Lindsey's Job

Looking around my room to see if I missed anything I noticed the message light blinking on my phone. Shit. I called Marci the operator.

"Someone name Mary asked if you would meet her at Tequila Mockingbird before you left. Hey isn't that the sheet hole on the beach?" I loved Marcie. She had the worst French accented English you ever heard. Cursed like a sailor at an orgy. "Thanks for taking that message Marcie." I said.

"Want to come down here and show me how grateful you are, Sweetie?" Marcie was about 350 lbs. "I'd love to Baby but I'm heading out for vacation. Another time?" I asked. "You always say that. Au revoir." I hung up the phone chuckling. What the fuck. I had all the time in the world. The next 7 days were mine to do whatever. It'd be nice to see Mary for another send off.

Tequila Mockingbird had to be a front for organized crime. There was rarely anyone there and their weekend business couldn't possibly support it. Mary was at the bar barely wearing a mesh top over a microscopic bikini. Her amazing rack defying gravity as she laughed at something one of the beach hunks was saying. Thee broad brimmed hat shadowed the look of disdain on her face. The poor fucker slobbering over her was oblivious to it. Mary had a sharp mind and a sharper tongue. I'd heard her cut down unwanted attention in less than 2 sentences. This guy was about to make her try harder. This was going to be good.

"Honey, I typically love men whose dick is the same size as their IQ but you, you big hunk of a man, if brains were cotton you wouldn't have enough to put a tampon up an ant." The guy blinked at her for a second apparently recognizing "dick, "tampon" and "ant" but nothing else. He just wandered away.

"That was done well." I said kissing her on the cheek. I tried to sit down next to her but she got up and put me in a lip lock like she hadn't seen me in years.

"You smell like Lindsey." She said when she broke the embrace. "Did you just fuck her?" I nodded. "In the ass?"

"Mary I don't discuss what I do with you to anyone. Please don't ask me to talk about Lindsey with you." I studied her, "Does that bother you?"

Her smile was huge, "You are such a nice man. I like that you don't brag like so many other men. But remember I've seen you fuck her. I've seen you dominate her. I like it. I'd like to watch you do it again. Does that bother you?" she asked.

"You can watch all you like just so long as I get to watch you licking my cum from her." I replied. "What did you need me for?"

"Now there's a loaded question. I'd like for you to spend several hours licking me from toes to ears but I need you to do something for me. It might seem strange to you though....." I raised my eyebrows and waited for her to continue.

"There are some people from my cancer group who I want to give a good time to. Seeing the way you were with Lindsey gave me the idea. You will be mostly passive in this and just enjoying what goes on. The people asked me to keep it anonymous so you'll be blindfolded the whole time. You willing?" she asked studying my face.

It was what Mary didn't say that told me more than what she did say. "People" rather than "women" meant that there was at least one man involved. I'd been in such situations before, albeit not blindfolded, and it did not bother me. I much prefer women to men but I don't go crazy if a man touches me when there are several people all intertwined.

"So long as you are there Mary I'm OK with it all. When do you want to do this?" I asked waving at the bartender. I can never get the barkeep's attention and I wanted something frozen.

Mary leaned over resting her wonderful firm tits on my arm and whispered licking my ear," In about an hour."

I let her nibble on my earlobe for a few seconds before saying, "You're pretty confident aren't you. What makes you think I wouldn't have said NO?"

"Because I was prepared to suck your cock right here at the bar. When I had one of your balls in my mouth you'd agree to do anything!" she laughed. She did have a point: when they got you by the balls your heart and mind will follow.

I never did get my drink so after a few more futile attempts I gave up and followed Mary to the Fontainebleau hotel. The valet eyed my road yacht approaching and ran for cover. I guess he expected a much older man driving. I gave up the keys, got a ticket and entered the lobby. Mary was speaking to an elegantly dressed man with a name tag. As I approached Mary was saying thank you for something and the man left.

"I really appreciate this. I promise you'll have a good time," Mary said heading for the elevators. We got off two floors below the penthouse. There were only two doors other than the elevator. Mary ushered me into the largest most luxurious suite I'd ever been in. The view of the ocean and city skyline was incredible. The sunken living room was carpeted deeply and plush. I kicked off my shoes and decided that this is where all the fun would happen.

Mary disappeared for a minute then returned with a tall single malt scotch. "Go take a shower. I'll be in there in a minute." She nodded her head towards the hall.

The bathroom was the size of my room back at the resort. The tub could easily accommodate 8 people. The shower had dual heads and it too could accommodate several people. I found a place for my clothes then worked the shower heads for a nice cool rain. Mary appeared naked sans wig and joined me. We soaped each other up paying special attention to our favorite parts. She managed to slide a soapy finger up my ass while fucking my cock with her tits. When I felt my asshole clamp down I made her stop. If I was going to cum I wanted it to be able to see it on her skin not be washed away by the water. Mary pouted and smiled deviously.

After we rinsed off completely I sat her down on the bench and ate her to orgasm. In retaliation for the titty fuck, I crammed two fingers into her ass and two into her cunt and sucked her clit fast and firmly with my tongue. My face was soon flooded with her pussy juice as Mary cried out her orgasm.

"OK! OK Enough!", Mary protested. "Do you always HAVE to make me cum so much?"

"Complaining?" I asked licking my fingers.

"Not right now. Dammit my legs are like rubber! You smell like me. You had better was off again. Then meet me in the living room." I turned towards the shower and Mary caught me from behind. Wrapping her arms around me in a hug, she kissed my shoulder then grabbed my cock. "I could get used to this," she purred.

I got into the shower as fast as I could.

After drying off and finishing my drink I wandered to the living room. The furniture had been moved leaving a few small tables around the sunken area. For drinks and other things I supposed. Several pillows were scattered around the area. Mary came out of the kitchen with a fresh drink in her hand. She had a simple wig of straight black hair. Her robe was pure white. The contrast was startling which combined with her height and figure made her an imposing figure. I wondered why she was going for that effect. From the pocket of her robe she produced a large black silk blindfold. Like the kind you would wear to sleep. "Are you sure you're OK with this? I really haven't told you everything." Mary said.

"You haven't told me about the men who will be here and you're wondering how you can do that delicately." I prompted her. I took the glass from her hand and headed to the middle of the living room. The carpet yielded gently to my bare feet. I sat down enjoying the sensation of the soft fibers against my bare ass and balls. Mary sat next to me and began tracing circles on my chest.

"Everyone who will be here is terminal. Not from anything you can get from them but still dying. They are all married or pair bonded. Some of their spouses are present and will be participating. Because of the medication they take sex is a difficult thing for them to manage. The men can't get a full hard on and the women need lubrication because they can't do that themselves. You and I will be the only fully functioning people here. Now I know that there's no place on your body you don't mind me touching. Would it bother you if a man touched you?"

Mary didn't just mean "touch". She was asking me to help her give these people what may be the last good sex they'd ever have. I was moved and anxious at the same time. "I'll put the mask on and if something happens that I'm not comfortable with I'll call for you. OK?" I asked.

Mary hugged me. Then kissed me. Then hugged me again this time opening her robe letting her nipples scrape against my chest. "You are so going to love this. OK it's time to put on the mask. Let me help" I was treated to a face full of tits as she put the mask over my head. She adjusted it to make sure it was comfortable then left me sipping my drink on the floor. I heard rustling coming from in front of me. The sound of many feet across the carpet and a few gasps. I knew I was being scrutinized but since I couldn't see them looking I wasn't uncomfortable.

"Everyone I want to introduce you to a dear friend who was gracious enough to postpone his vacation to be with us tonight. He has some hidden talents that I believe the ladies will love. Now ladies check with me before doing anything to him that you are unsure about. Gentlemen check with me before you do ANYTHING to him. He may look harmless, beautiful but harmless," there were chuckles. "I can assure you he is not. Now I know some of you are pressed for time so who wants to go first?" Mary sounded like an emcee.

I heard no response but felt a trembling touch on my chest. It was joined by others as hands stroked my chest and belly. I felt warm breath on my cock as something pressed against the side of my head. It was a thigh that was joined by another as a pussy settled on my face. I flicked my tongue over where I imagined a clit would be. I heard a gasp above me and knew I was on target. My cock twitched to life when I felt a tongue, wet and insistent travel from the base of my balls all the way to the underside of the head. I knew the woman on my face wasn't doing it so I spread my legs farther apart. Immediately a hand slid down caressing my balls while the other grasped the shaft. A very talented mouth rubbed the head against their lips and then gradually took a little at a time into it. The pussy on my face was trembling now and I could tell the woman was cumming. Slowly my cock was sucked into a throat until I felt teeth against my pubic hair. This cocksucker was skilled!

The person sucking my cock took their time sucking, deep throating, stroking and watching my cock's reaction. The woman on my face sat through three orgasms and when she sat up straight was rewarded by a tongue driven straight up into her ass. She squealed in surprise then nearly broke my nose trying to get more into her asshole. I heard a cry of approval from the other folks. I licked sucked and tongue fucked her asshole all the while enjoying the incredible sensations my cock was experiencing.

"Thomas move off so I can get that inside of me." I heard from above. So it was a guy who had been sucking my cock!

A sloppy wet cunt slid down over the entire length of me. I slid a finger down my pubic bone hitting her clit and was rewarded by a loud moan. I bucked under her but really couldn't get the leverage I needed. Sitting up my cock sunk deeper hitting the woman's womb. I felt sagging tits against my chest and she pulled me closer to her. Quickly I swung my feet out to both sides and put her on her back with my cock still buried. I thrust up grinding my pubic bone into her clit while flexing my cock. Thomas said something I didn't hear then I felt hands on my ass. The lifted slightly parting my cheeks then a tongue lapped at my balls. I continued a slow deep fuck of his wife's cunt while he tongued my balls. Once or twice his tongue flickered over my asshole and I was wondering where that was going but the woman under me cried out again and I felt her cunt squeeze me over and over as she came again. Typically I would have shot off inside of her but I'd had just enough scotch to keep me from cumming easily. I thrust deeply again then held still riding out her orgasm. The man took advantage of me staying still and licked tentatively at my asshole.

Mary's voice broke our concentration, "You said you had to leave early and it's getting to be nearly 3:00. You can stay if you want but I thought I'd better let you know how much time had passed. You look like you two could go all night with him,"

The woman pulled me to her and kissed me deeply. They both thanked me and said they wanted another chance at me. They moved off and hands pulled at my legs moving me up to kneeling. A body slid under me and a hand guided my cock not to a pussy but into a mouth. I felt another mouth on my balls. I was straddling one face while another sucked me.

"Well if none of you mind..." I heard a woman's voice say. I felt movement near me and I smelled the wonderful scent of pussy. I licked out and was rewarded by a hot wet clit. "Ah.....now that's so nice" purred the voice I had just heard. We must have looked like a monster from hell. The mouth below me alternated between sucking my balls and licking my asshole while the mouth on my cock drove itself back and forth. I reached out with my hands following calf to thigh and then around back to ass cheeks. I pulled the pussy onto my face while massaging her ass. When I drove a finger into her pussy I felt a finger enter my asshole. I wormed a finger into the woman's ass in front of me and she howled in protest but made no move to pull my hand away. The finger in my ass located my prostate and rubbed while my balls and cock were getting worked over. That was too much for me. I howled myself right into the sweet pussy on my tongue and I fired a load into the throat around my cock. The two below me scrambled, each trying to get my cum in their mouths. Soon two slick faces were drinking right from the end. With each spurt of cum jetting from my cock my asshole pulsed around the finger in my ass sending waves of pleasure through me. When I finally stopped shooting I nearly collapsed. The finger was withdrawn from my grasping ass to be replaced by a soothing tongue.

I came three more times that evening. I had taken every person there in at least two holes. The men too. At one point in the evening Mary had me on my back while a wonderfully tight pussy rode me slowly. She whispered, "Be nice because Cindy just turned 18 and she's only ever had sex once." I Cindy's wonderful tight ass in my hands as she gently rode me to orgasm. Then got off. Before she could get very far I caught at her leg and pulled her back down. I ate her pussy until she said she was getting raw.

I fucked pussies and assholes, had numerous mouths on every part of me. Had one person, I couldn't tell if it was male or female, rim me so well I could have cum just from that! Some people were fumbling and inexperienced while others were expert. One guy was so good I was thinking that being bisexual sure does have its advantages!

After the eighth or ninth switch I needed a drink. Water this time as I was working hard...fucking hard and didn't want to get dehydrated. As Mary led me to the kitchen I heard a man's voice, "Now where do you think you're taking him Hun?"

"The man needs a drink, Fred. Which is understandable considering you've been trying to suck him dry since you got here. Let the poor boy have a drink!" Mary joked. I drained first one bottle of water then another. "That was what I needed. OK now how about something alcoholic? If I'm going to be fucking all night I need some help." I said.

Mary and Fred spoke to each other in hushed voices. I was getting nervous. Then I felt Mary's hand on my cock. "C'mon with us and get a real surprise." she purred in my ear.

They led me into the bathroom to the toilet. They both offered to hold my dick while I peed but I declined. I never could pee with anyone other than myself holding me. When I finished I just waited thinking they heard the flush and would soon me there. After a few seconds Mary said, "I think you'll like this. It'll be a little weird and maybe even a little embarrassing but you'll like it. Come on into the shower. Fred has something for you."

"Mary I love this guy! Where the hell did you find him?" Fred asked sounding a little "swishy".

"On top of my sister. Are you ready for him? OK kneel on the bench. Careful now. There's a cushion there for you. OK hold onto the back of the bench. Good now just stay like that. Stick your ass out farther," Mary ordered.

Two sets of hands were suddenly petting my ass. I heard a plastic click from behind and above me. "Just relax," Mary said in my left ear. A hand from the right, Fred's, went over my ass and located my asshole. His finger coated my brown pucker with lube. "God I wish I could get hard and fuck this beautiful ass!" Fred complained. He slid his finger slowly into me. When it reached as far as it could he slowly withdrew then back again finger fucking me. I let Fred have his fun. He did know how to use his fingers.

"He's ready, Mary." Fred told her. I felt something probing my asshole. It was smaller than Fred's finger and hard. It slid up inside me a few inches then stopped. I heard a click and warm liquid began flowing into me. I flinched at the sensation but the hands on my ass soothed and stroked. My balls were caressed and the head of my cock was getting sucked from behind. I was being filled and sucked at the same time. Mary was right! It was a strange sensation. The two of them took turns sucking my cock. They tickled my balls with their tongues. Mary rubbed her big tits on my face feeding me her nipples while Fred went to town on my cock and balls below. All the while I was getting fuller and fuller. I heard the "click" again from above me. The enema nozzle was pulled from my ass only to be rudely replaced with something bigger and fatter.

"Did you just pout a butt plug in me?" I asked Mary. Fred continued his oral efforts but mouthed around my cock, "Yes but I wish it was my cock in there!"

Mary whispered, "you can have me any way you want wherever you want if you just play along." I shook my head thinking 'GODDAMN" and nearly fell over. I was fucked up!

"What is in that enema?" I demanded.

"I wanted to put Chateau Haut Brion but Mary said the cheap pinot would work just fine." Fred said from under me.

"You guys gave me a wine enema?" I was astounded at Mary. I couldn't believe she'd do something like that without telling me first. Fun is fun and fucking is fucking but that was over the line. Fred started pulling the plug out a little then letting it slide back into me. I was annoyed with Mary and annoyed with Fred. The next time he fiddled with the butt plug I slid all the way into his throat. I pinned his head to the bench with my cock. He couldn't breathe at all and soon his hands left my ass to push at me.

"He can't breath." said Mary. "I know." I replied. I counted to 30 and pulled my cock from his throat. Fred collapsed on the floor coughing and gagging. When he could finally speak he said, "OMIGOD that was fucking awesome! I just came all over myself. I couldn't breathe! I thought I would die!"

Mary led me to the toilet apologizing about the enema the whole way. "Mary just get the fuck out until I call you OK? Please?" I told her. I spent the next 5 minutes expelling the enema. I was drunk as hell. Much more so than I usually let myself get. Certainly more than I would in my present situation. Goddammit!

I cleaned myself up and staggered from the stall. I had the mask in hand and needed to shower off. After a quick soap job and rinse I put the mask back on. No good. I was too drunk to do this and navigate by myself. "Mary!" I called out.