I Popped My Fuck Buddy’s Anal Cherry – and He LIKED It!

So. My newest fuck buddy has been harping incessantly about the joys of anal sex, and how I should let him have my anal cherry. Now, this boy toy is new and doesn’t realize that the more he whines at me about it, the more likely it is that he’s never going to get his chance to slide his dick into that mesmerizing, soft, tender pink little hole of mine. The more he talks, the less i want to give in, and the more my naughty mind wonders how to get back at him for tormenting me about it.

Bedtime came around about a week ago, and I could tell he was preparing to broach the subject again. (The quick shower, close shave, and ASTROGLIDE next to the bed sorta gave it away…) I looked at him, batting my eyelashes innocently. I smiled, and whispered, VERY softly, “Do you want to fuck my sweet little asshole, baby?” Before he could answer, I pulled him close and whispered into his ear. “Tell you what… I’ll make a deal with you. YOU can have that hot little ass every night for the rest of your life on ONE condition…”

“The condition is that I get to fuck YOUR ass… FIRST.”

I would have given ANYTHING right then for a camera, to capture the stunned look on his face. He actually BLUSHED! And then stammered out, “I.. I’m not.. GAY!” I chuckled softly and almost felt sorry for him, then… almost. I said to him, “A GIRL fucking your ass does not make you gay, stupid.” He looked at me as if I’d lost my mind, and I shrugged and sighed in mock frustration. “Hey, if you don’t want to fuck my ass….”  I hopped into my bed wearing nothing but an evil smirk and curled up on my side, eyes closed.

He went into the bathroom, and I could hear him muttering to himself; pacing back and forth like an old-school virgin bride on her wedding night, which only made me laugh all the more!  Finally, the door opened, the bathroom light went off, and I pretended not to notice as he came and stood quietly at my side of the bed. He sighed once or twice, then whispered softly, “Fine. YOU WIN. But I’m NOT going to enjoy it. I’m ONLY doing it because I want to have anal sex with YOU!”

I opened my eyes and smiled up at him, popping up in bed and snatching up the lube he’d been planning on using on ME.

He muttered something about being glad SOMEONE was happy about it, and I just laughed and told him to get into bed. He climbed in as I rummaged in my bedside table for my small g-spot stimulator. I guess it would be sort of mean of me to expect him to take my big fat strap-on the FIRST time out. I ordered him to get up on his hands and knees on the bed. A tiny drop of humility is EXACTLY what this man has been needing to make him tolerable to the likes of a hot slut like ME!

He was about to learn his place.

I playfully smacked his ass, then began rubbing my hands up and down it. I ran my finger lightly down the length of his ass crack, and he jumped as if he’d been shot! Then I giggled a little meanly, separated those cheeks, and teased my finger over his asshole. To my surprise, and possibly his, he let out a small moan! He stifled it quickly, and I giggled as I took the lube and poured it into his tight little man pussy, pulling it apart slightly with my fingers. Both asshole and fingers were slippery now as I started massaging all around that hot little hole. I took the tip of my finger and slid it just inside. I expected protest, but what was this? His ass.. it was… WIGGLING!

Almost pushing itself backward at me, as if he wanted me to push in deeper! I laughed softly and he pulled forward as if to stop me. I grabbed an ass cheek and squeezed, rather roughly. “BE STILL” I admonished, and to my surprise, he was. I continued working my finger into his ass, smiling as I felt him tighten around my finger and try to push it out. I let him, and then the next thing he felt was my toy invading that virgin asshole!

He cried out in protest… THEN, I turned it on. 🙂

He jerked violently, letting out a strangled moan. I held it in nice and deep for a moment, then pulled it back out so that the tip was vibrating against JUST the right spot… massaging that prostate that had never EVER been stimulated. Oh. My. God!! It was like trying to ride a wild bronco! My big macho man that didn’t want his ass played with was actually GRUNTING in pleasure as I fucked him! My shocked ears heard the softest whisper, just then.

“FUCK. Harder. Please fuck me harder”.

My jaw dropped to the floor! And then, just as my man requested, I began fucking his tight little asshole deeper.. and harder! He was fucking SWEATING with the effort of pushing back against me. Moaning, groaning, and jerking his cock at the same time. Suddenly, he let out something that was half-moan and half-scream, and I saw a stream of cum shoot out of his cock and practically across the room!

…I haven’t been asked for anal since. However, he NOW begs for anal penetration on a regular basis! 😉

Kinky Sex Stories and Cheap Phone Sex!