Sunday 24th March 2019,
Jack Gary

One of the Greatest Nights of My Life

One of the greatest things about life is that it’s not scripted. Life is full of some of the most pleasant surprises. For instance, when a girl is going down on you and she is a master at the art of pleasuring the male g-spot and puts a finger in your butthole without asking. Or perhaps when you are driving your best friend’s girlfriend home and she starts to give you road head and right when you pull up to her apartment swallows and says goodnight like she’s gargling saltwater. Or when you go to a party and walk into a restroom to find a girl fixing her makeup and immediately start making out with her and then start having sex with her in the shower, and then go back to the party like it never happened. Those kinds of things; my life is full of those moments.

Jack GaryOne night in particular that stands out started off particularly boring, but quickly escalated to hells bells exciting with each passing hour.  I was invited to a friend of a friend’s financial advisor’s bachelor’s party that was held at some hotel on the swankier side of town. They went all out and bought out the mezzanine to party and they planned on taking over, turning the whole place into their own private Kublai Khan pleasure dome. Usually the opposite happens and it turns into one giant sausage fest and I move on, looking for excitement (and pussy) elsewhere. But on this night there was something in the air that made me hang on, like a gambler waiting for the next royal flush. It was probably the ratio of women to men – I’d say three to one with beautiful young women taking the majority. Apparently, on another floor of the hotel there was some sort of international modeling contest. A big modeling agency from Paris was in town and they were holding auditions to see who would sell their soul to the fashion industry and move overseas to grace the magazines and runways. Anyways, picture the scene: boring financial accountant types with way above average IQs and tons of gorgeous wannabe models who would do and say anything to get your approval, because most of their dads probably went out for cigarettes one night and never came back.

With a look of bewilderment and excitement to find some kind of congregation of the opposite sex, the models slowly came pouring into the party.  You know those nature programs that show the lions on the hunt, hiding behind a thicket of grass eyeing a bunch of gazelles frolicking in a pack? I was one of those lions and my eyes were getting bigger and bigger and my mouth was watering something bad for one of those gazelles. I was ready to pounce, that’s for sure. And there were so many of them I didn’t want to just go for the weakest one just because it was easier. I knew I had my pick here. I was playing a mental game of eeny meeny miny moe. There is nothing I love more than a gorgeous, thin model with daddy issues and this place was full of them. Unfortunately, my first attempt ended dreadfully with a swing and a miss I regret to this day.

I narrowed in on a girl who looked particularly bewildered standing near the entrance as she was looking for her friend. She was gorgeous, had short hair and one of those shirts that shows her stomach and those two lines that shoot right down to her crotch. We made eye contact and I took that as a cue to talk to her. Her and I start to chat and flirt, but something starts to annoy me about her. She is too dumb for me to handle. Much like there are height limits at amusement parks, there is an intelligence limit for Jack Gary. I need to find a way to sabotage this conversation without just walking away. If I wasted 10 minutes talking to this broad I was going to take it back in some way. In a sort of joking manner I tell her that I’m Jack Gary and that if she wants I could take her back to her room, tell her she’s pretty, fuck her, come on her tits and leave without saying goodbye.  Apparently she didn’t hear me the first time, because the music was so loud, so I said it again. This time louder and of course that’s when the song ended and everyone within earshot looked at me like I was the biggest asshole on earth. She walked away in disgust. Dumb model if you are reading this today, I’m sorry.

I was on the prowl again. This time my grassy thicket was a big empty booth at the side of the room. Everyone was dancing to terrible music and the DJ looked like Jamiroquai circa 1996 with a giant, ridiculous fur hat. And all the wannabe models were at least a foot or two taller than most of the guys. The general ambiance was a cross between a winter formal and some shitty club on the Jersey Shore. It was almost completely dark except for the flashing green and red lights, and a bunch of white lasers pointing this way and that. It was a dreadful scene indeed and I almost felt like getting out of there. That’s when one of the models sat right next to me. She was a little shorter than the rest and she was part Asian or something. The first thing I told her was that she was short. Mind you, the minimum height for most of the models in the room was 6’1” with heels and all. The girl that sat next to me must have been around 5’10”. Her response to my comment was that she was a print model. I asked her what the difference was and she told me that she didn’t do runway. As we were talking I could tell that her intelligence level was higher than the rest – maybe because she was Asian – and she was very down to earth. I’m pretty sure this was going to be my score for the night and the reason I went out in the first place. After I was ready to seal the deal and take her home, she asks me if I want to dance. Let’s get one thing straight: Jack Gary doesn’t dance. But I oblige, because she is hot and I want to get my fuck on with her.

As we hit the dance floor she gets really excited. You know that excited screaming that girls do and you don’t know if they are in trouble or just excited? This time it was the former. Apparently her favorite song was on and she starts grinding away on me. In most of these situations I do a little bit of movement with my arms and my waist to give the illusion that I’m dancing, but most of the time I let the girl lead the way.  As the song reaches the bridge she does a little grind all the way up my body and starts giving me little seductive, half kisses on the lips. I’m ready to take her hand and get out of there. The song ends, but she does another excited squeal and says that this is her second favorite song and we have to stay just until the song ends. At this point I’m getting a little annoyed and tired of doing my hand and waist dance. Half way through her second favorite song she does one more excited squeal. I think: oh god, what now? Is she really in trouble this time? That’s when the most miraculous thing happened. I don’t know if it was the laser light show, the bad music, or all the axe body spray, but I started seeing double. I had to close my eyes to readjust and when I opened them – no dice – I was still seeing double. But I wasn’t seeing double at all. This hot, half Asian model had an identical twin sister who was a model too. I’ve been in weirder situations and the gods have blessed me before, but never with twins and never with twin models.

After dancing to five more of their favorite songs, we all go back to the booth to get acquainted. Her sister is a little dumber, but just as hot. I think that there is no shot in hell that I’ll get to take both sisters. I was wrong. They happened to be staying in the hotel and were sharing a suite. All three of us go back to the room. One of the sisters puts on the bath. The other sister and I start making out on the bed. She starts taking off all her clothes. She had little, perky, perfect tits and I start diving in. She is moaning and I’m thinking that this has to be one of the greatest nights of my life. That’s when the other sister comes out of the bath completely naked and partially covered in bubbles. She asks what was taking us so long and why my clothes were still on. I take my clothes off and the sister I started making out with takes my hand and leads me to the bath. After some good making out, one of them starts jerking me off and the other one mounts me. It went like this until the bathwater was cold so we moved to the bed. I make each one of them cum over and over again and amazingly they have identical sounding orgasms. As I lay there in the hotel bed, in what was possibly one of my greatest conquests, I couldn’t help but think what all those other losers at that party were doing in that exact moment. Probably not this. Life really is stranger than fiction.

Facebooktwittergoogle_plusredditpinterestlinkedinmailby feather

Like this Article? Share it!

About The Author