Boldlyhardobject - Untitled

“I can’t believe I’m here with you Jessica. When you posted that story competition and offered a handjob as the winning prize I knew I had to try to write something, but I swear I never dreamed I would actually win,” said Mike as he lay back on my table. He was naked and his cock looked achingly hard already. 

“Well you were my lucky winner and now it’s time for your prize. You don’t mind if I tie your hands to the desk above your head do you Mike?” I asked as I was already looping some soft rope around his wrists and the table. 

“Oh yes Jessica. That just makes this even hotter,” said Mike as he waited for my fingers to wrap around his cock. “And by the way, that outfit you’re wearing is sexy as fuck.” 

“Thanks Mike, although I haven’t been 100% honest with you. Instead of just a handjob I’m going to do some experimenting with my new toy,” I said as I reached under the table and pulled out a new vibrating flesh light toy. Mike stared at it with wide eyes. 

“Mmm Jessica, you’re gonna make me cum with that?” said Mike with a huge grin on his face. 

“Um well yes… eventually… maybe,” I replied as I tried not to let out a wicked little giggle. I started to slowly tease the head of Mike’s cock with my new toy. 

“Eventually? Maybe? Oh fuck Jessica…. ooooohhhhh god!” he moaned as I slid my toy down over his hard cock. I gave him a few long slow strokes inside the flesh light before I started it vibrating. 

“I want to find out how long I can keep a man on the edge with my new toy,“ I said as I started slowly fucking his cock with the toy. I knew I could make him cum whenever I felt like it but it’s much more fun to see how long I can keep a man on the edge of cumming. “How does it feel honey?” 

“Oh god Jessica, it’s unbelievable. It feels so good as you slide it on and off my cock. Oooohh fuck! I don’t think my cock has ever felt as hard as it does right now just for you Jessica. This is going to be the greatest cum of my damn life,” he moaned as his cock glided full length in and out of my toy. I couldn’t hide the naughty little smirk on my face as he spoke about cumming. 

I teased and pleasured his throbbing cock for a full hour listening to the moans he was making as I took him to the edge of his orgasm time and time again before easing back and keeping him on the very edge before he could cum. It was just after the one hour point when Mike started telling me how he was ready to cum as he didn’t think he could take much more. I let out a little giggle as I continued to work his cock. 

“We’ve only been going for about an hour Mike honey. It’s going to be at least another hour before I even consider letting you cum.” 

“Another hour? Holy fuck Jessica I can’t. Please, I need to cum.” 

“Or maybe another two hours if you are going to be a naughty boy.” 

“Oh shit, please don’t say that. I will be good for you Jessica,” he groaned as he squirmed and pulled at the ropes that were binding him to the desk. 

Over the next hour I lost count of how many times I bought Mike to the very edge of exploding inside my flesh light. The moans coming from Mike were absolute heaven to my ears and even though he had said he would be a good boy after about 20 mins he started begging me to make him cum. Of course I ignored him and continued teasing the fuck out of his aching shaft until two hours had passed. Then I slowly eased my toy from his cock and saw the trickle of precum that must have been oozing from his cock for most of our session. Mike was pleading with me to make him cum. 

“Jessica I’m begging you. Please! I’ll do anything. Please let me cum. My balls have never ached for release like this before,” he whimpered as his cock twitched in front of me. As he pleaded I slowly slid the head of his cock back inside my toy. 

“Are you ready honey? Are you ready to cum for me?” I asked him as I stared into his eyes. 

“OH GOD YES! JESSICA PLEASE MAKE ME CUM!” he cried out as I slid his cock back inside my toy and started to fuck the hell out of him. I worked his cock with my toy faster, and faster, loving watching Mike thrash around on the desk. After keeping him on the edge for a couple hours I knew the exact moment he was about to cum, and when he reached the point of no return and was seconds from exploding into my toy I pulled it from his cock and grabbed his balls, squeezing them. Mike cried out in complete frustration as I stopped working his cock at the exact moment he needed me to pump the cum from his cock and I smiled as I watched his cock twitching in front of me. Then the first little spurt of cum leaked from his cock as he whimpered in utter frustration. A few seconds later a second little spurt of cum as his now ruined orgasm continued to slowly drive him insane. 

“AAAHHHHH FUCK! JESSICA PLEASE JERK ME OFF, I NEED TO CUMMMM!” he begged as his cock slowly leaked cum instead of exploding with a torrent of sticky cum. I just smiled and watched his ruined orgasm in full effect. After the last dribble of cum leaked from his cock I placed my toy back against the dripping head of his cock. 

“I think we’re just about ready for round two,” I said and smirked. 

“Oooohhhhhh my fucking god!” was all he could moan as I slid my toy down the length of his throbbing sensitive aching shaft 💋

Awww you're so cute when you're frustrated! I wish I'd known my best friend was a horny little submissive before, we could have been having so much fun all this time!

Okay you've had the cage on for a week so I guess you deserve a reward... here you go, my lovely tits for you to ogle and enjoy.

An orgasm? What are you talking about? You're in chastity! We both know that means you don't get to have orgasms anymore. All that cum will stay boiling in your balls for the rest of your life.

Alyssa Milano