The Anal Trainer Challenge: Week One

So, I have been nominated by my fellow colleagues to take the Anal Trainer challenge. Over three weeks I’ll be working my way through the Colt Anal Trainer Kit in an attempt to broaden my sex life. It was pretty much a unanimous decision in the office that I should be the one to test this out because:

A: I’ve never been a bottom before.

B: I’ve started dating a guy who wants to fuck me.

C: Apparently I wince every time we get a new batch of dildos in.

Day One: I’m all ready for the first day of the challenge. My colleagues waved me home with my training kit and some Liquid Silk. The first plug measures 4.7” in length, starts off at the size of my index finger (see picture) and widens to roughly the size of a small carrot. I’m lubed up and mid wank, so as ready as I’ll ever be. Pressing the end of the plug against my hole feels good and slowly but surely it’s making its way. I’m getting into in now and push a little harder. I’m starting to wonder what I’d been making such a fuss about, this was feeling good! I soon climaxed and pulled out the plug placing my fingers next to my hole so I could measure how far I’d got. Just under an inch. Not quite as impressive as I first thought, but a start at least.

Day Two: Right, with a fresh new confidence for arse play, I’m feeling that I can take a significant amount more tonight than I did before. As before, I warm up and make sure I’m well lubed. I go for the plunge, things are feeling good so far, I pull it out just to see how far I’ve got this time. Again, just under and inch. I work up a rhythm with the plug then force it in as far as I can. It hurts. A lot. I think maybe I’m trying to run before I can walk.

Day Three: A well deserved day off for anal recovery.

Day Four: After telling someone in the office about my last disastrous attempt with the plug, he’s suggested I use some anal relaxant (as his nick name is “Fisty” I think he probably knows what he’s talking about). Using Pjur’s BackdoorRelaxing Anal Glide a 2-in-1 lube and relaxant, I get to work. Learning from last time I push as much as I can but as soon as I start to tense I stop until I’m more relaxed. After I’d cum, I took the plug out and I was about half an inch away from getting the whole plug in. Good work!

Day Five: Today was the day! Taking this little plug has become a bit of a routine this week, so I was just going about my business (still using the 2-in-1 relaxant) and just enjoying it without even thinking about how far in it was. Then, all of a sudden, it reached the tapered part before the base. It was completely in, but also felt great! Giving it a wiggle once inside gave a great sensation and it wasn’t long before I came. So the week one challenge is complete, although I can’t help think that I’ve got to go through all the same trials again next week with plug number two…