I found myself alone and it wasn’t even 10 a.m. yet. I’d enjoyed jacking off first thing, then coffee, then a throat fuck, and finally got to fuck a tight asshole. My day seemed complete already.
I spent the next couple of hours tending to routine maintenance items on the boat. Cleaned a couple of filters, filled the wet-cell batteries, checked the motor oil. As it was now mid-day, it was time to seek out some lunch. I gathered my things and walked down the dock to the road. I could see mostly houses one direction and some businesses the other. I headed that way.
As I walked along, I smoked a joint in celebration of the excellent morning I had experienced. Feeling no pain, I spied a diner and went in. A classic, Florida diner. All the counter stools were taken so I slid into an empty booth.
As I surveyed the menu, an attractive woman, complete with apron and name tag approached. She was in her early 40’s, had pleasant looking love handles and enormous boobs. Her light brown hair was shoulder length and her eyes were hazel, with a definite twinkle to them. Mischievous, I thought.
But her rack commanded all the attention. It was easily one of the biggest racks I had ever seen outside of implants. And, by the way these were bouncing around, they appeared natural. I had a hard time trying to estimate but they could easily have been a 40EE. It was hard to keep from staring at them.
I tore my eyes away from her chest to read her name tag: Cassie. “You’ve stared at my chest long enough. Time to look at the menu and tell me what you want” she growled at me. With a smile and a bright but sarcastic voice I replied “Nice to see you, too, Cassie. What can you recommend?” “It’s a fucking diner, dude. You want coffee and a piece of pie? How about a hamburger? Or maybe go all out and have the steak and eggs. It’s up to you but make it quick. I get off at 1. Only another hour to go.”
“Gosh, I didn’t know it would be that complicated” I snarled back at her. “I’ll have a hamburger, medium, fries and a small salad, please.” As she twirled around I called “Oh, and a coffee, if it’s not too much trouble!” As she spun around, her oversized boobs swayed considerably under her loose shirt as if they were trying to escape.
A short while later, Cassie brought my burger and fries with a small cardboard cup of cole slaw and my coffee. She put them down, giving me a pleading look. “I’m sorry sir, we don’t have salads, just cole slaw. And I didn’t mean to be so short with you before. I apologize. I just got reamed out for something that wasn’t my fault and that I have no control over. Ah, well. C’est la vie.”
Her tone was apologetic and she seemed genuinely sorrowful. “That’s okay, Cassie. I understand. We all have our moments, don’t we?” “You can say that again” she replied.
I finished eating just before 1 and Cassie stopped by my table to clear my dishes and leave the check. “Thanks, mister. Hope to see you again when I’m having a better day. I’m a school teacher by day. Only grind away here at nights and on Saturdays. These Saturdays are a bitch.” “Thanks, Cassie. Sorry you had a bad day.”
“Well, shit happens. Guess I’ll just go home and start day drinking. Nothing better to do and it’ll help me drown my sorrows.”
“Hey, I’m new here, just came in on my boat down at the marina. I’ve got nothing to do. Maybe I could help you drown those sorrows. Especially if there’s day drinking guiding us.” She folded her arms under her giant rack, pushing them up prominently, tilted her head and examined me. Her hazel eyes got that twinkle back, a mischievous look in them, and you could almost hear the wheels slowly grinding in her head as she weighed the alternatives.
As we walked around back to her car, my mind was flowing. Those big tits were swaying side to side, I wondered if she had pussy hair or clean shaven, hoped I would get her in bed. As we drove the short distance to her house, we made small talk. Life aboard a boat, life as a teacher, nothing serious. With every bump in the road, her mammoth jugs bounced up and down. I just wanted to grab hold of them, squeeze them, suck on her nipples. They were mesmerizing.
We got to her house, a standard concrete block Florida ranch in an older ‘shotgun’ neighborhood full of identical houses, and went inside where it was air conditioned. She told me to sit anywhere and disappeared into the bedroom.
I sat on the sofa and surveyed my surroundings. A bit cluttered but not dirty and not a hoarder. There were various things strewn around, signs that a single person lived there. Alone. Not unlike how my boat gets.
She returned wearing a pair of loose fitting print pants with an oversize pullover top. It, too, hung loosely, hanging down from her oversized rack. She obviously didn’t have a bra on because her nipples poked out and her large areolas were dark and plain as day underneath. Her tits were swinging side to side as she moved about.
“Come join me in the kitchen” she offered. “We’ll survey what’s available for our day drinking session.” We took stock of her liquor cabinet and settled on martinis. She had a virgin handle of gin with a fifth of vodka to back it up.
“Let’s sit on the back patio” she suggested. I followed her there and we sat at a table to begin our ‘dance.’ As we finished glass after glass of the social lubricant, our conversation was varied, touching on many topics. Because she was a teacher, she was well read, intelligent, informed about current events and held her own in everything we talked about. After three or four martinis, my tongue loosened up.
“So how do you like living alone, Cassie? You said no boyfriend, never married. Do you get lonely? What do you do about your physical needs?” Her hazel eyes had lost there luster from the booze, but they sparked right back, flashing at me. “Oh, wow. You wouldn’t believe me if I told you.” “I just might. Give it a whirl. I mean, you’re attractive, you have beautiful, expressive eyes, and you must be able to use your God given features to your advantage” (looking directly at her boobs).
“I do capitalize on my oversized chest. But being a teacher, I have to be careful. There’s a private website that I belong to. I have a weekly show, two hours long, where guys tune in to look at them, watch me play with them, pay me to do strange things with them. They get a rough workout for two hours, every week. Make around $500 a week exposing myself.”
“Holy shit! I had no idea. How much would it cost me to see them? How much extra to actually touch them?” Without skipping a beat, she pulled her top up over them and let them dangle in thin air. She reached one hand out and grabbed my wrist, putting my hand on her right breast. I started squeezing and she abruptly pulled my hand away, pulled down her shirt and said “Not yet. I need another drink and we’d better go inside where it’s private.”
Once we got inside, she pulled her top off over her head, letting it fall to the floor. She stepped over to the counter to pour more alcohol and I stepped behind her, reaching around and fondling her tits. I twisted her now hard nipples between my fingers and grabbed as much of her breast as my hand would hold, squeezing and pawing at it. She just stood there as I mauled her boobs. Soon I slipping one hand down past the waistband of her pants. No undies, of course, and no hair either.
She turned around and grabbed my head in both hands. She pulled me toward her and started kissing me. Hard, deep kisses, with a lot of tongue, a lot of passion. You could feel the built-up sexual urges she had on full display. I’m guessing that she hadn’t had sex with a live person in quite some time. As she kissed me with her wet mouth, I took advantage of the free titty time. I cupped them, I squeezed them, I pinched her nipples. I was manhandling her boobs the same way she was manhandling my lips.
Finally, I felt her hand drop down below my waist. It found it’s target and she rubbed my now hard dick through my shorts. She was still devouring my mouth with hers as she rubbed and grabbed my package. When she broke away to catch her breath, she chugged her freshly poured drink and poured another. “Come this way” as she grabbed my wrist and pulled me toward the bedroom.
In the bedroom, she turned and locked her beautiful hazel eyes on me. “Let’s even the playing field” she said as she unbuckled my belt. As my shorts fell to the floor, she pulled her print slacks off. You could tell that she was hungry, hungry for some sex other than just showing off her well developed rack to a computer camera. “Off with the boxers, mister” she said matter-of-factly. Once I had slid them down, she grabbed my cock, squeezing it and rubbing it, as if it was an old toy that she had lost and just found again.
She lay down on the bed, spreading her legs, as her enormous breasts flattened out. Before I could really react, she grabbed my hand and pulled me down next to her. She grabbed my head in both hands and pushed it down onto her right boob. She took one hand and held her breast, shoving it at my mouth. I eagerly wrapped my lips around her entire nipple and areola. I suckled on it as she used her other hand on the back of my head to keep it pressed into her mound of flesh.
Eventually, I broke free and climbed between her legs on my knees. I used both hands to take control of her boobs, putting my mouth and lips on one, then the other, then back again. I alternated between her tits, biting, nibbling, sucking, tonguing her nipples. I was drooling all over them so they were all wet and sloppy.
I continued slobbering on her balloon sized jugs, twisting and turning her nipples and nursing on them. I noticed that her eyes were closed and she was moaning as her head turned side to side. Her moans told me that she was enjoying this. Hopefully more than just showing them off to random guys at the other end of a computer signal.
She was as aroused as I was. I began to smell her pussy, even with my head working on her chest. It signaled that her pussy was getting wet and I decided to pay some attention to it. I pulled my head up only to discover that she had one hand working on her clit. No wonder I had smelled her. She had worked her magic on herself; she had gotten her cunt all juiced up for me.
I scooched down on the bed and pushed her legs farther apart. Her fuckbox was clean shaven, her slit glistening with pussy juice with only modest sized outer lips. It was really a nice looking pussy, one that I couldn’t wait to explore. As I was studying her cunt, she reached both hands down and spread her outer lips wide, exposing the whole kit and kaboodle. There was her clit, a nice big one, standing up hard and firm. With her lips spread open, her vagina was visible, luscious looking. She was really turned on and her pussy hole was opening and closing, glistening wet.
I hungrily attacked it with my mouth, latching onto it with both lips, sucking it in like an octopus latches onto things. I sucked as much of her sweet pussy juice as was there, then licked it like a mother cat. Next, I latched onto her clit, holding it between my teeth as my tongue toyed with it. I flicked it with the tip of my tongue, then pressed my tongue on it hard, flattening it against her pelvis. I sucked it in and out, like jacking it off with my lips.
All the while I was attacking her delicious cunt, she had her hands on the back of my head, holding it there so I didn’t stop. I kept up my assault on her twat as she was making increasingly louder sounds of tension building. “Ooooo, yes. That’s nice, okay, wow, that feels mighty good. Harder on my clit, harder. She likes to be abused. Ooooo, yes. That’s it. That’s it.” I’d suck her clit between my lips, sucking it into my mouth hard and fast, letting it scrape against my front teeth. She’d twitch when I did that with a loud “Oh, my, YES!” I’d twirl my tongue around it, teasing it, flicking it. Then I’d repeat myself, getting lots of verbal response from her.
I was loving having my face buried solidly in her cunt. It was a nice twat, sweet smelling and responsive. I don’t know if it was involuntary or if she controlled it but her vagina kept pinching tight and loosening up wide open throughout my time eating her. But we were pretty drunk and maybe I was just imagining things.
My cock seemed like an extraneous appendage, just standing erect, pointing up from my groin. I was so busy, so intent on Cassie’s nice cunt, so much in the moment, that I had lost track of him. So, I pulled my head out of her crotch, took a few deep breaths and pointed him to her pleasure hole. She was dripping wet so he slid right in. As I did so, she let out a moan “Oh, fuck yes! Oh, hell yes! Damn this all feels so fucking good!”
As I began fucking her, she raised her legs up high. I stroked him in deep, then all the way back out. I kept on stroking it all the way in and all the way out as I picked up the pace. Before long I was pounding it up her snatch, trying to slam it into the bottom of her cunt. I fucked her hard like this, occasionally reaching up and grabbing hold of one big boob or the other. I’d squeeze her fleshy boobs as I rammed my dick into her sloppy pussy.
I kept this up until that unmistakable feeling started flooding into my groin. Unable to stop my orgasm from claiming me, I simply succumbed. I continued to stab my cock in and out of her cunt as I unleashed my load. My cum squirts were not in sync with my strokes, some coming at the bottom of the stroke, the next at the top of the stroke. I was beginning to like that feeling, cumming on the fly as I continued stroking, as opposed to unloading my entire cum dump while holding him deep in the hole.
When I was finished, we lay next to each other, breathing heavy. She spoke first “That was wonderful, stranger. Much more fulfilling than my titty show or my usual workout with my vibrator. I enjoyed that. How long did you say you were going to be in town?”
“I enjoyed my time with you as well, Cassie. Thanks for having me over and sharing so much with me. I mean, we made a huge dent in that bottle of gin, we had some interesting conversation and then ….” I chuckled and turned toward her, kissing her lightly on the cheek. “Well, just thanks for sharing so much with me.”
We got dressed and climbed in the car to drive to my boat. The ride was mostly in silence as we both were reliving what had just happened. When we got to the marina, she parked in the far corner of the parking lot, away from any of the buildings. She unbuckled her seat belt and turned toward me, reaching for my belt buckle.
I had a surprised look on my face and she gazed at me with her pretty hazel eyes, mischief in them again. She put one finger up to my lips as if to shush me. In moments she had my cock released from his bindings, leaned over and put her lips on him. “Ahhh…Oh, yes!” I moaned. She bobbed her head up and down, only taking the first three or four inches into her mouth. Her tongue slid up and down on his underside as she gave me a quicky, “thank you” suck.