My First Pegging

My First Pegging
Entering the World of Giving it up to My Wife
I had been out of the country on business. For two weeks. Or, a little over, actually. And it had been a long two weeks.
After my first time getting pegged (which was an amazing experience) I wrote about about my concerns whether getting pegged would make me want to start doing it with men. It’s a difficult thing to write about because even though I know there’s nothing wrong with being gay, being straight is a part of my identity.
We’ve each got our own hangover cure. For one of those horrible, deep down in your bones hangovers, the cure for me lies in cleaning things out. So that means showering, visiting the commode, and cumming. Continue reading Pegging: The Hangover Cure
My wife and I recently went on holiday. A few weeks before we left, I suggested we choose and buy each other a sex toy for the trip and surprise each other with our choice once we got to the hotel.
I don’t know how sex starts for most married couples but for us (we’ve been married for a few years now) it usually starts with us getting undressed. It’s not like it used to be.
Well, I just started writing a story which will be the next post chronologically but the previous post if you are scrolling down on your screen. Anyway, rather than talk about condoms and lube in that post, I thought I’d keep that one the story and give the condom/lube topic the attention it deserves.
Man, oh man I hate condoms. Oh, you too?
It’s something I am curious about. Does the idea of pegging your man turn you on? When you are doing it, does it give you pleasure?
I think I can imagine a few scenarios on how it might work but if there are any women reading this, I’d really love your comments on this one. Do you enjoy pegging your guy? Without your comments, here are the scenarios I can imagine.
Continue reading Do Women Enjoy Peggin Men?
It was sexy time. We were freshly showered and naked in the bedroom. I jumped onto the bed and with my wife still standing at the foot of the bed, I spread my legs in what I imagine, were she to make the same gesture, an invitation to dine.
I was, without a shred of subtlety, but with what I hoped was a little comedy, asking her to start the afternoon’s delight by whetting her appetite by… wetting my balls… with her tongue.
One of the benefits of getting pegged is that you know what it’s like to get fucked. My first “anal sex” experience was not with me getting fucked though. It was me fucking a girl I’d met that night and it was her hand that guided me there. However, with a little bit more knowledge I could have done better.
Now, with some experience in both roles – giver and receiver – it puts me in a position to offer some advice to potential anal first timers. Advice I wish I had had.
So we didn’t use the strap-on but we had a great night. So far, I have to say that even the idea of getting out the strap-on makes the sex better!
I got home and she was already home. She was in the shower. I peeked in to say hello and in reply she smiled at me then looked pointedly at my crotch then back up at me.

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Sandra studied nursing and sexual health and is named one of the world’s top 50 sexologists . She founded My Sex Toy Guide in 2016, where she and a team of experts write about relationships, LGBTQ topics, and other sexuality issues. She has been featured in Men's Health, Wedding Wire, InsideHook, ThriveGlobal, and more. Linkedin Profile
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The first time I brought up pegging, my husband Tim looked shocked. I told him pegging is known as “bend over boyfriend,” and he got the idea. I know it’s not everybody’s ultimate sex fantasy, but it’s worth trying to spice up the sex life. So sit back, relax, and enjoy our femdom pegging stories !
Disclosure: This article has affiliate links, and we may receive a small commission for purchases made through those links at no additional cost to you. Learn more .
We watched this adult movie one night, and it had this very erotic anal sex scene. I was enjoying it when suddenly, an idea came to mind. You see, I always wonder what it would be like to perform anal sex on my man with a strap-on. We’ve done a lot of kinky stuff in the bedroom, but we never tried this before.
Therefore, I thought it was about time to ask Tim what he thinks of pegging:
“Honey, what do you think about pegging?”
Tim was shocked, but his eyes sparkled:
“I thought you’d never ask. Some gay friends have said anal play gives them a whole new kind of high. But I don’t want you to think I’m gay; that’s why I never opened up about it. Frankly, honey, it’s one of my dirtiest sex fantasies since I was a teenager.”
“Well, it’s about time we do something about it. How does making your dirtiest sex fantasy come true?” I asked mischievously.
He chuckled. “How can I say no to that?”
That was all the motivation I needed, but I knew it would require planning because it was the first time for both of us. We were both excited, and to make it memorable, we decided to try it on our wedding anniversary, only a week away.
The first thing we did was order the toy together . It was so much fun because we couldn’t believe there were hundreds of strap-ons available online, in all shapes and sizes.
I wanted this to be special for my husband, so I let him choose the toys, and he finally settled on one that looked less intimidating. It was a beginner strap-on kit with a 5″ dildo . We bought it, and two days later, it arrived with the lubricants we also ordered.
When the big day finally arrived, I was giddy with excitement. Tim had to work at the office, so I had the whole house to myself, and I decided to try the toy first to see how well it fit me.
I put it around my waist, adjusted the straps, and looked in the mirror. I looked hot! The erect dildo seemed natural, and it felt real as I ran my finger and squeezed it as I do with Tim’s dick before putting it inside my mouth.
I’m sure Tim would be dying to have it inside him!
That night, Tim came home with a bouquet of red roses. He even gave me sexy black lingerie, which I planned to wear for our first pegging experience.
We had a nice dinner at home, and afterward, we decided to shower together. We were both naked when we returned to the bedroom, and I slipped on my new lingerie while my man got into bed.
I walked slowly towards him and joined him under the covers. I felt empowered because I knew I was in control of the lovemaking that night. Next, I positioned myself on top of him and started kissing his lips.
Our tongues danced, and I could still taste the wine on his lips. He pressed me against his body, and I could feel his hard cock between my legs. He slipped my lingerie over my head and started sucking on my nipples. And he reached out under me with one hand and started playing with my pussy.
Now I told him to roll over, and I started licking his asshole while my other hand played with his manhood. He was ready, and I grabbed the strap-on and put it around my waist.
Now I started grinding my body on his back. “Can you feel that, honey? It’s ready for you.”
“Oh yes, put it in me, honey,” he pleaded.
I told him to relax as I spread his legs apart. He was lying face down on the bed, and I slowly entered him from behind. He was very tight, and I thought it was normal because it was his first pegging experience. I got aroused, and I couldn’t wait to put the whole penis inside him. But I knew I had to be careful.
I slowly put the dildo inside him in a gentle push and pull movement, just like he does when he’s giving me anal sex . He was moaning and groaning with pleasure. I told him to let me know if it was painful, and I’ll stop.
“Oh please, baby, don’t stop. Put it all in. It’s so amazing!”
I finally had the whole dildo inside him, and I started to push and pull faster. His asshole was beginning to adjust to its size, and soon, I could feel him relax. I pulled out and told him to change position. This time, I wanted us to do it doggie-style.
I could see his butthole looked a bit sore, so I applied more lubricant and told him to relax. Then I grabbed his hips, raised his ass, and slowly re-entered him. As soon as I had the whole dildo inside him, I started pounding on him. Once in a while, I would slap his butt, and he would moan in delight.
I was aroused, and I started playing with my clit as I continued to push and pull inside him. He was close because of his breathing and all the sexy noises he was making. I withdrew from him, and I told him to lie on his back.
Now I was on top of him, and I let him suck my tits and caress my breasts. I put more anal lube on the dildo and told him to lie down, spread his legs, and raise his butt with his hands. He did as I told him, and once again, I slowly entered him.
It felt so good because I could feel his balls brushing my pussy every time I pushed and pulled inside him. There were moments when I would slowly pull out and enter him again with one swift push.
I grabbed his rock-hard cock and started masturbating it while pushing and pulling out of him. Tim was moaning and groaning with ecstasy. I felt his anal muscles contract, and as he screamed with orgasmic pleasure, his warm white cum spurted out of his cock and into his stomach. I licked the warm liquid, and his body shuddered.
He was still panting when I took out the dildo, which he grabbed from my hand. I watched as he put it around his waist and put some lube on it. He guided me into the doggie-style position, and as his hands squeezed my breasts, he entered me from behind with the dildo.
It felt so good and wet as the lube mixed with my vaginal juices. Tim shoved it inside me, and it reached my G-spot. I was tingling all over, and as he pushed it again, I climaxed. I let out a scream and collapsed on the bed.
He took off the strap-on and lay down beside me. I put my head on his shoulder, and he hugged me close to his warm body.
“Thank you, baby,” he whispered and kissed my forehead.
I kissed his lips and asked, “So, how was it?”
He smiled and said, “It was one of the best orgasms I ever had. That dildo felt good inside me, and I could feel my muscles stretched to accommodate its size. It was a little uncomfortable at first, but the lube made the whole process painless. Once my ass adjusted, I started to enjoy every push and pull until I got the prostate orgasm.”
We laughed, and I knew right there, and then we would have pegging as one of our regular lovemaking practices.
Pegging is anal sex for men. The female partner penetrates the male wearing a strap-on, usually from behind, as he “bends over” like in a dog-style position. Pegging provides a whole new world of sexual stimulation for the male partner, especially prostate stimulation . It also offers exciting submissive role-play opportunities and female domination (i.e., Femdom).
So how do you get started with pegging? Tim and I believe it all begins with you as a couple. You need to have open communication about matters concerning your sex lives. Once you have agreed to try something different, it won’t be so hard to start a whole new adventure in the bedroom. From there, you can start planning on the pegging harness you want to try, accessories, penetration positions, and more.
As I’ve said earlier, pegging isn’t for everybody. Some male friends refuse because they don’t want to be labeled gay. But there’s nothing gay about it . Pegging is a unique way of lovemaking that satisfies both partners.
However, you must do it right. Here’s a quick guide for all of you interested in living out your husband pegging fantasies.
You and your partner must talk about pegging . Anal play, especially among men, can entail discomforts and even pain, especially for beginners.
Talk beforehand. Ask your boyfriend if he is okay with the idea of pegging. If not, don’t insist on it. Respect is still more important than sex.
It’s also vital that you talk while pegging. Ask your man if he’s comfortable or if he wants you to stop. Keeping communication lines open while doing the act can help both of you relax and enjoy the whole thing.
You can talk about adding more lube, less pulling and pushing, changing positions, and more.
Finally, it helps if you also talk after doing the deed. You can share and exchange impressions on your first pegging experience so you can perform better the next time around. You can offer suggestions like trying out other toys, lubes, or experimenting with various positions.
Having a dildo stuck on their anus isn’t every man’s dream, and some are intimidated by the idea. So how do you get your man comfortable with anal play? The best strategy is to start on your own.
You can practice by putting your finger inside your man’s anus. Use a lot of lubrication to avoid pain, or better yet, use latex gloves.
Another good idea is to experiment with a prostate massage or a prostate massager to have a feel of it. If your man feels comfortable with it, it won’t be hard to have that strap-on inside him. Let your boyfriend or husband explore on his own. Be patient because sooner or later, he would agree to the idea of pegging once he’s ready.
The girlfriend is more in control during pegging, and as such, you have to be responsible enough to know your man’s anatomy. You should also be aware of the basics of safe anal play, and you can look up information about the man’s anus and prostate gland .
If you’ve been together for a long time, like Tim and I, you have an idea what turns him on. I know Tim loves it when I masturbate him; that’s why I am doing it during our pegging sessions.
Finally, you need to talk to during pegging because your man can instruct you on how far you should go in, which way to strike, and more.
I think it’s a must that both you and your man shop together for the best strap-on. In particular, the wife must be comfortable wearing it, and at the same time, the man must be okay about having it inside his butt.
Pro Tip: Let the woman look for the appropriate harness and let the man decide on the size and shape of the dildo.
After all, you’ll be putting it inside him. As much as women love to have the biggest and longest dildo they can get their hands on, this isn’t the case with men, especially if they’re trying pegging for the first time.
Once you have agreed on your strap-on, time to look for your desired lube . Luckily, there are many lubricants in the market today, but it can never go wrong with a water-based lubricant. Some couples also use condoms on their dildos.
If you are new to the strap-on world, we can recommend this harness kit from Lovehoney . It comes with a 5″ dildo and fits beginners and experienced people alike. We have had it for a year now, and it’s been a lot of fun!
Before we had our first pegging, I tried the strap-on solo first because I wanted to know what it felt like. In addition, I wanted to ensure it fit perfectly since I didn’t want to spend precious time adjusting it while Tim waited.
I adjusted the straps and took a quick look in the mirror because I wanted to be confident while wearing it without sacrificing my comfort. I also started playing with it, pretending it was Tim’s cock.
The solo-play helped me familiarize myself with the dildo and imagine what it would be like inside his butt. I experimented by practicing some movements I intended to use during our pegging.
Like any lovemaking, you have to start with steamy foreplay to get yourself in the mood. You have to push the right buttons, and once you’re both ready, that’s the time to do it.
Some couples like to start with penile-vaginal sex then move to pegging, while others, like Tim and I, a little warm-up is all you need.
Remember, pegging isn’t like those porn scenes, so take it slow. Taking it slow will ensure the best pegging orgasm for your man.
Getting him into the proper position helps tremendously. Many guys find it uncomfortable and even painful, but you’ll both make it with appropriate foreplay and position.
Don’t shove it inside him right away. Instead, put the tip of the dildo outside his anus and slowly make your way inside. Remind him to relax as you enter him little by little.
Make sure you also apply a lot of lube to allow the dildo to enter gently without harming his anal tissues. Avoid pulling it out fast unless he asks for it. Once your hubby has adjusted, you can start moving back and forth or even grind in a circular motion.
When pegging my man, lubricant is a girl’s best friend. Apply a generous amount all over the dildo before putting it inside your partner.
Pay attention to the tip of the dildo because you’d want enough lube in there to be able to stick it inside your man without harming him. Be sure to reapply lube in between pegging sessions, especially when
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