My knuckles were white on the controller. I’d just paused the video game I was playing with my buddy Silas, who was suddenly frowning at me. We’d been fighting our way through a castle all afternoon, battling computer-generated monsters, and were almost to the last threshold, the game’s ultimate level.

“What is it?” Silas asked.

I let out a tight breath and said, “I want to ask your advice.”

“You need to work your sword and shield together, man, I keep telling you that.”

“Not game advice.” I set down my controller. I’d been attempting to work up my nerve for hours. But I finally found myself blurting out, “I want to have anal sex with Sheila!”

He grinned and tossed aside his own controller. Silas was always happy to provide his carnal wisdom. He was ferociously adventurous and given to many sexual escapades. If there was a sex act I hadn’t experienced, I could rest assured Silas had been there, done that. At least twice.

“You and Sheila have been dating around three weeks, and you haven’t fucked her ass?” He sounded genuinely surprised. “Did she tell you no? If she did, bro, you’ve got to respect that.”

“I know that!” I snapped. “I haven’t asked yet.”

Silas steepled his fingers, like a psychiatrist dealing with a troubled patient, and countered, “Why do you want to do it?”

“Because, well, I’ve never done that with any woman.”

“You’re serious? You’ve never had ass sex with anybody?”

“I just said that.”

“You said with a woman.” Again, he grinned. “Let me tell you, an ass is an ass. If you wanted, we could.”

I knew he was mostly kidding, but I also knew if I asked, he’d gleefully let me fuck him. But I was “hopelessly straight,” as he put it, and turned him down.

“Fine. Rain check,” he said with a shrug. “What do you want to know? Technique? How to approach your girlfriend with the idea?”

I wanted it all, and said so. I confessed to obsessing some over the act. I craved setting my swollen cockhead to that cryptic backdoor entry, sliding slowly inside and feeling the exotic angle. I had wanted to sink my lubed cock into a chick’s asshole for some time. But to date, the women I’d propositioned had all, every one, put the immediate kibosh on that desire.

Silas just didn’t understand sexual inhibitions, though he, of course, respected them in others. Somehow, he’d always attracted people who were just as spirited and free as he was. In college, he’d bragged to me shamelessly about his sexploits, which hadn’t seemed to slow as he’d aged.

Anyhow, he talked me through the steps. Mostly it was common sense: Be sensitive to your partner, stay aware of even the least discomfort, go slowly, etc.

As for how to ask her, he said, “Look, you’ve got the right motivation, wanting to be intimate with her. Tell her that. Now, can we finish this game? I want to get to the final portal.”

That night I saw Sheila. We had a nice dinner out, then went back to her place. Sex was definitely on the dessert menu. She gave me that gleaming look, and my heart raced as my cock swelled. Sheila is smoking hot, and the sex we’d been having was so terrific I was almost tempted to say nothing about anal, in case it spoiled things between us.

But Silas’ instructions and pep talk were still bouncing around in my head. As we headed to her bedroom, though, she seemed a bit preoccupied. Instead of immediately undressing, she sat on the edge of the mattress and tugged me down next to her. She squeezed my hand and said, “I want to ask you something.”

“Anything.”

She paused, and I briefly had the awful idea she was about to break up with me. Then she said in a bashful voice, “Have you ever considered anal sex?”

My jaw dropped, and I said hoarsely, “God, yes, Sheila. All the time.”

“Really? Have you noticed how often I get on my hands and knees for you? I’ve been waiting, hoping, you’d make a move.”

She turned away, but I gently tilted her face back toward me. My heart was soaring. I laid my lips softly on hers, and then confessed, “I’ve wanted to do it so badly.”

She threw her arms around me, and we held each other tight for a moment. Then she stood, shedding her clothes.

“Fair warning,” she said. “I haven’t done it before.”

That wasn’t a problem for me. I hurriedly got out of my clothes. There was a quivering in my belly, and my hard cock was twitching. She lay back on the bed, and I joined her. Once again, we were in each other’s arms. We started to kiss, and our passion swiftly built. Her skin was so smooth, so enticing. I touched her heaving breasts, and she groped my ass, making me press my cock against her.

Pleasure was already sparkling through me, as it was for her — if I was properly interpreting the growing glint in her eyes. Our tongues tangled sensuously. She reached between us and clutched my shaft, squeezing it and giving it a few pumps. I stroked her pussy lips, even though we both knew I’d be seeking another entrance to her lovely body that night.

Finally, it felt like the right time. With an expectant but nervous look on her pretty face, she reached over to her bedside table. She took a tube of lube out of a drawer and handed it to me.

“Remember, it’s my first time,” she said.

I was beyond excited to be deflowering her, but I promised, “I’ll be gentle.” Then I admitted, “It’s my first time, too.”

My confession brought a sweet light to her eyes. And I knew it was, indeed, a very special night for both of us.

She got up on her hands and knees, facing toward the head of the bed. I thought of all the times I’d done her in that position, thinking she just really liked doggy-style. All the while, she’d been secretly waiting for me to penetrate her rear!

I gazed down on the glory of her ass. It was beautiful, like a sculpture. The gorgeous swells, the elegant curves. Those two lush, dimpled halves, separated by an alluring valley. And nestled there, the luscious ring — the portal I’d longed for.

“Can I lick you there?” I heard the words as though they were spoken by a stranger. Some powerful instinct had awoken within me, and I was overcome by the urge, the vast desire, to tongue her bunghole.

But I was also terrified that by voicing my sudden desire, I’d just ruined everything and inadvertently wiped out my chance to finally screw a woman’s ass.

Sheila turned to look at me over her shoulder. A devilish delight danced in her pretty eyes as she said, “You’re going to make all my dreams come true, aren’t you? Yes! Lick me! Tongue-fuck my asshole!”

Her obscenities only added to my excitement. I put my palms on the luscious hemispheres of her ass and gently spread them. She thrust her butt high in the air, to give me all the access I could want.

There was a term for this, I knew. Rimming. Rimjob. But as I put my mouth over her hole, all I could think was that my kinky secret fantasy was about to come true.

My tongue made contact. Sheila jumped, and so did I, with a quivery joy that made my cock dribble pre-come. I felt the crinkly texture of her crimped opening underneath my tongue tip. I swirled it in a circle, and Sheila moaned with raw pleasure.

I lapped sloppily at her pliant flesh. When her hole was slick with my spit, I dared to press forward with the stiffened the point of my tongue. Gradually, I coaxed her ring open slightly and ventured inside it.

“Oh!” she moaned. “Your tongue feels so good on my asshole! Lick me! Lick me hard!”

I could only penetrate so far, but every wriggle of my tongue brought a fresh grunt or growl from her. Her legs were shaking, and her body wriggled. I pushed my tongue as deeply as possible, spearing her deliciously snug backdoor.

“It’s making me — making me — ” she stammered, and then I felt her come hard, all from having her asshole licked. It felt miraculous, something so unexpected and wonderful.

Panting, I fell back, but I quickly recovered. I squirted out some lube and slickened up my cock. The moment had finally arrived. I set my cockhead to her spit-shiny ring. I rested it there, applying just the softest pressure and letting her truly get used to the idea of what was going to happen.

When I pushed a little way inside, she groaned. I watched for any signs of discomfort. There were none, so I eased in another centimeter. I was prepared to go into her incrementally.

But when I was maybe two inches inside, feeling the awesome grasp of her, she moaned loudly and rocked back hard. In an instant, I was all the way in with my cock buried to the hilt. I gaped at the beautiful sight.

“Now, fuck my ass!” she demanded.

I grabbed her around the waist, set my knees and stroked in and out of her. The first few motions were tentative, but she wanted it harder and faster — and wasn’t shy about asking for it.

I slammed my cock deep into her, and she took all of me. Our coupling was primal and amazing. It was like an animalistic excitement had gripped me in its fierce jaws. In no time, she went into another orgasmic fit, and I couldn’t hold off my own climax. Hot come spewed out of my dick and into her rear end. It was blissful and intense.

She fell to the mattress, and I collapsed with her. We lay together, still joined, cock to ass. I’d reached the ultimate level.