One of the things I love about BDSM is teaching younger guys. Always a pleasure to respond to requests for advice received by email (keep them coming):

Hey πŸ™‚ I have been reading your profile for a while now.
And I just saw your beginner post.
My situation is this:
I have a boyfriend.
He’s a top.
I can’t top as I have a less than average size penis.
But bottoming hurts.
I’d also be curious to try some more extreme stuff with him too. I bought some butt plugs, a vibrator etc.. But yeah I don’t know where to start.
Any advice?
Would it be bad of me to ask you for a session with just me?
Thanks in advance,
Alex πŸ™‚

Hi Alex
I’ll write you a long response but first do you mind if I ask how old you are, how old your bf is and how long you have been together?

I am 22, he is 21, and we have been together on and off for around a year.Β  πŸ™‚

Excellent – do you mind if I post your questions and my answers on my blog? Β Pick a fake name! πŸ™‚

That fine!! I’d be honoured πŸ˜›
And ummm Alex will be fine as the name haha

Well ‘Alex’, you’ve raised a number of issues in your email – so let’s take them one at a time.

You mentioned that you can’t top as you have a less than average size penis. Even guys with really small dicks can successfully top. It doesn’t necessarily mean that you’ll be able to fuck guys in every possible position – there are certain positions that do require a longer cock. But there are plenty of positions that guys with small cocks can use to pound really effectively.Β  One of the advantages of a small cock is that you can really attack the hole rather than going for depth. If you rabbit fuck someone and pull all the way out and push back in with each stroke it will definitely be a good experience for the boy whose ass you are abusing.Β  So don’t worry about the size of your dick – you can absolutely fuck, you just need a partner who is willing to experiment with you to find the positions that suit you.

Which brings me to your boyfriend – who you say is a top. If he is a top then he probably won’t be the right person to experiment with to find out how best for you to fuck as a top. If you two decide to open up your relationship to other partners then try and find a more experienced bottom who you can experiment with. The right guy will help you try a number of different positions to work out what works best for you. Don’t look at this as being work – it will be a lot of fun. When I visited Fickstutenmarkt in Berlin and fucked more than 20 guys in one night it really emphasised how different positions suit different guys better. Whether you top or bottom, keep trying new positions. Experimenting is fun!

In regard to being a good bottom – it really does take practise and dedication.Β  While there are some boys who can take a cock with no practise, these guys are in the minority. So you’ll need to practise. You should start with your fingers – work yourself up to the point where you can jerk off with three or four of your own fingers in your ass. Then get yourself a toy and use it when you are jerking off. Nothing too large and nothing too small. Aim for something a bit bigger than your boyfriend’s cock.

When picking a toy go to a decent sex shop with a good range. Ideally get something in silicone – it will be easier to clean and you can even boil most silicone toys to clean them. When playing with yourself take plenty of time, use a lot of lube and relax. Just enjoy yourself and learn to appreciate your butt and what it can take. Focus on width not depth.

Getting used to having your ass played with can take some time. A year ago I played with a hot boy in his mid 20s just prior to him going on a working holiday to Canada.Β  He had always disliked anal sex, but during a session with me found that he really liked what I was doing to his ass. My technique was pretty simple – I played with and teased the outside of his ass for an extended period, until he was practically begging for me to side my fingers into him. I messaged him this evening:

Hey there! I’m doing a blog entry on beginners to anal sex and I was wondering if you could write me a couple of sentences on why you liked the time I played with your ass? πŸ˜‰ What did I do right?

Sure! I’m highly inexperienced when it comes to assplay and normally rule it out as it hurts too much and often leaves me feeling physically ill afterwards. It was right with you because you took it quite slowly and I dunno, I felt safe with you. You didn’t do more than I could handle at a time. I was previously very closed to the idea and you have inspired me to want to be able to handle it properly.

So what did it feel like?

It didn’t hurt like it usually does, felt a wee bit uncomfortable but not hugely but I don’t remember entirely, it was a little while ago. I remember the overall after memory, but not the exact feelings

That’s perfect – thanks

I tried it again recently, hated it again. I definitely need your help in being able to take it and I really would like to work up to being able to handle your cock

I’d love that too πŸ™‚

Well that’s a nice vote of confidence.

When you can take a toy with confidence by yourself, then it’s time to involve the boyfriend. Playing with the toys will prove to yourself that you can take them. Then it’s time to give the control to someone else – having someone put a toy up your ass is very different to using it on yourself. Tell him to take it slow and that he should watch your face – not your ass. It might help if he is wearing latex gloves – it will make him feel less self conscious when he fingers you. With any ass play there is a risk that ‘shit happens’. If it does – don’t worry about it – it’s happened to everyone, so don’t make a big deal of it.

In terms of playing with your boyfriend you mentioned a whole lot of gear (butt plugs, vibrators, etc.) but you didn’t mention what sort of scene you wanted. Do you want him to use these toys on you? Do you want to use them on him? Even tops like things in their butts every now and then? Personally, I don’t like getting fucked, but the right toy can feel amazing.

In relation to having a session with me, you’ll need to consider whether we should play with or without your boyfriend. I’m happy to play with you separately or together. I’d love to show your boyfriend how to get the most of your ass. Always love preparing the ass of a newbie for sex.Β  πŸ˜‰