“He isn’t “in” the Mafia, but all of his friends are.”

This is another one of my stories from Spring Break 2007 to Cancun Mexico, which I will never forget. This story like many others from my Cancun stories begins in the swim up bar at about three in the afternoon.

After starting the drinking at about 10AM and drinking beer after beer and these shots called, “Purple Mother Fuckers” I was pretty drunk by noon. I would just grab a drink and then go wander around and talk to girls, if I seemed like an ass, I could always blame it on the drink in my hand.

So on the way to the bathroom double fisting my margaritas I walked passed a small group of girls maybe six of them tanning. “Would any of you ladies want to join me and my friends in the swim up bar?” Like it was an exclusive club that no one could get into. Most of them just looked at me like I was the biggest idiot they’d ever seen but one really cute brunette girl stuck out her hand and said, “I’ll go.”

I grabbed her hand and led her to the bar. SCORE, I’d lured some hot girl into the swim up bar with me. After getting to know her a little better in a little private section of the pool I learned she was 21yrs old and a student at Michigan State, I was seventeen and still not out of high school.

She ended up living about five minutes from me and graduated from our rival high school. I can’t really remember what I said to her in the next few minutes but I do remember that in about twenty minutes were in making out hardcore in the pool with all of the resort to see. Oh and her name was Jess…like that matters.

The whole time I was making out with her my friends watched and I’d open my eyes and do the “thumbs up or down” behind her head to make sure I didn’t have my drunk goggles on. Each one of my friends gave her the thumbs WAY UP. My friends were some of the most impressed because they were convinced I had no game when it came to meeting women.

Frankly I was just as surprised as they were, but this is just when shit started getting weird.
During a little make out session I felt a tap on my shoulder and I looked up and there was an older woman crouching down next to the pool. “I owe you this.” She said holding out a twenty-dollar bill, “My friends and I over there had a bet on who was going to hook up with a girl first; you or your friend over there. I bet on you and won $200, I thought you deserved this.”

I took the cash and we both had a laugh about it, because honestly my friend is a lot better looking than I was and he usually did better with girls. We kept making out for a while and during one little session I saw this hairy old man starring across the bar at me making out with this girl.

“That’s just my dad,” she said and tried to shove her tongue down my throat.

I had learned in an earlier conversation from this girl that her family was fully blooded Sicilian. I’m half Italian myself and I knew my balls’ life expectancy had just been seriously decreased if a Sicilian father saw me making out with his daughter.

“Here I’ll introduce you,” she said and dragged me over to him and he took off his sunglasses and stared me down. He was with a group of about five other Italian guys all wearing Ray ban sunglasses and thick gold chains that held crucifixes.

He kept questioning me about my family and where in Italy they were from, what politicians I support, the best thing about it though was that he liked me. He knew the small Italian village my family was from, he was a Democrat like me, and he thought that I had good taste in cars. We ended up talking for about twenty minutes, but when I asked him what he did for a living he hesitated and said something about waste management and insurance, I was skeptical.

So he shook my hand, and I said good-bye to him to go find his daughter who wandered away with her sister. About five steps away from Mr. B and one of his cronies who was sitting with him walked up to me and grabbed my arm. “Buddy, you don’t know what you’ve gotten yourself into. That man over there is “Connected” you’re fucking with the wrong girl. My advice to you is to just move on and find some other broad.”
So he just patted my back and turned me in the right direction and I walked away. I felt like I’d just walked onto the set of The Sopranos and I was about to get whacked by some Guido looking guy in an Adidas track suit.

When I found Jenss she invited me into her room with the promise of getting to see her tits. I mean, even if I was going to get whacked at least I’d get to see some boobs out of it. We got into her room and sat down on her bed and she said she felt dirty from the pool water and wanted to take a shower. I’ve always been a big advocate of hygiene so I couldn’t help but agree and to save water by showering together.

So there we were naked in the shower making out and fondling each other, but like a jackass I stopped her. “Is your dad in the Mafia?” I asked looking her straight in the eyes trying to avoid staring at her perfect breasts with the hint of a tan line that really turns me on. “He isn’t “in” the Mafia, but all of his friends are.”

So basically this hot naked Italian girl that I had only met two hour previously just told me that her father was capable of having me on the bottom of the Detroit river right next to Jimmy Hoffa. But fuck, I didn’t care I was on spring break in Cancun and I had a naked girl in front of me in a shower and I wasn’t going to let anything stop me. Just as she got on her knees and serviced me like never before we heard someone walk in. “Is that your dad!?!?!” I asked taking a step back. “It’s probably my sister.” She said and continued.

Believe it or not but I had a hard time keeping it up no pun intended with the thought of a giant Sicilian father only feet away from me while his daughter going down on me. I finally made her stop and go check, if it was him she’d lure him out of the room and I’d be able to make a quick get away. When she left the bathroom all I could hear was, “Hey daddy.”

There was more talking and then she popped back in the bathroom and whispered. “We’re going to dinner, meet me at Senor Frogs at ten. Then we can finish where we left off.” And she gave my package a squeeze. Hours later I was in my room with my friends about to go out to the clubs debating whether I should go meet this chick. I mean, I knew I had a chance at getting some skank at the bar to make out with me. But this girl had promised me no strings attached sex; I just had to live with the constant fear of her father bashing my skull in with a nine iron.

We all came to the same conclusion that all head injuries aside it would be worth it to hook up with a girl four years my senior with an amazing body. But I thought of taking it one step further, while we were all sitting around in the room I noticed my friend’s camcorder on the dresser. “I’m filming it!” I shouted and everyone seemed to think it was a good idea it seemed like something straight out of American Pie.

But the plan was to get her on my bed and distract her so I could push the record button while the camera was safely hidden beneath a t-shirt. Fool proof.

Sure enough at ten I found myself standing by the bar at senior frogs searching the droves of girls wearing tube tops and denim skirts trying to find mine. Sure enough when 10:05 rolled around I saw here walk in with her sister and their friends. The talk was short because we both knew what we wanted. So we danced for maybe two songs, had two beers and started walking back to the resort hand in hand. Once we got into the hotel she was obsessed with taking a shower together again, so I obliged.

My plan was to just get a little BJ in the shower and seal the deal on the bed all with the little red light watching us go at it. The shower was perfect now that I didn’t have to worry about Al Capone busting in, she got right to business on her knees as I sat on the edge of the tub she even put her hair back in a ponytail so I could enjoy the show too. About ten minutes into it she was getting dirty and pulled me up and said, “I want to fuck right now, right here.” So I got on the ground and she mounted me reverse cowgirl and just kept screaming as my wet body slid across the tile floor.

That was when I remembered I was supposed to film this thing, but this girl is really going at it. I slowed her down and suggest getting on the bed and she seemed excited, “You dry up and I’ll be waiting for you out there.” I said, this plan gave me enough time to get the camera set up. I ran to the dresser and began to turn on the camera and just as the screen turned on out came Jess walking towards me wearing nothing but a grin on her face. She hadn’t seen me fiddling with the camera and she just laid down on the bed with her legs spread so I hopped on and started pounding her so hard every room on our floor could hear us moaning.


I didn’t realize until I looked at the camera to wink; that the little red light wasn’t on! I had forgot to push the record button. I pulled out and told her I wanted to do it doggy style. Once I had her bent over the bed I would thrust and I leaned back to the dresser behind me and pushed the button and I suddenly I felt like I was Dirk Diggler in Boogie Nights. I was trying positions I’d only seen in Asian porn knowing that the next time I watched this would be on my buddy’s big screen TV back in Michigan.


But I made the mistake that probably any 17 year old would. Mid-hump with her on top of me digging her nails into my chest I ask her, “Are you on the pill?”


“No, just don’t cum in me!” she said and kept moaning.


Just as she said that I panicked and felt climax about to happen I threw this girl off my dick and onto the other side of the bed as I busted all over.

She went off to the bathroom to get her underwear; that was when I walked up and looked in the camera and just said, “You’re welcome guys” and shut it off. I promised her I’d go meet her in her room and we’d cuddle in our PJs or some dumb shit. Instead I went to the bar downstairs and never saw her again, but I’m still waiting to get a claw hammer in the back of my head from her dad.