My girlfriend, Sarah, and I were sitting in bed one night when she started to talk about her friend, Cheryl. We both work long hours at the office. Even though we work in the same building, most of our conversations happen in bed. You know, we ask each other about our days, how horrible our bosses were, everyday couple talk. But I never thought we’d talk about first time strap on sex.
“Cheryl had strap on sex last weekend with some guy she met online!” she said with bewilderment.
“Oh yeah?” I replied, my eyes glued to Antman playing on the tv. Man, if I could shrink like that, the first place I’m going is Area 51.
Sarah’s body turned towards mine, demanding my attention. “Yeah, she said it was a little weird at first because she never had to thrust like that before. But it’s apparently a really fun experience.”
I knew where she was going with this.
Sure, Cheryl had a good time, but my butt is a no-go zone.
What straight guy would allow their ass to get penetrated by a giant dildo?
“Are you sure the guy was straight?” I asked.
“Of course, he was straight. Strap-on sex doesn’t mean you’re gay,” she replied defensively.
I took a deep breath, “is this something you want to try?” I paused in silence, waiting for her answer.
“Well,” she said nervously, “I am really curious about it. I thought we could try something new – it sounds like a lot of fun.”
“Why this? Out of all the things we could try, why this?”
“Well why not. We’ve never done it before, I would love to try role reversal, and the male G-spot is in the anus.”
Really? I didn’t want to look curious, so I told her I’d think about it.
That night while she was asleep, I did a little research online and found a strapon sex guide. What sparked my curiosity is the male G-spot.
I didn’t know it was in the anus. Does this mean it’s going to feel good? Are my orgasms going to be even better?
Sarah had the day off the next morning, so I wrote her a note and left it on my pillow.
“To do list: go get a strap-on.”
A couple of hours later, she sent me a photo of the strap on toy kit, with the message, “Can’t wait to see you!” To be honest, I was really excited. The minute I got off work, I basically ran home.
When I got home, Sarah was on the bed, waiting for me. I climbed on top of her, kissing her passionately. She sucked her finger and then slide it into my ass, massaging it slowly. I could feel my body loosen up and I was excited to give this a try.
After a couple of minutes, I got off the bed, grabbed the kit, and handed it to her.
Sarah came out of the bathroom with the strap harnessed around her waist. It wasn’t so scary as I imagined. “Listen, I’ve been doing a lot of research about it today, so I think I have a pretty good understanding of it. The most important thing is you tell me if it’s uncomfortable or painful.
Don’t try to “take it like a man,” got it? Use the safeword red if you want to stop.” I nodded in agreement, “got it.”
She lathered the dildo up with lube and laid on her back.
“Wait,” I said, “aren’t we doing it in doggy style?”
“No,” she shook her head, “that’s for more advanced people. I read that doing it cowgirl is the best for beginners.” I climbed on top of her and straddled her with my legs, we both giggled.
“I’ve never seen you from this angle before,” she said.
I took a deep breath and slowly slid the dildo inside of me. Was there pain? No, but it definitely didn’t feel comfortable at first. Sure, she did everything right and used lots of lube.
But nothing can explain the initial feeling of something going up your ass.
I didn’t move for the first couple of seconds as I was adjusting to the new feeling. Then slowly, I slid up and down the dildo. Not too deep, just enough to ease into it. Sarah had her hands on my thighs, lightly pressing into me.
I picked up momentum and a tingling feeling ran through my body. So, I started to go deeper and faster, the sensations streaming up my body. I couldn’t stop and I was jumping like a yo-yo.
Knew I was about to orgasm, and that’s something I didn’t want to miss out on. “I want you to come for me,” I heard Sarah say. That was all I needed to hear. I expected a usual orgasm, but this one was different. It exploded throughout my whole body, paralyzing me for a moment.
I had reached pure bliss. Something that’s never happened to me before.
Sarah looked at me, and I looked at her in silence. I didn’t know what to say; I couldn’t think of words at that moment and I was emotional.
“So, how was the first time strap on sex?” she asked.
I removed the dildo from me and laid next to her on the bed.
“Amazing.”
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Strap On Frenzy!
After that night, I couldn’t stop thinking about it. It honestly surprised me how much I enjoyed it, and clearly I’m not the only one. There’s a lot more interest in strap-ons lately, especially with more couples trying out pegging.
Maybe it’s becoming more talked about, or maybe scenes like the one in Deadpool made it feel a bit less taboo. Either way, it definitely feels like something more people are open to trying now.
For anyone new to it, pegging is when a woman uses a strap-on to penetrate her partner. Simple in theory… very different in practice.
After going through it myself, I realised pretty quickly that having the right gear actually makes a huge difference. So if you’re thinking about trying it, here’s what I learned.
Harness
One thing I didn’t expect was how many different harness options there are. When Sarah came out wearing hers, I remember thinking it looked way less intimidating than I had imagined.
There are simple strap styles, and then more styled options like corseted designs. Materials vary too — vinyl, leather, cotton, even denim.
From what I’ve seen (and heard since), leather looks great and feels sturdy, but it can be harder to clean. Something softer like denim or fabric seems a lot more practical, especially if you’re just starting out.
I’ve come across a few solid options, but honestly, something like the Fun Factory harness seems like a safe bet:
- Soft and comfortable
- Easy to clean
- Still looks pretty damn good
- Secure fit with proper straps
Or, if you’re feeling creative, you could even experiment with rope and make your own setup!
The Dildo
This is where things can get overwhelming. There are so many options — sizes, shapes, realistic or not, vibrating or not.
After my first time, I realised pretty quickly that size and comfort matter more than anything else. You don’t want to go too big too fast — trust me.
But the biggest thing I didn’t think about at first? The material.
If you’re going to use something like this, it needs to be body-safe. Silicone is usually the best option. It’s smooth, safe, and easy to clean. Definitely worth making sure your dildo is phthalate-free.
I ended up learning that phthalates are chemicals you really don’t want in something that’s going inside your body, so that’s something I’d never ignore now.
There are a few brands that kept coming up while I was looking into it:
- Tantus — lots of options, different sizes and styles
- Fun Factory — a bit more unique in design
- King Cock — more on the realistic side
- Evolved — good range and solid quality
If you want vibration, there are options like FemmeFunn or Uprize that add a completely different layer to the experience.
Another thing I didn’t realise at first
A flared base is important. It keeps everything secure in the harness and makes the whole experience safer and easier.
O Ring
This was something I didn’t even know existed before all of this.
The O ring is what holds the dildo in place, and it actually matters more than you’d think.
Rubber ones stretch, which makes them easier to use, but they can wear down over time. Silicone or metal ones feel more solid, but you need to match the size properly.
Honestly, if you’re unsure, it’s probably worth asking someone in-store instead of guessing.
Strapless Strap-on
I didn’t try this myself, but I definitely went down the rabbit hole reading about them.
They look like a regular dildo, but one end is designed to be held in place internally by the wearer. That means both people get stimulation at the same time.
From what I’ve seen, they can be a bit harder to control, but they offer a more connected experience. Some people still use them with a harness for extra stability.
Hollow Strap-on
This one surprised me the most.
A hollow strap-on is designed to be worn by someone with a penis. It allows you to change size or shape, or even keep going after finishing.
It’s not really about “fixing” anything — it’s more about changing the experience or adding something different.
Some options even allow for double penetration or hitting angles that are hard to reach naturally.
Also, I didn’t realise this at first, but it can be helpful for people dealing with erectile dysfunction, since it doesn’t rely on staying hard.
Finally the Rest
If there’s one thing I learned from all of this, it’s that there’s a lot more to strap-on play than I expected.
That first experience completely changed how I looked at it, and having the right setup made a huge difference.
There’s a ton of variety out there, so going in with at least a basic idea of what you want will make things a lot easier.
If you’re curious like I was, it’s definitely worth exploring properly.
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