His Real Estate Ch. 03

Rupert steered his electric car onto the freeway. He set the auto pilot and relaxed as the car found its slot in the fast lane. There wasn't much traffic. He made good time along the Jefferson Davis Freeway. Soon he was on the narrow roads that led to his house.

The car rounded a bend and Rupert noticed a chain gang planting small trees in a park. There were several convicts standing near a large puddle at the edge of the road. On a whim Rupert steered towards them and sprayed three large men with muddy water. Rupert laughed as he watched their angry gesticulation in the rear view.

While his attention was distracted he failed to notice a second, larger puddle in front of the car. He drove straight through it. It was much deeper than the other puddle. The front wheels of the vehicle lost traction and the car slid sideways. Rupert hit the brakes and the car stopped. He tried to drive forward but the car was bogged. The wheels spun uselessly as Rupert cursed his stupidity.

Rupert kept spinning the wheels for few minutes but then gave up. The car's batteries were running low. The sun was setting. Rupert didn't know how long it would take Roadside Assistance to find him. He reached for his mobile phone. It wasn't in his pocket. He cursed again when he realised that he had left on his desk.

After about half an hour Rupert realised that four of the Convicts were standing near the car. They were laughing at him. He wound the window down. He saw the electronic control bracelets on their ankles and knew that their overseer must be close. Rupert asked them if they could push the car back onto a dry piece of road. They laughed. He offered money and they stopped laughing.

It took a few minutes but the deal was done. The four men, all young and muscular, started pushing the car. It was soon out of the puddle. Rupert reached into his wallet and fished out several large notes. He put his hand out through the window.

The largest of the men grabbed his arm. Rupert screamed. The man's hand was soon on his face, forcing his mouth to close. In a moment Rupert had been dragged from the car and flung on the muddy ground. Another man used his foot to force Rupert's face into the mud. The four men stood over him as they worked out what to do.

It took a few minutes but Rupert stopped struggling and accepted that he was helpless. They carried him to a picnic area that was surrounded by thick bushes. One of them went back and drove the car off the road. He hid it behind a billboard and jogged back to the group.

The largest of the men stood behind Rupert. Two of the others lifted his arms and they dumped him onto a picnic table. They bound his arms with fencing wire. The largest guy began undressing. When he was naked he took one of his wet socks and shoved it into Rupert's mouth.

Rupert started squirming but a few punches to the side of his head quietened him. The men roughly yanked his pants off. They grabbed his legs and spread them. The naked man started rubbing his cock against Rupert's anus. His friends pulled Rupert's legs and his hole opened. Rupert had tears in his eyes as he felt the head of that hardening penis enter his virgin orifice. The guy's cock was soon at full hardness. He leaned into Rupert as he pushed that cock deeper into Rupert. He reached underneath and started squeezing Rupert's balls. Rupert's cock was getting hard. The guy was fully inside Rupert now. He rested, loving the feel of that tight anus stretched around his manhood.

The other three men quickly undressed. They all stood in front of Rupert as they started to masturbate each other. Rupert was so tightly bound that he could not move his arms or head. The weight of the guy who was fucking him kept him pinned to the table. All he could do was wait for the guy to finish.

The guy started moving his cock in and out of Rupert. Slowly at first but he increased the pace. Rupert's hole was dry but some saliva eased the way. The convict had a large cock, nearly 10 inches but it was narrow. He was soon fucking Rupert with deep rapid thrusts. The other three started egging him on, they were all hard by now. They cursed Rupert, telling him what a slut he was. They were going to make him their bitch. The guy let out a moan as he grabbed Rupert's hair. He shot a huge load of seed into Rupert and collapsed on top of him.

After a few moments the next guy took his place. Rupert was well lubed now. The guy had been playing with himself too long and he came after about five strokes. He pulled out and the next guy plunged his meat into Rupert's arse. This guy's cock was short but it was thick. Rupert grimaced as the guy pounded him. He started squeezing Rupert's balls. He almost crushed them in his fist. Rupert started crying but this only made the guys tease him more. They told him to shut up and get used to it. He was their new toy.

The guy humped a load of cum into Rupert's hole. As he pulled out he brutally smacked Rupert's cheeks.

The fourth guy hit those tortured ass cheeks until there were red. He spread that wet butt and shoved his cock in. He was only average in size but he made up for that with speed. He pumped in and out of Rupert like a hungry goat, humping him till he filled Rupert with his thick semen.

The four of them gathered around Rupert's head. They pulled the sock from his mouth. The biggest guy kissed Rupert passionately then took a step back. He was hard again. He waved his cock at Rupert and mockingly asked him if he was going to swallow. He moved closer and Rupert had his first taste of cock.

When that cock was touching the back of his throat Rupert saw a prison guard walking up behind the group. The guy pulled his cock out of Rupert's mouth. Rupert began to relaxe.

The guard walked up to Rupert. He patted his head and told the convicts to stand back. He walked behind Rupert and tested the strength of the wire that bound him to the table.

Rupert waited to be released for several minutes. He wondered what was going on. Rupert screamed when he felt another hard cock entering his rectum.

As the guard started to fuck Rupert he told the convicts to shove a cock in Rupert's mouth to stop that screaming.

As the guard humped Rupert's arse he leaned forward and grabbed Rupert's hips. He started to ram his cock in and out of that wet arse.

The guard looked at the convicts as he said "This bitch is so sloppy, you boys must have worn him out." He pushed into Rupert and unloaded another load of cum into that butt.