Here is a Jessie/Bertram pairing that I wrote.
Still horny after Luke's wild ride, Jessie is on the prowl for one more cock before she can sleep. There is only one more in the penthouse. As disgusting as Bertram was Jessie was in need of some more cock...
Jessie could hear opera music coming from just beyond the door. She knocked but Bertram did not answer the door. So she slowly opened the door and noticed what a mess the room was in. Bertram had stuff stacked from floor to ceiling. Jessie realized that Bertram was a hoarder.
The fact that Bertram was a hoarder did not matter right now. She just needed cock. Jessie scanned the room and noticed Bertram lying on his bed, dozing, wearing a pair of loose fitting shorts and a tee shirt. Across his chest was a playbill for an opera that was scheduled for later that week.
Jessie was making her way to Bertram's bed to wake him up and see if he wanted to have some fun when a small glass jar with many small colorful objects inside caught her eye. She picked the jar up and looked closely at the objects and found them to be plastic clothes pins. The memory of what Ryan did to her nipples with those clamps popped into her mind and that sparked an idea. Why not put these on my nipples and see if they feel the same as those clamps.
Opening the jar, Jessie reached in and pulled out one red and one purple clothes pins. She placed the jar down between her legs as she got up on her knees to place the pins on her nipples. The pins had tightly wound springs and were made of extra thick plastic. The anticipation of how painful these pins were gonna be excited Jessie and her pussy started to get warm and wet.
The first pin closed on Jessie's left nipple and it shot a jolt of pain down through her body and stoked her already warm pussy even more. When the second was pinned on her right nipple she could not help but let out a loud high pitched moan that clashed with the opera music that was playing. Jessie was dripping wet now. Droplets of cum dripped down into the jar of clothes pins.
It was not Jessie's loud moan that rose Bertram out of his dozy state. It was how the moan clashed with the music that woke him. He looked over to where he heard the sound and saw Jessie's back and bare naked ass straddling his jar of colored clothes pins. What was worse was Jessie was leaking all over them.
"Jessie, stop that." Bertram jumped out of bed and knocked Jessie face first into a giant dust bunny. Bertram grabbed the jar and inspected the contents. He could see drips of Jessie's cum coating several of the pins. This infuriated him. He grabbed the closest paddle looking object, which turned out to be an 18 inch metal pizza peel. With all his strength, Bertram raised the peel high in the air and brought it down hard on Jessie's ass.
WHACK! "Take that, and this." WHACK!
Jessie was happy. Her ass was getting spanked again with a large metal pizza peel this time. The pain was overwhelming and with every whack Bertram pushed Jessie's pelvis down onto the floor where a boy band action figure was protruding up from the floor and penetrating Jessie's slick pussy. She brought her ass up high, taunting Bertram with it. "Come on Bertram you can do better than that. Put some muscle into it."
WAAAAACCCCKKKK! Jessie's taunt paid off. Bertram was so angry he brought the peel down so hard that it pushed Jessie all the way down to the ground hard. The pins on her nipples were pushed to one side stretching her nipples. And this time the action figure was forced up inside of Jessie.
"OOOOOOOHHHHHHH! Bertram I did not know you cared so much."
Bertram was confused. Did he hit her so hard and knocked all the senses out of Jessie? What Jessie said next really threw him for a loop.
"Please master Bertram can your little pain slut have another?" Jessie raised her ass once again. Bracing herself for another great smack on her ass. "Pleeeeeessse Master Bertram. I will doooo anything for you if you give your little pain slut one final smack."
Bertram was getting aroused now. With Jessie's pleading voice and the way she was waving her ass up in the air just waiting for him to hit it with the peel again had his cock starting to rise. So Bertram hefted the peel up one last time and brought it down hard on Jessie's already warm red ass.
WHAAAAAACCCCK! Into the floor Jessie went. Tears of joyful pain welled up in her eyes as she got back up on her knees. She turned to face Bertram. "Thank you master. What do you want your little pain slut to do first."
Bertram saw the tears in Jessie's eyes glisten as she asked him what he wanted her to do first. He also saw the two colored clothes pins attached to her nipples.
"Come closer slut."
Jessie started to crawl on all four closer to Bertram. The boy band figure that was shoved into her pussy was wiggling around inside her causing her some pain as she crawled over to the heavy set butler.
Bertram moved a few steps backward and sat on the side of his bed and then ordered Jessie to suck his cock. Jessie was happy that Bertram backed further away from her so the action figure inside her could continue pleasing her.
When Jessie had reached Bertram she sat up on her knees again pushing the boy band figure deeper inside her. Jessie reached up to pull Bertram's shorts down when she received a slap on her hand.
"You are a pet. Pets don't use their paws. Use your mouth." Barked Bertram.
Jessie expected this kind of treatment from the kids but thought that Bertram would be above treating her as a pet. But since he wasn't she complied with Bertram's wishes. She bit down on Bertram's shorts and started to tug on. It was harder than Jessie anticipated but she was eventually able to pull the shorts down his legs.
Bertram was not wearing any underware and Jessie saw how gross and disgusting Bertram's cock actually was but she was still craving another cock before she could sleep. So she closed her eyes as she moved in to start sucking this gross fat cock.
Rocking back and forth on Bertram's cock, Jessie could taste how filthy and sweaty the cock was. The tantalizing pain of the action figure in her pussy was helping her forget just how gross and disgusting this cock was. She would also fantasize about the other cocks she had to suck earlier today and it too was making this whole ordeal worth it.
Bertram was enjoying himself. Jessie's warm wet mouth was so pleasing that he stood up and and grabbed Jessie's head and started to face fuck her hard. Bertram pulled Jessie's head onto his cock and then pushed her off. Jessie thought that she might get whip lash from how fast and hard Bertram was using her.
Bertram pulled Jessie off his cock and sat down on the bed again. "That's too much work." Bertram reclined on his pillow.
"Now get up here and ride me cowgirl!"
Jessie figured that Bertram was a lazy slob when they first met and she expected something like this would happen and in truth was hoping that it did. By now Jessie's pussy was so slick that as she stood up the little action figure slipped out of her with little resistance.
Climbing up onto the bed and straddling the overweight butler, Jessie grabbed his member and lined it up with her pussy. She slowly lowered herself onto the fat and disgusting cock. It felt soooo goood sliding up into her that Jessie closed her eyes and savored the feeling. Bertram noticed Jessie's reaction and it turned him on even more and he grew just a little more hard as his cock slid into the red headed pet.
Jessie began slowly bouncing up and down on the butler's cock. Dreaming of the other big and painful cocks that had rammed her pussy earlier that day. Unconsciously Jessie reached up and started to knead her breasts.
"Mmmmmm, Ooooohhh, Oooooohhhhh." Jessie would moan over and over as she was slowly riding Bertram's member.
Bertram was enjoyed watching Jessie fuck his cock and play with her tits, but it was not good enough for him.
Smack! Jessie's sore red ass brought her out of her daydream. "Faster, your master wants you to go faster!"
Jessie's eyes opened up and she looked into Bertram's glaring eyes. "As you wish master." Jessie bent over and grabbed Bertram's tee shirt and started to really ride his cock like a jockey at a horse race.
"Now that's more like it. Oh, yeah!"
Bertram noticed Jessie's breasts moving back and forth as his little slut rode him. He reached up and grabbed both of her tits and started to squeeze them.
"YES, master Bertram squeeze my tits harder PLEASE!"
Bertram complied. Jessie was reaching yet another climax and Bertram's balls began to boil. He started to squeeze Jessie's tits harder and she would slam down hard on Bertram's cock with every painful squeeze.
"OWWW! YEAAAAAAAHHHHHH!" Jessie's loud voice quivered with great pain and pleasure.
"Uuuuuuggggghhhh! Take that you little slut!" Bertram exclaimed as he shot his load into Jessie's gushing wet pussy.
Jessie and Bertram had climaxed at the same time. Jessie shot up into a sitting position when she reached her climax. Her breasts were in a lot of pain, her climax pulled her tits out of Bertram's vice like grip, from his own climax, when she sat straight up.
"That was a good ride my little slut, but you are not done yet. Turn around." Bertram ordered.
Jessie was still enjoying the pain and pleasure of her last orgasm when she heard Bertram order her to turn around. What now? She thought, but complied with his demand. Jessie began to rise off of Bertram's cock when she got a Smack! Her sore ass lit up again and she looked at Bertram.
"Did I say you could get off my cock? Turn around. NOW!"
"Yes master Bertram." Jessie was now beginning to regret calling Bertram master.
Bertram picked up on Jessie's resentment and hesitation so he Smack! Smack! Both of Jessies sore cheeks.
"Owwww!" She squealed.
"Hurry up!"
With Bertram's still hard cock up her pussy Jessie swiveled around.
"Now you can take it out of your pussy."
Jessie removed Bertram's cock. When she did she started to squirt some of Bertram's huge load out onto his balls.
"One final ride. Stick it in your back door and ride it like a stallion! Now!"
"Yes master Bertram." This time she said it with a subservient tone that Bertram liked.
So Jessie slid the fat man's cock into her ass and started to ride it.
Smack! "You like that little pain slut?" Smack!
"OW! Yes master Yes! OW!"
The pain was getting to Jessie now. She started to tear up and cry. She could no longer tell if it was the pain or the pleasure she felt from all of the smacks on her red sore ass.
After five more minutes of Bertram smacking Jessie's ass and Jessie bouncing up and down on his cock Bertram grabbed Jessie's waist and slammed her down on his dick and fired off another round of spunk deep into her bowels.
"Now get out of here! I'm tired." Bertram pushed Jessie off of him. Jessie was still leaking cum out her ass as she stood up and started for the door.
"Wait!" Said Bertram.
Jessie turned around to face Bertram. "I know on all four. I am a pet now." Jessie got down on all four and was about to leave when Bertram spoke again.
"One more thing before you leave. Come here."
Jessie complied.
Bertram sat up in bed and bent over close to Jessie's face and said, "These are mine."
He had swiftly reached around Jessie's arms on both sides and yanked the colored clothes pins off of Jessie's nipples.
"OWWWWWWW!" And the tears started to flow even more.
"Now you can go!"
Jessie still crying slinked up the staircase and into her room where she fell fast asleep