Ashley's Story

Ashley just shattered the image Troy had of her. Her answers made Troy wonder though; how much of her fantasy was she actually into? Granted, Troy knew that she never really wanted him in the real world; he didn't think she actually wanted him like that once upon a time. He was curious about the kinky aspects of her fantasy description. Was she turned on by being slapped? Did she enjoy the taste of piss? He decided to go for broke and asked, "Ashley, what's the dirtiest sexual experience you've ever had? What's the one you're most ashamed of?". Ashley responded by going into detail about an incident in high school that took place over a year.

"Once I turned 18 I got my trainer certification and became a weight loss coach at my high school. I did the job hoping that if I was successful, our principal would recommend me to a good college. Right after I started the principal told me I had to take on his son John as a top priority. John was around 300 pounds and as disgusting as could be. I don't know that he ever showered, or put any effort into his appearance. He always wore sweatpants and a t-shirt with some random pop culture reference. The principal told me that if I didn't help John lose some weight that not only would I not get onto a top college, but he would make sure that EVERY college knew that I didn't care about anyone but myself. To make matters worse, John didn't want to lose the weight in the first place. I guess he gave me a chance though since he thought I was hot."

"John told me the only way he would try to lose weight is if I promised him that, for every pound he lost, I would worship his bare feet for 5 minutes. I was disgusted but I had ****; going to a good university was my dream. Those first few months were terrible. For 5 minutes almost every day, I had to get on my hands and knees and become his foot ****. At first he seemed nervous; he let me do my thing without any comments or interruption. Often he would just sit there and quietly jack off. After the first few weeks though he started being more assertive. There were times he commanded me to lick between his toes, try to take his entire foot in my mouth, or even have me lay down on my back and lick the bottom of his feet while he lightly stepped on my face. When he suggested that last one I loudly objected. He just smiled and told me that his Daddy would hate to find out that his son's weight loss coach doesn't care if he's so fat he dies. I hated it more with each passing day, but the diet was actually working so I couldn't stop."

"Once he lost 50 pounds, I thought my job was done. I went back to the principal only to be told that John still had a long way to go; he needed to be 150 pounds or less before I could get a good recommendation letter. He even told me I had to put my best "foot" forward, then visibly smirked at his comment. When I went back to John he said he would only continue if I kept licking and sucking his feet per our original agreement, and I did it completely nude. I sighed and accepted the terms of the new arrangement. From then on, when I would focus my attention on one foot, he would either mash the other foot on my tits, or stick his big toe up my pussy. After another 50 pounds, he told me he would only continue only if he got to take pictures of me while I worshiped his feet. Strangely, while I hated having to worship his feet for the past 8 months up to that point, I had no problem saying yes to this request. I was baffled as to why I complied so easily. Even as I learned that he was passing the photos around to everyone in school and selling them online, I was completely okay with it. Then, one day, after he had me clean his big toe right after pushing it into my ass, it hit me."

"I was starting to develop feelings for him! I guess I was really proud of what he accomplished and honored that my nude body and foot slut skills got him there. I started fantasizing about us going on dates, then afterward he would take me to his house and fall asleep while I licked his feet for hours on end. Maybe after a few months of proving my worth I could start using my tongue to clean his entire body! Once he hit 150 pounds I pulled him aside in class and asked him out. He not only said no so loud that the entire class heard him, he said I wasn't hot enough for him anymore and I should stick to sucking fat feet. To make matters worse, the very next day he started dating my older sister. For months I was **** to lay in bed while my sister and John would fool around next door. Every time I could hear the familiar slurp of her tongue across his sole I would get jealous."

Tory laid there in shock for a good 30 seconds before bursting out in a fit of hysterical laughter. That was easily the most fucked up thing he ever heard. He couldn't believe that all those years he thought she hadn't had any sexual experiences, she was out there doing more fucked up things then he could even imagine. Troy asked Ashley, "did you at least get the letter?" Ashley responded, "I went back to the principal, who handed me a letter he wrote to a made up school called Stupid Slut University. The letter detailed all the disgusting things I did with his son, and even had a few pictures clipped to the back. He said he mailed a copy to each of the major ivy league schools. I guess he got our university's address wrong; they were the only ones who would admit me."

Troy began to feel bad for Ashley. Sure, she was much more of a whore then he imagined. Her story was really fucked up though, and it was being told by someone who really hadn't hurt him at all. He decided that it was time Ashley finally had something good happen to her. Ashley was going to receive his last load of the evening.