Mom and Dad told me that the Owner’s Association held a party each month. All of the residents and any guests that they had staying with them at the time were invited. The parties were held at the clubhouse. The parties were catered but one of the complex founding families acted as the host. The next party was scheduled for this coming Friday.
Dad heard us talking about the party and chimed in, “You better get plenty of rest before the party. For a young buck like you, this will be a real test of your endurance and stamina!”
The day of the party, I helped Mom and Dad prepare the place mats and party favors and take them to the clubhouse. The clubhouse was a large building. It looked to me that it would easily hold all the compound members and quests. At one end of the building were kitchen facilities and steam tables. Next to them were about 10 big round tables. Across the far wall, in front of the tables was a raised stage. Moving toward the other end of the building was a large, perhaps 50’ by 50’ area with a thickly padded floor. The far end of the clubhouse contained what looked to me to be an Olympic sized swimming pool and a very large hot tub. Part of each pool was inside the clubhouse and part of it was outside. There was a state of the art high fidelity sound system and several large TVs. It was a magnificent place to host a party.
One corner contained several devices that I had never seen before. There was whatlooked like a swing. It was attached to the ceiling through a number of pulleys. There was also a wooden structure that looked like a large letter X. It must have been almost ten feet tall. There were straps of some sort located at the end of each arm and a belt like strap right in the center where the arms came together.
I asked Dad what the equipment was used for and all he would say was, "You'll find out later tonight!"
Dinner was delicious and as I looked over the crowd, it could have been a church social except for the fact that all the attendees were naked. After dinner, Mom asked me to return some items to our house and bring her some folders that she had forgotten. She said she needed them for this evening’s program.
As I entered the clubhouse on my return, I saw Mom move to the microphone at the center of the stage, “Ladies and gentlemen, please welcome our guest of honor, my son Jack. Jack, please join my here on the stage.” There was a lot of applause and cat calls as I moved to join Mom.
Mom put her arm around me and explained that the compound had a traditional way to welcome a new attendee to their first party.
“You’ve already met some of the residents. There are others who are looking forward to getting to know you much better.
While you were gone, we drew lots to determine who gets to spend time with you. Each person will have up to 15 minutes to make you cum. You objective is to see how many climaxes you can have before the night is over. “Now who has number one?”
There was a squeal of delight in the crowd and I saw Aunt Andrea pushing her way toward the stage. “He’s mine first!”, she almost screamed. I joined her in front of the stage. She wrapped her arms around me and pressed her breasts against my chest. Oh fuck she felt good. She pulled my face down to meet her open mouth and began some serious kissing. She opened her lips and I felt her tongue probing my closed mouth. I opened my mouth and began to use my tongue to duel with hers. The crowd went wild, urging us on.
All of this touching was making my cock rise. Aunt Andrea felt it and reached down to stroke it gently. “Oh Jack, I’ve wanted to play with this big hard cock ever since I watched you fuck Bill’s ass. This time I want to feel it deep in my pussy.“
Andrea took a firm hold of my cock and pulled me across the floor toward Uncle Bill. “Get on your hands and knees!”, she barked at Uncle Bill. She motioned to a man in the crowd, “Get you cock over here and help me.” He was a little older. His cock began to rise, but it didn’t get hard enough to stand up.
Aunt Andrea reached under Uncle Bill, grabbed his cock, and began to stroke it roughly. I couldn’t believe the look of pure lust she had. Then she took the new player’s cock in her mouth and began to suck it fiercly. As it got harder she positioned him behind Uncle bill and aimed his cock at Bill’s ass.
By now Aunt Andrea was on her knees bent over with her ass in the air. She was still stroking Billl’s hardening cock, as she guided the new cock into his ass. I wasn’t certain what my role in this scene was supposed to be, but I noticed that in this position, I could see Aunt Andrea’s pussy glistening from her own juices. It was so fucking hot watching Aunt Andrea help these two old fuckers. Then the scenario became clear to me. I moved behind Aunt Andrea and positioned my hard cock at the entrance to her warm wet treasure. As I leaned forward, my cock slipped easily into her pussy.
Aunt Andrea screamed out, “Oh yes, boy, Fuck me hard and fast!” I felt her tighten her pussy around my cock. The feeling was exquisite! I thought I might cum right then. Uncle Bill was beginning to moan, both from the stroking of his cock and the massaging of his prostate.
“Oh yes, make me cum. Shoot that load in my bowels”, Bill yelled out. He began to shake. Aunt Andrea increased her tempo. I thought she might pull his cock out be the root.
The stranger began to howl, “Oh fuck yes, I’m almost there. I’m going to cum”
The crowd was going wild. They were yelling and applauding. A chant sprang up encouraging all of us to cum. As I looked around the room, I could see women with fingers rubbing their pussies and men getting their cock stroked. The smell of sex permeated the room.
Aunt Andrea, still stroking Uncle Bill’s cock, began caressing the stranger’s balls. She began encouraging both of them to shoot their loads. She looked over her shoulder at me. “Jack, give me your first load of the night. I want to feel it splash against my cervix. Keep it up, you’re going to make this old bitch cum.
The new player was the first to give it up. “Oh fuck, here I cum.” With that exclamation he buried his cock balls deep in Uncle Bill’s ass. I could see his body spasm as he dumped spurt after spurt into Bill.
That did it for Uncle Bill. “I feel you cumming deep in my ass.” I could see Uncle Bill tense up. His load shot out of his now very hard cock.
Aunt Andrea was almost sobbing as she encouraged her husband to enjoy his climax. “Oh baby, I haven’t felt your cock this hard in years.” She caught some of his cum and smeared it around the big purple head. I saw her tighter her grip on bill and at the same time, I felt her tighten her pussy around my straining cock. She began to shake all over.
That’s all I could take. I felt the pleasure start at my toes and work its way up my legs and finally culminate in the very tip of my cock in a heavenly release. All my muscles tightened as I began to cum.
Aunt Andrea screamed as she came two. For what seemed like a long time the four of us seemed to hang suspended in sexual bliss. As I slowly came back to reality, I heard the crowd applauding. They were yelling and howling their approval.
Mom and Dad were still standing on stage at the microphone. Dad had his fingers buried deep in Mom’s pussy. Mom had a hand wrapped around Dad’s big hard cock. “Way to go Jack!” The pleasure phase of the party is now officially open. Who has number two?”
The crowd began to move into smaller groups of two or three or four. It was a full-fledged orgy. As I watched the sex begin in earnest, I saw this petite woman with auburn hair and low sagging breasts emerge from the crowd. “Hi Jack, I’m number two……”
“My name is Alice, but I want you to call me Ali. Your ass is mine for the next 15 minutes, because I’m holding number 2!” That’s the way Ali introduced herself. She began to guide me towards the far end of the padded play area. We had to pick our way across and around the groups of people wildly enjoying each other’s bodies.
I saw Dad locked in a missionary position with a beautiful young woman. She appeared to be about Ann’s age. As Dad drove his big hard cock into her warm wet pussy, she was moaning, “Yes oh fuck yes, you’re going to make me cum. Oh don’t stop. Don’t you dare stop. I’m cccccccuuuuuuummmmmmmiiiiinnnnnnnngggggggg!!!”
I noticed Ann and Mom double teaming a well hung stud. Mom had his cock deep in her mouth. Ann had her pussy plastered across his mouth. The stud was mumbling something that I couldn’t make out. Ann had her head thrown back. She was mauling her breasts with both hands and sobbing, “Yesssssss, oh fuck yes, lick my clit, make me cum.
Ali directed me to the X shaped device in the far corner. She positioned me with my back to the device. “Raise both arms.”, she ordered me. I did and she buckled restraints around each wrist. Then she moved my feet and buckled each ankle in place. Finally, she tightened the foot wide strip around my waist. I couldn’t move, but despite my situation, I felt my cock begin to rise.
Ali pushed a couple of buttons and the device reoriented itself to about a 45-degree angle. The lower legs separated. I realized that my ass was now totally exposed.
Ali picked up a bottle off the shelf and poured some of the contents into her hand. Then she wrapped those long slender fingers around my cock. The liquid was warm and slippery. The feeling was intense and exquisite as she began to stroke my hardening cock. I strained against my restraints. Oh God, I wanted to cum. I closed my eyes and emersed myself in the pleasure.
Ali moved one hand to my balls. Then to the ridge that runs from my balls to my ass. As she pressed on that ridge, my cock expanded even more. I felt like it would burst. I can’t remember ever having this hard an erection before.
Ali suddenly removed both hands from my body. I opened my eyes to see what was happening next. She was holding small white plastic device. It was sort of shaped like the letter T. The long leg was about 6” and it was as big around as a small cock. The short side was shaped like a spring. Ali coated it with the lube. Then she stepped close between my legs. She rubbed more lotion over my anus and positioned the device at the entrance to my ass. As she pushed it inside, she began stroking my cock again.
I was in heaven. I had never felt anything like this in my ass before. I strained even harder against my restraints. I was thrashing my head from side to side. It was the only part of my body that I could move. When Ali realized that I was getting dangerously close to cumming, she suddenly stopped all of her actions. I could feel the cross piece of the anal probe pushing against that ridge behind my balls. It was making my cock pulse even harder. It was waving frantically in the air. “Not yet, lover. I won’t let you to cum just yet. I have the rest of our 15 minutes to torment you before I let you cum.
I don’t know how long this went on. Ali would tease me to the brink of an orgasm and then abruptly stop. I became lost in a fog of the pleasure Ali was administering. Then slowly, the pleasure turned to anguish. My wrists were being rubbed raw. The same thing was true of my ankles. My cock began to ache.
As the anal probe massaged my prostate, copious amounts of precum began leaking out of my cock. It was a strange feeling, this combination of pain and pleasure. Have you ever had an intense raging hard-on for almost 15 minutes? The stroking and the prostate massage was almost causing me to lose consciousness. Through this fog, I heard Mom’s voice, “Two Minutes. You only have two minutes left until number 3’s turn with Jack!”
I looked at Ali. She had this wild lustful look in her eyes. “Oh Ali, I need to cum so bad!”
“Oh please, please Ali, I really need to cum.”, I was almost sobbing as I begged for release.
“Call me Mistress Ali!”, she demanded
“Oh please Mistress Ali, please make me cum. I need to cum. I need to cum now! Please! Please! Oh fuck please make my cock shoot.” I was thrashing as hard against my restraints. It felt to me like my cock was a foot long. Every beat of my heart caused it pulse. It was red, sore, and very sensitive.
Ali again wrapped both hands around my cock. She began to stroke it faster and faster. “Cum for me now, Jack. I want to see how far you can shoot.” She continued to stroke my cock fast and hard with one hand. She took her other hand and began to saw the anal probe in and out of my ass. Every time she did that, It rubbed against my prostate.
I felt the cum start to flow from deep within my soul. Like a speeding train it raced through my balls and up the shaft of my cock. “Oh fuck, Mistress Ali, I’m going to cum. Please don’t stop. Make it shoot. Oh fuck, make it shoot!”
The first jet hit Ali right between her saggy tits. The second flew over her head. I was straining against the restraints with all of my strength. It felt so fucking good! Finally my body relaxed. I think I passed out. The next thing I felt was Ali pressing her body against mine. “Was that good, Jack? See I told you you would enjoy it, if you did what I told you to do…”
The next thing I remember was Mom’s voice asking, “Now who has number three?”
I was whipped. Alice had exhausted me by keeping my body on the edge of a climax for so long and then pushing me over that edge into the most intense cum I had ever experienced. All I wanted to do now was curl up in a ball and rest.
I opened my eyes and saw this big burly guy standing between my legs. “Hi!”, he growled. “I’m Donald. Today is your lucky day. I’m holding number three! You can call me Don.”
I felt my restraints being removed and my body being slung over Don’s hairy shoulder. As I took a good look, I could see that he was hairy all over his body.
He dropped me into a nearby sling. Through the fog that I was still in, I felt my wrists attached to a new set of restraints. My ankles were next. Finally, my waist was secured. I felt the sling tighten around my body as it lifted me off the floor. I was suspended in mid air in a spread eagle position. As Don stepped between my outstretched legs, I saw for the first time that he had a massive cock. It must have been 10” long and as big around as a beer can. He took some lube and applied it to my anus. It was cold and very slippery. His touch was excitinf as he pushed one then two fingers inside my body.
As he stepped forward, his monster cock swayed in the air. It had a large plum colored helmet. His cock had a definite curve upwards. Don had positioned the height of the sling so his cock head pointed directly at my ass hole. He moved closer, and I felt his cock at the entrance to my bowels. The pressure increased as he leaned into me.
“Oh no! It’s too big! It will never fit in there.”, I screamed out. I couldn’t do anything to avoid his onslaught. I had no leverage. As Don pushed harder and harder, I felt his cock forcing the sling farther to the side. Then suddenly, his cock slipped inside me and my weight caused my body to wrap itself totally around it. He was balls deep in my ass. The pain was intense. By now I was moaning that he was going to split me in two.
“Someone shut this baby up so I can enjoy fucking his tight ass.”, he barked.
I heard a familiar voice say, “I think I can help.” As I opened my eyes and tilted my head back, I saw a red bush shaped like an arrow pointing directly at a dripping wet pussy. It was Carol
“Hello Sugar.”, she whispered in my ear. “Time to help old Carol help you. Keep your head tilted just like that.” She took a step forward and guided her pussy right over my face. Of course everything, from my vantage point went black. “Now lick my pussy. Suck my clit. Make Carol cum!”, she hissed.
I loved the smell and the taste of her warm wet pussy. I was almost enough to make me forget the invader that was buried to the hilt in my ass. Another sharp thrust by Don refreshed my memory in a very painful way.
As my ass became accustomed to the massive cock, the pain began to diminish. It was replaced by the pleasurable sensation of Don’s cock massaging my prostate. Large amounts of pre-cum began to leak out of my still soft cock. Carol saw the flow and exclaimed, “I have to taste some of that love juice.”
She shifted her weight, without breaking the contact between her cunt and my mouth and climbed up on the sling. This rotated her pelvis so I could at least get some air. She had almost smothered me in her previous position. I began to lick her pussy in earnest. I slathered my tongue all around her clit. It got harder and bigger.
“Oh yes, sugar, that’s the way, make Carol cum.” With those words, she began to lick my soft cock like it was an ice cream cone. Then she locked her lips around the crown. I could feel her tongue licking up and down the shaft. My cock began to respond to all this stimulation. As my erection returned, I licked Carol even harder. Don was watching all this action as he relentlessly fucked my ass.
I’m not certain how long this went on. I don’t know if anyone was still monitoring the fifteen minute time limit. I think I drifted in and out of consciousness. I was exhausted.
I was jolted back to reality by Don’s bellowing, “Oh fuck yesssssssssssss! Here it cums. I’m going to shoot! Oh fuck, oh fuck, oh fuck, I’m ccccccccccuuuuuuuummmmmmmmmiiiiiiinnnnnnnggggggg!!!”
With that announcement Don made one more mighty thrust and reburied his cock balls deep in my ass. I could feel his cock spasms against my prostate as he filled my bowels with his seed.
That sensation was enough to make me cum too. When Carol felt the first jet of cum against the back of her throat, she pulled her mouth off my cock and let it spray all over her face.
I opened my mouth wide and licked as fast as I could. I wanted Carol to join in this cum fest. I was soon rewarded with her screams of pleasure.
“Oh Jack, that’s so fucking good. You are making me ccccccccuuuuuuuummmmmmm. Oh yes, oh fuck yes.”
We all three collapsed in a heap of spent flesh.
The next thing I remember, I woke up nestled in these warm loving arms. As I turned to see where I was I came face with a beautiful breast. “Welcome back to the land of the living, Jack” It was mom, she was holding me like her little baby. Ann was laying along side me.
Dad was spooned up against Ann. “You did us all proud, tonight.”
Mom was caressing my body all over. “You only need two more climaxes to set the record. We can help if you want to try.” Ann reached for my flaccid cock and began to pet it. I could see Dad caressing Ann’s breasts.