Em & Mike Ch. 02: Second Night - Pegging

"Listen." I tapped Mike's balls gently to get his attention.

"Ahh, shit."

"I'm going to remove the plug, and then push the head of the strap-on straight in. You will already be open and it's not much bigger so it shouldn't hurt."

"Christ. Please fuck me."

"This first time," I told him firmly. "We are going to be cautious."

Mike nodded.

"Okay, I understand. Thank you, Mistress."

I smiled and got a firm grip on the slippery plug.

"I'll fuck you later." I promised, then slipped the plug out slowly.

Mike had started to laugh at my words but was soon groaning again as he was emptied.

"Oh, Oh."

"Just breathe."

"I'm breathing." Mike gasped out.

The plug slipped free and I threw it to one side, immediately slipping the end of my 'cock' into the vacated space.

I leaned over and placed my hand on Mike's stomach again.

"Three deep breaths, right down to my hand."

"I'm breathing." Mike rasped out.

"You're white as a sheet." I corrected.

Mike tried a couple of breaths and got it right on the third. I rewarded him by replacing my grip on his cock and sliding him back into the rhythm.

"Oh. Oh, Christ."

"You ready?"

"So ready."

Slowly and gently stroking Mike's cock, I carefully pushed the strap-on deeper into him.

The colour flooded back into his face as he dragged air in through his clenched teeth, eyes fixed on the cock disappearing inside him.

I stopped at about two thirds depth and checked him over. Mike was half sobbing now. He lay back and trying to smile, nodded at me to continue.

This strap-on was small and safe, so I wasn't worried about harming him, but I wanted Mike's first experience of penetration to be a positive one. He had been waiting a long time to try it.

Watching as his eyes squeezed shut, I pushed my hips forward and buried myself deep inside him.

Mike was shaking so hard it was like using a vibrator.

It was a struggle for me to stay still and allow him to adjust, I just wanted to pump and pump into this gorgeous man spread out beneath me.

Finally, Mike's eyes opened, and he looked at me and grinned.

"Doing okay?"

"I'm good Mistress."

"In that case." Grinning back at him I started to move.

"Ahhh, shit." Mike groaned, as he was emptied and filled again. I was still pumping his cock which was slippery with pre-cum.

It wasn't long before Mike started to gasp.

"Gonna cum." He warned me.

I bit my lip, this was frustrating for me, but this first time had to be about Mike.

"Cumming. Mistress I'm cumming." He yelled.

"Ahhh."

Mike sprayed all over my hand and stomach as he came hard, letting lose a low, drawn out grunt.

I made sure to milk him thoroughly and he was sobbing, his head swinging from side to side before I let him go and gently withdrew.

Pushing his legs down I crawled up and stroked his cheek with my left hand, (the hand that wasn't covered with his spunk. I'm considerate that way.)

"Look at me."

"Jesus." Mike was still cursing and gasping in air.

"Mike, look at me."

He squinted up at me for a minute and then we were both laughing.

"Oh my God."

"That was so intense."

"Fucking awesome."

"Any pain?"

"No, no I'm good."

I rubbed my thumb along Mike's lip a few times, until I was sure.

"I need to clean up, then I'll come and release you." I held up my right hand to demonstrate why I needed to clean up first, and Mike laughed at the state of my hand.

Two minutes later, I returned to him, still flushed and trembling on the bed.

I quickly released the wrist cuffs and pulled him into a hug, soothing him as he calmed down a little.

"Was it what you expected?" I asked him quietly.

"I thought it would hurt more." Mike replied.

I smiled and kissed the top of his head.

Mike shifted back and looked up at me.

"Are you Emily again, or still Mistress?"

I raised a brow as I considered him.

"That depends."

"On what?"

"On whether you want to stay snuggled here getting your breath back, or whether you want to bend over the end of the bed and let me fuck you hard in the ass."

Mike's mouth fell open as I reached around and rubbed lightly at his butt. He had already closed, really that strap-on was perfect for first timers.

"For real?" Mike couldn't stop the grin from spreading.

I held his face in both my hands.

"This time I get to cum. It will be rougher, so be sure."

"I'm sure." Mike leant forward and kissed me quickly before starting to gingerly move off the bed.

"Sorry Mistress." Mike apologized for stealing a kiss before kissing me again and then leaning over the end of my bed.

Feet wide on the floor, hands on the cover, he bent himself double over the bed rail, like an offering. He was already getting hard again.

"Please Mistress, I want you to cum."

I walked to Mike and ran my hands over his legs, back and butt.

He was already starting to tremble, but it was excitement.

I pushed gently at his hole.

"I'll have to push my way in this time." I warned.

Mike's voice caught so he cleared his throat and tried again.

"Please Mistress. Fuck me."

His eyes were nervous, but dark with desire and looking at him bent over for me like this, nothing was stopping me now.

I grabbed the pillow.

"Put his under your tummy, I'll be pushing hard."

Mike placed the pillow between his hard stomach and the bed end, bending back over it.

"Do I need to secure you?"

"No Mistress." He croaked out.

"You remember your safe word?"

"Yes Mistress." Mike's voice shook a little.

I pushed his feet slightly further apart to lower him, and then ran the strap-on along his ass and over his balls, like he had done to me that morning.

As I lined myself up, Mike's breathing sped up dramatically. I took a breath to steady myself and pushed.

"Ahhh."

We both cried out as I pushed in, Mike was so well lubed there was little resistance, and I went deep and hard. Then again, and again.

Mike's fists were gripped in the bed cover, breathing jagged as I fucked him faster and harder.

"So, fucking good. Ahhh. Please don't stop."

I was grunting with effort as we both became slippery with sweat and lube.

Mike's shaking was sending me close to the edge and I was praying now that he wouldn't safe word out.

Before long before I felt myself started to build. Gasping out in between Mike's grunts.

"Need to cum. I need to cum."

"Oh, fuck yea. Cum in me Mistress." Mike managed.

"Need to push hard."

"Do it."

I growled as I grabbed Mike's hips hard and pushed deeper, the friction triggering my reaction as the orgasm crashed through me.

Mike had reached down and was pumping his cock, groaning as he came again.

"Oh, my fucking god." I cried out as I rammed deeper into him, before collapsing over him shaking like crazy.

Mike was sobbing under me, and after grabbing a few quick breaths I pushed myself up and out as carefully as I could manage.

He still squealed though.

We both staggered back around the bed, half supporting each other, before falling in a heap onto it, our breathing gradually switching to laughter.

"Mistress?"

"Emily."

Mike's bottom lip poked out, making me laugh harder.

"No more play tonight, are you crazy?"

Mike grinned and shrugged.

"Did I hurt you?"

"A little." Mike admitted.

I rolled over to sooth his hair.

"I'm sorry. I needed to cum so bad."

Mike just smiled and flushed a little.

"Oh." I said as realization dawned.

"You liked it."

"A little." He flushed deeper.

"That's okay. Not hurting now?"

"No, no I'm good." Mike reassured me.

We lay for a while, excited by the adventure we had started, making more plans and Mike threatening all sorts of mayhem for his first time as Master.

Both exhausted we were soon crawling under the covers and snuggling down.

Mike nuzzled into the back of my neck.

"Are we having early morning sex again?" he asked sleepily.

"If you wake me up at 5am, I'm gonna sit on your face."

"That could be fun."

I turned round and scowled at Mike who was waggling his tongue at me obscenely.

"I wasn't being friendly."

But I couldn't stop the grin as he pulled me back in close.

Coming Soon. Em & M Ch 3: Hotel Stranger.