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A talk withh James Oakleigh about DILDOS, PLUGS & ASSPLAY.


MasterMarc: Hi James. Today we will talk about big assholes and how to play with. 🙂 Hope I don’t offend you, if I’ve invited you as specialist for this topic.

James: Hi Master Marc, thanks for having me. No offence taken, I’m quite honoured to be considered a specialist.

MasterMarc: We talk today about ass play. When have you started to play with your butt and what is the fascination to play with toys?

oakleigh-assplay-161117-005James: So it all started when I was a teenager, growing up and being curious. I don’t know what started it off but from a very early age I was fascinated with the pleasurable sensations I could get from playing with my ass. I just started with simple things like a finger, a golf ball, basically anything I could find around the house. If I could make it fit, it went in my ass. I then discovered the internet…

I found out about the “male G-spot” and regularly started to milk my prostate, this went on for a number of years until I hit 18. It was then that I ordered my first dildo, from that moment I was hooked.

My curiosity was always getting the better of me, leading me to try things that were bigger, wider, deeper and then of course I found one of the most amazing things ever. Fisting!

MasterMarc: There are many different dildos, plugs etc on the market. What categories would you differentiade and can you tell us about different sensations you get with it? Probably you have also some advices for guys who are starting to discover the endless darkness of their butts?

James: So I would categorise butt toys into three different categories, just to keep it simple. Fuck Toys, Width Training and Depth Training. I would define them like so.

Fuck Toys:- Does what it says really, something a bottom boy can ride and fuck themselves with to simulate the pleasure of and actual fucking. Although naturally, it doesn’t quite compare to a guy grabbing your hips and pounding away till you both get that sweet release. I enjoy using these to start with, however its not long before I’m gaping and needing something bigger.

Width Training:- I would put any wide and sizable dildo, butt plug or inflatable into this category. Width Toys are something that I used quite a lot to help train my ass for fisting, I love the feeling of stretching myself with ever increasing width. Riding them up & down, feeling yourself get stretched out is a sensation I love. I especially like to ride them very fast, almost like being punch fisted. The sensation of blooming a rose bud is ecstatic.

Depth Training:- These are toys like colon snakes, double ended dildos and depth plugs. I’m training my ass with these a lot at the moment, trying to open up my second hole so I can achieve my goal of being fisted elbow deep. I love taking my colon snake all the way, watching it bulge through my stomach. Its a hard sensation to describe but it’s one that I genuinely love.

The best advice I can give to those aspiring ass pigs is to take your time. If you rush you risk doing a lot of damage to yourself. One thing that’s really important is to douche yourself thoroughly before play. If you clean out your bowl but don’t clean out your lower intestine, you might find your second hole doesn’t want to play ball. And you wont get any deeper than maybe 6-10 inches.

There’s lots of advice I can give, but the most important thing is to relax yourself and make sure your butt is empty to accommodate the massive toys you’re about to enjoy.

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MasterMarc: If we talk about assplay and not about fisting would you say, that you prefer to do the assplay by yourself or do you prefer if another guy has the controle about the plugs and dildos? Isn’t it a little like wanking, that nobody can do it as good as yourself?

James: From my personal experience I find that if I play with my ass myself, I open up and gape really quickly. Where as if someone else is in control, I really have to focus on breathing and relaxing.

Ultimately though, I generally tend to prefer it when another guy is in control of the plugs and dildos. I guess that’s my natural submissive side coming out.

One experience I’ve had with a guy which I’ve never replicated myself is a prostate massage. I can find my own prostate and milk myself, but it doesn’t compare to the ecstasy this guy put me in when he just teased and milked my P-Spot.

I guess I’m a needy bottom boy and need a guy to take charge of my ass for me.

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MasterMarc: As master I am happy that boys like you love to be out of controle. But now I have really to ask you, if you like the combination of assplay and bondage?

James: 100% YES! I love a good kink session and exploring my sub side. Love all sorts of weird and wonderful kinks, some things people couldn’t even begin to imagine.

One thing I find rather hot and very arousing is being restrained in tight, restrictive and compromising positions. Then having my ass worked and stretched. Something I once had done to me was to have my legs bound to my thighs so my ass was exposed and had my hands held behind my head, then had a blackout hood put on me and an anaesthetic mask held over my mouth and nose feeding me poppers. Although it was all consensual I had no control over what was happening to me, I was forced to get into a submissive headspace and have my ass well and truly wrecked.

It was one of the most intense and pleasurable experiences of my life, I’m very keen to replicate it.

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MasterMarc: I can imagine that you like it this way. You have told us before about your second hole, which is, to be honest, one of most interesting parts to play with as fisting top. How is it with the toys? I can imagine that it is not so easy to get there and to bring it up, as it is hidden behind a left curve.

James: The second hole is the best part for me, its something I’ve found has given me sensations I’ve never felt before.

I really want to be able to take a fist deep into my second hole, up to and maybe past the elbow. I don’t know why but it’s something I’m fixated with and hell bent on achieving.

With the use of toys I find its very easy to get into and through my second hole, I just use lots of lube and patience. I tend to start with long and skinny colon snakes, slowly working my way wider and wider. I highly recommend aspiring bottom boys try it.

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MasterMarc: I think we have to talk again soon, James. But for now I want to close the interview with the question about other important advices you can give?

James: Most definitely, I really enjoy talking about my kinks and fetishes. Sadly I don’t get to do it often.

Final advice I can give when playing with your ass is to listen to your body and look after yourself. If something hurts, it hurts for a reason. There is a difference between pain and discomfort, its important not to get these two confused in the pursuit of  ass destruction. Take your time and you’ll have a lot of fun.


You can contact James on Twitter.

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