First Time Pegging

The story of how I became interested in pegging is a strange winding road. The following is a true story...

It started with covid and my wife and I having more time to explore in the evenings after we put the kids to bed.

To spice things up I had downloaded a sex app where couples can play truth or dare and answer sexy questions about one another. We had been married for several years but she didn't like to talk about her past.

I knew my wife was no angel before me and had been with several men, I just didn't know any details. We had been playing the game for close to an hour and were both really into it.

We got to a challenge where I was supposed to put my cock inside her while she told me about her first time. She was naked on her back so I got on my knees between her legs and glided my cock into her already very wet pussy.

I leaned close and whispered, "tell me about your first time."

At first she was hesitant. I started thrusting slowly in and out, "come on baby."

She bit her lip, "I was at a house party with my sister and it was with some older black guy."

"Wait, what?" I exclaimed. I stopped thrusting a little shocked at her answer. My dick was still hard inside of her. I was insanely horny and wanted to cum so I didn't want to ruin the game.

I went with it, "tell me more baby." I started thrusting slowly again.

She said, "we were just at this party and I wanted to try it so I did."

For some reason, how casual she was about it made me even more horny. I started moving a little faster. I asked, "did he have a big dick?"

Now she was getting into it as well, "yeah he did."

"Bigger than mine?"

"Oh yeah," she moaned. "A lot bigger."

This drove me crazy. I grabbed her ankles, spread her legs in the air and fucked her as hard as I could.

She screamed with pleasure and we finished at the same time with me filling her pussy with cum.

We fell asleep and I dreamed about her fucking that big black dick all night.

A couple days later and we were in bed again. We were playing our app again and this time I had to confess to a fantasy. This one was easy for me as I have a foot fetish and she knows all about it.

After reading the question she quickly said, "you can't say feet, I already know that one."

That stumped me for a second and I started to get nervous. I knew what I wanted to say, but didn't know how.

"You remember what you told me the other night?" I asked.

She nodded her head.

"The idea of you fucking that guy made me so horny." "I think I would love to watch you fuck another man."

Now it was out there. "What do you think about that?"

She hesitated for a minute and told me, "I would've tried that when we were dating but not now that we are parents."

Just her saying that drove me wild. I pushed her on her back and shoved my throbbing cock inside her. "tell me more."

She told me about fucking another guy and her sister walking in on them. I exploded instantly.

After, while we were laying in bed I asked, "what if I bought you a big dildo?" Could I watch you fuck it?"

"Yes," she said and we went to sleep.

The following week I got a text from my wife while I was at work. She told me a package came for me in the mail. I didn't remember ordering anything so I asked her, "what did we get?"

She responded with, "you'll see."

At lunch time I was sitting at my desk finishing up my sandwich when a video message came through on my phone. I opened it and saw my wife pouring lube over a big mocha colored dildo and giving it a footjob.

My dick started pressing in my pants as another video came through. Now she was teasing her pussy with the huge dildo. She moved it up and down her slit and slowly started sliding it inside herself.

The next video came through and now my wife was pounding her pussy with the dildo until I could tell she came hard. She pulled it out and it was covered in her juices.

I rushed to the bathroom, pulled out my cock and jerked off right there rewatching the videos.

The rest of the day all I could think about was what would happen later that night. We put the kids to bed early and then it was time.

My wife laid on her back sideways across the bed and I knelt on the floor so I was eye level with her pussy. I lubed the dildo and started rubbing it on her pussy just like I had watched her do earlier. Then I slid it inside her and started slowly fucking her with it.

She was moaning with pleasure and grabbed my hand to help gide me to the pace she wanted. I started to pull my hand away and let her take over.

I stood up and took my clothes off while she moved on the bed. "I want to watch," I said. I climbed onto the end of the bed at her bare feet and sat on my knees with my hard cock standing straight up.

My wife started to fuck herself with the dildo writhing with pleasure. It seemed like this dildo satisfied her in a way I couldn't and it was driving me wild.

I started jerking off watching her go and blew a huge load all over her bare feet. Then I moved my head closer to her pussy to watch her get fucked up close.

A couple minutes later she started having one of the strongest orgasms I have ever seen from her. She slowly pulled the dildo out of herself and it was covered in her juices. I just couldn't help myself and I started sucking the dildo like I had been sucking cock my whole life.

To my surprise, this didn't repulse her so I kept going. I stopped sucking the dildo and cleaned her pussy with my tongue then went back to the dildo. I was so turned on I thought cum was going to start shooting out of me.

I couldn't take it anymore and I just blurted out, "fuck me with that big cock."

"Ok," she whispered.

I got on all fours and she reapplied lube to the dildo and her fingers. She started slowly going around my asshole with a lubed finger and inserted it inside me. This was the first time anything had been in my ass and I was hooked.

She fingered my ass and then started trying to put the dildo inside me. We tried for a few minutes but I was too tight for such a huge cock on my first time.

We gave that up and I flipped her over and started fucking her. She stuck her finger back in my ass and I came deep inside her.

We laid there exhausted with pleaure. I asked, "could we do more of this stuff?"

"Yes," she replied. "If this is something you wanna try."

"It really is," I told her.

It grabbed my phone and we shopped for a strap on that would be more my size right then and there.

It was an agonizing 7 days waiting for it to arrive at our door. The day it came my heart couldn't stop racing. It was impossible to focus on anything else except for the idea that tonight my wife was going to fuck me in the ass.

Finally, it was time and it has to be said that my wife is amazing. If you have been involved in pegging before you will understand this as true. Putting towels down, figuring out how the straps go on her body and getting the dildo hooked up right are not exactly sexy foreplay.

We joked through the process having fun with it. We had settled on a 5" smooth dildo that was less thick than my own cock but thicker than a typical "starter" dildo.

When we were finished I stood up and kissed her hard. Our mouths opened and we started making out like horny teenagers. Then she stopped me and pushed me onto my knees. I started sucking her cock like a pro.

She led me over to the bed and I laid down on my back. My wife got on her knees and covered the dildo and my asshole in lube. She got closer and started rubbing the tip against my hole. Then teasing it losening me up.

She looked at me, "does it hurt."

"No," I moaned. "Stick it in."

She started pushing and the cock slid deep into my ass. The pressure hurt for just a moment and we paused leaving it inside.

She started with smaller strokes, learning how to move like a man fucks for the first time. She grabbed my cock and started gently stroking it.

I could feel the pleasure building as the dildo occasionally found my prostate.

"Fuck me baby!" "I want you to fuck me!" I shouted.

She started thrusting harder and harder. She kept playing with my cock but I took her hand away. I didn't need it. I could feel that I was going to be able to cum from just her fucking me.

"Keep going," I begged.

She was pounding my ass and my hips were writhing with pleasure in rhythm with her thrusts.

"I'm gonna cum!" I shouted.

"Cum for me baby," she replied.

I exploded, cum covering my chest, hitting me in my neck and face. She leaned down and licked a drop of cum from my lips and we kissed. My body was completely spent from overwhleming pleasure.

I love my wife.