Special Delivery

I was going to come in her hands if we kept this up. I scooped her up. She weighed practically nothing. I laid her down on the bed and got down beside her. We let our hands roam, stroking each other and kissing. She didn't hurry; it went on and on. But she didn't seem to be getting as worked up as I was, so to advance things I tried to go down on her.

She stopped me. "No, no, this is your treat. Here...." She gently pushed me over on my back, knelt astride me, held my rock-hard cock upright and gently sank down onto her haunches, wiggling it into herself as she settled. She waited a beat again, smiling and giving me another chance to look her over, and then started riding me. Smiling at me kindly, she reached back for my balls, jutting out her tits out and intentionally bounced them as she rose and fell. I grasped her hips and met her with thrusts from below.

Watching her was incredibly hot, but she seemed weirdly calm, almost serene. I found I really wasn't fond of getting all worked up with someone who didn't seem to be into it as much as I was. It was like she was humoring me.

A few minutes later she dismounted, slid her boobs slowly down my front and started professionally tonguing and sucking my slimy dick as sexily as possible, licking and sucking and taking enormous mouthfuls until her eyes watered, all while maintaining her most adoring, subservient stare. I was going to come right down her throat. I pulled her up. She sat with her slot on top of my reclining dick, waiting for my next move with a nice, patient smile, wiggling a bit to keep the sensations flowing. Then she inserted me again and continued to wait passively.

I flipped us without disengaging, something I can rarely do. Depressingly, she knew exactly how it works. Then she held out her hands, took mine palm to palm, and interlinked our fingers before moving them onto the bed over her head so that I had to lean my weight on them. She gripped my hands tightly and waited again, so all I could do was fuck her. At last she seemed to get aroused. She started making little noises and those big, soft breasts shivered and wandered. I continued a steady pace and she started to moan, and before I could stop it the rush was upon me and I came and came in her.

She looked pleased. She let go of my hands and put her arms around my neck. We kissed and cuddled for a while. She was just so hot -- beautiful, actually. She was surely the most beautiful girl an underachiever like me could ever hope to have.....

****

I woke up nervous. It was still dark. I should never, ever leave a boat unattended on the ocean. I was an idiot. She was the fuck of a lifetime but.... Where was she, anyway? "Cat? Hey, Cat?!"

"Up here!" She was standing watch. I pulled on my swimsuit and joined her.

She leaned over and kissed me. "That was really nice! Maybe I owe you again." She grinned at me and pushed her bare chest out toward me, invitingly. "I'm going to stay topless. It seems to pay off. The rest of this trip is going to be fun!"

I knew I had to think this through. I didn't really believe she thought I was a red hot lover, and she was probably so experienced that she needed one. And on my side, it was easy to see how I would get hooked on her. I couldn't help liking her and, strangely, admiring her. It was all too easy to fantasize about two itinerant, independent business persons with lonely jobs, two drop-outs who seem to enjoy life and each other's company, kind of bonding. Knowing me, I could fool myself into thinking I could change her life choices and have her fall for me. But everyone knows that's just a trite rom-com plot. I didn't want to be naïve and mistake appreciation for affection. I'd only embarrass myself. And someone might get hurt.

"Look, Cat, that's... very nice, and you are superb. Fantastic. All-world. But there's no need to overdo it. I appreciate the offer, but we're more than square."

"What? You really are cynical, aren't you? What makes you think I can't enjoy a good fucking? I'm not some ancient, dried up street tart! God... that's annoying!"

"OK, OK. Sorry. I take it back. You have to realize I have no way of knowing what you're really thinking. You're so... accomplished!" I'd almost said 'professional.' "But I know you only did it because you owed me a favor. And you didn't even get off, did you? I guess I should just say that I think it would be better for me if we stuck to our deal, sailing for transportation."

She was quiet. Quietly annoyed, obviously. But I didn't want her to realize I was so attracted to her, because that was ridiculous. I'd said my piece. I waited.

"You know, sometimes even I don't know how to push someone's buttons just right the first time! But OK. If that's really what you want. I'll keep my shirt on. You keep your pants on. We'll be fine. I still thought it was fun, though," she added a little forcefully.

We went to strict four-hour watches. Cat stopped being amusing and chatty. Maybe I'd insulted her professionally by resisting her charms. But she didn't complain. She was tough.

Any remaining fantasies died right on schedule as we reached our port and handled the complicated stern-to docking process together. I was under contract to stay with the boat until the first bunch of charterers arrived in a couple of days. Cat was under contract to get fucked by a stranger for a week. She gave me a brief hug and a serious look in the eye, and waved her way off the boat.

I'd dodged a bullet, but I still felt empty.

******************************************

With nothing to do for two days I worked hard remotely and hung out in bars at night. Inevitably, I compared the few girls I met to Cat. Inevitably, they didn't begin to measure up. Inevitably, I stayed lonely.

So it was a relief to welcome the charter guests aboard. The charterer was an obese, surly guy named Anthony, mid-fifties. His trophy bimbo girlfriend was maybe 40. She obviously paid attention to her figure, because she had truly enormous fake boobs. I could only think she slept on her back. She probably spent a lot of time on her back, actually. There were two younger, unaccompanied guys in their mid-twenties who had fun trying to push each other off the gangplank. They didn't seem very sophisticated, or very fit, or very bright, for that matter. One, in my quick estimation, was a wannabe badass. He had slicked-back hair and skull tattoos. The other wore only a Speedo with a big bulge and a bunch of gold necklaces.

I wondered who the sailor was. The big guy lumbered aboard in laced up, heeled shoes that left black scuff marks on the non-skid deck. Badass asked where the bathroom was. Speedo boy had bare feet, so it should take him only a few days to break a toe on the hardware-studded deck of a big, pitching yacht. They asked how we had managed to dock stern-to, with an anchor 30 yards off the bow and only a few feet to spare between the yachts on either side. So, no real sailors, then. I asked whether they knew how to navigate the notoriously shifting shoals of the Bahamas in a boat with a six foot draft. They said they'd figure it out; they had a power boat and a day-sailer up in Chicago.

This wasn't really my problem. I hadn't arranged the charter. I didn't even think I was going to like these people. But I didn't want to see my client's boat get trashed or let these folks off themselves. Without much effort I managed to scare them into keeping me aboard for a few days, 'just to show them the ropes.' Then I reported to my client, who asked me to crew for them for as long as I thought necessary. He'd pay if they didn't, for the safety of the boat.

I showed them their cabins. Anthony was bossy, preemptively taking the big forward cabin, assigning the two others and telling the boys to move in and be ready to go in a few minutes. Their provisions were delivered while they unpacked. Then we re-assembled on deck, and I asked whether they wanted to get underway, or have lunch first.

Badass said they couldn't leave yet. "We have a girl coming. Where is she? She's late! I'm horny!"

Speedo tittered.

And just like that, I knew. This was so Cat! Adventure and sex in the Bahamas, never mind it was with a bunch of sleazebag strangers miles from shore -- she could handle it. And now I was going to have to watch.

I could even guess why she was late. She'd put together the name of my boat and her next assignment as soon as she stepped aboard, and now she wanted to give me time to hand off the boat and clear out before she showed up to ply her trade. Even she must have felt that my watching her at work would be awkward.

But now there was no way out.

While we waited for her I stowed the provisions and opened the cockpit drop-leaf table for lunch. Then Badass put his fingers in his mouth and emitted an ear-splitting wolf whistle, and I saw Cat's tiny white cutoffs coming down the dock. She waved.

There was no point making myself scarce. But I didn't see the point of letting everyone know that we were acquainted, either. They might think I had persuaded them to hire me because we were an item. Or she might need an ally, and a secret ally would be better. I could seem objective if I had to advocate for her, and I could operate secretly if I had to help her. I hung back as she walked up the gangplank.

She shook hands with Anthony. Badass pulled her to him and kissed her full on the lips while briefly fondling a breast. Speedo looked bashful, but Cat swooped in and gave him a chaste air kiss near his cheek. Looking over his shoulder, she spotted me standing behind everyone. I made the zip-the-lips sign. To her credit, she showed no reaction at all. Then Anthony introduced me as paid crew, we shook, and she looked cross.

****

At least the boys knew how to untie a nautical knot. We got out of the marina intact.

It turned out that the boys were twins, and this trip was a birthday present from Anthony, their dad. He explained that his sons needed to get out and see how high-class people lived, as if that explained hiring an escort for them. This was going to be interesting, especially since Anthony was ogling Cat just as plainly as the boys were. The family that plays together, stays together, I've heard. The two kids were completely obnoxious, leering at Cat, running their hands over her, asking about her measurements and cup size, and discussing her body parts as though she were a show dog. Badass once slapped her ass as she passed, but she grabbed his arm and talked to him sternly from an inch away, and when she let go he looked sheepish... for about five seconds.

****

I sailed the boat out of the harbor while they had lunch in the cockpit. The kids sat on either side of Cat. I wasn't part of the conversation, but sitting right there behind one of the big steering wheels, only feet away, I heard every word. All the boys could talk about was fucking her -- when, where, and how, and who would go first. It got pretty wild, so after a bit Anthony thought to ask Cat what her ground rules were. She answered matter-of-factly: "No drugs, no pain, and don't get me arrested. Do you gentlemen have any particular interests?"

"Fucking!" said Speedo immediately. "And tits!"

"I can help you there!" said Cat brightly. She turned to Badass, who said, extra-menacingly, "Tying people up, like on the Internet."

Speedo added, "And watching!" and tittered.

Cat said, "... OK! No charge for watching!" She turned to Anthony and waited. Interesting. His bovine girlfriend was sitting right there, so I was a little surprised that he was part of the deal. But all he said, in his deep, gravelly voice, was, "Better get changed, then, darlin'. The boys are gonna wanna check out the scenery."

****

Due to a notable lack of volunteers I washed the dishes below while Anthony took a turn at the helm. As I was finishing, the bimbo came out of her cabin in a tiny bikini that served mostly to accentuate the supernaturally self-supporting properties of her boobs. She wrapped both arms around me from behind, pressed herself all over my back, gave me a friendly rub between the legs and whispered, "Are you tan like that all over, sailor boy?"

I froze. "Thanks, but I'm just here to keep the boat afloat."

"Aren't you meant to keep the guests happy, too?" she whispered. She stroked my crotch affectionately. Then Anthony called down for a drink. She let me go with a sigh, and I went up on deck for the protective company of the guys.

Soon Cat came up to join us in a pure white swimsuit. Unlike the bimbo's it was a one-piece with full coverage from neck to crotch, in front. She did a little spin, and it turned out to be just a narrow panel that left her sides and back fully exposed, except for a "V" of cords running out of her ass crack and over her hips. It was so narrow and she was so well-endowed that a lot of side boob showed even from in front. The small margin by which it covered both nipples at once presented a constant drama; every guy aboard would be waiting for a tit to fall out. Cat looked at me, and I saw no reason not to give her a nice smile and a big thumbs up. She looked ethereally beautiful and hot as hell at the same time. But boy, was she going to attract a lot of action that way.

Anthony nodded and grunted. Badass said "Niiiiice!" Speedo, standing right in front of her, acted awestruck. For a moment he just stared at her mutely. Then he blurted, "You have really big tits!"

Cat just pulled her shoulders back and fixed him with a luminous smile. "Thanks!" she said. "Maybe you'd like to fuck them sometime." Speedo froze like he was coming in his pants and backed away.

Cat sat with us in the cockpit and joined the conversation, so the discussion predictably turned to her. Speedo said he liked the way her tits bounced when she walked around. Badass asked whether her nipples were sensitive. He reached over and pinched one, and she shivered and wiggled for him in apparent delight.

Anthony was a model of restraint at first, but he couldn't stop looking at her and later, as he was walking by, he complimented her legs and bent over to run a hand up her smooth, soft thigh. She obligingly parted her knees for him, so he ran his palm higher and experimentally rubbed his thumb against the narrow strip of material covering her clit piercing to see whether she would arouse. She closed her eyes, smiled and squirmed subtly against his touch while the bimbo looked on.

****

In the late afternoon Cat went up on the foredeck to sun. Badass was steering and I was standing up on the coaming at the back of the cockpit, steadying myself on the backstay and watching for light-colored shoal water ahead. Anthony was in a nice coma, holding a rum drink and watching the water go by, and Bimbo was resting her head on his shoulder and staring at my crotch, since I wouldn't meet her eyes. Speedo asked Anthony if he could have the sunscreen, and Anthony nodded absentmindedly, so Speedo took it and followed Cat up to the foredeck. All was calm. Despite the staredown, the situation was almost tolerable.

It's easy to get entranced by sailing. There's the water rushing by, the hum of the wind in the rigging, the rhythmic rocking, the splash of little waves against the hull. There's the warmth of the sun and the cool of the breeze competing on your skin. There are the myriad beautiful blues of shallow water in the tropics. I started to think about Cat, and how she could seem soft and inviting but tough and resourceful at the same time. I'd never met anyone like her. I didn't adore her job, but in a way, you have to admire anything done well. Then someone said, "Hey, guys, look at this!" and tittered.

Speedo had led Cat back to the cockpit and was standing next to her, gripping her hand. She was shiny with sun oil, including important parts of her suit, which was now clinging to her chest, completely transparent, showcasing her big boobs with their piercings. Speedo held her there while everyone had a good chance to appreciate his handiwork. Anthony just nodded, but stared. Maybe he was speechless. I was. The bimbo frowned; Cat was shading her spotlight. Badass said "Niiiiice!" again. He reached out and ran his palm reverently over a slippery boob, but Speedo said, "I wanna screw her while she's slimy!" and quickly led her below.

Cat seemed completely unruffled.

****

There must have been some arrangement about who got Cat for the day, because Speedo sat next to her in the cockpit at dinner and she kept a hand between his thighs most of the evening. He was trying to act nonchalant while she occasionally stroked or squeezed his little suit. As soon as dessert was over, before it was even dark, they went below to his cabin under the cockpit, and soon rhythmic sounds and little whimpers of mock orgasmic distress were issuing though the cabin porthole that opened into the cockpit. At first everyone gamely tried to ignore them and keep the conversation going, but a few minutes later Bimbo whispered something to Anthony and they went below. That left me and a drunken, dozing Badass on deck.

Sitting there listening to the muffled sounds of Cat being fucked by a clueless moron had a strange effect on me. I sympathized with her but kind of felt it served her right. I also felt I should be saving her. And fucking her myself, of course, because I was probably not a clueless moron, and she should be attracted to me like I was to her. It was like when the girl I crushed on in tenth grade was falling all over herself for a huge, dumb jock, hardly noticing I existed. I spent the entire year mooning and pining and feeling like a hopeless loser. It made me angry at myself. And at her.

But that was ridiculous. Cat was nothing to me, really - just a super-sexy acquaintance I really liked. Which was pretty much the same thing as my tenth grade crush.

****

The next morning the twins wanted to snorkel. They invited Cat. We piled the boat's snorkel gear into the dinghy and I started the outboard. The boys climbed onto the middle seat and had Cat sit in front, probably because her naked ass was so nicely exposed. It crushed and recoiled enticingly as we bounced over the waves.

We sped a mile downwind to a shallow area and threw out the hook. Badass fell in the water backwards like a professional diver, probably because he'd seen it on the internet. He came up coughing because his snorkel went in upside down and he didn't know he had to clear it.

Apparently there wasn't much to see, because the boys spent most of the time paddling around after Cat and observing her salient parts. When they all came back to the dinghy I helped them struggle out of the water, and we motored back upwind to the boat. This trip was a lot wetter and bumpier, and everyone had to hang on tight. At my suggestion, Cat faced aft to avoid the spray and clung to the gunwales as we banged off the little waves.

Part way there I noticed the boys staring at Cat's obvious pokies. They were dancing crazily in the front of her suit as we bounced along. The boys were ogling her openly, commenting and laughing as her tits bobbed around and neared the edge of the suit. Cat had to hang on with both hands, so they were coming closer and closer to falling out, and she couldn't spare a hand to prevent it. She was wearing a little smile and almost seemed to be teasing them, so it took me a minute to decide whether it would be awkward to acknowledge the problem by slowing the boat. Before I did, a boob cleared the fabric and started bouncing and circling wildly. I slowed us to a crawl, and she tucked herself back in.

Naturally, Speedo knew just what to say. "You look really hot bouncing around like that!"

Badass was more restrained. He told me, "Speed up again! I wanna watch!"

Speedo added, "But leave them both out. That's even hotter."