My Worst Dating Stories #1: Riding a Cowboy

It was a cold Friday night, June in 2008 and the Rodeo was in town. A yearly event where the world’s best Bull Riders come and put on 2 big shows over the weekend. I had received free tickets to the Friday night show thanks to my Journo friend who was reporting on the event. And what a show it was. 20+ world class Bull Riders in their big cowboy hats, big belt buckles, big personalities and chaps (with pants of course-this was a family event).

Come Saturday night I had planned a single girl’s night out with some friends from out of town. We were having a great time dinner, drinks and dancing. By midnight, we got to the nightclub, to find all of the participating Cowboys hanging out…..oh it is going to be a very good night. As soon as I entered the room, I caught the eye of one Cowboy in particular. Dark, handsome, confident… type. We held eye contact for longer than necessary. I even looked away and turned back….and he was still looking. But he never approached me. I was though, approached by a Cowboy from Camden, who promptly got the nick name “Camden Valley Way. I chatted to Camden Valley Way for a good portion of the night and was enjoying it. When it came to close time Camden Valley Way and I walked to the door together. I knew where this was going…or at least I thought I did. I said to Camden Valley Way “I’m just going to get my jacket” and walked up to my girlfriends to say good bye. But when I returned I found that Camden Valley Way was in his big pickup truck with his mates waving goodbye… WTF! Weird. Anyway it was at that precise time that dark handsome confident Cowboy (finally) approached me. Let’s call him Jim. He wasn’t from Australia, his accent only adding to his appeal. We talked for all of about 3 min before he invited me to go back to a party in his hotel with all of his Cowboy friends. “Sure. Why Not??!?!” (No judging please. I was mid twenties and single, was on a single girls night out and had just been chatted up by Camden Valley Way for 2hrs).

A group of us jumped into the official Rodeo vehicle (a van) and headed back to the Hotel. Along the way there was numerous checks by the (desperate) female promoter, on who was meant to be in the group and who wasn’t.  As it turns out Bull Riding Cowboys are a hot commodity, attract a lot of attention and regularly get hanger on-ers  who want to hang with the cool kids. There was a couple of people who made it into the van and into the hotel elevator who were not invited by anyone and promptly kicked out (do all celebrities go through this?).

Entering that room with Jim and all the Cowboys was surreal. 20+ Rodeo Bull Riders still in their hats and chaps drinking bourbon and strumming a guitar signing country music songs that I have never heard before.

The (desperate) female promoter was all over my Cowboy Jim. She was trying so hard it was laughable. And even more so because I didn’t care. She could try all she wanted, I was ok with just going home. But Jim wasn’t having a bar of it and continued to pay all of his attention to me. She even invited him back to her room so that she could give him a present she had purchased especially for him. To which Jim responded “great- lets go” grabbed my hand and together the 3 of us went back to her room. She gave him 2 very expensive bottles of Bourbon. His favourite spirit (hence the nick name Jim). Jim was super grateful, cracked the bottle open and gave me first swig (much to her dismay). We returned to the party, Jim, I and 2x750mls bottles of expensive Bourbon. I was amazed by how much alcohol Jim could tolerate. I only ever had a couple of small swigs of his bourbon. And he finished the rest of the bottle. And then moved on to the Bourbon he had brought himself (guess the brand name). Jim, I and all the Cowboys sat around discussing the future of the sport, the rule changes they were not happy with and the greatest country songs ever written. Like I said, surreal.

It finally got to a point (about 5am) when I was getting over all the cowboy talk. Jim got up to go to the bathroom and I followed him. He grabbed my hand said ‘ready to go’. ‘Yep’ We went up to his hotel room. He told me to wait outside the room while he went in and kicked his roommate out of bed. He then pushed together the 2x single beds on rollers. We kissed for 5sec. He stopped, took off his precious hat put it on the top shelf of the wardrobe. I turned around took off my shoes and put down my bag. When I turned back around Jim had totally stripped all of his clothes. Totally naked. Without my help. “Let’s Go!” He stated.

No kissing, no rolling around, no grinding, no foreplay. Nothing! Just sex! And it was TERRIBLE. It was jack hammer sex bang bang bang bang bang. And being on a bed with rollers just made it worse. My head was against the bed head bang bang bang bang bang. After about 40min of this atrocity, things seemed to slow down. So I said “Have you finished?” to which he replied

“Yeah, I’ve finished 4 or 5 times already. And I know you’ve finished at least twice”

Twice!! Twice!! Did I miss it? I don’t remember anything. Dumbfounded and confused about how a drunken man can finish 5 times in 40min (am I that good?) and how I missed my own orgasms, TWICE, I got out of bed and got myself dressed, then did the walk of shame back to my place.

A year later I was back at the Rodeo, again with free tickets. This time sitting with 5 friends who all knew of my Cowboy adventures of the previous year. Jim was back to. Apparently he is quite famous in the rodeo world, well regarded and well respected. So the host of the rodeo got up in front of the 1000’s of spectators to personally thank Jim for returning.

“I would just like to give our warmest thanks to Cowboy Jim for coming out to our event again this year. It is not easy for him to be here as he has had to leave his wife and twin daughters at home to be with his tonight”

Wow! I was shocked. My friends were in hysterics. And I am still copping it from them today.

A big thumbs up to you Cowboy Jim. Not only providing me with one of the most surreal nights of my life, but also being the winner of the ‘worst sex I’ve ever had’ award.


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