I never thought much of anal sex for the longest time, in any form. I’m a cis-male who was generally always into your standard, run of the mill porn. Heterosexual, lesbian at times, some other different fetishes but nothing ever involving anal and definitely not pegging.
I didn’t even really know it was a thing until I watched a video of my favorite pornstar at the time where she was pegging a guy. The description of the video had nothing to do with pegging and the thumbnail images never showed it either, but it made up a good portion of the video. Anyways, it was Remy Lacroix pegging a guy with a pink strap-on dildo (a bit of a deep cut for you porn fanatics).
When it first started showing the pegging scenes, I was obviously confused. But I found that as I was watching, I never lost my erection and was actually sort of turned on by it. Remy taking control of the situation and fucking the guy in the ass was super hot to watch, and it made me question for a brief moment what I really wanted to see. The rest of the video was back to standard stuff (at least as far as I remember), so I kind of forgot about it for a few years.
Fast forward a few years and I find that I’ve recently really gotten into transporn, of all types. Something about seeing a beautiful woman with a hard cock getting fucked or fucking a guy just absolutely makes me lose my mind. I can’t get enough of it and find myself daydreaming about it constantly throughout the day. But it is something that I could never envision myself telling my wife. She would think I’m nuts or gross or not want to touch me which would be terrible. After not being able to kick my addiction, I decided I needed to broach the subject with her somehow. It all happened during a normal dinner one weekend.
My wife and I were sitting at dinner, finishing eating and getting ready to clean up our plates. Our anniversary was coming up so the timing of bringing up something bedroom-related wasn’t that far fetched.
“Hey babe, what do you say we try something a little bit different in bed the next time?” I said.
“Ummmm, okay, what do you mean or have in mind?” My wife asked.
My wife isn’t the most open or outgoing person when it comes to sex. Don’t get me wrong, I love having sex with her and she’s great, but it’s usually the standard missionary, minimal foreplay at times, occasional doggystyle, nothing too crazy. Which is fine by me, but I was yearning to try something new.
“Well, I went and bought us a toy we could use if you think that’ll be fun! It’s just a regular dildo but you know, two is better than one!” I said enthusiastically. I couldn’t just come right out and ask her to peg me. I was hoping I could convince her to let me use it on her and then it would all work it’s way in from there (no pun intended).
My wife laughed as she was putting the dishes in the sink.
“Do you think yours isn’t enough? You know I love what you have for me baby,” she responded.
I was relatively well-endowed so I appreciated the comment.
“No it’s not that, I just thought it might be something different to spice things up that’s all!” I said.
“Do you have it already?” She asked, referring to the dildo.
I went into the other room to grab it. It was still in the packaging in case I needed to return it. It was a standard 6.5” silicone dildo, nothing too over the top.
I brought it back out and showed her.
“You’re bigger than that, babe! I don’t know if I want something smaller!” She said.
“What if we used it at the same time?” I said, alluding to a DP situation.
My wife’s eyes lit up with confusion and potential excitement.
“You mean like stick it in my ass while you’re also inside me?” She asked.
“Only if you’re comfortable with it!” I said.
My wife wasn’t a big anal fan. She had done it a couple times with me, so she wasn’t totally against it but it would take some coercing to convince her completely.
“Let me sleep on it, babe. I love that you’re thinking outside the box though!” She said as she kissed me as she walked by.
I anxiously waited for her answer in the coming days.
Finally, that Friday, she gave me her answer.
“If you really want to try something new, I’m up for it. Who knows, I could end up loving it!” She said.
My mind was racing with the potential for these new possibilities. We decided that we would try it out that night. I just needed to figure out a way to bring up pegging at some point. I had already bought the strap on harness, I just hadn’t showed her or told her that part yet.
Friday night rolled around and my wife and I were getting ready for bed. We’d enjoyed a nice dinner and I was laying in the bed, naked, slowly stroking myself (semi-hard) while I waited for her in the bathroom. She came out a few minutes later.
She had decided to wear some sexy lingerie for me that night, which immediately sent my dick into its full erection. My wife stood about 5’6” tall, medium length dark hair, a little thicker but not overly big, probably 150 pounds. We’ll distributed around her thighs and ass. She had tits on the smaller side, a small B cup, but they were still perky. Her white lingerie outfit accentuated her figure beautifully and the strategic cut outs showed her pussy which appeared to already be a little bit wet. I threw the covers off of myself to expose my hard cock.
My wife smiled as she was happy she had already brought me to my full attention. She climbed onto the bed sexually on all fours approaching my raised cock.
Once at my lap, she reached her hand out and slowly started to jerk my manhood for me. I’m about 8” at full erection and medium girth, a respectable above average size. My wife had her hair pulled back in a ponytail.
She lowered her head down and took in the first couple inches of my dick. Her lips were warm and her tongue flicked at the top of my cock, causing me to twitch slightly. As she bobbed her head up and down, slowly taking in more of me, her hand followed suit, stroking me with equal rhythm. I moaned under my breath.
I looked down to see my wife had stuck her hand down and was beginning to play with herself a little bit with her free hand. She moaned as she sucked me, creating a nice subtle vibration around my cock. Eventually I felt myself hitting the back of her throat as she fit as much of me as she could inside her mouth without gagging too much.
“Fuck that’s good…” I moaned quietly.
After a few moments more my wife removed my cock from her mouth and climbed up on me. Her tits hovered over my face as I reached up and spread open her lingerie, freeing them. Her nipples were hard as I took one of them into my mouth and flicked my tongue against it. I caressed her other breast as I sucked on the other, switching back and forth from time to time.
Without warning, I felt a warm cover my cock. My wife had sat down on me, filling herself with my full length as she let out a deep moan. She must’ve been feeling good about this new experience we had planned as she normally wasn’t this outgoing, but I was happy she was taking control.
She let herself sit on me for about a minute, enjoying how I filled her up, slightly rocking her hips from time to time. We were enjoying the slow fuck for a few minutes before my wife raised up off of me and kissed me deeply.
“Do you have the toy?” She asked me.
I smiled as I sat up and got it out of my nightstand, along with a bottle of lube. I held the dildo in my hand and showed it to her.
She smirked and grabbed ahold of it.
“I know it’s small than you, but it’ll do…” she said in a seductive tone. “So what did you have in mind?”
“I was the thinking we could do doggystyle, and then I could stick this in your ass whenever you’re ready. That way I can see what I’m doing a little better,” I said with a laugh.
My wife smiled again and blushed.
“Okay let’s do it!” She said excitedly in a giddy voice.
My wife assumed the position and I kneeled behind her. She laid her head down on the bed with her ass in the air waiting for me. Her asshole looked delicious as it awaited the penetration.
I grabbed my cock and directed it into her, filling her slowly as I made my way completely inside of her. I sat for a moment and watched as my wife slowly rocked forward and backward, fucking herself on my rock hard dick. As she did so, I leaned down and grabbed the dildo and lube.
“Just let me know when you’re ready!” I said.
“Okay, go ahead. Just go slow,” she said quietly.
I applied a healthy amount of lube to the dildo, stroking it, imagining how it would feel inside of me. After it was probably lubricated, I turned my attention to my wife, as I dropped lube onto her asshole.
It was still sort of cold so it drew a quick pucker from my wife. She laughed as I started to massage it around her ass and lightly stuck the tip of my finger inside.
“Okay just tell me if I’m going too deep or fast,” I said.
I grabbed the base of the dildo and placed the tip at my wife’s asshole. I slowly pushed forward and saw my wife’s asshole open up to invite it inwards. My cock was still inside of her, throbbing at the sight of it.
My wife let out a gasp/moan. “Ohhhh mmmmm,” she moaned.
I continued to push inward, entering her about 4”. I let it stay there as I started to stroke my cock in her as well, giving her both sensations at once. She moaned louder with each thrust.
“Oh fuck, yes! Mmmm that’s fucking amazingggg……” she drawed out.
As I fucked her, I started to stroke the dildo well, slow long strokes to accompany my faster ones. Her asshole gripped the toy tightly and pulsated from time to time as it tried to accommodate the new entry.
As we continued her moans grew fast, quickly becoming almost orgasmic. I sensed she was close and drove the dildo all the way inside of her to the molded balls, filling her completely. My wife yelped in pleasure as I fucked her. I saw her hand between her legs playing with herself.
“Fucckkkk I’m gonna CUM!!!!” She yelled.
I thrusted faster as I felt my wife’s pussy contract on my cock as her asshole tightened as well. I let the dildo stay buried as I slowed my strokes down, letting my wife complete her orgasm as I slowly stroked her.
Her breathing slowed as she came back to her senses. I slowly removed the dildo from her ass and saw her asshole close tightly around it once it was out.
“So I guess that was pretty good?” I said.
“You have no idea…” she nearly whispered as she rolled over onto her back. “You didn’t cum yet?” She asked.
It was time to try and bring up the situation.
“No not yet. I was trying to save it.”
“Save it for what?” She asked, still slightly out of breath.
“I was thinking maybe you could use this on me?….” I said, waving the dildo.
My wife looked at me quizzically. “What do you mean?”
I reached into the drawer and pulled out the strap on harness.
“I bought this too. It’s called pegging. Basically it’s when you use this to fuck me,” I said.
My wife laughed. “Are you sure?”
“I’ve always wanted to feel what you experience, and since I don’t have a pussy, my ass is the only alternative! If you aren’t comfortable with it, it’s okay,” I said.
My wife sat for a moment before finally agreeing that she would try. She grabbed the harness and started to buckle it on, taking a few minutes for us both to figure out how to actually affix the dildo to the contraption.
Finally, my wife had the strap on buckled properly and the dildo sat staring at me. She looked beautiful, holding the cock in her hand as she stared at me.
“How did you want me to do it?” She asked.
“I’ll just lay on my back and we can just go slow to start I guess,” I said.
I had fallen soft from the break in action, but still leaked precum. I laid on my back and spread my legs apart, handing my wife the lube bottle.
“Don’t be afraid to use a lot!” I said laughing.
My wife smiled and grabbed it and covered the dildo. She squeezed more into her hand and I felt her warm touch caress my asshole, covering it with lube.
She walked between my legs and positioned the dildo at my asshole. I felt it slightly prod against me as I looked down, seeing my wife still get accustomed to having a cock and how to angle her body.
“Are you ready?” She said looking up at me. I nodded.
Suddenly I felt a pressure enter my asshole. I felt the tip of the dildo enter me, hurting slightly but not too much to stop. She stopped to make sure I was okay. I nodded again.
Slowly, I felt a more intense pressure build up as she pushed in further, I felt like a lot more than 6” but she was only halfway in, my body still not used to this new sensation.
I moaned, noticing some sensation return to my flaccid manhood. My wife grabbed my legs and pushed in further until I finally felt the balls touch my ass.
“Wow, you’re taking this like a champ! Are you sure you’ve never done this?” She asked.
I couldn’t respond but just lightly laughed as she started to back out, beginning some slow strokes. As I felt her enter me, I looked down to see my dick coming to life. I was nearly fully hard and my wife was staring at it as it flopped gently with her strokes, smiling.
“This is fun!” She said.
As my ass was filled with her cock, I started to feel a sensation that was almost like I had to pee as she was hitting my prostrate. My cock rocketed up fully hard, causing my wife to grab it and start stroking.
“Mmmm yeah you like that?” She said.
This new experience was bringing out a dominant side of my wife I’d never seen.
“Yes I love it!” I moaned.
She fucked me harder, matching her stroking to how fast she stroked my cock.
The sensation grew more and more inside of me. I knew I was about to cum.
“Oh fuck keep going! I think I’m gonna cum!” I yelled.
My wife obliged, letting go of my cock and grabbing my thighs, forcing herself into me at a faster and harder rate.
“Oh fuck yes yes yes yes!” I yelled.
Suddenly the sensation overtook me. I wasn’t sure what was going to happen. I felt tingles take over my body as I looked down and saw my cock exploding with cum. Shooting up into the air as my wife smiled and laughed at the force of her fucking it out of me. I shot ropes skyward, arcing back down and landing on my stomach.
The sensation was indescribable, cumming hands free as my wife fucked my ass. I could feel her entering me with each thrust, each time cumming more as she hit my prostate.
Slowly the feeling subsided as my orgasm came to an end. I lowered my hips back down, signaling I was done. My wife stopped as well but left the dildo buried in me. She leaned forward and kissed me before removing it slowly.
She stood before me smiling, admiring the cum on my stomach and her new cock that she just fell in love with.
“Babe, that was amazing!” I said out of breath. “That’s what you feel all the time?”
My wife laughed.
“Looks like you’re gonna be feeling that a lot more often now….” She said seductively, letting me know she loved it too…
Source: reddit.com/r/eroticliterature/comments/10x4xu7/discovering_my_love_of_pegging_m29f29_married
Something I want to try