Pegging my crush 

Travis was the only customer who could make me smile most days. Being a barista meant seeing a lot of people on a daily basis, 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 like some of my coworkers did. They seemed to really know their favorites, as though they were friends and not customers. To me, those people were just that – customers.

Travis was different, though. We had such chemistry between us. He was so friendly and warm, in that approachable sort of way. He had kind eyes and messy brown hair that I always thought about pushing my fingers through. I had a full-on crush. We bantered in ways I never had with a customer before. I was devastated when I first noticed his wedding ring. I had always thought he was off-limits.

I kind of pulled back after that, not wanting to get involved with another woman’s husband. But one day, several weeks after I first noticed his wedding ring, I noticed it was gone. I tried not to panic at first. Maybe it wasn’t anything. Maybe he had. . . lost it or was getting it cleaned? 

Travis caught me noticing, though. He had just taken a to-go cup out of my hand and gave me a sad smile. “Ah, yes. I wondered if you’d seen. My wife and I are going to get divorced.”

I did the whole thing you’re supposed to do when people tell you they’re getting divorced. I acted sad, offered support, etc. Is it terrible that inside I was screaming with joy?

Things quickly escalated after that: from me making his favorite chai drink, to meeting up after my shift, to inviting him over to my place for the first time. I was nervous, because he was even hotter than normal outside of the coffee shop, but when we kissed, my nerves quickly melted. That was when he shared his secret with me. 

“Don’t get me wrong, I did love my wife,” he said, taking a sip from his wine glass. “But we didn’t always line up, sexually-speaking. I really wanted to be. . . pegged.” He hesitated and looked at me. “But she was never into it.”

I pulled my head away from where it rested on his shoulder and looked at him.  I’m sure my eyes were huge. “Really? Well, that sucks, especially if it’s something you’ve always wanted. I think it sounds like a lot of fun. . .” I trailed off, imagining it happening. 

Something stirred inside me that night, a dominant spark that I think I always had inside me. It was just now coming to the surface.

I could see Travis’s face shift when I said it. It seemed like he was excited about the possibility of finally getting to be pegged for the first time. I loved seeing that sparkle behind his deep brown eyes.

“I’ve got a little surprise,” I said, a week later, when he was back at my house. My heart was pounding in my chest. I had been waiting for this moment.

I pulled out the strap-on from my closet, relishing in the expression on Travis’s face as he set eyes on it. His lips slowly stretched into a smile. It turned me on, knowing how excited he was for this. 

“What do you think? Is this what you had in mind? I hope it is!” I asked him, dangling the six-inch fleshy dildo in front of him. It was pretty thick, but I had asked Travis for an estimate of what size he might like, and that’s what he had mentioned. I ran my hand up and down the dildo. 

Within minutes, we were making out and crashing onto my bed. Travis got onto his stomach, crawled in between my legs, and began eating my pussy. I tugged roughly at his hair, feeling like a new woman. I was a woman who was about to fuck her man with a dildo for the first time. The orgasm he gave me then was stronger than any other orgasm in recent memory. I think we were both so on edge with arousal. When he finally came up for air after making me cum, he smiled down at me with heavy-lidded eyes. He knew what was about to happen. 

“It’s your turn now,” I said, winking at him. 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. Travis 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,” Travis shuddered, my fingers caressing his asshole. I slid my finger in and out, preparing him. 

“You like that?” I asked, watching his face as I fingered him. 

“Fuck yes,” he answered, his jaw slack. 

“You ready for this cock?” I smirked at him, taking the dildo into my hand and dragging the thick head of it against his asshole.

Travis moaned and nodded. “So ready.”

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 mouth opening and closing. Low growls escaped his throat. I could tell he was enjoying this feeling, and so was I. I felt sexy and powerful, fucking my man with this toy. I looked down and watched it disappear inch by inch. 

Once the dildo was buried completely in his ass, I started thrusting in slow, gentle strokes. Every time I thrusted, his breathing got a little faster. He made noises I had never heard him make before, animalistic groans and grunts. All it did was fuel me. 

“How does that feel, baby?” I asked him, meeting his gaze. “You like that, don’t you? You like getting ass fucked by me?”

“Feels so fucking good,” Travis groaned, his eyes widening as they looked into mine. 

He was stroking his cock as I fucked his ass, moving in faster pumps 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 splashed onto his stomach. 

“What did you think?” I asked, crawling on top of him as my hair fell around my face.

“I think I want you to fuck my ass again and again.” 

A week later, I showed up at Travis’s house with an overnight bag in my hand. His ex-wife had officially moved out, and we were celebrating the best way we knew how. He knew I had bought a new dildo to try on him, but he didn’t know anything else about it.

When we were naked in his bed and I was finished riding his face, I told him to close his eyes. 

“Holy. Shit.”

His eyes grew two sizes bigger when he saw the eight-inch dildo. He had been stretching his ass with plugs over the last week, so I hoped he was ready.

“Oh, this is going to be fun,” Travis said, smiling widely at me as he got onto all fours.

I ran my hands across his ass, smacking it as I drizzled some lube down his crack.

“Let me watch you lube your asshole,” I said, as I got into the strap-on harness.

Travis fell forward so that he was face down, ass up and reached behind him to get his asshole nice and wet, coating it in a big squirt of lube. He shoved his fingers in and out, sighing happily as he did so.

When he was finally ready, I got behind him, held onto his sides, and began to press the head of the dildo into his shiny asshole. I knew this all-fours position would be intense for him, but I wasn’t expecting such a strong reaction. He cried out louder than I had ever heard him, arching his back and tossing his head back. It was like he had unleashed some sort of animal inside him, and he was losing control and howling at the moon. 

Finally, I was completely inside him, and  I began to thrust my hips back and forth, allowing the cock to go in even deeper. I loved how his asshole stretched around the toy. Watching that was my favorite part.

“Fuck, that feels amazing,” Travis groaned, as his fingers gripped the sheets. 

“Mmm, you’re taking it so well.”

I couldn’t believe my own ears. The shy part of me was long gone. I felt powerful, naughty, and connected to Travis more than I had thought possible from those days in the coffee shop.

I held onto his ass as I started to pound him a little harder. When his hole was nicely-stretched, I pulled out almost all the way, before shoving the dildo back in, in one quick thrust. Travis fell forward onto the pillows, screaming with pleasure into them.  

“You love when I fuck you like this, huh?” I said, looking down to watch the dildo pound his ass.

“Yesssss,” Travis moaned. “Fuck yes.” 

He sat back up and started rocking back and forth then, and I stopped thrusting, letting him do all the work. It was hot as hell to watch him fuck this toy while listening to the wet lube sounds mingled with his sexy cries. 

“Oh shit, I’m gonna cum!” he screamed, and I watched in delight as he fell forward once again, cumming all over the towel we had put down. 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 pulled me into the crook of his shoulder. I looked down at his wet, softening cock, drops of cum glistening on the tip.

“You love fucking me, don’t you?” he asked, mumbling against my hair.

“Oh, I do. I really do.” I closed my eyes and smiled, thinking about the toys I had lined up next. . .