Skip to main content

Dildo Ass Play: How I Worked Him Up to a Bigger Size 

dildo ass play

I love when men are open to dildo ass play! 

A nymphomaniac like me needs constant sexual contact. That’s what made Brian my current favorite lover. He was the kind of guy who could fuck for hours and I never even had to ask him to lick my asshole. Even after having just come home from the gym and a very sweaty workout.  That’s my kind of lover. And best of all, he was open to receiving dildo ass play! Not many guys are open to this kind of thing, so I really loved that about him. 

We were hanging out on Sunday afternoon, watching TV and killing time before he had to leave for a three week business trip. I knew I would be able to get cock whenever I wanted while Brian was gone, but I just loved my current relationship with him. It was practically non-stop fucking, unless we were at work or sleeping. My new favorite sexual activity with him was dildo ass play. He was so hesitant at first but eventually, he opened up… so to speak. 

Brian sat next to me but was texting on his phone. I knew he was texting his business associates and firming up all of his travel details, but I found it boring. He should have been giving me all his attention since he was getting ready to take his cock away from me for three whole weeks. 

There was only one thing to do. Demand his attention. 

I slowly reached my hand over to his lap and let it rest right next to his inner thigh for a minute. It took him a few short seconds to notice. He glanced up at me, smiled, kissed my cheek and went back to texting. I let my fingers slide across his lap and felt his limp cock. Even at its limp state, it was still so impressively long and thick. I gave it a squeeze and held onto it firmly. Within seconds, it grew in my fist. He had no idea I had dildo ass play on my mind, but he would soon enough. 

“Oh, baby… that feels good.” he whispered in his husky voice. I pressed my tit against his arm and kissed his neck. That’s all it took! He lifted me and placed me on my back on the sofa, and in one swoop, my yoga pants were off. I wasn’t wearing any panties, of course, so my lovely pink pussy was on full display for him. I took my fingers and spread the pussy lips apart so that he could gaze at my puffy little clit. He knew what I wanted.  

He pushed his face against my cunt and bobbed his head up and down as he ate me like a starving man. His tongue danced around my clit as his finger slid into my pussy hole. He fucked me with his fingers and hooked them inside me, just as I liked it. I orgasmed in less than a minute. He knew this because of my primal scream.  

He stood up and began to undress quickly. I knew he was ready to fuck me. But… hold on a second. 

“Can I get Charlie?”  I asked, eagerly.  

He hesitated. Charlie is my smallest dildo. It’s only 5 inches long but it has a very nice curve to it and it’s not too thick. I learned quickly that it was the perfect toy for Brian’s introduction into dildo ass play. He hesitated at first and it was challenging to get him to relax and take it in, but he was a good sport and wanted so badly to please me that he played along and eventually would lay helplessly while I knelt over him and rammed Charlie up his asshole. I know it turned me on way more than it did him, but that’s the point, right? 

“Do we have to get Charlie today, babe?” he asked tentatively. “Can’t you just finger my ass a little?”

“I can do both!” I said, walking quickly into my bedroom to grab Charlie. He was in my sex toy drawer, right on top, currently the most popular guy of the bunch. I imagined all the other dildos, Fred, Jack, Herb… all grumbling whenever Charlie left the drawer, wondering when the fuck it would be their turn! 

I held Charlie in my fist and approached Brian with a big devilish smile on my face. It was my “You are mine now!” face.  

“Lube?” Brian sounded almost panicky. Despite wanting to please me, dildo ass play still made him a bit nervous. 

“YES, lube of course lube!” I ran back and grabbed the anal desensitizing gel.  A must for ramming tight assholes with sex toys. I doubt Brian would let me get close to his bum without this stuff.  

“Get on your stomach and spread your ass for me, baby.” I demanded.  

He did just that. I rubbed a generous amount of anal gel onto his brown opening. I knew we had to wait a few minutes for the asshole to get numb enough and I just hoped I could be that patient. Then, I spread some of the gel on Charlie to get him ready too.  “Another big day for you, Charlie…” I thought to myself and chuckled at my wit.    

Finally, we were ready to get on to the dildo ass play I had been eagerly awaiting. “Are you ready, lover?” I purred gently, looking down at Brian’s vulnerable hole and noticed that it was puckering. He was nervous, isn’t that cute? He only replied with “Mmmm hmmm” and when he felt Charlie’s head about ready to dive into the deep end, he clenched his ass, cock blocking me and said “Go SLOW!” 

“Yes, yes, baby, always!” I positioned Charlie again and drove him in, slowly but firmly until almost half of him was inside the abyss. Brian groaned but I couldn’t tell if it was mostly pleasure or pain. I continued to push until Charlie was almost completely inside. “How does that feel, Brian?” 

“GOD!” he yelled.  He squirmed around a little before he yelled, “Fuck my ass! Fuck it!” I complied, of course. Charlie was sent into a plowing frenzy.  I pushed in and out, over and over as Brian groaned and moved his hips around, grinding his asshole against Charlie. What a slut! He loved getting ass fucked after all.  

Suddenly, Brian raised himself up so that he was now on all fours, supporting himself by placing one hand on the arm of the couch and reaching out to grab his dick with the other. 

He jerked himself rapidly, grunting and panting, loving this dildo ass play. 

While Charlie continued to violate his butt, Brian orgasmed right into my new throw pillow. I was mildly annoyed. But it was worth it to see him enjoying the ramming session with Charlie and me. He hung his head, completely spent from all of this exertion and then collapsed on his stomach again. He must have thought it was all over for the night, bless his heart. I placed Charlie on the coffee table and told Brian to turn over. He obediently rolled over on his back and I squatted over his face, carefully lowering my ass right into his lips. “Eat my ass!” I commanded. He obeyed, of course. 

As he did so, I fingered my pussy until I came hard for the second time that hour. Now I would allow Brian to have a little break before I got to enjoy his cock again. I did have to give him time to reboot, after all.  

Brian was in the shower when I came up with a plan to take this dildo ass play to the next level. I grabbed a gift bag that I had lying around in my closet and packed the anal desensitizing gel along with another BIG surprise for Brian. Then, I hid it at the bottom of his suitcase and danced an excited little dance. I could not wait until he found it while unpacking in his hotel.  

He facetimed me about an hour after he landed. I smiled wickedly into the camera phone. “Hey babe, did you find your surprise package?” He just stared at me, open mouthed and shook his head. I saw him reach into the bag next to him and began to rummage around. He picked up my surprise and held it in front of him. 

“What the hell?” he asked. 

“It’s Goliath!” I explained, matter of factly.  

He stared at my prized dildo, the big boy of the bunch, the legend among my sex toys, Goliath and all ten glorious inches of him. He scoffed and stared at me. “What am I supposed to do with Goliath?” he asked, almost meekly. I think he knew the answer. It was time to upgrade his dildo by 5 inches. It was a lot, but I knew he could handle it. 

“I packed the anal gel, babe. You’re all set,” I answered. Brian was speechless and I watched him as he stared at Goliath, turning him over in his hand in disbelief.  

“Get ready, babe. I’ll wait.” I said. My words were so direct and firm that I knew there was no way Brian would refuse.  

He got ready quickly. I think he wanted to just get it over with. My pussy twitched with delight as I watched him undress, preparing for his ultimate dildo ass play session. He applied the anal gel and stared at Goliath nervously while we waited for the anal gel to kick in. After a couple of minutes, I impatiently said, “Get going, babe. I want to see you take my boy ALL the way!”

“All the way, are you fucking crazy?” he burst out. I just laughed. I had no doubt he would take him and like him. Even if Brian didn’t know it yet. He would love this new level of dildo ass play. 

I smiled and nodded my head. “Come on babe.” I think Brian knew I was not the girl he wanted to disappoint.  He never had this much sex with as hot a girl as I am so I knew he basically lived in the palm of my hand. 

“Do it.” I whispered. 

Despite my confidence, my jaw dropped in astonishment as Brian lay on his back, brought his knees up to his chest, giving me full view of his vulnerable asshole and began to tap Goliath’s head against his ass. I put my hand over my mouth to force myself silent. I knew Brian needed to just focus on the task at hand. My heart begin to pound loudly in my chest as my sneaky little plan to upgrade Brian’s dildo ass play unfolded in front of me. 

Brian was hyperventilating a little and I watched his hands tremble as he proceeded to give in to this more intimidating dildo. It seemed like forever but finally, Goliath was inside. One tortuous inch at a time, Brian pushed gently until Goliath was halfway inside of him. “Oh my god!” Brian cried out as he pushed even further. He was sweating now, I could see it clearly.  Even his chest and forearms were glistening with sweat. He was really laboring hard for me.  

“Go, Brian!” I shouted when I saw he was stalling. “Fuck that asshole for me NOW!”

Brian continued to work the dildo further and further into his tight hole. 

He cried out sounding like a wounded animal as a few more inches of Goliath tore into his brown hole. He paused for just a second, then like a trooper he pushed further. I kept encouraging him, like a high school coach, loudly and firmly. “You can do it, Brian. Don’t give up now! You almost have all of him inside you! Focus! Do it! Don’t let us down!”  

I didn’t realize that I was standing now, bouncing my legs up and down, willing him to take Goliath all the way. My heart was pounding, my body was shaking and only then did I realize I wasn’t even recording this amazing dildo ass play, damn it! Why didn’t I think of it?

“There!” Brian shouted as he spread his legs farther apart for me, to show me the glorious sight of his tight little asshole with a huge 10 inch dick stuffed deep inside of him.  

“Does it feel good, baby?” I practically screeched. 

“What the fuck do you think?” he shouted back, his chest heaving up and down.  

“Stay right there,” I commanded, “Don’t take it out and do not move!”  I heard him groan.  I ripped off my panties and began to rub my pussy. Watching him shove that dildo up his ass got me so drenched, that I had to stop rubbing and wiped my hand on my sheets before I was able to continue. 

It didn’t take very long to come after watching that dildo ass play! 

“Oh my god, you look so good with Goliath stuffed inside of you. The next time I have him in my pussy I’m going to cum so hard thinking about you!” I frantically rubbed my clit hard, with my eyes never leaving Brian and Goliath and had one of the hardest orgasms I’ve had in a very long time. I stood there, breathing hard, shoulders slightly hunched forward, suddenly thirsty. I grabbed my water bottle, took a huge drink and stared at Brian a little while longer.

“Can I please take him out?”  he asked timidly. 

I allowed it, of course, but I made sure he did it very slowly both for his sake and my own deviant pleasure. He was such a good boyfriend, putting his ass on the line like that just for my delight. Every girl should have a lover just like him, willing to perform dildo ass play on demand. 

As I lay in bed that night, I wondered what other sex toys I could present to Brian and exactly how much he would be able to take. We would soon find out! 

Ready to have some fun with a Phone Sex Goddess? Call me, Cassia, for a fun time! Are you new to ass play? I’ll help you guide you, baby!

Cassia