Sex Diary : My first time pegging a man

The moment has come. These last few weeks have been filled with this holiday atmosphere – even though I have a lot of work to do – and I have to admit that I’m having a lot of fun. Beach, friends, ice creams and sex. A lot of it. A friend and I were talking and the subject of pegging came up. I told him I’d like to try and he said yes… I will guide you through the whole process. Brace yourselves!

1. “It has to be small”

Size does not matter. However, my friend’s prerogative was all about size. “It has to be small” he said, while I was browsing strap-ons and dildos online. He already felt vulnerable just talking about it, somehow I already had the control. I told him straight girls don’t really have a choice when it comes to dick size – WYSIWYG – but I figured I would buy something small and go slow. So I headed to the sex shop and bought a strap-on with a tiny blue dildo that looked like a chewing gum sorbet – or a melting smurf. Everything was pretty expensive so I bought an ok one, but not the best – I mean, it’s not like you can return it after using it… When I arrived home, I sent him this picture…

2. “Be gentle”

The time came and my friend arrived at my house, with fear in his eyes and a tablet of milk chocolate. We talked for a while, had a few drinks, and headed to the bed. I could already feel kind of powerful as I told him to strip, but we were also both super nervous and uncomfortable, since we didn’t really know where to start. We fooled around until he got on all fours. I felt like his fate was in my hands, which I covered with lube. It really felt like I was taking his virginity, which is really weird because he’s older than me and I think has more experience than me.

I went super slow, prepared him and finally penetrated him. However, I’m a short girl, so we had some angle issues. I ended up putting some pillows under my knees. We started again and it was going really smoothly, so smoothly in fact that I couldn’t even hang on to his hips to keep the rhythm since there seemed to be lube literally everywhere. It was a mess. I also realized I have a do more cardio exercizing because fucking is tiring! I used a few muscles I didn’t even know I had.

(Photo by Coiled Up)

3. The Shift

The whole experience was actually very powerful. I deeply felt a shift in perspective and felt like I was a man, moving like a man, fucking like a man. His head was on the pillow and I was fucking him and I could feel pleasure, in my head and in my body since the base of the dildo was thrusting against my clitoris.

We then changed position as he laid on his back. After another pillow shuffle, I was ready and I told him: “Now, you’re going to have to experience what a lot of women experience all the time… Knees up the ears!”. We kept going but we were so slippery and I was sweating out of every pore of my body. We took a break. I remember him being surprised that I used the whole length of the dildo on him and I suggested we switched to a bigger one. He said ok.

4. Just like a man

So I put on my Macchiato and I told him to kneel on the floor with his arms on the chair. That position was much better, we had a good rhythm, we were both more comfortable. He was afraid about the size of the dildo but it went pretty smoothly and he actually enjoyed it. I started fingering myself at the same time and ended up having a pretty great orgasm. I remember laying on this back for a few seconds after climaxing, the same way men had laid on my back in that same situation.

5. Flip

After we flipped and I ended up on all fours and he started fucking me, I was still wearing the strap-on. I remember that we both felt like things were falling into place and we were back into our good old comfort zone. The act of reversing the roles really turned me on and I came again.

6. “It’s right there”

After the sex, we were both sitting on the couch, naked, exhausted, trying to grasp the air from the fan. The dildo was still in my strap-on and I remember feeling this urge to ask him to suck it. That’s how it went:

“So, if you want, you can suck my dick. You don’t have to, of course”, I said

– “No thanks, I’m good”, he replied

– “I just think it would really turn me on…” I said after a few seconds, realizing that I was behaving just like a man – I know all men are different but this is something I could really see identified with men and sex. I was insisting, trying to convince him to suck my fake dick, because, well, “it was right there!”. Of course, no means no, so I took my strap-on off and went to sleep.

Overall, it was a great experience and it was extremely interesting to have a change of mindset and reverse the roles. It will definitely give me more confidence for the future.