I was twenty when I had sex for the first time.

I’d been overweight and insecure in high school, so I graduated without ever having a girlfriend. The extent of my sexual experience was a peck on the lips from my prom date that I’m pretty sure was more out of pity than anything else.

After I graduated, I opted not to go off to school immediately. Instead, I lived at home, enrolled in community college, and started working the front desk at a tattoo shop close to my parents’ house.

Looking back, I was a little pathetic during those first months, not doing much except eating fast food and playing videogames when I wasn’t at school or working.

A few of the guys I worked with at the shop eventually took me under their wing, and that changed everything. I started lifting weights and doing CrossFit with them, ate better, and within a year or so I was physically a different person. The guy in the mirror was tall and athletic-looking, with broad shoulders.

Once the fat had melted away, I discovered I wasn’t a bad-looking dude. I still felt like that insecure chubby kid, though, so despite all the attention I started to get from women, I was too shy to pursue anything.

She dropped to her knees in front of me, slid her tongue up and down my dick, then wrapped her lips around it.

The owner of the tattoo shop was a badass biker chick, in her late thirties, who radiated the kind of sexual energy that younger women couldn’t hold a candle to. She was so sexy and sure of herself that I got nervous around her and shut down. I thought she might be flirting with me, but since she seemed to flirt with everyone, I tried not to read much into it. Still, she became the focus of my fantasies when I got home at night, and I figured that would be the extent of it. Because guys like me don’t get women like that — or at least that’s what I thought.

One night when I was closing the shop she stayed behind, and as I finished with the register she came over to the counter, leaned across it, looked me dead in the eye and said, “So are you not into older women or what?”

I blinked dumbly at her, not sure what to say. “What do you mean?” I eventually stuttered.

“I want you. I think I’ve made it pretty clear, but you seem oblivious, so I thought I would spell it out before moving on. You don’t seem to be into the giggling younger chicks who hang around here staring at you, so I thought maybe…”

Though I choked out a laugh, my dick had sprung to attention. I tried to play it cool.

“I wouldn’t say I’m into older women. I’m into a woman who’s older than me, though.”

She smirked as she realized my meaning and reached out her hand. I took it, following her back to one of the piercing rooms, marveling at my luck. Was this really happening?

She didn’t even hesitate once she closed the door, pushing me back against it and kissing me hard. She was such an erotic combination of strength and softness. She was tiny in my arms, but totally in control. We kissed feverishly for a few minutes before I felt her undoing my belt and lowering my pants and underwear.

Feeling her tight, hot pussy wrapped around my cock nearly drove me over the edge.

She dropped to her knees in front of me, slid her tongue up and down the length of my dick, then wrapped her lips around it. I had spent so many years wondering what this would feel like and had never come close. The warm, wet heat of her mouth drove me wild as her head bobbed up and down. When I felt her throat squeezing around my cock, I thought about how lucky I was to get my first head from a woman who knew what she was doing.

I wanted her to keep going, but I was scared I wouldn’t last much longer, so I gently pulled her head back to stop her. I could have tried to play it off, but it seemed better to just be honest.

“This is my first time,” I said. “I’m not gonna last long enough to make it happen if you keep doing that.”

I thought she might tease me about being a virgin, but she kissed me deeply again and said, “I’m honored.”

In a matter of moments, we had stripped each other of our clothes and I laid her back on the procedure chair. I tried to go down on her, wanting to make it good for her first, even though I had no idea what I was doing. But she stopped me.

“Later,” she whispered. “There will be time for more firsts later. Right now I just want you to fuck me and not worry about anything but enjoying it.”

I lined my dick up with her pussy, which felt slick and ready. I started to slide it in, then paused to enjoy the feel of her wet entrance squeezing around me. She rolled her hips impatiently, so I drove it the rest of the way in. Feeling her tight, hot pussy wrapped around my cock nearly drove me over the edge, but I managed to hold on for a few minutes of hard thrusting before I lost control and came.

It was worth the wait. She was gorgeous and down for anything. Over the next few months, she made a game of introducing me to as many new sexual experiences as she could — and there were a lot. The first time making her come with my dick inside her, first time in the shower, first road head, first threesome, first anal…the list went on. But that very first time will always be something special.

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