I Should Have Listened to my Mother

When I woke up it was 2 in the afternoon. I was alone. I had the worst hang over of my life, my head was pounding. I lay there and remembered much of what had happened and began to cry. As I lay there crying I realized I had an absolutely horrid taste in my mouth and my breath smell just as bad. I sat up wondering "WTF?!" and I saw the state of the bed I was laying on. My face and crotch were coated in dried, crusty seaman. The sheets were a mess as well. Then I saw it. Several brown stains on the sheet. I realized what the horrible taste in my mouth was. I ran to the bathroom to vomit and didn't quite make it. Some hit the floor before I made it to the toilet. I couldn't stop puking. I heaved until nothing at all was coming out. And heaved some more. When it finally all stopped I was so thankful for the mouthwash I found on the counter. I used every bit of it and even drank some. I climbed into the shower and stayed there for well over an hour, the water as hot as I could stand. I cried and cried over what I had done. I made myself sick with anguish over what might be. AID's. Am I pregnant? Will I get hepatitis? Did they take pictures that are going to pop up on the internet? "Oh my God, what have I done?!"

Two days later I got my period. I did get a vaginal infection from one or all of them going from my anus to my vagina. Antibiotics took care of that. I had blood test done and everything came up negative. As for the pictures, nothing has ever came to my attention. I eventually hope to forgave myself for what I did that night. That being said, I still remember that night with some fondness. At one point I had all three of the men inside me at once. It was a truly amazing sensation.

Without a doubt, the dumbest thing I've ever done.

Prostitution

My mother; Lillian. More about her later. I have to say she is without a doubt my best friend in the whole world. Not simply because she's my mother, because she is a wonderful person. Her wisdom is legendary. She has always been there for me, and I have no doubt she will continue to do so until the day she dies. And I for her as well. I would walk through fire for my mother. We live in the same city, 10 minutes from each other. We see each other all the time. Such has not always been the case. There was a time in my 2^nd year of college. She and I had had a major blow up and ensuing argument. I told her to stay out of my life and that I didn't need her or her money any more. I get this bold trait from her by the way. My aggressive and confident nature comes directly from being her daughter. She ended the screaming match by saying "Have it your way." and stormed out of my apartment, slamming the door. . . I'd show her!

At this time in my life I was like 21 or 22. I had something like $7 – 800 dollars cash on me. I had two credit cards. That's it. Mom froze the credit cards the next day. (I did not call her) I was sharing a nice apartment with another girl and we got along just fine. We soon became really good friends. She came from a family similar to mine. Parents had money and footed the bill for everything and sent their kids cash when they needed. The kids were expected to go to college and earn a degree, which was their end of the deal. There weren't many of those like us, but that was certainly our situation. Lori carried me financially the best she could. Her parents found out from my mother about our argument. Lori's parents were real careful about the financial support they gave her fearing I would not learn the lesson my mother was trying to teach me.

Three months into our tiff and it was Thanksgiving. I spent the first Thanksgiving away from my mother in my whole life. I was still really pissed off at her and what she had said. I'd gone to Lori's parent's house for the long weekend. Big family, lots of wonderful food and drink, it was actually a really good time. Later in the evening, after a second go around of food, I was out on the back porch very sneakily smoking a joint. I heard much merry making coming from the house as yet another family member showed up. About 20 minutes later I was now lounging in an Adirondack chair, very stoned and happy.

Lori comes out with an older man. "Jessie, I'd like you to meet my very favoritest uncle in the whole world, Jordan. Uncle J, this is my friend from school, Jessie" Uncle J pulled up a chair as well as Lori. We began our visit with uncle J with casual small talk. Soon uncle J says "Hey, you ladies want to hit a pipe?" and held out a small pot pipe. I smiled and declined but Lori took it and the lighter and took a few puffs. Then uncle J did the same. Soon all three of us were laughing our butts off about something. Uncle J was indeed a charming and fun man. I could see why he was Lori's favorite. We stayed outside for hours. Lori finally bid us good night and kissed her uncle and went to bed. I was about to do the same when uncle J said "Jessie, I'd like to talk to you about something."

"Yes Uncle Jordan, what?"

He looked about the property and inside the house to make sure nobody was around or paying any attention to us.

"Lori tells me you're having a bit of a hard time financially. Is that true?" he asks.

Oh my God, that big mouthed bitch! I thought. "Yeah, it's true. I'm looking for a job though. Something will turn up."

"Well . . . this needs to stay between the three of us for obvious reasons. But I think I might be able to help you out if you let me." He said in a very hushed tone.

"Who's the three of us?" I asked, still very stoned.

"You, me, and Lori. She told me about your financial situation and brought me out here so we could talk about it. Maybe work something out."

"What? Are you a loan shark or something? If I don't pay you back . . . ." and then it hit me. He was looking to pay for some sex. I'm sitting there with my mouth hanging open in shock thinking "he's gonna offer me 50 bucks for a blow job. . ." I was going to kill Lori. I was speechless.

"Look Jessie, I'll be frank. I know I'm an ugly old man. 42 is not that old by the way. No woman who looks as beautiful as you would even think about having sex with me. In fact most women in general wouldn't consider having sex with me. I know this. I also know that I am filthy rich. I have plenty of money to help beautiful young ladies in financial distress. I'm your knight in shining money. Name your price Jessie".

I ponder what he had said for a moment. "You think I'm a whore?!" I asked.

"On God no! On the contrary Jessie. I could go out and buy all the whores I want. What I like is beautiful, young, tight bodied stunners like you. I know I have no chance in hell of spending money on someone like you within a relationship. Well, I'm willing to spend money like that OUTside of a relationship on a woman, if you see where I'm coming from. This is not the first time I've done something like this. Every woman I've been with under similar circumstances has been completely satisfied."

More pondering on my part. He gave me an inquisitive look. "I'm THINKING!" I snapped with a slight grin. He held up a hand and leaned back and said "take all the time you need dear."

"OK, you be completely honest with me and I'll be completely honest with you, OK?" I finally said.

"OK."

"What's the most money you've paid for something like this?"

A long hesitation on his part. "Ten thousand dollars? From dusk to dawn?" My heart about jumped out of my chest. I was shocked. I was expecting a few hundred dollars, not 10 grand! And then when you look at him. . . I could relate to what he was saying. He was truly an ugly man. I really couldn't judge his body as we were all dressed in long shirts and long pants. He seemed to have the average guy's physique. He had good posture and carried himself well. His face though; yeah, he was really ugly. At least his teeth were still all there (as crooked as they were) and clean and white. His eyes were droopy and he had a horrible comb-over. Virtually no chin to speak of which gave him a Mortimer Schnerd look. Yes, uncle J was a very ugly man, on the outside. On the inside? On the inside he seemed to be a truly wonderful person. We spent 4 days together talking about all sorts of things. I heard countless of wonderful, heart warming stories about his generosity. I heard one story however that only one of the people there knew about. Lori. Uncle J propositioned her first when she was 18. Maybe twice a year ever since, she would meet him somewhere and give him a lap dance and a blow job for $500. The one and only time he'd fucked her he paid her $5,000 and lasted for well over an hour! She also told me he was hung like a horse. When I asked her how big, she told me she didn't know but that it was longer than both her hands on top of each other. This intrigued me. Lori and I nonchalantly found a ruler. She put her hands together as though she had them around Uncle Jordan's erection. I measured; Lori whispered "at least 11 inches!"

"Are you fucking serious?!" I asked in a whisper. "How big around?!" I ask. She said she could just barely get her index finger and thumb around its girth.

"W o w. That is a big cock!" I exclaimed in our hushed tone. Lori looked at me with wide eyes and said "seriously." We sat in silence staring at the ruler.

"Are you gonna do him?" she asked with a mischievous smile.

"I think I will. I could use the money. I asked him how much he's ever paid for something like this and he said $10,000!" I said.

"That doesn't surprise me at all. If you do real well for him he'll give you even more than you agreed to". Lori said.

"Really!?"

"Really. Jessie, I know he's ugly as shit, but really; he's a great guy. Lot's of fun, he'll treat you right."

A little while later I was alone in the kitchen with Uncle J. As we made sandwiches I whispered "I hear you have a really big cock Uncle J"

Looking around but not stopping his sandwich prep he smiled rather embarrassed like and whispered back "Yes I do. Have you come up with a price my dear?" I smiled and winked and motioned with my head for us to go out on the back porch again. We ate our sandwiches and had a nice little talk.

"I've been thinking. I'd like to take you up on your offer if we can agree on a price; I've never done anything like this before...you understand?"

"Yes, completely." He said.

"Well, you've paid ten thousand dollars for this before. You said you're loaded, I figure you'd pay it again. Ten thousand from dusk to dawn? I'll do it for that. Where and when?"

A big smile came to his face. "How's next Friday at dusk sound?"

"I think I can make that. Where?"

"How's the Phoenix Hilton sound? We'll have some dinner in their wonderful 5 star; a few cocktails . . . retire to the room, smoke a little herb, few more cocktails . . . nice hot sensual shower? Any objections to any of that?"

"God no! Sounds wonderful . . . you'll be bringing cash, right?" I asked kind of embarrassed.

"Yes, I'll bring plenty of cash my dear. I am so looking forward to this Jessie! I'll be thinking about you all week."

Friday came and I was a nervous wreck. If I go through with this I will officially be a whore. At least I'll be a whore with lots and lots of much needed cash. I could make a phone call, swallow my pride and apologize and my mother would send me a check for 10k, all I need do is ask. That wasn't about to happen. My stupid pride wouldn't let me.

Dinner went very nicely and Uncle J put me at easy with his charm. I couldn't help noticing how truly ugly he was. I feel so bad for saying that, but it's true. I've always tried my hardest not to be so superficial with something as petty as a persons looks. But honestly, when it comes to an intimate rendezvous such as I was about to have – looks matter. I'd had a couple of one night stands, and it was all about how good looking he was. This was the first time I would have sex with somebody I wasn't physically attracted to.

When we got to the room I was already a bit tipsy from the cocktails at dinner. He broke out a joint and we burned it. That was a major help, the buzz put me in the right mood. He poured us a brandy each and we sat at the table across from each other smiling. I opened my legs so he could see up my dress. "Are you shaved?" he asked, not looking away from the view up my dress.

"Mmmm, you like shaved pussy do you Jordan?" I said seductively licking my lips, giving him my naughtiest smile. He looked up and smiled. "Y e e s I do. Do you shave yours?" he asked again.

"Shave and wax sir. I hate pubic hair! Would you like a closer look?" I asked as I pulled the hem of my dress higher on my thighs. I opened my legs ever so slightly more. "OH Lord Yes! I would love a closer look sweetheart!" he said like a 14 year old, slightly squeaky, and slightly masculine. Jordan started to slide out of his chair into a kneeling position in front of me. I stopped him with my foot. "Not so fast mister!" I warned. "I'll show you mine if YOU show me yours . . . let's have a look at that big cock of yours that I've heard so much about." Jordan smiled as masculine as he could and leaned back in his chair. (He was adorable!) He quickly began unbuckling his pants. It was like he was getting ready to show off his coolest toy, and he couldn't get it out fast enough. He finally managed to get himself undone and slipped his trousers down to his knees. As he leaned back, he slid his hips a few inches forward, and just like that: The largest human penis I had ever seen in real life was on complete display for me. I just could NOT believe my eyes! It was enormous! Without a doubt, it had to be just like I was told, eleven inches! And not nearly as fat as I thought it would be either, I found that rather odd. Its thickness was about average. Lori was telling the complete truth. Just about the size of my cupped hand. I leaned forward in my chair to get a better look. I didn't know it then, but Jordan said I had the look of wonderment and awe on my face. "Whadaya think Jessie?" he asked.

Not taking my eyes off the enormous, fully erect cock-zilla in front of me, I answered "That is the biggest, longest cock I have ever laid my eyes on Jordan!" I was awestruck. It was magnificent!

"Yeah, I know. . . I get that a lot." He said with a smirk. It was the comic relief I need and I burst into giddy laughter. Jordan did too! As we were laughing I reached out with my left hand and wrapped my hand around it. Sure enough, perfect fit. I reached out with my right hand and wrapped it around the monster right above my other hand. (You know that thing you did when you were playing baseball with all the neighborhood kids? Where you toss the bat in the air, somebody catches it, and you start stacking hands one on top the other . . . the one who covers the top goes first? Well, that's what I was doing with Jordan's penis!). I removed the bottom hand and moved it to the top, almost covering the tip. With the palm of his hand, Jordan covered the top of his penis and said "I win. I go first!"

I leaned forward with a slutty grin and started to put him in my mouth. As I hovered above it about to 'go down' a waft of B.O. filled my nose and I stopped. I leaned back up and smiled with a little embarrassment and said "E-hem...um, Jordan . . . before we get started here, why don't we take showers and get all squeaky clean for each other, huh?" And I eased back into my chair smiling. He smiled back very nasty like (Lord the man was ugly! <I'm SO SORRY for saying that... just . . . GOD!> but I knew how to act. I had a really good teacher with my first (and longest relationship to date) college boyfriend Spencer.

I was now leaning way back in my chair, my ass on the very edge of the chair. I opened my legs again. He stared with lustful eyes up my dress. "You have something for me Uncle J?" I asked rather pouty. He stood up and his pants fell to his ankles, his monstrous penis standing at attention in front of him. He grabbed the shaft of his manhood and pointed it at me and said roughly "Yeah, I got something for you!" and stood there oblivious to what I had just told him about showers.

"Actually, I was thinking something that smelled like money, green. . ." I said somewhat sarcastically. It was as though Jordan had come out of a trance and realized I was referring to the ten thousand dollars we'd agreed upon.

"Oh my GOD! Of course! I'm so sorry... I'm an idiot. . ." and with that he turned and took a step in the direction of the bar area and fell flat on his face. "Oh Jesus, don't I look like an idiot!?" he yelled as he feverishly kicked his shoes and trousers off. It was a very comic struggle, I'm sure he was faking a lot of it simply for a comic gag. It worked. I was unsuccessful in repressing my laugh. He was adorable!

He retrieved an envelope from the bar and handed it to me and said with a boy like grin, "Sorry about that. Just got kind of excited there."

Smiling back I took the envelope and peeked inside at all the hundred dollar bills. "I'm certain it's all here, I won't insult you by counting it. I trust you Jordan." He lightly patted me on the face and I kissed his hand. I jumped to my feet and said "I'm FIRST! And ran to the bathroom, and slammed the door shut."

"HEY! What about me?!" he yelled.

My overnight bag was already in the bathroom, full of all my props and lotions. I reached in and pulled out my high school senior yearbook. I trotted back out and Jordan was standing there pant-less hitting his pot pipe. He looked up and said "That was quick!"

I handed him the book and said "Here's something I thought you might find interesting to peruse while I get all gussied up for you." I blew him a kiss and a wink and went back into the bathroom to take care of business. I quickly got out of my clothes and sat on the toilet. While there I got out of my bag my high school cheer leader uniform and arranged it on the little bench. I smiled knowing how much he'd like seeing me in it. Spenser was crazy about it! We used it often in our sex-capaids. Spence told me every guy on the planet lusted for cheer leaders. My uniform was the 'real deal'. A high quality set of garments, custom made for each girl. I was very proud of myself for staying in good enough shape to still fit in it. When Spence and I first began 'using' it, I had a few minor alterations done for a better fit of a slightly more robust 23 year old body. Our colors where blue and white. The uniform was a two piece with a shell top and a 16-Pleat skirt with contrasting blue and white color pleat panels and a back button and zipper. The brief bottoms I would not be wearing. White bobby-sox and blue sneakers rounded out my ensemble. As I sat there I found myself for the first time actually looking forward to the upcoming encounter. All week long I would find myself staring blankly into the mirror getting ready for class. I kept thinking "I'm going to sell my body for ten grand to a guy with an eleven inch cock?!" The biggest one I've ever had was probably around eight inches. I did some research online. The average male penis (when erect) is 6.5 inches. That's decent; I've had many about that size. The largest penis ever documented was 13.5 inches long. (OMG!) Another fact that I came across was 75% of all males reach orgasm within 2 minutes of penetration. I found that very interesting. I guess it would be more interesting had I not felt the statistic was accurate. Most of the men I've had sex with left me wanting more. Here I was, probably less then an hour until I was going to let a man (a really ugly man) with an eleven inch cock have his way with me. I was certain he wouldn't completely fit in my vagina. Seven inches will bump my cervix every time. My mouth? I didn't know. I can indeed deep throat. Like I said earlier, the biggest I've ever done was eight inches. I swallowed every single inch with no problem. Anally? Eleven inches? Wow, I just didn't know. I was kind of excited yet kind of scared to try. But try I would, because I am one of the rare women who love receiving anal sex. Statistically speaking, only 12% of women enjoy anal sex. I believe myself to be in a smaller category of women who adore anal sex.