Prologue

“Oh fuck...” Alena moaned as my mushroom head disappeared between her butt cheeks.

I could never get used to the sight of watching my cock entering a girl for the first time.

“Does it hurt?” I asked.

“No ... push in some more...” the nineteen-year-old college girl encouraged.

I compiled, gripping the redhead’s hip and thrusting slowly until my cock went in another half an inch. Then I stopped, letting her get used to my cock in her ass.

Spooning on our sides like this wasn’t ideal. It was harder to control my thrust. But it was the best position for first-time anal sex.

When I felt no resistance from her, I went in another half an inch, then another. I stopped whenever she tensed up, then continued on when she relaxed.

Until I finally bottomed out. It was unbelievably tight. Okay, not that unbelievable, since every girl’s ass was always tight, especially for the first time. Sometimes a little too tight, especially when her butt’s clenching my cock.

Though not unpleasant. It was the opposite of unpleasant. I supposed this was how a cock ring would feel like, with the ring moving down my shaft as I pushed deeper into her ass.

Except unlike a cock ring, her butt could clench. At the moment, it felt like my cock was going to break from getting squeezed too hard.

Has a cock ever break during anal sex? I had no idea. I hoped not. I didn’t even want to fuck Alena’s ass in the first place.

I was only doing this as a favor after all.

I tried to calm down before my anxiety took over. Having stupid thoughts like that ... was stupid. I took a moment to breathe. Despite me not wanting to do this in the first place, I might as well try to enjoy this.

I focused my thoughts on what I enjoyed about fucking a pretty girl like Alena. Alena was really hot. The ratio of guys wanting to fuck her and guys that actually fuck her was probably a few hundred to one. So I was the only lucky few that could fuck her. And the first to fuck her ass.

Staring into the back of her ginger hair, I tried to enjoy the sensation of feeling her slender back against my chest, her perky butt against my pelvis, and her slim legs against my thigh.

Most importantly, I focused on how pleasurable it was to be inside this peachy ass. My cock. In her ass.

I never liked thinking like this. It was rude. But for the moment, it seemed to help me get into the right mood.

“Good?” Lisbon asked.

The petite college girl sat cross-legged in front of Alena. I glanced at her naked body. Her modest breasts looked so perky. I’ve been wanting to touch them since she took off her bra.

I’m definitely in the right mood now.

“I feel ... very stretched,” Alena said.

Lisa giggled, her breasts bounced a little as her body shook. “That’s the whole idea.”

Even after seeing Lisa’s tits every day, it still made my heart flutter a little whenever I looked at her naked.

I took a deep breath and willed myself to focus on the girl in front of me. It wasn’t right to lust after another girl when my cock was already in her butt.

“Let me know when you’re ready,” I whispered into Alena’s ear.

“Give me a while to ... get used to it...” Alena panted. “It feels different from having a plug up my ass.”

“But much better right?” Lisa gave a salacious grin. She should know. Her ass was the first one I’d fucked.

“You weren’t kidding,” Alena said. “I feel like I’m going to come just from this.”

“Oh!” Lisa exclaimed. “You should try with a vibrator on your clit! It’s the best feeling in the world when you come with him in your ass.”

“Um...” I interjected quickly before they started getting funny ideas. “How about we take it one step at a time?”

Lisa giggled. “Well, you’re the expert.”

It still felt weird to be called an expert.

I was by no means an expert. Even after fucking some of the hottest college girls’ butts to the point where I’m starting to lose count, simply talking to girls alone still made me anxious.

I was a wimp. Though I did have good reasons for that.

But despite my wimpiness, I still somehow became known on campus as the ‘go-to guy’ to help girls enjoy a cock in their butts.