First time Anal Sex and What We Learned

First Time Anal Sex And What We Learned Blog Post bANNER bY vOILET gREY

The first time I had anal sex l I was 23

When I was in my early 20s, I didn’t think I would ever like anal sex, so it was off the books. When discussing it with my boyfriend not long after we first got together, he was very respectful about it, not pushing things and offering that if I ever changed my mind, we can take things slow and try what we’re comfortable with.

As time (and lots of sex) went on, I got curious. I’d heard from friends and random articles I’d read on the internet about how good it could feel. So why not try some anal play, I thought. I discovered I loved over the knee spanking, something I thought I’d hate, so why not try it? I knew my boyfriend liked it, but he’d never do it unless I wanted to. Then one night, we were having sex, I was on top, and the rush came over me.

‘Touch my ass,’ I said.

His hands were on my hips and my behind, but he knew what I meant, and he was thrilled.



He slid his fingers down to there and started massaging the outside. That was as far as I wanted to go.

‘Is that ok?’ he asks. ‘Does it feel good?’

Oh, did it feel good! I didn’t want him to stop. He enjoyed it as well, guiding me through it as we both started to climax. It was clear from then on, I wanted to try anal play, specifically, anal sex. I spoke with my boyfriend and we agreed to wait a while, taking things slow when the first time came.


Note ‘attempt’. Penetration wasn’t achieved, which was what we were looking to do. We knew this wasn’t uncommon, so we didn’t beat ourselves up if it wasn’t to go smoothly.

So what happened? Along with a mandatory truck-load of lube, my boyfriend started off with massaging the outside of my anal area with lube, taking things slowly, gently guiding me through every step. Having anxiety, it’s easy for my body to be more tense than I realise, so for anal sex, relaxing is definitely an effort. Once I got used to that, we agreed to try just the tip of his finger inside me.

‘Relax…That’s it…’

Anal penetration is a very different feeling to vaginal for me. It doesn’t take much for me to feel stretched and filled. After some delicious feeling action with fingers, we wanted to try him being inside me. I got ready, he got more lube. What I found really endearing is while I went to the bathroom (it’s important to use the toilet before and after sex, especially if you have a vagina, to prevent UTIs) he looked up the best sex positions for beginner’s anal sex. As well as my health, he’s a ‘giver’ in the bedroom, putting my pleasure before his own.

We decided to try lying on my front with my legs spread, as we read it was one of the most comfortable, especially for first time anal.

Yeah…it didn’t really work.

Despite relaxing and going slow, we tried on my front, not working. On all fours, that didn’t work. On my back was really uncomfortable. Even lots of lube and relaxation, trying to slide inside me just became painful, so we stopped. Let’s face it, hearing your girlfriend go, ‘Owww, get off me!’ because it hurts isn’t exactly going to inspire sexy time. He stopped immediately, making sure I was ok.

My boyfriend said it’d be best to wait a little while before trying again. We didn’t want to put pressure on ourselves to do something we may not be physically ready for. I wholeheartedly agreed. Despite anal sex being a big turn on for him, he was incredibly patient and never pushed, putting my health and wellbeing first. 

 That’s the thing with anal sex. You have to be patient, even more so with first time anal. There’s no natural lubrication that comes with having a vagina, and even then, I always use lube as well (there’s nothing wrong with using lube, by the way!). Also if you rush, the anal area is easy to tear.


Something I enjoy, and relaxes me enough for anal play, is what I call, ‘Dom talk’.

Being a Switch (a term used in the BDSM scene for someone who switches between dominant and submissive roles) anal sex is something that, being the receiver and being guided through it, triggers a submissive mindset in me.

My boyfriend taking charge in the sack, and being called pet names like ‘good girl’, ‘kitten’, and ‘babygirl’ is enough to send me into am almost blissful state, making partial penetration is much easier.

A few months after our first attempt, we tried again. Again, it was a spontaneous need for him to fuck my ass during PIV sex. Just like the first time anal, I needed him right there and then. I didn’t have to tell him twice. He was up for it.

So we started the same: lube, using fingers, and me on my front but this time, with my hips elevated a bit more. So far so good. Since our first attempt and other naughty bedroom escapades, we realised me having quite the curve in my lower back that can make ‘collapsed doggy style’ a little difficult. So modifications were made. That and of course, a splash of ‘Dom talk’.

‘You want me to fuck your ass?’ my boyfriend asked, easing his finger inside me that felt incredible.

‘Yes Sir.’

Penetration was much easier this time. Starting with the tip, he graced my ears with more dirty talk, relaxing me enough so he could be fully inside me. A kinky first time, lots of ‘good girls’ and calling him ‘Sir,’ which he loved, it was very easy for us to get completely caught up in the heat of the moment. Again, despite some discomfort, the more I relaxed, the more pleasurable it became, both of us getting lost in some very kinky sex. However…


Just like with PIV sex, any after effects of anal sex, whether it is first time anal or not) is something to keep an eye on. Everyone reacts differently.

In my case, despite feeling mentally Zen, wasn’t as relaxed as I thought in my body. I tore a little and bled. Not a great thing to see after some great sex. I also noticed my stomach having gripes around 24-48 hours after the act.

Being careful is something me and my boyfriend put first and foremost since having anal sex. This was also a two way street as my boyfriend is also not small in ‘that’ department and getting lost in the heat of the moment, it’s easier to go at it harder than you think, not realising until after. Let’s face it, when it feels so good, you don’t exactly want to stop.

We had anal sex again a few months later. Perhaps it would be different this time? We definitely went slower, slower than slow. Imagine a snail’s pace, but even slower. Again, it was great, minus again, discomfort in trying to relax (anxiety is a cruel mistress) again, the same thing happened.

It was obvious what we were doing wasn’t working properly. Was I just not cut out for anal? Was I broken? Was my boyfriend just too big for us to do anal sex safely? It wasn’t the first time I had stomach gripes and flare ups, even without anal sex, so something was up.

Obviously with any bleeding, especially after anal sex, it was best to see a GP, right? With more flare ups and pain I’d been experiencing when starting my Master’s Degree, I head to the doctors. Multiple tests and appointments later, I was diagnosed with a condition long suspected: Irritable Bowel Syndrome (IBS).

Turns out, full scale anal sex can trigger symptoms. That coupled with anxiety and an endowed boyfriend, while my mind may be relaxed, my body definitely might not be, leading to tearing inside. OUCH.


Hindsight can be a very good thing. Being diagnosed with a digestive condition answered many of my questions, as well as leaving me with no option to be blasé in many facets of my life.

As you’ve read, we were doing everything I could to be as careful as possible, agreeing that perhaps it wasn’t a good idea if this was the effect it has on me. The last thing my boyfriend wanted to do was hurt me and/or potentially put my health at risk. However, with the diagnosis and measures I was taking, I was looking more into anal sex and IBS. I looked into butt plugs (being a sex blogger, why this didn’t occur to me before I will never know!)

For the most part, we rarely have anal sex (this is different for everyone) only doing so when I felt certain it’s safe to do so (i.e. not having a flare up for a while) and only doing some ‘just the tip’ action. We tried this recently, and as well as having an incredible time, I experienced no negative side effects afterwards! We haven’t since, due to flare ups, but we’re both thrilled finding this happy medium.

Anal sex different for everyone, so find what works best for you and of course, be safe!

One Response

  1. Damn that story was hot and feel bad that you had some issues. Everyone reacts differently like you said. My boyfriend and I do it often, but it’s because I don’t have the flare ups.

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