Kayla's Diary Pt. 01

My name is Kayla, I'm twenty-four years old, five-foot, nine-inches tall and one hundred and twenty pounds. I have thirty-four c-cup tits with large areolas and nipples that stick out a good three-quarters of an inch when hard. My waist is twenty-six inches and my hips are thirty-four. I have hazel eyes and shoulder-length strawberry blond hair. My legs are long and shapely and I've been told that I have a cute little butt. Many have told me that I'm pretty in a girl-next-door kind of way. Now that I have told you what I look like, I would like to tell you my stories...

It's nine o'clock on a Tuesday night and I'm sitting alone at a corner booth at one of the many bars in this city. I'm drinking cheap beer and trying to drown my sorrows without getting shitfaced, while also trying to ignore all the guys who are trying to hit on me. The place isn't packed, but it was busy for a Tuesday. After sitting there for about an hour, an older gentleman came over to my table with a couple of higher end beers and asked if he could join me.

I'm not sure why I agreed, since I had turned down all the other free drinks and advances of the other men in the bar. He seemed different though, more like he was looking to share a drink and some conversation, rather than looking for a one-night-stand. And, while I wasn't out looking for sex, I was feeling lonely.

Besides, I doubted there would be any attraction, on my part anyway. While he was a good-looking man, he was tall, handsome and fit. He was also a lot older, if I had to guess, I would place him at about fifty, he still had a full head of hair, - which was good - but it was more white than his original deep brown. So, in a sense, he seemed safe, because he was way, way too old for my tastes.

I found out during conversation that his name was Jackson, he was fifty-two, recently divorced and a highly successful stockbroker.

I kind of laughed at that and asked, "What are you doing in a dive like this?" It really wasn't a dive... it was actually one of the nicer bars in this part of town, it just didn't seem to be the type of place a guy like Jackson would frequent.

He chuckled a bit and explained that 'the dive' as I put it, was owned by his best friend of forty years.

I blushed a deep red and apologized.

He said, "Don't worry about it. I like coming in here to visit with my buddy, and also to support his business, but it also gets me away from the rest of the suits that I work with all day." Jackson then asked, "So, what's your story?"

"What do you mean?" I asked. I subconsciously circling a finger around the rim of my beer bottle.

"You look sad," he said. "That's why I came over here. I thought you might need somebody to talk too."

Once again, I don't know why, maybe it was because he was so easygoing and easy to talk too, but... I started talking. I told him that my fiancé, who I had been with for the last five years had broken up with me this morning. And, when I asked him why, he said that I wasn't adventurous enough for him, sexually. I'm pretty sure I blushed again as I said that.

"And, you know what, Jackson." I said.

"What?" he asked.

"I've been sitting here for the last two hours feeling sorry for myself." I said. "But, he's right... I've never done anything sexually adventurous. He was the first and only guy that I've been with. When we had sex, it was always at night, in our bed with the lights either off or as dim as possible. And hell... I know there's other positions out there, I'm not stupid, but I always insisted on missionary. So, let's face it, I'm what guys would call a cold fish." With that I gave a bitter laugh and finished off my beer in one long pull. "It's no wonder he left me."

Jackson motioned to the bartender for two more, and then said, "I don't think you're a cold fish, Kayla. I just don't think you've found yourself yet, you've just never experimented. It can't be easy to be with your first and only lover for that long, especially if they're not a good teacher. It sounds to me like your ex wanted you to know everything about sex, and adventurous sex at that, without wanting to teach you. Sometimes, you should just jump right into something like that, but at the same time, especially if you are new to it, your partner has to at least make the effort to make you comfortable about doing it." He patted my hand and finished by saying, "You'll find yourself, Kayla. You just have to leave yourself open to trying new things."

We dropped the subject then and just talked about whatever for the next couple of hours. We were both slightly tipsy, but neither one of us was drunk when I checked my watch and saw that it was one o'clock in the morning. I told Jackson that I had a wonderful time, but that I really should get home. I thanked him for listening and got to my feet.

"Wait," he said, "Are you getting a cab?"

"I only live a few blocks away, I'll walk home."

"It's late, and this isn't the best part of town," he said. "At least let me walk you to your doorstep."

I thought about it for a few seconds, then said, "Okay, I'd appreciate that, Jackson."

We walked slow and we chatted, there were a few cars out, a couple of pedestrians, but for the most part, the city was pretty quiet.

We passed in front of a store with a deep and fairly dark alcove. Without missing a step, Jackson slipped into the darkened area and pulled me with him. I started to say something, but he put a finger to my lips and I held my tongue. Without a word, he spun me around to face the brick wall of the store front. My hands shot out to catch myself, which put me half bent over with my ass pointed in his direction.

Before I knew what was happening, my knee length black skirt was up around my waist and Jackson had my thong panties hooked in his fingers. He tugged them down my long legs, and without even thinking about it, I lifted my feet one at a time so he could remove the garment completely.

Jackson went down on his knees behind me - probably ruining an expensive pair of slacks - and with both hands, he spread my butt cheeks and drove his tongue into my shaved pussy.

I cried out from that first contact, fortunately not loud enough for the couple that we had been following less than a minute ago to hear. But, it was loud enough for me to remember my surroundings, so I bit my bottom lip to stop any further outbursts.

His tongue was magic as it ran the length of my slit then danced playfully across my clit a few times. My back arched as I pushed my ass more fully against his face, I could feel the tip of his nose tickling against my anus and even that felt good.

I knew in the back of my mind that I should stop him, but in that moment, my mind was not in control, my pussy was. It felt wonderful having his tongue thrusting in and out of my slippery folds, his lips and teeth nibbling gently on my excited clitoris. And to think, a man that I had met only a few hours ago, a man who was more than twice my age was making me feel better than my ex ever had.

I knew I was on a very public street, even if it wasn't particularly busy now, but I just didn't give a shit. I didn't give a shit that a car could pass at any moment, or that someone might come strolling by any second. Hell! I didn't give a shit if they stopped and watched while I was in the throes of passionate bliss, I might even ask them to join. It was actually a quite liberating experience.

Jackson took his tongue from my pussy and I moaned in protest, but then he placed the saliva soaked tip at the entrance of my virgin rosebud asshole, and a whole new excitement burst through my already tingling nerves. I jerked and bucked against his face. This was a totally new experience that I was thoroughly enjoying. I pushed my cute little ass back against him as he pushed forward, stiffening his tongue for penetration. He wasn't able to get much in, maybe half-an-inch... but it was so new, erotic, dirty and immeasurably pleasurable at the same time, I lost it, exploding in orgasm.

I had to bite my tongue to keep from shouting out, and if Jackson's hands hadn't still been holding my ass, I know I would have slumped to the ground. I could feel my pussy gushing, my hot sticky cum running down my legs. I had never orgasmed this hard before, and I had a virtual stranger to thank for it!

Jackson removed his tongue from my anus and stood up, I heard the rasp of a zipper being pulled down followed by a slight rustling. This is really going to happen, I thought to myself. I was about to get fucked right here on the street, less than two blocks from my apartment. He positioned the head of his cock against my dripping pussy and without even the slightest pause, shoved himself in, his balls slapped forcefully against my clit. I didn't know how big he was, but he filled my cunt quite nicely. I started rocking my hips, timing my movements with his. Every time he slammed his cock home, I pushed against him and every time he pulled back, I did the same, keeping just the head inside me. We were in such perfect harmony that it was hard to believe that we hadn't been lovers for years.

There was nothing slow or gentle about our coupling... it was raw and carnal, and I was loving every fucking minute of it! After a couple of minutes of him ravaging my insides, we both heard voices, and they were getting closer. He rammed his dick in all the way, then held perfectly still. Neither of us made a sound - well, I might have made the occasional whimper - and a few seconds later, a woman and two men passed in front of the alcove we hid in, less than five feet from us. Apparently, there was enough shadow to keep us from making an embarrassing public display.

When they had moved on, Jackson leaned in and whispered in my ear, "Is this too much for you, Kayla? Should we finish up at your apartment?"

"Just keep fucking me!" I hissed and then rotated my hips on his cock to emphasize the point. It was just too hot! That had been close, very close, but it had sent such a thrill of excitement through me that I wanted to do it again, and again, and again. I almost yelled out for the three of them to come back, to be witnesses to our wild fuck. But, at the same time I wasn't sure if I wanted to be caught, or if it was just the thrill of the possibility of being caught.

He started pumping my pussy again, apparently just as willing as I to take the risk. He pushed my blouse up over my breasts, then moved the cups of my bra off to the side, releasing my tits to the cooler air of the night. My nipples were already hard from the excitement of my first public sex experience, but jutted out even harder as a slight breeze washed over them, that same breeze tickled my clit and a shiver ran the length of my spine. Both of his hands found my tits and started massaging, his fingers rolling my stiff nipples, it was too much and I started cumming again. This time, I wasn't quiet about it either, fortunately nobody heard, or if they did, they didn't come by to investigate. I cried out my pleasure as I spasmed, my pussy clamping and clasping his hard-thrusting penis must have been too much for Jackson as well. He was grunting and panting, he held my tits hard - almost painfully - and rammed his cock in one last time to the hilt. His grunt of pleasure and satisfaction told me all I needed to know as I felt his cock expand and his balls tighten up as he pumped load after load of his hot white seed into me. My tightly clenching cunt milking him dry of every last precious drop. And even after he had given all he had, I wanted more... more cum, more sex... more thrills!

His forehead came down to rest on my back, and we held that position for a few minutes, until his cock, still buried in my hungry pussy began to soften and finally slipped from my cum slick folds. We were both panting from the exertion of our frantic coupling, but after a few moments we were able to right our clothes.

Jackson and I didn't say a word the rest of the way to my apartment door, as promised, he saw me home safely, and also as he had promised, I had found myself. At the door I turned to him, the first time I had really looked at him since before we had stopped in that darkened alcove.

"Kayla..." he began.

This time I was the one to put a finger to his lips. I didn't want him to ruin the moment by apologizing, and I didn't want him to ask if he could see me again. If we happened to cross paths again, I wouldn't say no, but I wasn't looking to start up another relationship. It was sex, it had been great, adventurous sex, he had broken me out of my sexual shell and for that, I said, "Thank you, Jackson." Then I turned around, unlocked my door and let myself inside.

In my bathroom, I stood naked in front of my full-length mirror. I could see Jackson's cum dripping form my swollen, well fucked pussy. Little white rivers running down my thighs and legs. I smiled at the sight, I thought about cleaning myself up and taking a shower, but decided against it. I wanted to sleep with that little part of Jackson still on my skin. It dawned on me then that I hadn't gotten my panties back. Oh well, hopefully Jackson had them, his own little souvenir from tonight.

I kept looking in the mirror, I looked more confident, more in control. My ex was gone and good riddance, there were plenty of other men out there... plenty of other adventures to be had.

"Welcome to the first day of your new life, girl." I turned out the lights and went to bed.

The End