Jessica Ann Pledges a Sorority

Story Info
Young college girl is used.
5.9k words
3.9
216.2k
64
5
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Jessica Ann had been in college for only three months when she was asked to pledge a sorority. She was amazed that anyone on this huge campus even knew who she was. She was a small town Midwestern girl who had first seen a major city the day she arrived on campus. She had begged and pleaded with her parents to allow her to come all this way for her education. Jessica Ann was a good student, obtained top grades all through school and had sensible ambitions for her future. All of this made her parents decision to allow her to go to San Diego for college a lot easier.

Jessica Ann was doing well in her classes she studied most of the time, but always had some time for her roommate Anna and her friends on their dorm floor. So while she was not a complete shut in or recluse, she was not the life of the party either. In fact her roommate Anna and their friends in the dorm were all pretty serious students. The fact that most of them were fairly ordinary girls made such a life normal, but Jessica Ann was as pretty as any girl on campus, that is if she wanted to be. She always dressed in baggy clothing that would hide her firm ass and make her 34 DD breasts look like tiny B cuppers. Her hair was never styled and she wore glasses and a floppy knit hat everywhere she went. She dressed like a nerd and only those who saw her in the shower were aware of the pure beauty of the girl.

That is why she wondered why any sorority would want her enough to invite her to pledge. She knew the sorority in question was not the "hot" one on campus in fact this one was quiet and full of ordinary girls. When she had visited the sororities during rush week, she liked the quiet studious atmosphere of the house and most of the girls were truly nice to her. Although she had participated in rush, she did so to see what it was all about she was not really looking to join one of them. However, being invited was an honor and she would listen to what they had to say.

The night of the sorority's invitation to join party Jessica Ann arrived dressed as she always was, neat and presentable but in no way did she nor would she dress to advertise herself. She was welcomed to the house and after a tour and some history of the sorority her and the other invitees were ushered into the house's dining room where over soft drinks the rules for admittance were reviewed. As long as you completed your tasks within the week you were generally assured of being sworn in to the sorority. When asked about the tasks to be performed they were told the exact tasks would vary, they had drawn up enough task lists to accommodate all of the invites should they all want to join. All of the lists were put into a fishbowl and as each pledge declared her intention to join she would receive a list and her week would begin.

One girl immediately asked to be allowed to join and she was taken to the fishbowl and allowed to select a list. She was sworn to secrecy and told not to share her list with the other potential pledges. Jessica Ann liked what she had seen and heard and decided to join as well. She asked and was allowed to select a list and left to begin working on it. There were twenty tasks on her list and a brief scan told her that most of this would be doable in the week. A few of the tasks would require the cooperation of others and might take some time and as she looked at the last task she froze. Her last task required her to enter an adult sex shop and purchase two items; She did not need to use those items but merely go in make a purchase and leave. She was concerned about this task because she had never in her life been in to that kind of shop. She had never looked at that stuff on the Internet either. She would be embarrassed if someone saw her in there and doubly embarrassed to actually buy two things.

Now Jessica Ann was not a virgin, no she had had sex, she believed. She had met a guy this past summer and decided she was not going to be the only girl in college who had not had sex. Besides if she ever met a guy she did not want to have to tell him she was a virgin. So she and Blake had had sex three times this past summer. The first was terrible as everyone says, it hurt and Blake was a quick to cum. A couple of weeks later they tried again and while there was no pain she wondered what she was missing because it did nothing for her. Assuming it had been her she and Blake tried again with no better result. Jessica Ann ended up with a pussy full of sticky cum and not much more. She might have tried again but she and Blake broke up and soon she had to leave for college.

Once she returned to her room she planned her moves to accomplish everything on the list. Jessica Ann always had a plan and her plans always worked. She decided she would save the hard one for last and that she would go observe an adult shop and see when the slowest time was. She figured she could go when almost no one was there then she could just grab two things and get out. Over the next couple of days she managed to take care of the nineteen easier tasks on the list. She had also determined that mid morning was the best time to go to the adult sex shop.

The next day she had no morning classes so dressed in her normal garb Jessica Ann made it downtown and walked to the adult shop. Her nerves had gotten to her and she hesitated for a bit. Eventually she knew she would have to just do it, so she walked right in. She was certainly amazed at all the different items in the shop, so amazed that she just stood for a moment to take it all in. When she heard the clerk clear his throat she snapped out of it and went to pick up her two items. Jessica Ann had been taught since she was old enough to listen that the women in her family always looked for sales. Close outs, discontinued merchandise, irregulars what ever they could buy at below cost. Her natural habits kicked in and her first item was a large rubber all black item that looked like a man's penis. It was cheap and she wasn't getting it for herself anyway. She next went to a wall of videos but before she could select one she noticed out of the corner of her eye a boy he knew from school. She quickly dropped down behind the racks and hid.

Not only did she recognize Scott, he would know who she was too. She stayed hidden while Scott went into a back room. She took that opportunity to grab a DVD and with her huge black cock she went to the counter and quickly paid and left. She never noticed that she had bought a two pack of fetish videos. But after she left Scott went to the counter and asked his buddy Jim what Jessica Ann had bought. Jim told Scott that she had gotten the biggest black dildo they had ever carried; in fact they had to put it on sale because no one wanted a dildo they could not use. He told Scott she had also bought the twin DVD pack containing a DVD on White women taking multiple black cocks in her ass at the same time and the second one was about white women who loved to be gang banged by black men.

Scott was in some ways shocked about Jessica Ann's taste in sex but then again he had seen so much working part time in the adult store that nothing really shocked him. He decided that her was going to help Jessica Ann realize her fantasy. He looked forward to seeing her being taken by a bunch of black men. And he knew where to get enough guys to satisfy her desire for a gangbang too. There was an all black college just a few miles out of the city and that area would be good place to set this whole thing up. It was a fraternity house just off that campus situated in a wooded area. Now he just needed to make sure the guys were in and figure out how to get Jessica Ann our there and keep in a surprise.

The guys were interested in Scott's idea but insisted that they make sure the girl was too. They did not need any police problems about a fraternity of Black men raping a little white girl. Scott assured them that this was her fantasy. He told that that he often saw her fondling a huge black dildo and knew she watched DVD's of black men gangbanging petite white women. Scott also lied about how he knew all of this saying he too had fucked Jessica Ann and she always wanted to discuss her fantasy. Scott also told the guys that it had to look like a Jessica was being raped, as that was all part of the fantasy. To assure them he promised that Jessica Ann would bring them a letter she would sign stating all of this and hand it to one of the guys when she arrived. She figured the guys would see what she desired and then did not want to speak of it any further she just wanted to get into the role of victim.

The Fraternity as a group thought about this and in the end agreed to be Jessica Ann's fantasy, provided she did in fact hand them a signed letter begging them for it. Scott was thrilled and now he just needed to get Jessica Ann out to the fraternity house. It was agreed that Scott would set all of this up for this coming Friday night and that Jessica Ann could be used again and again all weekend. There were a lot of big smiles in the group as Scott left to put the second half of his plan together.

Scott found one of Jessica Ann's notebooks and had a few pages of her handwriting copied before her returned the book to her room. He the studied her handwriting and was pleased to find she basically printed everything and he soon was able to make a reasonable copy of her writing. He then wrote out, on very feminine stationary her had bought the following.

"I know that my fantasy is a bit unusual but I have thought of this scene ever since I first had sex and started reading and watching porn. I want to be taken by everyone in this fraternity and used completely. I will protest and beg to be let go, but I really want all of you to make me perform with each and everyone of you and I hope you guys will also double and triple team me as well. I love having my ass fucked and if you can manage to get two of your beautiful black cocks in my ass at the same time it would make my fantasy complete. Just remember I will protest and beg to be let go all the time I am there but I really want to stay the whole weekend and when I leave I want to covered inside and out with cum. No showering at all before I leave. I can't tell you how much I appreciate you guys agreeing to do this for a plain Jane Midwestern girl."

Scott signed it in Jessica Ann's hand and sealed it in an envelope. On the envelope he wrote the Fraternities name. Now he would need to get her to go out there to deliver the letter and let nature take its course. Scott intended to film the whole thing and had already gotten the equipment he needed for that from Jim at the store. The frat guys were ok with the filming too. So Scott told another girl, who was in the sorority Jessica Ann was pledging and who had a crush on Scott all about his plan and asked her to give Jessica Ann the envelope and tell her it was her last pledge chore to deliver it to the fraternity. Scott knew Jessica Ann would need a ride and he told his friend to suggest to Jessica that I would be happy to take her on the errand in my car. The girl. Betsy insisted she be allowed to go and watch the action. Betsy was a 5'2" Bleached blonde California Surfer girl with a nice body topped off with pair firm 36 C tits.

With his plan set Scott Betsy and Jim went to the Frat house early Friday and set up a number of cameras. They covered the main hall where most of the action would take place and they also prepared one of the spare bedrooms where some individual action could occur. It took them most of the day but they were looking forward to filming this gangbang and had thoughts of maybe marketing the DVD or at least putting it on the Internet. Scott and Betsy returned to campus and Betsy delivered the envelope and told her she had to deliver it that night to the fraternity. A little later Scott managed to accidentally walk by Jessica Ann's dorm room. He saw her sitting on her bed and holding the envelope. He said Hi and continued down the hall. He had not gotten more then a few steps before Jessica Ann called after him.

"Scott, I have to deliver this letter to a fraternity at that College just out of town as a chore for the sorority and I need to ask if you could drive me out there. I'll pay you for the gas and it should not take too long. Would you help me?"

"Sure no problem when do you need to go?"

"I am supposed to deliver this to the Frat house before 8 PM so we should leave no later then 7:30. Is that ok with you?'

"Tell you what. I have a date with Betsy tonight and we were going to a bar/restaurant on the way. I know Betsy won't mind you coming along. If we leave now we can stop and have some dinner on the way. My treat and no I won't let you pay for the gas. Deal?"

"Sure Scott that's very nice, are you sure your girlfriend won't mind?

"No she told me she'd given you the letter and actually asked me to see if you needed a ride, I confess it's really her idea to take you. So are you coming?"

Ok, just let me get my hat and I'll be ready."

Scott was thrilled that all was going according to plan and that he and Betsy would get to spend some time with her too. His hands shook he was so excited, in a couple of hours he would get to see Jessica Ann naked and being used by 30 or 40 black men for two and an half days. He Betsy and Jim would get some great video of all of this. He was so wrapped up in his thoughts that he did not hear Jessica Ann tell him she was ready. He felt her lightly punch his arm and then heard her say.

"Scott, earth to Scott are you there?"

"Gee, sorry I was just thinking how much I was going to enjoy our little trip. I hope you don't mind eating with Betsy and I."

"Scott, I am grateful for your help and you always seemed like a nice guy and I've met Betsy and she seems to be nice so dinner is no problem, I mean we all have to eat right?"

Scott laughed and nodded and they were off to pick up Betsy.

Once all three were on there way they talked about typical college stuff, Betsy and Jessica Anne discussed the things they typically did on a Friday night and Betsy asked her if she wanted to hang with her and Scott later after she'd delivered the letter. Jessica Anne told her she was thrilled to be asked but felt like a third wheel and usually wasn't real comfortable in party like situations. Betsy continued to beg her through dinner and finally on the way to the frat Jessica Anne agreed.

Scott and Betsy relished their ability to make their involvement in everything hidden this invitation to join them after would certainly keep Jessica Anne from guessing any involvement by them later. They would tell her if she asked that a guy from the frat came out and told them that Jessica Anne was to stay for a while to get a return letter and someone from the frat would bring her home. That would keep Scott and Betsy's involvement in this whole thing a secret.

When they dropped Jessica Anne off they waited for her to go in the frat house then they parked and went in the side door and met Jim. Then they all took their places a camera and waited for the action to come. Scott actually would control the camera in the office where Jessica would start the weekend and then move to one of the other sites. In fact if everything went according to plan they would all rotate from one camera to the next to capture all that went on in various places in the frat house.

Scott watched as Jessica Anne delivered the letter to John, the president of the frat in his office. Scott also listens to their conversation through the microphones that were recording the audio for the film.

"Hi, I'm Jessica Anne and I was told to bring this letter to you tonight. I was told you had to have this tonight before the weekend started."

"Thank you Jessica Anne, my name is John, please have a seat while I read the contents."

Scott watched as John read the letter Scott had written. Then listened to John say.

"Jessica Anne you voluntarily brought this letter to me correct?"

"Yes, sir I wanted to do this."

Jessica Anne felt it best to not tell him she was required by her sorority because she thought it would be better it came over as her choice.

"Ok then lets get started, Bill, Levon, prepare her."

Two large black men come in and grabbed Jessica by the shoulders and took her baggy pants and panties off leaving her naked from the waist down while John freed his cock from his pants. While Bill and Levon held her John moved closer to her and put his legs between hers and pushed her legs to the side.

"What are you doing? Hey put my pants back on, my god what are you doing you just can't do this to a girl, its rape. OWWWWWWWWWWWWWW"

John had pushed his cock into Jessica Anne's pussy. It was a tight fit, he had a fairly fat cock and he had to push hard to get all the way in. Jessica Anne continued to scream and fight John as he let his cock linger inside her. He nodded to the two guys and they lifted her baggy shirt over her head then took her bra off.

"My god look at those tits. Shit girl why have you hidden them, they are magnificent."

As John said those words he pulled his cock out and shoved it back in while using his hand to grab and pull on one of her tits.

"Owwww , pleeeassseee don'tttt ddooooo thisss toooome, oohhhhh noooooooooo."

John ignored Jessica Ann's pleas as the letter had told him to and fucked her. He pumped his fat black cock in her again and again while Jessica continued to beg and plead to be let go. When John felt his cum boiling to the surface he pulled out and sprayed his cum all over her belly and tits. He then took Bills place and Bill pulled his cock out and jammed it into Jessica Ann's now wet cunt.

"OHHhhhhh n plesseeeee nnooooooo moreeeee Pleaseeeeeeeeeeeee of godddddddddddddddd ohhhhhhhh nnnoooooo"

Bill used his much longer cock to ream Jessica Ann's pussy as he fucked her. His strokes were even and deep and as he bottomed out in her she would yelp then continue to beg to be let go. Bill decided to fill her cunt with his cum and allowed his cock to erupt deep inside her. When Levon shoved his cock into her she was as wet as she could be and even though she continued to protest her body was now reacting to the pummeling of the cocks. Her breathing was ragged and her legs were quivering and even her pleas for release had a staccato sound to them reflecting the internal eruption of her coming orgasm. Levon lasted a good while and he felt her cum a second time and when she did her pussy muscles began to contract on his cock forcing him to erupt in her now well-fucked pussy.

Next John had Jessica Ann on her knees and he brought his cock to her mouth, when she saw what he was trying to do she started talking.

"No way I am putting that thing in my mouth, I just don't do that, it's a dirty filthy thing and it was just inside me. No way I ummmmmgggggggghhhhhhrrrrrrrrrrrr"

John was tried of listening to her and shoved his cock onto her mouth. No one really knows what more she said because it was all garbled. John pushed all the way in and down Jessica Ann's throat causing her to gag. When she looked to be out of breath John slid his cock out and she gagged up a mouthful of saliva. John waited a second for Jessica Ann to catch her breath and in that second she began.

"Don't do that again you went in too far and it hurt me I was having trouble gggggguuuuuugggglllllleesssssrrrrrrrrrssss"

Once again John refused to put up with her complaints and shoved his cock back inside. Now all you heard was that hollow thunk as his cock met the tight opening of her throat. Every now and again John would push his cock as far as he could into her throat. He loved to watch her head jerk as she gasped for air. He was having such a good time that he suddenly came in her mouth. Jessica was sputtering and trying to spit cum out when, John pulled out and, closed her mouth with his hands. He then pinched her nose and forced her to swallow the remainder of his seed.

12