Sunday 24th March 2019,
Jack Gary

That Time I Broke My Back Having Anal Sex In South Beach

South Beach is like no place on planet earth. I’m pretty sure that an eternity in hell will be like a weekend in South Beach, Florida. One memorable weekend in particular stands out, because it was the first time I really tried anal sex – not the “just the tip, this is too weird” kind of anal sex, but full on, certified butt sex. I was in Miami for a sporting event that had something to do with water, but I can’t really remember what it was. The client knew that I like the hotels in South Beach, so they put me up in a swanky one with a giant king sized bed, which is perfect for me, because I can fit a lot of women on it.

Speaking of women, the chicks in South Beach are the human incarnations of the city itself: lots of bright, pretty neon signs on the outside, but not much going on inside. I’m speaking about the clubs and nightclubs, of course – the hotels in South Beach are a little nicer inside. A typical woman in South Beach will have the fake C cup, or even D cup, sized breasts – and their tits are usually trying to blast out of some kind of sequined tank top that’s way too small for them. I am of course fine with this – I love the whole side boob, top boob, and bottom boob thing. Most of them are also wearing a cheap leather mini-skirt of some sort or a knee-length skirt with cargo pockets (the cargo pockets always make me laugh). And for some reason, all of these articles of clothing can be removed with as little effort as possible, and usually with one hand. Every time I hook up with a chick in Miami, it’s like I’m a magician – I’ve never been able to remove clothes as fast as I can as when I’m in South Beach.

On the second or third night that I was in town I was getting a little restless. I needed to get my dick wet, as they say.  I kept thinking that if I need to have sex I’m going to have to throw myself in the pit of the South Beach beast: Ocean Drive. This is where all the main hotties are at night. So first I hit up a few of the nightspots and clubs just to get a feel of the playing field. It usually takes about 3 or 4 places to get the vibe of a particular night: hectic, laid back, etc. That way I know what I’m working with when I try to land a chick. That night in particular was crossing into hectic. Also, I’m not into the whole getting drunk thing when I’m trying to get laid, so I probably only had one or two glasses of wine. The drinking and sex thing doesn’t work out for me, because I like to keep a clear head when I’m looking for quality pussy.

It was getting a little late, but I was at perhaps the 5th nightspot when I met a gorgeous blonde girl, a local. We hit it off great. I knew then if we got too friendly it would never work out. This girl was actually smart and I almost felt bad taking her as just a quick fuck, but I put my morality aside for a second and went with the flow. We went to a few more spots and soon enough we were too bored to stand it anymore. She was trying to stay sober too, because she had to go to work early the next morning. So we decided to go back to my hotel room. On the way back she mouthed to me: “I want to fuck.” Before I could respond she dragged me behind some palm trees, pulled down my pants and started blowing me. The night had just started getting way more interesting.

Before I could blow my load, I quickly realized that there were about 3 dudes staring at us. I rapidly pulled up my pants and hurried away with my new lady friend, back to the hotel. When we got back to the room we started having sex immediately. I was already fingering her clit on the way back to the hotel so she was insanely wet already. However, I remembered there being something not quite right. We changed a few of our positions, from beginner cowgirl to advanced tantra sex, but something was definitely awkward, like she was distant or something. I asked her if everything was okay and she told me that she couldn’t climax from just regular sex and that she needed to have anal sex to get off.

I was never into the whole anal thing and always had a strict vaginal sex only policy. I had this preconceived notion that I never wanted to put my dick in anything that shit comes out of. It’s just not real sex, to me. I know that birds have something called a cloaca, which is their only hole for reproducing, pissing and shitting.  I would think about that every time I thought about anal sex. I have also talked to lots of homosexual guys that get off on it, because they have a prostate. I didn’t understand how this girl could get off on it, but I felt bad for her…so I oblige. I position my cock and balls like I’m aiming a gun and I put it in her butt.

At first it was going great. She was bent over with her ass in the air and I was going at it like a pro. If you saw our shadows on the window blinds from the outside it would have looked exactly like I was churning butter. It was a little bit like riding a ship in a storm as I was holding on to her ass and then her tits, as she fingered her clit at the same time. But what I didn’t know was that each time I thrust into her I was inching closer and closer to falling off the bed. All of a sudden, I felt a shift of the weight below me and I came crashing off the bed and onto the marble floors of the hotel. At first I laughed it off, but then I quickly realized that something was terribly wrong. There was a shooting pain in my back where I landed.

The blonde had now turned around to see what was wrong. When she decided that nothing was really wrong, she had the audacity to tell me to keep fucking her in the ass. An honorable man knows when he is down for the count. I told her I needed to go to the hospital. So she got dressed relatively easily – she wasn’t wearing much to begin with, and then helped me get my clothes on. We go down stairs, hop in a cab and head to the nearest hospital. The doctors take an x-ray and then tell me that I broke my coccyx bone – which is the lowest bone in your spine – right above your ass. It hurt like hell, but they told me all I could do is take painkillers and rest. The best part about this story is that the blonde gave me an amazing blow job right on the gurney. As Shakespeare said: “All’s well that ends well.”

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