Anal Sex – yes / no?

My ass, my cute, little, quite boney ass, has always been off limits.

I like squeezing it into a tight pair of jeans, showing it off in a bikini, swinging it from side it side when there’s a cute guy behind me, but as a ‘back entry’ it’s always been taboo.

It may be because I remember my mom giving me ‘the sex talk’ and anal sex was something that sweet classy girl-chicks never ever did.

But lately I’ve become more and more curious, especially when so much has been written about anal g-spots, the anal orgasm, and mostly – about how so many women love anal sex. Ordinary women, even classy girl-chick ones.

It didn’t seem fair that I was missing out. If there were more orgasms to be had, I wanted them.

But, I was kinda terrified. My ass was virgin territory.

I called up my friend who is also my local Handyman.

‘Hey’, I said. ‘I’ve been thinking about something recently and maybe you’re the guy to help me’.

‘Not another free Handyman job’, he replied, ‘I can’t bear the thought.’

‘Not really.’ I said. ‘This is about my ass’.

It went really quiet.

‘I’d like you to go in me from behind.’

Deathly silence

Oh God I’ve pushed him a bit too far I thought. It’s quite different asking someone to fuck you from behind instead of the usual ‘Please help me, the toilet’s leaking’.

Anyway, he was delighted. He loved the idea so much that he let out a ‘Yes yes yes, let’s do it baby’, which was quite a departure from his usual ‘Violet, are you sure you need to renovate the bathroom?’

Of course he was delighted. No-one likes changing taps. But all men like the idea of sex without any ties. Especially when tight virginal bottoms are involved.

Usually for handy-work I have to book him weeks in advance. But for this, he was available immediately.

I wasn’t. I needed time to think.

We set the date for a week away. Seven pm. His house. He suddenly got very involved and suggested I wear a short leather skirt, high heels and no underwear.

I did not obsess over the skirt, the shoes or the underwear. I obsessed over my ass.

In those seven days I thought about anal sex a lot. I tried to imagine it, dreamed about it, questioned my girlfriends about it, asked strangers what they thought about it, and then on Friday I pulled on my leather mini skirt, slipped on my heels, put on French hand-stitched underwear because I wanted to and as a last minute thought, sprayed Chanel No 5 on my buttocks.

I rang his doorbell, my heart beating a little faster than normal. He opened and I’ve never seen him looking happier in his life. He was not wearing overalls and there wasn’t a hammer or a toolbox in sight.

We drank a lot of whisky and made the rules. Actually, there was only one.

If I changed my mind, we stopped. Immediately.

We drank, we chatted about my house renovations, the tension built and we started talking about sex.

He reached over and kissed me.

And then suddenly we were standing and I was against a wall, pressed against him while he kissed my neck and I unbuttoned his shirt. My underwear dropped to the floor, he lifted my dress over my head, and then I was naked. He was still in his jeans.

And he turned me around, gently, expertly, and pressed me against the wall. A true handyman.

My ass was bare, exposed and hesitant.

‘We need to go inside’, I whispered, very aware we were still in the garden.

Very aware that I was loving him touching my buttocks.

And very aware that we were going to do this.

We moved to the bedroom. He played with me, tickling me, teasing me, touching me. A little bit in, a little bit out, small gentle touches.

The Handyman was clearly an anal master.

Even so, it’s kinda scary having someone touch you where you’ve never been touched before.

I didn’t use the word ‘Stop’.

But I did use the word ‘Slow’.

And I’ve used the word slow a lot over the last few weeks. We’re still experimenting. One finger has turned to two and I’ve felt the tip of him against me and a little bit in me. It feels good and I think I’m ready for more.

I’ve bought a bottle of Moet to celebrate final entry. We haven’t opened it yet. But I think we will – soon.

We’ll drink it slowly. As we’ll do everything else.

And we might even share it with you, dear Reader. As long as you don’t share this story with my mother.

Tips for Anal Sex

– Only do it if you want to.

– There must be trust.

– Breathe, deeply – yogic breathing is good.

– Focus on the feeling. Really, really focus.

– Go very slowly, over days, weeks, months.

– Don’t be shy to use lube.

And mostly – enjoy the orgasm. And the Moet.

10 thoughts on “Anal Sex – yes / no?

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