When I first approached Cassidy about being pegged, I was worried she was going to judge me. Not all women would be into using a dildo on their boyfriend’s ass, surely. However, she was totally on board, and we went that same weekend to go shopping. It thrilled me to look at all the toy and lube options. We really did have a whole new world to explore.
“What do you think?” she had said, at the sex toy shop. “This one looks like a good starting place, right?”
She held up a slim, smaller dildo. I nodded. “Yeah, I think it’s better to work my way up. Let’s get that one.”
However, the array of dildos was hard to pass up. We ended up coming home with a variety of toys in a variety of sizes.
That night, after an hour of a sensual massage and making out, I told Cassidy to grab the lube. I felt ready. I had been daydreaming about this for so long, and now it was happening.
“Just lay back,” she said comfortingly. “Like that.”
I was on my back this first time, so I could watch Cassidy as she first fucked me with a dildo. Her fingers pressed the lube into and around my asshole, and I sighed happily. Even that felt so good.
She put the slender, four-inch dildo at the entry of my ass and began to press it slowly inside, letting me get used to the intrusion. Immediately, I was in heaven. I held my legs apart and back to give her better access.
“How do you like that, baby?” she said, moaning as she started to fuck me in a slow, gentle rhythm. “Does that feel good?”
I bit my lip and looked into her beautiful blue eyes. “Fuck yes.”
I could hardly get the words out. As she used the dildo on my ass, I began to stroke my cock. It didn’t take long for me to shoot my load, between my own hand and the feeling of the toy inside my asshole.
A week later and I had quickly become a pro at taking the four-incher. Cassidy and I were watching a movie one night when I pulled her against me. “So I’m thinking the six-inch one tonight?”
Cassidy giggled and ran her hand along the crotch of my pants, where my cock was already twitching. “Oh absolutely.”
I had been dreaming about this all day, the feeling of that dildo sliding deep into my lubed ass, unlocking whole new sensations of pleasure. This six-inch toy was longer, yes, but also slightly thicker. I had a feeling it would drive me even crazier than the other one had.
I watched that night as Cassidy coated the dildo in lube. As I got into position on all fours, she raised her eyebrows at me.
“Are you sure you want it like that, David?”
I laughed. “Yes!”
It was true that being fucked in this position made the feeling a little more intense and gave most of the control to Cassidy, but I kind of liked it that way. I felt like I was ready for a little more intensity anyway.
“Shiiiit,” I moaned as Cassidy slipped the flesh-colored toy into my ass. It burned slightly, but I quickly got used to the difference in thickness. I felt so much fuller and stretched out. I couldn’t believe we still had two toys left to try. . .
I came very quickly that night, my eyes rolling back in my head as Cassidy started to thrust the dildo in and out of me as she rocked her hips. I loved how the dildo felt, but also how it felt having my girlfriend run her hands along my body as she fucked me.
We lay there afterward, collecting our breath and cuddling. After a few minutes, I was already getting hard again, and Cassidy slid over to ride my cock. I felt weak and sensitive, in the best way possible, after having just cum from having a dildo in my ass.
A few weeks after that, Cassidy was doing some cleaning and pulled out the eight-inch toy we had bought. She held it up, and I’ll admit it looked a little frightening.
“What do you think?” she said, grinning. “Are you up for the challenge?”
That Saturday, we decided to go for it, with me on my back and holding my legs back. Cassidy used extra lube this time and went very slowly. I even looked down and watched the toy disappear inside my asshole. It felt incredible like miniature orgasms were washing over my body. I could hardly control myself.
Cassidy kept the dildo inside me, unmoving, for a few minutes, as my body stretched around its size.
“Fuck me,” I panted, looking up at her, and she immediately obliged.
She went slowly but fully, withdrawing the dildo completely and sliding it back into the base. My head was spinning, my eyes seeing stars. I couldn’t believe I had worked up to a whole eight inches!
Cassidy grinned happily as she watched me cum, coating my stomach. She always said one of her favorite parts of using dildos on me was how much I clearly enjoyed it.
“You know you still have one left?” she said, as I pulled her in against me, her tits falling towards my face.
I moaned my acknowledgment as I began to suck on her nipples, Cassidy’s words tapering off into sighs. It was on my mind every time we fucked with the dildo, the fact that there was still one more toy to go. Ten inches though? That was no joke!
We picked a relaxed Saturday night where we had a lot of time to spend. We had bought more lube (since we had quickly run out) and laid down an extra towel on the bed. Cassidy squirted the lube onto her hand and got my hole nice and ready.
“Look at this thing!” she gasped, holding up the thick dildo. “Are you sure you want this, babe?”
I absolutely did.
I was impressed by the way I took all of that length and girth. Maybe my asshole was getting used to these dildos at this point, but either way, I was surprised. The dildo stretched me out to what felt like my capacity, without being too painful. If anything, the pleasure had reached an unthinkable level.
We changed positions a few times, moving from on my back to on my side to all fours, and every time, I thought I was going to cum right then and there. Cassidy couldn’t control her moans as she watched the toy disappear inside me. I could tell she was in disbelief too.
After about twenty minutes of alternating between slow, sensual fucking, and hard, pounding thrusts, I finally allowed myself to cum. It was my most intense orgasm yet, and I had to bite down on the pillow to avoid waking up the neighbors. Cassidy continued to thrust as I came, which was exactly what I needed.
When the pleasure and bliss had finally begun to subside, I rolled onto my back to catch my breath, staring up at the ceiling. Cassidy lay next to me, looking at me with a wide-eyed expression.
“You took ten inches!” she said, sounding delighted. “I’m not going to lie. It was super hot.”
I grinned at her. “Yeah, but it’s kind of sad, isn’t it? Like, what’s next?”
Cassidy sighed, falling against my chest. “I’m sure we’ll think of something.”
