Date: Thu, 7 May 2009 23:22:46 +0000 From: A. B. Subject: The Maintenance Man - for TG/Teen section The Maintenance Man TG/Teen ________________________________________________________ This is a true story. It happened to me a long, long time ago (about 30 years ago). I had actually forgotten this incident...had pushed it back into the corner of my mind until I happened to be chatting on-line with a friend when it all came back to me in a rush. I wish my friend (you know who you are) would e-mail me so we could chat more about this. In any event, this story depicts a homosexual encounter between a man and a teen. If that offends you, tough. Grow up and don't come to these sites. I hope you enjoy this story. Be safe everyone. Comments are always appreciated. Love, Jack/Jackie ___________________________________________________________ Jack was excited. His heart pounded in his chest as he rushed to the basement of the old motel where he worked part-time as a mantenance man. He kept thinking that someone must have seen him take the bra and panties out of the lost and found barrel in the maid's break room but no one was around and he heard no shoults telling him to stop. Jack was 16 years old and worked after school at the Blue Parrot Motel. Technically his title was "maintenance man" but he basically just did odd jobs. It was shit work but the pay was more than minimum wage and paid for gas for his car and some pocket money. It fit in his schedule nicely and he knew it wouldn't be forever, just till he graduated next year and went off to college. His job mainly consisted of bringing the bins of dirty sheets and towels the maids collected over to the laundry room and fixing the occasional lamp or unclogging a toilet. He hated working the weekend shift since he had to wake up extra early to stop by the bakery store and pick up donuts for the "continental breakfast" the motel offered, but other than that, he couldn't complain. Jack was free to hang out and do pretty much whatever he wanted and pulling those laundry bins up and down the stairs and through the slush covered parking lot in winter gave him a pretty good workout so his trim body was in decent shape. He liked shooting the shit with the maids while they were on their break but they mostly reminded him of his mom. For the most part they were older ladies and, though nice enough, didn't turn him on. There was one girl though who was kind of cute. But even she didn't really do it for Jack since she was about 25 pounds overweight. Nevertheless, he knew she liked to check him out and that she thought his 5'8" 150 lb blond and blue eyed body was cute. Jack liked the attention but didn't really think about having sex with her. The Blue Parrot was one of those non-descript "no-tell motels" on the main highway in Jack's town wher businessmen took their secretaries during the day for a quickie. Indeed, the maids would often tell Jack when he'd get there after school in which rooms illicit affairs were being conducted. The maids got a kick out of telling Jack even though there was nothing he could (or would) do, but he, like the maids, got a secret thrill out of knowing that some guy was cheating on his wife with some hot little slut. He got especially turned on on the rare occasions when he'd actually see some old guy in a business suit leaving with a twenty something hottie and imagingin how she 'd just been fucked. Although Jack was a good looking kid, he was terribly shy around most women, at least the ones he was attracted to anyway, and so he was still a virgin. He'd gone on a few dates and felt up a couple of girls. But that was as far as he'd gone. One of the things Jack especially enjoyed was looking int he lost and found bin while bullshitting with the maids. They would often show him the most amazing things that people had left behind. Vibrators and dildos, lingerie of every shape, color, size and style, oils and creams, candles, watches andonce even a strap-on. Jack was so naive he had asked one of the girls what it was. It sort of looked like a dildo but he couldn't imagine what the straps were for. The maids laughed and he turned red in the face when Shirley, one of the older women, held it up in front of her crotch. Jack left the break room as quickly as he could after that without looking like a complete idiot. He'd laughed along with the maids at his own ignorance but he'd been very embaressed. The only other person Jack really talked to, besides the maids and the two women who did the laundry, was the other maintenance guy, Tom. Tom usually worked mornings and typically got off before Jack came to work but occasionally, their schedules would overlap for an hour or two. Tom was 24, tall, muscular, without being muscle bound, with short dark brown hair and green eyes. His chiseled face and square jaw made him classicaly handsome and the maids swooned over him whenever he was around. It had even been rumored that Tom had banged both of the women that worked in the laundry at the same time but Jack had never been able to confirm this. Tom had dropped out of college a few years ago. He told Jack that it "just wasn't his thing" and he was wroking at the Blue Parrot until he figured out what he wanted to do with his life. Jack thought he was cool. For the first week that Jack worked at the motel, Tom had basically taken him under his wing. He talked to Jack as an equal and was patient and kind to him, unlike most of the kids Jack's own age who tended to bully him and called him "sissy" and "fag" simply because he wasn't athletic. They talked about science fiction and horror books and, to Jack's surprise, Tom told him he liked reading comic books too. The best, however, was when Tom showed Jack the secret stash of porn hidden in the basement of the motel. Way in the back of the basement, past the piles of broken lamps and tools and supplies, hidden on a corner of a worktable, was the biggest stack of pron Jack had ever seen. These weren't Playboys and Penthouse like Jack had found in his father's closet, however. These were hardcore porn magazines that had come from adult bookstores in the city. There were the usual Hustler and Cheri magazines, but what fascinated Jack even more were the obviously cheaply made magazines. Some, particularly the swinger magazines, were even in black and white and loaded with personal ads for every conceivable type of kinky perversion you could think of - and some Jack had never imagined. Those magazines showed a lot more than even the Hustlers. Women sucking men's cocks, cum dripping down their faces. Women getting assfucked and pissing, Lesbian's with their tongues shoved up each other's twats. "Where did you get all these?" Jack asked Tom. "The maids find them left inthe rooms all the time and they give them to me. Hey, check this out," Tom said. He showed Jack one particularly explicit magazine with no title and a picture of a girl with very flat chest and no pubic hair on the cover. She looked like she couldn't have been more than 13 years old. When Jack tried to open it, however, he found the pages practically glued together. He thought Tom was pulling his leg and asked, "What gives?" Tom laughed and said, "Whoever was looking at this one must've cum all over the magazine. That's why the pages are all stuck together." "Ewwww," Jack said, and tossed it back on the table. The stack shifted and fell over onto the table. Something caught Jack's eye. Spilling out near the middle of the pile were a few issues of something called Blue Boy. The covers of which featured naked hunks with huge cocks that were so gorgeous Jack felt his knees go weak. He tried not to look like he was excited by these and casually flipped past them as though they held no interest for him. He knew, however, that as soon as he was alone in the basement, those would be the first magazines he looked at. That was because the one thing Jack hadn't told Tom - the one thing he'd never told anyone - was how much he liked to wear his sister's clothes and jerk off while imagining he was a girl. Jack had begun dressing up when he was around 12 years old. He'd been int he bathroom one day stroking his little cock when he noticed a pair of his sister's pantyhose hanging on the shower rail drying. For some reason he'd never been able to explain, Jack had become intensely curious about what it would feel like to wear them. He slipped them on and reveled in the way his legs felt. He'd cum pretty quickly after that and washed them out and hung them back up to dry. Ever since then, Jack had been a closet sissy crossdresser. He'd begun trying on all of his sister's things, and even some of his mother's clothes as well - though he preferred his sister's since they were much prettier and sexier. Jack had gone through all the clothes in his sister's closet. Jack's sister was two years older than him and, at that age, he'd been small enough that he'd been able to fit into just about all her things. His favorite clothes, however, were her white tennis skirt and a powder blue warparound skirt. Every chance he'd get when he was alone in the house for a few hours, Jack would raid his sister's closet and dresser and slip on her training bra (later her regular bras stuffed with socks), panties, half slips, full slips, babydoll nightys, skirts, dresses, even her pants. Jack liked to tuck his little peter up between his legs and put on a pair of his sister's tight pants and admire the smooth front of his crotch. When Jack had turned 16, his sister went off to college. His parents would go away most weekends to a house in the country but, since Jack worked at the Blue Parrot most weekends, he'd be home alone. It was heaven. As soon as his parents would pull out of the driveway, Jack was in his sister's room stripping naked and going through the clothes she'd left behind wondering what he'd wear that night. Being able to sleep in nightys and panties was the best. Oftentimes Jack would wake up in the middle of the night with a raging hard-on and have to jerk off before he could fall back asleep. Having so much time alone also allowed him to practice putting on make-up and nail polish. He would spend hours admiring himself in the mirror and imagining that he was getting ready to go out on a date. Then he'd watch some TV while rubbing his cock through the dress and panties. He'd jerk off so often on those weekends that sometimes his little sissy cockette would be rubbed raw. During the weekdays, however, he had much less time to dress. Since he had to be at work right after school and would usually get home after his parents were already home, his opportunities for dressing during the week were severely curtailed. Because of this, Jack tended to get very horny during the week. So much so that he began to visit the basement, and the stash of porn - and particularly the Blue Boy - more and more frequently. He also began going to the maids breakroom when they were they weren't there and digging in the lost and found barrel to find panties, bras and other lingerie to wear. It was this desire that was the cause of Jack's current state of excitement. He'd just finished setting up some tables in the the conference room and called over to the front desk to ask if there was anything else he needed to do at the moment. The front desk clerk told him everything was quiet so Jack went over to the maids' breakroom finding it, as he'd expected, empty. He went over to the lost and found barrel and pushed past the shorts and tshirts that had been there for weeks looking for something he'd seen on his last visit. Buried about halfway down was a pair of red nylon and lace bikini panties and a matching bra. Jack had seen them last week when he'd dug into the barrel but had been interrupted before he could take them when the maids unexpectedly came in for a break. Now, Jack clutched his prize under his flannel shirt as he hurried down to the basement. Once he was safely hidden behind the half wall in the corner, Jack stripped out of his jeans and flannel shirt and slipped on the panties and bra, hooking it on backwards before turning it around and slipping his arms thru the straps. His five and a half inch cockette immediately grew hard and he couldn't resist giving it a rub through the satiny nylon. He reached behind himself and rubbed his ass, reveling in the way it felt in the panties. He adjusted the straps to make the bra fit better and gave his nipples a pinch. Jack swished his hips and whispered to himself, "Oh such a sexy girl, yes you are. You're such a naughty girl, standing here in your bra and panties." Jack arched his back to make his ass stick out and rubbed it again. He began to lift the stack of magazines looking for the issue of Blue Boy he liked. He was always careful to put the Blue Boy magazines back in the stack where he found them so Tom wouldn't notice that he'd been looking at it. He found the issue he'd been looking for. The cover featured a hunky stud with short dark brown hair and an aquiline nose and square jaw. His pectoral muscles were chisled and his small nipples were hard and aching to be sucked. The cover model wore a pair of white jockey shorts that did nothing to hide his huge cock and balls. the model's dick was angled upwards and, although not hard, its outline was prominently displayed. Jack quickly opened the magazine and found the first layout that showed the cover model stripping off his tighty whities. On the next page the model was stroking his now erect cock with his head thrown back and mouth open. Jack guessed the the guy's dick had to be eight inces at least. The bulbous uncut head was glistening and Jack imagined being on his knees sucking it. "Oh yeah," he whispered to himself, "gimme that big cock you hot fucking stud." Jack flipped the pages to another layout that showed two ment, one with long blond hair and blue eyes, like Jack himself, and the other with a short military style crew cut. The spread was supposed to be a military recruit getting a haircut and the first couple of pictures showed Mr. Crew Cut shaving Blondie's head. The next few pictures showed Blondie stripping out of his camos and kissing Mr. Crew Cut. Jack turned the page and moaned at the picture of Blondie on his knees holding Mr. Crew Cut's big cock only inches from his open mouth. "Oh yeah, suck it," Jack said, "Suck that big fucking cock you fucking faggot." Jack was rubbing his own little pricklett through his panties with one hand while holding the magazine in his other. Suddenly Jack heard the door at the top of the stairs open and saw daylight streaming down inthe basement. Oh Shit! He thought to himself. He quickly dropped the magazine on the table and reached down for his pants. He could hear footsteps on the stairs coming down but couldn't see around the wall to see who it was. He'd gotten his pants up but made a quick decision. Jack knew there was no way he'd have time to zip his fly and buckle his his belt and still get his shirt on and buttoned before the person came around the corner. His only hope was that the person would find what they were looking for on the other side of the wall and leave without knowing Jack was down here. If they came straight back to this side ofthe wall they'd see him and his goose was cooked. Jack held his pants closed with one hand while he grabbed his shirt with the other. He leaned his crotch against the table to hold his pants up as he quickly slipped on his shirt and began to button it up. As he did so, he he felt his pants slipping down and pressed harder against the table. The old table wobbled and bumped loudly against the wall. Suddenly Jack heard a voice call out from the bottom of the stairs, "Jack? Are you down here?" It was Tom. Oh Shit! Jack thought to himself for the second time. What's he doing here? He should've gone home by now. Jack was furiously buttoning his shirt and didn't want to speak until he was sure he'd get it buttoned up before Tom came around the corner. "Jack?" tom called again. Jack was on the last button and thought it was safe to reply now, "Um...yeah...I'm...uh...back here Tom." He finished the last button but then felt his heart jump into his mouth when he realized he'd missed a button and his shirt was done up wrong. There was no time to fix it nor was there time to buckle his belt as Tom was roudnign the corner now and so Jack Just leaned against the table and tried to look calm and cool. He reached up and took an old wrench off a hook hanging on the wall above the table to make it look like he'd been doing something other than jerking off. "Hey," Tom walked up next to him. "Hey," Jack replied, "Um..I thought you'd have gone home by now." "Yeah. I was just shooting the breeze with Lauren and Pattie in the laundry room and was about to go. Realized I forgot my gym bag down here. what're you doing down here?" "Um...I needed a wrench to...um...fix an A/C in one of the rooms," Jack said. He felt his pants slip a bit and leaned harder against the table. He looked at Tom and saw the older man looking him up and down. Jack prayed that the bra wasn't visible through a gap in the buttons of his shirt. "Are you ok," Tom asked. "You look a little...flushed." "Um...Yeah...I'm fine," Jack said, his voice quavering a little. Jack noticed Tom looking at the table and he chanced a glance at the table himself and he thought his heart skipped a beat when he saw the Blue Boy laying in the middle of the table all by its lonesome. When Jack looked back at Tom he again noticed the man's eyes scanning him up and down. Tom grinned. "I hope you're not making the pages all sticky," he said wickedly. "Huh? Um...Oh...haha...no...I wasn't looking at...um...anything..." Jack was getting more and more nervous. He could feel his heart beating so hard he thought it must be audible to Tom who was standing closer now. Jack prayed that Tom would just leave. He was scared of being found out. He was scared he'd be fired. He was scared Tom would tell everyone what a sissy faggot he was. The whole town would know. His parents would disown him. He'd never be able to show his face in school. Suddenly, Jack felt Tom put his arm around Jack's shoulders and pull him close. Jack felt his pants slip a bit more. His belt buckle was pressing uncomfortably against the spot right above Jack's cock. Another inch and there'd be nothing holding his pants up. "Jack..." Tom said quietly. "Were you jerking off to the gay mag?" "What?! Haha...No! No way! I...um...was looking for another one and it just fell out and I just..." "Hey Jack," Tom whispered, "Its cool. I'm not gonna tell anyone. You can tell me. We're buddies, right?" Tom gave Jack a friendly hug with his arm around his shoulder. That was it. Tom had pulled Jack just an inch away frmot he table but that was all it took. For an instant there was nothing holding Jack's pants up and they slid down his legs and hit the floor. Jack tried to pull away from Tom to pull his pants back up but Tom held him firmly. Jack knew Tom could see his panties and he wanted to crawl into a hole and die. Just die. He could feel his face turn beet red with the shame and humiliation he was feeling. He couldn't look Tom in the face and just hung his head. "Hmmmm...," Tom said gently. "Cute panties. I see they match your bra." At this Jack did look up. Surprised that Tom had noticed the bra but hadn't said anything till now. "Where'd you get them?" Jack couldn't speak for a moment. Tom sensed how scared the boy was and tilted his head as a way to ask again without speaking. "Th-th-the lost and found barrel," Jack stuttered, his voice barely above a whisper. "Mmmmm...yeah. There's some sexy stuff in there. Those girls find some crazy shit don't they?" Tom asked. He loosened his grip around Jack's shoulders just a bit but still held him close. Jack didn't dare move. Afraid that tom might even hit him if he tried to pull his pants up. "Y-yeah," was all Jack could say. 'You like wearing pretty panties Jack?" Jack merely shrugged. Tom turned Jack to face him. Jack looked down. "Jack? Tell me. Do you like wearing pretty panties and jerking off to the gay mags?" Jack still couldn't admit it. "N-n-no," he lied. "Looks to me like you do," Tom said. "Looks to me like you like wearing panties and bras and looking at big hard cocks. Are you gay Jack? Do you wanna be a girl and suck a guy's dick? Please tell me the truth Jack. I won't be mad and I promise I won't tell anyone." "N-n-no," Jack lied again. "No? You don't want to be a girl and suck my cock for me sweety?" Tom asked. Jack looked up. Had he heard him right? Had Tom just asked him if he wanted to suck his dick? He did want to. Didn't he? Yes. He did. He wanted to see what it felt like to have a cock in his mouth. And he especially wanted to feel Tom's cock in hismouth. but was Tom making fun of him? Would Tom hit him if he admitted it? Would he tell everyone, "Hey Jack's a little cocksucking faggot homo?" Did he dare? Could he? Tom pressed on, "Are you sure sweety? Are you absolutely certain you don't wanna suck my cock baby?" Tom reached his hand down and lightly caressed Jack's cock through his panties. Jack immediatley became hard. No one (except his little cousin) had ever touched Jack's dick like this before. Jack gasped. Tom took one of Jack's hands and placed it on Tom's crotch and, covering Jack's hand with his own, made him squeeze Tom's prick. Jack could feel that Tom was hard as a rock. "Take off your shoes and kick off your pants," Tom said. Jack felt like he was in a daze and did as he was told. Tom took his hand and led him over to an old chair that sat against the wall. It was an old easy chair from one of the guest rooms and smelled musty. Tom pushed Jack lightly in the chest and Jack sat. Jack watched as Tom unbuckled his pants and unzipped his fly. Tom took Jack's hands and placed them on the waistband of his pants. "Pull my pants down Jackie," Tom said. Jack again did as he was instructed. Somewhere in the back of his mind he registered the fact that Tom wasn't wearing any underwear. Tom reached down and rubbed Jack's cockette through the panties. He looked up into Jack's eyes and leaned in and kissed the boy on the mouth. Jack was stunned. He felt Tom's tongue pressing against his lips and he automatically opened his mouth. Tom slipped his tongue lightly inside Jack's mouth and Jack moaned as he felt it fluttering around and over his own tongue like a butterfly. Tom pressed his lips hard against the teen's mouth as he rubbed Jack's cock harder with the palm of his hand. Jack gasped as he felt Tom slip his hand inside his panties and begin to stroke him. Tom broke the kiss and stood. With one hand on the back of Jack's head he urged the young boy's mouth closer to his hard fuckstick. Jack noticed a drop of pre-cum leaking formt he tip. Jack was alternately grossed out and aroused byt the thought of licking that drop and taking the man's cock into his mouth. He looked up into Tom's eyes and the man urged him on. "That's right Jackie. Good girl. Open your mouth and take it in. Take my cock in your pretty mouth sweety and suck it. Be a good girl for me and suck my cock baby." Jack felt like he was in a dream. He opened his mouth and leaned forward, all the while not taking his eyes off of Tom's. He felt Tom's dick enter hism outh. Felt his lips closing on the warm tube of flesh. Tasted the drop of pre-cum. Jack suddenly closed his eyes. He was lost. He was sucking another guy's cock. He was sucking Tom's cock. I'm a cocksucker, he thought to himself. I'm a fucking faggot cocksucker. He felt Tom begin to move. Thrusting his hips and pumping his cock in and out of Jack's mouth. "That's it baby. Suck my cock. Mmmm...good girl. So pretty. So sexy in your panties." Yes, Jack thought, I'm not a faggot. I'm a girl. I'm a sexy girl. I'm a sexy cocksucking girl. Sucking my boyfriend's cock. Jack began to get into it. He began to bob his head on the man's prick. Taking it deeper each time. He gagged a couple of times as Tom's prick hit the back of his throat but he quickly got used to the feel of having a prick in his mouth. He moaned louder now as he accepted himself as a girl. This is what girls do. We suck cocks. I'm a pretty girl. I'm a sexy slut like the whores in the magazines. "Yeah baby. Suck it good. Good little cocksucker. Rub my balls baby." Tom pulled his cock out of Jack's mouth and Jack opened his eyes and looked up at Tom. Tom held his fuckstick up so his balls were right in the boy's face. Jack leaned in closer and stuck out his tongue and licked Tom's nutsack. He giggled slightly as he saw Tom's ballsack shrivel and tighten. Jack reached up and ran a finger along the wrinkled sack and then leaned in and kissed it. He opened his mouth and sucked the whole thing into his mouth and swirled his tongue around, licking and sucking Tom's balls. "Oh fuck yeah baby. Oh that's good. You're a fucking great cocksucker. Lick my fucking nuts you little slut." Tom stroked his cock as Jack licked his balls. Jack reached down to his own little cockette and began stroking himself. Tom let go of his rod and shoved it back into the teen's mouth and Jack picked up where he'd left off bobbing his head up and down on the fleshy tool. Tom reached down and pushed open Jack's shirt and pinched nipples through the bra and then rubbed Jack's tits with the palm of his hand. Tom was face fucking Jack now. His words became harsher and more erotic. "Yeah, yeah...fuck your face bitch...dirty little slut whore....fuckign your fucking cunt mouth bitch...take it...take my cock down your fucking throat you fucking cunt...whore...cocksucking slut...suck it suck it suck it bitch...gonna cum...cum in your mouth...cum in your fucking whore slut mouth...you're gonna drink it bitch...drink my fucking spunk...shoot it down your throat you fucking whore..." tom was pumping faster now and his cock thrusting in and out of Jack's mouth made squishing, slurping noises. Jack was moaning loudly as he felt his own orgasm approaching. Suddenly Jack gave one last loud moan as he felt the wave of pleasure sweep over his body, "Mmmmmmm....mmmmmm...MMMMMMM!!!!" That was all it took to set Tom off too. "Ohhhhhhh FUCK SHIT FUCK I'm cummmmmingggg fuckin bitch slut fuckmmmmmmmmmmm..." Jack suddenly felt a shot of hot salty liquid in hismouth. He tried to swallow but another shot follwed the first and then another. It felt like his mouth was being flooded by hot salty milk and he couldn't swallow fast enough. While he was swallowing one load another came out and leaked out of the corners of Jack's mouth. Tom gave one last thrust and jack felt his balls hitting his chin. He gagged once and cum flew out of his mouth and dripped down his face. He felt his own cum dribbling down his cockette and over his hand. Tom's prick began to soften and Jack gave it a final slurp as Tom pulled out. Tom leaned down and licked his cum frm Jack's face and then stood back. He looked around for something to wipe himself with and saw Jack's underwear laying on the floor. He picked them up and wiped his dick and then buckled his pants. He tossed Jack his jockey shorts and Jack wiped his face. Tom came over and leaned down and kissed Jack softly on the lips. "Don't worry Jack," Tom said gently, "I'm not going to say anything to anyone. this is our little secret 'k?" Jack just nodded. He felt thrilled and excited, but also ashamed and humiliated. When he looked up, he saw Tom's back rounding the corner and heard him walking up the stairs. He saw the daylight spill in frm the basement door and heard it close and he was alone in the basement. Jack looked down at himself and wondered if this would ever happen again. Was he gay? Bi? Was Tom gay? Bi? He slowly stood and took off the bra and panties. Taking care to button his shirt right this time, he then buckled his belt and stuffed the bra and panties into a box under the table. He thought about taking them home but worried that they might stick out of his pocket or that his mom or dad would find them. Jack felt like he was coming out of a dream. He picked up the Blue Boy from the table and stuffed it back into the middle of the pile of magazines where he'd found it. He didn't want anyone to know he'd been looking at it. The last few minutes were becoming hazy. What did Tom and I just do? Had Tom seen me looking at the Blue Boy? No, it was just a really vivid fantasy while I was jerking off...but...did someone come down here? Did someone almost catch me...? I didn't just....no...I must have imagined it....Jack continued to tell himself that. It was just a dream...just a dream....