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Jessie’s Second Saturday Special

Category: Group Sex
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Just to bring you up to date, I am Jessie Bustamonte. A few weeks ago I was caught plagiarizing by my Professor. In exchange for his ‘overlooking’ my crime, I have been his sexual toy for the last month. My first experiences with the Professor have all been on Saturdays. The first Saturday I was tied up in his back yard with a cone fitted around my neck and all the male guests who were there ejaculated into that cone.

At the end of the afternoon, I was given to two of the men and they double-teamed me, one in my ass the other in my pussy. While they pummeled me all cum from the day was sloshing around in the cone and I was to try to drink most of it. However, I failed and although I later was forced to drink the remains of the cold slimy cum, I was promised a repeat Saturday in the Professor’s back yard.

In the interim, I was required to be at the Professor’s house every Saturday for his pleasure. On those Saturday’s I was used in whatever manner the Professor liked. I should note that both my Mom and Aunt were also under the Professor’s control and the three of us serviced the Professor every Saturday. I, being the latest captive was the focal point of these days with Mom and Aunt Suzie playing minor roles, mostly cleaning my cunt and ass with their tongues once the Professor had finished with me. I have experienced bondage, tit torture, having large plugs in my ass as well as learning to take the Professor’s 12-inch cock into my throat.

I am on my way to the adult store now, as I have each Thursday since this began, to pick up the clothes I will be required to wear this Saturday. I must admit that my pussy is dripping with anticipation and it is all I can do to not stop every fifteen minutes to masturbate. While I am not sure of what will be required of me on Saturday, I do know that I will be used, and used by lots of men all day long. Quite frankly I can’t wait to be the object of all those cocks in whatever way the Professor chooses.

This time as I enter the shop I go immediately to the dressing room and wait while the clerk brings me my outfit. She knows who I am and when I will be in so she is right behind me with the clothes. This week the Professor has selected another vinyl bustier, this one is open at the bottom, leaving my pussy and ass available and the top has a vinyl net for my tits. The bustier is white and with it are white lace stockings and white stilettos. I try it all on and as usual it is a perfect fit, but as I go to remove the clothing the clerk hands me a note. It says.

Miss Bustamonte,

You are to wear you outfit home today. You may not wear a coat or anything to cover yourself. You will be watched and the clerk will take your clothing and send it to my house. Once you are home you will continue to wear only this outfit and tomorrow at school you will only wear a summer dress to cover yourself leaving the outfit on at all times. On Saturday you will come to my house dressed once again in only this outfit.

Although a bit hesitant I leave the shop and walk the block or so to my car, I do not run as I know the Professor wants me to be exposed and in truth the feeling is remarkably exhilarating. When I reach my car I take my time unlocking the door before eventually sitting down and taking off for home. I use my left hand to finger myself as I drive home, the thoughts of being exposed on the city streets has me on the verge of orgasm. I finally cum in my driveway and sit in my car to enjoy the sensation that courses through me. When I do get out I look at my seat and see I have left a good deal of my pussy juices on the seat. I lean over and lick it all up, showing my ass to any neighbors who happen to looking. I then enter my house and say hello to my Mom.

“I assume Dad is away again?”

“Yes, Jessie. He’ll be gone for the weekend guest Pastoring at a church on the other side of the state. I see the Professor has started with you already this week. I like the outfit.”

“I do too. I am to wear this at all times, I can only cover it with a dress for classes tomorrow.”

“Well it looks good on you and I am sure that our company tonight will not object to seeing you this way.”

“Company? You’re having company tonight?”

Jessie was not only surprised she was concerned about how she was dressed. She wondered if the Professor knew all about this.

“Yes, your Aunt Suzie and her three sons will be here for the night. Your cousins Rob, John and Tom will be flying out tomorrow and it is more convenient for them to be here so they are closer to the airport tomorrow.”

“But Mom, the Professor requires me to stay dressed this way, my cousins will see me half naked!”

“Yes, I know. The Professor thought you could use a bit of extra play tonight so he has left you this way to excite your cousins.”

“Mom, isn’t it wrong to do this stuff with family?”

“Well Jessie, I don’t think it’s any worse then what you have done so far for the professor. In fact both your Aunt and I have faced similar experiences, so I imagine your ok.”

Good lord, Jessie thought, she was possibly going to be used by her three teenage cousins. Rob and John were 19 year-old twins and Tom was their 18 year-old brother. Jessie was having trouble accepting the fact that she would be their toy tonight and that both her Mom and her Aunt would be there too. While she realized that everything she had done so far for the Professor was pretty kinky and wild, this was a whole new world and one she was certainly unsure of. Her body however, was not as uncertain as her nipples were erect and rock hard and her cunt was already wet and dripping. When the doorbell rang and she heard the door open she wanted to run to her room and hide. She realized that if she did then she would only have to then walk back into the room as if on display when her Mom made her come out. So she stood there rooted to the spot as her Aunt walked in followed by her three cousins.

Rob, John and Tom gasped as they saw their cousin dressed in her white vinyl bustier and nothing else. They looked down as a group and saw her exposed pussy and then up top her tits loosely encased in a vinyl net. Her aroused nipples were pushing out through the gaps in the netting. Still rooted to the spot she did not hear her mother ask her to fetch refreshments. It wasn’t until she felt a deep pain in her ass that she realized her mother had used a cane to get her attention.

“Ouch. Sorry Mom. What did you say?”

“I asked you to go to the kitchen and bring out the refreshments I had prepared for our family. Now do as your told or I will let the boys use this cane on your ass.”

“Yes, Mom right away.”

As Jessie went to the kitchen she heard the boys giggling. She knew they were thinking of her and how she had just been caned and probably hoping that they would have the opportunity to do the same. She returned with the tray of drinks and snacks and offered it to everyone. As she bent over to offer the refreshments to the boys they each took the opportunity to grab her tits and squeeze them. She quickly realized that she was in no position to object and allowed them to paw at her.

Dinner was a similar nightmare for her and she was sure her tits would have been bruised if they had not started to grasp at her exposed pussy and left her sore tits alone. She was clearing the table when she heard her Aunt say.

“I have to thank you sis and I guess the Professor too. I have wanted an opportunity to have the boys learn how to use their cocks properly so they will be able to satisfy their girlfriends or wives some day. I am sure Jessie will enjoy it too, don’t you?”

“I know she will. She is a good little slut and she will find that as much as she may think she hates this you watch, she will be cuming and calling for more.”

“Well sis lets get the party started. Shall we just begin here on the table?”

“No, lets go to the living room, I want the twins to take her first, to double team her. Do you think they would mind?”

“No, they seem ready for anything. OK boys, strip naked and go to the living room. Your cousin Jessie will be in soon and you will all be allowed to use her.”

The boys went as instructed and Aunt Susie and Jessie’s mom escorted her into the living room.

“Ok nephews. Jessie is here for you to tonight. Rob, Lay down on the floor.”

Rob lay down and Jessie was instructed to sit on his cock and impale herself. Rob’s cock was nothing special, but it was a good six or so inches long and was wide enough to elicit a groan from Jessie as it slid into her wet pussy.

“Ok, Jessie now lean forward and let’s get John in your ass. Here John use a little of this lube on your cock.”

John lubed his cock then knelt down behind Jessie and put his cock on her asshole. He knew enough to push in slowly and allow her to accommodate him. Once he was in he and his brother began to saw in and out of her. John’s cock spread her ass nicely and Jessie was soon enjoying the two cocks invading her. When her mom had Tom put his cock to her mouth she quickly opened and worked her mouth and tongue on his hard member. His was the fattest of the cocks and it took her some time to work him in but eventually she took every inch of him shoving the tip of his cock into her throat. Jessie came twice before any of the boys did and when Tom filed her mouth with hot cum, she came again. Rob and John continued for a little longer before each emptied his load in her.

Jessie was spent and fortunately so were the guys. She was told to spend the night with the boys and she did. They managed to each find the strength to fuck her three more times through the night and by morning Jessie was well used. Both her ass and pussy were full of dried cum and her mouth maintained the lingering taste of cock. She had only an hour before she had to go to school and because she was not allowed to take her outfit off, her mother had to take her into the back yard and use the garden hose to clean her pussy and ass of the built up cum. It was cold water but Jessie withstood the iciness and after slipping on her white sundress was driving to school feeling spent from the night.

Jessie did not have a class with the Professor on Friday but she was handed a note asking her to report to his office at 4PM. She felt her cunt start to tingle at the thought of a private meeting with the Professor on campus and anxiously waited for the time to arrive. At exactly 4PM she knocked on the Professor’s door and when she heard him ask her in she opened the door and walked in. She was surprised to see another girl in the Professor’s office. The girl was taller then Jessie but she was thin with hardly any bust line at all and although her facial features and long black hair made her beautiful. She looked lost sitting here.

“Miss Bustamonte, I asked you here to meet with Miss Wilson. Miss Wilson was caught cheating on her mid terms today and she is very apologetic and begs me to give her another chance. Since you also have been caught and given another chance I want you to take Miss Wilson and prepare her for tomorrow. She has agreed to come. You will take her downtown and have her dressed then spend the night with her and bring her with you tomorrow. Is that clear Miss Bustamonte?”

“Yes, Professor. I will do as you ask.”

Jessie looked at the girl and part of her was angry. She was looking forward to her day tomorrow and did not want to share it with anyone. Now it looked as if this skinny bitch would also be there. She looked her over again and said to herself ‘that bitch will not last long enough to ruin my day’ and then she took her by the hand and led her out of the Professor’s office.

“My name is Jessie. What’s yours?’

“My name is Angelica but everyone calls me Angie.”

“So, Angie. Are you aware of what you have agreed to do for the Professor?”

“I said anything and I will do anything. I was stupid and lazy to try to cheat and if I can earn this second chance I will never be so foolish again. Besides he said I would be serving at a party at his house tomorrow how bad can that be?”

“You do realize, Angie, that you are what will be served tomorrow don’t you?’

“What do you mean?”

“I mean you will be what is offered to the guests tomorrow. We are on our way to an adult clothing shop to pick up your outfit for tomorrow. See this is what I will be wearing.”

Jessie pulled her dress up to show Angie her white bustier and stockings. Angie looked to be shocked to see what Jessie was wearing and froze in the hallway.

“You don’t mean that I am going to be a sexual offering to his guests?”

“Exactly, you will be used by any and every male and female in attendance.”

“But…. I mean…that isn’t what I thought he meant… I am not used to being sexually active…. I mean I have had sex but not a lot. What…I mean how will…”

“All I can say is that I was used that first Saturday as a target for all the guys. They tied me to an area out back and placed a cone around my neck and all day long guys would come and beat off and ejaculate into the cone. By the end of the day there was so much cum in the cone and I had to drink all of it. That was after being fucked in the pussy and ass at the same time.”

“Oh my. Oh shit. I have never had anal sex and I hate the taste of cum. What have I gotten myself into? There must be another way.”

The girls fell into silence as they got in Jessie’s car and made it downtown to the shop. Once in the shop they went up to the woman clerk who always had helped Jessie and asked if there was an outfit ready for Angie. The woman clerk said yes, but that John the guy behind the register was supposed to help this time. She went and traded spots with John and then came to the girls.

“Which of you is Angelica?”

Angie raised her hands and John pointed towards the dressing room and she followed him. Jessie tagged along. John handed Angie her outfit and then the three of them stood in the changing room waiting for Angie to act. Finally Jessie said.

“Angie you need to try to the outfit on with John here watching. He has to make sure of the fit and it is required.”

Angie slowly stripped her clothes off. Jessie was amazed at how pretty she looked naked. While she had tiny tits her ass was full and firm. Jessie was a little turned on by her and as she put on her outfit, which was the same as Jessie’s only in black she felt a familiar tingle between her legs. When John approved of the fit and then took her clothes Jessie told Angie how she was forced to leave the shop on Thursday. Jessie took off her dress and then the two of them left the shop and walked openly through the streets to Jessie’s car.

As they drove to Jessie’s house the two girls talked some more about the Professor. When Jessie told Angie about the size of his cock and having to learn to take it all, Angie looked ready to cry. She said.

“I am not good at sucking cock and I know I wouldn’t get much of him in my mouth, and my ass is so small. I am scared he will hurt me bad.”

“Well the butt plug was the second time not the first so don’t get all worked up about it. Besides I have no idea what he does with anyone else only what he did with me.”

“Yeah, I guess but the thought of that big of a cock in my pussy is frightening too.”

“I can assure you that by the time he is cuming you will not want him to pull out. You will love the feeling of that big fat cock squeezing in you. God I get wet just thinking about it.”

The girls talked on and eventually made it home. Jessie’s Mom was expecting Angie and had dinner for the two girls when they came in. After dinner the two girls were told by Jessie’s Mom to go to Jessie’s room and wait for her. They went up and sat on the edge of the bed and continued to chat while waiting. A little later Jessie’s Mom came in with a strap on cock. The cock was black and large.

“Jessie you are to put this on and to work both of Angie’s holes so she will be ready for the party tomorrow. Now I am supposed to watch you two but I am busy with my own preparation for tomorrow so can I trust you Jessie to do what you are supposed to do?’

“Yes, Mom.”

As her mother left Jessie took the strap on and put it on. She adjusted the fit so it felt good and then she said to Angie.

“Well start by sucking this cock bitch and do it now!”

She pushed her fake cock towards Angie’s mouth and after some hesitation Angie opened her mouth and tried to take the cock in. It was obvious that She was not getting anywhere and so Jessie ordered her to lie down on her back. Jessie climbed on top of her and used her hands to play with Angie’s pussy. It was surprisingly wet so she put the cock in position and pushed it up against the opening of Angie’s cunt.

“Ok Angie here goes.”

As Jessie pushed herself in Angie cried out.

“God, Jessie that hurts. Oh shit! Please stop.”

But Jessie knew she had to push on. Angie started to squirm as Jessie pushed inch after inch into her cunt. She had only gotten about half of the cock into her when Angie wrapped her legs around Jessie’s waist and said.

“Please no more. I don’t think I can take anymore please stop.”

Jessie ignored her and rammed in the remaining four or five inches causing Angie to scream out loud, an ear piercing noise that rattled Jessie and brought her mom into the room.

“What is going on in here? Angie you need to grow up girl. Your pussy is made to stretch and you will stop being such a spoiled little girl. Now Jessie roll her over so I can warm her ass with this cane. Perhaps that will teach her a lesson about real pain.”

Jessie rolled over and now Angie was on top. This position allowed gravity to force Angie’s cunt down onto Jessie’s cock and firmly fix it in her cunt. Then Jessie’s mom began to strike Angie’s ass with the cane. With each strike of the cane, Angie who was trying to get off the cock buried in her would slide back down again to get away from the sting of the cane. Jessie just lay there and watched as Angie would struggle to get up and off and then the cane would lay into her ass and she would slide aback down. She was managing to fuck herself. Jessie could hear the change in the tone of her screams as each lash of the cane struck her. She was no longer fighting it, her cunt was dripping juice all over Jessie and from the way her legs were shaking she knew that Angie was soon going to have a major orgasm. When her mom had finished with the cane, Angie continued to ride the cock. She was obviously enjoying it now and so Jessie’s Mom left.

Jessie started to push up as Angie pushed down and together they managed to bring Angie off in glorious fashion. Jessie wasn’t sure if she was louder when they started or when they finished but she knew that Angie was not a quiet fuck. She was a very loud expressive fuck and she liked that.

Jessie decided that she would take Angie’s ass right away. She felt that with her in this blissful state having just cum, with her ass well caned and red, it was the perfect time to force this monster cock into her virgin ass. She rolled over and told Angie to get on her hands and knees. Angie was too far gone to ask any questions and did as she was told. When she felt the tip of the plastic cock at her asshole she tensed up and said.

“OH noooo. Please not my ass!”

Jessie rammed the cock in all the way in one push then held it there. Angie was dead quiet for some time before emitting a low moan that gained volume and depth as the seconds passed finally culminating in an animalistic roar. The noise abated but did not stop so Jessie slid back out and then rammed it in again. Once more Angie slowly came to a loud roar and quieted and then Jessie began moving in and out without pause and Angie began to grunt and groan loudly with each thrust. She was accepting the cock in her ass better then Jessie had expected and so when Angie started to move with her and to emit soft yesses amid the other noises Jessie allowed herself to enjoy the pressure the dildo was giving on her own cunt.

“Cum for me bitch”

Screamed Jessie as her passion took over.

“Cum all over my hand.”

Jessie put her hand between Angie’s legs and shoved two fingers into her wet hot cunt.

“Cum now bitch. Cum on my hand.”

“Shit yes, I’m cuming. OH God Yes.”

Angie came all over Jessie’s hand saturating it completely. As they both enjoyed their orgasm and fell to the side with Jessie’s arms still wrapped about Angie’s body the two slept with the cock still buried in Angie’s ass.

Jessie did not sleep long and was soon awake to find her hands playing with the childlike tits that Angie sported. She was enjoying Angie’s nipples, how hard and firm they remained when Angie woke and said.

“Jessie that cock in my ass is starting to hurt again. Please take it out?”

Jessie slid the cock back and forth in Angie’s ass a few more times before pulling it out completely. She looked down at the plastic cock and saw that it was covered in Angie’s body fluids. She told Angie to get on her knees on the floor and she then stood in front of her.

“Angie you need to learn to suck cock. Open your slut mouth now or I will have Mom come in and cane that well fucked ass of yours.”

“But, Jessie it’s so dirty. I can’t take that in my mouth, it’s been you know!”

“Yes, Angie I know where it’s been and I know where it is going now open and open wide bitch!”

Angie hesitated for just a moment before slowly parting her lips. Jessie did not wait and she rammed the phallus into Angie’s mouth hard bumping up against the back of her throat causing her to gag and pull her head back away from the cock. She was bent over trying to stop gagging when Jessie grabbed her hair and pulled her head back up and shoved the cock back in, this time going even further into her throat.


Jessie smile as she listened to Angie’s garbled sounds as she forced the cock all the way down her throat. She would pull it back a bit then push it as far forward as she could finding herself getting off on the sounds of Angie gagging.

“gggggggllllllleeeee ggggggggg”

Soon Jessie felt her own orgasm peaking and she stopped fucking Angie’s face. As she fell onto the bed allowing her body to spasm and jerk through her massive orgasm she still heard Angie trying to catch her breath and empty her mouth of the saliva that had built up during the act.

“Angie, I think you are better prepared to face tomorrow now. You must realize that the cocks that will use you tomorrow will all be almost as large as this plastic one and a lot of them will be larger. So sleep now and rest up for tomorrow.”

The next morning both Angie and Jessie went to the Professor’s house and were kept waiting for ten minutes on his front porch in their bustier and heels. Their asses and pussies on display to all the passing neighbors. Every now and again a passing car would honk the horn and some young guy would yell out the window something obscene. Jessie was enjoying it, having gone through this a few times but Angie cringed each time and she was desperate for the door to open.

When it did a man stepped out and closed the door. He said.

“You two are to go around to the back yard. You can go that way. The Professor sees no reason for you two whores to be in his house yet.”

So Jessie led Angie around to the back yard. When they passed through the gate they saw what looked like a hundred or more young black men. By their dress some were from the college but a lot of them looked like gang types from the city and some looked like older homeless tramps. A man Jessie recognized came up to the girls and directed them to a spot in the yard where two areas had been set up, one for each of the girls.

Each area had a sex swing hanging. In this swing the girls would be restrained but their mouths, asses and pussies would be readily available to anyone who wanted them. As they were secured in their own swings Jessie noticed what looked like a child’s swimming pool directly under each of them. While She was sure why they were there she still listened to the man who was in charge.

“Each of you girls will be used for today’s entertainment. The men who attend here today will use you in whatever way they want. The pools beneath each of you are to collect all cum, piss and whatever drops from the two of you through the course of the day. At the end of the day you will both be required to clean your pools with your tongues and the first one done will be our winner. The loser will be at the mercy of the winner for the next week. I would ask you if you had questions but it really doesn’t matter because you’re just meat.”

Once he finished and left the men started to move towards the girls. Jessie felt a cock entering her ass very quickly and saw another headed towards her mouth. She opened her mouth and greedily took the cock in allowing it all the way into her throat. She felt the other cock filling her ass and enjoyed the action as the two cocks going in and out of her. She did manage to glance over at Angie and could tell she had two men at her also.

It was a long day and made longer by the screams Angie made as she orgasmed. The girl was a loud fuck. Jessie took cocks all day in all of her holes and was periodically the target for a pissing contest as well. Often men would piss in her pussy and ass washing out the accumulated cum and filling her pool with a slimy stinking collection of fluid. At least she was able to swallow cum ejaculated into her mouth most of the time but even some of that found its way to the pool. During a lull in the action she was able to watch as Angie was fucked by two men at once. By the sounds she made one was in her ass and the other in her mouth. Jessie enjoyed watching the action and noticed that Angie’s pool seemed to be much fuller then hers and wondered if she had had more action or if someone had been fudging the “contest”.

The girls had been given food and drink through the day and there were periods where they were allowed to rest. Regardless by the end of the day both had been used like a urinal at a packed sporting event. Their pussies gaped open and their asses were stretched wide. Cum had no chance of staying in either hole and few of the cocks felt much friction when they fucked either girl.

The end was signaled by the appearance of the Professor. He waddled out to the area and looked at both girls before ordering us released and placed in our own pools. As the girls were forced to kneel in their pools the Professor repeated that they had to clean up the area by licking the pools. The winner would control the loser for the week before they were both due back to the Professor’s house for private training the next Saturday. As one final handicap the professor brought two gruff and rough men forward. He explained that the two men were stonemasons and showed us their very large and callused hands. The Professor then explained that each of the girls would have a fist in their ass while they cleaned their pools.

Angie looked at the hands coming her way and scuffled to get away. It was of no use as she was kept in place by many hands. Jessie on the other hand smiled and held her ass cheeks apart for her man. As he worked his hand in her ass finger by finger Jessie drooled and smiled. Once his hand was completely in her ass she dove into her slime and began to drink and suck up the cold stale piss and cum. As she moved the man moved behind her keeping his hand buried.

All Jessie could hear from the other pool was loud screams as Angie protested the invasion of her ass. Jessie was almost finished with her pool she was now just licking up the remnants and was declared the winner. She looked at the Professor and said.

“I am a complete slut Professor but can I help Angie finish her cum? I love it and would love some more! And Professor can this guy behind me put his other hand in my pussy?”

The Professor nodded and Jessie braced for the second hand to invade her pussy. She allowed the force of the second hand to push her into Angie’s pool and she buried her head in cum and piss as her body accommodated the two large hands. Soon both pools were emptied and the two girls had their asses emptied and were brought to stand in front of the Professor.

“Jessie you are by far a total slut. I hope you enjoy this skinny bitch and use her well this week. I expect that after a week in your control she will do much better then she did today. And Angie your tits are useless. After you complete your service to Jessie I am sending you to a surgeon who will make you some tits I can be proud of. Now both of you see if anyone wants to fuck or be sucked till the last guest leaves then you are free to take off.”

Jessie and Angie circulated the grounds and took care of anyone who had a need. By the time the last guest left they were both covered in cum. As they walked to Jessie’s car in the driveway Jessie said.

“Angie you need to lick me clean before we go anywhere and then when we get home I am going to borrow Mom’s cane and begin teaching you how to be a better slut.”

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