Whatever money I made, I socked away, quickly building up substantial savings. Meanwhile, I ate at expensive restaurants, dressed in expensive clothes and shoes, and had spa treatments, massages, mani-pedis, you name it all on my Mistress's credit. I could vacation wherever I wanted, with permission, of course.
Once, some clients flew me to Saint Barts for five beach and sex filled days. Harvey, Marsha's cousin and wife Peggy, and Ken was their mutual lover. I joined them on their private plane where the fun began as soon as we reached cruising altitude.
Peggy (her real name was Margaret, but the nickname turned out to fit in more ways than one) had walked in on Harvey and Ken in their bedroom with Harvey on his knees and Ken's huge penis deep down his throat. She was surprised but not shocked, and chose to share in her husband's windfall and knelt next to him and took the enormous cock down her own throat. Since then, the throuple had enjoyed many sexual adventures together.
They had met up with Mistress Marsha at a family gathering; when they learned of my existence, they wanted to set up the trip on the spot. From Marsha's description, I had assumed it would be just the three of them, but when I met them at the airport there were three other men there: Hank, a large beefy older guy, just my type; Mason, a tall thin younger Black man, and Trent an average sized white guy with a bit of a paunch, but otherwise fit.
Looking at the numbers I assumed it would be a five-on-two scene, but Peggy made it clear right away that other than sucking Ken's gorgeous cock, she intended to stay on top. She was a big blonde bombshell with massive tits that might have been implants, but so well-done that it was hard to tell. She had a very pretty face, and though plump, had a very sexy curvy body.
It was clear from her manner that she was not down with the decision to bring the extra guys; maybe she was not particularly fond these guys, or, wanted to have a more intimate experience than this. I never did figure out. The guys seemed to relate very well with Harvey, while her responses were tense.
Harvey was a nebbish; a slight thin man, just a bit taller than me, though much more manly with a studied stubble of facial hair. He had a salesman's bearing in the way he presented things and often pointed to the luxuries he was able to provide through his affluence. This seemed more a nervous tic than true arrogance.
Once on the plane, Peggy wasted no time demonstrating her enormous strap-on. The men all undressed, while she waved the massive dildo. She was wearing a very short skirt with no underwear. She slipped out of it and inserted the smaller inner dildo, meant to stimulate her pussy.
She pointed to the floor, and I knelt in front of her; she smacked my face with the heavy rubber cock, then thrust it down my throat, making me gag with on it. This thing was colossal and even with my experience and the wider mouth, I could barely get it down. She laughed scornfully as she tried to hammer in further than it could possible go and smacked my face. I would have loved this, had it been a real cock, but the taste of rubber is just not the same. However, I did my best to pretend and worship it like real cock.
The guys were now all naked, and surrounded us. They tore off my little sissy outfit and slapped me with their real cocks, while I choked on Peggy's fake one. They jockeyed with her for access to my mouth; she resisted, except when Ken nudged her. Ken's cock was marvelous. It was shy of Noah's twelve inches, but it was maybe just little fatter and delicious. It tasted particularly good after the Peggy's rubber cock.
I was really enjoying Ken's beautiful cock; and Peggy seemed to tense up even more and smacked me with her giant rubber strap-on. Meanwhile, the other guys were feeling me up, pinching my nipples, and rubbing my ass. Ken gave way to Hank, whose cock was not as huge, but still large. Mason grabbed my right hand and put his sizeable, though thinner cock in it. Trent did the same with my other hand.
Harvey gently bumped Hank to get into my mouth; his still average but much smaller cock went right down my throat easily. I did that thing where I continue to swallow with the cock down my throat. I could see Harvey's eyes roll to the back of his head, as I submissively looked up, lapping his balls with his cock deep down my throat.
They sped up their turns, so I was getting a few pumps from each then onto the next swiveling my head around to get access to each one as they pulled me this way and that. I just surrendered and let them do what they wanted. It was big Hank who first began to grope my ass, and when he found my hole, buried one fat finger then another in there with no lube. It burned a little, but then he spat on this hand and rubbed it into my hole making it little easier.
Hank forced the issue, obliging me to rise from my knees, while still bent over sucking the other guys and Peggy's big strap-on. He got up to three fingers and spat directly into my hole, while wrenching my buttcheeks apart. I was hungry for his cock and pushed back onto his fingers suggestively. He got the hint right away and shoved his considerable cock in my hole in a swift move, then just fucked hard into me just like I wanted.
Hank was probably not the best choice to go first. Hank had the second biggest and was one of those guys who only fucks hard. He stabbed into me with the minimal lube provided by his spit and pre-cum. It hurt, but I wasn't complaining; if I had a choice, I would have arranged them in "size-place order" starting with Harvey who was the smallest.
It was hard to concentrate on either end as I was pounded in front and in back. Peggy occasionally smacked me with her big heavy rubber cock while the others face-fucked me, sometimes two-at-a-time. Meanwhile she was standing next to Ken and making out with him passionately moaning loudly into his mouth while Harvey watched and waited his turn in my mouth. Her intimacy with Ken seemed to designed to melodramatically taunt Harvey. Who looked her way even as he got his turn in my mouth.
Hank's fucking couldn't last very long, and I thought he would cum quickly, but he was dislodged from deep in my rectum by Trent, whose smaller cock slid in easily. He began sensually, kneading my butt cheeks and sliding his meaty endowment at a moderate pace. I was opened and lubed from Hank's pre-cum, so this felt amazing. I began to moan pleasantly on the cock in my mouth.
We continued on this delicious course, and I resolved to let them drive me to my first orgasm. I was whimpering and moaning deeply and Trent picked up the speed. I was getting close, and it seemed that made Peggy angry because just before I could get there, she suddenly moved behind me and pushing Trent of out the way drove her massive strap-on, definitely the largest phallus there, deep into me mercilessly ripping me apart.
She plunged it so forcefully that she lifted me off the floor. Whatever thoughts I had of cumming were driven away by her violent force and the pain from the massive horsecock shaped dildo penetrating gaping l, but not ready for this, hole. The dildo was as long as my forearm. She pushed in as deep as she could; my ass was lubed for the cocks, but relatively dry for this plastic monster. About half-way in, the friction stopped its forward motion.
She finally squeezed a giant gob of lube onto it as she slowly pulled out of me. Her next plunge was less painful, and she managed to get a lot more of that thing inside of me. Ken, who was facing me with his lovely big cock down my throat, reached behind me, opened up my ass cheeks for her assault. I was thinking how much more I would enjoy that beautiful cock in my ass rather than Peggy rubber monster.
I chose to luxuriate in giving my mouth to Ken's big yummy cock. I slobbered over it and licked and sucked with passion. The other guys were getting antsy to have their turns, but Ken held firm using my butt cheeks as leverage and leaning forward to make out with Peggy as she got closer by pushing that monster all the way in me.
I felt so full and that rubber cock was thrashing past my prostate giving me all these tingling feelings. The pain from before had dissipated and Peggy once kissing Ken had modulated her thrusts into me. I was again building to that first orgasm. It was pleasurable to be so full up and the center of attention.
I pushed myself to cum; I moaned and groaned, now driving and grinding my own ass onto the giant phallus. Just then, my attentions on his cock and above me, Peggy's passionate kissing drove Ken over the edge, and he filled my mouth with delicious cum just as I melted into the rubber cock and spasmed into ecstasy. I came thinking of how wonderfully the marvelous cock in my mouth would fill my ass, better than the hard rubber bloodless tool lodged there now. I was seizing nonetheless. She kept her dildo firmly deep in my ass through my orgasm. I licked Ken's gorgeous cock clean and the underside of his balls.