Olivia’s Ordeal By DirtyMartini

So many things were going through Olivia’s young mind as she rode in the back of the van. Though she was uncomfortable from the cuffs and leg irons digging into her lovely olive skin, this was barely a distraction as she replayed the recent events of her life over and over in her head. It was dark in the back of the transport van, and the 20-minute ride gave her plenty of time to think. How could she have not known her boyfriend Kenny was dealing drugs? He seemed like a nice guy and always bought her nice things. How could he have set her up to take the fall? He had told her he loved her and they would always be together. What was life going to be like in her new home? She heard so many stories. Were all those dykey girls going to be staring at her pretty young body? God, the thought of it made her cringe…

She can still hear the judge’s words, “90 days in the woman’s unit at the county jail”. She can still hear her lawyer telling her what a great plea bargain deal he got her. Great deal for whom, she thought, him? He gets paid and gets to go home to his wife. I’m the one going to jail.

After what seemed like an eternity, the van finally arrived at the main prison entrance. The driver said something into the radio and Olivia could hear the main gate squeal loudly as it slowly rolled open. Once inside the walls the van slowly drove down the long road to the intake building. As it rolled past the streetlights, each shone its light beam in through the small window on the side of the van, lighting up Olivia’s blank expression with a slow motion strobe effect.

After a few minutes the van stopped at the loading dock. A few more minutes and Olivia could hear voices on the other side of the van door. The door opened quickly and Olivia could see two female guards.

“Step out of the van please.”

Olivia got up and slowly walked to the back of the van, the chains from the leg irons clanging in rhythm with every step she took.

“Watch your step.”

The two armed officers slowly escorted Olivia past the loading dock to a door. When they arrived at the door, one of the officers spoke into the intercom.

“One prisoner from central holding.”

A loud buzzing sound signaled the unlocking of the door and Olivia was led in. She was escorted to a small, hard, wooden bench and told to sit. One of the guards took out a key and released the handcuffs from one of her wrists. She then took the freed cuff and locked Olivia to a large metal hook on the bench. Next, she bent down and released the leg irons from both ankles and tossed them in a heap against the wall. The guard then went over to a desk where a large female officer sat and handed her an envelope containing Olivia’s jewelry and personal property. After a few moments of small talk, the two guards that brought Olivia in left. As they passed by Olivia one of them spoke, “Someone will be with you in a few minutes.” Then they walked back out the door.

Gee, someone will be with me in a few minutes, Olivia muttered to herself. Well, they can take their sweet time. I’m in no hurry. She looked over at the officer sitting at the desk. She was a large, black woman about 30. She did not look up and did not seem in any hurry. At no time did she even acknowledge Olivia’s presence.

Olivia looked around the jail. It was cold sitting on the bench. Olivia had goose bumps and the small hairs on the back of her neck were standing up. She was not shivering, but she was cold.

The gray painted cinder block walls did nothing to give the place a feeling of warmth. There were girls’ names etched into the walls everywhere. In some cases a heart would surround two girls’ names. Olivia stared at the wall where ‘Lisa loves Pam’ was prominently etched in bold letters and let out a small chuckle. ‘That could never be me,’ she thought.

After a half-hour or so, the large black officer finally got up. She walked over to Olivia and stood directly in front of her. She was a large, imposing figure with a look of authority. She held some papers in her hand, which she kept looking at. After a moment she asked, “Your name?”

“Olivia Diaz” was the reply.

“Your age?”


“Social security number?”

“178-88-4953” was Olivia’s quiet reply.

The officer then pulled out a key and unlocked Olivia’s handcuffs. “Follow me” she said.

Olivia followed the officer to a small room down the hall that contained a desk with a computer and not much else. The officer reached into a closet and pulled out a plastic storage bin. She then removed a paper form from the top desk drawer and began filling it out. As she did she handed the plastic bin to Olivia.

“Remove all your clothing and place it in the bin, including your underwear. I see you have a shirt, pants, bra, panties, two socks and a pair of sneakers. I also need you to sign this property receipt.”

“Can’t I keep my underwear?” asked Olivia.

“No. You can’t have anything you can hide things in.”

As soon as she handed Olivia the property receipt, the officer reached in the bottom drawer and removed a pair of latex gloves from a large box. She put the gloves on.

“I need you to turn around and face the wall.”

As Olivia turned and faced the wall, she could feel the officer’s fingers probing her ears, bending each one back slowly. She then lifted up Olivia’s long black hair and ran her fingers slowly through it in a deliberate methodical kind of way.

“You have anything on your person you should not have?”

“No,” said Olivia; “I was searched just before I entered the court house.”

“I have to do it again. Procedure, you know.”

Olivia could feel that the officer let go of her hair as it fell back onto her neck and shoulders.

“Bend over for me.”

‘Oh God,’ thought Olivia. Olivia could feel the officer’s gloved hands gently spreading her butt cheeks. She could feel her fingers probe her butt hole. Her fingers started to work their way down.

“Bend over a little farther for me. Touch your toes.”

Olivia could feel the officer’s fingers make their way down to her womanhood. Suddenly she felt a finger being inserted slowly into her and she let out a muffled moan. This was so degrading, she kept thinking. She tried not to think about it but the officer’s slow movements actually felt good. After a moment she removed her hand.

“Turn around for me.”

Olivia did as told.

“Open your mouth, wide.”

As Olivia opened her mouth, the officer pulled out a small flashlight from her pocket and started examining her mouth.

“Lift your tongue.”

Again Olivia did as told. As the officer turned off the light and put it back in her pocket, Olivia breathed a sigh of relief. The officer walked over to a small cart and came back with a one-piece orange jump suit.

“Put this on. This is what you will be wearing for the remainder of your stay. The snaps go in the front.”

Olivia put on the jumpsuit as the officer watched intently. As she put it on she noticed only two of the four snaps actually worked. She could see in a nearby mirror that her breasts were clearly visible from the sides and if she leaned over, the top portion of her neatly trimmed pubic hair was exposed.

“Do you have another jumpsuit? This one is missing snaps. Please.”

“No,” said the officer. “It is the only one in your size.”

Olivia was frantic. ‘Oh my God,’ she thought. ‘This is a nightmare. Someone please get me out of here. Please.’

The officer led Olivia out of the room and down the hall to a holding cell. There was another inmate in the cell, also in an orange suit.

“Wait here till we have your cell ready,” the officer said. “It should be soon.”

The officer closed the door with a sharp clang. Olivia tried not to stare at the other inmate. She was a large woman with close-cropped hair and faded monochrome tattoos. Olivia could make out the name Wendy tattooed on the girl’s forearm. Oh My God, she thought. I would hate to be her cellmate.

“Hi, I’m Andy,” said the other girl. “What you in for?”

“Possession,” quipped Olivia. “My boyfriend set me up.”

“Sounds like a boyfriend you don’t need. Ever been with another girl before?”

“No, and I don’t intend to,” said Olivia sharply.

“Don’t worry. You will. You’ll be Gay for the Stay, just like all the rest. You’ll see.”

Gay for the stay. Those words cut through Olivia’s mind like a hot knife through butter. There was no way Olivia would ever let that happen.

“Andrea Jackson?” a guard asked at the cell door. “Come with me.”

Andy was led out. Olivia was hoping she could get her cell soon so she could lie down in peace and collect her thoughts. She was cold, she felt naked and she was scared. About 20 minutes later another guard appeared at the door.

“Olivia Diaz. Come with me.”

Olivia was led down the hall to her awaiting cell. There were a few hoots and whistles from some of the girls in the cells as Olivia passed by. They finally arrived at the cell.

“24 North,” shouted the guard. “Open.”

The door opened with a loud buzz.

“Welcome to your new home.”

Olivia didn’t say a word as she walked into the cell.

“You get the top bunk,” a voice said from below. Olivia could not see the face at first, but the voice sounded familiar. It was Andy. Oh my God.

“Hey, look who it is. We’re going to have a real good time, you and me.”

Olivia climbed up to the top bunk and lied down. She was tired. It was a long day. In a little while she was asleep.

Sometime later Olivia awoke to find a hand on her thigh. It was Andy. “What’s up precious?”

“Please don’t touch me. Please. I’ll scream.”

“I wouldn’t do that if I were you,” with that, Andy put her hand over Olivia’s mouth and began climbing up the bed and into the bunk. She got next to Olivia in the bed, keeping her hand over her mouth the whole time. There was barely room for the two of them in the small bunk. The big woman had her leg between Olivia’s legs, her thigh firmly pressing Olivia’s thigh and moving her leg up and down along Olivia’s legs.

“Feels good, don’t it?”

Andy began to feel Olivia’s breasts with her free hand. At first she gently caressed them and then she firmly squeezed her left breast.

“Oh, these are nice,” Andy said, “I can see we are going to have a good time you and me.”

Andy gave Olivia’s left nipple a soft kiss. With that she released her breast and stopped stroking her leg.

“I’m going to release your mouth and if you say a word your ass is mine.”

Olivia was paralyzed with fear as the girl took her hand away. Olivia just lied there shaking as the other girl got down.

There was no other incident the rest of the night. Still, Olivia had a hard time sleeping. The other girls in the cellblock made noise all night, hollering and talking trash. The hard mat was so uncomfortable. Of course it was cold.

The next morning started with breakfast. The whole cellblock ate at the same time. Olivia quickly got her food and found a seat. She felt the whole room was staring at her. She hoped she could eat quickly and keep a low profile. Her hopes were dashed when she looked up and saw Andy approaching. Andy put her tray down in front of the seat right next to hers and walked up behind Olivia. Olivia began to get nervous in anticipation of what might happen next.

“Hey all, I want to introduce you to my new celly, Olivia.”

“She looks fine. I’ll give you a carton of smokes for her!” one of the inmates shouted across the room. There was laughter from other inmates.

“No, she’s a keeper. All mine.” With that, Andy started to run her fingers through Olivia’s long black hair. She then started caressing her neck and ran her hand up and down her cheek.

“Keep your hands off me!” screamed Olivia. With that, Olivia picked up her orange juice and threw it in Andy’s face.

“Bitch!” shouted Andy as she slapped Olivia hard across the face, knocking her onto the floor. Andy got on top of her and the two started going at it. Olivia’s nipples could be seen plainly exposed by her ill-fitting jumpsuit as the two rolled on the floor. Other inmates gathered around and started cheering. It was instant mayhem as the two girls went at it like animals.

The ensuing struggle brought almost immediate attention from the guards. In moments two correction officers were standing over the sweaty girls breaking them apart. One of them lifted Olivia up off the ground by her shoulders. Andy got up.

“Alright, what happened here?” shouted the guard. “Hey Andy, welcome back!”

“Yea, glad to be here, Pam,” said Andy. It was clear they knew each other.

“What you in for this time?”

“Picked up on an old warrant. Bullshit,” answered Andy.

“I have to take yous and write yous up you know.”

“That ain’t fair, she started it!” said Olivia.

“Don’t matter. There is no fighting.”

Pam led the two down the hall to a small office. She seated them and proceeded to fill out some paperwork. After about ten minutes she handed a paper to Andy and told her she could go back to her cell.

“We all taken care of?” Andy asked.

“Yea, we good,” Pam said, “You can still get shit?”

“Hell yea!” quipped Andy. It was clear these two knew each other and there was something going on other than a normal inmate guard relationship. “I got peoples coming next week. I’ll see what I can do.”

“Don’t forget me,” said Pam, “You go. I want to have a talk with the new girl.”

“OK. I’ll get back at you next week.” With that Andy left the room.

Andy’s exit left Olivia alone with Pam. Pam smiled up at her with a sinister looking grin and then walked around to the front of the desk. She sat down on the edge of the desk and stared at Olivia with that grin on her face.

“I have to write you up for fighting, you know,” Pam said. “That is a whole ‘nother charge. Could keep you here another six months, maybe longer.”

“Please, no, please!” pleaded Olivia.

“I have no choice. Sorry.”

“Please, please. I’ll do anything! Please!”

“Hmm. That is what I wanted to hear.”

With that Pam removed her nightstick from its holster and started to slowly rub her own crotch with it. Slowly, up and down she rubbed the front of her pants between her own legs.

She then took the nightstick and in one sharp, quick upward motion undid the two snaps holding closed Olivia’s jumpsuit. Olivia’s breathing became so heavy you could hear every breath. Pam started to tease Olivia with the nightstick. First she started stroking her cheek with it, then on down to her breasts. Pam got off the desk and walked around behind Olivia’s chair.

“Get up,” she said as she hoisted Olivia out of her chair. As Olivia got up her jumpsuit fell to her ankles. She was standing in front of Pam stark naked her beautiful olive skin in full view. It was a feast for Pam’s eyes. Pam took the nightstick and dragged it up and down Olivia’s butt crack. She then walked around in front of Olivia and stuck it hard right between Olivia’s legs. Olivia closed her eyes as she let out a sharp moan. The nightstick was cold against her clit. Pam started to slide the nightstick up and down against Olivia’s neatly trimmed bush. Pam could hear Olivia’s faint moans and sighs with every stroke. Pam again walked around behind Olivia.

“Bend over, bitch!”

“Oh please, no!” Olivia pleaded.

“It’s this or six months more. Your choice.”

Olivia slowly bent forward. She again felt the nightstick against her butt this time edging slowly against the resistance of her butt hole.

“Lean against the desk with your arms wide,” Pam insisted.

Olivia did as told. She could feel Pam back the stick off her butt, but instead Pam started to ease it into Olivia’s tight pussy. Olivia started to moan as Pam slowly started to ease the cold nightstick in and out. First it was just an inch or two, then farther and farther. The stick was cold and its large diameter was more than Olivia was used to. Pam kept at it, each time pushing the stick up further and further into Olivia’s tight, moist cunt. Pam started to push it in and out faster and faster as Olivia felt Pam’s finger’s from her other hand reaching between her legs and finding her clit. As degrading as this was it was starting to feel really good to Olivia and in minutes she started to moan deeply and could feel an orgasm coming on. Within moments Olivia was spread out on the desk, writhing in delight, the nightstick humping her tight pussy like a dog.

Pam slowed her movements down as Olivia came back down from her climax. Pam quickly jerked the stick out of Olivia’s pussy and thrust it into Olivia’s butt in a quick motion that caused Olivia to scream. Once again Pam started pumping the nightstick. Her thrusts became quicker and quicker and Olivia’s moans became louder and louder. Once again the girl became overcome with pleasure, wetting the desk with her cum and wetting Pam’s hand. The inside of Olivia’s thighs glistened with her juices and her back was shiny with her sweat. Pam pulled out the stick quickly once again and placed it down on the desk next to Olivia’s face.

“Put your jumpsuit on and get out of here,” Pam said. “If you tell anyone, you’re a dead girl.”

As Olivia started to walk out, Pam suddenly jumped up and stood in front of her. “You know what?” Pam said coyly, “I don’t think I’m done with you. Down on your knees Bitch!” Pam was shouting at this point. “On your fucking knees, Bitch!”

With that, Pam took the nightstick and put it between her thighs up by her crotch. The stick was angled up at about 45 degrees, like an erect penis. “I want you to suck me off! And make sure I cum.”

Olivia hesitated. Pam grabbed the girl by her hair and held her head inches from the stick. “Are we going to do this the hard way? I can shove it through your teeth!”

Olivia opened her mouth and slowly placed her lips on the hard stick. She could see streaks of shininess from where the stick had just come out of her own ass.

“Come on Bitch, make me cum!” She began to move Olivia’s head up and down by tugging at her hair. Her movements became more and more violent with every thrust.

“Come on Bitch!” she was shouting once again, “Come on Bitch! I said make me cum!” Pam was aggressively moving Olivia’s head up and down on the stick. You could hear Olivia’s mouth making slobbering sounds as the saliva ran down the stick. Pam kept shouting,

“Come on Bitch! Make me cum!” as she just kept getting more and more violent. She was wildly moving Olivia’s head up and down on the nightstick as Olivia’s drool ran down the stick and started to puddle forming a wet stain on Pam’s pants. Finally, after about five minutes Pam stopped.

“I guess it ain’t gonna cum. I bet it’s the hardest dick you ever had!” She was still shouting. “Snap up your suit and get the fuck out of here.”

Olivia ran out the door as fast as she could before Pam could change her mind. Once around the corner she stopped and leaned against the wall in an effort to catch her breath. She was panting from excitement. She couldn’t talk, just pant. A few minutes later she walked back to her cell.

Upon being buzzed into her cell, Olivia immediately climbed up to her top bunk and lied down.

The ordeal she just went through took a lot out of her. She was hungry, tired and felt the need to take a shower badly. She asked Andy when lunch was, and was told she had just missed it. She also asked about taking a shower and was told shower privileges were at two. That was about an hour away. She had time to rest and try to calm her mind.

Two o’clock finally arrived and the inmates would be allowed to move about the jail, within limits of course. Inmates could watch TV in the dayroom, play basketball in the gym, use the phones or take showers. Olivia really looked forward to the shower. She got a clean towel and facecloth from the trustee for her cellblock and headed down to the shower room.

When she arrived at the shower room Olivia was pleased to see it was not crowded so there would be no wait. Olivia undid the snaps on her jumpsuit and let it drop to the floor. She picked it up and placed it on a hook on the wall. She made a mental note to try to get another clean jumpsuit as soon as possible. Hopefully one with all the snaps in the front.

Olivia got in the shower and turned it on. The water was a bit cold but boy did it sure feel refreshing. She stood there for a couple of minutes and let the water just run over her body, the drops running off her long black hair and down her back. Oh, did it feel good.

After a few minutes of this Olivia grabbed the soap from the rack and began to soap up her body. First her arms, then her legs and on up. As she stood there soaping herself up, with her eyes closed and her face pointed up towards the oncoming stream of water, Olivia suddenly felt a hand on her butt. She turned around to see Andy and two other girls, all completely naked. She was so engrossed in the shower she did not notice them enter the room.

“Looks like you need some help soaping up,” said Andy, “We’re here to help.”

Andy bent down and took her bar of soap and started soaping up Olivia’s legs one at a time with long firm strokes while her two friends each held Olivia by the arms. Andy started to kiss and nibble at Olivia’s lovely firm ass which was right in front of her face. She then slipped her tongue between her butt cheeks and darted it in and out while going up and down her butt. She continued moving the soap upward from her legs and started to soap up Olivia’s ass with firm massage like motions. She made sure to carefully soap up her asshole and as the running water ran down Olivia’s butt crack, Andy would flick her butt hole with her tongue and re-apply the soap. In the meantime, the other two girls were nibbling at Olivia’s ears and soaping up her upper body paying special attention to her breasts and hardening nipples. Olivia was covered with quite a bit of soap at this point. The girls turned her around and Andy judiciously soaped up her soft bush.

“I could use a good cleansing brush,” she joked as she rubbed her face against Olivia’s soaped up mound.

“Looks like it’s time to rinse her off,” Andy said and with that the girls each grabbed Olivia under the arms and Andy grabbed her by the butt and they hoisted her up with her legs in the air with her soapy mound nearly eye level directly under the stream of cool water. Olivia shut her eyes and let out a moan as the cool water hit her clit. Andy moved her right hand up to Olivia’s pussy and slowly inserted first one, then two and finally three fingers, vigorously working the girl into a frenzy. The water was rushing over her body and with her butt aimed high in the air the soapy water was rolling down past her rounded breasts and streaming down her long black hair. With her head tilted back her hair nearly touched the floor as the soapy water dripped off it forming a slippery puddle on the tile floor. The girls continued to soap and fondle each other in the shower for some time enjoying the feeling of the water rushing over their bodies. After it was over they took turns toweling each other off accompanied by lots of giggling and caressing. After a bit of playful towel snapping and long kisses they helped each other get dressed and headed off to the dayroom.

Later that day at dinnertime Olivia and Andy sat next to each other. Andy would sometimes reach over and caress Olivia’s leg or arm. If she was bothered by it, she certainly didn’t show it.

Olivia ended up getting released after serving half her time. She did the remaining time on probation.

When it was time for Olivia to leave, Andy handed Olivia her phone number on a slip of paper. “I should be out of here in a couple more months,” she said.

Olivia took the paper and thought, ‘the nerve of her, I have a boyfriend.’ Olivia thought about her recent past and what Kenny had done. She stuck the piece of paper in her pocket.