Tom’s Journey Ch. 03
Eki 16, 2023 // By:analsex // No Comment
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Missy was a petite, confident woman fresh out of high school. She had shorter, brown hair with blonde highlights caused from spending time outside in the sun. Her skin was silky smooth and brown. She had cute eyes and a laughing mouth. Being out in the sun all day on weekends meant Missy was used to wearing a bikini — and had the body to go with it. Her B cup boobs fit nicely into her bikini top. Below them was a perfectly flat stomach that fitted neatly into a small waist and smooth hips. Her best feature, however, was her ass. It was tight, perky, bubbly, and had every guy (and a few girls) checking it out when she walked down the street. Missy was smart but hated school. She would much rather have fun. By contrast, her friend, Karen, was studying to be a biologist.
The door slammed and Tom knew that his wife was home. “Tom!”
“What dear.” Tom said.
“There is this girl I work with that is a little flaky. She is going to have a party at her apartment. I think someone should be there to keep an eye on things.”
“OK, well, have fun then.” Tom said.
“No, I’m leaving town for a few days to visit my grandma, maybe you could check in on them?” Tom’s wife replied.
Tom sighed. His wife spat, “After what you did to my best friend I think you’d better do what I want or we will be getting a divorce!” and with that she stomped away.
“Stupid Sarah!” Tom thought. Sarah had waited for years before telling his wife what had happened. Of course, she had only told her wife about what Tom had done to her, not the parts where she had ‘thanked him’ for all of his help. When he told his wife about that, his wife just shook her head and told him lying wouldn’t save him. So, he was now cut off, had a massive case of blue balls, and had to go supervise this stupid party in this stupid apartment with stupid kids. “Sometimes I just hate my life.” Tom muttered.
Friday evening came and Tom drove to the address. When he arrived at the apartment complex he immediately recognized it. This was where he had stayed years ago when he was going to college. He looked at the piece of paper in his hand that had the room number. His hand shook a little bit. “It couldn’t be.” he thought. When he got to the room there was no denying it. It was the same room that Tara and Emily had occupied. He flashed back to Emily’s gorgeous face bobbing up and down on his cock, Tara’s screams of delight as she rode him to orgasm, and that amazing throat fuck he had with Emily.
Missy heard someone knocking and bounced to the door. When she opened it a really nice guy was standing there, looking somewhat confused. “Is this where I can find Missy?” he asked.
“That’s me, who are you?” Missy said.
“I’m supposed to supervise this party, I guess. My wife said that Missy was her co-worker.”
“Oh! OK she told me you would be here. Come on in and make yourself comfortable. By the way, this is my friend, Karen.” Tom shook hands with Karen who had on a red, form fitting cocktail dress. She looked uncomfortable in it though, as if that was the first time she had worn anything sexy in her life. Karen had short black hair, a pretty face, glasses, large boobs for her small frame, and a cute waist.
The party went on for a while and soon some of the guests had left, and some of them had passed out. Missy had been in her room for a while with some guy. Karen was passed out on the couch. Tom was sitting in the chair, remembering the times he had had in this place. After Emily had conceded to Tara that she was the biggest flirt, Tara had decided that Emily needed to be punished for her conniving behavior. She said for the next week she and Tom would get to use her in whatever way they saw fit. That week Tom didn’t remember how many times he had cum. Every morning he woke up to Emily’s bright blue eyes staring at him as she sucked his cock. Every evening he would hear Emily’s cries as Tara fucked her with a variety of dildos and strap-ons. When Tara was done playing with Emily Tom would move in for round two and use her pretty blonde body as his cum dump.
All this reminiscing bayrampaşa eskort was getting Tom hard. He looked at Karen passed out on the couch. “No, I couldn’t.” he thought “It’s one thing to get some head and fuck my wife’s friend’s boobs, but it’s another to fuck a sleeping girl.” Thinking of Sarah’s boobs got Tom even harder and hornier. He didn’t hear anything coming from Missy’s room. “She must be asleep.” he thought. He moved over to the couch and cupped one of Karen’s boobs in his hand. “Just one little touch.” he whispered to himself. It was firm and full. Tom fondled the other one. Soon he knew he had to see them. He slowly pulled down the top of Karen’s dress. Her tight boobs sprang into view. Tom paused and listened again. No sound. He rolled Karen’s nipples between his finger and thumb and was rewarded with a slight moan from Karen. Tom kept on playing with her boobs until Karen’s mouth began to sag open and her breaths came out in ragged gasps.
He moved to her legs that were partially hanging off the couch and slipped her dress up above her hips. He hesitated for a moment, thinking that maybe this was going to far. Then he remembered hearing Missy’s cries of delight just an hour ago, and imagined her taught body writhing in ecstasy. He moved Karen’s panties to the side and ran his tongue up her slit. Karen shifted slightly but still remained completely passed out. Now was his chance. Tom dropped his pants and positioned his cock at the entrance of Karen’s pussy. He pushed slowly in, inch by inch, until he was balls deep. He sighed. It had been so long since he had fucked such a tight pussy. He pulled out part way, watching her pussy lips grab onto his cock as if she didn’t want to let it go.
From the hallway, Missy watched, entranced. She did have a good time with her boyfriend tonight, but he didn’t last very long and Missy, ever the nympth, was still crazy horny. She had come out to get some water when she had seen Tom fondling passed out Karen. Missy thought about saying something but the voyeur in her got the upper hand. She slipped her hand into her bikini bottom and started stroking her pussy.
Tom was fucking Karen now. Taking care to not move her body too much and wake her up. He knew this was wrong but it just felt so good. “Take that miss bossy wife!” he thought as he pistoned his cock in and out. “That’s what you get for making me supervise this party.” He looked down and ogled Karen’s curves. He so badly wanted to slam into her but didn’t dare. Missy saw the look on his face and could see that he was getting closer to cumming.
Missy’s eyes widened, “Would he cum inside of her? How naughty!” Then she almost laughed inside at the sheer daring of it. Why, he would be at her mercy now! She had evidence of him doing this and she worked with his wife. Oh the possibilities!
Tom was grunting softly and was going as fast as he could without waking Karen up. Suddenly Missy saw him push all the way in and start to shudder with delight. Tom’s gave a quiet moan as he emptied his balls into Karen’s tight teen pussy. “ohhhhhhhhhhhh, yessssssssssssssss! Mmmmmmmmm!”
Missy put one hand over her mouth to stop herself from screaming as she jammed two fingers in her pussy. Her cunt grabbed her fingers and squeezed tight, rippling and stroking them as Missy came so hard she crumpled to the floor.
Tom heard the noise and looked up. He was standing between Karen’s legs, his cock softening, cum dripping out on the floor. Missy had just collapsed, and Tom knew he was in trouble. Missy caught her breath and saw him.
“You’ve been very, very naughty!” Missy said. “I’m going to tell your wife.”
“Please don’t. She already is being a bitch to me. She threatened to divorce me if I didn’t come over and supervise this party. Man I shouldn’t have come.”
“Yeah.” Missy laughingly said, “You shouldn’t have cum. But we’ll talk later k? I’m really sleepy.” Missy went into her room and closed the door. Tom cleaned Karen up and went home, wondering if things would get better or worse.
Next weekend, Tom answered eskort the door to find Missy there, in her usual bikini, her bronze skin glowing in the afternoon light. “Whatcha’ doin’?” Missy asked coyly.
“Chores.” Tom said. Missy walked inside and started going downstairs. “Where are you going?” Tom asked.
“I talk with your wife you know.” Missy said, “Oh don’t worry, I didn’t tell her how naughty you were last week. We talked about men and their urges. She ended up telling me how naughty you were with her best friend. I wanted to see this guest room where you raped her poor sensitive boobs.”
“Oh come on!” Tom exploded. “What do you want Missy?”
“Your cock. In my pussy. While I cum over and over.”
“No way. I don’t care!” Tom said. “Go ahead and tell my wife, I am so done playing these games!”
“What if I told you that my friend that you so sneakily fucked, was the daughter of someone who has made your life miserable?” Missy slyly said.
“Like who?” Tom asked.
“Sarah. Karen is Sarah’s daughter.” said Missy.
Tom exhaled slowly. “I thought she sort of looked like Sarah. Maybe that is why I did it. That doesn’t change anything though Missy, we’re not fucking.”
Missy’s eyes flashed. “So you’ll fuck Karen but not me? Even though you can’t keep your eyes off my ass? How about this then, what did you want to do to Sarah that you weren’t able to do?”
“Well, Tom mused, she gave me a really good blow job, and a great hand job, but, aside from fucking her boobs I guess I wanted to fuck her. Of course, she never would have agreed to that.”
Missy thought for a moment and said, “So what if I help you live out that fantasy with Karen? Will you fuck me then?”
“What did you have in mind?” Tom said warily.
Missy stepped close to him and turned around, rubbing her tight butt up against his cock. She put her arms around his neck and whispered, “Don’t worry about it, let’s just fuck, I’m SO horny!” with that she pressed her butt further into Tom’s crotch.
Tom put his hands on her sun kissed tummy and said, “I don’t need any more drama in my life, that’s where this is going.”
Missy swayed her hips back and forth and turned to face him, with her arms still around his neck. She sweetly said, “Remember too, I have pictures of you and Karen. We can play nice or I can show your wife.” Tom’s eyes narrowed. Of course she had pictures. Of course.
“You’ll have to work on getting me hard then.” Tom said.
Missy’s eyes lit up and she quickly dropped to her knees. “OMG I have been wanting to touch your cock ALL week!” she squealed excitedly. Tom leaned against the wall resignedly. Missy undid his shorts and watched his semi-hard cock spring free. She gently touched it and fondled his balls.
After a while Tom asked, “Have you sucked cock before?”
Missy got a little red. “Only once or twice. Usually my boyfriend just wants to fuck.”
“OK, start by putting your hand around my shaft like this.” Tom demonstrated. “Then start stroking up and down. Take your mouth and put it on the tip of my cock and suck it.” Missy followed his instructions. Soon there was no sound except the slurp of Missy’s tongue and the slapping of her hand stroking his shaft. Missy was panting with the effort but oh so horny.
“When do we fuck?” she asked.
Tom pulled her head off his shaft and maneuvered her to a nearby chair. “Sit down there and spread your legs.” Tom said. Missy was disappointed when he dropped his head to her pussy, she had wanted his cock. That feeling only lasted for a moment because as soon as he gently sucked her clit into his mouth, Missy writhed in ecstasy.
“Oh Oh oh oh oh oh, that feels so good! Don’t stop baby, please don’t stop!” Tom had no intention of stopping. Missy was soaking wet and very turned on. It wouldn’t take long for her to cum. Tom nibbled on her clit and licked all around her lips. He stroked her flat tummy and her inner thighs. Every time Missy pushed her hips into his mouth he backed off, teasing her, making her squirm. “Make me cum! Please make me cum!”
Tom sisli escort pushed two fingers into Missy’s pussy and moved them in and out, fucking her with his digits. He felt a jolt in his cock when his fingers were gripped by Missy’s super tight pussy. “AAAAAAAAAAAAAAAAAAAHhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh!” Missy screamed. “OHHHHHHHHHHHHHHHHHHHHHHHHHHH! OHHHHHHHHHH! AUuuuuuuuuuuuugh!” Missy sobbed as her body twisted and turned, her hips bucking off the chair.
“Oh that was amazing!” she said. Tom picked up Missy’s lithe body and stood her up facing the wall. Missy felt his hands roaming over her naked, taught, tan body. She shivered with delight. He touched her boobs and made little circles over and under them and down past her rib cage. Missy’s breath quickened. He put his large hands around her tiny waist and lifted up, causing her to bend forward more. He stroked her flat abs and worked his hands lower. Missy was trembling with excitement. She had just cum but already felt like she could cum again.
Tom reached her bush and pulled on some of the hairs. Missy whimpered in anticipation. Then Tom brushed her clit with his finger tip. Missy yelped and jumped. “mmmmmmmmmmmmm.” Missy moaned. Tom pushed her legs apart some. Missy realized she looked like the biggest whore, her face flushed with excitement, her bubbly butt twitching, and her legs spread open like a bitch in heat. Tom rubbed his cock up and down Missy’s pussy slit. “ohhhhmmmmm put it in, put it in.” Missy groaned. Tom slid effortlessly into Missy’s pussy. His fingers earlier had felt just how tight she was. Tom knew he couldn’t last too long in a pussy this tight. He brought one hand down to Missy’s clit rolled it between his thumb and finger as he fucked her from behind.
Missy’s body started jerking and spasming as he drove into her faster and faster. She couldn’t believe how good this felt! Everything was alive! Everything was on fire! Tom took both of his hands and pressed them against her pussy as he thrust as deep as he could inside. With a deep guttural groan he released his cum deep inside her.
“Ughhhhhhhhhhhhhhhhhhhhhhhh, Oh Missyyyyyyyyyyyyyyyyyyyyyyy!” Missy felt a rush of excitement as she realized that she was the one who had made him cum! She felt his hot seed coat the inside of her pussy, causing her pussy to contract and grip his cock. Missy felt the sensations roll through her young body. Her orgasm left her breathless and glassy eyed.
Tom had been holding her up as she recovered. She felt his cum dripping from her pussy and saw it puddling on the floor. “mmmmmmm that was so nice”, Missy contentedly purred. Tom shifted his weight and Missy was aware of his cock, still hard, in her pussy. She giggled, “You’re still hard? I don’t know if I can take any more.”
Missy turned around and kissed him, his hard cock hitting her tight abs. “Do you want me to blow you?” Missy asked.
“Get down on your hands and knees for me.” Tom said. “I want to see that tight ass of yours.” Missy complied.
As soon as she had assumed the position she felt his cock slide into her. “Oh! You’re going to fuck me again? OK baby. Take your time. You know I’m your little cum slut.”
Tom looked her in the eye and moved in and out, savoring her pussy while he looked at her tight ass and her glorious firm body. He had decided that Missy would be a good partner in his determination to get Sarah out of his life. He just had to make Missy want him, as much as he was enjoying her. He raked his nails across her back and massaged her ass cheeks. He pulled on her hair. His short slow strokes changed to deeper, longer strokes.
Missy felt the fire creeping up in her tummy again. She had never cum three times before, but she thought it just might happen again. She knew that she was his forever, and he was hers. She felt his cock swell and cried out with pain and pleasure as he pushed deep inside her, deeper than a cock had ever been before. She felt his cock swell and coat her pussy for the second time. She blacked out with pleasure, faintly hearing a screaming that seemed to go on and on.
She woke up to Tom lying on top of her, his cock slipping out of her pussy, their cum staining the carpet. Tom slowly and stiffly sat up and said, “So how are we going to get Karen?” Missy looked at him impishly and grinned.
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