Aaron was the only customer who could get a consistent smile out of me. Being a barista meant seeing a lot of people every day, especially repeat customers. For the most part, I was my typical shy self at work. I was friendly, but I didn’t go above and beyond to make conversation with the customers, like some of my coworkers, did. They even changed my nametag for April Fool’s Day to say “Shyenne” instead of “Cheyenne.”
Aaron was different, though. We had a natural flirtatiousness between us. He was so friendly and warm, with eyes that crinkled at the edges every time he smiled. His brown hair was always disheveled and messy, but it suited him and made him so approachable. I was devastated when I first noticed his wedding ring. I had always thought he was off-limits.
Until now.
Things quickly escalated from me making him his usual coffee order, to meeting up after my shift, to inviting him over to my place for the first time. We spent that first evening making out on the couch before he finally shared his secret with me.
“Don’t get me wrong, I love my wife,” he said, taking a sip from his glass. “But she isn’t into what I’m into. I’ve always wanted to be pegged, but she refuses.”
I pulled my head away from where it lay on his shoulder and looked at him.
“Really? Well, that sucks, especially if it’s something you’ve always wanted. I think it sounds like a lot of fun. . .”
I could see a shift in Aaron when I said that, a glimmer of excitement sparked in his eyes. After that, it was on.
“I’ve got a little surprise,” I said, a week later, when he was back at my house.
I pulled out the strap-on from my dresser drawer, relishing in the expression on Aaron’s face as he stared at it. His eyebrows shot up to the sky, and his mouth stretched slowly into a smile.
“What do you think? Is this what you had in mind?” I asked him, dangling the six-inch flesh-colored dildo in front of him. It was pretty thick and looked intimidating, especially for a novice.
Within minutes, we were naked in my bed. Aaron crawled in between my legs and began eating my pussy. I shook and trembled as he played with my clit, sliding his fingers inside me at the same time. The orgasm he gave me was more intense than any other orgasm I had had in recent memory.
“It’s your turn now,” I said, giving Aaron a mischievous smile. The fun was really about to begin.
We decided to start with him on his back. I put on the strap on and grabbed the bottle of lube from my nightstand. Aaron was wide-eyed as he watched me lube up the dildo, before taking the bottle and adding the lube to his ass as well.
“Fuck,” Aaron shuddered, my fingers caressing his asshole.
“Are you ready?” I asked, dragging the head of the dildo over his ass.
“Fuck yes,” he answered.
I slowly started to push my way inside him. His reaction was a huge turn-on for me. I watched his face tense up, his jaw falling open. Low growls escaped his throat, and I could see how much he was enjoying this.
Once the dildo was buried completely in his ass, I started thrusting in slow, gentle strokes.
“How does that feel, baby?” I asked him, meeting his gaze. I couldn’t believe this married man was in my bed, getting fucked by me. I felt powerful and so naughty.
“Feels so fucking good,” Aaron moaned back, his breathing growing fast.
He was stroking his cock as I fucked his ass, moving in faster thrusts now. He didn’t last long once I started to pick up the pace, and his cum quickly shot out in thick white ropes that covered his hand and his stomach. It was sexy watching him come undone and become a shaking, moaning mess.
“What did you think?” I asked, crawling up the bed so I could kiss him.
He let out a loud laugh. “Are you kidding? That was incredible.”
“Was it everything you hoped for?”
“Even more than that.”
A week later, Aaron was back at my place. We had been sexting all week about me pegging him again. It wasn’t easy for him to make excuses to his wife about where he was going, but he was hooked. We still had so much more to explore.
On that night, we decided to try it from behind. I knew it would be intense for him, but I wasn’t expecting such a strong reaction.
I started slowly at first, while Aaron was on all fours. I used plenty of lube and watched as the thick head of the dildo disappeared into his ass. That part was always so hot to me. Then, I began to thrust my hips back and forth, allowing the toy to go in even deeper.
“Fuck, that feels amazing,” Aaron groaned, as he threw his head back. I loved knowing how much I was turning him on, how I was doing something his wife could never do for him.
I held onto his ass as I started to pound him a little harder. I slid out from his ass nearly all the way, before shoving the dildo back in, in one quick thrust. Aaron couldn’t hold himself up anymore and fell forward so he was screaming into the blankets, his fingers frantically twisting them up.
“You love when I fuck you like this, huh?” I said, looking down to watch the dildo pound his ass.
“Yesssss,” Aaron moaned, as he lifted himself back up to all fours, looking back over his shoulder at me.
He started rocking back and forth then, and I stopped thrusting, letting him do all the work. It was so hot to watch him fuck this toy while listening to the wet lube sounds mingled with his moans.
“Oh shit, I’m gonna cum, I’m gonna cum!” he cried out, and I watched in delight as he fell forward once again, screaming against my pillow. I kept the dildo inside him, all the way to the base, as he came.
When I finally pulled out of him, he grabbed me and wrapped me up in a hug.
“You’re amazing,” he said, sighing.
I dragged my nails lazily against his chest and settled into his shoulder.
“So what do you think about next week?”
“I think next week would work great. She’s out of town at a wedding.”
I closed my eyes, smiling to myself as I thought about the 8-inch dildo I had waiting as a surprise. . .
