Question: Hi. I have a boyfriend. We are somewhat together and have feelings for each other deeply. I feel we are on our way to LOVE!!!! We just have one problem: he has a 8.5, thick dick. Giving him orally isn’t a problem. It’s just trying to get penetrated.
I really am I bottom and love to feel a penis inside me. Our first time getting intimate was my first time in a year having anal sex. I tried lubricating and put anal-ese in my rectum for pain discomfort. I couldn’t take any of it. My boyfriend was cool about it, really, and said we can work on sex. I was happy, but a little disappointed with myself.
So, currently while he is away I have been practising lubricating the rectum, while trying (anal-ese) again. I put two fingers in my anus and started penetrating myself. Hopefully trying to get used again to being a bottom and getting penetrated. Didn’t feel that bad! (I had to go to the bathroom a little later, though.)
Question is, what else can I do to make it easier? I want it to be pleasurable for both of us. Should I buy a dildo around his size and start penetrating myself to start getting used to it again and preparing myself. Should I repeat this everyday to get used to the feelings? Anything will help!
The Lovers’ Guide replies:
Yes, it can certainly need a little care and practice to take a big penis inside you if you haven’t had one for a while.
Using a dildo your partner’s size could help – but do take care to go slowly; if you’re feeling pain, that’s a sign you could be causing damage.
On the subject of pain, I really don’t think AnalEse is a good idea. On the one hand, it means you won’t feel if things are going wrong. On the other, do you really want your anus to be numb while you’re having sex? A lot of the pleasure of anal sex comes from the feeling of friction.
With your dildo, and loads of lube, practice taking the big penis/dildo inside in the way that is right for you – both in terms of technique and in terms of your opening up and relaxing physically and mentally. A technique that usually works is to push slightly with your anus against the dildo or penis, as if about to pass faeces. That way, your anus will open up. Of course, you will need to know you’re clean inside when you do this. Douching can help with this, but may not be necessary. Experiment with how you sit, kneel, squat or stand as well: you might find some ways are easier than others.
Remind yourself, with the dildo, about what it is like being a bottom when having sex. Let yourself go with the old feelings – and get ready to enjoy them again. You might even want to do this with your partner there. He might get a kick out of using the dildo on you, then when you’re loosened up you can start to have sex without his feeling he’s hurting you.
Basically, it’s not a question of forcing your sphincters to open out, more of allowing yourself the right frame of mind and using the right techniques. This will include the sex positions which allow you to open up most fully. Some say a deep missionary is best for this; others prefer a doggy style position, with the bum really angled up from the lower back.