The Delivery Man

"Hard, please, fuck my little asshole hard, don't worry, you won't hurt me," despite her pleas I couldn't bring myself to thrust hard, at first, but after the second or third stroke my lust overcame me and I slammed into her so hard that I raised her body slightly, her weight momentarily hanging on my cock by her asshole. I pulled back and then rammed it home again, feeling her hip bones against my pelvis.

My hand went to the top of her head to get more force into my thrusts, her perfect white body arched beneath me, I pulled her head back by her long, thick hair and a continuous, low, guttural sound came from her open mouth. I didn't hold back. I fucked that girl like I was trying to fuck years of sexual frustration out and she loved every second of it.

She screamed and bucked and arched below me, urging me to come deep inside her. I obliged, pushing hard enough to lift her knees off the bottom of the bath, my back arched, my eyes rolled back and I blew myself deep into her ass.

The fishing boat arrived and docked as I was walking across the lawn, dressed for sport. The 'model' was a slightly overweight man, an average Joe, dressed as I was. He greeted me as I got into the boat, stepping over a decent marlin and two kingfish lying on the floor. The boat circled the island as we took turns taking snaps with my compact camera. We both changed shirts and snapped some more, holding a fish in some pictures and beer bottles in others. He did his job with polite professionalism and asked nothing.

After such a workout that morning my cock needed some rest, so the day was spent eating seafood and getting to know the partners. The next day I would leave so I wanted to make the most of the evening. I had come so hard that, at my age, I needed to build up my reserves. Elvira and David, the black guy, excused themselves, so I spent the day by the pool, eating and drinking with Eva, Juan, Annie and Tamara. Annie, naked as always suggested a game.

The game was simple enough and I had played a drinking version of it in my youth. Each player had two matches and had to choose to put two, one or none in one hand which he or she then placed on the table. The players then had to guess how many matches there were in total. If you got it right you were exempt, if not you did a forfeit and went to the next round. The privilege of choosing forfeits was nominally mine, though Annie chose in reality, whispering suggestions huskily in my ear, resting her naked breast on my arm.

The first to lose was Eva. It was decided that she had to spend the rest of the game naked; she happily obliged treating us to the sight of her voluptuous body complete with Brazilian wax. Next to lose was Juan. Annie suggested that I say he had to allow the women to spank his bare ass. That went off without a hitch, initially, with first Tamara and then Eva spanking him. Annie lived up to her nickname by 'accidentally' slipping a finger into his ass after spanking him, much to everyone's delight, everyone except Juan. I was glad to see she went off to wash afterwards.

Inevitably I eventually lost a round and, with Annie's help, decided to ask Eva and Tamara to give us a show. They didn't need to be asked twice. Eva, still naked, stayed in her chair as Tamara straddled her, her shorts slipping up to give us a view of two half moons of flesh separated by denim. Tenderly pushing Eva's hair behind her ear she leaned in and began to kiss her, her tongue sliding into her mouth.

Annie lent forward to cup Tamara's pussy and gently rubbed it as Eva parted her legs for Tamara's fingers. Two slid in and the smell of sex wafted up to my nostrils. Annie, noticing that I was hard in my shorts, sat on my lap and ground back and forth while I watched these two beautiful women make love to each other with fingers and tongues. Not wanting to get over excited I excused myself for an afternoon nap.

It was Elvira who was at the door when I woke; she wore a little black number and an insolent smile. Although I felt the urge to be decent, unlike I had with Annie, I let her in without dressing. Her high-heels click-clacked across the stone floor. Her usual grace was missing, she held herself awkwardly somehow. She had worn heels the day before, so it wasn't that. A bad back maybe?

"Would you like a drink?" She asked.

"Actually, I feel more in need of a shower than anything else, care to join me?"

"If you don't mind I will just watch."

Sitting slightly awkwardly on a stool she watched me strip off, shamelessly eyeing my cock as it fell free and, thankfully, thickened under her gaze. There was no offer of help, as with Annie, she simply sat and watched as I soaped myself and rinsed off.

"How about that drink then?" I asked when I had finished getting dressed.

"Sounds great, shall we go to the bar in the fantasy room?" Fixing herself a martini, Elvira cracked me one of those delicious Japanese beers and set it on the black marble counter.

The blue lighting behind the bar and the lack of windows made the atmosphere sensually sleazy.

"So, tonight is your last night," she said, obviously leading to something. "I thought you might like to play a game."

"What are the stakes?"

She smiled. "Good question. How about if you win you choose what to do to me and if I win I choose?"

"Any limits?"

"You're asking all the right questions, smart boy," she smiled again. "None on my part, do you have any?"

If she had asked that same question a week previously I wouldn't have hesitated, but the past two days had been a game changer, I had relinquished control and been rewarded with the most erotic experience of my life and I had indulged myself in Annie's total submission. Still, there were some things I just didn't like.

"No scat, no water-sports and no man-to-man contact."

"Deal," she said too fast, like a salesman closing a deal when he knows the customer has just agreed to be ripped off. "So, what game would you like to play?" She asked. "Poker?" Now my uncle, an inveterate gambler, always told me not to expect to beat someone at a game they suggest. He had also taught me to play a mean game of five-card stud, but I went with his advice.

"Have you seen the games room? There is a pool table in there," where I grew up the pool table was the proving ground of teenage masculinity. I hadn't played in a while, but this society princess would be no match for a misspent youth. Besides I wanted to see Elvira bent over the pool table in those heels and that dress, clichéd as it might be.

The early evening African sun streamed through the window of the games room. While I set up the table Elvira closed the shutters. Pool should be played under artificial light. "Ladies break where I come from," it didn't take long for me to realise that I had underestimated her. Feeling like I was in a cheesy movie, I watched as she sunk one off the break. The game was on. Again Elvira seemed awkward in her movements, not at all the sexy image I had imagined. Still, I was having fun. I momentarily thought about losing, just to see what she had in mind, but my competitive streak won the day and I found myself in the lead and wondering whether she would hustle me at the last minute.

"It's hot in here, do you mind if I take off my dress?" Distraction. That was her ploy. I played along and she slipped her dress up and off in one easy movement. The lingerie was of the finest quality and had obviously cost a bomb, as had what was at her crotch. The leather of the harness was clearly real and the dildo attached to it was so realistic that I had a 'Crying Game' moment.

"No fucking way!" I shouted, half laughing.

"I don't remember you mentioning this in our agreement. You clearly stated no man-to-man contact and I am all woman... see." She pulled aside the enormous strap-on to reveal a landing strip of trimmed, dark pubic hair and a neat little pussy.

As with golf, state of mind is everything in a game of pool. Lose your nerve and your game can go down the toilet in an instant. Bending over the table had suddenly become a problem. It was the presence of that realistic dildo and the threat hanging over my anal virginity, but I fought back the nerves and went hell for leather.

As the eight ball disappeared down the whole she stood, a smile of affected innocence on her face. My heart sank. I genuinely wasn't sure I could go through with it, but my honour was at stake. She stepped towards me and pressed her hot, soft lips against mine, forced her tongue into my mouth. The beauty of this woman, the simmering heat that came off her body and her scent all worked against me. I relented and kissed her deeply and passionately, three days of pent up desire and emotional confusion surged through my lips.

It was Elvira who broke away first. I had almost forgotten about the rubber cock, even though it must have been pushing against me as we kissed. She bit me on the neck, hard enough to make me wince and began to unbutton my shirt. Pulling it off, she licked and sucked first one and then the other nipple, sending a surge of warm desire through me. She dropped to her knees and pulled down my trousers, she gazed up at me as she sucked me into her mouth. Despite my terror I relished her hot mouth on my cock. She pushed her head forward until her nose was against my pelvis, breathing hot air onto my skin as she tried to swallow all of me. She pulled away, a thread of saliva connecting her puffy lower lip to the head of my cock. Her eyes had still not left mine. "Upstairs please," it was not a request and in my state of extreme arousal I didn't even consider disobeying. She pushed me forward and slapped my naked ass as I mounted the stairs.

One of the few times I have visited a prostitute was on a trip to London. The girl met me at the door wearing a negligee that didn't cover her g-string clad, buxom ass. Transfixed I followed her up a narrow set of stairs to her room, her ass sashaying at my eye-level. I know, now, how that must feel, your ass exposed to what amounts to a predatory animal, intent on devouring you. A glance behind me confirmed that Elvira had her dark eyes fixed on my ass. I tried not to think about the strap-on.

"In the fantasy room!" She was getting more abrupt the nearer we got. Opening the door I was startled to hear voices. So much for total control of the doors. The scene was subdued by mood lighting except for a blue-white shape, lit by spotlight, forming an X on the St Andrew's cross. Annie. The cross was tilted forward slightly so that her salmon-pink pussy was just visible below the lobes of her glorious ass. Against the wall stood the two men, naked from the waist up, like slaves or bodyguards, staring straight ahead with their arms folded. Tamara and Eva were in the hot tub.

"In the tub please John," I complied gladly, looking forward to having my asshole firmly underneath me, away from that dildo.

"What a beautiful ass, don't you think John?"

"It sure is," for some reason I had almost called her mistress.

"Do you like asses Annie Fingers?" Elvira said, picking up a black leather cat o'nine tails with a glass dildo-shaped handle.

"Yes, I do mistress," the whip slashed across one buttock, leaving a red fan of welts contrasting with her white skin.

"I like them too, I like them nice and red...to match your beautiful hair."

The whip struck the other buttock, eliciting a gasp from Annie.

"Why do they call you Annie Fingers?"

"Because I like to finger mistress," The whip struck a third time.

"You like to be fingered too, don't you Annie? You like to have your pussy fingered, don't you Annie? You like to have all your little holes fingered at the same time, don't you?" Elvira punctuated her questions with ever harder blows of the whip until Annie's ass shone like an apple on a teacher's desk.

"Yes mistress, I love being fingered."

Elvira walked up to Annie and used the butt of the whip to push open her pussy. She pulled Annie's head back by her hair as she inched the glass butt of the whip into her pussy and began to fuck her with it, slowly. The room was silent for a moment, except for the wet sound of Annie being violated.

Pulling it out, Elvira slid the glistening handle slowly up to her ass before using it to pull one buttock aside to reveal the dusky-pink hole that I had enjoyed penetrating so much the day before. Twisting her face around Elvira hissed into her ear.

"You want to have that ass fingered now, don't you Annie Fingers?"

"Desperately mistress."

"John," she called. "Would you do the honours please?" I stepped out of the hot tub, letting Tamara and Eva towel me dry while Elvira stood, holding Annie's ass open with the whip handle, waiting for me to plunder it with my fingers.

Squatting with my face next to her raw buttock I reached between her legs and ran my middle finger down the crevice of her soft pussy, feeling the wetness I pushed it in, burying my finger in her rose-coloured silkiness. The whip smacked the buttock furthest from my face, giving me a start. "She needs a finger in her ass John," using my index finger and thumb I held her open as I slowly dragged my wet finger from her pussy and across to her asshole, circling it, teasing her.

"Finger my ass," Annie whispered. The whip struck again, making her flinch.

"Quiet!"

The tip of my finger passed through the ring of her ass easily, and then Annie did her trick and tightened her sphincter so that I had to apply pressure to get further, until her asshole was clamped around my second knuckle, then she slowly released it until I was all the way in.

"That's enough!" One last blow of the 'cat' emphasized Elvira's order; I slipped my finger out gently. "Let her suck it," reaching around to find her soft mouth, I revelled in her greedy sucking for a moment, letting my hard cock rest against her burning hot buttock as I did so.

Elvira's heels announced her slow approach. "Tamara. Lubricate us please," she said. Tamara brought a tub of lube, knelt before Elvira and sensuously lubed the dildo. "Annie too please. John, hold her open for Tamara," I parted her buttocks and watched as Tamara applied the lube around her asshole, and inside it, with a long-nailed finger.

"You like to be fucked in the ass, don't you Annie?"

"Yes mistress."

Stepping forward Elvira stared into my eyes as she rubbed the head of the rubbery cock up and down Annie's ass crack. Was she thinking about my ass?

"Do you want it Annie?" Elvira said, pulling Annie's head back by her hair.

"Yes mistress."

"Tell me."

"I want you to fuck my ass mistress," Elvira's eyes closed as she gently pushed her hips forward, Annie's sphincter sliding over the slick head of the dildo.

"Do you want more Annie?"

"Yes mistress, push it right in," inch by inch the dildo slid into Annie.

"Tamara. Finger her pussy. John. Finger her mouth. Let's give 'Annie Fingers' what she needs," I moved to the other side of the cross, finding Annie's face damp and flushed and her eyes glazed. Her lips parted and I lent forward to tongue her sweet mouth for a minute before inserting two fingers into it, pushing down on her tongue. Tamara knelt below me and forced two fingers up into Annie's cunt, the other hand grasped my cock, guiding it into her warm mouth.

Elvira had found a steady rhythm, her hips slapping against Annie's ass with each thrust. Annie groaned through her nose and sucked my fingers. Tamara lips slid along my cock, in time to Elvira's thrusts. Annie's breasts squeezed against the cross with the force of Elvira's pounding, push a nipple against the edge of the rough wood, which I pinched with my free hand. I glanced at Elvira who was watching me with a look of unrestrained lust.

It didn't take long for Annie's orgasm to start building, too quickly for me to come in Tamara's mouth. Her knees began to quake and she stiffened against the restraints. She stopped sucking my fingers to let out a scream and then slackened, exhausted. Tamara stood and hugged me, her naked body damp and hot. The men got to work releasing Annie.

"John! Tamara! Eva! To the bed," Tamara and Eva lay side by side on the bed, while I sat on the edge. Juan brought a bottle of warm oil and handed it to Elvira.

"Oil them up John," I began with Eva, rubbing the oil into her belly and moving up to her massive tits, which fell slightly to each side, the skin glistening under the lights. Turning over she allowed me to oil her back and then parted her legs letting my fingers slip into the warm crevice of her ass and down to her pussy, sliding two oily fingers in when I got there. "Tamara too, John,"

Tamara had exceptional skin, smooth and taut. I oiled her chest, allowing her big nipples to poke through my fingers. She responded with eyes closed, moaning gently and rubbing her knee against my cock. Her back was slightly more muscular than the voluptuous Eva's, with a defined trough down her spine. I straddled one leg, sliding my cock up and down her calf muscle as I drank in the sight of her oily ass under my hands.

"On your back John," Elvira ordered. Eva slid her oiled body up legs, wrapping her tits around my cock and moving up and down. She sucked the head each time it emerged from her cleavage. She sat on my abdomen, her open pussy hot on my skin, and dragged herself up slowly until her clit rubbed against my chin. I felt another hand, maybe Tamara's, sensuously masturbate me as Eva lowered her pussy onto my mouth. Her clit stood proud, accepting my sucking and tonguing, until she moaned with pleasure.

"Annie? Could you help Eva to hold him down?" Elvira commanded, stepping onto the bed. Annie was at my side, freshly showered, and smiling. Eva held one wrist to the bed and Annie the other. Of course I could have broken free but I was mesmerized by Elvira standing over me, the shining dildo still hanging from her waist as she looked down her nose at me.

Tamara was above me, crawling backwards until her pussy was above my chest and her tits swung free above my face. Slowly the dildo appeared and advanced into her, stretching her open, sinking down to the two plastic balls. Elvira began to pound her. Weakening with the fucking she was receiving, Tamara slowly collapsed onto me, my face in her pussy as Elvira relentlessly hammered into her. My tongue on her clit took her over the edge.

Tamara rolled away, leaving Elvira and her wet dildo still above me. Was it my turn? Slowly she unbuckled the strap and flung the thing aside, exposing her pussy. Kneeling on either side of my head she grasped my hair and pulled my face into her sopping cunt. Seemingly at the edge of self control she shoved her clit against my chin, thrusting, trying to fuck my mouth with her little, pink clit. I realised my hands were free and grasped her ass, pulling her against me, slurping, sucking, drinking as she ground down on to me, my lips and chin slick with her juices.

Suddenly she fell to the side and barked "Fuck me...now!" In instant I was on all fours between her legs, looking down at my prize. I pulled back to enter her and felt Annie's hand come between my legs, holding me, aiming me at Elvira's cunt. Tamara and Eva licked and sucked my earlobes, running their hands all over my body. I was a king, ready to take my new bride, assisted by my naked concubines. "I want you to come inside me John," She said. I pushed forward, parting her pussy lips with my cock as Annie held my aching balls.

"Fuck her. Take her. She is yours," Eva whispered in my ear. I began to thrust into her wet tightness. Elvira pulled me in and locked her pubic bone against mine, moving with me, staring into my eyes. I rested on my arms as I rhythmically slammed into her, trying to push myself through her, forcing her up the bed with each thrust. I grasped her wrists above her head and bit her neck and thrust my tongue into her mouth. Annie's hands pushed against my ass, adding to the force of my fucking.