Filling All Cavities Ch. 01 by walterio©

Filling All Cavities Ch. 01 by walterio© INTRODUCTION 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. TOM AND TRUDY HONEYMOON IN SAN DIEGO 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. "Oh my, I didn't think that I could do that. I'll never be the same back there again," Trudy whimpered. They cuddled together and Tom was thrilled that his wife had finally come around and given up her ass. Now he would take her ass anytime he desired it. His arm draped over her body and cupped a breast as they cuddled in the spoon position. They still had five more nights together in their honeymoon. Over the next five days and nights, Tom was relentless with his desire for his wife's ass. He took good care of her pussy but it was her ass that drove him wild. By the end of the honeymoon Trudy's ass had been well broken in and she was receptive to the anal sex. She had also come to love the beads and plugs in her ass when her husband ate and fucked her pussy. AMANDA ACCIDENTLY SPYS ON HER DAUGHTER Tom and Trudy had been married over a year when Amanda first spied on them having sex. It wasn't intentional but it happened. It was a Saturday morning when Amanda was out and she decided to pick up some pastries and lattes at her favorite French bakery. She had thought to surprise Tom and her daughter with breakfast but it was Amanda who was in for a surprise. Amanda arrived at their house and knocked on the door. She waited several minutes but when no one answered she let herself in the house. Amanda had a spare key as did her daughter to Amanda's house. It was obvious they were not up yet so Amanda decided to wait in the kitchen. She heard noise coming from the bedroom and her curiosity got the best of her. She hoped that they were having sex and that she could peek in on them. She quietly walked to their bedroom. The door was partially open and Amanda could see them both on the bed in the mirror on the wall. It was perfect as she did not have to look around the door to spy on them. They were both naked on the bed and Trudy was deep throating Tom's impressive cock. It wasn't long before he came in her mouth and she swallowed all of his cum that she could. Trudy scooped up cum around his cock and her face and licked her fingers clean. She then returned to sucking his cock until he was hard again. Then she lay on her back taking his big dick in her cunt. He pounded her pussy and brought her to multiple orgasms. Amanda was not prepared for the next move, when Trudy flipped over on all fours and waved her shapely ass at Tom. Tom retrieved the lotion from the night table and proceeded to lubricate her asshole. He fingered her ass and pussy at the same time, sawing his fingers in and out of Trudy. His cock was erect again and he covered it with a generous amount of lotion. He then slowly eased his big dick into Trudy's beautiful upturned ass. He fucked her slow at first and then gradually picked up the pace. Trudy pleaded with him to fuck her ass hard and to fill it with cum. Amanda could not believe what she was seeing and hearing from her own daughter. Amanda's own hand had slipped inside her panties and she was frigging her pussy toward her own orgasm something she only did in the privacy of her bedroom. Amanda had gotten lost in her own sexual masturbation when she looked back in Trudy's room and saw Tom looking right into the mirror. Amanda was sure that he could see her as well as she saw him. Their eyes locked on each other's in the mirror and he seemed to enjoy the voyeurism. He then announced he was cumming, almost for Amanda's benefit as he flooded Trudy's ass with another generous amount of man seed. He told Trudy to clean him up as he popped his cock out of her asshole. Amanda was stunned as her slutty daughter spun around and took his cock in her mouth. Amanda watched Trudy sucked him completely dry. Amanda was mortified and quickly retreated downstairs and back to the kitchen. Amanda couldn't believe the display of raw sex that she had just witnessed and how much her daughter loved it. She made a lot of noise in the kitchen so that they would hear her although she was sure that Tom had seen her and knew she was in the house. Minutes later Tom and Trudy came into the kitchen and tom had a sinister smile on his face. "Hi Amanda, what have you been up this morning," he said cockily. "Oh I was out and I picked up some muffins and lattes for us," Amanda said her voice cracking slightly. "How thoughtful of you mom," Trudy said and Tom added, "Yes how thoughtful." Tom could have roaming eyes and that morning he did. He checked out his mother-in-law and admired her ass. For a woman in her fifties she looked good and Tom wondered if she had ever been fucked in the ass. He moved around Amanda to pick up his latte and as he did he let his hand graze over her buttock. Amanda froze at the touch but she didn't move or protest so as not to alert her daughter. She quickly moved to the kitchen table and sat down with her coffee and muffin. After breakfast Amanda left but not before Tom goosed her ass again and whispered in her ear, "Did you enjoy watching your daughter get butt fucked?" That night in her bed, Amanda could not get the images of her daughter's lewd behavior out of her mind. There was something else that haunted Amanda as well and that was the size of Tom's cock. Amanda had never seen a cock that large and that thick before. Of course she had only been with one man and that was her former husband. Her husband's cock paled in comparison to Tom's. Amanda was astonished that her daughter easily handled the cock in her vagina, mouth and ass. Amanda could still see the big shaft sliding in and out of her daughter's shapely ass. Amanda had never had anything in her ass except a doctor's finger and she couldn't imagine something the size of Tom's cock penetrating her anus. Amanda closed her eyes and rubbed her clit as she visualized her daughter getting fucked. TOM SEDUCES HIS MOTHER-IN-LAW It was a week later on a Saturday when Amanda stopped back at Tom and Trudy's house. Trudy was just about to go for a jog when her mother arrived. Tom made no effort to get up from his chair but he did greet Amanda. "Hi Amanda, it's nice to see you again," Tom said and as he rubbed his cock through his pants, he stared at her long and hard taking in her fit figure and shapely ass. "Cocky bastard," Amanda thought to herself before she spoke, "Hello Tom it's nice to see you again too," she replied. Trudy then got her mom a cup of coffee. Amanda would glance over at Tom and each time he would rub his cock through his pants. Amanda couldn't believe what she was witnessing but she found that it turned her on. Tom seemed to know that he was getting to her and he even grabbed his cock a few times. Amanda was flustered and she was blushing at her son-in-law's lewd behavior. Amanda tried to ignore him but her eyes kept drifting back toward Tom. Trudy then said, "I want to get my run in. It will only take about 30 minutes. Hey Tom keep my mom company," Trudy said and then she darted out of the house. Tom smiled at Amanda and he stood up and walked toward her. Amanda froze as he approached her but he walked right past her and locked the door. "We wouldn't want anyone to walk in on us. What would they think?" Tom said confidently. Amanda was nervous being in the house alone with Tom but at the same time found it to be arousing. "You know Amanda I think that it is time that we got to know each other better," Tom said. "I know you have been looking at my cock in my pants ever since you got here. You probably remember it from the time I pulled out of Trudy's ass and shot my load on her buns. I think that you should have a closer look at it," Tom whispered. Tom walked over and stood in front of Trudy's mother and then pushed her to her knees. "Take it out, you know you want to," Tom directed. As if she was in a trance Amanda did as Tom demanded. Amanda's hands were shaking as she hooked her fingers in the waistband of Tom's pants and slowly pulled them down. Tom's impressive cock got caught in the waistband momentarily and then it sprung out like a coiled snake. Amanda gasped when she saw the big cock bob in front of her face. Tom's cock was big but it was not huge. However at 7+" long and a little more than 5" around it was the biggest cock that Amanda had ever seen and it looked menacing to her. She briefly recalled her ex-husband's cock which was more the average size of 6" and not as thick. Amanda just stared at the cock in front of her as Tom kicked off his pants. Tom reached for Amanda's head and held it gently as he guided her face toward his cock. Amanda knew that she was expected to take Tom's cock in her mouth but she was reluctant. Amanda had only performed oral sex on her husband and that was in an effort to get him hard or to get him interested in sex. No one had ever cum in her mouth in her life. Amanda let Tom guide her face to his cock and she opened her mouth wide to receive the impressive organ. The big fleshy mushroom head filled her mouth and she knew that she would never be able to take all of him in her mouth. Amanda was inexperienced in oral sex but she tried to hide that from Tom. She bobbed her head up and down on the stiff shaft taking about half of it in her mouth. Amanda actually liked the soft feel of the mushroom head rubbing against the roof of her mouth as she sucked the thick cock. Tom then held her head gently and caressed her hair as Amanda sucked him. Tom was very turned on and he knew that he would not last long since he and Trudy didn't have sex that morning. Tom's felt his ball sac tighten and the pressure build in his scrotum. He opted not to tell Amanda that he was close to cumming but instead held her head more firmly. Tom felt his release and he ejaculated into Amanda's mouth with such force that it startled her. Amanda tried to pull her head off of Tom's cock but he held her head tightly as jets of cum shot into her mouth. Amanda felt the first jolt hit the back of her throat and before she could react, a second round shot in her mouth. Amanda swallowed the semen as quickly as she could as she had no choice. She didn't want it to land on her dress so she couldn't just spit it out. Tom kept shooting cum into Amanda's mouth and she quickly learned to use her tongue to block the discharging cock before swallowing the semen. Six forceful jets were shot into her mouth and then the cock just oozed its remaining discharge. In spite of her inexperience, Amanda ended up swallowing all of Tom's semen. She at first was repulsed by the act but then she thought that the semen hadn't tasted that bad. Amanda finally removed his cock from her mouth. She stared at the imposing weapon that had just ejaculated in her mouth and it was still as hard as steel. Amanda felt Tom's hands on her pulling her to her feet. Tom put his shorts back on and then he smiled at her and spoke. "That was very nice Amanda; that's enough for now. Trudy will be back any minute now. We will get together at your home the next time," Tom confirmed assuredly. Minutes later Trudy returned from her run smiling, "I hope you two behaved yourselves," she said with a laugh "Oh we got along just fine Trudy, your mom is great company," Tom said as he smiled at Amanda. "Hey, let's all go out for brunch. I'll grab a quick shower," Trudy suggested. "I'm all for it," Tom agreed. Amanda nodded her agreement nervously but the rest of the morning went without incident. Amanda still could not believe that she had sucked her son-in-law's cock and that he came in her mouth. Her pussy was tingling and she knew she would masturbate as soon as she got home. She also knew that it would be difficult to avoid Tom's advances. PURSUIT OF AMANDA CONTINUES Another week of work went by for Trudy and Tom. He was getting busy at the dental office as people were asking specifically for him. He knew he could start his own practice if he could fund it and he would be successful. Trudy went out with her girlfriends on a Thursday night so Tom decided to pay Amanda a visit. He left the dental office at 4:00 PM and headed right for Amanda's stately home. Amanda had just taken a quick shower just to rinse off as she had been sunbathing at her pool. As Amanda was drying off she checked her body out in the mirror and she liked what she saw. She was proud of her figure. She put on her velour lounge wear as she loved the feel against her naked skin. Then she curled up on the sofa with a book and a glass of wine. Amanda's mind drifted back to the incident at her son-in-law's house and she still couldn't believe that she had sucked Tom's cock last Saturday. Her thoughts were interrupted when the doorbell rang. Thoughts raced through her head. Could that be Tom? Oh my God what do I do now? I can't let him in. I can't have sex with him. I shouldn't. "Hey what took you so long?" Tom blurted out when she finally answered the door. "I wasn't expecting anyone," Amanda replied nervously. Amanda turned beet red as she had not expected Tom to show up. Amanda walked ahead of Tom as she moved back into the family room and Tom watched her marvelous ass undulate under the velour pants. Amanda turned to face him and she was about to speak and tell him he really should leave when he stepped up to her and kissed her driving his tongue into her mouth. She had not been kissed that passionately in a very long time. Tom began to undress Amanda as she stood still and trembled as her clothing was removed. Tom first removed her velour top, then her slippers and her pants. Amanda instinctively covered her breasts with her hands. Tom massaged Amanda's neck and shoulders gently as if he was trying to remove her tension. Then his hands encircled her waist and he kissed her neck. Amanda trembled and goose bumps covered her skin. Tom's hands moved upwards and he cupped her breasts. He fondled them gently and toyed with her erect nipples. Amanda could feel her body heating up and she felt like she was a teenager once again. Tom then dropped to his knees behind Amanda and he kneaded her buttocks gently in his hands. Then he lovingly placed kisses on each of Amanda's ass cheeks and let his tongue tickle her crack. Amanda gasped aloud when the tongue slid over her crack. Tom turned Amanda around so that she faced her kneeling lover. Tom touched Amanda all her around her vulva and probed her vagina gently with his fingers. Amanda's pussy was sopping wet by now and Amanda was anxious when Tom moved in closer to lick her pussy. Amanda groaned and shivered as the tongue danced over her labia and then she almost collapsed when the tongue found her clit. Tom pushed two fingers into her pussy and quickly located her g-spot. Then he massaged her g-spot and nibbled on her clit simultaneously. Amanda lost it and she grasped Tom's head and held him tightly as her juices poured into his mouth. Amanda almost lost her balance, her orgasm was so intense and she seemed to cum for minutes. Then Tom stood up and Amanda saw his face coated with her love juice. Tom kissed her again and she tasted herself. Tom guided Amanda to her bedroom and over to her bed and had her lie on her back. Amanda watched him as he undressed and then moved onto the bed with her. Tom raised himself up and knelt between her legs. His huge cock looked menacing as it hovered above her hips. Tom held his cock and lined up the swollen head with the entrance to her sex. He pushed forward slightly allowing her tight cunt lips to open up for his impressive cock. He was about half way in when he pulled out and then slowly eased back into her causing her to moan in pleasure. Tom would push in a little and then pull out a little slowly working his cock deeper and deeper into her vagina. Finally his entire cock was buried in her and Amanda sighed feeling completely full almost afraid to move. This was still a new sensation for her to be this full as his cock touched areas within her for the first time. Tom held himself inside her waiting for Amanda to start fucking him. He looked down at her and smiled as he knew he had her and she would be his from now on. Amanda was ready to be fucked and she needed his big dick to slide in and out of her and rub her clit. She began to move and then Tom fucked her using long slow hard strokes. Amanda locked her legs around Tom's ass and pulled him into her. He began to fuck her harder and faster and she felt another orgasm on its way. She was at the mercy of his impressive organ as it pounded her pussy. Amanda was so hot and she squeezed him with her tight pussy. Tom fucked her through one orgasm after another before he filled her pussy with cum. His orgasm was as intense as hers as their bodies ground together and they moaned and groaned loudly. Amanda felt the warm liquid fill her womb as Tom fired round after round into her. Amanda could feel his cock softening but even then it still filled her cunt. Tom slowly lifted himself off of her body and in so doing his thick cock slipped from her pussy. Amanda felt the void in her cunt as his cock left her body and she gasped as the coolness of the air touched her vacant pussy. Tom rolled Amanda over on her stomach and looked at Amanda's ass and he could not resist running his hands over her shapely cheeks. Her ass was so round and so shapely that he felt his loins stir with desire. Tom got to his knees behind Amanda and kneaded her gorgeous ass cheeks. Amanda thought back to earlier when Tom had kissed her buttocks and tongued her crack. She secretly hoped that he would do that again and she got her wish. He then began to kiss her ass cheeks and run his tongue lightly in the crack of her ass. Amanda wiggled her ass feeling very wicked as he tongued and kissed her. No one had ever done that to her and the feeling was incredibly naughty. Amanda felt that she was truly being made love to for the first time in her life. Tom had no knowledge of whether Trudy's mother had ever been butt fucked but he assumed that she never had. Tom got to his knees behind Amanda and kneaded her gorgeous ass cheeks. He then returned to kiss her cheeks and run his tongue lightly in the crack of her ass. Amanda wiggled her ass feeling very wicked as Tom tongued and kissed her. Tom lifted her by her hips so that her ass was perched in the air. Amanda's head was still on the bed and she turned it to one side and let out a gasp as Tom's tongue licked close to her asshole. Tom ran his tongue from her pussy to her ass causing her to tingle in anticipation of what might be next. Tom spread her ass cheeks with his hands and dipped his tongue into the crack locating her nether hole. His tongue slowly circled her anus and she flinched at the contact. He then pushed his tongue as far as he could into her asshole and he found himself wanting to fuck her up the ass. He continued to ass fuck Amanda with his tongue until she was at his mercy. Amanda's desire grew as Tom worked her ass to the point that she suddenly felt that she wanted something more in her ass. Tom removed his tongue from her ass and ran his hard cock between her ass cheeks as he spoke to her, "I want to fuck you in the ass Amanda. Do you want me to fuck your hot ass? I can see that your ass is asking to be fucked." "Tom no, don't you dare try," Amanda yelled in a panic. "Stay right there," Tom told her as he retrieved a bottle of body lotion from the bathroom. Then he knelt behind her and once again shoved his big dick into her pussy. Amanda was relieved when he put his cock in her pussy. She didn't mind being fucked dog style and it gave her clit a rest. He started to play with her ass again and squirted the lotion in the crack of her ass. He massaged the lotion into her asshole and began to finger her ass. The lotion made Amanda very slick and Tom's finger slid easily in and out of her anus. It was Amanda's first anal penetration other than a doctor's finger. Although it seemed wicked, Amanda found that she liked the finger in her ass while his cock was in her pussy. Then he pulled his cock out of her pussy and let the head rest against her anus. "You want it in your ass Amanda?" She heard Tom say as she felt his cock press against her virgin ass hole, "I want to fuck your hot ass." "No please no!" Amanda cried shaking her head from side to side with her face pressing against the robe covered floor. "I've never done that, you're too big. You'll ruin me." "Don't be silly I'm not going to ruin you. You just need to be stretched a little," Tom said and added, "If your daughter can take my cock in her ass, you certainly can." Tom had gone this far and now he was determined to take Amanda's ass. It was the last frontier for her and besides he loved fucking women in the ass ever since his high school teacher taught him about anal sex. Tom spread plenty of lotion on his cock making it very slick. Then with one steady motion he plunged his cock into Amanda's asshole. He seemed gigantic, long and wide and Amanda screamed as he began to work his way into her poor tight ass. She could actually feel her stomach cramping around him as he stirred her insides and it burned when she clenched her ass muscles convulsing around his thickness. Shaking and sobbing with painful ecstasy, Amanda fell forward onto her pillow with Tom's hands keeping her ass high in the air for him to plunder. Amanda screamed into her pillow as it felt like a hot thick poker had just been rammed into her ass. Tears filled her eyes as her violated asshole spread to accommodate Tom's thick cock. She tried to get away but Tom was too strong and held her in place. Amanda cried out loud only to have the sound muffled by the pillow as his complete length filled her. Amanda felt him flex his cock deep within her bowels as the searing pain continued. Tom reached one hand under her again and teased a nipple. Then he moved his other hand down and rubbed softly against her clit. Amanda's body responded to his stimulus and her stomach convulsed with mixed signals. The intrusion in her ass wasn't as bad as Tom's fingers continued to tease her clit. Amanda felt him move inside her ass now and she tried to relax her ass muscles. Amanda's body was working back and forth on his cock now and she was amazed at the feeling of the cock in her ass. Amanda's clit was buzzing and the fullness in her ass just seemed to excite her pussy even more. Tom started hammering into her ass. His fingers were still busy on her clit but now he had two fingers drilling in her pussy as the others fluttered around her clit. Amanda's whole body was aflame as she could feel his fingers pressing against the thin membrane separating her ass from her pussy. She could feel his hard cock sliding in her and the pressure of his fingers on his cock through her thin membrane. Amanda didn't need Tom to force her on his cock anymore, nor did she need him holding onto her tightly. Her entire body was fucking back at him of its own accord. Amanda could feel an enormous orgasm building within her and her pussy was swollen to new proportions. "Oh God," Amanda thought to herself, "I'm going to cum again, Oh God! I don't want to cum again, not like this, not with his cock in my ass." Tom continued plowing into Amanda. The hot depths of her ass were so tight around his cock she knew that he was going to cum hard too. He worked his fingers faster inside her as he rammed his cock hard into her ass. Amanda started biting the pillow like a mad woman as his groin made hard contact with her ass. Amanda felt her pussy spasm suddenly and then her whole body went rigid. She felt his cock swell in her rectum and then hot spurts of liquid lava hit her deep in her bowels, giving her a cum enema. Amanda screamed into pillow. Both of them shuddered hard as every muscle tensed and then relaxed. Amanda felt a hot explosion as her body was overcome with a violent orgasm. She could still feel Tom's cock throbbing and spurting deep within her. Amanda felt Tom's cock shrink in her ass and then slowly back out making an audible popping sound. Amanda's ass was still high in the air and her thighs were aching. Tom lovingly caressed her shapely ass cheeks. He was proud of himself and his conquest. He had never expected to fuck Trudy's mother in the ass but he couldn't stop once he got started. He was pleased that he was her first ass fuck. Tom backed off as Amanda lay face down on the bed and she refused to look at him. Amanda was humiliated by the act, her ass was on fire and she was embarrassed by her behavior. She was still stunned that she had been fucked in the ass and by her son-in-law. Amanda was ashamed of what just happened and she couldn't even look Tom in the eye. Tom went into the bathroom and turned on the bathtub faucets. Tom located the bath gel and added it to the water. Tom waited until the water temperature was just right and then he went back into the bedroom to get Amanda. Reluctantly Amanda allowed herself to be led into her bathroom to bathe with Tom. Amanda got into the tub and Tom got in with her and got behind her. Tom guided Amanda's body back so that it rested against his and he wrapped his arms around her. "Now let's relax and enjoy the bath for awhile," Tom said as he spoke the first words since taking Amanda's anal cherry. Amanda was still speechless as her mind was cluttered with thoughts. She had never expected things to turn out like they did with Tom. She never expected him to come on so strong and take control as he had. Amanda felt dominated and submissive in the hands of her son-in-law. On one hand she was having great sex and on the other she was scared of the way her body betrayed her. Amanda never knew that she was capable of such behavior. How could she ever face her daughter again? Tom reached up and caressed and fondled Amanda's breasts and toyed with her erect nipples. Her tits and nipples felt particularly good in the oily water. Amanda then felt Tom's cock harden and press against her buttocks. She knew that she was in for another round of sex but she had no idea what he had in mind this time. They soaked in the tub for almost and hour with Tom caressing Amanda's body before they finally got out and dried off. Tom dried off Amanda's body and then she dried Tom. Tom's cock stayed hard the entire time that Amanda dried him off with a fluffy towel. Amanda let her hand brush against the erect cock several times and she enjoyed watching it twitch each time. All of a sudden the cock did not look so menacing although it was still hard to believe that something that size had been in her ass. Amanda had a strange desire to take the cock in her mouth again and she dropped to her knees in front of Tom. Tom was pleased when Amanda wrapped her lips around his cock without any urging from him. Amanda sucked the cock deep into her mouth and tested her gag line seeing how much she could take in her mouth. She then fondled Tom's balls and she was pleased when he groaned with pleasure. Amanda closed her eyes with her lips snugly wrapped around his shaft as she bobbed back and forth. She was incredibly turned on and her pussy was soaked again. Tom brought excitement into Amanda's life with his cock and she would now be addicted to it. Amanda was so enamored with his cock that she discovered she loved to suck on it. Amanda was happy to please Tom again and to make him cum. Amanda wanted this to be Tom's best blow job and she put all her efforts into it and it did not take her long to bring Tom to the edge. Tom this time announced that he was cumming but Amanda clamped down on his cock as she was determined this time to swallow every drop of his seed. She could feel his cock jerk in her mouth as volley after volley bounced off the back of her throat. Amanda swallowed as quickly as she could and did not allow a drop to escape her mouth. She continued to suck on his cock milking it dry of his sperm. Then Amanda took the cock from her mouth and Tom watched as she squeezed more cum out the end of his dick. Amanda then wrapped her lips around it and sucked his man juice dry. Tom never expected this behavior from Amanda but he loved it. She nibbled on his dick head causing him to shiver and he had to push her away. Tom's cock stayed hard though and Amanda marveled at the impressive organ before her. Tom reached down and lifted Amanda to her feet and then he kissed her deeply again showing her that he was unconcerned that he had cum in her mouth. "I think this would be a good time to discuss my future as a dentist. I have enough patients that I know my practice will be hugely successful. I need some financial backing to get started and you are just the person to help me out," Tom announced. "I see and what kind of financing will you need? What kind of a return will I receive for my investment?" Amanda asked somewhat surprised by the request. "I will apply for a SBA loan but I will need you to cosign as collateral. I should be able to pay you back for any upfront money within two years. The best part is that you will have access to my cock whenever you like," he told her. Amanda lay back on the bed and displayed her beautiful neatly trimmed pussy to Tom. Amanda felt a glow about her and she was now openly proud of her body. She opened her legs and smiled at him leaving no doubt as to her desire; her pussy for his taking. "You mean like now?" she said sexily. Tom knelt before his mother-in-law at the end of her bed and kissed her from her knee up her soft thighs towards her womanhood. He took in the lovely smell of her as he kissed her smooth creamy white skin just beside her vagina. Amanda was in a state of ecstasy and her heart pounded as she watched Tom lick her. Her cunt lips quivered as he teased them with his tongue and kissed her everywhere she desired. Tom's tongue was long and probed deep into the inner walls of her pussy Amanda ran her hands over her body cupping her breasts and rolling her nipples between her fingertips. Tom sucked her cunt lips into his mouth as his tongue snaked around in Amanda's snatch. Tom still had not made contact with her clit and Amanda desperately needed his tongue or his cock to touch her clit. She moaned in pleasure and frustration as Tom continued to tease her. He again wiggled his tongue deep within her pussy before finally nudging her clit. Amanda jumped as a spark of pleasure shot through her body. Tom slid his hands under her curvy ass and lovingly cupped Amanda's shapely ass cheeks. He sucked her clit into his mouth and held it between his lips as he ran his tongue over the large hard pearl. Amanda arched her back as she felt her orgasm approach. "Oh yes, oh my," she called out as the first wave rocked her body. Amanda grabbed Tom's head with both hands and pulled his face harder into her crotch. She vigorously humped his face as his tongue danced over her super sensitive cit. Her thighs clamped around his head and her entire body trembled as she came again almost violently. Amanda felt her pussy pulsating as she covered Tom's face with her female juices. Finally she collapsed back on the bed releasing him in the process. "Oh my God," Amanda moaned. Tom raised himself up and knelt between Amanda's legs. His cock looked imposing as it hovered above her hips. "Are you ready for this Amanda?" he asked smiling confidently. "Oh yes, yes please, fuck me now," Amanda pleaded. Tom held his cock and lined up the swollen head with the entrance to her sex. He pushed forward slightly allowing her tight cunt lips to open up for his cock. He was about half way in when he pulled out and then slowly eased back into her causing her to moan in pleasure. Tom would push in a little and then pull out a little slowly working his cock deeper and deeper into Amanda's vagina. Finally his entire cock was buried in her. Amanda sighed feeling completely full and almost afraid to move. Even though Tom had fucked Amanda before she loved the sensation each time he entered her. Tom held himself inside her waiting for Amanda to start fucking him. Amanda was ready to be fucked and she needed his dick to slide in and out of her and rub her clit. She began to move and then Tom fucked her using long slow hard strokes. Amanda locked her legs around Tom's ass and pulled him into her. He began to fuck her harder and faster and she felt another orgasm on its way. She was at the mercy of his rigid organ as it pounded her pussy. If Tom hadn't just cum in her mouth he would not have been able to hold on as long. Amanda was so hot that she squeezed him with her tight pussy. Tom fucked her through one orgasm after another before he finally filled her pussy with cum. His orgasm was as intense as hers as their bodies ground together and they moaned and groaned loudly. Tom fell forward but he kept his weight off of Amanda. They were both breathing rapidly and deeply. Tom remained in that position for several minutes until he could feel his cock softening but even then it still filled her cunt. Tom slowly lifted himself off of her body and in so doing his cock slipped from her pussy. Amanda felt the void in her cunt as Tom's cock left her body and she gasped as the engorged member vacated pussy. Tom eased himself off of the bed and smiled down at the well fucked Amanda. She seemed powerless to move and she remained in bed when Tom dressed and left the room. Amanda felt the discomfort in her rectum and she wondered if she would ever be the same after that day. She did not like having a cock in her ass and it had hurt like hell. However she had to admit that when Tom came in her ass the warm cum did soothe her ravaged rectum. Before he left the house he reminded her that he would be in touch regarding the finances. NEXT CHAPTER Tom starts his own dental practice and hires a hot hygienist and receptionist. Trudy starts to explore other men knowing that Tom is banging other women. Amanda is hooked on Tom's bedroom talents.