In the morning I wandered up to the Captain’s Lounge, hoping to find Maria. As I hoped, she was there, mopping the floor. “Good morning, Maria! How are you on this fine day?” When she heard my greeting, she spun around and instantly blushed and lowered her face.
“Good morning, Captain” she replied with some embarrassment in her voice. “Maria, I wanted to schedule another time for you to come finish cleaning my boat. Are you interested?” “Well, yes, sir. I can certainly use the money and you paid me very well.” “Maria, I like to pay a living wage. And I’m a generous tipper, too. How about later this afternoon when you get off work here?” “That would be fine, Captain. I get off at 3.” “Perfect. I’ll see you then.”
Knowing that I had a date with my miniature Maria at 3, I just went back to my boat and busied myself with routine maintenance items: cleaning raw water strainers, checking fluid levels, that kind of thing. I wanted to avoid Jenny and Second Chance and all other distractions. I could think only of Maria’s tiny body, her tight little cunt, and the possibility of reaming her asshole. I knew how tight her asshole would be based on her body size and the size of her pussy. It was all I could do to keep from whipping my little guy out and manhandling him as I fantasized about pounding Maria’s teeny, little holes. But I held off, saving myself for Maria.
A little after 3 I heard Maria knocking on my boat. “Captain, Captain! Are you there?” “Yes, yes, Maria. Come aboard, please.” I climbed into the cockpit and helped her as she climbed aboard. We both went below and, after an awkward pause, neither of us knowing if this was a cleaning session or a sex session, she said, “What would you like me to do first?” “Do you want an honest answer, Maria?” “Oh, yes, sir. Please.”
“Maria, in my mind, you have a perfect body. When we made love last time, it was one of the best fucks of my life. I sense that you didn’t enjoy it as much as I did, though.” “Well, Captain. It’s not that I didn’t enjoy it. I did. I really, really enjoyed it. It had been so long since I had any sex at all. But I must admit that first, you were much bigger than my husband and initially it was a bit painful. But it didn’t hurt after we got going and I liked it. Second, I felt guilty because I’m married. Yes, my husband is back in the Philippines and couldn’t possibly know. It’s just my own hang up, I guess.”
“Well, Maria, I’m certainly sensitive to your plight and I can assure you that I’ll never force myself upon you. Any sex that we have must be consensual. I had an encounter once where I was raped, handcuffs and all, and although parts of the experience were pleasurable, the entire situation was repulsive. I’d never want to put someone through that. So, if you’re willing, I’d prefer that we skip the cleaning and get undressed. There. That’s my honest answer.” “If we skip the cleaning, will I still get paid?” “Of course, Maria. Of course.”
Having been given the green light, I reached out and pulled her close. Bending down, I planted my lips on her mouth. She responded and we found ourselves exploring each other’s lips and tongue. We continued making out as I began fondling her tiny little butt cheeks. When we came up for air, I began shedding my clothes. Maria did likewise. This time she had on a standard bra and “granny” underwear. I silently chuckled and reached around to unbuckle her bra.
Now fully naked, we embraced again, kissing passionately as my boner got bigger and bigger. Eventually she reached down and grabbed my throbbing rod, stroking it ever so gently. When we next came up for air, I gently pushed her down into a sitting position on the settee. Her head and my cock lined up perfectly.
I grabbed my dick and guided it toward her mouth. Her lips parted and I gingerly stuck my dick into her mouth. She started bobbing her head, sliding the head of my cock in and out. Her mouth felt good, all warm and wet. She continued with her blowjob but could only get the head and an inch or so of my shaft into her small mouth.
I let her continue for a bit, then started trying to fuck her mouth. I grabbed her head and started pushing my cock farther and farther into her mouth. Once I got it going in about halfway, she pulled her head back and started coughing, drooling, and chocking. “Are you OK, Maria?” “I’m OK but your dick is just too big for my mouth. I have a serious gag reflex and it makes me choke.”
Seeing my dream of sliding my entire cock, balls deep into her throat evaporating, I pulled her head back onto my dick. I slid my cock in and started fucking her mouth again, this time a bit more forcefully, pushing harder and deeper.
After only a half dozen strokes of me trying to find the back of her throat, she again pulled away gagging. “OK, Maria. I get it. Let’s try something different.” “I’m so sorry, Captain. I’m just not very good at sucking cock.” “No problem. Just get on the bed and lay on your back.”
She obliged and I climbed between her legs as I buried my face in her fuck box. She was not shaved and my tongue and lips parted her sparse bush and I began licking her slit and instantly found her clit. It was erect and ready. I concentrated on her clit, licking, sucking, pressing, nibbling. She was now starting to moan and move her hips a bit in response.
“Oh, yes, Captain. That feels incredible. Keep sucking my clit, keep it up. It feels so damn good.” I stayed on her clit for several minutes, occasionally lapping up the pussy juices that began to ooze from her miniscule pussy. She tasted “normal,” meaning that her pussy juice was neither offensive nor exquisite. Just normal. Then I got my fingers lubed with her pussy juice and began finger fucking her.
She was so small and tight that initially I could only get one finger in. Still sucking her clit, I started stroking my finger in and out. She responded with more “Ooos and Ahhs.” Eventually I got two fingers inserted into her cunt and increased the pace of my finger fucking. She was now fully engaged, and her cunt swelled up inside. I started ramming my fingers hard into her twat as I got more aggressive with her clit. Shortly, her moans turned into heavy breathing which got more intense the harder I fucked her with my hand.
After a dozen or so strokes of me slamming my fingers deep into her cunt, she let out a squeal, screaming “Oh, God! I’m cumming! I’m cumming! Oh, shit! Oh, Fuuuccckkk!” With that, her hips jerked up and down and her body started quivering. It ended with a final body jerk, and she lay there, spent.
I grabbed a pillow and told her to raise her hips and I slid it under her ass. Found my lube and got greased up. I got her legs up and out of the way as I lubed up her asshole, tenderly inserting one finger into her anus. She sucked in her breath when it went in. Once I had her asshole lubed and ready to go, I bent her legs up and back, so she was, basically, folded in two.
I directed the head of my dick to her glory hole and gently pressed it in. Her asshole was so very tiny and tight, it didn’t want to go in. After a couple of failed attempts, I told her to relax and all would be fine. Tried again and sure enough, I got the head of my cock past the entry door. Holy fuck it was tight! I began trying to stroke it in deeper but with very little force. I certainly didn’t want to hurt this tiny little munchkin.
I kept pushing and stroking, rhythmically, in and out, in and out. Soon her ass began to loosen, and it became easier to push it in farther and farther. After a couple of minutes, my efforts were paying off. I was now stroking my rock-hard cock fully in and out of her sweet, tiny asshole.
This was by far the tightest hole I had ever fucked. I was nearly delirious and I wanted this to last forever, yet I also wanted to cum deep, deep in her ass. I started taking slow, even strokes going from my glans to my balls. All the way in and all the way out.
I was on top of her with her legs up next to her head. I adjusted myself so that I could start pounding her ass. My strokes got harder and faster. I started ramming my cock in deep, slamming into her. She was so tiny that when I slammed my cock deep in her ass, her body was being pushed that direction. I had to keep adjusting my position in order to continue reaming her asshole.
I kept this up, pounding her ass hard, for as long as I could until that magic feeling started welling up in me. This got me even more excited, the thought of dumping my cum load deep in her ass. I slammed my dick in even harder now and, with just a few more strokes, I exploded.
My orgasm was big and seemed to go on forever, at least 5 spasms. My body shook as my thick cum juice came squirting out of my dick, deep in her hole. Once I had spent my entire load, I just remained between her legs, dick still deep up her ass, not moving. After a moment, I pulled him out and watched my jism draining and dripping from her puckered asshole. The creamy white cum juice ran down her butt crack, dripping onto the sheets. I rolled onto my back next to her, exhausted and satisfied. I had achieved my goal of pounding Maria’s teeny tiny asshole and cumming deep inside. My fantasy fuck was no longer a fantasy.
“My goodness, Maria. That was certainly a wild ride! I need to rest a minute; then can I get you something to drink?” “That would be nice. What do you have?” “Maria, I can offer you just about anything. By this time of day, I usually go for a beer or a scotch. Either of those sound enticing?” “I don’t drink much alcohol, but a scotch does sound mighty good after getting my asshole pounded like that.”
I got up and poured two generous tumblers of scotch with ice. She took hers and, after a tentative sip, she downed about half in one gulp. I began gulping mine and shortly had to refill both our glasses.
Within an hour, we had polished off half a fifth of scotch over small talk. She told me about her life in the Philippines, her family and her coming to the United States. She had come to the US to work, to save enough money to send her kids to school. She had obtained a proper work visa but, unfortunately, it had expired due to her oversight. Now she was basically trapped here, dealing with the bureaucratic Immigration Service to get things straightened out. All the money she was making was going to the attorneys who were representing her. Her dream had turned into a nightmare.
By now I had recovered somewhat, and I was starting to feel a whiskey dick coming on. We were still lying in bed on our backs so I just rolled over on top of her and spread her legs open with my knees. I stroked my cock enough to get it firmed up and guided it toward her pussy. She raised her legs up and I mounted her, pushing my now firm dick into her miniature cunt. It was tight as ever and I was loving it.
With a belly full of scotch and little food, I was now in full on whiskey dick mode. My cock grew rock-hard after just a few half strokes so I started pushing it in farther with each stroke. In a matter of a dozen strokes, her cunt got sloppy wet and opened as wide as it could, being so tiny. Guess my ass pounding got her in the mood, so to speak. With her pussy now wide open, I started stroking deeper and deeper. I could feel that I was hitting bottom and I cranked it up. I started fucking her miniature cunt like a jackhammer, just pounding it in hard and fast.
Maria was the perfect fuck buddy. She just lay there, letting me have my way with her pussy, pounding, slamming, fucking her cunt like there was no tomorrow. My alcohol fueled cock stayed with me and I pounded her for what seemed like forever. I wanted to cum again, so I started talking nasty to her.
“That’s it slut. Take my cock all the way in your tiny cunt. Just let me fuck you till I’m done. Just lay there and let me fuck your pussy all I want. You’ve got a sweet little cunt and I just want to pound it till I cum deep in you. Just take it all in you skanky whore. Just let me fuck you silly.”
This seemed to do the trick because that warm tingly orgasm feeling suddenly swelled up in me. I rammed my whole cock deep into her and unloaded my nuts. After the incredible orgasm I’d had in her asshole, this one was not as intense but still sent shivers up and down my spine. I jerked a couple times as I shot my load, then continued to stroke my dick in and out slowly as it went limp. Her tight pussy just felt so fucking good, I never wanted it to end. Eventually, I rolled off her and collapsed on my back on the bed.
“Wow. Another exquisite fuck, Maria. You have the nicest, most fuckable twat of anyone I’ve ever met. Maria, I’d fuck you absolutely anytime, anywhere. Just so you know. Can you come by again tomorrow, about 10?”
“That’s nice to hear, Captain, but I’m already taken. Just so you know.” “Understood, Maria.”
Before she left, she glanced over her shoulder and announced “And I’d love to come back tomorrow.”