Em & Mike Ch. 12: Pleasure Pain by emilyagilbert,emilyagilbert

I drove Mike relentlessly up and over. Ignoring his cries. Ignoring his pleas.

Ignoring his shout as he unleashed himself down my throat, and I continued to pull everything that I could out of him.

Soon the moans and groans of Mike’s orgasm started to be replaced by harsher, higher pitched sounds.

“Ah, Oh, Oh. Fuck. Ahhhhhhhh.”

Words and pleas became a high-pitched semi-scream as I continued to worship Mike’s cock.

When he dragged in a breath on a cracked, choking sob and started to shake violently, I relented slightly and moved my attentions back to his balls.

Sensitive, but not quite so sensitive.

Mike is not a pain toy. There is a limit to how much he can take.

I ran my tongue firmly from Mike’s balls to his hole and back.

He struggled against the restraints, “Oh, FUCK, Emily!”

Sighing, I kissed Mike’s balls again. Then blew a raspberry against him.

He squealed and giggled, ending on a deep belly laugh.

I grinned as well and walked back to push his damp hair away from his face.

“You know that your safe word doesn’t work today,” I reminded him, kissing him, and biting his lip gently.

“Hmmm? Oh, I didn’t mean to, I wasn’t trying to-”

“You didn’t mean to use your safe word?” I interrupted.

“No, sorry Mistress,” Mike trailed off and just shook his head.

“Good,” I gave him a dazzling smile and brushed my hands together, “then let’s move on.”

“But I came?”

I just looked at him.

“Oh, Shit!”

I moved to a nearby bench that Mike had not bothered to look at closely and picked up a toy.

Mike’s eyes widened as he saw me approach with the leather ball stretcher.

I giggled and kissed him, “I’m not going to hurt you sweetie, it’s just to increase sensation.

I carefully attached the parachute style stretcher, soft leather enclosing his balls, and tugged gently.

“Comfortable?”

“Mmmmm,” Mike agreed, wordlessly as his eyes fluttered closed and his cock started to stir.

Humming to myself I moved away and pulled a sheet off an interesting device.

Mike still had his eyes closed, enjoying the new sensation on his balls. Pulling a little at the restraints. Wallowing a little in the feeling of submissive helplessness.

He stirred himself as I rolled the table mounted device over to the cross and between his legs, setting the brakes.

It may have looked spindly, but it was clearly a fucking machine.

The look of blank shock on Mike’s face made me giggle.

(Shame I couldn’t film it!)

“Okay, let’s see,” I murmured, ignoring Mike’s fish impression as he tried to get his voice to work, and rooting around in the drawer that was part of the table the machine was mounted to.

“Ah Ha!” I cried as I brandished an attachment at him.

It was approximately the size of my arm from elbow to fingertips, but much, much wider.

Mike squeaked.

I mean he literally squeaked. It was brilliant.

“No?” I turned back to the drawer and rummaged again.

“Ohhhhhhhh!” this time I needed two hands to wave the attachment over Mike.

It was a similar length, but sort of knobbly, and the base was about as wide as Mike’s entire ass.

Mike’s shocked looked dissolved into a grin as he threw his head back and laughed.

His stomach trembled as his laughter bounced around the room.

I grinned and rested my hand on his tummy.

It actually took him about five minutes to calm down enough to speak. Just a hint of hysterical in there.

Once he was calmer, I turned back to the drawer.

“Oh, come on,” Mike said, “you are winding me up.”

I turned with the correct attachment. It was already covered in a condom, as I had prepared everything the evening before.

I also had plastic gloves, a towel and lube.

“Fuucckk,” Mike gasped.

I moved forwards so he could see this attachment clearly.

It was slightly smaller than the strap-on we used, so it was not going to hurt him. However, I knew that the relentless sensation of the machine driving into Mike was going to be a challenge.

Mike moaned and bit his lip as I slipped on the glove and prepared him. His hips tried to thrust as I slipped my fingers in and out. One, then two, then three.

Three was enough, this dildo attachment was not big.

Mike watched everything, his forehead crinkled in concern, but he didn’t question me. He trusted me, and when I caught his eyes he was deeply aroused.

I used my slippery hand to stroke his cock a few times, he was already hard, but this made him throb.

He jumped at first contact, but quickly realized that it didn’t hurt as much as he expected it to.

Judging by the low growl in his throat, it didn’t hurt at all.

I screwed the dildo into place and moved the machine’s arm forward.

The owner of this enticing establishment had given me a very thorough lesson the evening before, using one of his own submissives to assist. (Not that I was telling Mike about that!)

I was delighted to see my guess that the sub was close to Mike’s size proved accurate, as the dildo slid home.

Easily, painlessly, and deep.

Mike’s eyes shut again as he embraced the sensation of being filled.

I carefully watched him as I gently nudged the arm forward. It was fully extended, as I slipped a little deeper, and a little deeper.

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