The First Officer moved behind her, pushing down on her back, forcing her to bend over the wooden barrel, the wooden phallus inside her. “Tie her down,” he ordered the men, watching as they eagerly complied, their hands roaming over her naked body as they did. He enjoyed the way her ass arched up, seeing the wooden cock inside her pull out slightly as she was forced to bend over.
“GGGOOOD,” she cried out in pain when they bent her over. The unyielding wooden phallus refused to yield, pushing painfully against the sides of her pussy as she bent over, stretching her wider than she thought ever possible. It felt as if it were twice the size, her pussy lips tugging and tearing as it sought to accommodate the monster. The pirates flocked to her body as they tied her down, hands reaching under to tug on her nipples, crush her tender breasts in powerful hands, even yanking her pussy lips apart. The ropes tightened, pinning her painfully over the thick cock embedded inside her, her ass pushing up, feeling her anus spreading open. Now for the painful part, as if the rest wasn’t bad enough. Any cock inside her asshole would be painful, but with the wooden phallus inside her pussy, she would be stretched even wider, full of fake and real cock.
The First Officer hands roamed over her up-thrust ass cheeks, pushing down on the marks left by the whips, her body jerking in pain, cries from her as she was forced to buck on the wooden cock. His fingers went to her anus, teasing the tiny hole with his fingertip, rubbing it as it began to spasm from the unnatural probing. “Bring me the funnel.” He was quickly handed the funnel and the bottle of oil. He pressed the large hole on the end of the iron funnel against her anus. “Open for me Gretchen. Open and I will lube you to ease the entry of my cock.”
She felt the sharp edge of the iron against her anus, shuddering as she fought her anal contractions, afraid he would tear her with the sharp funnel. She pushed back on her muscles, feeling her anus flutter open, embarrassed at having to perform for him. She was afraid of pushing too hard, afraid of humiliating herself if she accidentally had a bowel movement.
“Look at the way her tiny hole opens for me,” pushing with the funnel against the darkness of the hole opening, her anal ring opening wide around the iron until it engulfed the edge of the funnel. “Good girl,” tapping her lightly on her naked cheek as if he were rewarding his favorite dog. He pushed with the funnel, slowly sinking inside her until about an inch of cold iron was inside her, leaving her dark hole open. He took the bottle of lubricant, a thick creamy fluid that seemed to pour out of the bottle reluctantly. It hung from the edge of the bottle until it fell inside the funnel, running down in a continuous strand. He emptied half of the bottle inside her.
Her anus burned from the unnatural stretching, her anal ring spread wide around the wide iron lip of the funnel, her sphincter muscles fighting the intrusion, spasms racing through her backside. She felt so embarrassed. She could only imagine how she must look, her legs spread painfully wide, her pussy cramping from the thick phallus bent impossibly inside her, her ass thrust up as if she were offering her backside for his sexual gratification, an iron funnel pressed inside her anus, lubricating her insides for the sodomy that was forthcoming. “Please, don’t,” she cried out as she felt the strange feelings inside her anal tract, a tickling almost as the thick lubricant slid slowly inside her. At least she felt a temporary relief when the funnel was pulled from her anus, her anal ring clenching painfully as it sought to close.
She felt the finger return, this time slick with lubricant, Gretchen struggling as she felt it press against her anus, the sharp fingernail pressed against her intimate hole. “AAAGGH,” she cried out as her anus was suddenly impaled on the thick finger, thrust inside her with such a powerful force that it didn’t stop until his knuckles banged against her tiny hole, the thick finger sliding along her lubricate back passage. Her rectum clenched and unclenched on the offending digit, her stomach already cramping from the unnatural probing of her bowels.
“Such a hot, tight asshole Gretchen, I can feel your muscles gripping my finger in pleasure. My cock is going to delight in such delicious clenching.” He moved his finger inside her, twisting and turning the calloused finger, feeling her jerking at being probed so intimately. His finger slid out, her muscles pushing out as he did, seeing her slick, brown wrinkled hole spasm even after his finger had left. “It will hurt less if you push back and let my cock inside your hot, little asshole.” The First Officer hefted his cock up to her anus, rubbing the lubricant up and down the thick shaft until it glistened in the light, the massive weapon hard and imposing. He pressed against her tiny hole, the thick helmet covering completely the opening.
She could feel it throbbing as he pushed against her anus. It was so hard and hot, jerking in excitement as it sought to breach her intimate hole and thrust painfully up her backside. She already felt so stuffed, the thick, wooden phallus shoved inside her pussy, Gretchen trying hard not to move. When the finger slid inside her she jumped from the unnatural probing, the wooden shaft rubbing her pussy raw with the thick head, Gretchen bucking, finally able to control her own body, suffering the rude probing of his finger in order to spare the painful rubbing inside her pussy. “Please sir, go easy.” Gretchen begged, hoping he would spare her the painful tearing. She pushed out on her anus, straining, fighting to stop from having a bowel movement, but hoping to aid the First Officer in the sodomy. She felt his hands on her hips, gripping her tightly, holding her breath as she knew he was ready.
He felt her strain to open her tiny hole, his hands holding her tight as he began to push. He felt her anal ring slowly flower open as his slick monster began to push inside. His fingers went to her cheeks, spreading her open so he could watch as he penetrated her, his hips pushing harder as his cockhead began to enter. Her hole slowly engulfed the head of his cock, sharp gasps from her lips as she suffered painfully beneath him. He saw her anal ring stretch until it was almost white, surrounding his cockhead, gripping it tightly just under the rim as she screamed in pain. He stopped, making his cock jerk in excitement as he felt her rectal muscles squeezing the spongy head, trying to force it out. “I’ve never felt such a hot, tight hole Gretchen. You are going to give me so much pleasure with your asshole.”
Stefani heard Gretchen’s hushed screams of pain through the Captain’s hands clamped tightly over her ears, forcing her head up and down on his rampaging cock, spearing her lips as though it were her pussy, using her mouth for his pleasure. He kept choking her, shoving his cock to the back of her mouth, forcing her deeper until she coughed and gagged, tears running down her cheeks. He would relent and pull out, only to push back in again until she gagged on the thick helmet of his cock. His hands continued to pinch and pull her nipples, the tips now red and sore from the abuse, hard and sensitive to his calloused fingers. The cock seemed to grow longer each long minute he used her mouth, her lips stretching wide to accommodate the thick shaft. It plunged in and out, his hips forcing her to take it as deep as he wanted, his hands holding her head submissively for his pleasure.
“GODDDD, go slow, it hurts so bad,” Gretchen groaned in pain as the First Officer began to stroke his cock inside her clenching asshole. How could he do such a thing to her? Forcing his cock inside a hole that was not meant to accommodate such a massive weapon, built to push out, not in. It turned her stomach with painful cramps each time he went too deep, his cock breaching her colon, slowly stretching her insides to take the thick cock. He would push too hard, banging into the sides of her anal tract, the excruciating pain shooting to her brain. It only made it more enjoyable to him, her body tightening up in pain, clinging to his cock. The hard, wooden phallus inside her rubbed her raw, Gretchen unable to control her own movements, the cock in her ass making her jerk in pain as the First Officer rode her hard. It felt as if he were coming out her mouth each time he thrust in, each time his cock touching places that were previously untouched, places that should never be touched.