tagAnalFilling All Cavities Ch. 01

Filling All Cavities Ch. 01



Tom Castle had become a successful dentist with a private practice in southern California. His success in large part was due to his skills as a dentist but what jump started it was the financial backing of his mother-in-law Amanda Collins. Tom was 36 years old in 1965 right in the middle of the sixties sexual revolution. It seemed that everyone was having sex with anyone they wanted and Tom was no exception. In 1960 he married his wife Trudy Collins and in three years they began their open marriage.

Tom was a handsome man who stood at 6'2" and weighed a fit 190 pounds. He had short light brown hair and hazel eyes. He stayed in shape using his home gym and swimming laps in his backyard pool. Trudy was a true California girl with long blonde hair and blue eyes. She was 5'6" and weighed a trim 120 pounds. At 30 years of age she was striking in her bikini showing off her 34-24-35 figure. Trudy had great legs and a marvelous ass.

Amanda, Trudy's mother was no slouch at age 52 and she often showed off her figure at Tom and Trudy's pool. She had a shapely 34-28-36 figure and she too had a dynamite ass. She was 5'5" tall and weighed and respectable 135 pounds. Her hair was blonde which kept short in a DA style and she had bedroom blue eyes. Amanda had been divorced for ten years and she had made out quite well due to California law.

After dental school, Tom joined a large dental group. He established a reputation as an excellent dentist and then with the financial support form his mother-in-law he opened up his own practice. During the years leading up to 1965, Tom had become addicted to anal sex. It began in high school when he was 18 years old. He had sex with one of his teachers and she introduced him to anal sex. He loved it and after that he always tested the water with his dates to see if they would give up their ass to him. His high school girlfriend Susan did and they had anal sex all the time.

In college Tom always pursued girls with nice asses and many of them allowed him to fuck them in the ass. He was relentless in his pursuit of a fine ass and it seemed that he would never be satisfied. After college he attended dental school and the anal pursuit continued. Some of his colleagues used to joke saying that he was filling the wrong cavities. For Tom however there was no better cavity to fill.


In 1960 Tom married Trudy Collins a girl he had dated for several years. It surprised many that Tom married as he always seemed to be one who wouldn't ever settle down. It spite of Trudy's killer ass, Tom had never fucked her there. She loved his impressive 7+ inch cock and enjoyed playing with it and sucking it. Trudy was great in bed and she gave fantastic blow jobs but she didn't show any interest in anal sex. Tom didn't push it as he was getting his share of anal sex without Trudy's knowledge.

They honeymooned at Del Coronado for a week after the wedding. The first night they were in bed and after a great session of love making Trudy said, "I'm a little disappointed that I didn't have my virginity to give you tonight."

Tom replied, "But you are still a virgin in one of your cavities and I would love to take that."

"You mean my ass," Trudy questioned.

"Yes, of course your ass, it's beautiful and I would love to fuck you there."

"Won't that hurt?"

"At first a little but once you are stretched out it won't."

"I don't know. It's scary and naughty."

"I will take my time and make sure that you enjoy it. I brought some things along with me just in case you were agreeable."

"What things?"

"Some anal toys that will bring you pleasure and loosen you up for my cock."

"Oh my God, where are they?"

"In my suitcase, I'll get them."

Tom got out of bed and took out the items from his suitcase. His cock was hardening just from the thought of taking his wife's beautiful ass. He returned to the bed and he saw Trudy's eyes take in his stiff cock.

"Wow, you got hard just from getting those things."

"No, I got hard thinking about your scrumptious ass."

Tom placed the items on the bed and Trudy stared at them. There were two sets of anal beads and two butt plugs. One set of beads was thicker than the other and one butt plug was larger than the other.

"What do you do with these things?" Trudy asked nervously.

"The anal beads go in your ass and when you begin to orgasm they are pulled out slowly. The butt plug goes in your ass and helps loosen you up. Of course a lubricant is used to make the penetration easy."

"Can we stop if I get scared or I don't like it?"

"Of course I would never hurt you. First however I am going to douche your bottom and make love to it before we start with the beads."

Tom and Trudy showered together and he used her douche to get her anus squeaky clean. Trudy was a little turned on by having her ass douched as it was something she had never done to herself. Although it felt good and a bit exciting, she was still apprehensive about her ass. They got out of the shower and dried off. Then Tom led her back to the bed. Tom watched as she crawled n and got on all fours. Before Tom began he stood behind Trudy and took in her marvelous ass, so round, so shapely and so beautiful. Then as Tom knelt on the bed he noticed Trudy's face aglow and her eyes wide in anticipation.

Tom began to explore her ass as he began to caress it, massage it and rub her cheeks. He pulled her cheeks apart slightly and revealed her sweet tight aperture. Then he ran a finger over her sensitive little bud and watched it quiver when he touched it. Tom then lowered his head and planted soft tender kisses all over her buttocks. Trudy cooed aloud when she felt his lips on her backside.

Tom placed both hands on her ass and began to massage her buttocks again. Trudy felt the tender but firm deep massage of his fingertips. Tom would push her ass cheeks together and then pull them apart to expose her sweet asshole each time. When he exposed her anus, Trudy could feel the cool air on her rosebud. Tom again lowered his mouth to one of her buttocks and pressed his lips against it. Then he blew a steady breath onto Trudy's anus and watched as goose bumps covered her skin.

He took his time planting well placed kisses on her buttocks and then began a slow torturous journey toward the crack of her ass. Trudy smelt so nice and so fresh. Tom's lips then came into contact with the crack in her ass and trailed a line of kisses down to her anus. Trudy's body tensed as she was nervous, anxious and excited all at the same time.

Tom gently pried her cheeks apart wider exposing her nether hole even more. Then he lowered his lips to her anus and gently kissed it and caressed it with his lips. He repeated this act several times and Trudy moaned aloud as her ass was pampered for the first time. Tom then moved lower and kissed the sensitive spot between her asshole and her pussy and Trudy groaned again. He then extended his tongue and lightly licked the sensitive area as he continued the journey toward her pussy. Trudy flinched at the first contact with her pussy as she was unprepared for that. Tom then began to lick a line from her pussy back to her asshole and then he flicked his tongue across her nether hole. Trudy's body gave in to the incredible erotic sensations and craved more attention.

Tom took his time and spent many minutes repeating the actions that seemed to turn Trudy on. His hands continued to massage her fabulous globes while his lips and tongue explored her asshole. Her body would twitch and flinch at the long strokes from his tongue and her buttocks would tighten when his tongue probed her anus.

Trudy lay on the bed and she could feel her heart racing and her chest pounding. Tom then leaned over and whispered to her again and told her how beautiful she looked with her ass pushed up high in the air. Then he began to explore her with his fingers. He placed his index finger on her tailbone and slid it down ever so slowly toward her puckered asshole. He probed gently with the tip of his finger and it fit perfectly in the entrance of her tight hole.

Trudy tensed up at first and tightened her ass but then she relaxed when she realized that he was going to be gentle. Tom pressed his finger in gently applying a little pressure as his finger entered the outer edge of her anus entering it just ever so slightly. Then he probed a little deeper and wiggled inside Trudy's ass. He then removed his finger and Trudy felt its absence. Then she felt a cool substance on her anus and she realized that Tom had applied some sort of lubricant to her ass.

Trudy felt Tom kiss her ass cheeks again and then his finger returned to her asshole and spread the lubricant around the entrance. Trudy felt her asshole pucker up as it received the tip of Tom's finger and she wondered how it would feel when he finally put it in her. Her body ached with desire and she realized that she wanted more. She wanted to be touched, penetrated, and filled up and to be explored in her forbidden area. Tom's finger slid in deeper and Trudy instinctively clamped her asshole around his finger. Tom held still in her and waited for her to relax before probing deeper.

Tom then wiggled his finger back and forth and let it slide out slowly to the first knuckle. Trudy felt his finger slide out and she instinctively clamped her ass around it again, this time to hold it in place. Tom could feel her anal muscles clench his finger as if she were milking it and nursing it. Tom knew the battle that was going on within her body. The sphincter was designed to push things out not pull them in. Each time Trudy relaxed her asshole, Tom pushed his finger in deeper until she clamped around it again. This process continued until he entire finger was buried in Trudy's ass.

With his other hand Tom continued to pay attention to the rest of her ass. His hand wandered all over her shapely buttocks massaging and caressing her soft skin. At the same time he continued to slide his finger in and out of Trudy's asshole and he enjoyed watching her anal muscles grip his finger each time. Trudy's breathing had become labored and she began to rotate her ass in tiny circles as if to get the finger in deeper. Tom was in no rush as this is exactly what he had planned. He wanted Trudy to enjoy every moment of the anal sensations. He wanted to work Trudy into a state that she would beg him to fuck her ass. For now though he was content to worship and devour her hot luscious ass.

Tom then lowered his face to her ass and licked her as he probed her with his finger. He took his other hand and reached under her to find her pussy and her clit. As soon as Tom made contact with Trudy's hot wet pussy her body trembled as a wave of pleasure passed through her. Tom was very skilled at finding a woman's g-spot and he located Trudy's instantly. Between fingers rubbing her g-spot, another diddling her clit and a third finger in her ass, Trudy groaned loudly and her body shook with desire. She knew that she was close to her first orgasm.

Tom's two fingers in her pussy matched the rhythm of the finger in her ass Trudy could feel all the fingers in her separated only by a thin membrane inside her. Tom pumped his fingers in and out and Trudy went wild. Tom could feel her body giving itself over to him. It was his now to do as he wished. Her pussy was dripping wet, her ass clamped tight around his finger and her hips pushed back at him but Tom did not want her to explode just yet.

Tom suddenly removed his fingers from her holes leaving her empty. Trudy screamed for him put them back in her, to fill her up again. Her eyes were wide open and she had a wanton look on her face. Her body was begging to be fucked but Tom was in no hurry. He enjoyed this moment and he savored her dilemma. Tom loved doing this to a woman, teasing her and prolonging her climax. He wanted Trudy's anticipation to last as long as possible.

Tom then lowered his lips down to her hot ass and planted kisses all over it again. He massaged the smooth white flesh of her ass as he kissed it and Trudy cooed. She longed for his fingers to be back in her. Tom moved his mouth directly over her anus and blew on her nether hole. Trudy thrust her ass back into Tom's face as if to impale her ass on his tongue. Tom needed no further encouragement and his hands spread her ass open wide so he could probe her asshole. Tom stiffened his tongue like a tiny dick and probed Trudy's asshole. He poked his tongue in and out of her ass then he covered her ass completely with his mouth and sucked hard on it. Tom began to lick, nibble and tickle the sensitive rosebud and Trudy cried out in passion.

"It's time for the beads," he whispered harshly in his excitement.

Tom greased up the beads and one by one he pushed them into Trudy ass. She felt the intrusion but no pain. She just felt full. Tom returned to licking her clit and fingering her pussy and Trudy was going wild. She desperately needed to cum and Tom sensed it.

"Are you ready to cum, Trudy? Do you want me to make you cum?" Tom teased her.

"Oh God yes, please make me cum, let me cum," Trudy screamed back.

Tom reached under her again and located her clit. Trudy's pussy was sopping wet and Tom knew she was very close to a climax. He played with her puffy pussy lips as she diddled her clit and then he pushed first one, then two and finally three fingers into her pussy. Trudy gasped and swallowed hard at the new invasion in her ass as her sphincter seemed to clamp down on the beads.

Tom now had three fingers in her pussy as he picked up the rhythm. The thrusts became deep and hard as he relished with the delight of her pussy with his fingers. Trudy responded by pushing her ass back against his hands as she fucked back at them.

"That's it Trudy, fuck back, fuck my fingers," Tom called out to her.

Tom finger fucked her pussy as Trudy pushed back against him. Tom was getting carried away and he began to furiously fuck her lovely hungry body with his fingers. Sensing that she was close Tom pulled the beads out of her ass slowly. Then it happened and Trudy exploded. Her body jerked as each of the five beads was pulled out of her ass. She clamped down on the fingers in her body and her pussy spasmed as a massive orgasm rocked her. Trudy screamed out loud with her mind blowing climax. Tom pulled the last bead from her asshole and replaced them with his mouth.

He could feel the hot moisture in Trudy's pussy as it coated his fingers. Tom continued to lick her quivering asshole as her first orgasm subsided. Next Tom took the smaller of the two butt plugs and pushed it into Trudy's anus. He flipped her over on her back and filled her pussy with his stiff cock. Another orgasm rocked Trudy's body. This one seemed even more intense than the first and it caught her by surprise. Tom lifted himself up and looked at his beautiful wife. She had a look of pure lust and ecstasy in her eyes.

Tom turned Trudy over and pulled her hips up. Her head was turned to the side and her long blonde hair was draped over it. He got back in bed and caressed her curvy ass again. Yom then pulled the anal plug out and watched as her anus dilated. He whispered to her.

"I am going to fuck you in the ass now. I can see that your ass is ready to be fucked."

"Tom, I'm not sure," Trudy said nervously but she knew she had come this far and Tom would not take no for an answer.

Tom poured more lubricant on her ass and worked it into her asshole. Trudy arched her back and pointed her beautiful ass back at him. He coated her asshole with a generous amount of oil and slid his thick finger back in her hole. He took his time preparing her ass relishing every moment. He then coated his entire cock with the oil and placed the head at the entrance to her anus. Tom pushed forward and the thick cock head squeezed into Trudy's tight asshole. Trudy was glad that she was stretched out using the beads and anal plug.

Trudy winched in pain as her asshole was stretched wider than it ever and she gasped, "Go slow let me get used to it."

Tom withdrew his cock head and then pushed it back in this time causing more pleasure than pain. He pushed until a couple of inches were in her ass. Trudy was holding her breath and her body was covered in goose bumps. Tom was so thick that her asshole stretched to new dimensions and held his cock in a vice like grip. Tom slowly slid his dick in and out of her each time going a little deeper. Trudy pushed back as if she were trying to poop as she knew that would make the penetration easier. Trudy's brief pain had subsided and it was replaced with a feeling of fullness.

Trudy relaxed a little and then felt more of Tom's cock slide into her asshole. She grunted out loud as she felt fuller and then a wave of pleasure passed through her body. She was convinced that Tom had his whole cock in her now but really he only had about half of his big dick in her. She felt so full so had no idea that he had about another four inches before he was done. Tom kept adding more and more of his cock to her ass. There was discomfort then fullness and then pleasure each time he went deeper. Trudy would tense, relax and then enjoy it. This pattern continued until Tom had his whole cock buried in Trudy's ass.

Tom reached around and played with her clit as he pounded her ass. Her pussy and asshole were on fire as the big cock reached previously untouched areas in her body. Trudy was on the brink of another huge orgasm as Tom methodically fucked her in her tight anus with his sizeable cock. He loved watching his cock slide out of Trudy's shapely ass and then plunge back in as his hips slapped against her curvy ass cheeks causing them to jiggle with each thrust. Her orgasm surged within her as he fucked her ass harder and faster.

As Trudy came and came her entire body went into spasm. Her pussy convulsed and clamped around Tom's fingers coating them with her cunt juice. Trudy's asshole pulsated as Tom drove his big cock in and out of it. Her ass involuntarily squeezed and released his huge member as he fucked it causing him to finally lose it. Tom slid his pecker deep into Trudy's rectum as his cock spasmed and sent a thick stream of hot cum into her channel. Tom kept fucking her as load after load was fired into her ass. His cock kept twitching and spurting inside the impaled Trudy.

Trudy had never felt so full of cum and there was no where for it to go, blocked by Tom's swollen cock buried in her ass. He slowed his pace and eventually stopped allowing his cock to remain buried in Trudy's ass. He did not go soft right away and he gently moved his hips pushing cum around in her ass. Some of it trickled out and ran down over her pussy lips.

Trudy could not take any more fucking and she pleaded, "Please no more, I can't take any more Tom, please stop."

Reluctantly Tom stopped and slowly withdrew his cock from her loosened asshole. He marveled in the sight of his impressive cock sliding out of Trudy's shapely ass. His man seed flowed from her asshole and ran like a river down over her pussy and between her sweet thighs. Tom and Trudy stayed in the same position for awhile and he massaged her beautiful ass as she remained on her knees with her ass perched in the air. Tom pushed down lightly on Trudy's back causing her to accentuate her ass even more. He loved looking at it and playing with it as she cooed into the pillow. Tom's cock remained hard and looked menacing around Trudy's asshole. It was hard to believe that he finally fucked her beautiful tight ass. Trudy looked magnificent with her just fucked curvy ass in the air. Tom could not resist sticking one of his fingers in her asshole and she just wiggled her bum instinctively.

"See you did have your virginity to give to me tonight, your anal virginity," Tom whispered as he cuddled with her.

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