My worst enemy has always been my hard dick. It has gotten me into more trouble than you can believe. It has also given me a lot of pleasure and a fair amount of pain. The latter is what this story is all about.
She was a tall sexy blonde and she had been dating one of the guys on my softball team. She came to every game, sat in the front row and gave me a hard on every time I looked her way. For three months I had been looking at her and lusting and wondering why I never had a chance at something that choice. The team finished the league a distant third and we had a party at Danny's house to drown our sorrows. She and Hal showed up about an hour into the party and twenty minutes later they had a huge argument and she stormed out the door. It was almost a year before I saw her again and in the meantime I found out that she and Hal had split and both had moved on to other partners.
I had gone to the mall for a new sleeping bag. The zipper on my old one went bad and I found out that the cost of replacing a zipper was almost the same as the cost of a new bag. I found one I liked and as I came out of the sporting goods store I saw her sitting alone at a table in the food court. I debated on whether or not to go up to her, but then my dick got hard when I saw her long legs and my dick made the decision. I walked over to her table and said, "Hi Gayle. The place is kind of crowded so would you mind if I joined you?"
She looked around at the almost empty food court and then motioned for me to take a seat. After I was sitting she looked at me and said, "I can only assume that you are after something. Am I right?"
"You need to explain 'sort of' to little old me."
"Well, what it is is that I spent most of last year watching you and Hal and wishing to God that I could have been in his place. Then you broke up and you were gone. This is the first time I've seen you since and since there is always the possibility that I might never see you again I decided to, as the French say, 'carpe diem' — seize the day! So, if you aren't married, engaged, going steady or in an arrangement with some one else I'm offering myself for any of those just named positions."
She looked at me for several seconds with an unreadable look on her face and then she said just as coolly as you please, "You have a big dick?"
As soon as she said that I figured that it was her way of getting rid of unwanted attention so I decided to give as good as I got. "Bigger than some, not as big as some others, but it has never failed to satisfy." Which was a perfectly true statement; it had never, ever failed to satisfy me.
"I'm going to have to see it before I commit. I like large cocks. You eat pussy?"
I didn't, but since this was going no place I said, "With the best of them."
"Any man of mine will have to be damned good at it. By the way, I'm promiscuous as hell and my guy is not only going to have to be able to handle that, but he will have to eat my pussy when I come home freshly fucked. You think you can handle that?"
Yeah, sure, right I thought, but I said, "Depends."
"Depends on what?"
"I don't care all that much for mixtures. I like the cum I eat to have it's own unique flavor. I'm not too sure I'd be into to going down on you after you came home from pulling a train. I'm not saying I wouldn't, but it wouldn't be likely."
At that point I figured that she would say, "Unfortunately that is just the kind of thing my guy would have to do. See you around." What she said made my jaw drop.
"Come on then, let's go to the restrooms."
"I want a look at your cock. Unless of course you want to stand up and take it out here."
A bluff, right? So I called it. I stood up and said, "Okay, lets go."
She got up and led the way and when we got to the restrooms she pointed at the men's side. "We'll go in that one. If we went into the women's and another woman came in she would go running for security. If a man walks in on us he will stand around, watch and hope he can be next."
She pushed open the door and walked inside leaving me standing there in opened-mouthed amazement. She turned and looked back at me, "Well come on, lets get this part over with."
I began to realize that I was a little out of my depth here, to say nothing of being way, way out of my league, but I took a deep breath and followed her in. She walked to one of the stalls, opened the door and sat down on the pot. She motioned me forward, "Come on honey, let me see what you got."
I had come too far to back out. If I did what my brain was telling me to do I would turn and run, but I knew that Gayle's mocking laughter would follow me all the way out to the parking lot. Better I should just stay and suffer whatever cruel let down that Gayle had planned for me. I unzipped and took out my cock. The damned thing had gotten me into this mess and now it had run away to leave me to face the ordeal alone. Gayle looked at my limp noodle and said, "I do hope it gets bigger. What's the matter honey? Is little old Gayle a little too intimidating for you? Well, you are kind of cute and I want to give you a fair chance so here, let me see if I can help."
She reached out and took hold of my cock and pulled me toward her. She began to stroke it and it responded. "Oh look honey, I think it wants to be my friend. Let's see if I can hurry things up a little."
She leaned forward and took me in her mouth and the blood roared through my veins to my dick and it leapt to its full length. Gayle's hands slid down to my balls and caressed them as her mouth worked magic on me. I expected her to take her mouth off me so she could look at what I had, but she just kept on sucking. Her tongue swirled, her head bobbed and after a couple of minutes the inevitable happened. I warned her I was cumming, but she ignored me and when I blew she gulped and swallowed until I went soft and then she took her mouth off me. She held my limp cock in her hand and said, "Oops. I never did see how big it could get. I guess we will have to do this again. How close is your place?"
I told her and she said, "Mine is closer, come on, lets go."
No longer sure that I was being set for some sort of elaborate put down I followed Gayle to her apartment. Once inside she turned to me and said, "Take it out." This time my dick wasn't trying to hide and it was stiff when I pulled it out. She looked at it, "That's it? That's as big as it gets?"
I nodded a yes and got ready for the put down. "It's not bad. It isn't as big as I would like, but I guess I could make do with it providing you weren't lying about eating pussy."
She saw from the look that crossed my face that I hadn't told the truth.
"You lied about that?"
I told her that I had and I told her why and she said, "Sorry honey, but that is a deal breaker. My man has to love burying his face in my pussy. You might as well put your dick back in your pants and leave."
"No, wait, just wait a second. It isn't that I don't, it is just that I haven't had a chance. I've tried it twice and both times were a disaster. The first time I had been at it maybe thirty seconds when the woman pushed me away and said I was hurting her. The second time the woman let me start and then she stopped me and told me to hurry up and screw her before her husband got home. I'm willing, I just need some pointers and some practice."
Gayle contemplated me for several seconds and then said, "I suppose it would be to my benefit to train you to eat my pussy the way I like it, but if you lied about eating pussy that means you also lied about eating another man's cum out of one. That is also a deal breaker."
"I can do it. Just give me a chance and I'll prove it to you."
She gave me a thoughtful look and then she said, "Okay honey, we can give it a try. Get naked and let's go into the bedroom and I'll give you your first lesson in pussy eating.
That's how my relationship with Gayle started. She taught me to eat her pussy and I was a willing student. She rewarded me with state of the art blow jobs and fucked my brains out. She got me used to the taste of my own sauce coming out of her pussy and I began mentally thanking Hal for breaking up with her and giving me a shot. After that first day there was no more talk of big cocks and of my sucking someone else's juices out of her — at least not until we had been keeping company for two months. One night she called me at work and cancelled our date for the evening.
"Some thing came up honey, something big, and I need to take care of it. I'll swing by your place when I'm done. See you tonight sweetie."