Prison Psychologist Month 02

Before long her wrists and ankles were tied securely. She lay helpless across the table. Her heavy breasts hung towards her sides, but only slightly so. Most of her sweet flesh was piled on top of her chest. Her nipples were erect and sticking straight up like rosy thimbles which had been placed opening down on top of a mound of jiggling lemon Jell-O.

First up was Tommy Cronin who had been sent to Cedar Junction long before the prison had been re-named. It had been nearly forty years since Tommy had been this close to a woman, and in his sixty some odd years he had never been this close to such a beautiful woman. "Tommy, which hole do you want?" asked Billy.

"I want to fuck her pussy, Billy," said Tommy as he positioned himself in front of her spread legs. The rest of the inmates gathered around to watch the show. Tommy slowly slid his hands northward along the inside of her white, athletic thighs, pausing momentarily so that his rough hands could squeeze the pliable skin. Then, when he had almost reached her pussy, he hiked up her simple black skirt and then reached up to pull down her panties. They were soaked from Cindy's arousal. "Finders keepers!" he shouted. The room erupted in laughter.

For her part, Cindy was excited, not afraid, but she did shake a bit for effect, as her tits jiggled like a fleshy seismometer. Tommy unzipped his pants and pulled out his penis, which was both hard and straight, neither remarkably large nor small. "Don't! For heaven's sake please don't do this to me," she cried. Tommy didn't miss a beat as he sidled up to her pussy and, making sure that his aim was true, jammed his cock between her labia. Cindy howled and pulled back but was unable to avoid the next thrust, or the ten that came in quick succession as Tommy hit his stride.

Meanwhile, Jim Ward said, "I'm next."

"Hold on, Jimmy," said Tom, "my time isn't up and I'm not finished yet."

"No offense, Tommy, but I'm not rushing you. As far as I'm concerned you can ride her all day. No sloppy seconds for me. I'm interested in her mouth," said Jimmy. Tommy, we can both do her at once. Open wide, Doc." In a moment Jim's prison pants were around his ankles and he had Cindy's hair grasped firmly in each hand, pulling out and down. Cindy's mouth was firmly closed. It's not that she thought that she could fend off the assault; rather she wanted the convict to force her to accept his stiffened cock. Her fantasy was to be forced to have sex, to be taken roughly, seemingly against her will. Jimmy obliged. "Open, bitch," he snarled, and then slapped her across the cheek. Cindy clamped even further. "Open your fucking mouth, bitch or the next one will break your jaw. I hit just as hard as Billy"

Slowly, as her hair was pulled even more strongly, Cindy relented and he lips parted, showing her perfect teeth and then her tongue and throat. "You know the rules, Doc," said Jimmy. "If you bite me I will snap your fucking neck and fuck these cons if they don't like it."

Cindy simply nodded "Yes," and then opened her mouth. In a moment, Jimmy's cock was in.

"Suck it. Suck it real nice." He demanded. For her part, Cindy closed her lips and began a slow and soft sucking motion, like she would do for a lover. Jimmy re-grabbed her hair and before long, the convict had matched her tempo, tugging her hair to drive her throat forward while his hips pushed in the opposite direction. Before long he was entirely buried in her mouth up to his ball sack and pumping in rhythm. Three feet away, facing Jimmy and wearing a shit-eating grin, Tommy was close to finishing up, moments away from blasting his cum into the helpless captive. His climax was hastened by the fact that Cindy was now thrusting to meet each of his strokes, clearly participating in and not just enduring her rape.

At the end, Tommy lurched forward and grabbed Cindy's tits, squeezing them as if he had fallen off a cliff and the only thing between him and the canyon floor were Cindy's luscious tits. "Uh, uh, aargh!" Tommy shouted as his cock exploded inside Cindy's grasping pussy. His frantic last penetrations were reduced to a slow intermittent cycle as he milked the last moments of what was surely his last real fuck. He backed up, turned to the clapping audience and said "Next."

In a minute the next in line advanced to replace him. Meanwhile, Jimmy's cock grew even larger and more turgid thanks to Cindy's practiced oral ministrations. His thrusts accelerated slowly becoming more violent, until his final push erupted deep in the back of Cindy's throat. Jimmy's cock squeezed out five different shots of warm sticky cum, but he did not remove his cock. He wanted Cindy to swallow his splooge and she obliged. Jimmy could see and feel her throat contractions. After a while he slowly withdrew his wilting penis. Cindy shook her head back and forth, but said nothing as the next two convicts mounted her fore and aft.

At quarter after three, Randy stepped from the cab whose driver he had "convinced" to take him from Logan Airport in East Boston all the way out to Walpole. Randy walked over to the nearest black and white, which happened to be a local Walpole cruiser and extended his hand to the officer who was leaning against the cruiser enjoying a cigarette. As he transferred his cigarette from his right hand to his left while reflexively extending his right to shake, the officer spoke. "This place is off limits, Sir. Don't you watch television?" Their hands touched.

"Officer," said Randy I am the replacement hostage negotiator and I need you to do two things for me. First, I need to know the current status of the siege here and then I need you to drive me to the location of the current hostage negotiator and then to the officer in charge. Who is he, by the way?"

"That would be Major Barnes of the State Police, sir." In two minutes the local cop had described the current state of the situation- stalemate, and had motioned to Randy to get in the car. They drove to the main command post and walked into the tent. The Walpole officer motioned to the hostage negotiator to come over. As he approached, the Amazing Randy extended his hand. It was taken in kind and Randy spoke silently to the negotiator, whose hand he still held.

"From this moment you will bend to my will and support any story I tell to the State Police. Do you understand?"

"Yes, I understand." After that Randy spoke quietly to the real negotiator until they walked over to the state police commander. Major Barnes, this is my replacement, Rudy Jiminski. He's been called in to take over the hostage negotiations. I know him. He's the best at what he does"

Major Barnes took off the trooper glove on his right hand and shook Randy's hand. Randy spoke calmly while he continued to shake the trooper's hand. "Major Barnes, we need to get a man on the inside. I will be that man and you will make the necessary arrangements- immediately. First I need a look at the layout of the prison, complete with all exits from the mess hall. I imagine that there's some kind of delivery entrance and that it's currently guarded."

"There is, and it is." said the trooper.

Once I have entered the prison, you will quietly command the guards at the service entrance to return to the central command area. You will place an unmarked state police undercover vehicle there, but no guards. You will see to it that the keys are in it and that there is sufficient gas to make it to Providence, or beyond. Additionally, you will instruct the perimeter guards to allow it to pass without inspection, that is, to just wave whoever is driving it through. By the way, you really like this plan.

"Certainly, Mr. Jiminski," said Major Barnes. "By the way, I like this idea a lot."

"I assume that you have set up communications with the rioters."

"We have," said the major, "although they're a bit tenuous, just a single cell phone belonging to one of the hostages- the prison psychologist."

"What is the current state of the negotiations?"

"Presently, we're stalling for time while we formulate a plan to breech the facility. Oddly enough, the inmates don't seem to have any particular demands other than a bus to get them out of here. It's like they just want to stay there. They are definitely not in a hurry and we are definitely not going to give them a bus."

"New plan, Major Barnes," said The Amazing Randy. "You're going to really like it. You're going to call whoever is in charge in there and say that you wish to send in a single, unarmed negotiator to finish the negotiations and that their bus is fully gassed and ready to go. If they protest, then you ease their fears by whatever means necessary, but you do not hang up until they have agreed to allow me into the prison. Can you do that for me, Major Barnes?'

"Of course I will, Mr. Jiminski," said the state trooper. "This is a great plan. Can you give me a few minutes to recall the men and get the unmarked in position? Then I'll call inside."

"Certainly, Major," said The Amazing Randy. "Thank you for your cooperation." With that, Randy rolled up his shirtsleeves to expose his forearms. He expected to be grabbed by whoever met him at the gate. When that happened, he'd have that person firmly under his control. The rest would be placed under hypnosis one by one as he encountered them. Only one more thing was required to complete his plan. He needed for Cindy, who would surely recognize him, to be in on the plan at least to the extent that she would not let on that she knew him as anything other than a hostage negotiator.

"Major Barnes, when you speak to the inmates you must insist that I be able to speak to Dr. McCarthy over the phone. Offer them something they might want if they say no. I must speak to Dr. McCarthy. Do you understand?"

"I do. I'll make it happen," said Major Barnes.

It had been three solid hours of constant degradation for the beautiful blonde psychologist. She was a sight. Her face and neck were covered with the cum of eight different convicts. Her beautiful tits were bruised from the severe manhandling they had taken from every single convict who had taken her. Now there was only one left and it was Billy Sanderson who, true to his word had waited for every man in his crew to have his way. He took one look at the cum-covered psychologist beauty, and said, "Boys, turn this cum slut over on her belly and spread her legs wide. Keep that ass in position at the end of the table. I'm going to finish her off."

Cindy moaned as the convicts complied with the gang leader's commands. There was not even a shred of respect or delicacy displayed to the bruised beauty who had been reduced to meat- pawed, poked, and forced to swallow cum from one rapist after another for hours. She was shaken, but not broken. For the better part of her ordeal she had secretly been enjoying her degradation, but by now she had had enough. Her aching pussy was soaked in cum from a dozen rough men.

Now she was going to be taken forcefully and anally by the gang leader, Big Billy Sanderson. She had two choices, she thought to herself, submit to him quietly, or play this final role as the frighten damsel in distress. After that she did not know, but she suspected the worst. If the state troopers attempted an assault, she and the two bound troopers were as good as dead. Deep inside she knew that they were probably going to die anyway. She determined that she might as well continue her fantasy. She'd give them their money's worth. Damsel it was.

Cindy had been taken anally before. In each case the men who had enjoyed her magnificent rump had been gentle, slowly easing themselves into her sphincter, which they had taken the time to prepare with multiple mini-intrusions as they spread the muscle slowly until it could accommodate their cocks. Luckily, none of these lovers had been especially well-endowed so Cindy could enjoy the experience which, she had to admit, had been highly different from and every bit as satisfying as vaginal sex.

As Billy moved into position Cindy's phone rang. He turned to the splayed-out beauty and chuckled out loud. "Sorry, darlin' but I need to take this call. Don't fret; I'll be with you in a minute or two." With that he picked up the phone and said "Where the fuck is my bus?" A conversation ensued in which Big Billy kept saying "no" over and over. Finally, after a long pause, he shook his head and said, "OK, but if there's any funny business, the Doc and the guards will be dead in a minute. Put him on."

Then, with a solid slap to he exposed buttocks he said "It's for you, Doc. Everything's just fine. Make sure they get the message or you won't live to see the sunrise." With those words, he held the phone so Cindy could both hear and speak.

"Hello," she spoke through her cum-covered lips.

"Cindy, you will obey me. Do not speak; just listen," said the voice on the other end of the line. It was a voice she knew very well. Despite the fact that she had not heard it in years, so powerful was his control over her that she was back under the influence of The Amazing Randy in an instant. She listened and he spoke. "Cindy, in a few minutes I will be coming in to get you. When you see me, you will not indicate in any way that you know me until I release you. Do understand, Cindy?"

"Yes."

"Now give the telephone back to the person to whom I was speaking earlier."

"I'm done," she said to Big Billy.

Billy brought the phone back to his ear and said "I'll have someone waiting in exactly one half-hour at the east gate. One guy and one guy only. Any funny stuff and the Doc and the two screws are dead. Got it?" He hung up.

He unzipped his prison blues and took out his cock. It was huge; Billy was hung like a horse. Cindy, who was still tied to the table face-down and couldn't see the gigantic cock taking dead aim for her anus. Cindy went into her "damsel in distress" voice. "Please," she pleaded, "please don't. I've never had sex that way. I've never been taken like this. Please!"

Big Billy stepped out of his trousers and, stroking his already erect cock, sauntered to the other side of the table so that the beautiful, blonde psychologist could see his face, but not his 'package,' which was hidden below the plane of the table top. "Well, Doc," said Billy, "if I'm to be the first, then you need to know that you're starting at the top. It's just you and me and this!" He reached his right hand down to grab his massive cock and slammed it down on the table in full view of his hostage.

Cindy's eyes went wide as she stared at Big Billy's enormous meat. It was as big as a four pound knockwurst. It was nearly two inches in diameter and had to be a foot or more in length. She was no longer playing damsel in distress; she was in distress. In a few moments Billy would be trying to put four pounds of throbbing meat into a tightly bound two pound sack. She screamed. "No, please no. I can't take that. It's gonna hurt too much. It will never fit!"

"Yeah, it's gonna hurt all right," he said as he walked back to position himself behind her, all the while slowly and methodically stroking his huge cock. "Sully, go get me some butter, or some cooking oil. This is gonna require some lubrication. I don't want to kill her, just fuck her up the ass."

"Oh my God, please don't hurt me like this. I'll do anything you want, anything. Please," she begged, with genuine tears falling from her makeup and cum-crusted eyes.

"But Doc," Billy laughed, "this is what I want" The tied hostage wriggled and shook, but her binding was tight. Billy slapped her ass very hard, so hard that Cindy had to inhale in mid-plead so that she could howl.

"Owwww!"

"Stop wiggling, Doc, or the next one will be harder. Sully, where's that oil?" he shouted.

"Got it, Billy," was the reply from Sully who entered the mess hall carrying a gallon jug of Sysco cooking oil.

"Give it here," said the gang leader. He grabbed the jug and unscrewed the top. Piercing the seal with one finger, he tilted the jug and poured a handful of lubricant into his right hand. He smeared the slick oil all over Cindy's tightly clenched butt crack and said "Doc, you gotta ease up a bit. I'm warnin' ya. It will go a lot better for you if you relax."

Cindy knew that he was right. She slowly relaxed her sphincter while Billy slobbered her perfect ass with even more lubricant. He continued, slowly stroking his cock with oil as he moved to insert it. It was not a good fit, but he persisted, pushing and guiding the tip of his cock until it was nestled snug against her puckered anus. He paused for a couple of moments and then pushed forward slowly, but inexorably, the swollen tip putting pressure on the captive beauty's anus. Cindy could feel the pressure and was doing everything she could to yield to the enormous phallus demanding entry. Something had to give.

Finally, with a lightning bolt of pain and a thunderous scream from its intended victim the tip of Big Billy's cock forced its way past her sphincter and was in. Again he paused, savoring the vise-tight grip of Cindy's anus. With a grunt, he pushed his cock farther and farther into the captive psychologist's yielding asshole. Big Billy's cock filled her completely, stretching her muscle to its absolute limit. "Oh, God," she cried out. "It hurts! Stop, please stop!" She tried to squeeze him out, but it was too late. She'd been speared by Big Billy's enormous invading prick.

He continued to press forward, despite Cindy's thrashing and loud plaintive protests until his penis was better than three quarters of the way, buried deep inside her. It was just about as far as it would go. Then he slowly withdrew until only the tip of his dick remained. Cindy became still, lying there on the dirty table, breasts smashed against the surface. Again he reversed direction and pushed. This time the invasion was slightly less painful and Cindy moaned as Billy's dick head reached the end of its run.

Now the pace quickened a bit- in, out, in, out, until Billy established a rhythm that both he and Cindy could handle. Billy pushed and pulled, savoring the fierce grip of Cindy's rectal muscle around his cock. He moaned in pleasure as he continued to pump. For a convict like Billy, it was about as good as he was ever likely to feel and he intended to make the moment last.

For Cindy's part, she too felt a kind of relief as the startling violence of the initial assault melted away into acceptance. She began to move her ass to Billy's rhythm, involuntarily at first, but then with a purpose. Cries turned to moans as the two motions synchronized. Billy and Cindy continued their pace for a few more minutes until Billy began to increase his pace, moving towards climax. Cindy recognized what was happening and she increased her pace as well. Her worn pussy began to secrete new juices as she rubbed her clit against the table, stimulating herself as she too moved towards a climax of her own.

Faster and faster the pair moved together until Billy's reciprocating rod stopped in mid-thrust and he shouted in pleasure. His cock erupted as cum shot out of the tip and Cindy's ass swelled like a water balloon under the kitchen faucet. All she could feel was one contraction after another, a half-dozen in total, filling her ass with Big Billy's essence. The warmth of the cum combined with the feel of Billy's cock which slowly resumed his pumping motion in denouement was enough to push Cindy to her own climax.

When it came, it came suddenly and violently. She raised her head off the table and screamed as her ass tried to push Billy out. At first she failed, but the inevitable deflation of his erection combined with her persistent squeezing eventually forced him to withdraw. Now that her asshole had become unplugged, thick globs of milky white jizz oozed from her asshole which, having been stretched to the limit could not quite re-seal itself. Gurgling bubbles of cum powered by compressed air and contracting muscle slipped through the opening and dropped to the floor below, where a pool began to form.