No Longer a Big Fish

Finally, she brought her hips up, but did not bring them back down. Instead, she lifted them up slightly higher so that my cock slipped out of her pussy. Only then did she completely turn to me look down at my cock now just out in the open then back up to my face and say, "well you might feel like a big man, but you have a small cock."

I do not know why, but much like the goading she had done before, this got to me. As she said the words small cock I erupted. I began to cum all over, it shot up into the air and came down on my stomach, my legs, and the floor. My cock was not even inside of her, yet I was having a massive orgasm. My eyes were shut tight, and I felt the warm cum continually shooting out of me.

When I finally finished, I was too embarrassed to even open my eyes. I kept them shut not wanting to face the world in which I had just cum to this woman telling me I had a small cock. I felt humiliated. This night I had thought would be the best of my life, instead I felt very low.

"Open your eyes rich boy, we are now done here," Layla finally said.

I slowly opened my eyes. Layla's beautiful face was right above mine. She lowered her head and began to kiss me passionately. I could not explain it, but it was the best kiss of my life. I kissed her back our tongues mixing together as she placed her hands on my shoulders and we made out. This went on for at least a minute before she finally pulled back. She was now seated on the couch beside me, and I was covered in my cum.

"Why..." I began before cutting off.

Layla looked at me with what almost looked like sympathy in her eyes. "I am sorry Ryan, but I knew this was the best way to get it out of you."

"Get what out of me?" I was stammering, there was none of the usual confidence in my voice. "Why would you say I have a small cock, I fucked you in front of an actual small cock already."

"Listen, I am not going to argue, Trevor was tiny, and to be honest you are not actually that small. You might even be an average length. But your cock definitely is not thick, and it certainly is not big."

My head hung down, had I always known this? Had I ever thought about it. I had looked it up one time and convinced myself I must be large, at least slightly above average. I ignored the fact that I was barely above the average size when I looked it up, I ignored the fact that when Selina held it in her hand, she could easily wrap her small hands around it. I ignored the fact Selina and Layla had both never had any trouble taking it all in their mouths, even though I knew Selina had a pretty bad gag reflex.

"I'm sorry to have to be the one to tell you this, but it could work out well actually," it almost felt like Layla was now taunting me.

"How is this going to work out well," I didn't know if I wanted to laugh or yell.

"Listen Selina is too infatuated with you to tell you the truth plus she is inexperienced like you I am sure, so you would never hear it from her," I had to agree with her there. Selina would never say something to put me down. "But your cocky arrogance was going to get you in trouble one day. I don't know how you got so lucky with Trevor. That guy is ripped and plays football but just seems to lack that confidence and well also... you know," she chuckled as she said this.

"Well anyways, I have a pretty good sense for people. I don't know what it is, but I can tell what makes them tick. And your overconfidence felt fake to me. I mean, you aren't even rich. What have you ever done? You just have your dad's money and I bet one day you'll just take over his company too? Nothing you actually did."

She was right. Here we were in an expensive hotel that was being paid for by the allowance of money my dad gave me for college every month. I also had grown up and never been good at sports or school president or anything. I was just popular cause my dad was rich, and everyone loved having a rich friend.

"Again, I promise I am not trying to put you down, well not too much anyways," she laughed to herself as she said this. "But your fake overconfidence was the sign to me. I knew what you really wanted was someone to come into your life who wasn't just infatuated with you from the beginning," I wondered then if that was why even when Layla was giving me all of these strange mixed signals, I had still pursued her so aggressively. "I mean realistically if you didn't have your money, even Selina is way too good looking for you."

She was probably right there too. Selina was the hottest girl in our high school. She had developed a phenomenal body and I saw guys check her out all of the time. I am sure she could have had any guy she wanted except for that I was the most popular one in school. I was not that tall only about 6 feet even, I was not ripped and my face was decent.

"Well anyways, it is okay like I said. Your cock is not tiny or anything, and everyone has something they are good at. You have money. Other guys are good at sports, or can fix things, or have big cocks. It is okay to not be the best at everything. So now I can fulfil your little fantasy of having a whore in your life to take care of you and do things you were too scared to admit to yourself. I can be your reality check you need on the side. I am not a bitch either, so your secret is safe with me from Selina or anyone else you don't want to know it."

I did not fully know what was going on. I just could not wrap my head around it. At no point in my life had I actually imagined this happening. I had never imagined sitting here with a girl telling me my cock was small and that she was doing it for me. In fact, up until just a few minutes ago I had thought back fondly on the memory of humiliating Trevor.

"What about when I fucked you in front of Trevor?" I managed to croak out.

"Be honest, did you really like fucking me? Or did you like humiliating him? All kinks and things like that come from the same place. To like to humiliate him could just as easily turn on you, what if he had pulled out a massive cock and taken control of the room. Selina is obsessed with the power you hold so what if you had suddenly not felt so powerful." I gulped as she said this.

"So why does this work for you? What do you get out of this?" I asked her. I realized that I did not want to just be taken advantage of by this woman.

"Well for starters I am a bit of a whore. Sure, I have only fucked 7 men, but I have sucked off over 50 others. I used to have a setup pretty similar to this in Florida where I am from with a local businessman. He would pay me to watch me suck off men that worked for him or clients of his and then fuck me after they left. I did not tell him at the time but a few of them I would meet up with later and fuck them too. That is when I learned I had a kink for being watched and being used or whatever. That is why when I saw you, I knew right away you would be that for me here."

I was shocked by what she had just told me. She had been paid to suck cock. She had been with 50 or more men in some sexual way.

"How did you pick which ones were worthy of sleeping with and not just blowing?" I felt like I knew the answer before she said anything.

A grin appeared on her face, "well I picked the ones with big cocks of course."

I felt a twinge in my cock as she said that and looked down. I was still covered in my own cum and Layla looked down and noticed too.

"Let's go to the washroom and clean you up," she got off me and grabbed my hand leading me to the washroom in the bedroom. There she pulled off of the rest of my clothes and had me help her out of her dress. She turned on the shower and got in with me. It was a very spacious shower and had more than enough room for the two of us.

She washed the cum off of my stomach before letting her hand rest on my cock. "Would you like to hear how this all started? Would you like to find out if you really like this?"

Her hand was unmoving on my cock, but I felt it twitch, betraying me before I even had a chance to answer.

"Okay."

Layla smiled at me and moved me, so I was leaning against the wall. She then got a little soap on her hand and positioned herself beside me but slightly in front of me. This gave me and amazing view of her ass if I turned my head slightly or of her tight toned body in front of me.

She slowly slid her hand over my cock and began to talk. "Well like I told you I grew up relatively poor, so college had always seemed like a bit of a pipe dream for me. However, as I got older, I got better at sports and suddenly the possibility of a scholarship arose. In grade 12 however, I got an injury after receiving an offer to come play here so I had to wait a year to come here. My mom suggested I get a job."

The way she was telling the story her face was incredibly close to mine. It was almost a whisper, it somehow made even this non-sexual part of the story feel more sexual.

"Well, I decided that was a good idea. I could rehab my injury and make some spare money for college. I only interviewed at one place, the manager hired me immediately to be his receptionist. It was part time only a few hours a week, but he offered me quite a lot of money to do that. I gladly accepted as it would mean I still had a lot of time for other things in my life. Now I was not that innocent at the time, I had already slept with two people prior to this so I knew what guys thought of when they looked at me but the manager, his name was Wes, did not even try and hide it. He would come by my desk all the time, I caught him staring at me a lot and it finally came to a breaking point one day when he asked me to stay late to help him."

Layla was now getting into the story as well I could tell. Her eyes were mostly closed while she talked, and her other hand had dropped between her own legs. She had also begun to work my cock with more energy.

"That night he had a big potential client coming after hours. It was such a big contract they would be negotiating that he only trusted himself to do it. He told me straight up that he wanted me there because he wanted to show me off and use me to lower the other man's guard. He offered me 200 dollars to just stay for the meeting and all I would have to do he said was bring coffee and sit around. It was easy money, so I agreed."

"When the other man showed up however, it was very different from what I was used to for the normal clientele. This man was massive, like 6'4 broad shoulders and had a confidence that other men I had met simply did not have. Something about this man drew me in. I adjusted my skirt so that it showed a little more and I was immediately flirty with him. As the meeting went on, I made sure to put on a show for everything. I brought coffee and bent over in front of him. I giggled at every joke he made. Finally, the meeting got towards the end, and they reached an agreement. My manager sent me to print off the details. At the same time, he said he was going to go to the washroom, and I lead him."

Layla was really working my cock now but suddenly stopped. She moved back against the wall and with surprising dexterity lifted a leg up. "Put your cock in me I need to cum while thinking about Dave." I figured Dave was the name of the man in the story and did not hesitate to turn around and stuck my throbbing cock inside her, though I did feel somewhat embarrassed that she had said she would cum thinking of him. I could not believe how tight she felt. "Do not go to fast though or you'll cum before I am ready," she said as she reached down and began to play with her clit.

"When we passed the copying room, he pushed the door open for me which surprised me. I told him the washroom was just down the hall, but he interrupted me and told me to do what I was really there for. I was taken aback but agreed. I dropped to my knees right in front of him and pulled out his cock. It was my first experience with a cock that was actually big. Sure, some of the previous people I had fucked or blown had tried to brag about their 8 inch cocks but boys will be boys. Which is why this man in front of me had my full attention. It was at least 8 inches long and thick like a coke bottle. It was also covered in veins, and I could help but drool just at the site of it. Again, it was my first big cock so I wish I could lie to you and tell you I gave him the blowjob of his life, but mostly I gagged while I struggled to take any more than the head in my mouth. My mascara was running, and I was slobbering all over his thick cock, but I loved it. He was aggressive pushing it into my mouth even when I thought I could not take more. Eventually he grabbed me under then arms and lifted me to my feet basically throwing me over a table, he yanked my skirt down and stuck his cock in me. Luckily, I was incredibly turned on from sucking his cock and so I was wet, but it still hurt. He did not seem to care as he roughly plowed me from behind bent over the table. It did not take me long to switch from pain to pleasure. Even though it was definitely still rough, for some reason the pain each time he pushed into me was replaced with pure ecstasy. I came after only like 30 seconds and screamed as I came on his massive cock. He seemed satisfied with that and unloaded inside of me just a few seconds later."

"He left me bent over the table and walked out of the door. By time I composed myself, cleaned myself up a bit, and got everything to head back to the conference room with, Dave was already back. I didn't know what to do as he seemed indifferent to my presence. He signed the papers and left without so much as an additional word to me. When he left my manager suddenly pulled out 500 dollars instead of the agreed upon 200. He told me I could have all of this if I sucked him off right there and told him what Dave had done to me. I decided to do it as it seemed like easy money, and I was still turned on from Dave's amazing cock. Wes' cock was probably about the same length as yours, so average at best, but was surprisingly thick, so it was actually a bit of a struggle to take in my mouth as well. But since Dave had just forced his cock into my throat, I was able to take most of my manager's cock. I alternated between telling him about how Dave had used me while jerking him off and sucking his cock. It took him almost no time before he shot his load into my throat. I played with myself while sucking his cock thinking about Dave like I am doing right now with you", the admission that she was thinking of her time with another man sent me over the edge I began to cum. "Yes, cum for me like Wes. Cum for me like Wes did after Dave had used me," she almost screamed this and seemed to have succeeded in bringing herself to an orgasm as well.

A few seconds later I was able to pull myself back to reality, stepping away from her and letting my softening cock slide out of her as she grinned and looked at me. "So how was that rich boy?"

I could not believe what I had just listened to. A story about her getting used by two other people and it had made me cum. But I realized this was still different.

"Well, it was a hot story, but it doesn't really prove your point. That was not that humiliating for me? It was just a story of you being a slut."

"You weren't embarrassed to hear both of them had bigger cocks than you? It wasn't embarrassing that you came to that while I came thinking about Dave?" She smiled as she looked at me noticing my cock had twitched slightly as she said that. "Plus, I didn't say I was going to make it bad for you. I said we can both get something out of this. I am not here to make this bad for you, I am here cause I enjoy it and can help you enjoy it too. I like reliving the big cocks I have had, and I like being watched. Despite what most guys want you to believe, finding guys with big cocks is really hard and so this is another way for me to enjoy it."

I was taken aback by her honesty. As much as it pained me to admit it, that story had made the sex a lot better. It had been so hot to imagine her in that scenario getting railed by some guy with a big cock. I looked down at my now soft penis and felt both a little embarrassed and turned on.

"Well sure but what do I get? All I get is humiliated or at least that is what you mean to do."

"To start you get what you really want. A whore who will tell you all about the lifestyle that just won't ever be for you unless you pay some women to fake it. Plus, you really like hearing about it and maybe one day seeing it. And I am not the type of girl who gets off on the humiliation aspect to it. So, you don't need to worry, I won't tell your friends or girlfriend. I won't embarrass you to the other men unless you want me to, I just enjoy what I get out of it too. Not to mention you already have a girlfriend who is out of your league so whenever this ends between us you won't have to worry about having a girl who watched you cum while listening to stories or watching events like these."

I realized it really was an almost ideal scenario. Whether I wanted to admit it or not, my body could not lie, and I had clearly enjoyed this more than any other sex I had ever had. She was also right, if this ever went sideways it could be ended and I would still have Selina who worshipped me. It all just depended on whether I trusted Layla.

"That all sounds good I guess, but how do I know I can trust you?"

"Well for starters look how I handled Trevor. I never mocked him, I even made sure he felt comfortable leaving. I have never degraded him in any way except while playing with you. Even after the first time when he couldn't get hard and I saw his small cock I did not make fun of him to you or Selina, you can ask her to verify that, plus I brought him back and would have fucked him even though it was so small. I am not a bitch, I just know what I like. I came on your cock the first time because it reminded me of experiences I have had similar to that one in the past. So, you know what I get out of it and its easier to get done with an eager rich boy like you."

She smiled at me, and I really did feel like I could trust her. It was true she had been nice to Trevor, she seemed to handle everything amazingly well, and as embarrassed as I was to admit this, I had enjoyed everything about tonight. It seemed like a good chance to explore this and figure out where I wanted it to go.

"I will think over it after this night is done and we can come to some sort of agreement," I said. I decided I would want to have a think over this and ask Selina some questions to ensure that I did not mess up my safety net out of this.

"Sure, thing rich boy," Layla said getting out of the shower. "So, I guess you want to be done for the night and don't want to fuck me again since you have to think things over?"

She glanced back at me and seemed to wiggle her ass a little as she said this. This woman was pure sexual energy, and I could not help but feel intoxicated by it. Something about her just seemed to read my every thought and she knew how to get anything out of me.

"I never said we had to be done for the night," I quickly replied stepping out of the shower.

We had sex one more time that night, she let me bend her over the bed and fuck her from behind with my hands again cupping her beautiful ass. Even though it was the fourth time I had cum in just a few short hours I still did not last long as she talked like a whore the whole time, she said tons of guys would like to be where I was so I should take advantage of it while I could, or she would replace me. She said guys had railed her from behind like this before and she asked if I liked knowing this. As usual she knew all the right buttons to push and made me cum in just a manner of minutes. Since I was unable to make her cum, she made me go down on her again until she also came, saying she would find someone else to take my place if I did not make this enjoyable for her.