If you haven’t read the previous post – check it out before you read this one.  🙂

This is Alex’s response to the last post:

Hey again!
Thanks for the massive reply. It’s a lot to take in, that’s for sure.
Okay, firstly with me being a top, it’s something we have been discussing because I’m so unsure when we do it. In the year we have been together, we’ve only done anal four times, with many many failed attempts between. I get worried that he’ll lose interest soon, which is why I want to fix it.
That being said, I’d love to learn how to top. I think my partner and I would love being versatile with anal, because similarly to what you were saying, its fun to experiment and change position. But the furthest we got was two of my fingers. This is why I bought the toys. To help him try and go at his own pace, which really excited him!!
He’s currently overseas for two weeks, so this is the perfect time for me to try and perfect being a bottom so I can have a nice long hot session with him once he returns.
The big reason for my reservations in contacting you is I don’t really fit the twink stereotype. I’m a little chubby and not at all like the guys you post about.
Thanks again!
I look forward to a reply 🙂

So just to clarify the goal is for both you and your boyfriend to become versatile? Too easy. 😉

As I mentioned it is so important to get comfortable with playing with your own ass first. A good top will take his time to ensure the bottom relaxes, slowly stretches the hole with his tongue/fingers/toys, and doesn’t rush things – but before any of this the bottom boy should have learned how to open himself up with fingers and toys.

From the time you were toilet trained your ass has been clenched tight pretty much 24/7. The only time it hasn’t been tight is when you head to the bathroom to drop the kids off at the pool. And that’s more of a “force it through” rather than “relax” kind of action. It takes quite a bit to overcome about two decades of clenching your ass. Practise.

Of course there are exceptions to every rule. I know there are boys out there who have never played with their butts who met a guy who fucked them long and hard the first time while they loved every second of it – but they tend to be in the minority.

So as I said, you and your boyfriend should practice with toys by yourself and then practice with each other with those same toys – exactly the same toy will feel very different in your ass when you are controlling it verses him controlling it.

While anal sex is the goal – playing with fingers and toys is awesome fun. Go and get yourself a small box of latex gloves and lube (available at any supermarket). Take turns lying on your back with your head on some pillows and your legs spread. Decide in advance that there won’t be fucking – it will take the pressure off both of you and you’ll have a good time. The boy lying on his back should stroke his cock while the boy sitting between his legs should glove up and play with his ass. Slow movements. No rapid thrusting in and out. Communicate. The boy with the fingers in his ass should let the fingerer know what he is feeling. This should be fun. Remember you can’t spell glove without love. 😉

I don’t just play with twinks – I play with all sorts of guys. I’m attracted to young guys with a wide range of looks. So do I get to see a photo of you and your cock?

I think I should film an instructional video for soxster.com on ass play for beginners. No faces. Just a close up of an ass as I use fingers and toys on it – show off some of my technique. Want to volunteer? 😉

Haha I’ll attach a photo of both. One sec!
(photos were attached – and they’re for my eyes only)

You need to work on your confidence. I think your body is great. I love younger guys who are a little chubby with hair. Very much like me at your age. You definitely have the body of a young man rather than a boy. You’ve got a bubble butt thing happening and your cock isn’t  small – definitely within the bounds of normal.

You’ll have no problems fucking with that. 😉


This email exchange has been a good opportunity for me to reflect on how much I have learnt since I was Alex’s age.  I think that it shows the important of gaining sexual confidence. As you learn to take things up your butt, and learn to play with others, then you gain experience and gain confidence.  Sexual experience plays an important role in making young guys more confident in both in the bedroom and in life in general.  🙂