with each one more intense than the last. I’d known it would feel good, but I had no idea I would like it that much. Wow!

Each time Jeff’s cock slid out of me, leaving just the head between my cheeks, I moaned, loving the friction of his dick moving in my ass. I wanted to buck against him, to thrust as hard as I could. As excited as I was to have him penetrating my ass, though, I knew Jeff was just as thrilled, and I wanted to give him the chance to fuck me the way he wanted before I went wild and started doing whatever felt good.

Thankfully, we were on the same page, and the minute I started craving deeper, harder thrusts, he delivered. His cock pumped in and out of my butt at exactly the right speed and with the perfect amount of force, and soon it was impossible to control my own bucking and writhing.

I moved wildly beneath him, slamming my hips against him and forcing his cock to rocket in and out between my cheeks. Using my toys was fun, but this—this was incredible! My orgasm was building quickly. I was moaning loudly as I wiggled my ass, trying to get closer, to take Jeff deeper, when I finally reached my climax. I shrieked excitedly as my pussy spasmed and my ass clenched tightly around Jeff’s dick.

I was so hot that it felt like my entire body was on fire, and I loved it. I continued thrusting against my boyfriend as I came, and it wasn’t long before he reached his own thrilling climax. I felt his dick pulse as he came.

When Jeff rolled off me a minute later, his semi-soft dick slipping out of me, my ass felt empty, but I was completely sated. All the preparation and research hadn’t prepared me for how good it felt to have Jeff’s cock plundering my ass.

Now Jeff and I are anal experts, and it’s become a regular addition to our sexual repertoire. Next up is getting Jeff to try some of our anal toys on himself. I’ll be sure to share the story when it happens.

Ms. Alice T.,
Philadelphia, Pennsylvania