First Time Pegging: He Didn’t Know He Wanted It

First Time Pegging, Will. He Took It So Good!

Will and I had been dating for about six months. I had no idea I would be there for his first time pegging. We always had fun together, no matter where we were or what we were doing, and our sex life, oh my, our sex life was HOT!

Will was a remarkably sexy man. Ladies would check him out everywhere we’d go, and on occasion, we would take one of them home to play with us. Usually, I would seduce her first, kissing and caressing every part of her body until I inevitably threw her down and opened her legs. I was priming her. Slowly I would tease her with my tongue and fingers until she was begging for cock. That’s when Will would come in and fill her with all his 9 inches.

I started to have a craving; I had dreams about my first time pegging Will.

I went to our local sex shop and bought a big black strap-on. Ha-ha, I remember trying it on for the first time and smirking to myself because I now had the same size cock as Will. The next lady we brought home was going to be all mine. One day, we met a hot, petite little brunette at our local coffee shop. I instantly knew she was the one I wanted to try my new cock out on, and I told her she was coming with us. She agreed. After my usual seducing and teasing… I strapped my new cock on and fucked her to one of the most intense, leg-shaking orgasms I’ve seen. I still remember the look on Will’s face. He looked pretty impressed… and his cock was rock hard.

We did this a few more times with a few more ladies. Often, I catch him gazing at my strap-on, starry-eyed, before, during, and after I use it to bring them earth-shattering pleasure. Every Sunday, I go to lunch with a girlfriend, and we always talk about sex. One particular Sunday, she mentioned porn she watched the night before about a man and his first time pegging. She said it turned her on and sent me the link.

Later that night, Will and I were watching television, and I told him I was tired and going to go lay down (really, I couldn’t wait to watch the porn that turned my girlfriend on so much). I hit play, and surprisingly, I was glued. My pussy started to get wet, and my hips started moving about 3 minutes in.

“What are you watching?” he exclaimed. “A man and his first time pegging,”

Will came into the bedroom, looking very surprised. “I thought you were sleepy?” he said. I said nothing – just kept moving my hips. “What are you watching?” he exclaimed. “A man and his first time pegging,” I answered. “A man and his what?” he asked. I showed him my phone. He looked a bit blank-faced, but I noticed his cock getting hard underneath his sweats. I was so hot at this point that I threw my phone down, jumped out of bed, and got on my knees to blow him. After a bit of cock sucking, I put my finger in his mouth. I wanted him to lube it up before I stuck it in his ass. One finger in his ass turned to two, and I told him to lay down on the bed.

I grabbed my strap out of the nightstand and put it on. “What are you doing?” he asked. I hushed him and started lubing it up. His eyes were wide, yet he said nothing. His cock was throbbing at this point, so I knew he was ready for his first time pegging (even if he didn’t). I ordered him to put his legs up and started rubbing the tip of my big black strap-on all around his asshole. His breathing got heavier, and I knew he wanted me to fuck him.

I still wanted to tease him a little. Suddenly he blurted out, “fuck me; please fuck me!”

I smiled and slowly inserted my cock inside of him. He jerked off as I rammed my big black cock in and out of him. He was moaning like I’ve never heard him moan and quickly blew a load like I’d never seen him blow. Worn out and happy, we kissed and went to sleep.

The following day, the first thing when we awoke, he said, “Wow, baby! Last night was amazing!”.  Of course, I smiled. “I didn’t even know I wanted that, but fuck!” he said. “But I did – I knew you wanted it,” I said…

And that was the beginning of me filling up Will just as much as Will filled me up, night after night.

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