It was my birthday, and I had been eagerly anticipating exploring anal sex with my girlfriend, a fantasy I had shared with her in the hope of making it a reality.

However, as the day approached, she confessed her reservations on the phone, citing discomfort and uncertainty about the act. "I'm sorry, but I just can't do it," she said, her voice filled with regret.

Although I was disappointed, I respected her choice.

At work the next day, Kelsey sensed the tension in my demeanor as we sat in the break room. "Everything okay?" she asked, her concern genuine.

"Not really," I sighed, deciding to confide in her. "My girlfriend and I had a fight. She backed out of trying anal on my birthday, which was what I was really looking forward to."

I mopped and sighed, being annoying, I know.

"Hey, you know what? Screw it. I'm tired of waiting for her to come around. Let's do this," Kelsey blurts out, her voice a mix of defiance and excitement as she looks at me across the dimly lit room.

I shift uncomfortably, my mind racing with a mix of guilt and curiosity. "Are you sure?"

Kelsey leans closer, her eyes locking onto mine. "Yes, I've been thinking about this for a while myself, and I want to try it. With you. It's the perfect opportunity to break our anal virginity," she says, her words hanging in the air like a dare.

The thought of having anal sex, something I've fantasized about but never experienced, sends a thrill through me. But the fact that it's with Kelsey, someone I work with and have developed feelings for, makes my stomach twist with guilt. "Okay, but we need to be careful. And gentle. It's both our first times," I respond, my resolve wavering.

She nods, her expression softening. "Of course. Let's take it slow. We can use plenty of lube," she suggests.

After work, we go to her apartment. She doesn't waste any time, and drags me to her bedroom and digs into her dresser drawer, pulling out a bottle of lube.

I watch as she pours a generous amount onto her fingers, her movements deliberate and focused. She glances up at me, a small smile playing on her lips. "Ready?" she asks, her voice barely above a whisper.

Nodding, I position myself behind her, my heart pounding in my chest. I lean forward, gently pressing the tip of my penis against her entrance. She gasps softly, her body tensing slightly. "It's okay, just relax," I murmur, trying to soothe her nerves.

Slowly, I push forward, feeling the resistance as her body adjusts to the intrusion. Her breath hitches, and I pause, giving her time to adjust. "Does it hurt?" I ask, concern lacing my voice.

"A little, but keep going," she replies, her voice strained. Encouraged, I continue, inch by inch, until I'm fully inside her. We both let out a sigh, a mixture of relief and discomfort.

"You good?" I inquire, hovering above her, my hands supporting my weight.

"Yeah, just give me a minute," she breathes, her body relaxing gradually.

As she settles, I begin to move, cautiously at first, then picking up speed as she moans softly. The sensation is unlike anything I've experienced before, intense and intimate. "Oh, god, this feels so good," Kelsey whispers, her voice filled with surprise and pleasure.

Encouraged by her reaction, I increase my pace, our bodies moving in sync. The room fills with the sound of our breathing and soft moans, the only other noise the squelching of lube as we move.

Just as things are reaching a peak, Kelsey tenses again, her fingers digging into the couch cushions. "Wait, it's starting to hurt again," she gasps, her face contorted with a mix of pain and pleasure.

I freeze, my mind racing. "Do you want me to stop?" I ask, my voice heavy with regret.

"No, just...use more lube," she manages, her voice shaky.

Quickly, I reach for the bottle, drizzling more over us both. "Better?" I inquire, watching as she nods, her expression easing slightly.

With renewed care, I resume, slower this time, ensuring each thrust is gentle yet deep. Kelsey's moans turn from pained to pleasure-filled, her body responding eagerly to my touch. "Yes, like that, don't stop," she urges, her voice breathless.

The intensity builds, our bodies slick with sweat, the room charged with our shared desire. As we near the precipice, Kelsey clutches at me, her body trembling with release. "I'm close, so close," she murmurs, her voice a plea.

Inspired by her urgency, I quicken my pace, my own climax nearing. "Me too," I groan, my voice rough with need.

With one final thrust, our bodies collapse together in a tangle of limbs and tangled sheets. Breathing heavily, I lie beside Kelsey, our hearts pounding in unison. "Wow," she whispers, her voice filled with awe.

"Yeah, wow," I echo, my mind reeling from the experience. Yet, amidst the haze of satisfaction, a shadow of guilt looms. "I just feel bad about my girlfriend," I confess, my voice heavy with remorse.

Kelsey turns to me, her expression understanding. "I know, but remember, this was about us exploring something new, just curiosity and a life experience," she assures me, her hand finding mine.

I nod, appreciating her perspective. "Thanks, Kels. For everything," I say, my gratitude genuine. We both are silent, as thoughts race in my head about wanting to have anal again...