Anal Sex Adventures Gone Wrong

In my online dating years and when I was pretty determined to sleep with someone from every country I decided I had to sleep with a South African. There’s actually a very healthy rivalry between South Africa and Australia so it had never been too high on my list of priorities, but it was a box that needed to be checked.

I scoured the internet for ages finding the right one. Now I was in mid-twenties. Younger boys held no appeal for me, my preference was for older men, but I was also happy to fuck someone in my own age bracket.

I wish I could remember his name because he’s sent me a thousand friend requests on Facebook (all of which I declined – what a bitch I am sometimes!) so I should be familiar with it. But I’m not. He’s just another face without a name in my sexual history.

Aside from being South African (I’ve been told I need to clarify here he was white Caucasian) he wasn’t a bad looking boy. He actually possessed more of an American look and was reminiscent of Tom Cruise, which is no bad thing if that’s your type. He was short, maybe 5’5 with shoes on, had blonde hair, perfect shiny white teeth and the body of someone who spent a lot of time at the gym but didn’t have the physique for it to be overly impressive or noticeable.

We’d chatted online briefly and I organised the hook up just as quickly. As with any cyber sex sessions, discussions of likes and dislikes had come into conversation and I do believe mentioning I was quite up for anal sex. In all honesty I wasn’t that up for it, but some men see it as quite slutty and sexy so I felt it would increase my chances of getting laid.

The only thing about dating younger guys, or at that time men in their mid twenties is their lack of confidence. Despite me giving him my address he asked if I might meet him a the tube station and walk him back to mine. It kind of seemed a role reversal in terms of traditional male/female roles but because I was pretty independent and desperate for cock I agreed.

Meeting him at the station I could see not only was I going to have sex with a South African but also a man that would’ve been classified as a dwarf if he’d been born an inch or two shorter -not great for a 5’7 Amazonian-esque Australian like me.

I had an inkling I would want it over and done with asap. Bit of a workout for my vagina, send him home and then a bit of fast food and crap late night TV.

The bedsit I was living in at the time was in fact in the loft of a top floor flat and I had to climb up a ladder to get in there. There was a single bed, which I used as a couch and a double futon which I slept in.

The sex was almost perfunctory. By the time we got up the ladder, there wasn’t really all that much to discuss. He was a trainee accountant at a law firm, which is probably why he could afford to buy the best brand of lube in the market, which he presented to me like a wedding ring, but his profession wasn’t riveting enough to warrant feigned interest and questioning about his job.

It was kind of a kiss and clothes off affair.

In hindsight I found the height difference a little off putting. I could lay on the single bed, my bottom perched on the edge, legs spread, wet and waiting giving him easy access but as he began fucking me I realised he didn’t even have to bend his knees to get into my cunt. Nor did he need to prop my bottom up with pillows so that he wasn’t squatting while he was thrusting. If anything I suspect he would’ve been happy if he’d had a few pillows or a small cardboard box to stand on while pumping away.

His inexperience and lack of technique was all too obvious. I liked his enthusiasm and the velocity. His thick cock going in and out of me was pleasing. But the man handling of my breasts, squeezing them, pinching them was all good until he suckled them. He didn’t suck quickly, or suck and nibble. He suckled them as one would imagine a baby would. Making slurping noises. Ths short South African had a fat stubby cock inside me while he suckled my breasts. Taking turns on each one. Resting on my chest and just sucking and pumping. Thank fuck he didn’t call me mum.

I was wondering how long I’d have to endure the child like sexual behaviour when he boldly said, ‘Your arse. Let me fuck your arse.’

‘Yeah sure.’ I agreed quickly enough thinking the sooner the experience was over the better.

‘Do it like in the movies please.’

Wordlessly I moved from the single bed onto my double futon on the floor on my hand and knees. I could hear him squirting the lube and telling me how much he wanted this. I was going to ask if he wanted it more than me putting him in a nappy and giving him a rusk but thought it may further delay this mortifying experience.

Things went from bad to worse. His pork sword may have been ready to invade but my anus was having none of it. It was as if my arsehole had been super-glued shut. This should have demonstrated how tense and unrelaxed I was in this encounter but the South African wasn’t taking no for an answer. He just put more and more lube on his cock and more and more lube around my bottom.

He pounded and grinded trying to force the slightest opening so he could then force his cock in. It was lucky he’d been working out cause he needed the strength and stamina for this nearly impossible feat.

I mentally applauded him because he did manage it. But the sheer power required had meant while I’d started on all fours with each thrust my hands slipped forward and I began to move downwards. I could see my hands pushing the duvet towards the wall and my face getting closer and closer to the mattress. Soon enough I was lying on my stomach. Pancaked on the bed. I’d have preferred to be a little more picturesque and described myself as more of a ‘crepe’ demolished on the bed, but my rather rolling soft curves meant I was more a fluffy, filling pancake. It wasn’t until I was plastered to the bed that he got in. I was face down on my bed as his cock stabbed into me. In an effort of my own, and I wasn’t  a regular gym goer, I resisted the intensity of his thrusting just enough to raise myself and my arse up so he could penetrate a little deeper. Where I mustered the energy I know not where – at that time I did wonder if there wasn’t something in all this religious malarkey – but in returning to half doggy style position it gave him enough room to be thrilled enough by the anal sex to cum.

I disposed of his presence as quickly as I did the condom. To be honest I probably would’ve enjoyed visiting South Africa more via Google Earth rather than have someone bum me quite so viciously and vigorously. I don’t think I dismissed him in a nasty or harsh way because he very kindly offered me the exclusive expensive bottle of lube so we could have anal sex again next time he came round. He never came round again…but the lube was used up for more anal sex.

Posted on April 18, 2013, in A Little Bit Of Everything, Anal Sex, Disappointing Sex, Foreign & Interracial Sex, Teenage / Young Sex and tagged , , , , , , . Bookmark the permalink. 1 Comment.

  1. I absolutely love this post! Not many people will write about sex fails, and not only did you do it but managed to make it hilarious as well! Fantastic job!

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