View Full Version : 3 Hookers and a Funeral (GREATEST WEEK OF MY LIFE!!!)

06-09-2012, 05:43 AM
I began writing this while getting some free time, a few weeks ago, when I had a few hours to kill. Unfortunately, I couldn’t finish it then, and ever since my new college year began, I have barely been able to find enough time to get a few hours of sleep! Anyways, it is 100% true, and describes what might be perhaps the greatest week of my life! If the title doesn’t give it away, this isn’t really like the other stories I have posted up on here. It isn’t as long, as detailed, or as well written as those are. These were much sleazier adventures than those of my past, and are much fresher in my mind than those were when I wrote them. Anyway, here it goes.

As some of you may know, I went away from DOSF for about a month, and came back just about a month ago. Over those 3 weeks that I was gone, quite a bit of things went on in my life. I hung out with old friends, went to a few parties, had some bad times, and even got kind of depressed for a few days. On the final day of June, my father came up to me and told me about one of his friend’s relatives who had just passed away in Chicago. He wanted to go to the funeral, which was in less than a week, but was too busy, so he wanted me to take his place. Now, while this all seemed highly peculiar to me at first, I certainly didn’t mind going out of town for a bit, even if the reason was as morbid as this. I had 4 days to pack, and before he dropped me off to the airport, he handed me a carry-on, seemingly full of stuff. My dad told me to open it once I got to the hotel, which was just a few minutes away from O’Hare International, and not a minute sooner. The whole journey from takeoff, to touching down, and to the hotel was rather odd; I could sense that air of euphoria rising through my veins, preparing for the adrenaline rush the following week would ultimately provide.

Finally arriving in my room around 5 in the evening, I fell onto the bed, ready for an extravagant slumber. Suddenly, I remembered the carry-on, and decided to open it. Shock doesn’t even begin to describe what my mind went through when I began to examine the contents of the bag. It consisted of a small, closed metal box and a letter. The letter said,

Dear Shan,

I know you have been going through quite a bit lately, and your mother and I
felt it was necessary to let you have some free time. This opportunity came up,
and we decided to use it for your benefit. Yes there is a funeral, and you will be
picked up tomorrow at 9:00 sharp. But, your flight home isn’t scheduled until 6
days from now, so and we want you to use that time as you see fit. You can relax,
sleep, go to restaurants, sightsee, even go to a Cubs game(I know you love sports).
Whatever you wish to do, you can. Just make sure that you don’t go over budget!


Wow. Never did I expect this. When I opened the metal box, it contained $1000! Boy oh boy was I going to have some fun with this! During those remaining 5 days, I did quite a few things. I went to a few ballgames, explored the city, went to a few restaurants, etc. Anyways, I know none of you give a shit about any of that. You all just want me to get to the good stuff! Therefore, I’ll do just that.

The following night, after the funeral, I decided to take the rental car out for a ride throughout the city. Boy, was that funeral some sad stuff. The fact that I knew none of those people, yet they all knew who I was, happened to be just as creepy as it was awkward. Thank goodness that was all past me now, and I could finally enjoy this solo vacation. Eventually, I got to a dark corner of the city. There was darkness everywhere, with shimmering lights sprinkling throughout the dim streets. A sense of taboo drowned my mind. Certain areas were packed, whereas others were not. I had no idea where I was, and yet I felt right at home when I was there. Holy shit, I was in Chicago’s seediest area!

For those that do not know, Chicago’s “Red Light District” was practically wiped out by some prude mayor a few years ago. Since then, some prostitutes have resorted to the Internet and “house calls”, while others have either moved, or begun working in discreet streets in various corners and crevices throughout the city. I just happened to find their new “hub”! My pulse racing, I noticed a hot brunette wearing short-shorts, a pink top and some fuck me boots. Over the course of the next hour, I got to sniff her malodorous pink boots & cheesy feet, and even got a bj, all in my car, for only $50! As great a night as it was, I figured it would never happen again.

Just for the heck of it, the next night, I decided to head to the same section of the city again. This time around 2 in the morning, there weren’t nearly as many people. In fact, it looked nothing like the night before! I figured I was in the wrong place, when this voluptuous Latina, wearing a tight leather jacket and hella sexy skirt walking along the sidewalk caught my lecherous eyes. I drove up to her, and while I’m not too proud of what all came out of my mouth, I did get a chance to satisfy my desires. I took her to a nearby motel, where we got things going. Lets just say this one was incredibly skilled. Hell, I’d never been with anyone as spectacular as her before! He very presence was enough to make any man go insane. The fact that I was able to be with her for 2 hours is simply astounding! As for the feet, well, when they’re baking in black leather ankle boots for nearly 10 hours (she said that’s how long it was, and it really seemed like it.), you know they’ll be something special. Those puppies were so vinegary, her toes so rank, 3 of my personal record 5 orgasms that night were solely due to them! How I managed to get back to my hotel room conscious and without much suspicion from others is beyond me. The more I think about it, the less likely it seems I’ll ever come across another Larissa ever again-at least not for under $200.

The following 2 days were primarily about relaxation. I went to a ballgame, got some much needed rest, and took everything easy. All of a sudden, I remembered that an old friend who had moved to Chi-town years ago and must’ve known the city top to bottom. I managed to get a hold of his number, and the first thing he did was give me the number of his favorite escort, Rachel (he’s a pretty wild guy). Since I hadn’t seen him over the past few years, he asked me to have dinner with him. I told him I didn’t have much money, but he offered to pay for it. Afterwards, he wished me luck in my future and talked about how it was great to see me again. I didn’t make much of his words at first, but once I got back to the hotel, that all changed.

The moment I entered through the doors, a woman rushed up to me and gave me a sensual, wild kiss. Stunned by what had just occurred, I stepped back and took a look at this woman who had assaulted my senses. The look turned more into a glaring stare, as this “woman” looked more like dazzling, arousing, erotic goddess. Her sexy black dress, hair well made, shimmering golden earrings and 5-inch leather black pumps had all of me in full attention. While I was ogling at this tremendous beauty, she was talking to me in a way that would make it seem as if we were in a relationship, so as to keep others from suspecting anything. Suddenly, she hugged me, her warm breath weaving its way into my ear, as she began whispering into my ear. “Rachel knows what you want big boy. I know what you were looking at. Dave told me everything. You were looking at these, weren’t you?” she inquired as she began some shoe play. “Don’t worry, I’ll give you more than you could’ve ever imagined.”

I was sure I could handle her, but her sweet fragrance hypnotized me to a point where I was fully under her control. She asked me to take her to my room so the fun could begin. Once we got in, riveting blonde pushed me onto the bed, undressed me, and got on top in a 69 position. While I took her to her peak multiple times, she kept teasing me, but managed to keep me from bursting loose each time. She allowed me entrance into every orifice, but wouldn’t let me cum. Finally, she sat on top of me facing my chest, and said, “Here you go”. Stunningly, she had not removed her shoes yet! She had apparently had them on for 5 hours at that point, and she knew they would be my undoing. Sitting on my abs, she moved her legs right next to my face. While gradually slipping them off, she began to grind over my cock. She teased for a split second, then, in the blink of an eye, gorged herself onto my dick while slipping a pump completely off and shoving it over my nose. The pungent scent shrouded my senses, while I was edging closer to release. Her words of encouragement, “Come on baby. Give it to me. FILL ME WITH YOUR CUM!!”, were swiftly pushing me towards the edge. Sensing my impending eruption, she removed the other pump, let me take a few deep sniffs of the cheesy essence, then covered my nose with her fetid, overpowering toes. Her loud, high-pitched moans got me closer and closer, and with one monstrous whiff, I exploded deep in her velvety pussy, undergoing undoubtedly the greatest climax I had ever had. She gave me a kiss, and when I asked her how much I owed her, she said, “Don’t worry. It’s Dave’s gift to you.” Man, I should really talk to him more often! Anyways, I thought I was spent, but when she invited me into the shower, it turned out I had much more left!!

Alas, I bid Rachel farewell a bout 45 minutes later and thought about what a great week it had been, before I fell asleep. I had gone from somewhat depressed to incredibly blissful over a matter of just a few days! I made it to my flight on time, and thought about the events countlessly in my mind. What an incredible adventure it had been, and I had $350 left! Although college has been a pain it the ass since I transferred to a real university, it’s memories of this week that have let me keep my head held high.

10-09-2012, 08:39 AM
More stories coming this week.

14-09-2012, 09:25 AM
i will download your novel and enjoy it on my bed, haha ~

16-09-2012, 07:50 AM
lol glad you liked it man.

26-01-2013, 12:34 AM
Glad this story is still here.

24-02-2013, 05:23 PM
That story was dope!

26-02-2013, 02:21 AM
Thanks clay, I'm glad you enjoyed it.

26-02-2013, 02:22 AM
Can't believe this has gotten 1,500 views!! THAT'S CRAZY!!!