My First Strapon

My First Strapon

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As a serial sexual experimentalist, I’ve always followed the “try anything once” mantra, which, quite often, results in me liking things so much that I further incorporate them in my sex life. This is exactly what happened with my first time using a strap-on. Let me give you a sneak peek into a night of complete empowerment, awkward humping, figuring out what my hips can actually do (spoiler alert: they don’t lie) and asking my partner if they’re okay about a thousand times. Here we go.
I’ve pretty much been submissive for the biggest part of my sexual encounters. Giving the other person control of your body and letting them dictate the rules, as well as the speed and intensity of the penetration itself, felt quite liberating and, I’ll be honest, allowed me to feel pleasure while doing my favourite thing at the same time – lying down and being lazy. It’s a win-win situation, isn’t it?
As time went by, however, I felt the need to experiment more and more and explore new sensations and scenarios both for myself and my partners. I’ve slowly discovered my dominant side and finally felt what it’s like to be on the other spectrum of the sexual act. I realised I actually love being in charge. It’s a whole new level of empowerment, and I’ve found it incredibly arousing too – from gentle impact play to more intense BDSM activities and even humiliation. Alongside these lines, I got to explore pegging too. As a cisgender woman, this was entirely new to me, and felt like nothing I had experienced before. It gave me a great perspective on what it’s like to be the one who’s penetrating the other and almost answered my (and every girl’s) lifelong question about what it’s like to be a man and have a penis… yes, almost.
If you’re a woman, and you’ve been wondering how to bring it up with your male partner, I’ll tell you a little secret: most of the men I’ve been talking to absolutely love pegging. It’s exactly the same as my desire to explore what it’s like to be on the giving side – in this case, the man wants to be on the receiving end.
The first time I used a strap-on, there wasn’t a real discussion or planning before that, it simply happened organically. To be honest with you, when my partner asked me whether I’d like to peg him and handed me the strap-on, I silently freaked out. It felt like a great responsibility, like it’s my first time having sex ever… which was, in a way, the truth. It was my first time having sex “as a man”. So many questions popped into my head (I’m pretty sure I must have looked like the “confused maths lady” from that popular meme). How do I put this thing on? What if he’s in pain? What if he makes a mess (you know what I mean)? How on earth should I move my hips? The only way to find the answers to all these questions was to simply try it out.
We went for the missionary position first. I made sure he’s fully relaxed by massaging his anus and slowly (slowly!) inserting one, then two, then three fingers inside him, all while communicating with him and making sure he’s feeling okay. We took our time – there was no rush. After he was ready to take more, I squeezed a generous amount of lube onto his anus and the dildo. After I made sure that we’re both ready to go, I started to slowly push the strap-on (and myself, obviously) inside my partner. I was incredibly nervous and insecure and had to ask him questions such as “Is this okay?”, “Does it hurt?”, “Will you tell me if it’s too much?” every couple of seconds as I basically had no idea what I was doing. Once I got the whole dildo inside him, I started thrusting.
Let me tell you – it was awkward. Dear men, if you are reading this, I wholeheartedly salute you – having a penis and working with it is definitely not as easy as I expected it to be. I had no idea how to move my hips, it simply didn’t come naturally to me. I was experimenting with different speeds and movements, trying to find something that works well for both of us. Only a few minutes, I got so tired that I asked him to change positions, so we went for doggy style. Greatest idea ever.
Doggy style has always been my favourite position, and now I got to experience what it’s like to be on the other side; to have your partner under your full control, to dictate the speed and the intensity of the thrusts and, therefore, his pleasure. It feels incredibly empowering and satisfying. The rush you get from it is so strong that eventually it starts to feel like it is your own (real) penis, with all its nerve endings and a whole plethora of erotic sensations. My femdom fantasy had finally become reality.
My partner was really enjoying it too. His moans and the way he whispered “fuck” under his breath made me even more turned on and gave me the confidence I needed to improve my moves and be better for him… and for myself. After all, let’s not forget that the male G-spot is the source of the most mind-blowing orgasm a man can experience. What better stimulation than that?
Despite the overwhelming awkwardness on my side, the overall experience was extremely satisfying. So satisfying that I kept doing it with different partners and, in time, slowly became better and more confident in myself. Knowing that the other person is enjoying it is, without a doubt, amazing but the biggest win for me was the fact that he, as a man (I haven’t used a strap-on with a woman yet) was able to overcome the social stigma and the wrong, but still popular, idea that men who like to be pegged are gay. Trust me, this has nothing to do with sexual orientation and everything to do with… yes, pleasure. It’s what we all want, isn’t it?
Now go put that strap-on on and enjoy the ride.
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