Until recently, the last time I received anal sex was in 2012. A one point I thought there was something wrong with my anus from having too much anal, so I stopped because of that (turns out it’s fine), but it was mainly because I started to realise the double standards around anal, and how some men were expecting us to be willing to be fucked in the arse, when some of them would freak out if you even tried to put a finger in there. So I made a rule not to let a guy fuck me in the anally, unless he was willing to let me fuck him anally. I still allowed fingers and thumbs (and some anal beads one time), but for 5 years no dick crossed the threshold.
I bought a strap on because it was my dream to peg a guy, but the only time it ever got used was when I had sex with women. One day in early 2014, a guy I had fucked a couple of times asked me to use it on him, but I wasn’t mentally prepared for it, and we hadn’t had sex for a while, so I said ‘just fuck me first and then maybe we can do that after’. Sadly that time he came really quickly, left, and I never saw him again. I regretted not doing it for ages. But maybe it wasn’t meant to be with him. After all, your first time is supposed to be special.
I’ve heard the line that a lot of straight men don’t want something in there because they think it’s a bit ‘gay’, but that’s bullshit. Also, have you ever heard a straight woman say they don’t want to receive oral sex because ‘that’s what lesbians do’?! No, of course not. The irony of men wanting to fuck women in the arse and not wanting it in return is that men have actually got a g-spot up in there and WE DON’T. One of my female friends recently received anal for the first time from her male partner and afterwards when she said it was just ‘ok’ he said ‘but don’t you have a prostate up there?’
I blame mainstream porn.
Anyway, I enforced my rule very well, until my crazy sex night in March, then in April I started dating a guy from Tinder. We had sex on the third date (I know I said I was going to wait to get to know someone more first, but I wanted to fuck him too much to wait any longer). He put his finger inside my arsehole, and the next time I put my finger in his. I asked him whether he would let me fuck him with my strap-on, and he said ‘probably’, and I thought he might, because he seemed very sexually open minded, but I wasn’t totally sure. But on the 5th date, I was super horny, so I fucked the rules again, and told him he could do it to me.
I know some women, who have said that anal can feel quite good – perhaps their vaginal wall is quite thin, so it’s more easily stimulated, but some others do just find it uncomfortable. For me, I quite enjoy the fact that it hurts, and that it’s causing me pain while giving them pleasure. It was nice that he fingered me for a while first and used lots of lube though, which meant the pain wasn’t overwhelming, like it has been in the past sometimes when guys just stick it in.
On the 6th date, he came to one of my gigs (I did my anal sex joke about the double standards), and then when we got home I asked if he really was going to let me do it to him. He said ‘What now? Ok.’ and having learnt my lesson from my last missed opportunity, I did not waste any time in getting out some lube and starting to finger him.
I sucked his cock while putting my fingers inside and eventually worked my way up to four fingers. My strap-on is quite thick, so he definitely needed this. I had previously searched online for good positions for pegging, so decided to try some of these out. One of them was him lying face down (which I particularly enjoyed because I could pull his hair while doing this), and the other was me sitting on the edge of the bed while he backed onto me.
We did briefly try him lying on his back with me on top but he found it too painful, which is a shame, as I wanted to be able to look him in the eyes while fucking him. I didn’t do doggy style, as a man in that position doesn’t really appeal to me – I like my men to be submissive, but not that submissive. But I would have liked to try some other positions, maybe lying on our sides or standing up against a wall, or fucking him over a table while pushing his head into a container of water. You know, all the classics.
I found it quite difficult to fuck him and stimulate his dick at the same time, and I definitely think he enjoyed the fingering and blow job more than the actual pegging, (enjoying the foreplay more than the penetration – welcome to our world), but obviously it was my first time doing it to a guy, so there is still lots to learn. The best thing about it was that he trusted me enough to let me do it to him, and was willing to let me live out a fantasy.
Obviously the main difference between a woman fucking a guy with a strap-on and a man fucking a women’s arsehole, is that the strap on is not part of me, so I am not getting the same physical enjoyment. My strap-on can vibrate, but this was not close enough to my clit for me to feel the effect from it. So for me, fucking a guy like this is more of a mental turn on. It did make me feel powerful, and happy that even though I had let him do it first, technically I hadn’t broken my rule again.
In my joke, I say that it’s my dream to do it while listening to the Spice Girls, because that’s true Girl Power, then I say I’m only joking – I’d do it to Blurred Lines, as that would be more appropriate. But there wasn’t really a right moment to stop and open up Spotify to put on my pre-prepared Spice Girls/Blurred Lines playlist. I also think it would be fun to dress up while doing it, in heels and my dominatrix style dress. Maybe next time I can do all this. Hopefully I will get to do it again in the future, whether that’s with him or with someone else.
So in the words of Gabrielle, dreams can come true, and yes, it’s not always when or exactly how you expect them to, but I’m glad I have finally found a guy not constrained by gender norms and expectations, and not afraid to try something new…