16 comments/ 472560 views/ 108 favorites Tommy Boy By: johnnyfever Tommy Clarke flopped down onto his bed, resting his head on the pillow. This was turning out to be a pretty good day. It wasn't even noon yet and his schedule was wide open. Due to a teacher illness and some sort of big meeting, his afternoon classes at the local college had been canceled. Tommy still lived at home, an advantage of the college being so close. He had just started his freshman year a few months earlier. Not only was he able to avoid living in the dorms, he was close enough that he could ride his bike to school and get a decent amount of exercise every day. Everything had worked out nicely for him. Normally Tommy had the house all to himself when he finished his classes, but his mother Mandy had taken the week off from work. He figured she'd be waiting at home when he got there, but a note he saw taped to the fridge said she'd gone to the store. Tommy had the house to himself. Lying back on his bed, Tommy unzipped his fly and began his usual afternoon routine. He typically jerked off when he got home, but his mother being around the past few days had put a cramp in his style. He wasn't comfortable doing it with anyone else around. God forbid he get caught or anything. Having gone a few days without relief, Tommy quickly sprouted wood without much effort. He tugged at his cock for a few moments when, out of the blue, he heard his mother's voice calling out. Horrified, he sat up and covered himself, expecting her at his bedroom door. But after a moment he heard her voice again. "Don? Don!" Don was the Clarke's next door neighbor. He was also a real asshole, a big greasy macho type. Tommy looked out the window beside his bed and peered into his neighbor's back yard. They had a large privacy fence, but Tommy's room was on the second floor and he could see over it easily. Don was lounging on a lawn chair, which was all he ever seemed to do. He had on a pair of swim trunks and looked to be asleep. Tommy glanced towards the side of Don's house and saw his mother walking along towards the back. She called out to Don again. Curious to what his mother was doing, Tommy opened his window a little more so he could hear better. "Hmm? What?", Don murmured as he woke up. "Don, I have asked you repeatedly not to park that thing in my driveway!" Don drove a sleek red sports car, all part of his macho image. The neighboring houses had driveways that were nearly side by side, and for some reason Don would often park in the Clarke's when his wife needed to get in and out of their own. Nobody would mind if Don simply moved the car when his wife left, but nine times out of ten he'd forget all about it and stay parked in the wrong driveway. Tommy never understood why Don couldn't park in the street like most people. "Oh. I'm sorry, it slipped my mind," Don told her. "I just got home from the store and I can't even pull in my own driveway to unload the bags!" "Sorry, sorry," Don said again. "Calm down, would you?" Mandy Clarke pushed a strand of hair from her face and put her hands on her hips. "Calm down? I'm tired of this, Don!" "Jesus, I said I was sorry." Don looked over the attractive blonde standing beside him, his eyes gazing at her chest. He'd always had a bit of a thing for Mandy. What a great rack, Don thought to himself. The gears in his head slowly began to turn. "Why are you always in such a mood, anyway?" he asked her. "You not getting it enough or what?" Both Mandy and Tommy couldn't believe what they heard. "Excuse me?" Mandy said, not sure if she heard him right. "C'mon, sweetheart, I'm not blind. That little husband of yours... he comes home late, he leaves first thing in the morning. When's he got time to do you up right?" Almost too shocked to speak, Mandy tried to stammer out a response. How could he be asking her such things? "And when he does do it, he probably doesn't get the job done, am I right?" "That's... that's none of your business," Mandy managed to say. Don was right with his assumptions, but Mandy would never admit to it. She was incredibly embarrassed from this bizarre interrogation, but she was also feeling flushed as she thought about the aching between her legs. It had been so, so long since she'd gotten "done up right". "Well, I say that's what you need, honey. A good fucking." Listening from his room, Tommy couldn't believe what Don was saying. He was two seconds away from running downstairs and kicking this guy's ass, or at least giving it a good try. Mandy was quiet for several moments. She stood there glaring at Don, her anger and her sexual frustration building by the second. Finally, she spoke in almost a whisper. "Are you offering to help me?" Tommy froze. What had she said? He could barely hear her. "You bet," Don said, grinning. Mandy stood there silently for a minute. She glanced towards Don's house. "What about your wife?" "Ahh, she's gone 'till tonight. Where's your kid?" Don asked. "He'll be at class for another hour or so." "Great." Without another word Don reached down and pulled his cock out of his swimming trunks. Mandy looked at it and unconsciously licked her lips. She just stood there, staring at it like she couldn't look away. "Suck it for me," Don told her. Mandy hesitated. "No... I..." Don reached out and took her by the hand. "C'mon, baby," he encouraged. Mandy felt her knees getting weak. She was breathing hard and her pussy throbbed inside her jeans. She finally gave in and stepped towards Don, sinking to her knees next to his lawn chair. Tommy watched in total disbelief as his mother put her mouth around Don's cock and began to suck. "Mmm. Yeah, suck that dick." Mandy slurped and sucked so loudly that Tommy could hear the noises up in his room. He was nearly unable to comprehend what he was seeing. His mother was cheating on his father. She was sucking on this guy's dick. He was watching his mother give a blowjob! Mandy continued bobbing her head over Don's cock. He put his hands into the blonde curls of her hair, pushing her head further down on him each time. "Ohhh. Ohhh, fuck!" Don moaned. Tommy had never imagined his mom doing anything remotely close to this. He knew she must have had sex to get pregnant, but other than that he never gave a shred of thought to her sex life. She was his mother, a paragon of virtue, not some cocksucking slut like various girls he knew at school. But Tommy now knew that he was wrong. Not only was his mom sucking cock, it looked like she was good at it. It made him feel a little guilty, but he'd gotten incredibly hard from watching her. Tommy adjusted the curtains on his window, making sure he could still see out, but closing them enough that nobody would be able to see back in. He began stroking his cock again, his eyes trained on his mother as she slid her lips up and down the shaft of Don's hard-on. "That's great, baby. Get up," Don told her. Mandy and Don both stood up. Don kicked off his swim trunks while Mandy began undoing her jeans. Don pawed at her breasts as Mandy stepped out of her pants, leaving her in just her blouse and a thong. Don leaned her back onto the lawn chair and pulled her panties off. "Get those titties out," he said. "You got a great pair, I can tell." Tommy's eyes were as wide as saucers as his mother undid her blouse. She wasn't even able to take it off before Don immediately unhooked her bra. Tommy's mouth fell open as he saw his mother's naked breasts. He wasn't getting a great look, but from what he could see they were amazing. Don apparently agreed as he greedily squeezed both breasts, briefly sucking a nipple. Mandy moaned softly. "You want it, baby?" "Yes. Please," she whispered. "Tell me you want it." "I want it. Please, fuck me!" Don grinned and aimed his cock between Mandy's legs. She spread them open as Don made his way inside her, groaning as he pushed himself deeper. "Oh! Oh, god!" Mandy cried. Tommy had jerked off before to what he considered unusual material. A documentary on cheerleaders. A women's match on WWF wrestling. A Seinfeld repeat where Elaine looked particularly good. But he never imagined that he'd ever jerk off to the sight of his own mother getting fucked. Don grunted as he repeatedly rammed his cock inside Mandy. She let out a moan with each thrust, trying to forget how terribly wrong this lewd session of adulterous fucking was. She held onto the sides of the lawn chair for support as Don continued slamming her. Tommy watched his mother's face and bouncing breasts and couldn't take it anymore. With a low groan he shot his load into a few wadded up tissues, putting out a fair amount more than usual. Watching his mother had gotten him worked up. Don began slowing his fucking strokes, already close to finishing himself. "You ever take it in the ass?" he asked her. "Yes... uh, no... I..." "Which is it?" Don asked with a chuckle. "We... we can't do that," she finally answered. Don gave a shrug and began fucking her faster. After a few more thrusts he pulled out and shot several spurts of cum onto Mandy's stomach. He stood up and tried to catch his breath as Mandy looked up at him. "I didn't cum yet," she said. "Sorry, baby. Give me a few minutes and we can go again." Mandy looked at her watch and suddenly snapped back into reality. "Uh... no, I've gotta go." She stood up and noticed the gobs of semen now running down her lower torso. Don tossed her a nearby hand towel and she wiped herself off. "How about coming back tomorrow?" he asked. "I... I don't know. I'm sorry." Mandy quickly got dressed as Don walked back inside his house. Tommy hurried to the bathroom and flushed his used tissues, then sat in his room and waited to hear his mother come inside. After a few moments he heard the door slam, followed by the sounds of his mom bringing in grocery bags. When the noises stopped, Tommy heard her coming upstairs. He remained seated on his bed, hoping she wouldn't come near his room. He heard her enter the bathroom and a minute later he could hear the shower running. Tommy saw his chance. He couldn't let his mom know that he'd been home this entire time. He left his room and hurried past the bathroom, then quickly went downstairs and into the garage. He hopped on his bike and headed off down the street. ************* Tommy rode around for a good half hour, using the time to think about what he had seen. As it was happening he had mainly felt shocked and surprised, but as he thought more and more about it, he got angry. Why was his mother cheating on his father? What Don said about his dad hardly being around was true, but Tommy had never considered that it was affecting their marriage. But if she did have to cheat, why with Don? His mother couldn't stand Don. Was she really that hard-up for sex? After those thoughts sunk in, Tommy began feeling something he hadn't expected: jealousy. Why would his mom stoop to fucking someone like Don when Tommy was around? His mom loved him, didn't she? If she was that desperate, why not ask him for help instead of whoring herself out to a guy she didn't even like? It almost seemed insulting. Once he finished his ride, Tommy walked inside his house, wondering what his mother was doing. He headed upstairs and saw that her bedroom door was closed. "Mom?" he called. "Hi, Tommy. I'm in here." "Is everything okay?" "Yes, sweetie, I'm just not feeling that well. I'm going to lay down for a while, all right?" "Okay, mom." Tommy walked into his bedroom and flopped back down onto his bed. Surely his mother hadn't gotten sick all of a sudden. Maybe she was feeling guilty about what she'd done. Serves her right, he thought. With little else to do, Tommy logged on to his computer to check his e-mail. About a half-hour later, while he was responding to a message, he heard his mother open her bedroom door and walk down the padded carpet towards his room. "Tommy?" she called. "Hi, mom." Mandy walked inside his room and smiled. Tommy noticed she had changed her clothes, and was now wearing a long sleeved top and a loose skirt. She sat onto the bed beside him, ruffling his hair. "How was school today?" "Um... fine, mom." he said. Tommy hadn't anticipated this reaction, but he was suddenly nervous sitting next to his mom. Worse yet, he could barely even look at her. Watching her with Don had moved her from "mom" to "hot chick" in the file cabinet of his mind. He felt as nervous as he'd be if a hot senior girl from the college was in his room. "That's good to hear," she said. "What did you do today?" Tommy asked. He always asked her that question, but on this day he instantly regretted it. "Oh, nothing much. I went to the store earlier." Nothing much? Tommy's mind went into overdrive. He was happy with the notion that his mother felt guilty about what she'd done, because at least she knew it was wrong. But now she was acting casually, as if nothing was different. Mandy looked at her son and smiled. Tommy managed to smile back, but he was still turning the situation over in his mind. "I thought I might go out later tonight," she told him. "Would you mind getting yourself some dinner?" Tommy was in disbelief. Going out? Where did she think she was going? Not only wasn't she feeling guilty, she must be going out to do it again. Maybe she called Don from her room and arranged something. Yeah, that had to be it. Then Tommy's mind started racing even faster. What if the incident earlier wasn't the first time she'd cheated on his dad? What if she does it all the time? Tommy made up his mind. He had to put a stop to this, right then and there. "Actually, mom, I wanted to talk to you about something." "What's up?" Tommy took a deep breath. He didn't want to beat around the bush, but then again he couldn't just blurt out that he'd seen her getting fucked. "Well, I... I came home early today, mom." Tommy thought his mom looked a little surprised, but she nodded as she waited to hear the rest. "I was up here in my room and I..." He stopped, hoping his mother could figure it out for herself, but she waited for him to continue. "Mom, I could see outside. I saw what you were doing." The news hit Mandy like a ton of bricks. Her breath caught in her throat and tears instantly welled up in her eyes. She hadn't expected to hear that. She figured he was telling her that he'd come home between classes earlier in the day, before she got back from the store. After all, she hadn't seen him when she came inside. "Tommy, I'm so sorry," she began, putting her hand to her mouth as a tear rolled down her cheek. "I just..." Tommy started, trailing off. "Why, mom?" Mandy wiped at her eyes and looked at her son. "You're an adult now, Tommy, so I'm going to talk to you like one, okay?" He nodded. "What you saw earlier was wrong. I never meant for any of it to happen. And it won't happen, not ever again." "With Don or with anybody?" Mandy took a breath, trying to compose herself. "Tommy, you know that your father is several years older than I am. Sometimes, when they get older, men don't think about sex as much. And with the way he works all the time, he's hardly ever home. And when he is, he's too tired to think about that. It's very hard for me sometimes." Tommy had never considered any of this. He instantly felt badly for her. "How long has it been since you and dad... you know?" Mandy dropped her head, somewhat embarrassed. She did say she would talk to him like an adult, she remembered. "It's been at least a year now. I know it's no excuse for what happened, but I... I wasn't thinking clearly. It's been so long since anyone's shown interest in me that I just lost control of myself." "But what about tonight? Are you going out with Don?" "Oh, honey, no. I was going to meet Pam from my office for a drink." Tommy realized that he'd been way off on that one. Mandy took her son's hand into her own. "I am so sorry that you saw that, Tommy. I can't imagine what you must have been thinking. And to witness your mother doing something like that, oh, Jesus." Mandy started to cry openly, unable to keep herself together any longer. Tommy scooted next to her on the bed and hooked his arm around her waist in a half-hug. She buried her head into her son's shoulder, her tears soaking the collar of his shirt. "It's okay, mom." Tommy held her for a few minutes as she cried. He felt awful for having said anything, for making her feel this badly. Maybe he should have kept it to himself. A few moments later Mandy lifted her head and wiped her face. "Thank you for understanding, sweetie," she told him. "I won't tell dad about any of this, mom. I promise." Mandy smiled at him and rubbed his arm. "Thank you." She took a few breaths, trying to compose herself again. Everything seemed to be okay, but Tommy had one lingering question he still wanted to know. He wasn't sure how to ask, but they had been talking pretty bluntly. He decided to say it. "Mom? I... how come you..." "What, honey?" "Well, if you were feeling that lonely, why didn't you say anything to me?" "What do you mean?" Tommy chose his words carefully. "I mean, you didn't have to do that with Don the way you did. If you'd said something to me, maybe I could have..." "Oh. Oh, Tommy." Mandy smiled with a soft laugh as she took her son's hand. "That's so sweet of you to say, but... you're my son, Tommy. It's not right." "Well, neither is what happened with Don before." Mandy started to respond, but she realized Tommy had her with that one. "Do you love him, mom?" "No, I don't love him." "You love me, don't you?" "Of course I do, sweetie. But..." She trailed off, looking at her son. He was so sweet, so caring. Imagine a young man offering to please his mother sexually if she needed it. "It's wrong no matter what you do, so I just didn't see why you wouldn't ask me before some jerk like him." Mandy smiled and stroked his face. A small voice in the back of her head told her that maybe it wouldn't be so bad, fucking her handsome young son. But Mandy knew she'd need a long time to get used to that idea. Still, the thought had excited her somewhat. Tommy looked back at his mother in a way he'd never looked at her before. He noticed her soft inviting breasts swaying slightly under her shirt. He noticed the smooth tan legs under her skirt. He didn't just want to help her, he knew. He wanted her. Seeing his mom sucking cock, seeing her getting fucked, it must have warped his mind. But Tommy didn't care. Tommy glanced at her legs and saw her skirt resting above her knee. He remembered what she had told Don when they finished, that she hadn't cum yet. She still needed it, he thought to himself. "Mom, I..." "What is it, honey?" "I just want to make you feel good." He looked into his mom's beautiful blue eyes and took a deep breath. In a flash he shot his hands up her skirt, grabbing at the first hint of material. Before Mandy had time to react, he stood up off the bed and yanked her lacy, white panties down to her knees. "Tommy!" she cried. Tommy dropped to his knees on the floor by his bed and pushed his mother's legs apart as she struggled. He knew she wasn't going to suddenly accept whatever he was about to do, so he had to act fast. He tugged her panties off the rest of the way while holding her legs in place. "What are you doing?!" Mandy demanded, trying in vain to force her legs shut. Pushing her skirt up, Tommy got his first close-up view of his mother's pussy. The soft pink skin was just begging to be touched. She was neatly shaved on the sides, with a mass of blonde curls on top. Tommy could have stared at it all day, but he tore himself away and quickly began lapping at her slit. Tommy Boy "Ohhhh! Ohhh, Tommy, noooo!" Mandy cried. Despite her cries of protest, Mandy stopped trying to keep her legs closed. Half in shock, half knowing how desperately she needed it, Mandy sat frozen in place and allowed her son to freely probe her pussy. Tommy smiled as he realized that she was letting him do it. He had gone down on girls before and considered himself a fairly decent pussy licker. He licked his mother from bottom to top, starting just above her asshole and ending at her clit. He licked her fast with only the tip, then went slower and more deliberate with the entire width of his tongue. "Tom... Tommy! Oh my god!" Mandy moaned. She shuddered with pleasure and fell back onto his bed. Tommy slipped his tongue inside his mother's pussy, twisting and twirling it around. Mandy groaned and grabbed at her son's hair, almost trying to force his head farther between her legs. Tommy licked up the soft folds of her pussy lips and then stopped, looking up at his mother. "Oh, Tommy, don't stop!" "Do you like it, mom?" "Yes, baby. I love it!" Tommy grinned and dove back in for more. He spread her lips apart with his fingers and drove his tongue inside her as deep as he could get it. Mandy shuddered again and raised her knees up, giving Tommy even more access to her glistening slit. He lapped at her hole like a drinking puppy, tasting the juices that were practically spilling out of her. Tommy then moved to her clit and began softly batting it back and forth with his tongue. Mandy let out a deep moan and started squeezing her breasts through her shirt. Tommy continued licking and then inserted two fingers inside her. He fucked her with his fingers, feeling the hot wetness of her pussy as it gripped back at him. Making his final move, Tommy put his lips around his mom's swollen clit and began lightly sucking it as he drove his fingers in and out of her. Mandy squealed with pleasure and cried out as Tommy sucked her. "Ohhhh my god! Oh, Tommy!" Tommy kept working on her, wanting more than anything to bring his mother to orgasm. Girls his own age tended to finish as soon as he started working on their clit. He worried that maybe he wasn't doing something right this time. Remembering another technique that had worked on a few girls, he gradually slowed down his licking and then stopped. "Roll over, mom." "Wh... what?" Mandy asked, having fully enjoyed the job he'd been doing. "Get up on your knees," he instructed. Dazed and somewhat dizzy, Mandy did as her son requested and rolled onto her stomach with her knees under her. Tommy lifted his mother's skirt up over her ass and nearly came in his pants. What a sight! His mom had the nicest ass he'd ever seen, and there it was, pointed right at him. Still on his knees, Tommy leaned in and licked his mother's upper thighs, then moved towards the toned cheeks of her ass. Mandy moaned as Tommy gave her butt a solid squeeze and licked at her pussy from behind. Normally Tommy would slide his head underneath the girl's hips, looking up at her and eating her pussy from that position. But he just couldn't pull himself away from the view of his mom's ass. He spread her cheeks apart with his hands, exposing her little pink asshole. Tommy had never done this before, usually thinking it was gross, but it was as if he was being drawn to it like a moth to a lightbulb. Slowly and softly he put his tongue at the base of his mother's pussy and licked up the crack of her ass. Mandy shook with pleasure. She couldn't believe what her son was doing. Tommy couldn't possibly know that she liked having her asshole played with, Mandy thought to herself. But nobody had ever actually licked her there before. It was driving her crazy. "Ohhhh, shit!" Mandy cried. Taking her response as a good sign, Tommy grabbed his mother's hips from behind and zeroed in on her asshole, licking it just like he'd done to her pussy. His fears of it being gross were put to rest since his mother was very clean and hygienic. And to his surprise Tommy tasted a good deal of pussy juice, since it had run down to her ass while she was on her back. Tommy took another big squeeze of her ass and gave it a slap. "Do you like this too, mom?" "Ohhhh, fuck, yes!" Tommy happily continued. He licked up and down her asshole, sometimes fast and sometimes slow, as Mandy encouraged him between her cries of ecstacy. He stopped briefly and watched as his mother's puckered hole throbbed and twitched in enjoyment. Finally, Tommy plunged two fingers back into her pussy and finger-fucked her while he licked her ass. "Unnnnhhh! Ohhhhhh!" Mandy cried. She humped her hips backwards as if she was getting fucked, and Tommy had to fight to stay in position. But he hung with her and worked both his mother's holes as Mandy finally felt her release on it's way. "Ohhhh, shit! Ohh, mommy's gonna cum, Tommy! Ohhhhhhhhh!!!" Tommy stayed with her as Mandy reached her orgasm, shaking and moaning wildly while she bucked on the bed. He could feel her pussy spasm around his fingers as he pumped them in and out. After a few moments, Mandy stopped moving and Tommy fell back onto his butt on the floor. Panting like a dog in heat, Mandy rolled over and collapsed onto her back. "Oh, Tommy. Oh my god. That was..." "I'm glad you liked it, mom," he said with a grin, her juices smeared around his mouth. "I did like it, baby, but... oh, that was so wrong." Tommy grimaced, having hoped that he'd gotten her past that. But as soon as Mandy's orgasm ended, she felt the guilt building up inside her. "It's not wrong, mom, if it makes you feel good." Lacking the effort or reasoning to argue, Mandy just sat up onto the edge of the bed. With shaky knees, Tommy rose to his feet in front of her. Mandy blinked as she realized she was face to face with the large bulge in her son's pants. Tommy looked down and saw his mother's eyes fixed on his cock. An excited chill ran up his spine. "Mom, will you... will you help me, too?" "Oh, Tommy... oh, I don't know..." she protested. "Please, mom?" Tommy undid the button on his pants and quickly unzipped the zipper. Mandy wanted to get up and leave, but she almost felt hypnotized as she watched her son step out of his pants. She wanted to see it, she realized. Tommy didn't disappoint her. He pulled down his briefs, exposing his hard cock to his mother. "Ohhh." Mandy let out a small gasp at the sight of it. Her own son's boner was just inches from her face, how had she let things go this far? Tommy's cock twitched as Mandy stared at it. It wasn't the biggest one she'd ever seen, but it would certainly serve him well. She felt an odd sense of pride as she realized that her son's dick was bigger than Don's. She remembered thinking when she saw Don's cock that it's true what they say about men who buy sports cars. Tommy looked down at her with puppy dog eyes, the look he usually gave her when he wanted something. Usually that meant money, or the latest toy back when he was younger, but never did he think that one day he'd be asking her for a blowjob. Mandy looked up at her son's face and decided to give in. After what he'd just done, she had to return the favor. His poor cock looked like it was going to explode. She knew she'd feel terrible afterwards, but she pushed those thoughts out of her mind. He had gotten her off, she would get him off, and that would be the end of it. "Tommy," she said quietly, "you can't tell anyone about this." "Of course not, mom. I'll never tell." Mandy turned her attention back to his cock. Tentatively, she reached out her hand and wrapped her fingers around it. Tommy let out a low moan as Mandy gripped his hard-on, feeling the girth and the warmth in her hand. She began slowly sliding her hand up and down his shaft, watching the head of his cock swell even larger as she did. "Ohh, that feels good, mom," Tommy told her. "I'm glad, sweetie." Slightly ashamed at what she was allowing herself to do, Mandy lowered her head towards her son's cock and took it into her mouth. She wrapped her lips around it, just wanting to get a feel for it before she went any further. Instinctively, her tongue began swirling around his pulsing cock head, and Tommy groaned with delight. Little by little Mandy took more of his cock into her mouth, forcing her face closer to his body. She couldn't believe how good he tasted, how salty-sweet her son's cock was. Her tongue slid all around his shaft, painting his cock with a heavy coat of spit. With no more preparations needed, Mandy went for broke and started sucking. "Ohhhh! Ohhh, yeah, mom!" Almost in total disbelief, Tommy watched his cock sliding in and out of his mother's mouth. He couldn't believe she was doing it. She was actually sucking his dick! He started wondering how many moms in the world blew their sons, and how many sons licked and sucked their mother's holes to make them cum. Maybe they were the first and only. The sounds of wet sucking and slurping filled Tommy's bedroom as Mandy's lips slid up and down the length of his cock. Mandy had always liked giving head, and even her guilt over doing it to her son wasn't dampening her enjoyment. In fact, she realized that she was enjoying it far more than she should be. Tommy kept his eyes locked on his mother, watching her gobble his cock. He heard her making soft moaning sounds as she sucked. She was enjoying it too, he noticed. But Tommy knew it wasn't going to last very long. Getting a blowjob from his mother was too much for him to handle. Apparently sensing that his release was imminent, Mandy stopped sucking and spiraled her hand around Tommy's cock, jacking him off as she looked up at him. "Are you getting close, baby?" "I don't think it'll be much longer," Tommy told her. Mandy popped his cock back into her mouth, still working him with her hand while she sucked. Tommy put his hands into his mom's hair and softly guided her head. He began rocking his hips to meet her, pushing his cock even further into her mouth. "I'm gonna... I'm gonna cum!" Mandy thought about jerking him off the rest of the way, but she had already come this far. Why not end it properly? Besides, she knew had to get a taste, a reward for her excellent cocksucking. "Ohhhhhhhh! Ohhhhh, here it comes, mom!" Tommy's cock erupted with several shots of thick, gooey cum. Mandy instantly felt the warm blasts filling her mouth and covering her tongue. She continued to jack his cock while swallowing his load, feeling it slide down her throat as she tried to coax out as much of the hot spunk as she could. "Unnnnnggghhhh! Ohhh, yeah." After what seemed like a solid minute, Tommy's cock finally stopped spewing. Completely spent, he fell over onto his bed beside his mother. Mandy wiped the leftover cum from around her lips and licked it off her finger. "Holy shit, mom. You swallowed it and everything." Mandy turned those words over in her head. She had swallowed it. She sucked her own son's cock and swallowed his big load of cum. And what's worse, she had loved doing it. Was there something wrong with her? Was she really this deprived? The guilt flooded back, just as she had anticipated. "That was great," Tommy told her, reaching up to touch her shoulder. "I'm glad you liked it, Tommy. But..." Mandy pushed his hand aside and stood up. She bent down to pick her panties up off the floor, then walked to the door. "I'm sorry, I need to be alone for a while," she said as she left. Tommy sighed and rolled over on his bed. He heard his parents' bedroom door close from down the hall. He really thought getting her to suck his dick was the final hurdle. Why was she having such a hard time with this, he wondered. Tommy looked down at his still semi-rigid cock, which was now smeared with his mom's lipstick. He would give her the space she needed for the moment, but he fully intended on seeing this carried out all the way. Come hell or high water, he was going to fuck his mother. ************* Once he recovered from his mom's amazing blowjob, Tommy finished his e-mails and shut off his computer. He headed downstairs and turned on the TV, flipping around the channels for a while. His parents' bedroom was directly above their TV room, and he knew he'd be able to hear from downstairs if his mother got out of bed. But after nearly an hour, Tommy hadn't heard any signs of movement. It was now late in the afternoon and, having skipped lunch, Tommy decided to make something to eat. He figured his mom was probably hungry, too. Since it would be a good ice breaker, Tommy whipped up a few sandwiches for the both of them. He placed the food on a tray and began carrying it up the stairs when he heard the phone ring. Tommy stopped and wondered which phone he could get to the quickest, but after the second ring the phone was quiet. Maybe his mom picked it up, he thought. Tommy continued up the stairs and walked towards his parents' bedroom. Stopping at the door, he set down the tray and knocked lightly. "Mom?" To Tommy's surprise, his mother opened the door a crack. She was standing right there on the opposite side. "Hi, Tommy. Go to your room, okay? I want to talk to you." Tommy nodded and headed down the hall, leaving the food behind. He sat on his bed and waited. After a minute he heard his mother walking towards his room. Mandy stepped into her son's bedroom and smiled as she walked over and sat beside him on the bed. Tommy's cock hardened almost instantly as he flashed back to the sight of his mother sucking him, and to the sounds of her swallowing the cum he'd unloaded in her mouth. Mandy wasn't sure how to begin. She wanted to tell Tommy what she'd been thinking about, how she had turned the situation over again and again in her mind. She simply couldn't go on without sex any longer, and her handsome young son was the answer to her problems. It was wrong, yes, but Tommy had been right. How was it any worse than doing it with someone else? Tommy was an adult now, she wasn't harming an innocent child. It seemed perfectly reasonable. But Mandy had still been unable to make up her mind. She'd almost been waiting for some kind of sign when the phone ringing had interrupted her thoughts. After a few moments of silence, Tommy finally spoke. "Who was on the phone, mom?" "Your father." "Oh." "He helped me make up my mind about something, which is what I wanted to talk to you about." "Okay. What did he say?" "He said he wouldn't be home until late tonight. That I shouldn't wait up for him." Tommy paused, not sure why she'd need to talk to him about that. His dad always came home late. "So what did you make up your mind about?" "Well. This..." The beautiful blonde smiled at her son and laid back onto the bed, spreading open her legs. She hadn't put her panties back on, and she tugged her skirt up enough to make sure Tommy could see her wet, swollen pussy. He gasped as his eyes locked onto it. "Oh, yeah, mom. Can I lick it again? I'll make you cum really good." "I know you will, baby." Once again Tommy quickly dropped to his knees on the floor by his bed, shoving his face back between his mother's legs. Mandy gasped as she felt his tongue flicking up and down her slit, parting her lips and darting in and out of her. Tommy couldn't believe it was happening again. After several deep licks up the length of her pussy, he rubbed his fingers over her opening, getting them nice and wet so he could put them inside her. "Ohhhh, Tommy! Ohhhhhhhh!" Mandy felt Tommy's fingers sliding in and out of her pussy as he began licking her clit. She had never been serviced as well as he did it. She made a note in the back of her mind to ask him where he'd gotten so much practice at going down on girls. Tommy could tell by his mother's breathing that she was nearing her climax. This was the point of no return. She would never be able to turn down a good fucking when she was this hot. Quickly, Tommy stood up and went for his fly, taking off his pants. Mandy sat up on her elbows and watched as her son's cock sprang out at her. She knew what he was thinking. "It's okay, sweetie. I want you to fuck me. Slow down." Tommy grinned. She was going to let him do it. He pulled off his shirt and threw it behind him. "But come here first." Mandy sat up as Tommy leaned in towards her. They met in a kiss, a hot mix of wet lips and tongues. Mandy moaned softly as she swirled her tongue around inside her son's mouth. Almost unconsciously, drawing on his back-seat dating experiences, Tommy reached out and got his first feel of his mother's soft breasts. A moment later they separated. "Ooh, you're a great kisser, too," she told him. Tommy withdrew his hand from her chest, but Mandy took him by the wrist and guided his hands back to her spongy tits. Tommy's cock throbbed harder than it ever had as he squeezed her large breasts through her shirt. "You like 'em, don't you?" she asked. "Oh, yeah." "I bet you wanna see 'em, huh?" she asked. Tommy could barely manage a nod in response. Mandy pulled up her shirt and tossed it aside, leaving just her white, lace bra between Tommy and her full C cups. Even inside her bra, her tits were the most incredible thing Tommy had ever seen. He slowly reached out towards them. "You can do it. It's okay," she told him. Tommy took a big squeeze of her left breast as Mandy moaned and arched her back. Carefully, he reached around behind her and undid the clasp of her bra. He slid the straps off her shoulders and fully exposed his mother's breasts. Tommy immediately felt light-headed, as all the blood in his body seemed to rush straight to his cock. He'd never been so hard in his life. "What do you think?" Mandy asked. Tommy couldn't even speak. "I'll take that as a good sign," she said with a laugh. Mandy laid back onto the bed as Tommy leaned over her, squeezing and sucking her tits. Her large nipples stuck out like thick pencil erasers, and Tommy moved back and forth between them, sucking each one as his hands kneaded her breasts. "Ooh, that feels so good," Mandy told him. "Can I... can I fuck you now, mom?" Tommy asked hesitantly. "You sure can, baby." Mandy reached down to take off her skirt, but Tommy stopped her. "I like the way it looks on you, mom." Mandy smiled and opened her legs as Tommy pushed her skirt up, making sure he had plenty of access to her pussy. "Give it to me, Tommy," she encouraged as she scooted her hips towards the edge of the bed. Tommy guided his cock to his mother's swollen, pink opening. He was going to do it. He was going to fuck her! "Here we go, mom." Tommy pushed the head of his cock through the soft, pink folds of her pussy. Mandy let out a contented groan as her pussy spread open. She was tighter than Tommy had anticipated. Inch by inch he continued sliding himself inside her, filling his mother with his thick cock. "Ohhh, baby! Oh, shit!" Mandy cried. "Fuck me, Tommy!" Tommy did as his mother asked. He slid his cock out of her until just the head was left inside, then shoved it back in as he began a steady pace of fucking. "Oh! Oh! Oh, yeah!" Mandy moaned. Tommy's eyes were fixed on his mother's breasts as they bounced in rhythm to his strokes. The large globes bounced up, down, and off the sides of each other, with her eraser-like nipples making little circles in the air all the while. He had never seen anything quite so amazing. Likewise, Mandy's eyes ran up and down her son's body. What a stud he's turned into, she thought. She hadn't seen him with his shirt off in a few years. He had obviously been working out. His muscles were flexing and shining with sweat as he worked. Tommy finally looked away from his mom's tits and their eyes met. They both smiled. Tommy Boy "Holy shit, mom. I can't believe I'm fucking you!" "Me neither, sweetie. You're doing so good." Mandy sat up on her elbows and watched as Tommy's cock plowed in and out of her pussy. She had always liked visual stimulation, and knowing that the cock she was watching belonged to her son made Mandy even hotter. Tommy sped up the speed of his strokes, fucking his mother faster. Mandy groaned and grabbed his shoulders. "Yeah, just like that," she encouraged. "Fuck me right there! Ohhhh!" Mandy tried humping her hips towards him, wanting to get Tommy's cock as deep inside her as it could go. She had been close to cumming when he stopped licking her pussy, and she could feel another one building up from deep inside her. "Don't stop, Tommy! I'm gonna cum! Mommy's gonna cum!" Tommy grunted and fucked her even harder, desperate to give his mother the best orgasm possible. Mandy squealed and trembled as she felt the waves of pleasure overtake her. "Ohhhhhhhh, I'm cumming!!! Ohhhhh, fuck!" Tommy continued fucking her through her orgasm, feeling the spasms as her pussy clenched and squeezed at his cock. He slowed down his strokes as his mother finally stopped shaking beneath him. "Tommy, stop for a second, sweetie." Tommy stopped fucking and pulled out of her. "I just need a minute. Mommy's pussy gets really sensitive after she cums." "It's okay, mom," he told her. Mandy tried catching her breath, giving Tommy a chance to watch her breasts heaving. Suddenly, a thought popped into his head. "Um... mom?" "Yeah, honey?" "I heard you earlier with Don, and..." "Yes?" "I thought you said something about... about having taken it... in the ass." Mandy bit her lower lip. She'd had anal sex on several occasions, first out of curiosity and then out of enjoyment. She had to coax her husband into trying it with her, as he had wanted no part of it. But Mandy liked having her asshole played with, she couldn't help it. And that had naturally led to the next step. Mandy wasn't about to let Don get that far with her, but Tommy was another story. She was still tingling from the intense asshole licking he had given her earlier. Mandy looked at Tommy's throbbing cock, just inches from her face. She knew she had to feel it in her ass. "Yes, sweetie, I have." "Well, uh... maybe we could..." "Young man, I'm shocked," Mandy said with a playful sternness to her voice. "Are you saying you want to fuck your mother up the ass?" "Hell, yes," Tommy told her. "Ooh, I had no idea you were so nasty, baby." Tommy gave a shrug and Mandy laughed. "Well, I think that can be arranged," she said. "But we're gonna need some lu..." One step ahead of her, Tommy reached to the drawer on his night stand and pulled out a jar of Vaseline that he occasionally used while he jerked off. "Anything else in there I should know about?" Mandy asked with a grin. "Uh... no, I just..." "I understand, sweetie. Now spread it all over your cock." Tommy scooped up a glob of the jelly as Mandy positioned herself on the bed. She got onto her hands and knees, then let the upper half of her body rest on the mattress with her ass pointing up in the air. She kept her head turned to the side so she could watch her son behind her. Tommy smeared the Vaseline all over his pulsing hard-on. Mandy softly swayed her hips back and forth, awaiting what was about to come. Watching his mother's ass had Tommy hooked again. "Want me to lick it first, mom?" "Ooh, you read my mind." Tommy leaned down toward his mom's tanned, toned ass and repeatedly ran his tongue over her asshole. Mandy shivered as Tommy's tongue flicked at her little hole. She could feel it puckering with anticipation. "That's enough, Tommy. I want you in me." Tommy stood up and aimed the head of his lubed cock directly at his mother's ass. He had never fucked a girl in the butt before and wasn't sure what to expect. "Go slow so I can get used to you, okay?" Tommy nodded. He put his cock up against her asshole and slowly began to push it in. "Ohhhhhhhhhhh! Ohhhh, fuck!" Mandy moaned. "Is it okay, mom?" "Yes, baby. Keep going." Little by little, Tommy carefully pushed his cock farther up his mother's ass. It was hot and smooth, unlike anything he'd ever felt before. It was also incredibly tight, much more so than her pussy. It was like a hand gripping his cock and squeezing it hard. Mandy grunted as she felt him going deeper. "Oh, shit! Unnnngggggggh." It hurt a little, but Mandy could take it. She couldn't wait for him to start fucking. "Tommy, oh my god! It's so big," she panted. "Oh, fuck, you're stretching my asshole open! Unnhhh!" Finally, Tommy's balls came to rest on her pussy. His entire cock was inside his mother's ass. "It's all the way in, mom." "Oh, baby, fuck my ass. Fuck it good!" Tommy didn't need to be told twice. He began pistoning his cock back and forth, driving it up his mother's butt. Mandy moaned wildly and humped her hips backwards to meet his strokes. "Ohhhhhh, fuck! Ohhh, Tommy, you're so deep!" For the next few minutes the only sound in the room was Mandy's deep grunting as her son's cock drove in and out of her asshole. She was going to be sore afterwards, but it was well worth it. Her husband's cock didn't feel half as big in her ass as Tommy's did. She reached down between her legs and rubbed her clit while he fucked her. Wanting to keep it going as long as he could, Tommy let his mind wander to avoid cumming too fast. He thought about the absurdity of the entire situation. A teacher illness, a meeting at the school... who would have thought that such unrelated issues would lead to this? Before today, a peck on the lips was the most he'd ever done with his mother. But already she'd given him a blowjob and swallowed, he'd licked and fucked her pussy, sucked her tits, and now he was actually fucking her up the ass. It sure is strange how things work out. The sound of his name snapped Tommy out of his thoughts. "Ohhhh, Tommy! This feels so good!" "Yeah? Do you like my cock up your ass, mom?" "I love it, baby! I love your cock in my ass!" Tommy plowed into her a few more times, then pulled out completely, watching as his mother's asshole stayed open in anticipation for more. He slid back inside her and continued fucking. "Oh, fuck! I'm gonna cum again!" she cried. Mandy rubbed her clit faster as Tommy sped up his strokes. "Fuuuuuuuck!!!! Ohhhhhhhhhh, Tommy!!!" Mandy's entire body exploded with pleasure. Her pussy gushed out juice onto her hand as her ass muscles contracted around Tommy's cock, squeezing it tightly. Mandy had never cum that hard before. She was almost in shock as the sensations died down. His mother's ass gripping his cock during her orgasm had pushed Tommy over the edge. He continued fucking as he felt his balls start to boil. "Mom, I'm gonna cum!" Mandy quickly leaned forward and Tommy's cock left her ass with a small 'pop'. She spun around on the bed and grabbed his cock, jacking it off as hard as she could. She wouldn't have minded an explosion of cum up her ass, but Mandy wanted to taste him again. She had loved his first load too much to let this one get away. Tommy fucked his greasy cock into his mother's hand, watching her tits jiggle as she jerked back at it. "Ohhhhh, here it comes!!" A huge rope of cum shot from Tommy's cock and splattered across Mandy's face. She continued to jack him off as more shots spurted out, coating her lips, neck, and chest in his cum. "Ohhhh, yeah!!" Tommy groaned as a few final shots dribbled onto his mother's tits. He couldn't believe he had shot so much, considering that he'd already cum twice that day. "Oh, my baby. Ohhh, Tommy." Mandy cooed with delight as she licked the cum from around her mouth. She looked down at the gobs running down her chest and wiped them with her hand, savoring every drop as she sucked it from her fingers. "God, that was great, mom." Mandy pulled her son towards her and they collapsed onto the bed together. She couldn't remember the last time she'd felt so satisfied and content. "Wanna do it again?" Tommy asked. Mandy laughed. She wasn't used to having a man with such endurance wanting to fuck her. "You better save your strength, baby. I think I might take an extra week of vacation, so you're gonna need it." Tommy grinned as his mom cuddled up beside him. This had definitely turned out to be a pretty good day. THE END Tommy Boy It was an unseasonably warm New Year's Eve for Chicago: 60 degrees, t-shirt weather for the natives. I had just left a dinner with my group of friends to head to a party in a neighboring suburb to which my friend James had invited me. Over the course of our winter break, sexual tension had been climbing between us but I still wasn't sure I wanted something to happen. He was staggeringly witty and had a chiseled jawbone but I found him just a tad too slick on occasion, and this put me on edge. As a girl wholly disinterested in dressing up and playing nice, I was clad in my go-to outfit for most occasions barring weddings, funerals and job interviews: yoga pants, UGG boots and a shirt from Urban Outfitters that ran a thin line between beautifully fashion forward and merely questionable. I stood on the front porch enjoying the night, waiting for James to answer his phone. Mid-ring, the door opened and it wasn't James but his best friend Tommy. Let me take a detour here and explain how I knew Tommy. At the first (and only) rager I ever threw at my house, James had come bringing several of his best friends. I was dating an enormous tan moron at the time but despite that my jaw had hit the floor the first time I saw Tommy. He was tall, 6 foot 2 and muscular in the best way possible: from years of working out and crew. He had a mouth normally set in a grim line and tawny eyes. When he laughed, his nose and eyes crinkled. He was perfectly masculine, devastatingly handsome and generally grumpy. While we didn't exchange more than a few words the night of my party, I had seen him once over winter break when we saw the latest installment of the Harry Potter movies with James. They had made fun of me for sobbing unrestrainedly when Dobby the house-elf died. I had no idea what he thought of me. He was the definition of stoic. He ushered me into the house wordlessly and once inside we hugged awkwardly. The party was typical of college freshmen: lots of Natural Light beer and UV Blue drunk straight out of the bottle. At midnight we all gathered downstairs to watch the bottle drop. James and I had already joked that we would be each other's midnight kiss but secretly I was already wondering how angry he'd be if something happened between Tommy and myself. The ball dropped, Tommy popped the champagne and James and I kissed: closed mouth. He was well on his way to obliterated and I was quite sober so there was much attempt at Frenching on his part and hasty retreat on mine (insert disparaging remark about French here). As Tommy passed me the bottle of cheap champagne, we heard that the host's aunt would be dropping by soon to check that all was in order. Naturally, this presented an issue for us so we gathered coats and shoes and met outside to game-plan. Standing in a circle on the sidewalk, shivering slightly, we discussed what to do. There were parties all over the North Shore that we could go to, but none of us could drive by that point. Eventually we decided to walk and as we started to do so, Tommy reached down and firmly grabbed my ass. I looked up at him, honestly surprised and he grinned down at me. My heart flip flopped. "Excuse you," I whispered (though everyone was far too drunk to notice) "That's my ass thank you very much." "You're welcome." Tommy responded. "My hand is warm." "You're a piece of shit," I reprimanded him, smiling inwardly. He withdrew his hand from my yoga pants and smacked my ass. "Start walking, we're lagging behind" he commanded. My stomach fell out my butt. I love a man who orders me around. Tommy, James, their best friend Henry and I began to walk towards a party we knew of. The night was fine when we were moving and we drank beers and smoked cigars as careless teenagers are wont to do. Cars honked at us and we yelled back a cacophony of happy new years' as we laughed and fell over ourselves. Tommy intermittently grabbed my ass and pulled me closer and I would scooch away, laughing. Henry and James were walking a few feet in front of us singing Irish drinking songs and making general asses of themselves. Tommy and I didn't speak much, just laughed and enjoyed the night and the moment. Then we simultaneously looked at one another and he leaned down (I'm 5'4" on a good day) and kissed me while we walked. Yes it was as awkward as it sounds. And yes, sparks flew. We giggled to ourselves, enjoying the scandal of kissing while Henry and James walked just a few feet in front of us. We hopped from party to party that night courtesy of a friend of James' who we happened upon (seriously) at a stop sign. I sat in between Henry and Tommy in the back seat and endured much fondling from both of the two drunkards. We ended up at the house of a kid that everyone but me knew. In his expansive basement we cracked beers and sat around shooting the shit. James was extremely drunk, Henry and Tommy less so and I was sober. Henry had been noticing the sparks flying all night and was taking full advantage of giving us shit. James was oblivious, more intent on feeding Heineken to our host's mastiff. Eventually I got up to go to the bathroom and as I walked around the corner, Tommy grabbed me and pulled me into the basement bedroom. He slammed the door closed behind him and growled in my ear, "This ends here." I swooned. I grasped his face with two hands and we kissed, really kissed. Our lips pressed together and something even better than fireworks exploded behind my closed eyes. Our tongues grappled with one another and he bit my bottom lip, less than gently. He picked me up and threw me onto the unmade king sized bed and that's when I realized we were in the host's bedroom. Given the moment, I threw caution to the winds. We rolled around the bed kissing furiously. Tommy unzipped my shirt and threw it across the room. His lips found my neck and my earlobe and he kissed me furiously, his stubble scratching across the sensitive skin. "You're so sexy, you're so sexy" he kept whispering into my ear. His hands were large and calloused and he had me tightly ensnared in his grip. That being said, I had no intention of leaving. I could feel him pressing through his corduroys and I shifted my shoulders to place one hand gently on the bulge. He stiffened and looked at me through the gloom. "Is this what you want?" I whispered. "Yes." He half growled, half groaned. "Tell me what you want," I bit his earlobe. "I want to be inside of you." That was all I had to hear. My yoga pants and one sock were flying across the room not even a second later and a condom was coming out of his wallet. He threw me back against the pillows and rolled the condom onto his impressive length. "Go slowly," I warned him (A side note: I have reason to believe that am the tightest non-virgin alive. It doesn't matter if I had sex five minutes ago or five weeks ago, it's a fortress. And I haven't met a man yet that doesn't love it. Tommy was no exception). Our skin on our chests met and burned as he slowly pushed into me. I wrapped my legs around his broad back and gasped as I felt the head of his cock move into my pussy. Though I was dripping wet by that point, he moved inch by inch until I was full and there was still more of him left. He looked down at me. "There we go," he groaned. "There we fucking go." I grabbed the back of his head as he began to punish me and kissed him with all my might while hanging on for dear life. I pushed my hips back against his and we settled into a perfect furious rhythm, my lips at his neck and his enormous hands around my hips. His panting in my ear only served to excite me more but I didn't want to cum just yet. "Hold on," I gasped, putting my hand on his burning chest. "Let's switch it up a little bit. Tell me what you like." He blinked at me, obviously struggling to pull a lucid thought together out of the fog of testosterone and alcohol. "I don't know," he murmured. "I guess..." He pulled out of me with a loud slurp and flipped me over, pushing me up against the headboard. I lifted my hips and let him in from behind. He groaned audibly and bent over my back whispering in my ear how tight I was. I laughed and pushed back against his hips even harder. He began to fuck me from behind and I could feel myself getting close. His enormous hand closed around one of my breasts and began to knead it hungrily. I reached back between our legs and got hold of his balls, which were tightening with every second. He groaned and slammed into me harder until I was also moaning audibly as he stretched my pussy more and more with every passing second. All of a sudden he stopped. "I want to eat you out." He pulled out again and threw me on my back and just as his tongue touched my clit a thunderous hammering on the door began. I was livid. And I was so close another two seconds would have had me cumming harder than I had in two months. We could hear James slurring outside the door to come out. We both groaned and Tommy gently kissed my now red and sopping pussy. I almost grabbed his head and pushed him back down there but we were guests, and I was sober enough to know better. We rolled off the bed and began searching for our clothes. Tommy's massive erection was still very much there and I looked at it and then looked at him. "Suck my dick," he growled, peeling off the condom. I knelt down and as my tongue touched the tip the hammering on the door began again. "Jess, Tommy get outta there!" James slurred. "You needa come outta there!" he reiterated. A frantic search for clothes ensued and we slunk out of the room minutes later, stinking of sex, our cheeks glowing. To be continued... Tommy Boy As a young man, I developed a strong attraction for older men. My fantasies, in the main, focused invariably on being seduced and then laid by attractive older guys. In these imaginings, I was eager to follow the lead of the experienced, and always strikingly masculine man that I conjured from thin air. Some of these fantasies were ultimately realized, and I was fortunate that each realization lived up to my imagination, and then some. The younger man being mentored, protected, and ultimately fucked by the older - professor, family friend, uncle, neighbor - was an incredibly powerful theme in my sexual imagery of those years. As a mature man in his 50's, I have recognized that my youthful fantasies might be shared by some of the young men of today - except now, I am the experienced older man for whom these young bucks might have such fantasies. As good luck and circumstance would have it, a few years ago I found myself in just such a situation. I have travelled constantly in the course of my work, spending months or years on different projects throughout the United States. For these assignments, I usually lease an apartment in the city where the work is conducted, and fly home once or twice each month for the weekend. I began one of these assignments, in Chicago, in the usual way: I sat across the leasing desk at an apartment complex, arranging for an apartment. The young man that sat across from me appeared to be no more than 19 or 20. He was such a beautiful boy. I expected he was quite popular with the women. As he explained the various documents and went through his normal routine of preparing the lease, I slowly began to extend my opinion of his popularity to include men. Something about him - the way he looked at me, perhaps, or the way he smiled - made me wonder if he might be playing exclusively for the boys' team. Anyway, it was a pleasant exercise to watch him and to look for subtle clues as we went through the process of signing documents and distributing keys and gate passes. When we were finished, we stood and shook hands. I made sure to wait until he released his grip before releasing mine, and was pleased to note that he held my hand just a little bit longer than one might do on a purely casual basis. Or, perhaps this was the delusional hope of an old man for the attentions of someone 30 years his junior. I have to remind myself occasionally that the world is full of possibilities for the young and beautiful, and that the young and beautiful do not, as a rule, entertain any thoughts whatsoever of the older and less beautiful. Still, as was true for me when I was a young beauty, there are exceptions. The young man's name was Tommy. I saw him a few days later when I found that the mailbox key I had been issued would not open my mailbox. I went into the office, held up the key, and told him it would not work for the mail, and that perhaps he had given me the key to his heart by mistake. Corny, of course. But I have always tried to cultivate a talent for being dumb in a clever way. In any case, Tommy looked at me in an appraising manner for the first time. He smiled and said no, his heart could be opened by combination, but not by key. He retrieved another key and we walked to the mailboxes together. Voila, the key worked, and I told him he was very nice. He said yes, he was nice - to nice guys. I thanked him and he walked off toward his office. I looked after him and thought, my God, what a butt on that little guy. Some days later, as I walked across the parking area toward my car on a frosty morning, I spied Tommy looking into the engine compartment of a Toyota parked near my parking space. I walked over and we deduced that his car's battery, most likely due to the cold, was dead. I told him we might boost the engine with some cables, but he said he was running late for a class and thought he should try to find a ride instead. I was happy to oblige, and drove him to the university campus. On the way we talked about the goings-on in our lives and our backgrounds. As we rolled to a stop and he prepared to exit the car, I told him he was welcome to come by the apartment for coffee or a drink anytime he liked. A few days later, I trudged through falling snow to retrieve my mail, and Tommy came out of the office. He pulled his coat on as he jogged over to me. He thanked me again for the ride I had given him, and for the invitation to drop by. He asked if he might come by that night, if I didn't have plans. I told him of course, I would like that. Then I teased him by suggesting that if it kept snowing at the current rate he might get snowed-in with me and have to stay overnight. Yes, corny. He laughed and told me he was sure I could find some way of entertaining him if that should happen. Then he turned and jogged back to the office. Tommy did indeed at least pretend to be snowed-in, as he did spend the night with me. And much of it he spent with my cock in his lovely ass. He knocked on my door around 8:00 P.M., his cheeks pink from the cold wind, and with snow in his hair and on his coat. I soon warmed him up with a few glasses of merlot. We sat on the sofa and talked, not sitting especially close to each other, but not far apart, either. There seemed to be some force that slowly moved us closer, and at some point Tommy placed a leg across my thigh. I placed my hand on his leg and began stroking him from knee to hip. We sat talking in this way for some time, quite casually, I thought, given the possibilities that each of us was entertaining - that is, I assume Tommy was entertaining possibilities. I certainly was. I was thinking about how I planned to make him melt beneath me in my bed. I told Tommy about how I had fantasized about older men when I was his age. I told him a few details of my sexual encounters with men who could have been my uncle or father. I explained that, now that I was older, I found the idea of playing the senior role for younger guys very appealing and arousing. Tommy told me he often fantasized about being with older men. He confided, haltingly and a little breathlessly, that he had always wanted his stepfather to come into his room and take him hard, but that it had only been a fantasy. Come into the bedroom and let me fuck you, I told him. I took Tommy into the bedroom, removed his clothing, and put him on the bed. He had a beautiful body, smooth and lightly muscled. He had the most beautiful dick, a slender 5 inches with a perfectly shaped head. And his tiny bottom, with its perfectly pink bud, made me hard immediately. I climbed on the bed and lay halfway on top of him. I kissed him deeply and he responded, almost frantically. I helped him relax by holding him and whispering to him. I told him what a beauty he was, and how much I wanted him. He held my dick and squirmed beneath me. I moved down and sucked him until I sensed that he was about to unload, and then I stopped and told him I didn't want him to cum until he had first taken some of my cock. I knelt by his legs and stroked by stiff shaft, showing it to him. He said only one word: "Please." I rolled on a condom and made myself slippery with lubricant. I could not resist licking his little hole for a moment. He had a world-class derriere, Tommy did. I lifted his legs, which he took from me and pulled toward his chest. I penetrated him slowly, and did not hurt him at all. What an unfettered joy it was to get all of me into him and start riding him. Tommy was the perfect size for me. Just right for kissing on the lips while engaging with his ass, light enough to maneuver about the bed to achieve the best leverage and angle. As I came closer to exploding in him, I leaned close to his ear and asked him if he liked his daddy's dick. This might have cued his old fantasies about his stepfather fucking him, I don't know. But in any case, he cried out - a shriek, almost - arching his back and bucking like a wild pony. He raked my back with his nails and came between us as I deposited my sperm deep inside him. Tommy was a superb lover, eager to be fucked and a very sensual person. We became good friends while I worked in Chicago. I thoroughly enjoyed my role as someone who could be helpful to Tommy when he needed help or advice. And over time I think discovered at least part of the combination to his heart.